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The fundamental attribution error is the tendency to explain another person’s behavior mainly through their personality while underweighting the situation they were in. At work, it turns a missed deadline into “they are unreliable” and a quiet colleague into “they are disengaged.” The judgment arrives fast and feels obvious. It is frequently wrong.
This matters most where judgments carry consequences: performance reviews, feedback conversations, promotion decisions, and conflict between teammates. Correcting the error does not mean excusing weak work. It means putting evidence before character, so the response you choose actually fits the problem in front of you.
What Is the Fundamental Attribution Error?
The fundamental attribution error is a cognitive bias in social perception. An observer watches a behavior, then treats it as a reliable readout of stable traits, giving too little weight to the constraints, information, and pressures behind it.
It sits within the wider field of attribution theory, which Fritz Heider helped establish in 1958. A 1967 study by Edward Jones and Victor Harris found that people could infer genuine attitudes from essays writers had been assigned to produce. Lee Ross later named the error in 1977. The American Psychological Association’s definition describes the same pattern: overestimating the role of enduring personal characteristics while underestimating situational influences.
The research literature also calls it correspondence bias because an observer infers that a person’s disposition corresponds neatly to the behavior just witnessed.
A simple example at work
A teammate misses a deadline. The fast judgment is a character judgment: they are unreliable. The fuller picture may involve one or more of these:
The scope changed after the work started and nobody reset the date.
A dependency arrived late from another team.
Two stakeholders each marked their request urgent.
The task required a skill the person was never trained in.
Workload planning assumed capacity that did not exist.
There is a real, repeated performance problem.
“Unreliable” is a conclusion, not an observation. That last item belongs on the list, though: situational explanations are not automatically true, and defaulting to them is its own error.
What the fundamental attribution error does not mean
Traits still matter. Some people are disorganized. Some avoid difficult work. Dispositional explanations are sometimes correct.
Not every failure has an external excuse. Context can explain an outcome without justifying it.
The conclusion follows the evidence. Investigate the situation. Do not assume it.
Why We Misjudge Other People So Quickly
Behavior is visible. Constraints are not. You see a colleague arrive late to standup. You do not see the escalation they handled at 6 a.m. or the second manager quietly reassigning their week. You are not weighing a dispositional explanation against a situational one and choosing badly. You are weighing one you can see against one you cannot.
Dispositional attribution and situational attribution
Attribution theory separates explanations into two types:
Dispositional attribution works through something internal and durable: traits, character, attitude, ability, or motivation. “She pushed back because she is difficult.”
Situational attribution works through something external: unclear expectations, incentives, role design, available information, deadlines, or resource constraints. “She pushed back because the request arrived after the estimate was committed.”
Neither is inherently more accurate. The error is reaching for the dispositional explanation before checking whether a situational one accounts for what you saw.
Why one incident becomes a character judgment
A trait label is efficient. It compresses a messy event into a portable summary you carry into the next staffing decision and review cycle. Once the label exists, confirmation bias maintains it: a follow-up question reads as pushback, and a quiet week reads as coasting. Where the manager-employee relationship has already frayed, hostile attribution bias can push further, causing neutral actions to read as deliberate slights.
Stable judgments need three things one incident cannot supply: a pattern across time, direct information about conditions, and answers from the person themselves.
Does culture change the fundamental attribution error?
Culture can influence the explanations people habitually prefer, but it should not be treated as immunity from attribution bias. A study comparing individualist and collectivist cultures found correspondence-bias effects in both groups and did not report a cultural difference in that study.
On a global team, do not assume a colleague from a collectivist culture is immune, and do not assume the error operates identically everywhere either.
Fundamental Attribution Error Examples at Work
Performance reviews
A manager writes up an engineer after a weak quarter. The rating language drifts toward disposition: low ownership, lacks drive, not proactive.
What the review period actually contained:
The team’s objectives were rewritten in week five.
Two people left and were not backfilled.
The engineer absorbed on-call coverage for a system they did not build.
The manager’s expectations were communicated verbally and never written down.
None of that turns a weak quarter into a strong one. It changes the correct response. A capability gap needs training. An unclear objective needs a written goal. A staffing hole needs a staffing decision.
A motivation problem needs a direct conversation. The wrong cause guarantees the wrong fix, and the employee reads the assessment as unfair because it does not match what they lived through.
Managers who give developmental feedback based on specific, behavior-based evidence produce assessments people can act on because they name an event rather than a personality.
Feedback and difficult one-on-ones
Attribution errors run in both directions here.
A manager delivers blunt feedback. The employee reads bluntness as a character statement: this person does not respect me. The manager may be working from incomplete information or carrying pressure from their own review.
The employee then goes quiet, and the manager reads defensiveness as a bad attitude. Likely explanations include surprise, ambiguity about what went wrong, or fear about what the feedback means for their job.
Two people are making dispositional inferences about each other inside the conversation designed to close that gap.
Team conflict and missed communication
A colleague takes two days to answer a message and the inference is dismissiveness. Alternatives worth ruling out first:
Meeting load left no processing time.
Ownership was never assigned, so nobody felt responsible.
Time zones pushed the exchange into a two-day cycle.
The message asked for a decision the person cannot authorize.
There is a genuine relationship problem needing a direct conversation.
The last option is real. The error is not concluding it. The error is concluding it first.
Hiring and promotion decisions
Interviews and promotion panels compress a person into a handful of moments, most under unusual conditions. A candidate who presents flatly may be a flat presenter, or may be interviewing for the first time in years.
A strong performer who fumbled one visible launch may have made a bad call, or inherited a scope that was never viable. Structured evidence is the counterweight: defined criteria, more than one assessor, and written examples tied to specific situations.
Fundamental Attribution Error vs Related Biases
The distinctions matter.
Fundamental attribution error vs actor-observer bias
These are not the same claim.
Fundamental attribution error: An observer overweights another person’s disposition and underweights their situation. This is a claim about how we explain other people.
Actor-observer hypothesis: The broader claim that people explain their own conduct situationally and other people’s conduct dispositionally. This is a claim about an asymmetry between self and other.
The useful workplace takeaway is not that people always excuse themselves and blame others. It is that both self-judgment and judgments of others need evidence, context, and a willingness to test the first explanation.
Fundamental attribution error vs self-serving bias
Self-serving bias concerns how people explain their own outcomes. Success gets attributed internally: my judgment, my effort, my skill. Failure gets attributed externally: the market, the timeline, the other team.
A project lead claims personal credit for a launch that landed, then explains a failed launch entirely through budget cuts and vendor delays. The fundamental attribution error points outward at someone else. Self-serving bias points inward.
Fundamental attribution error vs ultimate attribution error
The ultimate attribution error extends the pattern to groups. Negative behavior by an out-group member gets explained by the group’s supposed character, while the same behavior by an in-group member gets explained away by circumstances. Positive behavior can flip the pattern, with an out-group success dismissed as luck.
At work, this can show up in how one department talks about another.
How to Avoid the Fundamental Attribution Error at Work
Advice to “show more empathy” does not survive contact with a real performance problem. What works is a sequence you can run in minutes before a review or a hard conversation.
1. Start with observable behavior
“Lazy,” “difficult,” “not leadership material,” and “low ownership” are conclusions wearing the costume of observations. Delete the label and write down instead:
The specific event and when it happened.
The expected standard and where it was set.
The impact on the work, team, or customer.
The evidence you hold personally, separated from what you heard secondhand.
If you cannot complete those four lines, you have an impression rather than an assessment.
2. Test for patterns and context
Ask whether this is a one-off, a repeated pattern, or a symptom of the system around the person. This is root-cause analysis applied to human performance. Check each before deciding:
Workload and competing priorities during the period in question.
Role clarity and whether ownership was explicitly assigned.
Tools, access, and information available at the time.
Dependencies on other people or teams.
Incentives, including what the person is rewarded for elsewhere.
Capability and whether training was provided.
A pattern across multiple review periods supports a different conclusion than one bad month.
3. Ask before deciding
Neutral questions surface constraints you cannot see. They concede nothing:
“What made this difficult?”
“What information or constraint affected the outcome?”
“What would need to change for the next attempt to succeed?”
Psychological safety is what makes the answers usable. If the person expects their answer to be used against them, you get a defensive account rather than an accurate one.
4. Make the next step specific
End every one of these conversations with something concrete: a change in behavior, a change in support, a process fix, or a revised timeline. Write down what was agreed and set a review date.
Where accountability still applies
Investigating context is not the same as accepting every explanation. If the pattern repeats after constraints are addressed, expectations are written down, and the person confirms they have what they need, the situational explanation has been tested and has not held.
The correct response is a performance conversation, not another round of context gathering. Fairness is a standard of evidence, not a lowered bar.
Using This in Performance Reviews and Feedback
For managers
A written review outlives the conversation that produced it, so the standard is higher:
Name the cause you concluded and the evidence behind it, so the rating can be challenged on facts rather than tone.
Record the constraints you found, even where they did not change the rating. An employee who sees their context acknowledged can address the conclusion rather than the process.
Avoid trait adjectives in written ratings. “Missed three committed dates in Q2” survives scrutiny. “Lacks drive” does not.
For employees
Before concluding that feedback is unfair, run the same test in reverse. Ask what behavior was observed, over what period, and what impact it had. Ask what evidence would change the assessment.
Then supply your context without turning it into a defense. “The scope changed in week five and the date was never reset” is information. “That is not my fault” ends the conversation. Learning to respond deliberately in a difficult workplace moment is a skill rather than a temperament, and it separates a conversation that adjusts an assessment from one that confirms it.
The shift is small and mechanical. Replace the character verdict with four questions:
What happened?
What pattern does the evidence support?
What constraints were operating?
What still needs a conversation?
Run them before the review is written, not after it is contested.
If you are preparing a performance conversation and want the assessment to hold up, rebuild your feedback process around observable evidence. For applying this in live situations, PathWise coaching works through real conversations as they happen, and you can tell the team what you are dealing with to find the right fit.
How to Handle Difficult Employees: A Manager’s Guide
September 4, 2026
How to handle difficult employees starts with one shift: address specific, repeated behavior early, not a label. Back every conversation with evidence. Follow a fair, consistent process instead of reacting to frustration.
A manager’s job is not to diagnose someone’s personality. It is to clarify what the role requires, hear the employee’s side, offer real support, and document what actually happened. “Difficult employee” describes a search term, not a diagnosis. The behavior behind it might be missed deadlines, resistance to feedback, or a pattern of blame-shifting that affects the team. Treating it as a management problem, not a character flaw, keeps the response fair and defensible.
One-off misunderstandings between peers with no reporting relationship.
A personal dislike for an employee, absent an actual performance or conduct problem.
Medical, legal, discrimination, safety, or protected-leave situations, which need immediate HR or specialist involvement.
Recognize the Difference Between a Difficult Moment and a Management Issue
Learning how to handle difficult employees starts with telling a bad day apart from an actual pattern. A single rough meeting or a missed deadline during a hard week is not a management issue. It becomes one when the behavior repeats, or when a performance gap is clear and consistent over a defined period.
Common Patterns That Require a Manager’s Attention
Work consistently falls below the agreed standard.
The employee misses commitments or deadlines without flagging problems early.
Teamwork or communication breaks down repeatedly, not just once.
Feedback gets rejected without any real engagement with it.
The employee avoids accountability or shifts blame onto others.
The employee resists a necessary change without raising workable concerns.
Check Whether the Problem Is Actually a Management or System Issue
Before the first conversation, confirm the basics are actually in place:
Expectations, priorities, workload, and success measures are clear and were communicated.
The employee has the training, tools, and authority the role requires.
This check is not an excuse for repeated poor behavior. It exists so the manager acts on accurate information instead of assumptions.
Gather Facts Before You Start the Conversation
Fair feedback and useful documentation both start with the same discipline: write down what happened, not what you assume it means.
Separate Observable Behavior From Subjective Labels
Weak: “You are negative and difficult.”
Strong: “In the last three project meetings, you interrupted colleagues before they finished and rejected agreed actions without offering an alternative.”
Specific language gives the employee something concrete to respond to. A label just invites defensiveness.
Identify the Expected Standard and the Impact
State the standard the behavior fell short of: a policy, a role requirement, a deadline, or a team agreement. Then name the actual impact, on a customer, a colleague, a delivery date, or the quality of the work. Skip exaggeration like “everyone is unhappy.” Vague claims collapse under a follow-up question, and they are unfair to the employee if you cannot back them up.
Know When to Involve HR Before the First Meeting
Loop in HR before you say anything to the employee if the situation involves:
Harassment, threats, or violence.
Discrimination or retaliation.
A medical concern, accommodation request, or protected leave.
Union matters or a serious policy breach.
HR involvement at this stage protects the employee and the organization. This guide is not legal advice. For any of the situations above, follow your internal policy and get qualified local counsel involved.
Have the First Performance Conversation Early
Difficult conversations get harder the longer a manager waits. Hold the meeting privately, prepared, and direct, while the behavior is still recent.
Use a Clear Conversation Structure
A five-part structure keeps the conversation direct without becoming personal, building on the situation-behavior-impact model described by theCenter for Creative Leadership:
Situation: name when and where the issue happened.
Behavior: describe only what you observed.
Impact: explain the consequence.
Expectation: state what needs to change.
Question: ask for the employee’s perspective and any context you are missing.
Listen Without Losing Clarity
Ask questions that invite a real answer:
“What is your perspective on what happened?”
“What is making this expectation difficult to meet?”
“What support or clarification would help you meet it?”
Listening is not the same as accepting an excuse or lowering the standard. It is how you find out whether the fix is coaching, a resource gap, or a direct accountability conversation.
End With an Agreed Next Step
Close every conversation with three things: what needs to change, what support you will provide, and a specific check-in date with a clear description of what improvement looks like. Managers whogive feedback effectively treat this step as part of the conversation, not an afterthought tacked on at the end.
Document Performance Concerns Fairly and Consistently
Documentation is not a punishment, and it is not a retrospective attempt to build a case. It is a factual record of expectations, support, feedback, and progress that both sides can point back to.
What Managers Should Document
Date, time, and relevant context.
The observable behavior or work output.
The expected standard and its impact on the business or team.
The employee’s response or explanation.
Support offered, agreed actions, and the next review date.
Evidence of improvement, no change, or a new concern.
What Managers Should Not Document
Personality labels or guesses about motivation.
Irrelevant private or medical details.
Rumors or secondhand claims you have not verified.
Conclusions that belong to HR, legal counsel, or a formal investigation.
Keep Documentation Aligned With Company Policy
Follow your organization’s HR and data-handling process for storing these records. Inconsistent documentation across managers or employees undermines fairness and makes later decisions harder to defend.
Coach for Improvement Before Escalating
Give the employee a genuine, structured chance to improve where the situation allows for one. Ordinary coaching and a formal improvement plan are not the same thing, and skipping straight to the second reads as punitive.
Create a Practical Improvement Plan
Effective plans share a small set of features, whether or not they use a formal performance improvement plan.SHRM’s guide to performance improvement plans recommends a minimum of 30 days, with 60 to 90 days more typical for a genuine improvement window. Build the plan around:
The specific behavior or outcome that needs to change.
A measurable standard, not a vague impression.
The support, training, or resources available.
A defined timeline with regular check-ins.
What happens if progress falls short, in line with your organization’s policy.
Give Feedback Throughout the Process
Reinforce real progress as it happens, not only at the final review. Correct new issues promptly instead of saving them up. Keep every note specific and tied to the agreed standard, not to how the conversation felt.
Avoid Turning a PIP Into a Surprise
A formal improvement plan should follow earlier, clear feedback, unless the issue is serious enough to require immediate escalation. Build the plan with HR or under your organization’s established process. An employee who is blindsided by a PIP has a legitimate complaint about the process, whatever the underlying performance issue turns out to be.
When to Escalate to HR or Senior Leadership
Escalation is not failure. It is the right step when the situation needs authority, expertise, or policy knowledge beyond what one manager holds alone.
Signs Informal Coaching Is Not Enough
The pattern continues after clear feedback and reasonable support.
The issue affects safety, customers, team function, or compliance.
The employee refuses to engage with the process at all.
A formal warning, PIP, investigation, reassignment, or termination looks likely.
Partner With HR Before Formal Action
Before you take a formal step, review the evidence, the policy requirements, and how similar situations were handled for other employees. Make sure the employee understands the issue, what needs to change, and the process ahead. Avoid implying an outcome before HR has weighed in.
Handle an Exit Process Respectfully
If the relationship ends, keep the process dignified and confidential, and communicate through the channels your organization has defined. The exact steps vary by employer policy and jurisdiction, so treat this as a decision to make with HR and qualified local counsel, not a script to follow alone.
Common Mistakes Managers Make With Difficult Employees
Waiting Until Frustration Takes Over
Delayed feedback turns a manageable pattern into a formal problem. A timely, proportionate conversation early is easier for everyone than a heated one after months of silence.
Making the Discussion About Personality
“Unmotivated,” “toxic,” and “bad attitude” are weak starting points that describe the manager’s exhaustion more than the employee’s behavior. Replace the label with behavior, impact, and expectation every time.
Being Inconsistent Across Employees
Similar issues need similar standards and similar documentation. Inconsistency is one of the most common HR-sensitive complaints, and one of the hardest to defend after the fact.
Giving Feedback but Failing to Follow Through
A missed check-in, a vague plan, or a consequence that never arrives damages trust with the employee, and it signals to the rest of the team that the standard is optional.
Treating Peer Conflict as a Disciplinary Issue by Default
Not every interpersonal problem is a performance issue. If the situation is really a clash between colleagues with no reporting relationship, our guide todealing with difficult coworkers covers the right approach for that instead.
Manager Scripts for Common Situations
An Employee Repeatedly Misses Deadlines
“You’ve missed the last three delivery dates for this workstream, and each one pushed the release back for the rest of the team. I want to understand what’s getting in the way before we set the next date. What’s been blocking you?” Assume a blocker, not a lack of commitment, until the conversation rules it out.
An Employee Reacts Defensively to Feedback
“I hear this feels unfair, and I want to understand your side. The behavior I need to change is [specific example], and the expectation going forward is [specific standard].” If the conversation gets heated, pause it and reschedule for later the same day rather than pushing through.
An Employee’s Behavior Is Affecting the Team
“In the last two sprint reviews, you cut off two teammates before they finished their update, and the team has stopped raising blockers there. That’s the specific impact I need to see change.” Stay on the observed pattern, not on what colleagues have said about the person.
An Employee Refuses Accountability
“I hear that the timeline was tight. The deliverable was still three days late and wasn’t flagged in advance, and that’s what I need to address. What can you do differently next time, starting with today’s task?” Redirect blame-based answers toward ownership and a next action. If the pattern repeats after two or three redirected conversations, document it and involve HR.
How First-Time Managers Can Prevent Problems Earlier
Proactive management prevents more problems than any conversation held after the fact, and this matters most in a manager’s first year. Ourfirst-time manager guidance covers the fundamentals in more depth.
Set Expectations From the Beginning
Clarify priorities, quality standards, who decides what, communication norms, and how often you will check in. Research from theProgram on Negotiation at Harvard Law School points to a simple mechanism: people make better, less overconfident decisions when they know in advance they will be held accountable.
Ambiguity at the start turns an ordinary performance gap into a dispute over what was agreed.
Make Feedback Routine
Regular feedback and recognition make corrective feedback feel normal instead of alarming. An employee who only hears from their manager when something is wrong will read every conversation as a warning shot.
Build a Record of Support as Well as Concerns
Document training provided, check-ins held, real progress, and any accommodations made, through the right channel. A record that only shows problems looks selective, even when it isn’t.
Be Specific, Fair, and Timely
Knowing how to handle difficult employees well comes down to a short, repeatable sequence: gather the facts, address the behavior early, listen without lowering the standard, document consistently, coach with a real plan, and escalate when the pattern doesn’t change. None of that requires guessing at someone’s character.
If a direct report’s behavior is costing your team time, trust, or output,talk to PathWise about your team’s situation to work through the specific pattern you’re dealing with and what a fair next step looks like.
An emotion wheel is a visual chart that helps you move from a broad feeling to a precise one. You start at the center with a wide category such as anger, sadness, or joy, then move outward to a more specific word that actually fits what you are experiencing. The tool exists for one reason: most people have more feelings than words, and the gap between the two makes emotions harder to work with.
It is a reflection prompt, not a diagnostic test. Choosing a word on a wheel tells you nothing about whether you have a clinical condition, and it does not replace care from a qualified professional. What it does well is narrow vague discomfort into something specific enough to act on. Once you can say what you feel with accuracy, you can decide what to do next instead of reacting on impulse.
What Is an Emotion Wheel?
An emotion wheel, also called a wheel of emotions or a feelings wheel, arranges emotion words in rings so you can locate a general feeling and then refine it. The inner ring holds broad categories. The outer rings hold narrower words that belong to those categories. Movement across the wheel is the whole method.
This article uses Plutchik’s wheel as its main reference point because it is a widely used model of how emotions relate to one another. Other wheels organize feelings differently, with different core categories, ring counts, and color schemes. No single wheel is the definitive scientific classification of human emotion.
The difference between a feelings wheel and Plutchik’s wheel
The Feeling Wheel is attributed to psychologist Gloria Willcox. As a recent overview of the model explains, it begins with six broad feelings and expands into more specific emotion words as you move outward. Many printable wheels circulating today descend from that design.
Plutchik’s wheel comes from a different tradition. Psychologist Robert Plutchik proposed it as part of his psycho-evolutionary theory of emotion, and it does more than expand vocabulary. It maps several structural relationships:
Core emotions. Eight primary emotions sit as the base categories: joy, sadness, anger, fear, surprise, disgust, trust or acceptance, and anticipation.
Related emotions. Each core emotion has milder and stronger relatives. Annoyance, anger, and rage are the same family at different strengths.
Intensity. Position on the wheel encodes strength. In Plutchik’s layout, emotions intensify as they move toward the center and soften toward the outer edge.
Opposing emotions. Primaries are arranged in opposed pairs: joy against sadness, trust against disgust, fear against anger, surprise against anticipation.
Blended feelings. Two adjacent primaries combine into a compound emotion. Joy and trust produce love. Sadness and disgust produce remorse. These combinations are usually called dyads.
Not every wheel shares this architecture. Some have six core feelings rather than eight, some run intensity outward instead of inward, and some use no color coding at all. Check which convention your wheel follows so you are not reading intensity backwards.
Why naming feelings can be difficult
Naming a feeling accurately is a skill, and several ordinary conditions get in the way of it:
Limited emotional vocabulary. Some people rely on a small working set of emotion words. When the options are “fine,” “stressed,” “tired,” “annoyed,” and “bad,” every experience gets forced into one of them.
Rushing past body signals. Emotions show up physically first: a tight jaw, shallow breathing, heat in the chest. Skipping past interoception, the sense of what is happening inside your body, removes your best evidence.
Social pressure. Some feelings are easier to admit than others. Anger is often more socially acceptable than hurt, so hurt gets reported as anger.
Several feelings at once. When relief, guilt, and resentment show up together, the mix reads as confusion rather than three distinguishable things.
Affective science has a name for the ability to make fine distinctions between feelings: emotional granularity. A 2025 scoping review defines it as the ability to recognize, distinguish, and articulate experienced emotions in fine-grained categories. The practical version is simple. “Bad” gives you nothing to work with. “Overwhelmed,” “anxious,” “resentful,” and “disappointed” each point to a different problem and a different response.
How the Emotion Wheel Works
Most wheels are read from the center outward. You identify the closest broad family first, then step out into the ring of narrower words, then pick the one that fits. The sequence matters because scanning every word at once can produce decision fatigue rather than clarity.
Intensity and category placement both depend on the wheel. A word that appears under fear on one wheel may appear under sadness on another. Read the wheel in front of you rather than assuming a universal layout.
Start with the closest core feeling
Pick the broad family that feels nearest and accept that it may be imperfect. Using Plutchik’s set, the options are joy, sadness, anger, fear, surprise, disgust, trust or acceptance, and anticipation. You are choosing a starting point, not delivering a verdict. If two families both seem close, note both and continue. If none fit, choose the one you would rule out last.
Move outward to name the feeling more precisely
This is where the tool earns its keep. Anger, once opened up, becomes irritation, frustration, resentment, or rage, and those four call for different responses. Irritation may pass with food and sleep. Resentment usually points at a boundary that was crossed weeks ago.
Sadness splits the same way. Disappointment attaches to an expectation that did not happen. Grief attaches to a loss. Loneliness attaches to an absent connection. Discouragement attaches to effort that is not producing results. Same family, four different next steps.
Notice mixed emotions and intensity
You can hold more than one emotion about the same event, including emotions that seem to contradict each other. A new opportunity is the standard example: you can feel proud of being chosen and anxious about the responsibility at the same time, and both readings are accurate.
Resolving that into a single feeling loses information. Pride tells you the opportunity matters to you. The anxiety tells you there is a gap between the role and your current confidence, which is a preparation problem rather than a reason to decline. Rating each feeling roughly on a scale of one to ten usually reveals which one is driving your behavior.
How to Use a Feelings Wheel in Five Steps
The full process takes about two minutes once it is familiar. Here is the sequence.
1. Pause and describe what is happening
Before reaching for any label, describe the raw material in plain language. Cover four things: what your body is doing, what your thoughts are doing, what you want to do, and what just happened.
Useful descriptions sound like this: “My shoulders are tense.” “I keep replaying the conversation.” “I want to withdraw and not answer messages.” “My manager changed the deadline in a group chat.” None of that is clinical language. It is evidence.
2. Choose a broad emotion family
Move to the inner ring and select the closest core emotion. Do not search the whole wheel. Uncertainty here is expected, and picking the wrong family costs nothing because the next step corrects it.
3. Find the most accurate word
Move outward and read the narrower options in that family, comparing two or three that seem close. The distinctions are usually easy once stated: embarrassed is about being seen, ashamed is about who you believe you are. Nervous is forward-looking, uneasy is unfocused. Frustrated means blocked, disappointed means let down.
4. Ask what the feeling may be signalling
With a specific word in hand, look at context. Ask what triggered it, what need is going unmet, which value or boundary is involved, and what expectation you were holding. Note whether sleep, workload, hunger, or an ongoing situation is amplifying the reaction.
Resist the idea that every emotion carries one universal message. Anger does not always mean a boundary was crossed, and anxiety does not always mean danger. The question is what this instance is pointing at.
5. Choose a proportionate next action
Match the response to the size of the feeling. Options include taking a break, naming a boundary, asking a clarifying question, writing it down, talking to someone you trust, or returning to the issue later when you are steadier.
Keep feeling and action separate. A feeling can be valid while the impulse attached to it is a bad idea. Resentment toward a colleague can be a fair reading of the situation and a terrible basis for a message sent at eleven at night. Naming the emotion buys the pause in which you respond rather than react.
Emotion Wheel Examples for Everyday Situations
Definitions are easier to follow when attached to something recognizable.
“I feel stressed”
Stress is a container word, not an emotion. Opened up, it resolves into something more specific, and each option leads somewhere different:
Anxious. Something ahead of you feels uncertain. The next question is what specifically you are anticipating.
Pressured. Demands exceed available time. The next question is what can move or be dropped.
Overwhelmed. There is too much to hold at once. The next question is what to write down and sequence.
Frustrated. Something is blocking progress. The next question is what the obstacle actually is.
Unprepared. You lack information or a skill. The next question is what you need and who has it.
Five words, five different conversations. “Stressed” produces none of them.
“I’m emotionally and mentally drained”
People describe this state in several ways: emotionally and mentally drained, mentally and physically and emotionally tired, or physically, mentally, and emotionally drained. The phrasing varies and the underlying cause varies more.
That language can describe prolonged stress at work, disrupted sleep, caregiving strain, grief, a period of conflict, an untreated physical health problem, or simply a hard month. A wheel can help you separate the components. You might find that “drained” is actually resentment plus fatigue, or grief plus guilt, or discouragement plus loneliness.
What a wheel cannot do is identify the cause. Emotional exhaustion is a described pattern, not something a keyword or a checklist can confirm about you. If the state has persisted, that is a reason to talk to someone qualified rather than to self-label. Prolonged depletion that touches your work is also worth reading about in the context of dealing with burnout, which overlaps with this experience without being identical to it.
“I’m angry with someone I care about”
Anger toward someone close is usually a composite. Pulling it apart surfaces several distinct feelings:
Hurt. Something they did landed painfully.
Disappointment. They did not do what you expected.
Jealousy. They have the attention, time, or standing you wanted.
Fear. The relationship or your standing in it feels less secure.
Resentment. An older unaddressed grievance is still running.
Anger. A limit was crossed and you want it acknowledged.
The communication difference is large. “You made me feel bad” gives the other person nothing to work with and invites a defense. “I feel disappointed because I expected you to tell me before deciding” names the emotion, the expectation, and the gap, which is specific enough to answer. Precision of this kind is a core part of effective communication skills.
The Emotion Wheel and Emotional Intelligence
An emotion wheel is a self-awareness tool that supports emotional intelligence. It is not an “emotional intelligence wheel,” and it produces no score or EQ rating. It supports one capability: identifying your own emotional state accurately.
Build self-awareness before trying to regulate a feeling
Regulation strategies work better when aimed at the right target. Breathing exercises help with acute anxiety and do very little for resentment. A difficult conversation resolves resentment and does nothing for fatigue. Getting the label right is what makes the choice of strategy meaningful rather than random.
Putting feelings into words can make an experience easier to describe to yourself and discuss with someone else. It is a tool for reflection, not a way to erase feelings.
A short habit builds the skill: name the feeling, rate its intensity, note the trigger. Three lines.
Use clearer language in conversations
Vague emotional statements create conflict because they assign blame without describing anything. Specific ones describe an experience the other person can respond to.
In a relationship: “I felt lonely this week” rather than “you have been distant.”
In a family: “I felt dismissed when the plan changed without me” rather than “nobody cares what I think.”
At work: “I am frustrated because the requirements changed twice after we started” rather than “this project is a mess.”
In coaching or a one to one: “I am discouraged, not disengaged” rather than “I am fine.”
Each version names a feeling and attaches it to an observable event, which is what makes a statement discussable. The habit is a practical extension of knowing yourself well enough to describe your own reactions accurately.
Create a simple daily check-in practice
Run a two-minute check-in once a day, ideally at a consistent time. Four questions:
What am I feeling right now?
How intense is it, on a scale of one to ten?
What happened before it?
What do I need next?
Look for patterns weekly rather than analyzing every entry. The goal is noticing recurring triggers, not monitoring every emotion as it arrives, because continuous self-surveillance becomes its own source of strain.
When Feeling Drained Needs More Than an Emotion Wheel
A reflection tool has limits, and depletion that keeps going is one of them.
Signs it may be time to slow down and seek support
A medically reviewed 2026 overview from Acıbadem International describes emotional exhaustion as a state that can develop after prolonged stress. It notes that signs may include fatigue, irritability, poor concentration, low motivation, sleep or appetite changes, headaches or muscle tension, detachment, and social withdrawal.
Recognising a few of those in yourself is not a diagnosis. It is a reasonable prompt to reduce a stressor where you can and to consider talking to someone.
When to speak with a qualified professional
Contact a doctor or a qualified mental health professional when distress is persistent, when it is worsening rather than easing, when it is interfering with work, sleep, or relationships, or when it comes with physical symptoms you cannot account for. A clinician can look at causes no wheel can see, including sleep disorders, thyroid problems, anemia, medication effects, anxiety disorders, and depression.
If you are having thoughts of harming yourself, or you are in immediate danger, contact your local emergency number or a crisis line in your country now. That situation calls for direct help, not a reflection exercise.
Common Mistakes When Using an Emotion Wheel
Treating emotions as good or bad
Sorting feelings into positive and negative usually ends in suppressing half of them. Emotions carry information about what is happening and what matters to you, and anger, envy, and disgust are as informative as gratitude. The work is awareness followed by a deliberate choice.
Choosing the first word that sounds familiar
Habit words win by default. If you always land on “frustrated,” read the two or three words next to it and test them against the situation first. The value comes from the comparison, not the first click.
Using the wheel to avoid the underlying issue
Naming a feeling can become a substitute for addressing it. Identifying resentment about an unfair workload is step one. Raising it with the person who can change it is the step that matters.
Turning a normal feeling into a diagnosis
Feeling drained for a week is not the same as a clinical condition, and self-labeling from a keyword can lead either to unnecessary alarm or to dismissing something that needs attention. Treat “emotional exhaustion” as a reason to reflect and possibly seek support, not a conclusion about yourself.
Next Steps: Name the Feeling Before You Manage It
The method is short enough to remember without a printout. Pause and describe what is actually happening. Choose the closest broad feeling. Get specific. Identify the context and what the feeling is pointing at. Then pick a proportionate response. Repeat it often enough and the precise words start arriving on their own, which is the real outcome: a wider vocabulary for the week you are actually having.
If reading your own reactions accurately is the skill you want to build, our first-time manager coaching works on exactly that alongside communication and decision-making, or you can talk to PathWise about coaching about where you are getting stuck.
Bad character traits are repeated attitudes and behaviors that damage trust, communication, and results at work. They differ from a single bad day because they form a pattern that colleagues learn to expect and quietly work around.
The twenty traits below cause the most damage in professional settings, from dishonesty and blame-shifting through to micromanaging and chronic procrastination. Each entry explains what the trait looks like on the job, the harm it does, and the specific behavior to practice instead.
Quick List of 20 Bad Character Traits at Work
Every trait gets a full explanation further down, grouped into the four problem areas where negative character traits usually cluster.
Trust and accountability problems
Dishonesty: hiding mistakes or misstating progress
Blame-shifting: redirecting fault onto colleagues
Unreliability: missing commitments without warning
Manipulation: steering people through pressure or half-truths
Entitlement: expecting rewards without contribution
Communication and relationship problems
Poor communication: withholding or scattering information
Disrespect: dismissing people, roles, or boundaries
Gossip: discussing colleagues instead of addressing them
Lack of empathy: ignoring the human cost of decisions
Ego and control problems
Arrogance: rejecting feedback and dominating discussion
Micromanaging: controlling work already delegated
Defensiveness: treating feedback as an attack
Unhealthy competitiveness: winning at a teammate’s expense
Chronic negativity: rejecting ideas by reflex
Initiative and adaptability problems
Lack of initiative: waiting to be told
Inflexibility: resisting reasonable change
Inconsistency: shifting direction without notice
Impulsivity: acting before checking
Chronic procrastination: delaying work until it turns urgent
What Counts as a Bad Character Trait at Work?
A bad character trait is a consistent tendency that repeatedly produces a harmful workplace outcome across different situations and different people. The label matters far less than the pattern.
Not every irritating moment qualifies. A colleague who snaps once during a difficult quarter is having a hard week. A colleague who snaps at anyone who questions their work has a pattern.
Character Trait vs. One-Off Behavior
Behavior is a single action. A trait is the tendency that keeps producing that action.
The practical test is repetition across context. If the same behavior appears with different people, in different meetings, under different levels of pressure, it is a trait. If it appeared once during a product launch and never again, it was a reaction to circumstances.
This distinction protects people from unfair judgment. It also prevents the opposite error, which is excusing a two-year pattern as a rough patch every time it resurfaces.
Focus on Patterns, Context, and Impact
Traits are not uniformly good or bad. Intensity and role change the verdict.
Caution is an asset in a compliance review and a liability in a fast-moving product sprint. Decisiveness helps a crisis response and hurts a decision that needed three more data points.
So the useful question is never whether someone is a bad person. It is whether an observable behavior, repeated over time, is measurably harming trust, information flow, or delivery. Impact is something you can describe. Character is something you can only assume.
20 Negative Personality Traits and How They Appear at Work
These traits damage trust, communication, and accountability once they become repeated workplace patterns. Each entry names what to watch for and the replacement behavior that addresses it.
Trust and Accountability Problems
Dishonesty. Misstating progress, concealing errors, or claiming credit for someone else’s work. It shows up as a status update marked “on track” for a project that slipped two weeks ago. Once discovered, every future report gets double-checked. Replacement behavior: report bad news early and in specifics.
Blame-shifting. Reframing every failure as someone else’s fault. A missed deadline becomes “design was slow,” never “I did not flag the dependency.” Teams stop raising issues because the conversation always ends in a search for a culprit. Understanding the difference betweenaccountability and responsibility at work makes the correction concrete. Replacement behavior: name your own contribution to the outcome first.
Unreliability. Agreeing to commitments and then missing them without advance notice. The pattern is not the occasional slip; it is the colleague whose deadlines are treated as estimates. Others build hidden buffers into every plan. Replacement behavior: commit to fewer things and renegotiate early when a date is at risk.
Manipulation. Getting outcomes through pressure, selective information, or playing colleagues against each other. It often looks like private side-conversations that contradict what was said in the room. Replacement behavior: make your case once, in the open, to everyone affected.
Entitlement. Expecting promotions, exceptions, or visibility based on tenure rather than contribution. It surfaces as resistance to unglamorous work and irritation when a peer is recognized. Replacement behavior: tie every request to a documented result.
Communication and Relationship Problems
Poor communication. Withholding context, burying decisions in long threads, or failing to listen before responding. The cost is rework: two people build the same thing, or the wrong thing. Replacement behavior: confirm what you heard before acting, and record decisions where the team can find them.
Passive-aggressiveness. Expressing frustration through sarcasm, delayed replies, or conspicuous silence rather than saying the thing directly. Colleagues spend energy decoding mood instead of doing work. Replacement behavior: state the objection plainly, once, to the person who can act on it.
Disrespect. Interrupting, talking over junior colleagues, dismissing roles, or ignoring stated boundaries. It is often defended as directness. Direct feedback targets work; disrespect targets people. Replacement behavior: critique the output, never the person’s competence.
Gossip. Discussing a colleague’s performance or personal life with people who cannot act on it. It feels harmless and functions as a slow leak in team trust, because everyone present learns they are discussed elsewhere too. Replacement behavior: take the concern to the person or their manager, and nowhere else.
Lack of empathy. Making decisions without weighing their effect on the people who absorb them. It appears as a reorganization announced without warning, or a deadline set without asking what it displaces. Replacement behavior: ask what a decision costs the people executing it before finalizing it.
Ego and Control Problems
Arrogance. Rejecting feedback, dominating discussion, and treating disagreement as ignorance. Confidence invites challenge; arrogance shuts it down. Thehidden cost of tolerating arrogance in the workplace shows up in the ideas that never get raised. Replacement behavior: ask one genuine question before defending your position.
Micromanaging. Reviewing, revising, and re-approving work already delegated. The manager becomes the bottleneck, and capable people stop exercising judgment because it will be overridden. Learning how strong managersempower people at work is the direct fix. Replacement behavior: agree on the checkpoint and the standard up front, then stay out until then.
Defensiveness. Treating any feedback as an accusation and answering with justification. The tell is explained before the other person finishes the sentence. Colleagues eventually stop giving feedback, which removes the main source of correction. Replacement behavior: say “let me think about that” and respond the next day.
Unhealthy competitiveness. Treating teammates as rivals, withholding useful information, or undercutting a peer to look stronger by comparison. It converts a team into individuals optimizing separately. Replacement behavior: share the thing that would have given you an edge.
Chronic negativity. Rejecting proposals by reflex and treating cynicism as realism. Useful skepticism names a specific risk and a possible mitigation. Chronic negativity names only doom, and it spreads fast because agreement is easier than argument. Replacement behavior: pair every objection with one workable alternative.
Initiative and Adaptability Problems
Lack of initiative. Doing exactly what was assigned and nothing that was obviously needed. The gap shows in problems seen and left unmentioned. Colleagues carry the difference, and resentment follows. Replacement behavior: raise one thing per week that nobody asked you to look at.
Inflexibility. Repeatedly resisting reasonable change, which delays decisions and makes collaboration harder. It sounds like “we tried that in 2019.” Rigidity is valuable when defining contract terms and costly when the market shifts. Buildingadaptability in the workplace is the counterweight. Replacement behavior: agree to test the new approach once, with a defined review date.
Inconsistency. Changing priorities, standards, or direction without telling anyone. Work gets redone, and the team stops investing effort until the direction holds still. Replacement behavior: announce changes of direction explicitly, with the reason attached.
Impulsivity. Sending the email, committing to the date, or making the call before checking the facts. It reads as decisiveness in the moment and generates cleanup later. Replacement behavior: apply a fixed delay to any irreversible action, even ten minutes.
Chronic procrastination. Delaying work until the deadline forces a rushed, lower-quality version. The damage lands on reviewers and dependent teams who lose their own working time. Replacement behavior: schedule the first thirty minutes of the task on the day it is assigned.
How Negative Traits Affect Teams and Careers
Uncivil and unaccountable behavior carries a measurable cost. In the second quarter of 2026, 61% of U.S. workers reported experiencing or witnessing incivility at work, amounting to roughly 104.6 million uncivil acts per day, according to theSHRM Civility Index.
The same research puts the daily productivity and absenteeism cost to U.S. organizations at about $2.66 billion, with each uncivil act consuming an average of 33.8 minutes of work time. The clearest measure of how much this matters to employees is what they would trade to escape it: 44% said they would accept a pay cut, averaging a 16% reduction in salary, to eliminate incivility from their workplace.
Trust and Psychological Safety
Psychological safety is the shared belief that speaking up will not be punished. Defensiveness, arrogance, and blame-shifting all remove it, because each one teaches the team that candor carries a cost.
Gallup’s research shows the size of the gap: only 28% of U.S. employees strongly agree their opinions count at work, and 29% of detached employees point to a lack of honest communication from leaders, perGallup’s analysis of U.S. employee engagement.
When people stop raising problems, the problems still exist. They just arrive later and cost more.
Collaboration and Decision-Making
Poor communication, gossip, and unhealthy competitiveness all restrict information flow, so decisions get made on partial data. The symptoms are duplicated work, meetings that exist only to re-share what one person already knew, and escalations two colleagues could have settled on directly.
Inconsistency and micromanaging add a different tax. Both make people wait for permission, which slows execution even when nobody is in open conflict.
Performance and Professional Reputation
Reputation at work is built from repetition, not single moments. Reliability, follow-through, and how someone handles being wrong are the traits colleagues remember and describe to others.
That description travels. It reaches promotion conversations, project staffing decisions, and reference calls, often before the person knows it exists.
What Can Contribute to Harmful Workplace Behavior?
Most harmful workplace behavior is not deliberate. Several conditions make it more likely, and none of them excuse the impact:
Sustained stress or burnout. Long hours, unclear expectations, and understaffing shorten patience and reduce self-monitoring.
Absence of feedback. People cannot correct what nobody has described to them. Many colleagues seen as controlling or negative have never been told.
Insecurity about competence or standing. Defensiveness, arrogance, and blame-shifting often protect a fear of being found inadequate.
A culture that rewards behavior. When aggression gets results and civility gets overlooked, the incentive is clear.
Poor role fit. A tendency that fails in one role can succeed in another. The problem may be the seat rather than the person.
Identifying a contributing factor is diagnosis, not permission. Avoid using these factors to assess a coworker’s psychology. You can describe behavior you have seen; you cannot judge someone’s internal state.
How to Change a Recurring Negative Behavior
Workplace behavior changes when a person identifies the pattern, understands its impact, and practices a specific alternative. Broad resolutions to be a better colleague fail. Single, observable behaviors change.
Identify the Pattern and Trigger
Start with evidence you already have rather than a personality assessment. Work through these questions honestly:
What feedback have I received more than once, from more than one person?
Which recurring conflicts involve the same behavior from me each time?
Are colleagues reluctant to bring me problems or involve me early?
What was happening in the minutes before the behavior appeared?
Which situation reliably produces it: deadline pressure, public disagreement, or being corrected?
The last two questions matter most. A trigger is something you can plan for. A trait label is not.
Choose a Specific Replacement Behavior
Use the three-step method: identify the trait, name the impact, practice the opposite behavior.
Working example. The trait is defensiveness. The impact is that teammates have stopped offering suggestions, so problems surface late. The replacement behavior is to answer any critique with a question rather than a justification for the next month.
That specificity is what makes change trackable. “Be less defensive” cannot be observed. “Ask a question before responding” either happened in the meeting or it did not.
Ask for Feedback and Track the Change
Tell one trusted colleague or your manager exactly which behavior you are working on and ask them to flag it when it appears. This works better than general requests for feedback, which usually return reassurance.
Set a cadence. A five-minute check-in every two weeks for three months is enough to see whether the pattern is shifting. Note where the old behavior still wins, because those are the remaining triggers. Behavior under low pressure changes first. Behavior under high pressure changes last.
How Managers Should Address Negative Behavior
Managers carry most of the weight here, and many are struggling. Gallup reported global employee engagement at 20% in 2025, with manager engagement at 22%, down from 31% in 2022, which means the engagement advantage managers once held has largely disappeared, according toGallup’s State of the Global Workplace.
A depleted manager tends to avoid the conversation, and avoided behavior spreads. Practical approaches todealing with difficult coworkers give team members something to use while the manager acts.
Describe Behavior, Impact, and Expectations
Never open with a personality label. “You are negative” invites a debate about identity that nobody wins.
Describe the observable behavior, the effect it had, and the expectation going forward. For example: in the last three planning meetings you rejected each proposal without offering an alternative; two team members told me they stopped contributing ideas; going forward, pair any objection with one option you would support.
Bring specific instances with dates. Vague feedback is easy to dismiss and impossible to act on.
Provide Support and Document Repeated Patterns
Coaching and performance management are different tools. Coaching assumes the person can change with clarity and practice, so give the replacement behavior, the review date, and any training or workload relief that makes it achievable.
If the pattern continues after clear feedback and a genuine chance to correct it, move to documentation: dates, behaviors, business impact, and what was communicated each time. Keep records factual and free of character judgments.
Address the behavior while it is still a coaching conversation. Patterns tolerated for a year become far harder to unwind, and the strongest people on the team usually leave before the problem does.
Final Takeaway
The twenty traits in this guide share one feature: they are patterns, and patterns respond to attention. Naming the specific behavior, understanding who it affects, and practicing a defined alternative moves the needle in a way that broad self-improvement goals never do.
For managers, the same principle applies in reverse. Describe conduct, not character, and address it while it is still small.
If a recurring pattern is holding back your career or straining your team,talk to a PathWise career coach about the specific behavior you want to change and how to measure the shift.
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What Makes a Bold Person? Traits and Examples at Work
August 12, 2026
A bold person acts with courage and confidence when the outcome is uncertain. At work, that usually looks like speaking up in a room where nobody else will, taking a considered risk, owning a mistake in public, or questioning a process everyone has quietly accepted as broken.
Boldness is not the absence of fear, and it is not volume. Someone can feel nervous, prepare carefully, and still choose the harder conversation. That repeated choice is what separates a bold person from a merely loud one.
What Does It Mean to Be a Bold Person?
Bold means willing to act, speak, or decide despite uncertainty or risk. The dictionary synonyms cluster around temperament: daring, fearless, audacious, intrepid, gutsy. Those words describe how boldness feels from the outside. They say very little about how it works.
A more useful definition treats boldness as a behaviour you choose rather than a personality you inherit. Three components show up again and again when people describe a bold colleague. Social assertiveness, or the willingness to state a position in front of people who may disagree. Emotional resilience, or the capacity to stay functional when the response is cold. Venturesomeness, or an appetite for the untested option.
That framing matters because it separates boldness from noise. A person who interrupts every meeting has social assertiveness and nothing else. A bold person pairs the willingness to speak with judgment about what is worth speaking about.
Boldness at work also shows up in three distinct forms. There is boldness of voice, which is saying the unpopular but accurate thing. There is boldness of action, which is starting something before you have formal permission. And there is boldness of ownership, which is naming your own failure before someone else finds it. Most people are comfortable with one of the three and avoid the other two.
Eight Traits of Bold People at Work
Bold people at work tend to share a recognisable set of behaviours. Each one is observable, which means each one can be practised.
Courage under uncertainty. They raise the issue before they have a guaranteed outcome or a supportive audience.
Confidence grounded in preparation. They make a case with evidence rather than volume.
Clarity of purpose. They can explain why a change matters, not only that it should happen.
Considered risk-taking. They accept that some attempts will fail and they size the bet accordingly.
Authenticity under pressure. Their position stays the same when the senior person in the room disagrees.
Accountability for outcomes. They name their own errors early and propose the correction.
A stable moral foundation. Integrity and fairness set the boundary on what they are willing to push for.
Adaptability and a learning mindset. They update their position when the evidence changes rather than defending it out of pride.
Courage and Thoughtful Risk-Taking
The difference between boldness and recklessness is reversibility. Bold people instinctively sort decisions into two categories: the ones you can undo cheaply and the ones you cannot. A pilot project, a trial process, a proposal you can withdraw all sit in the first category, and those deserve a fast, confident push.
Irreversible decisions deserve slower thinking and wider consultation. Recklessness treats both categories the same way. Boldness does not.
Confidence and Social Assertiveness
Confidence is often mistaken for certainty. In practice, the most persuasive bold people say some version of “here is what I think, here is the evidence, and here is what would change my mind.” That last clause is what makes the confidence credible rather than defensive.
Social assertiveness is the delivery mechanism. It is the ability to hold the floor without raising your voice, to finish a sentence when someone tries to talk over it, and to ask the follow-up question everyone else swallowed.
Authenticity, Values, and Accountability
Bold behaviour without a value system is just risk appetite. The colleagues people describe as genuinely bold are usually the ones whose positions are predictable from their principles, which is why the distinction betweenaccountability vs responsibility matters so much here. Responsibility is the task you were assigned. Accountability is the outcome you own, including the parts that went wrong.
That is also whydiscovering and living your values is a practical prerequisite rather than a soft exercise. If you do not know which lines you will not cross, every bold decision becomes a fresh negotiation with yourself under time pressure.
Adaptability and Resilience
Boldness produces more feedback than caution does, and a lot of that feedback is uncomfortable. The trait that keeps bold people employable is the willingness to absorb the correction and adjust. Strongadaptability in the workplace is what turns a rejected proposal into a better second attempt rather than a grudge.
Resilience here is unglamorous. It mostly means being able to have a proposal rejected on Tuesday and raise a revised version on Thursday without treating the rejection as a verdict on your worth.
Examples of Being Bold in the Workplace
Silence at work is far more common than people assume. A 2026 Radical Candor survey of 600 US respondents found thatroughly six in ten employees hesitate to speak up at work, which is why routine candour reads as bold in most organisations.
Bold Actions for Employees
An analyst notices that a weekly report nobody reads consumes six hours of team time. The bold version is not complaining about it. It is tracking the actual hours for a month, checking who opens the file, and bringing a one-page proposal to retire it. The risk is that the report belongs to someone senior. The constructive delivery is framing it as a reclaimed capacity rather than as a criticism of the person who built it.
A junior developer ships a change that breaks a client integration for two hours. The bold action is posting the cause, the timeline, and the fix in the team channel before anyone asks. The risk is looking incompetent. The likely outcome is the opposite, because volunteering a failure signals that you can be trusted with information that is not flattering to you.
An employee asked to take on a fourth project says no, and explains which of the existing three will slip if the answer becomes yes. Setting a boundary with a reason attached is one of the most underused bold moves available to individual contributors.
Bold Actions for Managers and Leaders
Bold leadership means challenging a norm that is producing bad outcomes and staying accountable for what happens next. A manager who kills a legacy process defended by a senior stakeholder is being bold. So is a manager who publicly credits the team member whose dissent changed the plan, because that single act does more to surface future dissent than any survey.
The harder version is protecting a person rather than an idea. When a quiet team member raises an objection and the room moves past it, a bold manager stops and returns to it. Many of the20 qualities of a good leader come down to that kind of small, visible intervention repeated consistently.
Senior leaders face a different risk profile. Their boldness is amplified, so a poorly reasoned position spreads faster and costs more. The corrective is to show the reasoning, name the uncertainty, and invite challenge explicitly rather than assume people will offer it.
Bold vs. Assertive, Aggressive, and Arrogant
These four behaviours are frequently confused, and the confusion is expensive. Someone gets labelled aggressive for being bold, or excuses arrogance by calling it boldness. The difference is intent and delivery, not intensity.
Bold. The intent is to improve an outcome despite uncertainty. The delivery is direct and considered. The effect is that a real problem gets discussed or a change gets tested.
Assertive. The intent is to state a view, need, or boundary clearly. The delivery is respectful and confident. The effect is clarity, with no attempt to move the whole room.
Aggressive. The intent is to win or control. The delivery is forceful, dismissive, or personal. The effect is defensiveness, and the argument stops being about the idea.
Arrogant. The intent is to demonstrate superiority. The delivery is condescending and closed to input. The effect is erosion of trust, which is expensive precisely because it is slow to show up.
Boldness and assertiveness overlap constantly. The clean test for the other two is whether the person is challenging the idea or attacking the person, and whether they can name the conditions under which they would change their mind. Arrogance cannot answer the second question, and thehidden cost of tolerating arrogance in the workplace is that competent people stop contributing long before anyone files a complaint.
When Boldness Helps and When It Hurts
Boldness works when the situation is genuinely unresolved, when you hold information others do not, and when the decision can be tested. It fails when the decision has already been made for reasons you have not asked about, when you are the fifth person to raise the same point, or when your position is a preference dressed up as a principle.
Context also decides how boldness lands. A new hire challenging a strategy in week two is read differently from the same challenge in month nine, not because the argument is weaker but because the credit account is empty. Power dynamics work the same way. A senior person’s bold question is a prompt. A junior person’s identical question can be heard as insubordination, which is a failure of the culture rather than the junior person.
The most common failure mode is not recklessness. It is boldness applied at constant intensity. People who challenge everything spend their credibility on trivia and have nothing left when something important is at stake.
How Psychological Safety Affects Speaking Up
Whether an employee speaks up depends heavily on the environment, not only on individual courage. Psychological safety isthe belief that a team is safe for interpersonal risk-taking, meaning you can ask a question, admit a mistake, or challenge an idea without fear of embarrassment or retribution. Where that belief is absent, silence is a rational choice rather than a character flaw.
The scale of the gap is measurable. Gallup reported in August 2025 that only28% of US employees strongly agree that their opinions count at work. That figure reframes the whole conversation about boldness. If nearly three quarters of people do not believe their input registers, telling them to be braver addresses the wrong variable.
For individuals, the practical implication is to read the environment before you spend courage in it. Watch what happens to the last person who disagreed. For managers, the implication is heavier: employee voice is something you either build conditions for or suppress by accident, and the most reliable signal is what you do in the ten seconds after someone contradicts you.
How to Become Bolder at Work
Boldness scales with practice, and the practice should start small enough that failure is survivable. Ask one clarifying question in a meeting where you would normally stay quiet. Send the follow-up email you have been drafting for three days. Volunteer for the piece of work that is slightly beyond your current skill.
Preparation does most of the heavy lifting. People who look effortlessly bold have usually rehearsed the first sentence, anticipated the two obvious objections, and decided in advance what they will concede. Structuredcommunication skills activities give you a low-stakes place to build that muscle before the meeting that matters.
Reflection closes the loop. After each attempt, note what you said, how it landed, and what you would change. Boldness that never gets reviewed calcifies into a habit of being difficult.
Use a Constructive-Boldness Decision Check
Before you take a bold action, run through seven questions. If you cannot answer them, you are not ready to spend the credibility.
What specific outcome am I trying to improve?
What evidence supports my position?
Who is affected, and have I considered their perspective?
What could go wrong, and how bad is the worst case?
Can this decision be tested cheaply or reversed?
How will I actively invite disagreement?
Am I challenging the idea, or am I attacking the person?
Questions five and seven catch most of the damage. If the decision is reversible and you are attacking the idea rather than the individual, boldness is almost always the right call.
Final Takeaway
Boldness is a set of practised behaviours, not a personality you either have or lack. It works when it is paired with evidence, judgment about reversibility, and enough self-awareness to know when you are challenging an idea versus defending your ego. It fails when it becomes a constant setting rather than a deliberate one. And it is heavily shaped by whether your workplace treats dissent as useful information or as a problem to be managed.
If you want structured support building the confidence to speak up and take smarter risks in your career,explore PathWise membership, which is free at the basic tier, orcontact the PathWise team to talk through your situation directly.
AI Career Planning: 2026 Guide for HR & Job Seekers
August 7, 2026
AI career planning uses artificial intelligence tools to analyze skills, map career options, identify gaps, tailor resumes, prepare for interviews, and recommend learning paths. It is not a decision-making machine. It is a pattern-recognition engine that helps professionals and HR teams see faster what once took months of guesswork.
The shift matters because the labor market is moving faster than traditional career planning can handle. Roles are changing, skills are expiring, and both employees and job seekers need clearer, more responsive ways to navigate what comes next.
This guide explains how AI career planning works in practice, what it does well, where it falls short, and how HR professionals and individual job seekers can each use it to make better career decisions in 2026.
What Is AI Career Planning?
AI career planning is the practice of using generative AI tools, career pathing software, and skills-based platforms to support career decisions at any stage of professional life. The tools range from general-purpose assistants like ChatGPT, Microsoft Copilot, and Google Gemini to specialized platforms that handle resume optimization, applicant tracking system (ATS) analysis, job-description matching, interview preparation, internal talent marketplaces, and personalized learning paths.
What distinguishes AI career planning from a basic job-search tool is scope. A single AI session can map your current skills against a target role, flag the three certifications that appear most frequently in job postings, generate STAR-method interview stories from your work history, and recommend a six-month learning plan, all before your first conversation with a recruiter.
For HR and learning and development (L&D) teams, AI career planning extends further. It can inventory skills across an entire workforce, surface employees ready for internal mobility, identify succession gaps, and generate personalized development plans at a scale no team of managers could sustain manually.
What it cannot do is choose a direction for you. That requires self-knowledge, values, human context, and judgment, things that remain entirely outside the reach of any AI system available today.
Why AI Career Planning Matters More in 2026
Skills Are Changing Faster Than Career Paths Can Keep Up
The World Economic Forum’s Future of Jobs Report 2025 projected that 170 million new roles will be created and 92 million displaced by 2030, producing a net gain of 78 million jobs. More pressingly, nearly 40 percent of skills required on the job are expected to change in that same window.
For most professionals, that means the skills that landed the current role may not sustain the next one. Linear career ladders built around titles and tenure are giving way to skills-based career pathing, where what you can do matters more than what your last job was called.
PwC’s 2026 Global AI Jobs Barometer adds another dimension. New tasks added to AI-exposed roles are 2.5 times more likely to require skills like empathy, judgment, and creativity than the tasks those roles previously held. AI is not making human skills irrelevant. It is making them harder to ignore, and more valuable when present.
AI career planning tools help individuals and organizations track these shifts in real time, rather than waiting for an annual review to discover that a skill set is three years behind the market.
Employees Want Clearer Internal Paths
The conversation about career growth has moved inside organizations. SHRM’s 2026 State of AI in HR Report found that 33.7 percent of HR leaders plan to invest in AI-driven internal mobility or talent marketplace tools within the next twelve months, making it the single top-funded AI category for HR investment. A further 32.9 percent plan to invest in AI career coaching or development guidance.
That investment reflects a real employee need. Workers who cannot see a path forward inside an organization start looking outside it. AI-powered internal talent marketplaces give HR teams a way to show employees concrete next steps: lateral moves, stretch assignments, and emerging leadership roles, before they update their profiles elsewhere.
Job Seekers Are Competing in an AI-Shaped Hiring Market
On the individual side, 70 percent of job seekers now use generative AI to research companies, draft cover letters, and prepare for interviews. More than half use it to write cover letters. At least 36 percent rely on it for writing samples.
That widespread adoption creates a new problem: when everyone submits an AI-optimized resume, polish stops being a differentiator. Specificity, proof, and authentic voice become the things that get noticed. Understanding how to use AI for preparation without producing generic output is now a core job-search skill in its own right.
How HR Teams Can Use AI for Employee Career Development
Map Skills Across the Workforce
One of AI’s clearest advantages in HR is its ability to build and maintain a skills inventory at scale. Rather than relying on job titles and org charts, AI-powered platforms can infer skills from performance data, project histories, certifications, and manager feedback, then match those inferred skills against a standardized skills taxonomy.
This kind of mapping makes workforce planning more precise. Instead of asking “who is available for this project,” HR leaders can ask “who already has the skills this project requires, and who is three months from having them.” The distinction changes how organizations fill roles, develop employees, and build succession plans.
One important caution: skills data ages quickly. In professions affected by AI, the required skill set changes 66 percent faster than in other areas, according to Deloitte’s 2026 Human Capital Trends research. Any skills inventory that is not actively maintained becomes a liability rather than an asset within a short window.
Personalize Learning and Development Paths
Generic training programs fail because they treat a forty-person team as a single learner. AI-powered L&D tools can recommend courses, certifications, project assignments, and mentoring relationships based on an individual employee’s current skills, career goals, and target roles.
This matters because the gap between what organizations offer and what employees need is significant. Deloitte’s 2026 research found that only 8 percent of organizations globally believe they are highly effective at meeting continuous learning needs. Traditional L&D cannot scale fast enough on its own. AI-generated learning recommendations, reviewed and adjusted by managers and coaches, offer a path to personalization without adding headcount.
The key word is “reviewed.” AI can generate a learning plan in seconds. Whether that plan fits the employee’s actual situation, aspirations, and constraints is a judgment call that belongs to a manager or coach, not an algorithm.
Support Internal Mobility and Succession Planning
Internal mobility is one of the highest-leverage applications of AI career planning for organizations. AI tools can identify employees whose current skill profiles align with open roles elsewhere in the organization, flag them as internal candidates, and model what a lateral or upward move would require from a development standpoint.
The results can be substantial. Organizations that have restructured around skills-based internal hiring have reported reductions in external recruitment spending of 30 percent within eighteen months of deployment, according to case data compiled by HR platform research in 2026.
Beyond cost savings, internal mobility improves retention. An employee who sees a path inside the organization is less likely to leave it. AI makes that path visible in a way that manual processes rarely achieve.
Give Managers Better Tools for Career Conversations
Most managers want to support their team members’ development. Few have the time or training to structure those conversations well. AI can help here without replacing the human element.
AI-generated prompts, development-plan templates, and career conversation guides give managers a starting point. A manager preparing for a development conversation might use an AI tool to generate five questions tailored to where the employee is in their career, then decide which ones to use based on what they already know about that person. The AI creates efficiency. The manager provides context, psychological safety, and judgment.
What HR should avoid is letting AI-generated development plans become final documents without a real human conversation around them. When employees sense their career plan was produced by a system and handed to them by a manager who did not really engage with it, trust erodes.
For organizations building structured employee career development programs, combining AI tools with manager coaching and dedicated resources is more effective than deploying either alone. Exploreemployee career development support for HR teams to see how structured programs can complement the AI tools your team already uses.
How Job Seekers Can Use AI for Smarter Career Planning
Identify Realistic Career Options Without Guessing
One of the most useful things AI can do for a job seeker is compare a current skill set against a target role and identify the gap honestly. Rather than deciding between three roles based on gut instinct, a professional can prompt an AI assistant to compare their experience against each role’s requirements and flag the most realistic transition path.
A useful starting prompt: “Here is my work history. Here are three roles I am considering. Compare my current skills to the requirements of each role, identify which transition is most realistic in the next twelve months, and explain what is missing.” The AI’s response is a starting point, not a final answer. Verify it against actual job postings and, where possible, conversations with people already in those roles.
Find Skill Gaps Without Relying on a Single Job Posting
A single job description reflects the preferences of one hiring manager on one day. Patterns across fifteen to twenty postings for the same role reflect what the market actually values.
AI tools can analyze multiple job descriptions at once and extract repeated skills, tools, certifications, and responsibilities. Running that analysis separates must-have requirements from nice-to-have preferences, which gives a job seeker a much more reliable learning priority list than any individual posting can provide.
That list becomes the foundation for a learning plan: courses, projects, or portfolio work aimed at the skills that appear most frequently, not the ones that looked most impressive on a single listing.
Improve Resumes Without Sounding Like Everyone Else
AI can tailor resume language to a specific role’s requirements, flag where experience is undersold, and surface keywords that ATS systems prioritize. Used well, it makes a resume more relevant to the role it is targeting.
The risk is homogenization. When a large share of applicants use the same tools to optimize the same resume sections with the same suggested language, output converges. Hiring managers and recruiters recognize this pattern quickly.
The antidote is specificity. AI-generated language should be a scaffold, not a final draft. Replace generic suggested phrases with your actual numbers, context, and outcomes. “Improved team productivity” becomes “cut weekly reporting time from six hours to ninety minutes by building a shared tracking system.” That specificity cannot be faked by an AI tool because it comes from lived experience.
For personalized support reviewing resumes against real job requirements,career services and assessments at PathWise pair expert review with structured feedback that AI alone cannot provide.
Prepare Stronger Interview Stories
AI interview preparation tools can generate lists of likely questions for a specific role, help structure STAR-format (Situation, Task, Action, Result) responses, and offer feedback on clarity and completeness. This kind of systematic preparation is genuinely useful, especially for candidates who have not interviewed recently.
Where AI falls short is nuance. A human coach, mentor, or trusted peer can tell you when a story sounds rehearsed, when you are underselling the significance of a result, or when your answer addresses the wrong concern. AI feedback improves structure. Human feedback improves impact.
Research Employers Without Trusting AI Summaries Blindly
AI can quickly synthesize a company’s public strategy, recent announcements, industry position, and culture signals. That is a useful starting point for interview preparation and evaluating whether a role fits.
The limitation is that AI summaries reflect publicly available information, which may be incomplete, outdated, or carefully managed. Glassdoor reviews, direct conversations with current or former employees, and informational interviews add the candid perspective that press releases rarely contain. Use AI to orient yourself, then go deeper through human sources.
What AI Cannot Do in Career Planning
Know Your Values, Tradeoffs, or Purpose
Career decisions involve questions that AI cannot answer: What am I willing to sacrifice for this role? Does this path align with the kind of life I want to build? What would I regret not trying? These are questions of self-knowledge, not pattern recognition.
Assessments like CliftonStrengths, DISC, and TypeFinder complement AI career planning by giving people structured language for their strengths, work preferences, and interpersonal patterns. They work because they help individuals understand themselves, not because they optimize for market fit. The two approaches address different questions and work best when used together.
When the career question is about values alignment, purpose, or navigating a major transition,career coaching and resume support through PathWise provides the human perspective that makes AI insights actionable in a specific life context.
Replace Coaching or Honest Feedback
AI generates options. People help interpret them. That distinction matters most in the situations where career decisions carry the most weight: a major pivot, a difficult promotion conversation, a return to work after a gap, or a leadership transition that is not going as planned.
Career coaches, mentors, and managers bring something AI cannot replicate: they know the person, not just the profile. A coach who has worked with a client for three sessions understands the fears, constraints, and motivations that sit behind the career question. That context changes what guidance is actually useful.
Avoid Reinforcing Bad Assumptions
AI systems reflect the data they were trained on. Job-market data encodes historical patterns, including historical biases. An AI tool that recommends career paths based on what similar professionals have done before may steer users toward well-worn tracks while undervaluing unconventional but viable options.
There is also the hallucination problem. AI can state inaccurate information with full confidence. Any specific claim an AI makes about a company, a role requirement, a salary benchmark, or an industry trend deserves verification through a named, current source before being acted on.
Risks HR Teams Should Actively Manage
Bias, Privacy, and Transparency
AI systems trained on historical hiring and promotion data can reproduce the patterns in that data, including inequities. An internal mobility tool that draws on past promotion decisions will reflect whoever tended to get promoted before, which may not reflect who should get promoted next.
Employees also have a right to understand when AI is being used to evaluate or recommend them and what data informs those recommendations. Unexplained algorithmic decisions about career opportunities can damage trust faster than any other HR misstep. Clear AI governance, documented use cases, and straightforward communication are not optional features; they are the foundation that makes AI career tools workable at scale.
Over-Automation of Employee Development
AI should accelerate human judgment, not replace it. A career development system that produces AI-generated plans and assigns them to employees without a manager conversation has not improved development. It has made it faster and less personal.
Employees are not skill tags. The person who appears in a workforce planning database as “Python, data visualization, project management” is also navigating a family situation, a difficult manager, a professional aspiration that has not yet made it into any HR system, and a confidence level that may not match their paper qualifications. None of that is in the data. All of it affects what support will actually help.
Uneven Access to AI Tools and Literacy
Some employees will adopt AI tools quickly. Others will not, either because they lack familiarity, confidence, or access to the same information about what tools exist and how to use them. If organizations deploy AI career planning support without training and shared guidance, they risk creating a two-tier system inside the same workforce, where access to AI advantage becomes another form of inequity.
HR teams that want AI to contribute to internal mobility and retention should treat AI literacy as part of the learning and development offering itself, not a prerequisite the employee is assumed to arrive with.
A Practical AI Career Planning Framework
This five-step framework applies to both individual job seekers and HR teams building employee development programs. The sequence matters: starting with the goal, not the tool, produces better outcomes.
Step 1: Define the career direction before opening any tool. The question you are trying to answer shapes everything. Promotion, industry pivot, skills growth, job search, leadership development, and retention risk each require different approaches. Name the decision first.
Step 2: Map current skills and strengths. Use self-reflection, performance feedback, formal assessments, and AI-supported skills analysis together. Include both technical skills and the human skills: judgment, communication, adaptability, and leadership, which PwC’s 2026 research identifies as increasingly rewarded as AI absorbs routine work.
Step 3: Compare target roles and future skill demand. Analyze job descriptions, internal role postings, and industry reports. Look for repeated patterns, not single data points. AI can accelerate this comparison; the interpretation still requires a human.
Step 4: Build a learning and experience plan. Include courses, certifications, projects, mentoring, and stretch assignments. For organizations, connect this to internal mobility pathways. For individuals, connect it to a focused, targeted job search rather than a high-volume application approach.
Step 5: Review progress with a human. AI can update a career plan. A coach, manager, or mentor helps determine whether it still fits the actual situation. Schedule that conversation regularly, not only when the plan was first built.
How HR Professionals Can Build AI Into Career Development Programs
Create Clear Guardrails First
Define which AI tools are approved, what employee data they can access, and what types of recommendations require human review before action. Clarity here is not bureaucracy. It is what makes adoption credible and sustainable. SHRM’s 2026 research found that 57 percent of HR professionals in AI-regulated US states are unaware of the policies governing their AI use in hiring. That gap creates legal and trust risks that governance frameworks exist to prevent.
Train Managers to Use AI as a Coaching Aid
The manager who uses AI-generated prompts to prepare for a development conversation and then actually listens in that conversation is using AI well. The manager who reads an AI-generated plan to the employee during the meeting is not.
Providing managers with prompts, templates, and structured guides works best when it is paired with training on what good career conversations look like. The goal is better questions, not outsourced answers.
Give Employees Access to Structured Resources That Work Together
AI-generated recommendations work better when they point employees toward real resources: courses, coaching, assessments, peer communities, and human advisors, rather than ending at the recommendation itself. Organizations that combine AI-enabled insight with structured career resources and human coaching create a development ecosystem rather than a tool deployment.
Explorecareer resources for organizations and HR professionals to see how layered career development support, combining courses, coaching, assessments, and structured content, functions as a system rather than a collection of standalone offerings.
Measure Outcomes Beyond Tool Adoption
Usage metrics tell you who opened the platform. They do not tell you whether anyone’s career moved forward. Track internal mobility rates, retention among employees who engaged with career development tools, learning completion linked to stated goals, and the quality of manager development conversations over time. Those are the indicators that connect AI investment to actual workforce outcomes.
How Job Seekers Can Stand Out in an AI-Driven Market
Use AI for Targeted Preparation, Not Mass Applications
Sending a hundred AI-optimized applications is still sending a hundred applications most of which will be ignored. The math of a high-volume job search has not changed just because AI made it faster to produce more applications.
A focused approach produces better results: fewer applications, each with a genuine case for fit. AI is most valuable for preparation: understanding the role deeply, tailoring the resume meaningfully, and practicing interview answers until they are specific and confident. It is not a tool for scaling a spray-and-pray approach.
Show Proof That AI Cannot Fake
Portfolio work, specific quantified achievements, and work samples carry more weight as AI-generated language becomes common. Skills-based hiring is accelerating partly because it gives employers a way to evaluate candidates beyond the resume, which increasingly reflects what AI suggests rather than what the candidate actually did.
If you can show the work, show it. Projects, case studies, before-and-after results, and concrete examples of judgment in complex situations are things AI cannot produce on your behalf.
Build Real Human Relationships
Networking, informational interviews, referrals, and recruiter relationships still drive a significant share of hiring decisions. AI can help draft outreach, prepare talking points, and research contacts before a conversation. The relationship that results from that conversation is yours to build or neglect.
The professional who uses AI to prepare well and then shows up authentically will outperform the one who automates the outreach and expects the relationship to form on its own.
Develop AI Literacy and Human Skills Together
PwC’s 2026 research found that AI-exposed entry-level roles are now seven times more likely to require traditionally senior-level skills such as judgment and leadership than equivalent roles were before. Learning how to use AI tools fluently matters. So does developing the judgment to know when not to use them, and the communication and adaptability skills that AI cannot replicate.
Career development in 2026 is not a choice between AI literacy and human skills. Both are required, and neither is sufficient without the other.
When Career Coaching Belongs Alongside AI
AI is well-suited for research, pattern recognition, and initial skill mapping. It is poorly suited for the moments when career decisions carry real stakes.
A career coach belongs in the conversation when you are making a major decision: an industry pivot, a promotion path, a return to work after a gap, or a leadership transition where the cost of guessing wrong is high. A coach also helps when AI gives you too many options and you need someone who knows you to help narrow them. And a coach provides accountability that AI cannot: the difference between having a plan and following through on it is often a relationship, not a document.
Whether you are an individual navigating a career crossroads or an HR team designing a scalable development program,career coaching and resume support through PathWise bridges the gap between AI-generated insight and the human judgment required to act on it.
AI Makes Career Planning Faster. People Make It Meaningful.
AI career planning is real, it is useful, and it is changing how both organizations and individuals approach career growth. It can compress weeks of career research into an afternoon, surface internal talent that would otherwise go unrecognized, and give job seekers preparation tools that were not available to most people even five years ago.
But it is not a replacement for self-knowledge, coaching, honest feedback, or the human relationships that careers are actually built on. The best outcomes in 2026 will come from combining AI-driven insight with deliberate human action.
For HR teams: build AI into a broader employee development system, not as a standalone tool deployment. Pair it with coaching, structured resources, manager training, and clear governance.
For job seekers: use AI to become more focused and better prepared, not more generic and high-volume.
First-time manager coaching is structured, ongoing support that helps newly promoted leaders build the habits, judgment, and confidence they need to manage people effectively. Unlike a training workshop, coaching focuses on real workplace situations: the delegation conversation that went sideways, the feedback a new manager keeps postponing, the team dynamic that no one warned them about.
For HR professionals, coaching is one of the most practical tools available for supporting the individual contributor-to-manager transition. It bridges the gap between what a new manager learns in orientation and what they actually need to do on Monday morning.
Why First-Time Managers Struggle After Promotion
Promoting your strongest individual contributor is a reasonable decision. It rewards performance and fills a gap. The problem is that the skills that make someone an outstanding individual contributor (personal output, deep expertise, self-reliance) are not the skills that make someone an effective people leader.
A substantial preparation gap exists: aCenter for Creative Leadership study found that almost 60% of first-time managers reported receiving no training when they entered their first leadership role. Separately,Gartner found that 40% of managers with two years or less of experience struggled to support their teams; these findings do not establish a 60% failure rate within 24 months.
Gallup’s research makes the business case plain: managers account for at least 70% of the variance in employee engagement scores across business units. When a first-time manager struggles, the impact is not limited to that one person. It ripples through their entire team, showing up in turnover, missed performance expectations, and disengaged employees.
DDI’s 2024 coaching analysis found that 85% of HR respondents said coaching skills would be critical for leaders to develop in the next three years. It also found that 31% of frontline leaders wanted more coaching from their managers; DDI’s “nearly 40%” figure refers more broadly to leaders reporting inadequate coaching.
The transition is genuinely difficult. New managers must shift from “I succeed through my own work” to “I succeed by enabling others.” That identity change does not happen automatically, and it cannot be covered in a two-hour orientation session.
The Common Friction Points in New Manager Transitions
Most first-time managers run into the same set of challenges, regardless of industry or organization size. Understanding these friction points helps HR design coaching that addresses real problems rather than abstract leadership concepts.
Letting go of individual work. High performers are often promoted because they do things well. Their instinct in a new management role is to keep doing the work themselves, because it feels faster and safer. Delegation requires trust, clear communication, and a willingness to let someone else’s approach be “good enough.” That takes practice.
Giving feedback. New managers frequently know when something is not working but avoid addressing it directly. The feedback conversation feels risky. They do not want to damage the relationship or seem critical, especially when managing former peers. Without coaching, avoidance becomes a habit, and performance problems compound.
Managing former peers. This is one of the most uncomfortable parts of the transition. Yesterday’s colleague is now an employee. Boundaries shift. Friendships get complicated. New managers need support navigating these changed relationships with both consistency and care.
Setting expectations. Many new managers assume their team already knows what is expected. They do not clearly define goals, decision rights, or communication norms. When those expectations go unstated, confusion follows.
Handling conflict. Most new managers have no training in conflict resolution. When team tension surfaces, they either overreact or avoid it entirely. Neither response builds team trust.
How Coaching Differs from Training and Mentoring
HR teams often have training programs in place for new managers. Those programs matter. But training alone rarely changes behavior, and confusing coaching with training leads to underinvestment in both.
Training teaches core concepts, tools, and processes. A new manager needs to understand the performance review process, know how to document a performance issue, and be clear on company HR policies. Training delivers that foundational knowledge efficiently and at scale. It is a necessary starting point.
Mentoring offers experience-based guidance from someone who has been in a similar role. A mentor can share organizational context, offer informal advice, and help a new manager navigate unwritten rules. This is especially valuable in the first few months, when a new manager is still learning how the organization works.
Coaching is different from both. A coach does not give answers or share personal experience. Instead, coaching helps the manager reflect, practice, make better decisions, and build the habits that translate training into real leadership behavior. It works on the specific situation the manager is in right now: the difficult conversation they need to have tomorrow, the delegation challenge they have been avoiding, the team dynamic that is starting to create problems.
The strongest new manager support programs combine all three. Training covers knowledge. Mentoring covers context. Coaching covers application.
One more distinction worth making: coaching should be developmental, not remedial. Too many organizations only introduce coaching after a manager is already struggling, which makes it feel like a consequence rather than a resource. When coaching is offered as a standard part of the leadership transition, new managers are more likely to engage with it honestly and use it well.
The Coaching Topics New Managers Need Most
Coaching works best when it is grounded in real situations. The topics below represent the areas where first-time managers most consistently need structured support. HR can use these as a curriculum map, with the understanding that priorities will vary based on role, team size, and business context.
Role Clarity and Expectations
Many new managers start their role without a clear picture of what success looks like in the first 30, 60, or 90 days. Coaching can help them answer specific questions: What decisions are theirs to make? What requires escalation? What are the team’s current performance goals, and how does the manager’s role connect to them?
HR plays a critical role here too. Aligning the new manager, their direct leader, and the team on expectations early reduces the confusion that causes many early failures.
Delegation and Prioritization
New managers frequently try to keep too much work. They are used to being the person who executes, and handing things off feels risky. Coaching provides a space to work through questions like: What should only you handle? What work can be delegated for team development? What does “done well enough” actually mean for each type of task? How do you follow up without micromanaging?
This topic connects directly to workload sustainability. A new manager who cannot delegate will burn out, and their team will not grow.
Feedback and Difficult Conversations
The ability to give specific, timely, respectful feedback is one of the most important management skills, and one of the hardest to develop without practice. Coaching helps new managers prepare for real conversations: an underperformer who needs a direct message, a team member who missed a deadline, a peer dynamic that is creating friction.
Role-play is a particularly effective coaching format for this topic. Practicing a difficult conversation before it happens reduces anxiety, improves clarity, and gives the manager a chance to get feedback on their approach before the stakes are real.
Communication and Trust Building
First-time managers are closely observed by their teams. Every interaction sets a tone. Coaching covers the mechanics and the meaning of management communication: how to run one-on-ones effectively, how to listen rather than just respond, how to adapt communication style to different team members, and how to stay consistent between what is said and what is done.
Psychological safety, the condition where team members feel safe to speak up, ask questions, and acknowledge mistakes, is built or eroded through these early management behaviors.
Coaching Their Own Employees
One of the most underserved coaching topics for new managers is how to coach. DDI’s research found that coaching skills are among the most critical competencies HR leaders expect leaders to develop. Yet most new managers have never been shown how to ask a good coaching question, support a direct report’s development goals, or avoid the trap of solving every problem for their team.
First-time manager coaching should include at least some focus on helping new managers understand what it means to lead with a coaching mindset. This has downstream effects on team development, employee retention, and the manager’s own effectiveness over time.
Self-Awareness and Leadership Style
Assessments can be a useful tool when used well. CliftonStrengths, DISC, 360 feedback, or leadership-specific assessments can help a new manager understand their natural tendencies and blind spots. The goal is not to label the manager but to give them useful information for reflection. A coach helps translate assessment results into specific behavioral commitments rather than abstract self-knowledge.
How HR Can Structure Coaching for First-Time Managers
The format of coaching matters as much as the content. HR teams can choose from individual coaching, group coaching, peer coaching, or a blended model. The right choice depends on the manager’s situation and the organization’s resources.
Start Before or Immediately After Promotion
Waiting until a manager is already struggling is a missed opportunity. Ideally, HR identifies likely first-time managers before a promotion is finalized and introduces coaching as part of the transition process.
Pre-promotion coaching topics include: motivation for moving into management, realistic expectations about the role, self-awareness about strengths and gaps, and readiness for people leadership. For high-performing individual contributors, this kind of early conversation can prevent the most common early failures.
If pre-promotion coaching is not feasible, the first 30 days after promotion are the highest-leverage window. That is when new managers are most open to input and most in need of structure.
Build a 90-Day Coaching Plan
A structured 90-day plan gives both the new manager and HR a shared framework for the early transition. Here is a practical model:
Days 1-30: Role and Relationship Clarity Coaching focus: understanding expectations, meeting the team as a manager, establishing one-on-one rhythms, identifying early risks or concerns. Practice assignment: draft a listening plan for the first month. What do you need to learn, and from whom?
Days 31-60: Core Management Habits Coaching focus: delegating one meaningful responsibility, preparing for a feedback conversation, setting team priorities, managing time and boundaries differently than before. Practice assignment: hold one structured delegation conversation and reflect on how it went.
Days 61-90: Accountability and Confidence Coaching focus: addressing performance concerns early, navigating conflict, asking for feedback from the team and from their own leader, adjusting habits based on what is working and what is not. Practice assignment: run a brief team retrospective or pulse conversation to get structured input from direct reports.
New managers should leave each coaching session with one concrete behavior to practice before the next session. Reflection without action does not build habits.
Use Group Coaching for Shared Challenges
Group coaching works well when multiple new managers are navigating similar transitions at the same time. A cohort of newly promoted managers can work through common challenges together (delegation, feedback, conflict, communication) in a structured, facilitated format.
SHRM notes that group coaching creates a safe place for new managers to ask questions and learn from their peers. That shared context reduces the isolation that many first-time managers feel and normalizes early-stage struggles.
Effective group coaching typically includes eight to twelve participants, meets monthly, focuses on a specific topic each session, and builds in real scenario practice. This format is scalable and lower-cost than individual coaching, making it a practical option for organizations with limited budgets.
Use Individual Coaching for Sensitive or Complex Situations
Some situations require the privacy and depth of one-on-one coaching. These include confidence issues, difficult team dynamics, stakeholder conflict, performance concerns about a specific team member, or preparation for a stretch assignment or promotion conversation.
Individual coaching gives the manager space to work through the specifics of their situation without concern for how it looks to peers.PathWise’s career and leadership coaching offers personalized support with clear coaching objectives, progress evaluation, and optional assessments, well suited for new managers navigating complex or high-stakes transitions.
Pair Coaching with Mentoring and Direct Leader Support
Coaching is most effective when it sits inside a broader support structure, not as the only resource a new manager has. A practical model for HR to design around is a support triangle:
The coach focuses on reflection, skill application, and working through real situations. The mentor provides organizational context, navigational wisdom, and informal perspective. The direct leader is responsible for expectations, timely feedback, and accountability.
HR’s role in this model is to make sure each layer is in place and that responsibilities do not overlap or cancel each other out. A new manager who has all three types of support is significantly better positioned than one who has only training materials and a well-meaning manager who is stretched too thin.
HR’s Role in Making Coaching Scalable
Individual coaching relationships are valuable. But an HR team responsible for developing multiple new managers at once needs more than a case-by-case approach. The goal is a flexible, repeatable system.
Create a Manager Coaching Playbook
A coaching playbook does not need to be complicated. It should answer: Who is eligible for coaching and when? What is the expected cadence of sessions? What is the boundary of confidentiality? What topics are in scope? How does HR receive feedback on whether the program is working?
Documenting these answers reduces confusion, sets expectations with both managers and coaches, and makes the program easier to sustain as the organization grows.
Train Senior Leaders to Reinforce Coaching
Coaching will not hold if senior leaders model different behaviors. If a manager’s boss rewards individual heroics over team development, delegation will feel risky. If no one in leadership models feedback conversations, new managers will not prioritize them either.
HR can work with senior leaders to ensure they actively reinforce what coaching is building: delegation, regular one-on-ones, direct feedback, and giving new managers room to learn from mistakes.
Give New Managers Tools They Can Use Immediately
Alongside coaching, new managers benefit from practical tools they can reach for in the moment: a one-on-one meeting template, a feedback conversation guide, a delegation checklist, a 30-60-90 day planning worksheet. These tools extend coaching into everyday practice and reduce the “now what do I actually do?” anxiety that many new managers feel.
Connecting coaching to broadercareer development resources for HR teams ensures that new manager development is part of a coherent employee development system rather than a standalone intervention.
How to Measure Whether Coaching Is Working
HR teams are often asked to justify the investment in coaching. The good news is that coaching produces measurable signals at multiple levels, even if direct ROI calculations require careful interpretation.
Manager-Level Measures
Track self-reported confidence before and after coaching, completion of development goals, attendance and engagement in coaching sessions, feedback from the manager’s own leader, and 360 or pulse feedback from their team where appropriate. These signals tell you whether the individual manager is progressing.
Team-Level Measures
Track employee engagement or pulse scores within the coached manager’s team, team retention rates, internal mobility, performance consistency, and the frequency of escalations to HR. These signals tell you whether the manager’s development is translating into better team experience. Be careful not to over-attribute team outcomes to coaching alone, as many variables are at play.
Program-Level Measures
Track overall participation rates, promotion success rates among coached managers, time-to-confidence (which can be assessed through self-report or manager feedback), manager retention in the 12 to 24 months after promotion, and common themes emerging across coaching cohorts. Patterns across cohorts can also inform improvements to training content, onboarding, and manager development planning.
Research oncareer coaching and employee retention consistently shows that structured development support improves both manager effectiveness and retention. Coaching is not a cost. It is an investment in the people who most directly shape employee experience.
Common Mistakes HR Should Avoid
Even well-intentioned coaching programs fail when the design misses a few key points.
Waiting until a manager is struggling. Late coaching can feel punitive, like something reserved for people who are not doing well. Coaching offered early, as a standard part of leadership transition, normalizes it and increases honest engagement.
Treating coaching as a replacement for training. New managers still need foundational training on company policies, performance processes, compliance requirements, and core management skills. Coaching is not a substitute. It helps apply what training teaches.
Leaving the new manager’s leader out of the loop. If the direct leader is not setting clear expectations, giving timely feedback, and reinforcing development goals, coaching is working against a headwind. HR should treat leader support as a shared responsibility, not delegate it entirely to the coach.
Offering content without practice. New managers do not need more information. They need repetition, reflection, and real-world application. Coaching that stays in the abstract, talking about feedback without practicing it or discussing delegation without making a real commitment, will not produce behavior change.
Sample First-Time Manager Coaching Plan
Here is a practical framework HR teams can adapt:
Month 1: Clarify the Role Coaching focuses on understanding expectations from the manager’s leader, meeting team members individually, establishing a regular one-on-one rhythm, and identifying early risks. Practice assignment: draft a team communication plan or a first 30-day listening tour.
Month 2: Build Core Management Habits Coaching focuses on delegating one meaningful piece of work, preparing for a feedback conversation, setting team priorities, and discussing time management and boundaries. Practice assignment: hold one structured delegation conversation and reflect on the outcome.
Month 3: Strengthen Accountability and Confidence Coaching focuses on addressing any performance concerns early, navigating conflict that has surfaced, asking for feedback from both the team and the manager’s own leader, and adjusting leadership habits based on what is working. Practice assignment: run a team retrospective or brief pulse conversation.
Months 4-6: Deepen Leadership Effectiveness Coaching focuses on team development, stakeholder management, learning how to coach direct reports, and setting longer-term manager development goals. Practice assignment: build a development plan for one direct report.
Build Better Managers Before Problems Escalate
First-time managers do not need to figure it out alone. They need a structured support system that turns leadership concepts into daily habits, before the pressure builds and the team starts to feel the gap.
HR’s role is to build that system. Training covers foundational knowledge, coaching handles real-world application, mentoring provides organizational context, and direct leader support creates accountability. When those pieces work together, newly promoted managers are far more likely to build the confidence, competence, and team relationships that make them effective.
For HR teams looking to build stronger new manager development programs,PathWise’s support for organizations and HR professionals offers career development resources, structured learning, and practical tools designed to help employees grow at every stage of their careers. Individual new managers ready to accelerate the transition can explore
Early career development programs are structured support systems for students, recent graduates, interns, and junior employees in the first few years of work. They combine learning, coaching, mentorship, and feedback into a deliberate framework that helps people build the skills and direction they need to grow.
These programs serve two audiences at once. For employers, they reduce turnover and build a more capable internal talent pipeline. For universities, they help students and alumni move from campus to career with greater confidence and clarity. The most effective programs bridge both sides of that transition.
Who Counts as Early Career?
“Early career” covers more ground than most program managers assume. It includes current students in internship or co-op roles, recent graduates entering the workforce for the first time, junior employees in their first two to three years at a company, alumni returning to work or making early pivots, and career changers who are new to a specific field or industry.
Eligibility should follow program goals, not age or graduation year. A 35-year-old entering a new field for the first time has early career needs. A recent graduate in a senior-facing role may not. Define the audience by where participants are in their career journey, not when they were born.
Why Early Career Development Matters Now
Engagement and retention are urgent business problems. According to Gallup’s State of the Global Workplace: 2026 Report, global employee engagement fell to 20% in 2025, its lowest level since 2020, with lost productivity estimated at $10 trillion. Manager engagement fell from 27% in 2024 to 22% in 2025.
Early career employees absorb this most directly. Early-tenure attrition is a material risk: Work Institute’s 2025 Retention Report estimates that as much as 40% of overall employee turnover occurs during the first year of employment.
InWork Institute’s 2025 Retention Report, career was the largest reported category of 2024 departures (18.9%), followed by work-life balance (11.9%) and management (9.7%); total rewards accounted for 8.2%.
On the university side, employers increasingly expect graduates to arrive with more than academic knowledge. The National Association of Colleges and Employers (NACE) updated its Career Readiness Competencies framework in December 2025, defining career readiness as the foundation from which college-educated talent can demonstrate the core competencies needed for workplace success and lifelong career management.
The eight NACE competencies are career and self-development, communication, critical thinking, equity and inclusion, leadership, professionalism, teamwork, and technology.
LinkedIn’s 2025 Workplace Learning Report adds that career progress is the number one motivation for employees to learn. When that progress stalls, they leave. Organizations classified as career development champions deployed 33% more career development practices than peers with less mature programs, and were 42% more likely to be frontrunners in AI adoption.
Set Goals Before Choosing Activities
The most common mistake in early career program design is leading with activities. A mentorship program, a speaker series, and a rotation schedule are means to an end. Program design should start with outcomes, not programming.
Before choosing any activity, answer two questions. First, what does the organization need from this cohort in six months? In two years? Second, what does the participant need to feel capable, confident, and committed?
Outcome Goals for HR and L&D Teams
Employers should tie program goals to measurable business results. Common targets include reducing time-to-productivity for new hires, increasing retention at the six-month and two-year marks, improving readiness scores before promotion decisions, building a more diverse internal pipeline for management roles, and reducing dependence on external hiring by increasing internal mobility.
Many HR teams now combine structured learning with individual development planning to align employee growth with organizational skill gaps. For a practical framework on this approach, theskills-based career development model provides a useful starting point for connecting participant growth to business capability goals.
Outcome Goals for University Career Services
Career services teams face different pressures. Their goals typically center on improving career readiness scores and self-efficacy for graduating students, increasing employer placement rates and alumni employment outcomes, strengthening employer partnerships and alumni mentoring networks, and scaling career advising beyond one-to-one appointments.
Build the Core Program Architecture
Once goals are set, the structure follows. Strong early career development programs combine five core components. The weight of each depends on the audience and program length, but all five should appear in some form.
Career Readiness Curriculum
The curriculum answers one question: what do participants need to know and be able to do? For employers, this maps to technical skills, company-specific knowledge, and core professional competencies. For universities, the NACE framework provides a ready structure.
Effective curricula go beyond one-time workshops. They sequence learning across the program timeline so skills build on each other. Communication and professionalism come early. Decision-making, self-advocacy, and leadership concepts come later, when participants have enough workplace context to apply them.
Coaching and Career Navigation
Early career employees often know what they want to do next week. They rarely know what they want in five years, or how to get there. This is the gap that careercoaching fills.
Career coaching helps participants understand their strengths, articulate their interests, and map available options to real career paths. Assessments used early in a program give both the participant and their manager useful data about working style, values, and development priorities. Without this layer, many early career employees drift rather than grow.
Mentorship and Peer Networks
Mentorship provides something curricula cannot: access to lived experience. A mentor who navigated a similar transition can reduce the anxiety of uncertainty and give concrete advice that no training module can replicate.
Effective mentorship in early career programs is structured, not accidental. It includes clear expectations, a consistent meeting cadence, and conversation guides that keep discussions productive. Peer cohorts add a second layer, connecting participants with colleagues who share similar challenges and can hold each other accountable.
Both matter for inclusion. Underrepresented talent often lacks access to informal networks and senior sponsors. Structured mentoring relationships reduce that gap in a way that organic networking cannot.
Manager Enablement
Programs often fail not because the curriculum is wrong, but because managers are unprepared to support it. A participant who attends a skills workshop on Monday and has no follow-up conversation with their manager by Friday will not retain or apply what they learned.
Manager enablement means giving supervisors the tools they need to be active participants in development. This includes check-in guides for development conversations, prompts for structured feedback, guidance on scoping stretch assignments, and clear expectations about their role in the program. When managers are prepared, learning transfers. When they are not, it stalls.
Experiential Learning
Early career employees learn by doing. Case studies and lectures build awareness; projects and rotations build capability. Programs that include real work, such as cross-functional assignments, capstone projects, job shadowing, or presentations to senior leaders, produce stronger skill development and higher engagement.
Stretch assignments are particularly effective. They signal trust, create visible accomplishment, and give participants something concrete to discuss in future career conversations.
Sequence the Learning Journey
Most programs run better when they follow a deliberate arc rather than offering disconnected activities month to month.
Phase 1: Onboarding and Belonging (weeks one through four). Start with orientation, expectations, manager alignment, and peer connection. This phase is about reducing anxiety and establishing psychological safety. Early wins matter here: small, achievable tasks build confidence and signal to participants that they belong.
Phase 2: Skills, Feedback, and Exploration (months two through six). Introduce career courses, assessments, coaching sessions, and structured feedback conversations. This is where most of the curriculum runs. Participants should be actively exploring what they are good at, what they enjoy, and how those connect to potential paths inside the organization.
Phase 3: Mobility and Next-Step Planning (month six onward). Shift focus to career path conversations, internal mobility options, individualized development plans, and longer-horizon goal setting. For university programs, this phase often involves alumni engagement, employer connections, and transition support for students approaching graduation.
Tailor the Program by Audience
For HR and L&D Professionals
Employer-run early career programs benefit most from a blended delivery model: self-guided digital resources, cohort learning events, live coaching, manager guides, and periodic pulse surveys. This structure scales without requiring a full-time program manager for every cohort.
The business case should be assessed with organization-specific retention and mobility outcomes. InLinkedIn’s Workplace Learning Report 2025, career-development champions were more likely to be confident in their ability to retain qualified talent (67% versus 50% among other respondents), though this association does not establish a fixed retention rate for development or mentorship programs.
Linking program participation to measurable outcomes, such as retention rate, internal mobility, and promotion readiness, gives HR leaders the data they need to sustain budget support year over year.
Career services teams often run lean. A single advisor may be responsible for hundreds of students and alumni simultaneously. Scalable resources such as articles, assessments, career courses, and online events extend the team’s capacity without adding headcount.
The university-to-employer transition is one of the most disorienting career shifts a person navigates. Students know how to succeed academically; they are far less certain how to succeed professionally. Career readiness programming that runs throughout a student’s enrollment, not just in the final semester, produces significantly better outcomes than last-minute placement support.
Some of the most effective early career programs live at the boundary between campus and employer. These partnerships may include employer panels embedded in career services events, alumni mentoring networks that connect graduates with current students, co-branded internship readiness workshops, and structured post-graduation transition support.
Both sides benefit. Employers get earlier access to prepared talent. Universities demonstrate tangible career outcomes to prospective students and accreditors. The shared investment produces stronger results than either party achieves working alone. The broader strategy offuture-proofing employee careers applies equally to how universities prepare students for the workforce.
Measure Program Success
Participation rates are a floor, not a ceiling. A program where everyone attended every session but no one applied anything is not a success. Measurement should track behavior change and business outcomes, not just completion.
Engagement metrics provide the baseline. Track attendance, course completion rates, coaching session usage, mentoring connection rates, and event participation.
Development and readiness metrics reveal whether participants are growing. These include pre- and post-assessment scores, manager feedback ratings, self-reported confidence in specific competencies, and career plan completion rates.
Talent and business metrics connect the program to organizational outcomes. Track ninety-day and one-year retention rates for program participants versus non-participants, internal mobility rates, promotion readiness scores, and for university programs, employer placement rates and alumni engagement levels.
TheDeloitte 2026 Gen Z and Millennial Survey, which surveyed more than 22,500 respondents across 44 countries, found that only 25% of Gen Z workers and 21% of millennials prefer rapid career progression.
Most prefer gradual growth and lateral moves to build skills for long-term success. Programs that measure only promotion rates will miss this reality. A participant who moved laterally into a better-fit role is a program success, not a retention failure.
Common Mistakes to Avoid
Using generic content. Leadership development modules designed for mid-level managers rarely serve a 23-year-old in their first full-time role. Early talent needs content scoped to actual early career challenges: professional identity, workplace norms, feedback literacy, self-advocacy, and early career decision-making.
Treating mentorship as the whole program. Mentorship is valuable. It is not a program by itself. A mentor can offer perspective and connection, but cannot replace curriculum, coaching, or structured feedback. Programs that consist entirely of a mentor matching system underdeliver on development.
Skipping manager and advisor enablement. The people responsible for daily contact with participants need tools, not just intentions. An unsupported manager defaults to existing behaviors. An under-resourced career services advisor defaults to appointment-only support. Both groups need structured guidance to play an active role.
Measuring only attendance. Attendance proves people showed up. Outcomes prove people grew. Build a measurement model before the program launches, not after, so you know what data to collect from day one.
How PathWise Supports Early Career Development
PathWise offers a flexible support layer for both organizations and universities running early career programs. For employers, PathWise provides career resources, online events, short courses, coaching packages, assessments, tools, and templates that extend a program’s depth without requiring everything to be built in-house.
For colleges and universities, PathWise helps career services teams reach more students and alumni with structured, self-guided resources that free advisors to focus on higher-value, personalized engagement.
Books to Improve Communication Skills: The Best Reads to Talk Clearly, Connect Better, & Be Heard
July 19, 2026
Books to improve communication skills work because they slow down a skill most people only practice under pressure. A reader can study how to listen, ask better questions, and handle conflict before trying those moves in a real conversation. That preparation turns vague advice into a specific, repeatable behavior.
The goal is not to memorize a script. The goal is judgment: knowing what to say, when to say it, and how to say it so another person actually understands you.
Why Reading Changes How You Communicate
Communication breaks down for a small number of predictable reasons. People assume instead of asking. They react instead of listening. They reach for vague language when the moment calls for something precise.
Books help because they name these patterns before you meet them in real life. You can read a chapter before a difficult conversation, then try one technique instead of guessing. That repetition, spread out over weeks instead of crammed into a single high-stakes moment, is what makes the change stick.
Aura Intelligence’s year-end analysis of U.S. job postings found that communication accounted for 25.5% of listings in its most recent benchmarking report, ahead of management and customer service (Aura Intelligence). Employers are not asking for charisma. They are asking for a skill that can be studied and practiced like any other, which is exactly what the right books to improve communication skills are built to teach.
What Recent Research Says About Communication Skills At Work
The evidence for treating communication as a trainable skill, not a fixed personality trait, keeps getting stronger.
Even as generative AI reshapes daily work, human communication remains the skill employers say they cannot automate around (Castrillon).
Listening specifically has a measurable effect on trust. Leadership research firm Zenger Folkman found that managers rated as poor listeners ranked in only the 15th percentile for trust among their teams, while managers who listened well reached the 86th percentile (MacArthur).
That gap is not cosmetic. Trust affects whether people tell a manager about a problem before it becomes a crisis. Listening is a large part of what closes that gap, which is why several of the books below spend more time on hearing people out than on speaking well.
Quick Self-Assessment: Name Your Communication Bottleneck
Before picking a book, name your problem as a behavior, not an identity. “I’m introverted” is not a bottleneck. “I avoid speaking up in meetings” is.
Match your pattern to one of these categories:
Clarity issues show up as long explanations, vague requests, or messages that need several follow-up questions to make sense.
Connection issues show up as polite but distant responses, where people answer your questions without ever opening up.
Confidence issues show up as over-preparing for simple conversations or staying silent when you have something useful to add.
Conflict issues show up as escalation, or the opposite: going quiet and withdrawing the moment someone disagrees with you.
Influence issues show up as hearing “no” repeatedly without ever learning what is actually driving the resistance.
Once you know your category, the reading list gets much shorter.
How To Choose The Right Book For Your Specific Goal
The right books to improve communication skills depend on the moment where you struggle most. That keeps you from reading five overlapping books that all say the same thing in different words.
If starting conversations is the hard part, look for books built around openers and social comfort rather than general theory. If disagreement is the hard part, prioritize books built around conflict, not books about charisma. If your goal is workplace impact, look for books that teach clarity, feedback, and influence specifically, since general social skills do not always transfer cleanly to a meeting room.
Best Books For Active Listening And Being Fully Present
Active listening is the skill most communication problems trace back to, and it is also the most trainable.
Just Listen, by psychiatrist Mark Goulston, builds around a simple idea: people resist you less when they feel heard first. The book’s core technique, mirroring back what someone just said before responding, works because it lowers defensiveness before you say a single word of your own.
Crucial Conversations: Tools for Talking When Stakes Are High, by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler, is built around a concept the authors call the “pool of shared meaning,” the idea that a conversation improves as more relevant facts and feelings get safely into the open. The book is built for exactly the moments wherepausing before you react matters most: performance conversations, disagreements with a boss, and conflicts that have been avoided for too long.
Nonviolent Communication: A Language of Life, by Marshall B. Rosenberg, teaches a four-part structure: observation, feeling, need, and request. It is slower than natural speech at first, but it removes blame from requests, which is why it works well forreflecting meaning back to a speaker during tense conversations.
Best Books For Small Talk And Everyday Conversation Comfort
Confidence in casual conversation comes from curiosity, not from memorized lines.
How to Talk to Anyone, by Leil Lowndes, offers a large set of concrete behaviors: how to enter a group conversation, how to exit one gracefully, and how to read a room before you speak. Treat the techniques as prompts to experiment with, not a script, or they will sound rehearsed. PathWise hasseven practical tips for starting any conversation that pair well with the book’s more detailed behavioral breakdowns.
The Fine Art of Small Talk, by Debra Fine, breaks ordinary social moments into steps: starting a conversation, sustaining it, and exiting without awkwardness. Fine’s most useful point is about silence. A pause is often the other person processing, not a sign the conversation has failed.
How to Win Friends and Influence People, by Dale Carnegie, remains one of the best-selling nonfiction books ever published for a simple reason: its core advice, showing sincere interest in other people and avoiding needless friction, still holds up.
Best Books For Deeper Connection And Trust
Depth in conversation depends on safety. People share more when they believe they will not be judged or rushed toward a solution.
Supercommunicators, by Charles Duhigg, argues that every conversation is really one of three types: practical, emotional, or social, and miscommunication often happens when two people are having different types of conversation without realizing it. Naming which type you are in changes what “listening well” even means in that moment.
We Need to Talk, by Celeste Headlee, focuses on habits that build trust over time: staying present, asking clear follow-up questions, and resisting the urge to fix a problem before someone has finished describing it. Depth also needs limits. Empathy without any boundary becomes emotional overload for the listener, and Headlee is direct about that tradeoff.
Best Books For Professional Writing And Workplace Clarity
Workplace communication rewards clarity over eloquence. People need to know what you mean and what you want them to do next.
The Pyramid Principle, by Barbara Minto, teaches a structure used widely in consulting: lead with your main point, then support it with grouped, logical evidence underneath. It is one of the more mechanical books on this list, which is exactly why it works for reports and executive summaries.
Everybody Writes, by Ann Handley, is built for anyone who communicates mostly through email, documents, and messages rather than meetings. It is direct about cutting throat-clearing sentences and getting to the point faster, which is useful for anyone who wants tosharpen unclear writing at work without sounding curt.
Best Books For Leadership, Influence, And Negotiation
Ambiguity from a leader gets expensive fast. When leaders are unclear, teams fill the gap with assumptions, and that slows execution.
Radical Candor, by Kim Scott, argues that feedback should be caring and direct at the same time, not one traded off against the other. Scott’s framework is one of the clearer answers to how togive feedback that is honest without being harsh.
Influence, by Robert B. Cialdini, explains the principles behind why people say yes, including reciprocity, social proof, and scarcity. The book is frequently misread as a manipulation manual. Cialdini’s actual argument is closer to the opposite: influence works best, and lasts longest, when it is used transparently.
Never Split the Difference, by former FBI negotiator Chris Voss, treats negotiation as a form of tactical empathy rather than a contest. Voss’s central technique, naming the other person’s emotion out loud (“It sounds like you’re worried about the timeline”), defuses tension before either side has to make a concession.
Best Books For Public Speaking And Thinking On Your Feet
Public speaking becomes manageable when you lean on structure instead of hoping for inspiration in the moment.
Talk Like TED, by Carmine Gallo, breaks down recurring patterns in memorable talks: a strong opening story, a small number of core ideas, and language built for listening rather than reading. The Quick and Easy Way to Effective Speaking, by Dale Carnegie, is older but still useful for its emphasis on preparation and repetition over raw talent.
Best Books For Emotional Intelligence Under Pressure
Emotional intelligence changes how a charged moment plays out. It is the difference between naming what you feel and simply reacting to it.
Daniel Goleman’s Emotional Intelligence remains a common entry point for understanding how emotion shapes behavior before logic gets a say. Emotional Intelligence 2.0, by Travis Bradberry and Jean Greaves, turns that theory into a daily practice, with specific habits for self-awareness and self-management rather than abstract concepts. A fair test of progress with either book: can you say what you feel without attacking, and ask for what you need without demanding it?
Best Books For Body Language And Reading People Accurately
Nonverbal signals shape trust because people look for consistency between what you say and how you act while saying it.
What Every BODY Is Saying, by former FBI agent Joe Navarro, explains common nonverbal cues while stressing that context matters more than any single gesture. Use it to build awareness of your own signals first, since that is where the highest return is.
Talking to Strangers, by Malcolm Gladwell, comes at this from the opposite direction. It examines why people are so often wrong when they try to read strangers, arguing that most of us default to believing people are telling the truth, a tendency that usually serves us well but occasionally fails badly. It is a useful corrective for anyone who thinks they can accurately read a stranger in a first meeting.
Best Books For Difficult Conversations And Conflict Repair
Most people either escalate a conflict or avoid it entirely. Both responses skip the part where the actual disagreement gets addressed.
Difficult Conversations: How to Discuss What Matters Most, by Douglas Stone, Bruce Patton, and Sheila Heen, separates every hard conversation into three layers happening at once: what happened, the feelings involved, and what it says about each person’s identity.
Naming which layer is actually driving the tension is often the fastest way to de-escalate it. It pairs naturally with Crucial Conversations and Nonviolent Communication, covered above, since all three treat conflict as a skill rather than a personality trait to manage around.
How To Turn These Books Into Real Skill
Reading is step one. Practice is what turns an idea into a skill you actually have.
Pick one technique from a chapter you just read.
Use it in one real conversation that same day, even a low-stakes one.
Write a single sentence afterward about what changed.
Repeat with one new technique per week instead of trying to apply an entire book at once.
This method works well with Crucial Conversations and Nonviolent Communication in particular, since each chapter maps to one specific, rehearsable behavior.
Recommended Reading Paths Based On Your Goal
Pick the path that matches your biggest bottleneck, then commit to practicing it before moving to the next book.
Social confidence:How to Win Friends and Influence People (Carnegie), then The Fine Art of Small Talk (Fine).
Conflict skill:Nonviolent Communication (Rosenberg), then Crucial Conversations (Patterson, Grenny, McMillan, and Switzler).
Workplace clarity:The Pyramid Principle (Minto), then Everybody Writes (Handley).
Leadership:Radical Candor (Scott), then Influence (Cialdini).
Public speaking:Talk Like TED (Gallo), then The Quick and Easy Way to Effective Speaking (Carnegie).
Common Mistakes People Make When Applying Communication Advice
The most common mistake is sounding scripted. A technique should support your own voice, not replace it.
The second is ignoring context. A direct style that works well in a status meeting can fail badly in a personal argument, and a warm style that works with friends can read as vague in a negotiation.
The third, and most common, is treating this as a speaking problem when it is usually a listening problem first. Confident speakers who read Just Listen or Crucial Conversations are often surprised by how much of their communication trouble was actually about attention, not vocabulary.
Turn Better Communication Into Career Momentum
Strong communication only pays off if you can use it under real pressure at work: in a meeting, a written update, or a conversation you have been avoiding.
The books to improve communication skills above build the framework, but practice under real feedback is what makes it stick. Explorecareer services for coaching that turns a chapter into a habit, orreach out to the PathWise team to build a plan around the specific conversations you find hardest.
PathWise offers a growing library of book summaries on careers, professional development, and personal growth. For some books, we've also created short video summaries as well.
Our book summaries are not a substitute for the books themselves. They are merely intended to provide an overview of the books, similar to a review. Please support the authors whose work you find interesting by buying their books.
How To Stay Human In The Age Of AI, With Johan Roos
September 1, 2026
AI can write, analyze, summarize, code, and create—and its capabilities are advancing at a remarkable pace. So as machines become more intelligent, what will keep humans indispensable?
Johan Roos believes the answer lies in what he calls “human magic”: the distinctly human capabilities that technology can support, but never replace. Johan is an internationally recognized strategy scholar, former business school dean, co-creator of LEGO Serious Play, and author of Human Magic.
In this episode of Career Sessions, Johan and J.R. explore why our advantage in an AI-powered world comes not from trying to compete with machines, but from becoming more human as AI gets smarter.
They discuss the five capabilities at the heart of human magic—curiosity, creativity, critical thinking, communication, and collaboration—and why practical wisdom and sound judgment are becoming increasingly valuable. They also examine the danger of “cognitive offloading”: relying so heavily on AI that the very skills that differentiate us begin to atrophy.
Johan shares what leaders should be doing differently in the AI era, including asking better questions, creating the conditions for their teams to think deeply, and focusing the AI conversation on transforming tasks rather than eliminating jobs.
The conversation also revisits the origins of LEGO Serious Play and what Johan learned about creativity, collaboration, and better decision-making by getting people out of conventional meetings and thinking with their hands. Those lessons may be even more relevant as organizations figure out how humans and AI should work together.
The takeaway: use AI intensely to prepare—but when the room is watching, show up as a human.
Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcast/johan-roos/.
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Watch the episode here
Listen to the podcast here
How To Stay Human In The Age Of AI, With Johan Roos
Artificial intelligence is changing the way we work at a remarkable pace. Every day, it seems like there’s a new tool that can write, analyze, summarize, code and even create. It sparked an important conversation about productivity, but perhaps an even more important one about people. As AI becomes more capable, what’s going to keep humans being indispensable? Will it be our knowledge, our experience, or could it be something even deeper like our judgment and creativity? Our ability to navigate ambiguity, or our capacity to lead other people through uncertainty, or something else perhaps.
My guestJohan Roos, has spent decades exploring these questions even before AI became mainstream. Johan is an internationally recognized strategy scholar, former dean of several leading business schools, and one of the pioneers behindLEGO Serious Play, a groundbreaking approach that’s transformed the way that organizations work, think, collaborate, and problem solve. His latest work, a book calledHuman Magic, explores how leaders can preserve the uniquely human qualities that technology can support but never replace.
Defining Human Magic And Core Human Capabilities
In our conversation, we’re going to discuss what wisdom looks like in an age of algorithms, why better leadership starts with better thinking, and how each of us can continue to create value in a world where intelligence is increasingly abundant, but sound judgment still remains remarkably rare. I’m J.R. Lowry, this is Career Sessions. Here’s my conversation with Johan.
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Johan, thanks for joining me today. It’s good to meet you.
Good to meet you, too.
Let’s get going. You have a new book out calledHuman Magic. You’ve spent decades studying strategy and leadership in organizations. Talk about what you mean by human magic and why it matters in particular now.
I define human magic as a set of distinctly human capabilities that machines can support but never replace. In the book, I group this into five, such as curiosity, creativity, critical thinking, communication, and collaboration. The magic is not mystical. It’s what happens when a person, you and I, frame the question that algorithms hadn’t posed or we hold the room with real conviction. That’s what I mean with human magic.
This is particularly important now in an era where AI seems to be able to do more and more things every day. For the average person who’s thinking about how to survive in this world of AI from a professional perspective. What advice would you have for them about how to think about these uniquely human capabilities and to sharpen their thinking and use them to their advantage?
You’re right that the time is now to think about these things. The AI tools are amazing. I’m a user. I’m sure you are too and all our audience. We should do that. I’m a techno-optimist and techno-positive person. There is a certain danger to this as well. There is a seductive danger. Seduction is great. When things are nice and it flows and things are effortless, we are fantastically enchanted by this. There is a risk of a slippery slope that we, in a sense, stop doing certain things and we delegate.
I wouldn’t say our soul, but we delegate some of these capabilities or a part of our human magic to machines. We should be careful about that. Overall, it’s about being careful to think about what you’re doing. There’s lots of research now showing some dangerous patterns. Be careful and don’t get too enchanted so you go down what I call in the book the slippery slope of erosion rather than using these tools to amplify yourself and your human magic, you can say.
I’ve heard the expression cognitive rot to refer to at least one part of what you’re talking about, which is that people become so reliant on these tools that they start to dull the very skills that they need, like critical thinking, as an example. You’ve got the fact that the tools sometimes aren’t as great as we are at doing things. Hence, the idea of work slop and people handing over something that an AI tool has done and saying, “This is finished work,” without trying to add their human intelligence on top of it is another issue. We’re seeing both of those things, at least from my perspective.
You’re absolutely right. There’s plenty of words for this. The lighter touch, which is started with, I believe in ’24 or ’25. People started the word cognitive offloading. That doesn’t sound so dangerous, then there was like a cognitive surrender, cognitive replacement then I’ve heard brain rot. That’s a little bit too much because rot means you can’t go back. There’s something to this. Think of it as a muscle. I often tell people, “If you don’t use your muscles, what happens? They atrophy. If you don’t use your language skills, for instance, they atrophy.”
If you don’t use your jelly bean, it will atrophy. It is what I mean by the danger. These tools are so good now that they become almost effortless, then it’s very easy. None of our audience, neither you and me are lazy, but some people are lazy. It becomes like, “It’s so nice. Why don’t I just let the machine do this?” I start the morning and I immediately get my coffee and the screen up and running. I stayed there all day.
If you deduct AI from what you need to do? What’s left? It’s more just give it a thought. That’s why I have, after each of these chapters, a very friendly, nice little self-assessment. Not judgmental. It’s like, where are you on your creative thinking? Where are you on creativity? Where are your curiosity on communication? I’m not pragmatic. It’s like flagging a little bit of a warning. That’s all I want to do.
Part of the irony is that the people who are likely to pick up your book are a subset of the people who need your book. They’re probably the ones who are most already focused on continuing to keep their critical thinking, communication and collaboration skills sharp. This is something we all need to be working on. You can either let the tool take over for you, or you can figure out a way to harness these AI tools to your advantage. That’s going to be a key determinant as to whose careers are better than others.
Johan Roos: Don’t get too enchanted so you go down the slippery slope of erosion, rather than using these tools to amplify yourself and your human magic.
First of all, a lot of people will pick up the book. I’m super delighted that it came up on McKinsey’s list of AI books. I trust that they have some good judgment but I also trust that people then say, “This is an interesting book. Why don’t you pick it up?” It’s for everybody. I addressed the book to all AI-anxious and AI-excited professionals of the world, of which there’s many on various levels. For most things, there’s a short-term thing and there’s a longer-term thing.
Focusing On What AI Tools Cannot Replace
We tend to exaggerate all kinds of short-term impact of new technologies, and then we forget about the potential long-term radical consequences that we may not be seeing. You can say there’s going to be the have and the have-nots, the do and the do-nots, and the can and the cannots. Now, a lot of the tech brokers people respond to the question, what should young people do now? They say, “You should learn all of these amazing tools and you should be capable.” They’re right but it’s half true.
If you only try to run after what the tools can do, you will always be a little bit behind. I always tell people maybe you should focus more on what the tools cannot do. That is, they cannot be you. This is the grand message or almost the irony of the time. That the more capable the algorithms become, the more value humanism becomes. You cannot be replaced. Part of you can be replaced but your experience, your curiosity, creativity, and way to communicate cannot be replaced. It can be mimicked but your living experience cannot be replicated. Ensure that you continue to gain this living experience that is you.
That is an important point because as the tools are able to create a higher baseline answer for about anything, then what you add on top of it is the stories and the experience that you’ve got. Which the tools by definition aren’t going to know. For a lot of people, this is going to require becoming better storytellers and thinking more about what they can add on top of the tools. That’s going to be a challenge for some people that some will grab onto. It’s a challenge that others will probably feel intimidated by.
You could say storytellers, but also story creators and all of these fundamental things. Again, I have a whole chapter on communication. I start that chapter and each of the chapters you’ve seen with an anecdote about ancient times. We met some famous historical people. In communication, we meet Cicero, the famous consul in ancient Rome who was known because his slave Tiro took notes, stenography from what he did. We know that he could sway an audience in an amazing way.
He’s one of the first that has been documented on how you sway the audience. He didn’t do it by standing, holding his hand and talking, or telling people to sit down, shut up and listen to him. Rather he used what the Romans called the eloquence of the body. What we would refer to as body language and almost theatrical skills. I use some theatrics in this.
I urge people to say, “No machine can hold the room. You can hold the room.” That’s an extraordinarily important capability as a human being. We are social and we work. We work with other people, so we have to communicate. We have to explain. We have to describe. We also have to persuade. In doing that, we should learn even more how to use the eloquence of the body. Those are incredibly important skills to not forget.
Johan Roos: Shift the whole idea that you should know everything. Instead, focus on being able to ask really good, penetrating questions.
I would agree with you. At the leadership level, organizational level, what advice would you have for companies and other organizations about how to lead in this era of AI in the right way or how they are using AI in the right way?
I’ll speak as a scholar of strategy and leadership, but also as a leader because I’ve led several organizations. I’ve been part of the leadership team of several organizations. As a leader, often you think you should have the answer to all kinds of questions, and pretty quick because then you’re smart. You have a quick answer to things. These days, you can say that data is almost free. You can have anything around you all the time.
It shifts the whole idea that you should know everything. Instead, I often tell people, and I’m not the only one, a lot of people have been saying this. That you should be able to have some good questions. I’ve been reporting to five board of directors in my career. The best board members are the one that pesters you with good penetrating questions. Not to embarrass you or anything. It’s like a good academic reviewer. Not the one with a bad attitude.
It’s like somebody who’s asking these questions to help you. Now, that is a tremendously important leadership skill. Number two is creating the context in which your people, your team, your amazing teams can try to answer this. They’re probably closer to the action. Closer to the front line where things are happening. They probably know the best. They know the answers. If you can work on those two things, asking good, smart questions and creating the context of it then the algorithm will help to find the answers, challenge some of these questions, come with suggestions, and simulate whatever.
Leading With Judgment And Asking Penetrating Questions
The tools are amazing, but you should hold on to some of these things because no machine will have the lived experience you would have. With all the scars that we have, being through all of this, and anyone who’s done change processes and all that. All of the scars we have is your experience from which you draw, you intuit, and you bring things out. Invaluable. That is how you climb the value creation ladder in this world.
As a leader, you should be extraordinarily careful to delegate some of your judgment. Judgment for me is the behavioral output of wisdom, and nota bene. In 2024 and 2025, I was chairing a global group of very senior people in the context of another global organization. These were very big names and they were all CEOs or board members.
The only thing they talked about was efficiency. How many people can we get rid of because of the ChatGPT at that time? The conversation has shifted now because they start to see efficiency isn’t everything. Effectiveness could be a good thing. Peter drops his stuff, doing the right thing or doing things right. That’s very important.
I wonder how much of that is because of some of the backlash that they’ve been getting from employee populations. They want them to use these tools and the employees are like, “All you’re telling me is you’re going to use these tools to get rid of me. Why should I use these tools?” There’s been a bit of that tug of war that’s been going on between leaders and employees.I wonder how much of the shift that’s happening at the executive level is because of that. I wonder how much of it is more just they’ve had their own rethinking of this.
It feels to me like the conversation around AI has been very fluid over the months. We’ve gone from it’s something that people aren’t familiar with to, “It’s going to eat all of our jobs,” to, “I hate it and I don’t want to see it.” There’s this Gen Z rebellion against it. Now, there’s a bit of defensiveness going on among the big AI players and companies about trying to reposition it. It’s been fascinating to watch that play out. I’d love to get your views on that.
It’s equally fascinating because, as I said, you’ve spent the last couple of months meeting God knows how many CEOs, board members, CPOs, learning and development managers in 7 or 8 cities in different countries. The conversation is shifting but it should be shifting. The backlash is because of bad leadership. I say that generally, because how do you expect people to use some new technology if you scare the heck out of them?
If you start to look at the data now, there was a Microsoft report out in May about how co-work is used in the office suite. You can see almost more than half of it are like thinking tools, persuasion tools. It’s about decision and thinking. People are using this as well. The problem is when you start to talk about jobs, I keep telling people, “Don’t do that. Talk about tasks instead. Shift the unit of analysis from jobs to tasks.”
Here’s an anecdote. I met an interesting person whose CEO months ago said, “We’re going to be an AI agentic workforce.” With 25,000 employees, a big global company, and B2B, everybody said, “What does that mean?” He said, “I don’t know. What we should do is that we should develop more than 50,000 AI agents in six months.” Everybody goes, “Wow.” He said, “Nobody will be fired because of this. You’ll get fired because of something else but we will do this together.”
Everybody, the receptionist to the CEO should develop agents of various levels and stuff. Internship and interns and everything. Lo and behold, six months later, they had developed 54,000 AI agents with awards and ceremonies and all cool stuff across all functional areas of all levels. It’s super interesting. I said, “How many are useful?” They said, “A couple of hundred are useful and can help efficiency and effectiveness.” People were very happy and people were positive towards this. This was good leadership. You can say we get what we ask for if you scare people. That’s how it is.
Johan Roos: Don’t talk about jobs; talk about tasks instead. Shift the unit of analysis from jobs to tasks.
It’s a great example of how you turn it around and say, “We’re going to do it together. Not to you.” It completely changes employees’ mindsets about this. I see that happening in my own travels. I see that happening more lately where companies are encouraging people to use this and trying to demonstrate from the top down that it is about how to do tasks differently. Not necessarily how to replace people.
The Origins And Strategy Behind Lego Serious Play
I want to shift gears a little bit because before you wrote this book, you were one of the co-founders of LEGO Serious Play, which has had a massive impact on the business world. The idea of LEGO® and SERIOUS PLAY® is unconventional at first glance. Talk about the origins of it and the problem that you were trying to solve when it was first created.
It’s a bit of a baby for me. My colleague Bart Victor and I were professors at the IMD in Switzerland, a top renowned executive education place. For various reasons, we ended up doing experiments and stuff. People particularly thought I was a bit crazy because I pushed pretty hard. The real problem was this, and it’s very similar. The real problem was lack of depth in strategy conversations. I was a strategy professor and strategy consultant. I was teaching and doing a lot of stuff, working with companies. I found that I used the same tools, the same language, the same models and the same consultants and expected a different outcome. Which we know what that is. I thought that in these strategy conversations, it was pretty superficial.
The obvious people talked. The more introverted people were silent and so forth, so we changed the playing field. We changed the mode of what we call intentionality from, “Let’s not just have serious work. We could be a little bit playful,” then we changed the medium of communication from 2D flatland, Post-It note, flip charge or whatever, to physical stuff and it happened to be that LEGO® bricks are pretty useful but it’s not about the LEGO®. It’s the physicality of the stuff. What happened was, when people started to build their strategy or build their environment, their competition, their customer relationship, first of all, using their hands, they started to see different things.
Johan Roos: When people started to build their strategy using their hands, they started to see different things. Neurologically and sociologically, they started to talk to each other in a different way.
This is neurologically very interesting. Sociologically, they started to talk to each other in a different way. Almost anthropologically or psychologically, the introverts started to talk. The silent people got a voice. Suddenly, you got more out of the group than before. You had people say, “I didn’t know you thought that. Why haven’t you told me? We’ve been working together for five years.” Somebody leaned back and said, “I haven’t seen it this way before because they could look at it in 3D and they can change their perspective.” That was extraordinarily gratifying.
Out of that came a developmental process, and I’ve written about that. It is extraordinary what can happen. This is now, as you say, is used from NASA to small companies, universities, all over the world. Tens of thousands of people are using it. I’m super proud of it. It was a depth problem. My buddy Barton and I published a paper on what this method can be used for in the future, namely to get the same depth in specifying and designing the work that AI agents should do.
Now, you sit and do this. All the agents should do this and give me a prompt. We should have sub-agents or eight sub-agents doing this but that’s very superficial. Most of this research shows it already. Most of these are not super good. You can do much more. We’re proposing in a sense that if you use these kinds of more experiential, more almost creative arts therapy type of approaches, you can very quickly get to a better design, better specification of what AI agents should do. The same method, different problem, but same principles.
Clearly, creativity, collaboration and communication, the three of the five C’s that you talk about in Human Magic are also deeply enmeshed in LEGO Serious Play. I’m curious to get your perspective about how those three things and others, if relevant, evolved in the way that you think about them, creativity, collaboration, and communication and that LEGO Serious Play constructs how we interact with AI tools.
It is interesting. I’ve drawn on data from different sources, three sources. First is my own experience as a scholar, but also as a leader. Also, having implemented one of the first AI implementation projects globally in higher education two months after ChatGPT. The other source is talking to a lot of leaders about what do you think is going to be the impact of AI on leadership throughout 2025. I even designed an AI voice assistant to interview people to do this. It’s super interesting.
The third one is a 2024-2025 research project on LEGO Serious Play facilitators. I did study how they used AI tools in their facilitation. That’s where I got the inspiration for this. You can say that the five C’s, and which we haven’t talked about, practical wisdom, the overarching capability, is all through LEGO Serious Play.
Practical wisdom has a manifestation in a behavioral manifestation in judgment. When we make a judgment call, we say, this is good versus bad. This is the right thing versus the wrong thing. In fact, also this is beautiful versus not. It is also about, what in LEGO Serious Play, we call the simple guiding principles. That typically comes out of things. It’s your guidelines. Your gut feels articulated, which is an integral part of an LSP process.
In a sense, these are intertwined. LSP is in this and this is in LSP. All of it, all of the five Cs and practical wisdom. I’ll make that very clear in the next book, which we call Mastering LEGO Serious Play. I’m super delighted because in this world of AI and algorithms we can go back to hands-on, minds-on physical stuff and see how powerful that remains in order for us to remain and develop us as humans.
As you said earlier, just the very nature of working with your hands has a neurological impact that sparks different brain patterns than would happen if you were just staring at a whiteboard and trying to have the same conversation or sitting around a conference table. That’s the piece, coming back to the idea of human magic, that people need to grab onto. That’s the idea of how you are tapping into your human uniqueness as opposed to replicating things that increasingly a machine could do for you.
You’re right. My good professional friend, Mitch Resnick, who is the director of MIT Media Lab and who’s kindly endorsed the book as well. He’s written about this for a long time. They’ve done wonderful stuff. He’s written about kindergarten throughout life. Think about that. When we put our children or grandchildren in kindergarten, what do we tell them to do? What do we encourage them to do? Play with their hands. Eat some dirt, maybe. Use some bricks or some clay or Play-Doh or paper drawing.
All of that stuff is wonderful because why? We know it’s experimenting. There’s old theories about how we experience the world or we discover the world through our hands. What happens when we put them in school? Sit down, be silent, and listen. His idea is we should have this kindergarten feeling throughout life and I am so with him. LEGO Serious Play is an attempt in all modesty to encourage that feeling in the spirit of human magic.
Practical Wisdom, Ethics, And The Limits Of AI Thinking
Many people lose that childish nature. Almost everybody does by the time they become adults, certainly. You’re essentially trying to tap back into that to get them to step back from a problem. See it in a different light and have fun with their colleagues. Those things don’t happen very often in workplaces anymore. Yet they can unleash great, collective, and creative ideas. That’s the power of the whole thing.
It won’t happen if you scare the heck out of people by saying, “Use these tools and we can make you redundant.” That’s not the way to go. Hopefully, collectively, leadership has learned and approached this as a smart way. We cannot be naive. There are fields where we have to push hard and do hard stuff. I do talk a little bit about defense and the military in one of the final chapters. What happens in a world where we delegate these decision calls, the ultimate one as well, to a machine?
I do refer to some of these amazing science fiction authors at the end. You have Philip K. Dick and Arthur C. Clarke. They are not just movies, but good quality literature on imagining a world where the machines decide what happens when humans are either drugged or through pleasure, as it is in A Brave New World, or through fear, as it is in 1984.
We do Robert’s dream of electric sheep. It’s a very good question asked by Philip K. Dick many years ago. I often urge people at the end, I’ll say, “Read more stuff. Expose yourself to what’s happening out there and broaden your mind and show that you as a human are broad enough,” and move ahead so that you’re not bitten in the rear end by the machine.
This comes back to your idea of wisdom relative to intelligence. There’s a difference between the two. We’re realizing now, to your point from earlier, practical wisdom is much more important and much more human than mere intelligence. You can find the answers to almost anything online now. It’s amazing. At the snap of a finger and written in a paragraph form for you or whatever form you want for that matter. The interpretation of that, the judgment of that is a very key human skill that we need to hang on to and get better at.
Isn’t it interesting that when we talk about wisdom in a sense, we visualize wisdom typically by somebody looking like Dumbledore? You’re wondering what is wise about this person? It’s almost like a life experience. You think of it as somebody who’s experienced a lot in life and that’s what it is. This is nothing new in it. Throughout different cultures, there are words for wisdom. It’s the habit of making a decision and taking actions that are good, not just for me, myself and I, but for the community I’m part of. This was the idea that leaders should have more than intelligence, know what, or technical skills like know how, and being a little bit street smart.
They should also have this above idea of looking after the community. It’s so true today. I define it in the book as the almost emergent property of these five Cs, or even the orchestrator, you can say also. These are things we should pay extraordinary heed to and be careful about cultivating. When people say to me, “What is it?” I said, “You can think of it as the ability to answer in the way I just said. That’s good not just for you, but also for others. The question, what matters? What is right? What resonates where you are in your context? What will work in your situation?”
It’s very context-specific stuff. If you start to delegate these questions to the algorithm, you are moving from green to amber towards the red light in your warning signal system. You should be extraordinarily careful so that the last question will not be or should I think, what is right? What works? When you do that, you are almost like abusing a large language model assuming it’s a large thinking model with ethical standards and living experience. Sorry, folks, it’s not.
The tools are so good. We’ve talked about that at several points in the conversation they will give you an eloquent answer to just about any question that you ask. They do a pretty good job of imitating thinking. Not just a probabilistic collection of words strung together that turns out to be pretty gosh darn good. Most people don’t understand the technical underpinnings of a large language model. They take it more at face value because they see the outputs of it. That’s where you start to get into the slippery slope that you talked about earlier.
The producers of this, as smart and brilliant as they are, also read psychology. They know what happens if you add to an output or you start an output and answer with. This is brilliant. What a great question you’re posing. You get sucked into it. This is like a smart move. I’m just awaiting an advertising model for this and then it will be dangerous for us but this is very important. It’s very important for young people to be aware of this and be made aware of this. I met parents in different countries who are very worried about their 8 to 12-year-olds, for example, who challenge them and say, “No, mom. ChatGPT says, or perplexity says this. You’re wrong.”
Also, I’ve had parents who are senior professionals, and they bring up these issues such as, “How will our children be able to communicate and collaborate? There’s evidence that people are using this. This is when people withdraw.” You almost like to reduce your emotional intelligence. You reduce your critical thinking. You reduce your sense of engaging with others except online. There’s some real warning signals out there about young people’s first best friend or boyfriend or girlfriend is now an AI tool.
Critical Thinking And Optimism For The Future Of Work
I’ve heard some of those same stories, too. People are using it as a replacement for therapy because therapy is hard to get, especially here in the United States. We have a shortage of therapists available, so people are turning to these tools for that. We have to keep reminding people, and we saw this with social media. There is a dark underbelly to this whole thing that you need to be aware of. If you’re not aware of that or you’re ignoring the perils of it, you’re going to be slipping down that slope.
You’re so right. I was at the Luxembourg School of Business and met Joel Mokyr, the Nobel Prize winner in Economics in 2025. When asked, he said very clearly, “AI will answer your questions. It will not tell you which questions matter,” which of course is a statement anyone can say but said from such a strong person and super charming man. It’s a good reminder. You can get answers to anything but who’s in charge here? You or the machine? Who should ask the question? You can bounce things. There’s a wonderful way of using the tools as a critical thinking of yourself for a reviewer.
You have to work hard on that. If we don’t work hard on this, we will go down the slippery slope. If you work hard and I work hard with these tools, I work 25 versions of this and I challenge myself. I go back and forth. I’m a professor, so I’m used to tough reviews, but go for it. If you don’t do that, it’s so easy to take this first thing and say, “This is my output.” It’s potentially devastating. Three of the big four consulting firms in the last nine months have had to retract and pay for things that were wrong in their major report.
Which is always embarrassing when you’re a big consulting firm.
Potentially devastating.
With all of this in mind, what gives you optimism about the future of leadership and work?
I am an optimist in myself. I’ve always been an optimist and I’m a techno-optimist, but to quote Mokyr, “What could possibly be wrong? Political stupidity.” It is in a sense. I think it’s fantastic. New tools have always come to us and we’ve used them in the same way. First, there’s a hype and then we know the curve and then go down. It’s always changing. This one is just bigger and faster than anything else we’ve seen.
We’re humans. We survive. It’s a species we survive. One or two of us may fall around, fall outside but as humans, we will survive. We are super agile. It’s going to be a rough ride here, but it’s going to be a heck of a ride. I’m very positive in a sense that this will be a better world. It’s very easy to be a doomsayer. A lot of people make a lot of money, selling books and saying the world will go under or technology will kill us and all that. We love to go and see all of these movies about Terminator and all that but we will prevail.
We will come up with new stuff. There will be technologies throughout history. We’ve seen these technologies that change things dramatically. It will destroy and will pollute. There will be new technology that will take care of the pollution and it will reduce things. There will be like two steps forward, one back. Three steps forward, one back all the time. We have a bright future ahead of us.
Last question. If there’s one idea that you would want our audience to take away from human magic in particular about the way they lead or the way they make decisions or the way they approach their careers, what would it be?
I can do an overall and a little bit more practical one. Overall, in a sense, our advantage is to become more human as AI gets smarter. Not less human. Our advantage becomes more human as AI becomes smarter. Not less. For anyone who’s working as a professional, we like to do things. We read stuff. We prepare, and then we present them. We do all of this stuff. I will say use AI at full intensity to prepare but then show up as a human when the room is watching.
Johan Roos: Our advantage is to become more human as AI gets smarter, not less. Use AI at full intensity to prepare, but show up as a human when the room is watching.
It’s been a fascinating conversation. It’s certainly a very thought-provoking one and a very timely one, given that AI is upon us in full force. I thank you for being with me. It was great also to hear your perspectives as one of the co-founders of LEGO Serious Play, which as I said earlier, it’s a huge impact on the business world and beyond. Thank you for your contributions. Thank you for your thoughts and your time.
Thank you. If anyone is interested, it’s very simple, I’m at HumanMagic.one. If you do dot-com or org, you’ll get into the magician’s society.
Good enough. Thank you again.
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Key Takeaways: Cultivating Your Human Advantage
Lots to think about from the conversation that I had with Johan. First, as AI becomes more intelligent, it becomes even more important for us to tap into our unique human capabilities. Things like curiosity, creation and collaboration. That’s because it’s becoming less important to be the person who knows the most. It’s about becoming the person who has sound judgment, who can navigate ambiguity, who can ask better questions, who can build trust with others, who can help others make sense of complexity. These are the capabilities, as Johan said, that become more, not less valuable as technology advances.
Second is that leadership is increasingly about the idea of creating conditions for better thinking. Johan started down this path when he first conceived the idea of LEGO Serious Play. In fairness, he probably was thinking about it before then. He changed the world in the way that people started to look at how you can take something like playing with a bunch of Lego bricks and use it to foster better judgment, decision making, collaboration and creativity in an amazing way.
In our era of AI, this becomes even more important. The way that you can tap into our human uniqueness and help people harness it in a way that will help make them better as individuals, as teams and as organizations. The third thing that I would highlight is the fact that how you use these tools is important. If you are using them to do your work for you, you are just hurting yourself in the long term because you are going to erode your strengths. The things that make you human, the creativity and the curiosity and all of those things.
If you use AI to make you better, then you are tapping into its strengths without giving up the things that make you strong. That, to me, is a huge difference that will determine whether you thrive in our era of AI or potentially struggle in our era of AI. I would encourage all of you to think about how do I make these tools work for me as opposed to being imposed upon me?
All of that will come together in the way that we go through our careers, the way that we progress through organizations, the way that we lead others, and ultimately the way that we coexist with AI and aren’t undone by it. It’s an important moment. I hope you took a lot away from this conversation. As always, I invite you to subscribe to the show onApple Podcasts,YouTube andSpotify. If you found the discussion enlightening, sign up for my membership community, which is called PathWise or our newsletterPathWisdom. Thanks.
Johan Roos serves as Senior Advisor to the Global Peter Drucker Forum, where he helped initiate the Next Management initiative on leadership, and he is Professor in Strategy and Executive Advisor at Hult International Business School (Boston, San Francisco, Dubai, London). Throughout his career, Johan has been driven by curiosity about how people and institutions learn, adapt, and rediscover their imagination when technology changes the rules. This interest led him to co-invent the globally adopted LEGO® Serious Play® methodology, enabling thousands of organizations to tackle complex challenges through imaginative, hands-on exploration.
His latest book, Human Magic: Leading with Wisdom in an Age of Algorithms (Routledge, 2026), distills multi-year research with executives and organizations into a practical framework for preserving curiosity, practical wisdom, and human agency when intelligent machines can provide instant answers. Across his roles as educator, advisor, investor, and speaker, Johan’s work is animated by a simple conviction: management, at its best, is humanity at work.
Why Great Teams Work Differently, With Ron Friedman
August 24, 2026
Why do some teams consistently outperform while others—with equally talented people—struggle with endless meetings, constant interruptions, and burnout?
In this episode of Career Sessions, JR Lowry sits down with organizational psychologist and bestselling author Ron Friedman to explore what separates exceptional teams from average ones. Drawing on research involving more than 6,000 workers for his new book, Super Teams, Ron reveals that only about 8% of teams qualified as “super teams”—and that what distinguishes them often runs counter to conventional wisdom about productivity, collaboration, and where work should happen.
Their conversation covers:
Why how a team works matters more than where it works—and what that means for the ongoing debate over remote, hybrid, and in-office work
How excessive meetings and always-on communication undermine productivity—and why great teams establish clear meeting guidelines
Why individual productivity hacks can actually create bottlenecks for the rest of the team
The importance of protecting focused work and why “brainwriting” can produce better ideas than traditional brainstorming
How active recovery outside of work can improve performance—and why leaders’ recovery habits can affect their teams
The three ingredients of workplace trust: competence, caring, and consistency
Why shared goals, role clarity, and interdependence are essential for creating a true team mentality
Practical ways to take control of your workday by looking forward, looking backward, and staying present
Why working longer hours eventually produces diminishing—and even negative—returns
How high-performing teams are approaching AI differently, including openly sharing prompts and learning from one another rather than hiding their AI use
The central message is simple: great teams aren’t built by assembling the smartest people or forcing more collaboration. They’re built intentionally, by creating the conditions that allow talented people to do their best work—both individually and together.
Whether you lead a team or work as part of one, this conversation offers practical, research-backed ideas for reducing friction, building trust, protecting people’s time, and creating a team that performs at a higher level.
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Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcast/ron-friedman/.
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Why Great Teams Work Differently, With Ron Friedman
Think about the best team that you have ever been part of. Odds are you didn’t just accomplish more. You looked forward to going to work. You trusted the people around you. Meetings felt productive instead of draining. You challenge one another and you learn from one another. The whole truly became greater than the sum of the parts. Now, think about the worst team you’ve ever worked on. Probably the same level of talent, if we’re honest. The same good intentions. Yet, somehow, everything felt harder.
Communication was difficult. Meetings multiplied. Progress slowed. Often, by the end of the day, you and probably everyone else went home exhausted. What separates great teams from the average ones? Is it the leader? Is it the culture? Is it the talent? Are we asking the wrong questions altogether? Our guestRon Friedman, believes we have misunderstood teamwork for years. He is an organizational Psychologist, Bestselling Author, and one of the leading experts on human performance at work. His new book,Superteams draws on years of research into what the highest performing teams do differently.
Many of the findings are surprisingly counterintuitive. In our conversation, we’re going to explore why most teams never reach their potential, the hidden habits that separate exceptional teams from everyone else, why so many modern workplaces make collaboration harder rather than the easier and how AI is posed to reshape teamwork in the years ahead. Whether you lead a team or work on one, this episode will change the way you think about what it means to perform at your best. I’m J.R. Lowry. This is Career Sessions.
Let’s dive right in. You have spent years studying high-performance teams across a broad range of industries. Before we talk about what the best teams do. What strikes you most about what the average or less than average teams do?
Eliminating The Time Drain Of Meetings And Messages
The tragic thing when you study average teams is how much of their time is wasted. According to our data, the average worker spends eighteen hours a week in meetings. They then lose another eleven hours a week digging themselves out of messages. The question is, what does that leave for actual real work? It’s about a day.
What happens when you have to do a week’s worth of work in a single day? You find ways of creating more time. You come in early. You stay late. You work weekends. That approach is what is contributing to burnout. We spend so much time wringing our hands saying, “Why are people getting burnt out?” A better question is, how do they manage to get any work done in the first place?
I know you talked about a lot of things that go on, not just meetings but other things that we do at work. They’re well-intended, but they end up working against our individual and collective productivity. Talk about some of those.
Why Individual Productivity Hacks Fail Teams
When you look online, you see a lot of productivity hacks. You see things like, “If you want to get work done, put your phone in the other room, or turn off your notifications, or only check your email a few times a day.” That approach might work for the individual. When you’re working on a team, one person’s deep work becomes another person’s bottleneck. When we studied what high-performing teams do differently, we discovered that the productivity tips that you would assume would lead to individual productivity. Therefore, team productivity ends up not working that way.
They end up having no effect on a team’s productivity. Again, it’s because it slows down the team as a whole. The better solution and this is what we find on high performing teams. They coordinate together to say, “We’re going to take 90 minutes on a Tuesday. Nobody has to check their email. Instead, everybody can get their deep work done.” Once that’s over, we’re all going to check our email together. That enables teams to get more done by coordinating their efforts. Instead of relying on people just coming up with their own rules for themselves.
This is one of the interesting things that you bring to bear. There’s this assumption, as you said a minute ago, that individual productivity translates into team productivity. I was in a meeting where we were incredibly still talking about returning to office and how many days people need to be in the office. We’re having this debate about individual productivity versus what an end up meaning for the team. This is a counterintuitive thing that comes out of your research that individual productivity does not necessarily translate into team productivity. It certainly ought to be driving people to rethink some of the things that hacks or not, they’ve been told.
To your point about a team’s location. That’s another counterintuitive finding that we uncovered in the research. This might be a good opportunity to take a step back and just explain how this research works. My team and I interviewed over 6,000 workers in a wide variety of industries and we asked them two simple questions about their teams. 1) How effective is your team at achieving its goals? 2) Compared to other teams in your industry, how would you rate your team’s performance?
We took the teams with a perfect score. It was a very small group. About 8% of teams qualify. We call them superteams. We look to see what the super teams do differently. We looked at everything from how they structured their day to how they run their meetings. To even how they recover during their off hours. What we discovered is that superteams share three key strengths. The first is they get more done by better managing their time, energy, and attention.
They don’t get stuck losing half their week to meetings. They are much more deliberate with their time, and we can talk more about how they go about doing that. The second strength is, they don’t just collaborate well. They actively make one another better. The third is, even when things are going well, they’re not satisfied. They’re constantly looking to build their skills and improve over time. The encouraging piece. Is every one of those strengths learnable? Which means by building the right habits, any team can dramatically improve its performance.
Now, within that research, we looked at what locations are high-performing teams, most likely to form it. Are they most likely to form in remote teams? Are they most likely to form in office teams? You might assume, because they’re more collaborative. When you’re in person, maybe that’s the key or maybe it’s the best of both worlds. You want hybrid teams to improve the chance of having a high performing team. What we discovered is that location doesn’t matter. The reason it doesn’t matter is because how a team works is vastly more important than where a team works.
You can have everyone at the office but if all they’re doing is getting on a Zoom, which they could have attended two hours ago. That’s not bringing out the best in people. The same issue arises and slightly different flavor in remote teams. What happens with remote teams? They over compensate for not being in the same room. They’re sending more emails and spending more time in meetings. The bottom line is, taking advantage of how a team works is critical and you have to plan around what the team is trying to achieve. Not simply bringing it down to where we are going to work because that oversimplifies the problem.
That short statement that you made in the book, how a team works is more important than where a team works. It has been in my head since I heard it as I was listening to the audiobook. It’s something that probably flies in the face of what a lot of people think, and certainly forms the basis of all of these debates that are happening about how many days people should be in the office.The other thing that you’re bringing up that’s important, and I don’t want to go buy it. It’s this idea that these teams talked about how they want to work together and how they want to use their time. I can’t think of any team that I’ve been on in recent memory that has gone through that stuff.
That’s unfortunate. What it comes down to is being aware of some of this research. Once you have that awareness, that how a team works is more important than where a team works. You can start asking some important questions like, what constitutes a good meeting? The easiest way of eliminating these unnecessary meetings is getting clear with your team on what deserves a meeting and what does. I call these meeting guidelines.
Implementing Decision-Driven Meeting Guidelines
One of the most interesting things I covered while doing the research on high-performing teams. When you look at superteams, they’re much more deliberate with their hours in meetings. Within my team, we have a very simple meeting guideline. No decision, no meeting. If you have a question, pick up the phone or send an email. If you have an update, send a video capture or share a spreadsheet. Unless there’s a decision to be made, we’re not going to pull people away from doing their jobs.
Another example of a meeting guideline that I came across while doing the research for Superteams is no spectators. This is a meeting guideline by the company called Percolate in New York City. They have a meeting guide line. No specters. If you’re not contributing, you don’t need to be in the meeting. What all of these meeting guidelines do is ensure that people’s time in the office is well spent instead of having it just completely monopolized by things that feel like they’re setting people back. Which then forces them to make up for lost hours by multitasking or coming in after hours.
The meeting point certainly was a big focus in the first few chapters of your book and the amount of time people spend in meetings, that surrounds the time that they spend in meetings, and that negative effect that has. It leads people to multitask, which as you point out in the book and we know, doesn’t work because of your task switching. It’s got a cognitive drain that comes with it. You get into some of the things that people are doing like trying to get rid of all the recurring meetings. There’s another example you have in the book that talks about that. Maybe you can share that. I thought that was all a good way of very good practical tips for how to think about the scourge of recurring meetings.
Again, when we talk about the strengths of Superteams. What separates them from average teams? The first one is they get more done by better managing their time, energy and attention. That, for better or for worse, starts with getting rid of unnecessary meetings. We talked about meeting guidelines. That’s one pathway. When we look at the data, superteams are 50% better at avoiding unnecessary meetings. Their 54% out of voiding recurring meetings. Recurring meetings are particularly problematic because they’re so difficult to get off your calendar once they’re on.
High Performing Teams: Individual productivity hacks don’t equal team success. When one person goes dark without coordination, it creates a bottleneck for everyone else. Learn how super teams align their deep work.
In order to get rid of a recurring meeting, you have to have a very uncomfortable conversation with a colleague and say, “I don’t feel like our time together is as well spent anymore.” It’s almost like breaking up with someone. People refer to a voice in that conversation and so they put it off and they keep going to the same useless meeting week after week. There are a number of ways of limiting those. I also think that a big part of this is having some better hygiene around who needs to be in the room. No spectators. There’s one guideline.
More importantly than that, it’s raising awareness of the fact that the more people you have in the room, the longer the meeting becomes and the worse the decision-making becomes. What happens is, more people in the room mean everyone feels like they need to contribute. The meeting is more likely to go off the rails. We have research showing that in the past seven people, the decision-making quality plummets by 10% and it gets worse the more people you add.
In Superteams I give an example of a sample email that you can send the next time you want to diplomatically uninvite someone from a meeting. What it basically comes down to is saying to them, “I’m having this meeting. I would love to share your point of view. What do you think is important for me to point out? I’m happy to circle back with you and let what was determined and what the next steps are.” A lot of times, people think they want to be in the room. What they want is they want a disability and be able to contribute. When you allow them those two things they no longer feel compelled to be in the meeting.
There’s a lot of great tips in the book about how to deal with meetings. Meetings probably along with managers would be in most people’s top three things and annoy them about work. It’s probably policies, managers, and meetings. Not necessarily in that order. You also talked about the fact that I don’t want to gloss over it that focus work is one of the defining characteristics in terms of the more productive teams.
A lot of times, organizations say they want collaboration but what they get is constant togetherness. I use that term because when we are working with our email on, with our slack on, with our text messaging right next to us, it becomes difficult to get actual work done. When you look at what differentiates superteams, it’s the ability to do real work during regular work hours. This is the big challenge that most people have with work and this is why so many people prefer to work from home. It’s because of the constant disruption.
One of the interesting findings in our research is that we asked people. We gave them a very long list of amenities and we said, “Which of these do you have in your office?” Included things like ping pong table, the office dog, collaborative spaces and then private offices. As it turns out, there’s only one amenity that predicts having a superteam. That amenity is a quiet space to do focused work. Again, it speaks to what matters when it comes to having a high performing team. It’s allowing people to do real work during regular work hours.
You look at a variety of highly creative teams. In the book I talk about the examples of Fleetwood Mac and Abba and a variety of other creative acts. The key to their success often comes down to is the ability to toggle between individual focused work and then coming together as a group to refine those ideas. A great example in the research that is worth considering is, a lot of times in offices, we say, “We’re all going to go into the conference room and we’re going to brainstorm because we want to be creative. We want to pull everyone in and get everyone’s ideas.”
When you look at the research, what you find is, if you want more ideas and higher quality ideas, the solution isn’t to brainstorm. It’s to do something called brain writing. What brain writing involves is having everyone as individuals come up with their own ideas and then take those into the conference room and exchange them with one another so that we can build on people’s individual ideas.
What happens when you brainstorm is, the first person who speaks ends up anchoring everyone around the same idea. Now, we’re evaluating whether that idea has merit, instead of coming up with our own ideas. It’s a great example of, if you want people to do their best work. You need to allow them the opportunity to get real focused work during work hours. Otherwise, it’s never going to happen.
That leads naturally into linkage between being on one of these superteams and health and enjoyment as well.
It’s remarkable. Being on a high-performing team isn’t just about being more productive. It’s about being healthier. A big part of it has to do with the fact that the superteams are using their off-hours differently. They’re recovering much more effectively, and part of it is the understanding that when it comes to recovery, simply not working is not enough. A lot of people assume that when they’re not working, they’re automatically recovering.
What the research shows is passive activities. Things like scrolling Instagram or binging Netflix. That can help you unwind, but it doesn’t help you recover your energy quite as effectively as active recovery. Active recovery is doing things like building new skills or challenging yourself in new ways. In the research, they’re called Mastery Experience.
That can mean playing a new song on the piano or trying out a new dish in the kitchen or entering a pickleball tournament. The key is to try something that stretches your skills and brings out challenges in you in a new way. A lot of times, when it comes to recovery, people think it’s time to slow down. It’s time to relax. A better approach is not to slow down, but to accelerate in a different direction.
That distinction between active recovery and other restful activities is an important one because most people lump it all together.
At the end of the day, we’re so exhausted. We just want to just do nothing and zone out. The challenge with the way that we’re zoning out is we’re exposing ourselves to new stimuli. It’s more processing and more thinking. The more scattered your thinking, the more difficult it is for you to feel like you’re restoring your energy. One of the more interesting findings in the research to me is how a leader’s recovery impacts the team’s performance that next day. That’s counterintuitive to me.
High Performing Teams: If there’s no decision to be made, cancel the meeting. Establishing strict team meeting guidelines protects focused work time and accelerates execution.
If you’re leading a team, and you go out with your wife dancing. Your team is more likely to perform better than the following day. Now, what is the way you recover has anything to do with the team? It’s because a well-rested leader is in a good mood. When the leaders are in a good mood, the team is more committed to their work and tends to do a better job. Far from thinking about this as just something extravagant. It’s like, “They recover better and good for them.” No, this is a pathway by which superteams become more effective.
There’s an emotional contagion that exists in any group of people. Workplace teams wouldn’t be an exception to that. If people come in energized and committed, the teams are going to do better work. The manager of that team probably has an outsourced impact on the emotional contagion within the team. My wife and I don’t dance, but if we did go out dancing, I would probably come in the next morning feeling energized and that’s entertaining.
Here’s another counterintuitive finding along the same lines of accelerating in different directions. We found in our data that on superteams, the leaders are more likely to be supportive of the employee moonlighting outside of work. That’s very counterintuitive. A lot of leaders think, “I want my employees to be focused on this job. I don’t want them taking on another job. That’s not good for them.” What we find in the research is that when people moonlight, or they take on a side gig, so long as they’re doing it for reasons of wanting to expand their skills and be good at something. That is energizing and leads them to be more engaged in their day-to-day job.
If they’re doing it because they’re struggling financially and they need to make ends meet. That’s not quite as effective for recovery. If they’re doing it out of passion or interest or curiosity, it’s beneficial. The best leaders are supported because what it goes to show is that the leader is authentically behind you as a person. They want you to succeed in life, grow and be energized. They’re not selfishly thinking about what’s good for them and their department. By contrast, if a leader does say, “You can’t do that. I’m not going to support it. I don’t want to hear about it.” That tells you that the leader is self-interested. It creates friction in the relationship.
Let’s talk also about trust. You have a fair amount of focus in the book about how these superteams build trust and some of the different practices that they use to do. Talk about some of the things that distinguish the way that they go about establishing and maintaining trust and how that differs from what the other 90% odd of teams are doing.
You might remember this. I didn’t write about trust in my first book, The Best Place to Work because I felt like trust was obvious. What I discovered while doing the research for this book is you have a lot of new interesting research about how trust gets built and how to sustain it. To build a trusting relationship is a skill, and anybody can develop that skill. It starts with understanding what the three factors are that contribute to trust in a workplace relationship.
Building Trust Through Competence Caring And Consistency
In Superteams, I talk about what those are. I call the three Cs. Its Competence, Caring and Consistency. The first one is competent. If you don’t feel like your teammate or your manager is competent at their job, you’re not going to trust them. Pretty obvious. That’s how trust is built. Trust is built on competence. The second thing is, it’s not enough to be competent. You also need to feel like they care about you. If that person is super competent but they don’t have your back or they’re selfish, you’re not going to trust them. You need both things.
The third thing is just as crucial and it’s consistency. If that person that you’re dealing with or your colleague or your manager is competent and caring but they’re not consistent. Sometimes they disappear for days at a time. You can’t trust them. The bottom line is, you need to focus on all three in order to build trusting relationships, and the challenges all of us fail at these at one point or another. It’s not because we’re bad people. It’s because we experienced a time crunch that makes it difficult to focus on all three.
The biggest example, and probably the least obvious is consistency. You might be a caring person. You might be a confident person, but if you are slammed, you’re not going to check your email for days. It’s a natural reaction to trying to prioritize and triage. What this research tells us is if you want to be a high-performing leader, it’s crucial that you respond to people consistently or to anticipate that busy period and say, “I’m going to be under the gun for the next few days. I may be slow and responding but you can text me if it’s urgent.” That rebuilds that consistency that might break in advance preventing people from distrusting you in the future.
I like that chapter in particular. What stood with me about it is that it doesn’t deal in the vague ideas of what trust might be. It doesn’t make the assumption that trust is obvious to everybody because to your point, there are specific things that we can do to build or erode trust. It’s important in a team to work at having the balance of those things skew toward the things that build trust. Again thinking from personal experience, a lot of teams put too little focus into thinking about the deliberate ways that they can build trust with each other.
I appreciate your point about not having very much that was abstract that you’re seeing my bias. If a term is like, even remotely abstract, it’s gone. My job is to entertain people and make it accessible. If I’m using an abstract word, then people are tuning out. I try hard to make this stuff relatable and actionable. To your point about trust, I do believe it’s a skill.
Once you understand that caring, competency, consistency are at the core, it becomes easy to build that trust. Especially at the beginning of a relationship, it’s like, “I need to demonstrate that I care about this person. I need to show my competence. I need to be consistent.” If you do that with a new client or a new colleague for a period of a couple of weeks, they’re going to trust you and it’s because you understand the formula and you execute it.
I want to zoom out and talk a little bit more about the macro level. Before we do that, for our audience that’s reading, if you are going to give them one or two key tips to drive near term performance of their team. Where would you tell them to start?
It depends on what the pain point is but let me use this opportunity to talk about where a lot of teams go wrong. That is, a lot of leaders don’t have an understanding of how you build a team mentality. A lot of people work in what are “teams,” but they don’t have that team mentality. It’s because they don’t attend to the three basics of forming that team mentality. Here’s what those basics are, and every team needs these.
You tend to see these more often in sports than you do at work. It’s part of the reason why we have so many dysfunctional teams. The first thing is, you need a shared goal. You need an outcome that everyone is pushing forward together. In sports, the shared goal is obvious. It’s a victory, but it works. It’s often not obvious. If I’m a designer and you are a copywriter. It’s not clear that we have a shared goal sometimes.
A lot of times, you have people who are sitting together next to one another for years and don’t know how their work contributed to one another. People need that shared goal. A lot of times also people have different goals at work. If I want to go home at 5:00 to drive my kids to soccer, and you’re trying to get a promotion. We’re going to have conflicting goals, then that’s going to lead to tension. The second thing you need once you have that shared goal, you need role clarity. I need to know what I’m responsible for. I need to know what you’re responsible for, and I need to know how those two things integrate to one another.
If we don’t have role clarity, we’re going to drop some balls because it’s your responsibility and you think it’s my responsibility or we’re going to have turf wars, because both of us claim the same responsibility. We need to be clear on what our roles are. The third thing you need is interdependence. Interdependence is just a fancy psychological term. All it means is we need to feel like we need each other in order to be successful.
High Performing Teams: Trust isn’t abstract, it’s a skill. By mastering competence, caring, and consistency, leaders build resilient and high-performing workplace relationships.
A lot of teams have competitor teammates. For example, if you have two salespeople and they each have their individual quota. Not only do they not have that shared goal or interdependence. They are now viewing one another as competitors. You need to feel like you need each other in order to be successful. When you have those three things, that shared goal, the role clarity, and interdependence, that’s when you create that team mentality. A lot of teams don’t have that. It’s why their teams are basically a recipe for dysfunction.
One thing you didn’t mention in that list was processes. I think about the grippy framework of why we have conflicts. Conflicts run goals, roles, processes or interpersonal relationships. You’ve covered goals and roles. Give everything you said about the importance of teams talking about how they work. Processes to come into the picture at some point, too.
I would subsume that under role clarity because the process is part of it. What I will say is, we’re not talking about creating a high-performing team yet. We’re just talking about how you create a team mentality. I need to know what my role is. Ideally, it’s part of a dial in process. In order to feel like a team, you can apply this framework quite easily. If you think about people entering an elevator, they’re strangers. They don’t know each other. They’re not a team.
The moment the elevator stops working, now they’re a team. What happened? They have that shared goal. That’s the key. It’s all about creating that team mentality. A lot of organizations don’t have that because it’s everyone out for themselves. We could talk about building trust until the cows come home but unless people have that team mentality, there’s no value to establishing trust. You need to start with the team mentality.
Come back to the tips that you give to people one or two things where to start.
For individuals, one of the things we looked at within our research on how high performing teams are managing to be so much more effective in terms of productivity was how they structure their hours at work. This is something that anybody can do as individuals, regardless of how your team is performing. It’s just getting more done and feeling more proactive with your day. By the way, that’s the key to having a successful day. It’s to feel like you played offense. You weren’t just playing defense reacting to people’s emails, phone calls and meeting requests. You got done what you intended to get done.
Part of how they managed to do that so effectively is they used some advanced planning. They time box. I talked about this as a framework of looking forward, looking backward and staying present. The looking forward part starts with Friday afternoon or Sunday morning. Look at your schedule for the following week and then take some empty time slots and indicate on your calendar. Set an appointment with yourself about what you’re planning to do during that time slot so it doesn’t end up being eaten up by someone else.
Set an appointment with yourself. Some people call this time boxing. That’s one of the keys to how high performing teams get more done. The second part is looking backwards. That means reflecting on how your time was spent. Part of this is people in high-performing teams tend to time track where the time went during the day to reflect on, was that a good usage? Was it a bad usage of time? What am I going to do differently next time?
Another part of it is, when you have a good day, here’s a simple way of doing it. If you’re not time tracking, when you have a good day, think to yourself, “That was a good day. How do I have more days like that? What can I learn from this?” Conversely, if you had a bad day at the office, think about, “That did not go. How do I avoid days like that in the future?” When you have that ongoing reflection, you’re going to get better with using your time more effectively.
The final point of staying present. When we are transitioning between tasks, that’s when we’re at our most distractible. If you think about when you check your phone, it’s when you’ve completed one task and you’re about to start another. The fewer transition points, the less distractible you become. If you’re able to, try to batch similar tasks together so that you have fewer transition points. You now have the formula, look forward, look backwards, and stay present. That’s how members of super teams get more done.
We’ve talked a lot about what individuals can do and also what a team should do collectively. At the organizational level, what would you recommend ahead of HR or people in culture or a CEO about how to apply what you’ve covered in super teams to their organization? What would you tell them to stop doing?
Selfishly, what I would like to suggest is that everyone get the free discussion guide for Superteams because it comes with the book. I’m going to do a little plug. At SuperteamsMasterclass.com, if you get the book, you get this discussion guide. What’s beautiful about the discussion guide is that it takes teams through each chapter and asks prompts for the discussion to happen so that you’re implementing the insights from the book as a team. Again, it’s completely free.
That’s a great place to start. A lot of the challenge for people on teams is that they’re not the ones in charge. It’s difficult for them to offer these changes. Even if they feel like they would work. If they were to say, “Why don’t we take a meeting free afternoon on Tuesdays?” It’s hard to suggest that sometimes because you feel like implicit criticism. What I often recommend people do is that they suggest the team run an experiment.
The reason I suggest framing it as an experiment is because it’s difficult for people to say, “We should not do that experiment.” The experiment tends to be more welcome because people understand that it’s not a lasting change forever. It’s a great way of introducing new ideas because even if they do reject the experiment, it still makes you look like you’re proactively trying to suggest an idea that could be helpful.
Now, in terms of leaders, there’s a lot that can be useful for leaders in this book. I would urge everyone to start with meeting guidelines. Have a discussion with your team about what are some of our best meetings. Differentiates those meetings from bad meetings, and then how we create some guidelines that everyone can try out for a week to see and do these to improve the way we work as a team.
Come back to this idea of what you would tell them to stop doing. How are organizations most significantly working against their own interests here?
One of the things that is worth mentioning is there’s a lot of confusion about effort and results. A lot of people think that the harder you work, the more successful you are at work. That turns out to be true to a point, and that point is generally 55 hours a week. The more you work past that, the more mistakes you’re going to make, the more errors and judgment. You’re going to focus on the wrong things. You end up spending more time correcting your mistakes than contributing valuable output.
In the book, I talk about how the best teams work to limit the amount of hours that people can work because they recognize that people are more productive with fewer hours spent past a certain point. I talked about things like how on Superteams, leaders are more than twice as likely to encourage their team to disconnect from work after hours. We talked about what they thought last time you and I spoke about one of the habits that leaders have is often they send emails after hours.
The challenge with that is that people are trained to respond to those emails after hours. It makes it difficult for people to recover their energy and they feel like they’re constantly working even when they’re at home. A good solution to this is not to avoid writing those emails but rather to schedule those emails to arrive at a later point.
You can do this on your email, on Outlook, or in Gmail, which is the to send later function so you can send your email at 11:00 at night and have it arrive at 8:00 in the following morning. You can even do this with your text by clicking the plus button on your iPhone. It allows you to send your text messages later. It’s a great little tip because what it allows leaders to do is to behave in a way that aligns with the culture they’re trying to build.
I’ll put one caveat on that from personal experience. Don’t match them all to go out at 8:00, Monday because nobody wants to get slammed with ten emails from somebody at 8:00 in the morning on a Monday. Last question. How is AI changing the way that superteams will work?
Leveraging Collaborative AI Practices
We just completed a new study on how AI is being used on super teams versus average teams. The results were interesting in terms of how surprising they were to be consistent with everything else we’ve said so far. On average teams, people hide their AI use from one another. They’re ashamed of it. They fear AI is going to take their job because they’re not sharing with one another how they’re using it. On superteams, it’s very different. They’re sharing not only their use of AI but they are more likely to share effective prompts with one another.
What that does is, it enables the entire team to get better as a whole because people are constantly learning from one another including their use of AI. On average teams, you find people are far more about losing their job. On superteams, they’re much less worried because they recognize that it’s helping the team improve together. You’re seeing how their contributions lift the team, and they feel like they’re team is getting better than other teams in their industry.
A good place to stop. There’s lots of practical advice here. Thank you for doing the discussion with me, and I would certainly heartily recommend your book to people that I know, because there is a lot of great practical guidance in it for lots of different aspects of team effectiveness. Thank you for that, and for the discussion, Ron.
Thanks for having me.
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There’s lots of practical takeaways from the discussion with Ron. Let’s highlight just a few of them. First of all, great teams aren’t built by accident. They are built with intention. High performing teams succeed not because they have the smartest people. In fact, having a team of the smartest people generally works against you and the research has shown that for decades. It’s because they create the conditions that allow talented people to do their best work individually and together.
The second point is that more collaboration isn’t always better collaboration. Endless meetings, constant interruptions, brainstorming sessions, always on communication, can undermine performance. The best teams know when to work together and when to protect time for individual focused independent work.
Third, the quality of your team shapes the quality of your work life. This is probably fairly obvious but it’s something that we all ought to be thinking about more. Exceptional teams create better trust. They create stronger relationships. They create higher energy, but they also create an environment where people genuinely look forward to coming to work.
Finally, AI is going to change how teams work, but it’s not necessarily going to change what makes them great. Technology will probably take over more routine tasks, but the human skills that drive exceptional teams things like trust, communication, judgment, creativity, and shared purpose will become even more valuable. As always, I invite you to subscribe to the show onApple Podcasts,Spotify, andYouTube. If you found the discussion enlightening, sign up for my membership community, which is called PathWise or our newsletterPathWisdom. Thanks.
Ron Friedman, Ph.D., is an award-winning psychologist who helps leaders build high-performing teams. He contributes regularly to Harvard Business Review, and has been featured in The New York Times, The Financial Times, Bloomberg, NPR, CBS, FOX, NBC, Fast Company, The Washington Post, Forbes, and Inc.
He is the bestselling author of The Best Place to Work and Decoding Greatness, and the founder of Superteams, Inc., where he delivers keynotes, develops leadership training programs, and advises senior executives on building stronger, higher-performing organizations.
The Rise Of Disposable Workers, With Paul Osterman
August 17, 2026
For decades, a good job meant stability, career development, and a long-term relationship between employers and employees. But according to MIT Sloan professor Paul Osterman, that social contract has fundamentally changed. In this episode of Career Sessions, JR Lowry sits down with Osterman to discuss the ideas behind his new book, Disposable Workers, and why more than one-third of today’s workforce now falls into employment arrangements designed for flexibility rather than long-term investment.
Together, they explore what’s driving this shift, why it extends well beyond the gig economy, how AI may accelerate the trend, and what individuals, leaders, and policymakers can do to build a future of work that benefits both organizations and employees. Whether you’re just starting your career or leading an organization through change, this conversation will challenge the way you think about job security, career development, and the future of work.
Key topics covered:
● Why Paul Osterman believes over one-third of workers are now “disposable workers”
● The difference between contractors, freelancers, marginal workers, and traditional employees
● What’s driving organizations toward more flexible—and less committed—workforces
● How AI is likely to accelerate the trend toward workforce disposability
● The costs of disposable work for employees, organizations, and society
● Practical advice for building career resilience through skills, networks, and smart career choices
● What business leaders and policymakers can do to improve the quality of work
The Rise Of Disposable Workers, With Paul Osterman
What does it mean to have a good job? For generations, the answer seemed pretty straightforward. A good job offers stability and opportunities to learn, a path for advancement in the sense that if you invested in your employer, they would invest in you. A lot of people don’t feel that way anymore. Whether it’s layoffs, contracting, freelancing, part-time work or simply feeling like you’re easily replaced, something fundamental seems to have changed and the relationship between organizations and the people who work for them.
The social contract doesn’t feel the same. My guest,Paul Osterman argues that the biggest shift isn’t the rise of the gig economy or even the threat of artificial intelligence in terms of job security. Instead, a lot of organizations are redesigning work around what he calls disposable workers. People who can do the work without truly ever becoming part of the organization on a long term basis. He argues that this trend extends beyond contractors and freelancers to include millions of people who technically have full-time jobs but aren’t being developed or invested in or given meaningful career paths.
Paul is a Nanyang Technological University Professor of Human Resources and Management at the MIT Sloan School of Management and one of the world’s leading experts on work employment and labor markets. His new book,Disposable Workers: The Transformation of Employment challenges many of the assumptions we’ve made about how work is changing and what it means for employees, leaders and organizations. I’m JR Lowry. This is Career Sessions. Let’s get to my discussion with Paul.
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Paul, thanks for being with me on the show. It’s great to meet you.
It’s a pleasure to be here. Thank you for having me.
Understanding the Rise Of Non-Standard Employment
You have a new book out calledDisposable Workers. It starts with a provocative idea that a lot of employers want disposable workers, not employees. Tell us what you mean by that.
Let me give you just a few examples to make this more concrete. Think first about the people who clean your office building at night. Those folks are building cleaners who are almost always working for a staffing company, a contracting company. They don’t work for the building. From the building’s point of view, these people are disposable. They can stop the contract and get a new set of cleaners. They could drive down wages by forcing contracting companies to compete against each other.
Another example of a contractor that’s a good job. Think about travel nurses. They work at some local hospital but they’re not employed by that hospital. The hospital uses them for a variety of reasons, but they pay them quite well on an hourly basis. Think about a freelancer. One example of a freelancer might be an Uber driver or a food driver. Uber or DoorDash treat these people as independent contractors, as freelancers. They don’t pay benefits. They don’t pay pensions. They don’t pay anything. That’s a tough job.
Think about the person who created the index from my new book. That person is also a freelancer. He doesn’t work for Harvard University press but they’re paid a good hourly rate. Think about a staff attorney. A staff attorney works at a law firm but they have no possibility of being on a partner track. They’re hired temporarily for a particular case. When that case is over, they’re typically let go. They’re employees of the law firm but they’re not on any career path or career ladder.
The same is true for adjunct faculty in universities. No chance of job tenure. They are on short term contracts. If the demand for their courses goes down, they are gone but they are employees of the University. Think about many part-time workers. Those folks may want to be part-time workers but also have much higher turnover. Turnovers built into the jobs. You’re never going to have a career in the organization.
Defining the Three Main Categories Of Flexible Labor
Those are all examples of disposable workers. They’re different categories. I identify these categories as contractors, freelancers. The third category, like a staff attorney and so on, are called marginal workers. I have a new survey of over 6,000 people and I could put numbers on this. When you add all those categories together, it turns out that 35% of the adult workforce are in these disposable jobs. That’s what we’re talking about.
That’s a pretty striking figure of 35%. Do you have a sense as to whether this is increasing? Do you have any historical data that would help substantiate one way or another, whether the numbers are rising or falling?
There’s no historical data that has the same degree of granularity detail that my survey does but I can look for example at employment in the staffing industry. Which are temporary help workers, manpower or Kelly Services. Those are all contracting jobs. If you look over time at staffing employment, it’s gone up. That’s one indication that it’s increasing.
If you look at other indicators for example, job tenure number of years that people have been with their employer. That’s shown a decline over time, which also suggests that there’s an increase in disposability. My survey is the first survey that has the detail that enables you to extinguish all these categories. There’s evidence here and there that it’s increasing.
I think about some of the trends I’ve seen. Certainly, we’ve seen the rights of the gig economy. We’ve got platforms to match buyers and sellers of services all over the place but thinking about some of the categories that you mentioned, it’s more than that. From a corporate perspective, what’s driving this ship?
Why are firms wanting to do this? I have evidence that there’s a cost to firms who are doing this, which we can talk about later on what the consequences are. Firms pay some price for doing it, but there’s a series of reasons why they are doing it. One is crude cost. In the sense that, if you’re an employee of the firm, the firm has to pay a portion of your Social Security and all the states, into unemployment insurance.
Analyzing The Economic Drivers Behind Corporate Restructuring
It’s required to pay into workers compensation programs. There’s a set of benefit costs that firms can avoid if they don’t have employees but instead, they have people doing a job for them but are not employees. There’s also a set of management costs that managers don’t like. They don’t like to be constrained. Managers want to manage, so equal employment opportunity, sexual harassment, difficulty in laying people off just at the drop of a hat.
With a contracting firm, you just call up the firm and say, “Contracts over.” With a regular employee, there’s often complications with how you lay them off. It’s not that you can’t, but you have to jump through some hoops. There’s also managerial attitudes. In the book, I have a quote from McKenzie. McKenzie did a report they called the state of organizations in America. In that report, they assert that in firms, 95% of the value of the firm is produced by 5% of the workforce.
In other words, the rest of the workforce is not important. I have severe doubts as to the quality of McKenzie’s research, but setting that aside, think about the attitudes that underlie a statement like that. You see that in other ways. You see the failure of what we call high commitment or high-performance work systems to diffuse at us, say the Toyota systems, in which frontline workers are given a lot of responsibility for production and quality.
Those have not diffused in America, despite a lot of research showing that they are highly productive. The reason is managerial attitudes towards the workforce and then, of course, is what you could call a benign explanation when you can respect. Which is that there’s an up and down and a demand for labor and some firms feel they need to have flexibility to adjust quickly to that. Those are the reasons.
The other thing that comes to mind, for me, is what I’ll call and others, call the financialization of the economy. This idea that we are so focused on earnings and shareholder value that other constituencies, including employees, aren’t given the same weight. We’re constantly trying to squeeze as much profit out of businesses. Therefore, you want this flexibility to be able to move your costs up and down as you need them. that I’m sure factors into all of these as well.
Firms are profit maximizers and any argument otherwise is it relevant. In the book, I use an analogy which is sharks. If you think about sharks. Sharks are a good thing out there in the ocean. They’re part of the ecosystem and they keep the oceans healthy. We want sharks, but sharks have only one interest in life and that’s their next meal. We put fences around sharks and barriers.
Establishing Boundaries To Support Quality Jobs
A firm, at the end of the day, has only one interest, which is maximizing profits and they are intensely focused on this for the reasons you described. Now, that’s a good thing. Firms create jobs. Firms innovate products. We want firms, but we have to put fences and barriers around them, too, If you don’t do that, then you have this explosion of disposability and it has negative consequences for the workforce. That’s part of the story.
You talked earlier about the fact that there are some costs of doing all these things, too. Do you want to get into some of that?
Disposable Workers: Proactive skill development and strong professional networks serve as vital career parachutes.
Sure. From the point of view of the workforce, I look at earnings and I look at job satisfaction. The good thing about using jobs satisfaction is an outcome, encompasses earnings but also working conditions. I compared the job satisfaction rates of standard workers with contractors, freelancers and with marginal workers. Contractors and marginal workers are substantially less satisfied with their job than our standard workers.
Freelancers on average are more satisfied. The reason is they get flexibility. The person doing the index from my book can decide not to work today if he or she doesn’t want to. They go into that for that flexibility. In terms of earnings, all three groups, contractors, freelancers and marginal workers earn substantially less even after controlling for education, for age, and all the things you’d want to control for. They earn much less than standard workers.
There’s also a cost to the public at large and a good study of hospitals. Researchers found that the more contractors at the hospital uses for cleaning as opposed to their regular employees, the higher rate of infection in that hospital. They attribute this to communications problems between management and contractors because there’s a layer between them that staffing is from.
Measuring The True Cost Of Disposability On Performance
There’s also evidence that the more contractors there are in an industrial setting, the higher the accident rate. There’s a public consequence to that. There is a consequence for firms, which is that my data show that contractors and marginal workers are less committed to the organization for whom they work. They are less willing to put in extra effort. They told me that in the survey. Firms think that that’s a cost that they’re willing to accept and return for all the other quote benefits that they get from this.
If I’m a C-level leader in an organization and I’m reading all of this. Is the answer that you get back when you present this to corporate leaders like, “Yes, but we’ve got to maximize earnings?”
You get back two answers. One is the rhetoric, “Our workers are our most important asset.” If you look at their behavior, you see that they’re doing this. The point of my survey and the interviews I conducted was not the focus on the rhetoric, but the focus on the behavior.
For the companies that aren’t doing this, that are continuing to invest in their workers, continuing to give their frontline employees a degree of autonomy and responsibility. Do they jump in the scheme of things or are they optimizing for a different set of conditions?
That’s a very good question. There is a substantial amount of research on what’s called the high road in employment. On the high road, our firms do exactly what you described. It turns out that most examples in the advocacy literature about higher road as well as a researcher are idiosyncratic. They’re either founder-led firms in which the founder has a set of views or values that he or she wants to implement or their next generation founder run firm. Costco is a classic example.
There are firms like that, and those firms are willing to accept some diminution of their profit margin and return for treating a workforce better. It has not defused in the economy as a whole because it’s clearly more profitable to squeeze. Companies do that. As I say, this is not a book that says they’re bad people. They are what they are. They’re doing what they should be doing, but then you have to build fences and barriers or, in my case, you have to put floors on the quality jobs.
Talk about what those might look like fences, barriers, floors.
It’s very complicated because one set of issues is for freelancers like the Uber drivers and so on, defining what it means to be an employee. If you’re an employee, you do get a set of protections. That’s the debate that we’ve been seeing about Uber, but it’s extending into other services. For example, Amazon is now making a lot of the delivery drivers into freelancers. It’s a legal question and/or regulatory question.
The legal standards and the regulatory standards about who’s an employee has vacillated depending on whether we’re talking about a Republican or a Democratic administration. President Obama expanded the definition of strength and the definition of employee. Trump won and weakened it. President Biden expanded it. Trump too has weakened it. You need to try and nail this down. Now, over 30 states have passed their own definition of employee for state programs, such as unemployment insurance or workers comp.
They have a simple set of rules that are easily understood. In an ideal world, we’d adopt this with so-called ABC criteria for finding an employee. None of that is relevant for contractors and marginal workers because they are employees. The contractors are employees of a staffing firm and marginal workers. Although, there is no career ladder for the employees of that company. There, you have to create floors.
Now, the most reliable way of creating a floor under job quality is unionization. As you know, only 6% of the workforce is unionized. Unions are having a hard time growing that number. Absent unionization and what’s possible. One is work pressure, that’s non-union work pressure. You do see that. For example, the fight for fifteen and big box firms had an impact in the coastal States of New York, California, and Massachusetts.
Rideshare drivers have been able to organize in a non-union way to put pressure on the companies and to get state regulations to create that floor. A classy example for contractors is justice for janitors, which occurred in California in which building cleaners organized not in a union but with some union assistance to put pressure on building owners to insist on standards and requiring employers who use staffing firms to put standards on the quality of jobs offered by the staffing firms is the strategy. There’s no single answer to this. It’s a complicated question. You do want to do it in a way that gives firms the flexibility that they legitimately need. You’re striking a balance. I’m not trying to make disposability illegal and possible but I’m trying to put some boundaries around it.
Listening to all of this, I know you work hard in your book not to portray corporations as villains. If I’m an individual, this feels pretty awful. It feels like things are stacked against me, especially if I’m living a little bit more in the Edge from an economic perspective.
Disposable Workers: Lower commitment and communication gaps are hidden organizational costs of disposable staffing models.
Absolutely. There are negative consequences for people and young people entering the labor market. There’s a lot of fear about AI, but I should note that this is not a book about AI. AI is going to make things worse, but this trend precedes AI. People entering the labor market are mature workers who find himself in this position. They’re paying a price. It feels terrible. Except if you’re a travel nurse. When you’re making $80 or $90 an hour and you get to live in some warm place in the winter and work. It feels good. There’s heterogeneity.
We didn’t get into this yet, but you have to cross those categories contractors, freelancers, etc., to some degree of people who are doing this by design or by choice. You also have people who are doing it by necessity because other options aren’t available to them. A travel nurse is a great example of somebody who may say, “I like to move around. I want to see different parts of the world or different parts of the country. This is a way to do that. I’ll take the contractual nature of it as a trade-off.” The same might be true of an adjunct professor who wants the flexibility and doesn’t want to do research and all the things that come with being a tenured professor. You get people who are only doing this because it was the only thing available to them.
The point, though, is that the data showed that on average in these categories, it’s a bad thing for folks, even though there’s heterogeneity. You don’t have to worry about a floor under a travel nurses’ job. We don’t have to worry quite as much. There are complaints. Those folks could get standard employee jobs his nurses. They’re doing it voluntarily. On balance, it is bad news for people. We don’t want to extend and expand and we all want to put floors under it.
For somebody who’s reading who’s at the beginning of their career and thinking about how this all will affect them. A lot of Gen Z people are struggling with the work world and the work environment these days. What advice would you give them for thinking about their options and for figuring out whether they’re on a path that has longevity to it or they’re just going to become one of these disposable workers?
Navigating Career Risk In An Uncertain Market
One piece of advice is to make sure that your human capital, your skill level is as high as you can reasonably make it. That gives you power in the labor market. If you have a set of skills that employers need, but be very careful about for whom you go to work because firms do vary in their utilization of this thing. You can look at websites such as Glassdoor that will help to assess the firm that you’re looking to or talking about, to the extent possible.
Maintain your networks, so that if you are forced to leave a job or look for a better job, you have as many options as you possibly can have. Now the problem with everything I said is that they sound a little high end-ish. That is to say, it sounds like I’m talking about people with a college degree who can maintain external networks and can look at Glassdoor regularly and so on. For people with lower education, lower skill levels who find themselves in his jobs and it’s very common for them to do. These jobs are often biased towards people with less personal labor market power. There, it is going to be a question of public policy to try and create floors.
I think about the fact that if you are somebody who is more at the lower end of the economic spectrum and struggles more with all of this. Everything that surrounds it like lack of access to health care, lack of savings, all the things that you have to do if you become a freelancer from a tax perspective. It’s an incredibly complicated thing for even somebody who’s very capable and savvy about this to manage. If you’re not, it feels almost impossible for them to be able to keep up with all of these regimes.
That’s right. That’s why this rhetoric is to pack your own parachute. We’re in a brave new world and isn’t it wonderful? That’s rhetoric. That’s not a day-to-day reality that most people face.
You talked a little bit a minute ago about AI. To what degree do you think AI is going to make this a more prominent factor?
There’s two issues about AI. One issue is, what’s it going to do to employment levels? Are people going to lose their jobs and so on? There’s a lot of debate about that and no one has any idea. My interest in the context of this book is what’s going to do to this trend towards disposability. There, I’m pretty confident that it’s going to increase.
Evaluating The Impact Of Automation On Staffing Decisions
The reason is that because no one has any idea and firms don’t have any idea either, they’re going to be even more leery about hiring more standard employees because standard employees are costly and create bureaucratic issues for them. They’re going to be more interested in having a more flexible workforce via having more disposable workers. AI will intensify what we’re talking about here because of the uncertainty it creates for companies about their staffing needs.
If you go back, we had the Microsoft case that created a framework of sorts for how to think about contract workers and the fact that over time, they crew the status of an employee. As you said, I went back and forth a little bit on that. Do you see companies rethinking the mix of employees versus these contract workers? I have not experienced that. I’m just curious what your research shows.
If you look at the examples of Amazon or FedEx, you do see a push even away from contractors, and towards freelancers to the extent that they can. They run up against lawsuits regarding employees data, space on the Microsoft case, and other. Firms are seeking to have as much flexibility and as few regular employees as they can. They’re following the number of strategies. The rhetoric of all becoming gig workers is wrong. The rhetoric that we should care about is Uber drivers, not just because of Uber, but also because other companies are pushing the boundaries as much as they can is right.
Now, there’s another thing that’s going on which is weird misclassification in which companies simply cheat. They don’t pay benefits. They don’t pay unemployment insurance. They don’t pay workers comp and so on. I talked about that in the book. It’s a phenomenon. It’s real, but I don’t think that’s the main story. For certain, it’s occupational categories, but it’s not the main story.
It’s always hard to separate the anecdotes from the macro reality. We hear the stories of Uber and Amazon. Certainly, they are both big employers, if you want to think of them that way even though a lot of their workers are contract people. They’re big employers of people but they’re only a few companies in the scheme of things. You hear the limited examples of people who are outrageously cheating when you’ve got the whole rest of the economy. It’s always hard to know how prominent all of these things are in the scheme of things.
Misclassification is real, but the way it works is people are put into independent contractor or freelancer status. On average, my data show freelancers are happy campers. There are exceptions. It’s true in the case of Uber. It is true that roughly 2/3 of Uber drivers want to be part-time. They want flexibility. It’s not important to them that they be employees.
Disposable Workers: Disposable work extends far beyond gig drivers to include corporate attorneys and university faculty.
There’s nothing in the law that prevents Uber to make people employees and then give people the flexibility to be part-time if they want to. The law doesn’t block part-time employment. Uber’s argument that if you make people or ease, they can’t have the flexibility that they want. They could be employees and have that flexibility if Uber wanted to do it. It’s a complicated story. That’s why policy is complicated. It’s not all a piece of one or the other.
We’ve talked a little bit about some of the policy angles. What are some of the other things that we ought to be thinking about from a public policy perspective?
This is stepping outside my area of expertise. The big issue is developing a political constituency for improving the quality of work. A lot of people are suffering from low quality jobs. Not just these disposable jobs, but other jobs which are regular standard jobs, but have poor quality. If there was a constituency about addressing job quality and workplace fairness, then it would be much easier to talk about what policies and how to implement them.
It’s one thing for you and me to have talked in the abstract about this law or that regulation, but making it happen and developing support for it. That’s a problem. That’s not just an issue with Republicans. It’s also an issue with Democrats. If you look at a support for Uber or the opposition to improving labor law, a lot of it come from democratic politicians, as well as from Republican politicians. That’s the big question, is, can job quality become a salient political issue?
Beyond policy changes, what can leaders and organizations do to change the dynamics? Do you think that will happen?
I don’t think it will happen without outside constraints. Look at what’s happened with DEI, equal employment opportunity or environment. A few years ago, every CEO in the country, particularly after George Floyd, was talking about how DEI, equal employment opportunity is a high value, important value for the company, central to their mission, ditto on the environment and now, it’s silent on it. They are about what we’ve talked about earlier. They’re about maximizing profits. End of the story. Now, as I’ve said, that’s not a bad thing. I support that. You need to put barriers and fences. I’m not looking for corporate leadership to push on this.
Where does that leave you overall about the next 5 to 10 years in terms of the economy and the world of work?
That question is not an economics question. That question is a political question. Does the political environment shift in a way that makes these issues important to politicians to do something about? If it does, we have ideas. I have ideas. Other people have ideas. We could have a discussion about what to do. If the environment political environment doesn’t shift and the stuff does have become salient, then we’re all talking abstractly.
Any last advice for an individual reading about things that they ought to be thinking?
To the extent, you can maximize your human capital and your external networks.
It’s an advice that I give a lot to people. Thank you for the conversation. It’s certainly is a thought-provoking one given everything that’s going on. As we’ve talked a little bit about a lot in the markets, and the news about but AI, but as you said, all of these things precede that and this is a longer term trend. It will be interesting to see how this plays out to say the least.
Thank you. I’ve enjoyed the conversations. It’s a good conversation.
I appreciate your time as well and I wish you luck with the book. When’s the book coming out?
The publication date is August 11th, 2026, but you can order it on Amazon now and get it.
Thank you for your time.
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What do I want you to take away from my discussion with Paul, first is this idea that job security isn’t just about having a full-time job. Interestingly, when he looked at this idea of disposable workers, it isn’t a discussion of freelancers and contractors, the gig economy, so to speak. Also, between people and an organization who are being invested in, have a future and a career path and the people in an organization who don’t and are there for more disposable.
Second is an idea that flexibility has value, at least for some people. It does come at the expense of feeling like you truly belong in an organization. Some people genuinely prefer contractor freelance work. Organizations are always going to have a need for flexible talent. They’ll certainly exploit the opportunities to hire people in a more flexible arrangement. The challenge is seeing the trade-offs career development, mentorship, organizational knowledge and advancement often come from being part of a system that’s committed to your long-term success. Not just your current assignment.
Third is if you are an individual, you need to be taking ownership for your career. It’s something I talk about a lot both within the podcasts and more generally. That means having a network, continuing to learn, building your skills, making sure that you’re making good career choices as best you can and having savings. All of those things that give you the ability to take ownership have agency in your professional life and not have it being done to you.
Fourth, this gets to the policy points of what Paul talked about. We have to make the future of the work world what we want to be. We talked about the Fact that there doesn’t feel like there’s a strong political constituency now to shape the future of work in a way that feels a bit more employee oriented. That doesn’t mean we need to go back to the days of having a huge union workforce in the United States. We probably do need to use his words different guardrails, fences and floors.
If this matters to you, look for ways to make your voice heard. Whether that’s talking to your Congressional Representatives, or advocating at the state level, or even advocating within the organization you’re in. It was a very thought-provoking conversation. Much to think about from this. Again, I appreciate the Paul was able to join and I appreciate the opportunity to have read his book as well. As always, I invite you to subscribe to the show onApple Podcasts,Spotify, andYouTube. If you found this discussion enlightening, you can join by membership Community, which is called PathWise or you can sign up for our newsletterPathWisdom. Thanks.
Paul Osterman is a Professor Emeritus of Human Resources and Management at the MIT Sloan School of Management as well as a member of the Department of Urban Planning at MIT. From July 2003 to June 2007 he also served as Deputy Dean at the MIT Sloan School.
His research concerns changes in work organization within companies, career patterns and processes within firms, economic development, urban poverty, and public policy surrounding skills training and employment programs.
Osterman has been a senior administrator of job training programs for the Commonwealth of Massachusetts and has consulted widely for government agencies, foundations, community groups, firms, and public interest organizations.
His most recent book is Disposable Workers: The Transformation of Employment (Harvard, 2026). Other recent books include Who Will Care For Us: Long Term Care and the Long Term Workforce (Russell Sage,2017); Good Jobs America: Making Work Better for Everyone (Russell Sage, 2011); The Truth About Middle Managers: Who They Are, How They Work, How They Matter (Harvard Business School Press, 2009); Gathering Power: The Future of Progressive Politics in America (Beacon Press, 2003),; Securing Prosperity: The American Labor Market: How It Has Changed and What to Do About It (Princeton University Press, 1999), and Working In America: A Blueprint for the New Labor Market (MIT Press, 2001).
Osterman is also the author of Employment Futures: Reorganization, Dislocation, and Public Policy; Getting Started: The Youth Labor Market; The Mutual Gains Enterprise: Forging a Winning Partnership Among Labor, Management, and Government; and Change At Work. He is the editor of two books, Internal Labor Markets and Broken Ladders: Managerial Careers in the New Economy. In addition, he has written numerous academic journal articles and policy issue papers on topics such as labor market policy, the organization of work within firms, careers, job training programs, economic development, and anti-poverty programs.
Why Smart People Get Financially Stuck (And How To Break Free), With Carrie Joy Grimes
August 10, 2026
Most people were never taught how to manage money. Yet they’re expected to navigate rising housing costs, student debt, investing, retirement planning, and an economy that often feels stacked against them.
In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Carrie Joy Grimes, founder of WorkMoney and author of the USA Today bestselling book The Joy of Money, to explore why financial success has far more to do with psychology than spreadsheets.
Carrie explains why shame and avoidance keep so many people financially stuck, how small behavioral changes compound into long-term wealth, and why the biggest obstacle to financial security often isn’t a lack of knowledge—it’s the stories we tell ourselves about money.
They also discuss:
Why “I’m just bad with money” is one of the most damaging beliefs you can have
The surprising connection between money habits and career success
Why budgeting should create freedom—not guilt
How to overcome financial avoidance and build confidence one small step at a time
Why chasing the next hot investment rarely beats mastering the fundamentals
How to think about raises, retirement savings, and building wealth in today’s challenging economy
Whether you’re just starting your career or trying to gain greater financial confidence after years in the workforce, this conversation offers practical, encouraging advice that can help you take control of both your money and your future.
Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.
Why Smart People Get Financially Stuck (And How To Break Free), With Carrie Joy Grimes
Even with a stock market near all-time highs as we record this episode, a lot of people are feeling pretty gloomy about the economy. The cost of living keeps going up, becoming a homeowner feels increasingly unreachable to many, and a lot of people feel financially stuck. Moreover, they feel financially insecure. It’s not necessarily related to how much they’ve scrolled away, but due to the sense that they’re not good at managing their money, as if they somehow missed out on a magical money gene that everybody else got.
Here’s the thing. Most people were never taught how to manage their finances, and then they get dropped into an economy that’s often designed to profit from their confusion, debt, and financial anxiety. That’s where my guest, Carrie Joy Grimes, comes into play. Carrie is the Founder ofWorkMoney, a nonprofit with millions of members, nine million members, focused on helping everyday Americans build financial security.
In her new book,The Joy of Money, which made the USA Today bestseller list, she makes an argument that some people think sounds simple, but it’s pretty radical. You can be good at money, and you can learn to become good at money, even if you grew up in chaos, even if you avoid checking your bank account, made financial mistakes that you’re still trying to recover from, and shame has convinced you that everybody else out there somehow understands money better than you do.
The conversation that we’re going to have is much more than about budgeting tips or cutting back on gourmet coffee. What we’re going to be talking about is the psychology of money, why shame and avoidance keep people financially stuck, why traditional financial advice often fails ordinary people, and how building financial security is as much emotional as it is mathematical.
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Carrie Joy, thanks so much for being on the show with me.
Thanks for having me. I’m excited to be here.
We are going to talk about a very important topic, which is how you manage your money and build wealth, particularly in a very uncertain world and uncertain economy. A lot of people don’t see themselves as good with money. You have said you saw yourself as one of those people. What was the turning point for you that led you to realize that you could learn this stuff?
Shifting Your Money Story
This is going to maybe sound hokey, but it’s very true. I decided to let a choice I made change my life. I ended up backing into a lot of behavioral science about behavior and money. What happened is I had gotten myself into a little debt with my boss. I showed up on my first day of work at this job. It was my first big professional job. I was working poor at the time, so I didn’t have great shoes, and I couldn’t afford to eat out.
The team was going out for dinner that night, and it was one of those mandatory works that you had to go to. It was my very first job, and I hadn’t gotten my first paycheck yet. If you all can remember back in those days, I didn’t have the money for a big dinner out yet, and I didn’t have the money to upgrade my wardrobe. He said, “You got to go.”
After dinner, he paid for my dinner, and then he gave me $100. He was like, “This is for some shoes.” That was the most mortifying thing to have a man that you work for give you money. He wasn’t wrong, but I did not want to have that feeling ever again in my life. I’ve been in debt before, but that felt serious. I ended up paying him back in a few weeks.
That experience where I could pay him back, I was like, “That was some good money behavior. What if I’m good at money?” I had been telling myself for years I was bad at money. Everything and every mistake I’d made was more evidence that I was bad at money. I had this intensive period where I said, “If I can do that with him, I could pay off this credit card.”
I took that same mindset, and I was pretty ruthless with myself. I had a whole new money story. I was like, “I can be good at money. I can do it.” I tried to catch myself doing something good. I worked it pretty hard. That process built the muscles and the neurology for me that I could. That changed my money life. It led to a whole bunch of different learnings and experiences. I got into the science around all of it, like, “Why did that work? What was different about that time?” That was my experience. I let a random plate of barbecue change my money life.
We’ve all collectively discovered behavioral science, whether we got it from Malcolm Gladwell, the Heath Brothers, or Daniel Kahneman, if you wanted to go deep into the Nobel laureate version of behavioral science. Since it’s so out there and it’s so entrenched, once you understand it, you realize how entrenched it is in the way that people market and advertise to us. That includes the way they market and advertise to us about how we save and spend our money. If you’re not tuned into it, at least at enough of a level, you’re going to get manipulated by it. That’s a key thing you’ve got to understand.
That’s super right. Many of us didn’t grow up with clear conversations or teaching about money. There are these financial literacy or education classes in high school, which are great, but the way we learn money is mostly through our families of origin and the culture around us. There’s not a lot of substantives, reliable, good information that people have access to as they’re growing into their money lives. There’s tons of information out there. You can hit the internet, but it’s hard to tell good from bad in some cases.
A lot of people I talk to have this vague sense that they’re doing something wrong, and they feel ashamed of themselves for it. Those two things, what you said, are so important. Those are the pain points that a lot of companies take advantage of to increase people’s spending or get them to use financial products that are probably not a good idea. Learning how you are with money is such a great first step to not only making better choices yourself, but being able to resist the pretty powerful forces of psychology and advertising that are pulling us in directions that aren’t always good for us.
That’s true. To your point, a lot of times, you get tricked, for lack of a nicer way of saying it, into believing that you need something that’s more complex than what you need. For most people, it’s to live within your budget, pay down your debt, and save a little bit each month. People think, “I’ve got to go invest in crypto.”
We could probably have a whole conversation about all the get-rich-quick schemes that are out there, whether it’s investing in AI, tech stocks, prediction markets, crypto, or whatever. There’s a lot of that that’s been going on over the last couple of years or so. In my coming-of-age era, if you weren’t working on a dot-com something, you were an idiot. I was working at McKinsey at the time because I needed a paycheck. Everybody believed that they were going to get rich. A few people did.
Most people ended up working in companies that were failing. It’s like having a cheat code. It’s like, “I want a cheat code that’s going to allow me to get fabulously rich without ever having to work at it.” It’s very harmful to people’s psyches. There’s a lot of that going on that makes people think in many of the wrong ways about how to think about their career and also how to think about their financial habits.
Mastering Personal Finance Basics
That’s such a good way to say it, too. What’s interesting about money is, you’re right. I say this thing all the time, which is that money is not rocket surgery. It’s not that hard. For most of us, the basics are the things to do to make us wealthy. The biggest problem most people have is they don’t make enough money. That is something that is dealt with through education and career advancement. There are lots of ways we can talk about how to get more coming in. That is the biggest problem most people have.
The next biggest problem is that when people do look at their money, it feels very confusing, and it feels like it’s unclear what to do. That one is a great problem because it’s very solvable. It is having a budget. It is getting out of high-interest debt. It’s having 3 to 6 months saved up so that you don’t have to borrow expensive money to solve problems. Everybody gets problems in their life. It’s maxing out your tax-advantaged retirement accounts.
The money that people can make by maxing out their 401(k), their 403(b), or their IRA is so much more money than they’re going to make by taking risks with different individual stock investments. I’m a stock picker. I don’t do very much other than target date funds and put a lot of my money into index funds. Frankly, this is Warren Buffett’s advice. Warren Buffett is the only person to run a fund that beats the overall stock market for many years, except in the last couple of years.
Warren Buffett did not beat the stock market himself. In his will, when he passes away, he leaves his money to his wife. Ninety percent of his money is directed in the will to go into an S&P 500 tracking fund, an index fund that tracks parts of the market. I don’t think of myself as being a better investor than Warren Buffett. I don’t think most people in the world are better investors than Warren Buffett.
I always say that if you have special knowledge in an industry, or you understand a product or a service in a way that gives you an advantage, that’s one thing. If you’re like most of us and you’re trying to figure out, “How do I build wealth? How do I get myself to a good retirement?” The answer is pretty clear. It’s budgeting. It is taking a 401(k) match if you get one from your employer. It’s getting out of high-interest debt. It is saving up 3 to 6 months in an emergency fund. Finally, it is figuring out how to max out all of your tax and retirement accounts. After that, that’s when individual investment choices become clear.
The number of folks I talk to don’t understand how much more you make because of the tax benefits. They’re like, “Why shouldn’t I go after this stock or that one?” I say, “Have you done the basic, like maxing out your 401(k)?” They’re like, “No.” I’m like, “Let’s put your money there first.” Especially folks who are professionals who are figuring out their careers, I don’t know about you, but I remember all the paperwork, the HR lady telling me about all the things, and being like, “I don’t know how much to take out of my paycheck.” It is worth figuring that out first and checking the boxes.
Especially if you get a match from your 401(k) employer, it’s free money that you don’t otherwise get unless you opt into that. You’re never going to have a chance to get that free money again if you don’t opt into it year after year.
It’s part of your paycheck. Not taking it is like voluntarily taking a pay cut. This is so crazy. I did the math on this. There are some financial people out there who will say, “You should eat rice and beans and pay down your credit card debt. You should have no joy in your life. You should treat yourself like a prisoner in your own house.” I’m a big believer in getting out of high-interest credit card debt. Let me be very clear. The math on this is fascinating.
Maximizing Employer Matches
If you get an employer match, if you take that free money, and you put that free money into your 401(k), you are going to make more money than you would save by paying down your credit card debt. It’s one of the few things I tell people that they should be doing before they tackle the high-interest debt because you end up with more at the end of the process than you went right to debt. Folks who are professional people who work in businesses where your employer offers a match, the benefits of it are not that understood by most people. The compounding interest effects of that are so powerful that they beat what you end up owing the credit card company, which is crazy.
I will share an example. I’ve shared this with my kids and my wife before we were married. If you put $2,000 into an IRA many years ago, that’s now worth over $100,000. It was not invested in crypto. It was not invested in tech stocks. It was invested in a large-cap growth fund. It rolled. This is the power of compounding. It’s worth 50 times what it was before.
When people talk about the importance of saving a bit in your 20s, if you’re doing that in your 20s, you get 10 years of that compounding that you don’t get if you don’t start until you’re near your 30s. All of this, to your point, is not rocket science. It takes a bit of discipline. If you try to throw too much discipline on yourself, it’s not going to work because it’s a starvation diet.
Removing Guilt From Your Budget
I remember there was a study a while back that said that one glass of red wine is not the end of the world for your health. Everybody was drinking red wine all the time. A new study came out and was like, “Alcohol might be worse than we thought.” This is going to sound like that because it’s going to sound like I’m giving people permission, but the behavioral science on this has been repeated many times. Folks are much more likely to stick to a budget if there’s a little bit of joy in it or a little bit of a reason that that’s what the money is for.
I always say to people, “Treat yourself reasonably. Have something that you can afford that makes life a little bit more enjoyable within the bounds of reason.” That’s not because people should live good lives, although I do think that, but it’s also because the science on this is pretty clear. You’re more likely to stick to something if you’ve got a little bit of a reason to keep going.
It’s interesting because there are a couple of things I say that are not popular with other financial experts because they don’t follow the shame-based advice trail of like, “You’re the problem if you’ve got problems. It’s you. You are the problem. You should be punishing yourself for doing these impossible-to-continue behaviors.” When you don’t succeed, you have to go back to those financial people for more help.
There’s this cycle of a lack of success that breeds more engagement with financial experts that is a disincentive for people to succeed. It’s part of why I wrote the book. It’s because I got so frustrated by what was out there. I run a big organization of nine million members. It’s about how people do better with their money. It’s a nonprofit. It’s like the AARP, but about money for people. You can be any age. We don’t send you an envelope when you turn 50. That makes you feel old. It’s a little different.
My daughter started college. She finished her first year. She’s becoming an adult. I had this moment as a mom where I realized this economy is even harder than the economies that we’ve all been in. I’m Gen X. It wasn’t easy for me, but it certainly was not this volatile. I had this moment where I realized I wanted her to have something that would give her a roadmap.
Over the last few years of talking to nine million people, where we text, email, and call people weekly, I’ve had so many conversations where, over and over again, it was the same stuff. I was like, “It’s time to put it down on paper or a source where people can trust that the person writing it has their interests at heart.” That’s why I wrote the book. It’s not that complicated. It’s not always easy, but it’s not complicated. People have the right to understand how they can build wealth.
Your book is not called the Masochism of Money. It’s called the Joy of Money. You’re clearly trying to play more of the upside. It coincidentally gives you an opportunity to throw your middle name in there. I saw what you did there.
I see you see me.
Talk a little bit about what you lay out in the book. You’ve got a number of lessons you want people to learn as you progress through there. Give us a quick fly-by.
There are four big quick fly-bys. The first one is that your mental framework is fundamental to your financial success. I don’t mean Stuart Smiley, for those who know what that is from Saturday Night Live. I’m not saying that you can magic yourself into a bunch of money skills. It does take work, and it takes trying things. I do mean that if you don’t think you can hit the ball, you are not going to hit the ball.
The first thing everyone should be doing if they want to get their money life in order is deciding how they want to imagine themselves as successful and how they get there. I don’t mean a bubble bath and some nice music in the background. I mean you say to yourself, “I can be good at money.” It’s like an athlete. Figuring out the story that you want to talk about yourself and how you’re going to reinforce that over time is important.
The second big lesson for me that resonates with a lot of folks is that money is math, and it’s also feelings. The math part is evident. We all know the right thing to do or the best thing to do, but a lot of times, we aren’t doing it. It’s not because we’re crazy, lazy, or stupid. It’s because there’s another driver in the car, which is feelings.
You’ve had a hard week, and your budget has been cut to the bone. You don’t have ordering out in your budget, but you do it anyway, because shouldn’t life have one good thing in it? All your friends are taking a vacation. You don’t have the money for that, so you put it on the credit card because you don’t want to feel left out. These are normal human decisions.
I always say that it’s not that you should figure out what those feelings are so that you can kick them out of the room. It’s knowing what those feelings are, how you feel about money, what might come up that’s going to be meaningful to you, and building your budget as best you can, including those moments and those feelings. I would argue it’s way better to have all of you in the conversation and the plan than it is to try to be a robot about it. That’s both my personal preference, but also, it doesn’t work long-term to ignore the needs and wants that come with being a human being. Figuring that out is an important part.
I think about the stories I’ve heard from people who say, “I grew up without a lot of money, but we always went out on Saturday nights. It was a simple meal. We didn’t go anywhere fancy, but we went out to eat. We knew that that was something that was a big spend for our parents, but they were committed to it. We did it consistently.”
The people who tell me these kinds of stories who’ve grown up in those kinds of environments where there was that thing that they got, to your point, it wasn’t all about taking. There was something that they did give themselves in the scheme of their financial situation. It helps make it more tolerable and sustainable rather than being the pure guilt, shame, and masochism that a lot of people feel like they have to go through, which is why they get into complete denial. Somebody may be on this call who got a puppy instead of facing her 401(k) rollover.
I don’t know who you’re talking about, but it might be me. This is a true story. I had to rollover a 401(k) from a job I’d had. I’m doing very well financially by this point. I know how to do money. I know I’m not afraid of it. I have moved from saying, “I can be good at money,” to, “I am good at money,” but my old pal, money avoidance, shows up years into my success.
I have to roll this 401(k) over, but the paperwork was complicated, and I didn’t know what to do. I go to Google, and Google gives me all these adorable pictures of puppies. No kidding, I ended up buying a dog. This is how I have my delightful dog. I shook it off a few weeks after getting through the potty-training phase with my dog. I did manage to get my rollover done. It wasn’t that hard. I had to call people and fill out some forms.
That money avoidance comes from, for me and for a lot of people, shame. It’s like, “I don’t know what to do. I should know what to do.” I feel ashamed, and I look away. That’s a super normal, biological human thing. We don’t want to do things that make us uncomfortable. Way back, that was probably danger. That was a good safety response. If somebody feels uncomfortable or scary, we peace out. We avoid it.
One of the four things I often talk about with folks is figuring out how to identify shame and how to transmute it into something different and, hopefully, reduce it. Shame mostly creates avoidance, or sometimes even doubling down on bad money behaviors. We’re like, “Why bother? I shouldn’t even bother trying because I’m so bad.”
Separating Shame From Guilt
The difference between shame and guilt is important. Guilt says, “I did a wrong thing. I spent past my monthly budget for eating out.” That’s guilt. Shame is, “I am a wrong thing. I am bad at money.” The reason that this is important is that guilt, “I did something wrong,” is fixable. Shame, “I am something wrong,” is not fixable. That’s why it’s so limiting. I don’t like shame because I don’t like shame, but I also don’t like shame because it is the most limiting factor for most people in changing their money lives.
In the book, I spend a little bit of time at the beginning talking about how to stitch up someone’s mental game, like, “Get your mental game right. Get your mind right.” Part of that is being able to identify when you are taking yourself down a shame path and getting yourself out of that place. We all know that that’s where money mistakes happen more frequently.
You’re hitting on why Carol Dweck’s work on growth mindset is so important. That, in part, is talking about the difference between, “I made a mistake,” versus,” I am the mistake.” We also know that shame is prevalent because otherwise, Brené Brown wouldn’t be as monumentally famous as she is. She is the woman who made it okay for grown men to cry about their shame. There’s a lot of shame out there, and there is a lot of avoidance. You also talk about the fear of the thing is worse than the thing.
That’s a super ripoff from Buddhists. If you know, you know. The fear of the thing is worse than the thing. There are a couple of different things about shame and fear. One is creating the conditions to feel those things less. That makes it easier to succeed. If I feel guilty versus ashamed, that’s better. I have a whole bunch of practices in the book about how to deal with yourself when you do feel shame in the moment. You’re trying to create the conditions where you feel less shame. There’s what you do when you feel that fear, anxiety, or shame, like how to do it.
I’m going to say it out loud. There is an element of putting one foot in front of the other and doing something anyway. In those moments, what I would tell myself is, “I know that the fear of this is worse than doing it. I know that.” It turns out to be true. One of the things I often encourage people to do is whatever envelope you’ve been avoiding opening or whatever account you’ve been avoiding logging into, do it. Take five minutes. Set a timer. Go get the envelope. Go get that website up. Log in. You don’t have to do anything with it. Look at it, breathe, and then go do something else.
You’ll find out that you survived. Lions did not come out of the walls to eat you. You’re okay. Building our tolerance for discomfort, which is not danger, is another core part of money. It’s two different things for a lot of people. It’s figuring out what the money is for, like what the things you want are or what the life you might want to look like is, and then also figuring out how to give yourself enough practice at building the muscles to take a look at what is, so you can figure out how to get more to what you want it to be.
We were talking a little bit about this before we started recording. This is a career-focused show. You have your focus on financials. I was saying to you that they are very related. Listening to the way you’re describing this, so many of these same behavioral things apply in the way that people think about their money and the way they think about their careers.
They avoid making the big decisions. They feel a lot of shame about things. They don’t have that growth mentality. Therefore, they lose out on opportunities because they’re not willing to consider them. In the same way, a lot of these same behaviors lead people to do less optimal things with their financial situations as well. If you can get one right, you could probably get the other one right with half the effort. That’s the overlap between our two topics.
Connecting Finances To Career Growth
That’s such a good way to think about it. One of the things I spend a lot of time talking to folks about is how to ask for a raise. For a lot of people, the biggest way they can change their money life is to make more money, especially when you’re earlier in your career. The culture of learning how and when to ask for a raise is the same mental muscle as it is to call your credit card company and ask for a lower interest rate, or call your cell phone company and ask for a better cell phone plan. It’s the same stuff. It’s the same mechanics. It’s the same prep. In my book, I have a whole section on, “Here’s how to ask for a raise at work.”
Money is a Rorschach test for what matters to us in our lives. How we choose that is one of the things we have control over. For example, a lot of people experience their budget as limiting and painful. Nobody likes to look at it because it’s evidence of how you didn’t make good choices. All that’s understandable. I am not saying to imagine a better thing, and then magically, you have more money and things get better. I get aggravated when people are like, “You can candle and crystal your way to a better money situation.”
To stop buying lattes. I know you hate that.
You’re trying to get me all riled up. That latte celibacy will not save us. It makes people poorer because then they hate their budget. It’s exactly what you said. I think of a budget. This was a mental shift for me, too. Not that I didn’t experience all these things before. I did, which is part of why I wanted to write the book. I’m not naturally gifted at money.
My husband has one of those calculator brains. He understands crypto and Polymarket. I could, but I choose not to. I think those are pretty unhealthy for wealth-building in our society. He can navigate all that stuff. I’m not like that. I’m a simple woman of simple pleasures. If I can figure out money, anybody can figure out money. I don’t want to take us on a road of banging on cryptocurrency, Polymarket, and policy embedding, so I’m curious if you have opinions on any of that that you want to talk about.
A lot of these things tap into the same things that all the lotteries tap into. It’s this idea that there’s a magic fix for this. My wife used to work with somebody. Every Wednesday night and Friday night when he would leave the office, he would say, “Have a nice life.” He was trying to tell you he was going to win the lottery the next time. It did not happen, for the record.
There are so many things that people believe and do that are ultimately unhealthy. If you step back and think about it, when you ask them to stop doing some of those things, you’re not asking them to give up eating. You’re asking them to give up having an entire bag of potato chips while sitting in front of the TV at 10:00 at night.
There are things in the extreme that ultimately hit you in terms of your health, your money, your career, or whatever that you can get rid of that aren’t going to kill you by doing it. It doesn’t mean you have to systematically dismantle your entire life. “I can get the most benefit that I want to get out of it for way less effort,” is the way to be thinking about a lot of this stuff because behaviorally, you’re more likely to sustain that.
That’s a great way to think about it. My mental shift around my budget was, “I feel so bad every time I look at it. I don’t have enough money. I see how I blew past these budget lines. I feel bad.” What I chose to do with my budget was to say, “This is how I’m making choices with my money.” I have one hour a month where I look at my money, and I choose. It’s like, “I get to decide. A budget is how I decide what I want to do with my money.”
It became for me a practice of feeling like I had more agency and control over what was happening with my money, which is often what I hear from people. They don’t use all those words all the time, but people say, “I feel out of control. I don’t know what to do.” People feel out of control because A) It’s hard to succeed in this society, and B) We don’t all have access to simple, easy information that helps us choose. Also, the feeling of looking at money makes us feel bad.
Once you get your mind right, once you have a budget that lets you make the choices that you want to make, and you have time that you dedicate so that you are thinking about money, what became true for me was that it helped me understand how to look at things like my 401(k) versus meme stock, bets, or prediction market betting. It made me understand the math around that stuff.
The math is clear that it doesn’t make everyday people richer. The lifetime analysis of this is so mathematically not arguable that you will make the most money by putting your money into a tax-advantaged retirement account and putting it into a target date fund that has a standard mix of things and is largely invested in index funds. It’s so clear about this.
The reason that people get seduced into what feel like easier, bigger money opportunities is that the feeling that we can succeed the normal way feels much harder for people. They’re not crazy. The cost of education, healthcare, housing, and childcare has gone up so much farther than wages. The median first-time homeowner age has passed 40.
The idea used to be that you go to college and get a good job. It wasn’t always this way for everybody, but the theory was college gets you a good job. That job gets you a good salary. That salary gets you a house and maybe a family. Two incomes are required, but it felt more doable. As time has gone on, it’s harder to navigate. It’s harder to afford all of that. What we’re seeing is people turn to places that aren’t going to work for them in the hopes that this can solve what feels like an unsolvable problem.
I often say to folks, “I’m not asking you to give something up. I’m asking you to replace it with a different behavior, which is checking in with your money and making choices that are more likely to make you more money. We could talk about how you also increase your income.” For most people, that’s the limiting factor. I have empathy for the folks who are like, “I got to try to do anything. I got to go try to get that lottery ticket,” but I feel compelled to say, “There’s a better way to build financial security for yourself.
Talk a little bit about your organization.
I run a nonprofit called WorkMoney. We are building an America where everybody can afford to live a good life. We help people raise their incomes. We help folks lower their costs. We have coupons and discounts. We do a lot of work with folks on how to understand what you can do individually with your money. I have a very clear point of view on this. The math and science are pretty clear on this.
You must play the individual hand of cards you are dealt. There’s no getting out of your responsibility. It is also true that some of us have worse cards than others. That doesn’t, however, get you out of having to play those cards. Even if your cards are worse, you still have to do everything you can, put one foot in front of the other, learn to get back up when you fall, and do what you can to improve your circumstances.
Leveraging Collective Consumer Power
We have a lot of power as a group. We can get together as consumers and bargain for cheaper stuff and things. Who among us is not having a love affair with Costco? That’s a great example of group buying. Imagine if we could apply that kind of thinking to health insurance and cell phone plans. Imagine 50 million people in an organization using their strength in numbers to bargain and put ourselves in the market as players in the market. This is my ideal for WorkMoney. We’re about nine million. We’re trying to get much bigger.
We also have a lot of power as constituents. The economy is not a mysterious weather event that we must endure. It is a set of choices made by people whose companies we buy things from, invest in, or work for. It’s also made by people we elect and policymakers that they appoint. We do have levers. We need successful companies. That’s how we have jobs. That’s how our economy runs.
I’m a very pro-successful-company person. I’m pro people getting wealthy. I think all that’s great for the economy. It needs to be happening in a way that isn’t at the expense of the majority of humans who live in this country. We’ve done this before. We’ve seen versions of America where more people could succeed, and people had access to education. We know how to do this. This is not new news.
My vision for WorkMoney is an organization that helps people use that strength in numbers to lower prices through bargaining in the market and making sure that politicians and business leaders of any party, any stripe, and any size understand what we expect from them. I love this idea. Many of us can build the businesses that we want to exist in this world. I love the idea of WorkMoney seeing and backing entrepreneurs who want to bring good stuff into people’s lives, especially financial products and services.
WorkMoney has a startup called MoneyFinder, where we’re negotiating to lower people’s cable, cell phone, and internet bills. I love this idea because it’s backed by a nonprofit. You can trust it. We’re not trying to extract. It’s also going to help people with their money. Finally, I’ll say that some of what you do is part of the answer. We’re also pretty powerful as an audience and as creators. We can make the content that we want to see. WorkMoney is a big nonprofit. My idea is that we use the strength of a lot of people to make the economy that we want to live in.
Thank you for doing what you do with your nine million members. Hopefully, that number will continue to grow. I hope the book has had success so far in its launch. I wish you well.
Thank you. I’m supposed to brag. The Joy of Money, which is the book I wrote, made the USA Today bestseller list.
Thank you. I’m so excited. I love what you’re doing, too. Navigating careers is such an important part of people building financial security. I love recommending your show to other people. Thanks a lot. I appreciate your time.
I appreciate that. It’s great having you on the show. It’s good to get to know you.
Thanks a lot. I appreciate you. Take good care.
You too.
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That was a terrific conversation with Carrie Joy. Let’s talk about some of the key takeaways. First, being good with money may come more easily to some people than to others, but Carrie Joy’s core argument is that financial security and good money habits are learnable. A related point, one of the most important ideas in the conversation and her book, is that money isn’t math, but it’s also emotional.
You have to understand both parts of that equation to understand how to manage your own money and how to deal with it in the emotional context that works for you. Until we understand those stories and feelings that are driving our behavior, it’s hard to have a healthy relationship with money or to make lasting financial change.
Second, avoiding money problems almost always makes them worse. Carrie talked a lot about shame, avoidance, and what she calls the fear of the thing. Whether it’s debt, checking account balances, savings levels, or even asking for a raise, the anxiety around confronting these topics is often more damaging than the actual problem itself. That’s one of the most hopeful parts of her message. Progress doesn’t require perfection. It requires small, consistent actions that compound over time. She talked an awful lot about compounding, not just financially, but emotionally and psychologically as well.
Finally, the conversation challenged the idea that personal finance is purely an individual responsibility problem. Although we didn’t talk so much about this in our conversation, Carrie Joy makes the case that two things can be true at the same time. We are responsible for our financial choices, and the modern economy has become genuinely harder for us to navigate. Rising housing costs, healthcare, student debt, job insecurity, and wage stagnation are real forces that are shaping people’s lives.
What makes her perspective different is that she refuses to reduce financial struggle to either personal failure or systemic failure alone. She asks people to build skills, confidence, and agency, while also recognizing the broader economic realities that they’re operating inside. There’s a huge parallel here with the way that I think about career management. We have to have ownership for it. Even if the society around us is doing things that make having a sustainable career tough, we still have to make it work for ourselves. Avoiding that is only going to leave us feeling worse and being worse.
Ultimately, the conversation we had is about something deeper than money. It’s about dignity, stability, and freedom. It’s about the belief that your financial future is not already decided for you. Thanks again to Carrie Joy for joining me. I invite you to subscribe to the show onApple Podcasts,Spotify,YouTube, or wherever you tune in. If you found this discussion enlightening, sign up for my membership community, which is called PathWise, and our newsletter,PathWisdom. Thanks.
Carrie Joy Grimes is the founder and CEO of WorkMoney, a national nonprofit building an America where hardworking people can afford a good life. A former union organizer who helped win higher wages and better benefits for millions, Carrie Joy now channels that same people-first energy into practical money advice and strategies to raise incomes and trim costs for millions of everyday Americans. She lives in the Pacific Northwest.
The Hidden Risk Of A Great Career (And A Different Path To Financial Freedom), With Jon Ostenson
August 3, 2026
What if the biggest financial risk in your life isn’t the stock market—but your paycheck?
Most professionals spend years building successful careers, yet their entire financial future depends on a single employer. In today’s world of layoffs, AI disruption, and economic uncertainty, that’s becoming an increasingly fragile strategy.
In this episode, JR Lowry sits down with Jon Ostenson, founder of FranBridge Consulting and author of Non-Food Franchising, to explore an alternative that more professionals are beginning to consider: business ownership through franchising.
Forget fast food. Jon explains why many of today’s fastest-growing franchise opportunities are in service businesses—from home services and senior care to B2B consulting—and why they’re attracting professionals looking for additional income, long-term wealth, and greater control over their future.
Together they discuss:
Why relying on one paycheck may be riskier than owning a business
The biggest myths about franchising—and what it’s really like
How professionals can own businesses while keeping their day jobs
The difference between entrepreneurship and buying into a proven system
What makes some businesses more recession-resistant than others
How business ownership fits into a broader wealth-building strategy
Whether you’re dreaming of leaving corporate life, looking for a second source of income, or simply thinking more strategically about your financial future, this conversation will challenge how you think about work, risk, and ownership.
Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/jon-ostenson/.
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Watch the episode here
Listen to the podcast here
The Hidden Risk Of A Great Career (And A Different Path To Financial Freedom), With Jon Ostenson
What if the biggest financial risk in your life is your job itself? Now, you may feel like you’ve done everything right. You’ve built the resume and climbed the ladder and become valuable. Maybe even indispensable. In doing all of that, your entire financial life has become linked to a single source of income, which is your job. Many times, in such circumstances, this narrow form of success can start to feel like a prison. It’s risky with everything going on in the world. We’re living in a very uncertain environment with layoffs, AI-driven disruption and geopolitical change.
A growing number of people that I talk to are starting to ask themselves, “How do I avoid having to be on the treadmill forever?” Our guestJon Ostenson is a firm believer in a different path. One that sits somewhere between corporate life and high-risk startup culture. Jon is the Founder ofFranBridge Consulting. It’s a top franchise consulting firm that helps their clients to acquire and scale cash flowing service businesses often while they’re still working full-time.
Before you tune out because you heard the word franchise. This conversation is not about opening a fast-food restaurant. It’s about ownership, predictable cash flow, time, freedom and lifestyle design. It’s why more and more working professionals are rethinking what success looks like and considering franchise models.
In our conversation, we’re going to talk about the hidden fragility of career based-wealth, why service businesses are attracting smart industrials, the biggest myths that people have about entrepreneurship in franchising and how to think differently about risk, freedom, and the path ahead. I’m J.R. Lowry, this is Career Session.
I’m looking forward to talking to you about the work you’re doing. I know you spent a long time in corporate leadership and then you moved into entrepreneurship and investing. Essentially, you’ve gone from, as you’ve described, an earning income to building ownership. What changed and drove your distinction between those two?
Shifting From Earned Income To Asset Ownership
I could have done the corporate world forever but you only live once. I had desired it to build my own thing. To seek that freedom that everyone talks about. Most people have that in them and almost step out and some don’t. It’s through circumstances that I was in my mid-30s and started doing some networking. I’m trying to figure out if I were to leave a large public company, what would be a good private company where I can step into and sidestep entrepreneurship? That was my thinking and circumstances worked out.
I had the opportunity to come in and run a large franchise system called Shelf Genie. We’re supporting franchisees all across North America. A lot of diverse backgrounds coming together under a shared system of support. We’re allowing them to fulfill their dreams and become business owners, but with some training wheels. I fell in love with the franchise model through that experience and have vested a franchise myself since then.
A lot of people think about franchising and they think about restaurants, because that’s probably what we all know best. There are many different franchise models out there. Some of them I would describe as being less familiar to people but still potentially lucrative.
Exploring Beyond Traditional Food Franchises
We’ve got nothing against the food guys. We certainly need all of them, but my humble belief is they’re easy ways to make money and they require fewer employees, less operating hours, higher margins, oftentimes, and less capex investments. It’s fun for us to take clients through the process of identifying the top opportunities that are looking to expand in their area. Probably 90% of the time clients get into businesses and industries that were never even on their radar.
There’s so many different niches within home services, properties services, and different B2B services. Businesses that cater to the senior population or to kids or to pets or to health and wellness. If I were to break those down even further, it’s things you probably don’t have on your bingo card when you hear the word franchise.
How many of your clients that you work with go into these franchise opportunities, running them actively themselves? How many of them go into them or what percentage go into them looking to hire a general manager, and run it more as an owner and not necessarily as the operator?
Evaluating Semi-Absentee Business Models
I would say roughly half and half. There’s an owner operator model then there’s what franchise is oftentimes referred to as semi-passive or semi absentee or executive model. You’ll hear those terms. The idea is that you put a manager in place. I prefer the term semi involved. That’s better. You’re still going to be involved. The amount of involvement that you put in is dictated by who you put in that seat. If you’ve got a great operator that’s incentivized, that’s going to run it like it’s their own, you’ve got a strong franchisor supporting them. They can carry a lot of daily support. Why don’t they take some of that burden off you? It is a very common approach in franchising.
It’s interesting. There was an article in the Wall Street Journal about this idea of passive income, which seems to be very much in vogue. I feel like it’s probably, like many trends, getting past its prime in the sense that people think that they can make anything passive income, including having a full-time job. That they can do that in just a few hours a week and still get paid for it. Franchising is work. I’m sure you want to make the point that it’s semi involved. You can’t set it and forget it. You’ve still got to be engaged in this.
I read that same article. We hear these common themes all the time about creating passive income, trying to free up flexible time for the family, and live life on your terms. It’s what everyone’s marching towards. I do remind people that if business ownership is easy, even franchise ownership, everybody would be doing it. It does take work, but there’s a reason why you can make outsize returns. There’s a reason why the government incentivizes through the tax code business ownership. Whether you’d be creating jobs or simulating the economy in different ways.
There are a lot of benefits to it, but it does take work. A lot of our clients will start out with one franchise and then expand to other locations. They’ll buy other franchisees in the system. They’ll come back and buy additional franchise brands. In those cases, you’re not running each of those right from a daily standpoint, but you got in, got your hands dirty and then rolled and pushed the reins to one else.
It feels like we’re in this environment now, where a lot of people who are in their 30s and 40s, feel successful on paper but they still are heavily dependent on their job. You’ve got affordability issues, whether it’s food or housing or daycare or whatever that are creeping in. Do you think that realization is hitting people more than in the past?
I would say so. We’re certainly seeing more interest than we’ve ever seen in business ownership. For a variety of reasons, certainly AI is playing into that. All these headlines that we read about, I see it playing in real time all around the country. A lot of people are being asked to do more for less or saying, “I’m capped as to what I can make and yet I’m putting in a ton of effort building someone else’s empire.” People talk about business ownership as being risky.
Comparing Franchising With Business Acquisition
I would argue that working for an employer at their whim is risky. One way that people will de-risk the idea is to acquire an existing business. ETA is a big thing to date, or Entrepreneurship Through Acquisition. I wrote an article on this where I talked about franchising versus ETA. If you find an existing business, that can be a great proposition.
Most of our clients are taking them 3 or 4 years and they’re like, “We keep looking,” and then they’ll come to us and say, “Maybe franchising makes sense. It allows us to get in the game.” We could still acquire existing business down the road. Once you’re in a franchise system, you’re also going to get first line of sight into any other franchisees in that system they’re selling. A lot of our clients will get into a system and over time expand through what I call it Internal M&A, if you will.
Is the buy-in typically for a franchise model lower than an ETA model that you were just describing?
In most cases, it would be because if it’s an existing business, you’re paying a premium for that. You’re making the assumption that everything is going to continue as it has been, as it is on paper, but we all know whenever you have a change in ownership. There’s going to be a slight change in culture. You may lose key employees or key clients. I make the argument for my standpoint that franchising allows you to get in the game.
Non-Food Franchising: Leveraging SBA loans and 401k rollovers allows investors to acquire cash-flowing assets with minimal upfront capital.
It allows you to have a proven business model, but you’re able to put your thumbprint on that organization, that team and culture from day one. What’s interesting is when you look to sell that business down the road. There’s been research done that showed the franchise is traded at a higher multiple on average than non-franchise in light kind industries. There is value in that resale buyer’s perspective on the franchising front.
Do you see most of the people who are getting in that you work with? Are they buying an existing franchise or are they starting a fresh one that’s expanding into their area?
Probably 90% to 95% of the time it would be a new area. It’s not that there’s a lack of interest in resells. It’s just that, again, a good opportunity in the franchise resale game. Go to other franchisees in the system, they never hit the open market. That is a dynamic we see oftentimes.
Do people do this on top of their full-time job or do they fully switch out from what you’re seeing?
About half and half. About half would make the jump. Maybe they have a spouse that’s working. They’re saying, “We’re going to be the ones to get in.” Sometimes, they’re spouse is at home. About half are going with that owner operator usually with the idea of replacing themselves eventually in the business. The other half say, “We want to keep our day job at least for the short term and we’ll put a manager in place to run that business. Again, it comes down to having a good jockey. You have a great horse stuffed out by a good jockey.
If you go with that ladder model, Jon. What’s your view on what success requires? What do you need to do as a semi involved owner to make sure that it’s going to go well?
It’s finding the right franchise system. This is essentially a partnership or a marriage. Finding the one that will support that manager in a significant way so you’re not the go-to for all their daily questions, but then finding the right candidate. It’s setting them up for success, whether that be through the incentive program. In some cases, clients of ours will give equity. They’ll loop them up to the cap table to incentivize.
In other cases, they’ll give quarterly bonuses or what have you that act as equity like a profit-sharing type program. It’s been my experience. If you have the right individual in that seed and they’re incentivized, then it can be a great model because you can be incredibly hand-off. If you don’t own the right individual, then you’ll lean in until you replace them and find the right person.
What are some of the particular franchise opportunities? What are the categories that are most exciting for you?
There are so many unique models. I’ll just mention a couple of franchises that were made. There are only one or two players in that space from a national standpoint like teen driving school. It’s required in 36 states, and there’s only one franchise in that space. There is a lot of interest in property services. We’re seeing a lot of smart money flowing there. Some of the businesses I own, I’ve got one that provides asphalt paving and line striping, so parking lots. I got another one that provides temporary containment walls around renovation projects.
I’ve done a couple pool cleaning deals in the past couple months. Cabinetry and flooring. Each one is unique too as far as how they approach the competition. A lot of times, they’re more advanced from a technology standpoint. They’re going after these highly fragmented, unsophisticated competitive industries, so you’re able to stand out. We’re seeing a lot of interest in the senior space. We found a number of clients getting into in-home senior care. As well as businesses that may serve as a guide and they become like the broker for different senior facilities.
We have some clients that have gone into great ones that provide wheelchair ramps, stair lifts and mobility solutions in the home, allowing people to age in place. At the end of the day, they’re B2B services ones, like cost mitigation consulting or freight brokerage or insurance adjusting. We’ve had a lot of physicians and doctors get into ones like restoration. Things that they weren’t trained for but they have some intellectual curiosity and they see the need there in their market.
It’s just interesting watching all of these things play out. It continues to go from having very localized markets, mom-and-pop kind of model to more nationalized. People doing roll-ups or trying to nationalize different business models that before were very much local businesses.
At the end of the day, they’re still local owners. They are local businesses, but they have that broader effect. I think another one. Most founders out of Boise, Idaho have a truck that carries about 200 gallons of diesel and will go around and fill up vehicles in fleets and construction sites and stuff. Those niches that you don’t think about but they said, “This is applicable all across the country. Let’s franchise it as a way to scale.” They’re going to be able to grow more significantly and get better pricing on fuel. They’re going to have locations all around the country with people that are highly incentivized because they’re business owners. Not just employees.
Talk a little bit about the process in terms of how they come to you and how you work with them and get them up to speed on the opportunities that might be available to them.
I would think about a real estate model if you were going to buy a home and work with the real estate agent. That’s essentially the role that I play. My clients never pay me in nickel. Instead, I get a referral fee from the brand on the back and when a placement happens. None of that’s passed on. It’s a nice clean model just like in real estate. We work with over 600 different franchises. They’re looking to expand part of the largest network in the country.
The process would work is, let’s not sit on the sidelines and do personality tests and hypothesize around businesses. Let’s get in the game. Let’s look at real opportunities in your market. We’d have an introductory call. Shortly after that, I would come back to you and say, “Based on the feedback I got from the franchise owners here, the ones that are open are looking to expand. We look at maybe a dozen or so companies out of the gate. Give you some good exposure to what’s out there. You’d pick a couple to have a conversation with, we can always iterate from down the road, but that gets you in the game.”
That’s where the magic starts happening, and you start comparing and contrasting. I hold your hand through that discovery process. It takes about two months on average, but you’re getting a chance to talk to all types of people there at the franchisor’s company or talking to other franchisees in their system and about their experience and asking questions. The goal is to get you as much information as possible. I’m there to be a sounding board but also provide funding resources or if you want a franchise attorney review the agreement. We’ve got all these types of partners to support as well.
I know your base in the Atlanta area. Do you work with people all over the country?
All over the US and Canada. I’ve done placements in just about every state that has at least 500,000 population.
How do you, being based where you are, get a sense of the market and help your clients evaluate whether that market is a good fit for that franchise?
There are a little bit of art and a little bit of science to it. We started a 30,000-foot level where we’re looking at businesses that have done well and comparable markets and introducing those. Sometimes, clients will say, “I know this one saturated in my area or there’s a huge need.” I’m not privy to that. There’s a little bit on their end, but once they start talking with the franchise or the franchisor has the information at the ZIP code level from a demographic standpoint, they could say, “Here’s how we would define that territory. We include these zip codes. Not those.”
From there, I encourage clients. Once you get pretty serious with one, do some secret shopping. Go visit them. Go visit the locations or have them come in and give you quotes and find out who you’re up against. We start at a high level and then boil it down. Many of these businesses are pretty geography agnostic to some degree. There’s going to be some that just don’t make sense on a certain market, but they think of like pool cleaning as an example. The one that we like started in Canada. Now, it has a presence across the US. Sometimes they’ll surprise you.
I’m sure people come to you with all sorts of misconceptions about franchising. What are some of the most common ones that you hear from people that you have to dispel?
Non-Food Franchising: Franchising provides proven systems and corporate support, making business ownership far more accessible than starting from scratch.
The one we hit on already around the franchise will run itself. If it ran itself, then you wouldn’t be needed. Franchising gets grouped together like so many other industries. We talk about franchising. At the end of the day, it’s a couple hundred different business models across a couple thousand companies. It is hard to generalize too much but I would say that the role of the owner, as we talked about, it’s not going to run itself.
Every now and then, you’ll have a franchise that does not provide great support and it will catch some headlines. You see this sometimes in the food space. I hear that but again, every industry has got good players and ones that aren’t as good. Franchising is no different. Certainly, that’s where we come in to help. Oftentimes also people overlook some of the benefits associated with franchising. You’re stepping in not just getting support from the franchisor but you’re in business for yourself but not by yourself to be cliché. You’ve got a mastermind or other franchisees and you’re learning from each other. Making sure you don’t make the same mistakes that someone else made and exchanging best practices.
I know you’ve used the phrases recession, resist and cash flows. Some of these businesses you see as being relatively immune or maybe even beneficial in a recession environment. What makes certain businesses more durable or attractive during periods of economic uncertainty?
I’d say less discretionary spend reliant type businesses. Think about what people are always going to spend on. They’ll spend on the things they care about like their kids, their aging parents, their pets, their homes to some degree, and their health. There are some more fashion forward franchises out there like in the health and wellness space. Whether it be peptide, injections, or some of the recovery modalities.
In some cases, people may cut back on those things during a recession, but they’re always going to spend on the cure for their elderly parents. They’re always going to need day care for their kids. We think about what they will continue spending on. One thing I’ve noticed is, when it comes to business ownership, I joke that non-sexy is the new sexy. People like those understandable cash flowing businesses. The surf pros of the world. They’re not going to go out of style.
I don’t know ifCodie Sanchez. I see her pop up in my LinkedIn feed all the time. That is like her mantra, “There’s a lot of money to me made in these businesses that are seemingly pretty boring.”
She’s got a great following. She does a great job with her content. Again, a lot of our clients have been following her but they have found that business and that’s to say, “We like the idea of franchising. Get us in the game.”
You work with a lot of different franchises. I think you mentioned 600. How should someone look at a franchise and evaluate whether they’re good and healthy? Versus, good at marketing or have an economic model that benefits the franchisor and not the franchisees.
It’s certainly tough if you Google around online because even if you come across the top 100 franchise list. Most of the companies have paid to be on that list. It’s a PR move. That’s where we come in. We have those relationships and see behind the curtains. Some of the things that we think about, certainly the track record would be the biggest one. The fact is, if a franchise has 50 locations or 100 locations, they’re going to be sold out in a lot of the areas that you would want to be in.
Oftentimes, we are working with ones that are more emerging that are newer. The things we look for are strong financial model, competitive advantages, and unique about the business. Their existing franchisees have to be happy with their experience then we put a lot of weight in the leadership team. We want to see not only a good blend of industry experience, but also franchise experience represented on that team. People that have supported successful franchisees and other systems in their background. As I said before, a little bit of science and a little bit of art to it because like in the industry, not everyone’s created equal.
Let’s come back to some of the trends that are driving this, particularly the idea for optionality and time freedom. What do you hear from people who have stepped into this that you’ve worked with that may be surprised that either positively or negatively about what that transition is like for them?
Generally, we’ve heard, “It’s more work than we thought.” I was catching up with a client that it bought years ago and he relocated to where the franchise was available down in Fairhope, Alabama. He’s done incredibly well. He’s dropping well over $400,000 a year to the bottom line. I’m very happy. He’s now ready for his next franchise. I’d say walking with him through that journey, early on, it was a new franchise. They were selling quickly. They had a lot of things going for them but, in some ways, there’s a little bit of guinea pig with the early franchise.
I always want clients to go in eyes wide open, to that being the case. In some cases, it’s a little bit of a blend. You want to get in early to get the territory, but you’re also stepping into something that’s a little bit newer and they’re still figuring things out. One thing we haven’t hit on that I think would be helpful is the financials around it. People oftentimes say, “How much is this going to cost right? McDonald’s are incredibly expensive and Chick-fil-A has this unique model that’s very different from an investment standpoint.”
In the non-food space to level set. If you look at your franchise fee, your startup cost and several months are working capital since you’re all investment range. If it’s a customer facing retail, physical location type establishment, you’re probably all in $300,000 to $600,000 in most cases. Now, add some clients by 10 trampoline parks at $3 million each, but most people aren’t doing that. Let’s just call $500,000 or $600,000 on the high end.
Financing Franchises Through Strategic Capital
On the service-based business, which is about what 2/3 of our clients are getting into. Think in-home senior care or somebody’s home services or consulting services. Your all-in investment tends to be more like $100,000 to $250,000, kind of in that range. A lot of our clients may be sitting on cash where they could fund it, but they like that idea of leveraging. An SBA loan tend to be very common. Banks prefer lending to franchises. Probably more than half of our clients will use SBA loans, where they put in $50,000, then leverage the rest.
Another strategy a lot of people employ is to use what’s called a Rob’s program. That’s a retirement rollover. You can take a 401(k) or IRA. It’s got to be from a previous employer. I can’t be your current one, then you can purchase the business that way with the retirement and then pay yourself a salary. There’s a lot of ways to make it happen, but it is eye opening. People sometimes say, “This is more realistic than I thought it would be.”
What does the payback period typically look like if I’m putting that $300,000 or $400,000 or $500,000, or $600,000 in to pay the franchising fee and working capital and those kinds of things? How long does it take me to earn that back?
The biggest variable there oftentimes is whether you’re running the business yourself or you’re paying someone else too because that will be enough to cover. Let’s just say that you’re running the business yourself. It typically will be a little bit longer if it’s a retail business because you’ve just got the lease payment that you have to cover as well. In a service-based business, they are cash flowing from day one.
Maybe the initial marking drove and you have low enough overhead. I’d say most of the time, you’re probably around six months mark where you have a positive monthly penile. That’s how about it. I always want our clients go conservative, so let’s call it nine months and round off. If it’s a retail location of maybe 6 to 12-month window, more than likely. If you’re paying someone to run the business, then maybe a full year before you’re cash flowing.
In terms of, “I’ve turned profitable 6 or 9 months, then I’m starting to generate a profit on an operating basis, but I’ve got this up-front piece. How long does it take to earn that back, pay back those SBA Loans or whatever you’ve chosen to do to finance the business?
If you’re in that $400,000 to 600,000 retail range, it’s going to take potentially 2 or 3 years in a lot of cases. It may be even 3 to 4 years if you’re paying a manager. You are also building an asset that you’re going to sell. It’s not just that you’re throwing money in. In what you’re putting in, you should be able to get back in theory and regain tax benefits along the way. If it’s more of a service space business, that payback period could be 12 to 18 months in a lot of cases.
If you’re all investments of $150,000 and you’re at a run rate now and going into that second year, we were dropping a little over that to the bottom line. Again, I’d say where we see a breakpoint of the times is around that twelve-month mark where it’s not that you made X amount in the first year but you’re now at a run rate of X amount going forward. We’ve got a number of clients that have done a million dollars in revenue in the first year. Most of the time, it’s probably between months 12 and 24 of a business capable of hitting a million that you would get to that run rate during that time period.
I would assume that you work through your clients with the financial modeling and the different scenarios in terms of how things could play out as well.
From a fairly high level. I don’t get super granular with them. That’s a little bit more on the franchisor side to make earnings claims around, but they’ll have a performa template and expectations. They’ll take you through what’s called the unit economics call, where they’ll dig into the details. Another data point that you get is talking to other franchisees and they can open up their books as much as they’re willing to. Everyone’s a little different, but they can give some good feedback on how quickly they turned a profit and it’s worth it.
Non-Food Franchising: Think franchising means fast food? B2B and home services offer higher margins and greater operational flexibility.
You mentioned a minute ago that this is an asset. I know you view this in some ways is part of a portfolio diversification strategy for somebody thinking about saving for retirement, building wealth just like you’re investing in stocks and bonds and maybe you have a house. Maybe you have rental houses. This is another asset class to consider. Talk a little bit about why you feel like this is an important part of that equation.
I’m a big alternative investor. I’d say when I look at my investments, probably 25% is in the public markets, but 75% would be in things everything from private credit, private equity to real estate, syndications and funds. For me, it’s all of the above approach. I like to roll real estate plays in the portfolio. Be able to take the depreciation and offset some passive gains. I like business ownership because you can offset a lot of active gains, active income, especially early on.
There’s so many things you can do with business ownership. It’s a piece of portfolio outside of it just not being correlated to the public markets in a significant way. You can pay your kids through the business and then they have earned income and you set up Roth IRAs for them. It gives them a leg up. I’m sure you can take a larger define benefit plan if you want to bulk up your retirement. Certainly, write off home office expenses or vehicle expenses or cell phones, or internet. Again, when you start thinking about the possibilities, it’s a third dimension to cash flow building an asset, but all the tax benefits. That’s how I think about it. Again, it takes a little more effort than a passive investment, but there’s also benefits to that.
Thank you about that risk reward balance. You need to do that with any asset class. It makes investing in a certificate of deposit. It’s very different from investing in the equity markets, different from investing in real estate and different from investing in this. How do you help educate your clients about the risk differences that come from being in one of those more conservative asset classes? Also from being an employee to being an owner.
There’s operator risk. At the end of the day, business ownership is not for everyone. I do believe there are people on the sidelines that should be in business ownership, but there are some of them that shouldn’t. I do believe franchising is a better path for most people because you get that support system. You’re stepping into something that’s already an established product market fit. Again, you get that support not only from the franchisor but other franchisees and a lot of training and support along the way. We talked about it, but there’s certainly to anything.
If it wasn’t worth doing, there wouldn’t be a risk to it. I would like to share an example. I play nine different clients with a franchise a couple years going on a property services arena. We had some clients do a million dollars in their very first year with that one. A lot of clients did very well. One client went out of business up in New Jersey and her was a marketing guy. I thought he was pretty smart. I reached out to the franchisor who I knew well. I said, “Help me understand what happened here. Everyone else is thriving.” He said, “Jon, we’ve done everything we can to support him but he came in. Candidly, he thought he was the smartest guy in the room no matter what room he was in and thought he had a better path to follow and didn’t follow the system.”
Following Proven Systems for Maximum Success
They said, “We coached him. We did everything we could.” Thinking back to when I was a franchisor Shelf Genie and I had 100 franchisees I was supporting across North America. Our best performers were the ones that followed the system the closest. That sounds so cliché, but it was true. Those were the ones that performed. There’s a reason why you get into a franchise system. Is anything entirely de-risked? No, but if you’re willing to have that humility to go in and follow the playbook, you increase your chances significantly.
This process can be humbling for a lot of people because in a lot of ways, becoming the owner, you’re going to find things that you thought you were good at as an employee. It’s not relevant anymore. I would imagine coming back to the point you made a minute ago about the people who are following the system. It’s having that level of focus, being able to say, “This is what I need. I need it by this time frame. Here’s what I think good looks like,” which a lot of people dance around because they’re uncomfortable with being that blunt. That directness, I would imagine. That willingness to get into the details has to be pretty important to being successful as a franchise owner.
I couldn’t agree more and people often times ask me, “What makes a good franchisee?” I talked about what we just discussed. That humility to follow the system, but you also have to be hard working and you’ve got to be halfway decent with people. That’s Business Ownership 101. If you check those three boxes, your odds are pretty good.
What are some of the other mistakes that you see people make that you would counsel our readers to try to avoid if they’re interested in this?
In very business, there’s going to be at some point, whether it be 3 months in or 6 months in and maybe be you’re like to your spouse or the kids, “Is this the right decision? Did we make the right move?” There’s going to be a hard time. Working for someone is hard. Business ownership is hard. There’s going to be a point where you probably second-guess yourself. You say, “Do I keep putting money into the marketing or maybe my expectations that I’d be further along profit wise.” You have to push through that.
It’s just so normal. There will be a point, do you find marketing further? Do you invest in that next employee? When you need half an employee, do you invest in a full employee with eyes towards growth ahead? It’s doing that extra little bit of work early on that sets you up for down the road. I’d love to say we have a perfect record. I’m very proud of our record, especially within the industry. There’s a reason why we’ve build the reputation we have, but at the end of the day, it’s following the system, working hard and pushing through those times.
It’s important certainly for people who are considering this to come in with a realistic view of it. To me, it’s a very intriguing opportunity in terms of how you commit to spend your professional life but also potentially how you look at your investment mix in both of those lights. It’s interesting, but you also obviously don’t want people coming in with a false view of what it’s going to be about from a financial perspective or from an operational perspective.
I tell people that all the time because we do get a lot of folks that will reach out and say, “I can pick up pretty early.” This may not be the right fit for you, at least not in the season of life. There’s never a perfect time to step into business ownership. There’s never a perfect time to have a kid or make a big career transition. Is it going to be better tomorrow or is today still the best day to make it happen based on where you want to be one day?
Any last thoughts that you would want to make sure that our readers take away from this conversation? If they’re thinking about this, or maybe they weren’t thinking about it and now they are. That would be helpful to them as closing thoughts.
When you look around, many other people have stepped out and take the plunge if you will. I love getting validation from clients to say, “I wish I’d done it sooner. I’m still so thankful I did it when I did.” I always encourage people to get off the couch. I’m a big believer that activity breeds activity. Getting in the game, there’s entirely no downside to other than spending a little bit of time, a little bit of band width to learn more.
I would love to share a free copy of our book. It’s about 90 pages. It’s been a great resource. We’ve sold thousands of copies. If you want to buy it on Amazon, all the proceeds go to HOPE International. A great nonprofit that we support. We’d love to share a free downloadable copy from our official website at FranBridgeConsulting.com. That could be a good first step. If you’d like to take the next step and jump on a call, I’d be happy to help.
Jon, thanks for this. To me, it’s an area that a lot more people, as they start to think about things like, “How do I get myself off the treadmill of corporate life?” We’ll be thinking about, and whether they choose to do it in the owner or operator construct or as a supplemental thing to what they’re doing in their full-time job or want to dive in fully. It’s important for people to be seeing this as an option for themselves. I know I’m preaching to the choir on that because that’s your life and your business. It’s an important topic and that’s why I wanted to talk. Thank you.
Thanks for having me.
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An interesting conversation with Jon about franchising. Let me try and sum up some of the key points. First is this idea that career success and financial security are not necessarily the same thing. A lot of people spend decades building impressive careers, higher incomes, strong resumes but their entire financial future is still tied to a single employer and a single paycheck. One of the biggest shifts that Jon talked about is moving from purely earned income toward ownership-based income. Assets and cash flow that exists independent of your day job.
Second, entrepreneurship doesn’t necessarily have to mean chaos, massive risk, or working 100-hour weeks. A lot of people still view it through the lens of Silicon Valley startups and people betting everything on an idea that starts with working in their garage. Jon lays out a very different model, acquiring or building service businesses with predictable demand, proven systems and scalable operations. That’s a different conversation than quit your job and hope it works out.
Finally, this conversation was about optionality. Not everybody wants to retire early and not everybody wants to become a full-time entrepreneur. More people do want flexibility. They want more control over their time, their income and their future. Especially in a world where everything seems to be changing so quickly and traditional career paths feel less stable and more risky than they ever have.
Their broader point is this. Ownership changes the way you think. It changes the way you think about risk, income, freedom, and long-term security. Whether or not franchising is right for you, Jon challenges all of us to think more intentionally about what we’re building over the course of our careers. Thank you again to Jon for joining me. I invite you to subscribe to Career Sessions onApple Podcasts andSpotify orYouTube. If you found this discussion enlightening, sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks.
Jon Ostenson is a top franchise broker, author, and international speaker specializing in the area of non-food franchising. Having served as the president of an Inc. 500 franchise system and now as a multi-brand franchisee himself, Jon is uniquely positioned to educate others on franchising and franchise selection.
Jon serves as the CEO of FranBridge Consulting and has helped thousands of entrepreneurs and investors explore business ownership and investment opportunities.
Jon is the author of the book, “Non-Food Franchising” and is a frequent contributor and thought leader for publications on the topic of franchising and franchise investments. Prior to FranBridge, Jon was the President of ShelfGenie, a national franchise system with 200+ locations.
Why Talent Isn’t Enough: The Discipline That Separates Top Performers, with Dre Baldwin
July 27, 2026
Most careers stall because professionals wait for permission, confidence, or the right timing rather than taking action. In this episode, host J.R. Lowry sits down with former professional athlete and entrepreneur Dre Baldwin to dissect why professional discipline outperforms raw motivation every time. Baldwin reveals how he translated lessons from overseas sports courts into scalable business frameworks centered on mindset, strategy, systems, and execution. They explore actionable ways to build true executive presence before you get the promotion, navigate career reinvention, and develop the human judgment skills AI can’t replace.
Why Talent Isn’t Enough: The Discipline That Separates Top Performers, with Dre Baldwin
Stop Waiting for Permission
One thing that I’ve observed over the years and still observed now is that a lot of people spend their careers waiting. Waiting for permission, being noticed, for confidence, for the magical intervention that in most cases never comes. My guest believes that mindset is why so many talented people fail to reach their potential or achieve their dreams.Dre Baldwin went from being an overlooked basketball player with no scholarships and no major opportunities to building a professional sports career.
A global personal brand, a business built around performance, discipline and mental toughness. He was clearly taking initiative. You’ll learn his story as we talked. Millions of people have watched his content online, but what makes his message resonate isn’t just Sports. It’s his ability to break it all down and to things that people can clearly understand and his relentless focus on accountability and consistency.
Whenever anyone else is promising hacks or shortcuts or offering simple feel-good motivations, Dre argues that discipline is the real separator and he shows up consistently day after day. His website is calledAll Day Dre. That pretty much says it. In this episode, we’re going to be talking about self-belief, leadership and career reinvention. We’ll discuss why so many professionals unknowingly have their own potential. By reading or watching, my goal for you is to identify where you can release some of the constraints that you may be placing on yourself. You are going to feel Dre’s palpable energy. I’m convinced of that. I’m J.R. Lowry. This is Career Sessions.
Glad to hear it. Let’s get going. Give us your backstory. I know you fought your way into the professional basketball ranks. How did you do that? How did discipline help you in addition to being motivated?
I started playing basketball around the age fourteen. It was pretty late if you’re going to play in college, let alone play pro. There we played in high school, walked on the Division 3 level of college, which is not the level to produce as pros. I had to sell myself into professional playing opportunities, which I was able to do successfully. At the same time, I started publishing content on his new website called YouTube in 2005.
That’s where I started to build a name for myself online exclusively through this basketball training. I was just on the court doing drills and showing other players how to practice and get better. About five years into that, at the time, I’m still playing professionally. I’m playing overseas and traveling to different countries every year. I started to sell programs. I started to make training programs for basketball players at this time. Publishing became a thing and that’s when I started to write books. Also, athletes started asking me about the mental side of the game and when I started talking about those things, that’s when the non-sport professional started to find me.
They said, “The way that you break down and explain things, not only mindset but other aspects. This is useful for us. We don’t even play sports.” That’s how I knew what my segway would be out of sports into the next chapter of my life. We all know athletic careers are very short. When I stopped playing sports in 2015, I went full-time into working with professionals and entrepreneurs on not only mindset, but also strategies systems and execution, which is where we are.
Talk a little bit about when you talk about breaking it down in a way that resonates with people who aren’t professional athletes. How do you take somebody who’s juggling work and family and all of the related pressures that come with that? Explain what worked for you and the things that have been different makers in your life to somebody who’s just living that normal day-to-day existence.
The Four Pillars of Performance
The same things that work in any professional realm, the same stuff that works in sports. Sports is a great canvas from which to explain it, and that’s the reason I was able to translate it the way that I did. It’s those four pieces that I just mentioned. The first one is mindset. It’s the way that you think. The way that you think leads to how you speak. How you speak leads to what you do and what you do becomes your habit, your character, your virtue and your destiny. That’s starting off with just the mindset. What is the mentality around your behavior? If you want to change your behavior, you have to change the way you think.
That’s the first thing that starts. I don’t mean in a woo-woo motivational sense. If your mindset is leading you to take certain actions that are not getting you what you want, then we have to change the way you look at the situation so you can change your behavior. The second one is the strategy. Strategy is simply a plan of action. A plan of action does not have to be a 100-page SOP. A plan of action can be three steps like wake up, put your shoes on, and go outside. That can be a strategy as well. Strategy is the plan of action designed to achieve a clearly defined goal.
Systems Create Scalable Results
Interestingly enough, a lot of people operate with no strategies. They have a lot of talent, time, and energy but no strategies. What we usually do is deconstruct strategy from the gold back to the present moment. The third thing is the systems. The system is a set of steps to be followed that can be duplicated and repeatably. It doesn’t require the specific talent of any individual person. I can have a strategy that works for me because some of my talents are part of that strategy. For me to make it into a system has been duplicated by somebody who doesn’t have my talent, my knowledge, my experience and hasn’t been where I’ve been.
They can still execute it and get it done. The best example of this is if you look at Starbucks or McDonald’s. They don’t have to hire PhDs. They can hire people who can just follow instructions. If you can follow instructions, they can make it work. The last one is the execution. This is the biggest thing for professionals. What we usually call leadership just means execution done in a disciplined way over an extended period of time.
It’s executing over and over again. When you’re following the system, it’s usually a lot easier to do than when you’re having to figure it out on the fly even when you’re highly resourced, very talented, smart and you have a lot of energy. You eventually can burn yourself out if you don’t have a simple process to follow that allows you to put it on autopilot.
James Clear inAtomic Habits and others have certainly written about habits, but he probably is best known for the one who talks about the fact that you don’t rise to the level of your goals, but you fall to the level of your systems. Systems, as you say, allows people to put things on autopilot so that they become things that they do. Over time when you build those things, they do start to accumulate, and you start to realize that you can accomplish more and more bit by bit over time.
Yes, I agree. Having those systems in place, once you know what you want to achieve or you achieve it even by let’s say accident. You aren’t trying to do it systematically but you achieve it, then the next thing is, “How do I deconstruct what I just did to make sure that it works?” Again, this could be something as simple as how you like your hand towels folded in the bathroom. Also, be something much bigger like, “How did I close that deal? How did I get that prospect? How do I get them to this position? How can I do that over and over again so I can hire a salesperson and the whole team?”
You’re an entrepreneur. That’s a specialty important when you’re an entrepreneur or take something that you haven’t ever done, certainly in the context of your business. You do it. You start to figure out what will make it successful. You systematize it. You hand it off to somebody and if you’re a successful entrepreneur, you keep doing those things because you’ve got to focus your time on the things that are the biggest difference makers. You can’t do everything. You’ve got to make sure that you’ve got something that you can hand off that they will be able to pick up and be successful with and that takes skill, too.
That’s an important skill if you want to, at some point, let’s say exit your business or sell it to someone else if you want to bring other people into the business to replace you at certain jobs or if you want to pass it on to your kids. It can’t all be based on your individual talents. That’s where the systems and the ability to break things down and put them back together, which is my personal superpower. That ability works wonders when you’re trying to build systems for yourself or for others.
Talk a little bit about how you take some of those same things, the mindset, the strategy, the systems, the executions and you apply it when you’re reinventing yourself. You’ve gone through that yourself. A lot of people, especially as people are having longer careers, go through periods where they have to reinvent themselves. Talk about that journey for you and how you applied some of those same practices. The four things that you’ve talked about when you shift it out of your professional basketball career and into some of the things you’re doing now.
Reinvention Requires Identity Shift
Reinvention happens when your identity is too small for your ambitions. When you see where you want to go in the future, but you look at how you currently see yourself. You see that this person is not going to match that future. That’s when reinvention happens, and it starts on the inside out. I’ll use myself as an example. The first step is, when I’m moving into entrepreneurship. The first thing is I have to get my mind out of the athlete’s mindset. Out of, “I’m going to solve this with physical exertion,” which is what athletes do.
If I have a challenge, I see that by going to the gym, working on my game and getting better. Winning the next game even though I’ve lost the last game. In business, you can’t do that because that’s not the way the game is played. It’s played out in a different way. You have to reshape the way you see yourself and reshape who you see in the mirror so that you start thinking automatically more on a business level than on an athletic physical exertion level. That’s an example of a mindset piece.
As far as the strategy piece, it’s finding people who have already solved this puzzle, who’ve already figured out, “What can I take from what I did as an athlete? How can I use this in a professional world?” I was fortunate enough to have mentors in the game who would say to me, “Dre, you have this framework, Work On Your Game®. You have this idea.” Work On Your Game® is very useful because in a professional world, what people like about athletes and you asked me this question. They like the fact that you have to show up every day as anybody with a job does. You have to be disciplined and do your work even when you don’t feel like it.
There are times when things don’t go the way they’re supposed to. In sports, that’s losing a game. In business, it can be a myriad of things. You still have to keep showing up and its competition. A lot of sales industries and a lot of athletes, because we’re used to competition and we can deal with the back and forth, the ups and downs we’re going through. You have to move yourself to perform at your highest possible level because you’re competing against a lot of people to keep it up at the top 2% of the sports world.
In the professional world, employers love people who are going out there and trying to compete. Maybe not against other people, but often against themselves. Against the benchmarks and against their quotas. How can you take all that stuff? This is what was told to me, “How can you take all that stuff and make it translatable for someone who has never picked up a ball?” Again, as I’ve told you. My superpower is my ability to extract from one place and be able to communicate it to another place so I can talk to someone who’s never played basketball before. Within ten minutes, I can have you pretty well understanding the game and anything else.
If you were to explain to me something that you know at a high level that I never heard of, about an hour of conversation, I can understand it enough that I can take ten minutes and help somebody else get about 68% of the basics of it. That’s what I did with my experience as an athlete. I begin to translate it to the professionals and at the same time you update your formulas while you’re learning. As I’m talking to more entrepreneurs and more professionals, I’m finding out what their challenges are and what they are dealing with.
They had to deal with superiors. They had to deal with middle management. They have to deal with teams that they inherited that they did not choose. It’s the same thing as sports. You deal with different types of leaders, teammates, and opponents. You’re on different teams where you may not like the situation, but you’re signed to a contract. You still have to show up and do your job. All of these pieces are translated out of the sports world into the business world.
There are two follow-ups I want to ask you about from what you just said. One, you mentioned earlier that you played in a lot of different countries. You had to fit into a lot of different teams and a lot of different international cultures. How did you learn to become more adaptable through that process? I’m sure that was a key requirement for your success.
In the Sports world, the good part about it is that basketball is universal. It’s a universal language. I remember I was playing in Herceg Novi, Montenegro and my coach did not speak English. None of the coaches spoke English, and I don’t speak any other languages. I know a little bit of Spanish, but they don’t speak Spanish over there in Herceg Novi. I had two teammates who could speak English and they would be my translators. The good thing about that, I always joke is that if the coach talked to the team for 30 minutes and the teammate gave me the translation. It will be like two minutes long, so I could always pretend that I don’t know what the coach said because I literally didn’t know what he said.
On the courts, the certain movements of basketball and certain things that can be communicated, like pass here, set a screen, or grab the rebound are universal languages. As long as I had the basketball skill, we could communicate on the court to a certain degree. As far as off the court, by the time that I started playing in 2005, a lot of the people under the age of 30, are heavily influenced by what goes on in America. They watched our TV. They are looking at our internet and listening to our music. They’re watching our entertainers, so they speak English pretty well.
That was under 30 then. By now, it’s probably 50. A lot of people speak English pretty clearly. They understand the stuff that we pay attention to. Though, there were always some people in town, whether they were players, teammates, or just people who were fans of the local team. They would come find me and I would make friends with them. They could show me around town. Tell me what to do and what not to do. It was a pretty smooth transition almost everywhere that I went. Also, keeping in mind that you’re an athlete traveling the world to play sports. I’m 6’4”. If you’re a 6’4” Black guy walking around somewhere in Eastern Europe, they know why you’re there for the most part.
That’s probably true. The other thing I wanted to ask you is when you shifted out of basketball and into your business career. What was the hardest part of that transition for you?
One is that you have to get used to doing “real work.” A lot of athletes don’t like when I say that. The reality is, when you’re an athlete, a hard day of work is four hours. That’s a two-hour practice in the morning and two-hour practice at night. If you have a game, that’s 2 or 3 hours. That’s a work day. When you’re an entrepreneur, you’re a professional, especially high performing professionals, eight hours is like you’re slacking. There are much longer days. Also, as a professional entrepreneur, there’s always more work to be done.
We have to pull ourselves away from the desk. Pull ourselves away from the office. There’s always more that we haven’t completed that we could be doing. It’s a lot more work, especially when you’re trying to start a business, get it off the ground or establish yourself on a certain market. It’s a market penetration. You have that and also getting people to respect your name and know who you are. When I first stopped playing and came into the business world talking about these concepts, but not exactly what we’re talking about exactly here because it’s been some time.
At first, they are looking at me like, “It’s cool that you play basketball, but what does it have to do with us? How can you help us? Do you have any Bonafide’s in this space working with these people? We know you can be basketball players but what about us?” You have to establish yourself. You got to prove yourself. A lot of athletes may not want to do that work, because it is a lot of work to get yourself established as, “Don’t let me see athletes. Looking at me and seeing this person in this space.” They happened to have been athletes. By this point, I’ve established that but at first, that was not established.
When you were doing that, it sounds like this goes back roughly twenty years at this point when you were first getting into this thing called YouTube and producing content. You were probably a bit ahead of that trend in terms of making that transition. I’m sure you had to learn a lot of hard lessons along the way.
Yes, and a great thing was that what we now know is social media was just coming out right when I got out of college. I graduated in 2004. Facebook comes out about the next year, then you get all the other social apps and then it becomes easy to go direct to the consumer. You didn’t have to go through a middleman to publish a book, to have a radio show, which we call podcasts, and have a TV show as we call YouTube. The middleman was all going.
There were no barriers to entry at the exact time that I was looking to figure out what I am going to do professionally. Athletes started thinking about those things but also, all people now could do them because there was nothing blocking anybody from putting himself out there. It’s a fortuitous bounce, we could say, with the way the world went for me to be able to do it.
I know you write and speak a lot about presence. I will tell you your presence is palpable even though we are on video here together. I can sense it right from the beginning. Talk about how you build presence. Not everybody will have the natural presence that you do. For somebody who feels like they struggle with that or people often get told, “You lack executive presence.” How do you coach them on building their own form of presence?
That’s an excellent question. Also, a lot of professionals work in organizations who come with that exact challenge. They have a leadership or authority position on some level, but the people who they allegedly have authority over don’t listen to them. They’re asking them to do things that people aren’t following through, or people are taking their orders as suggestions. Their higher ups will say to them, “If you want to get this promotion, you need that executive presence because we can’t put you in charge of more people if the people are not listening to you.”
Presence Under Pressure
It’s an excellent question that you’re asking. First, let’s get clear what presence is. Presence is discipline embodied under pressure. It’s the same things done the same way every time consistently following a structure and then the under pressure part doesn’t necessarily mean like you’re sweating bullets and there’s a gun to your head. Under pressure just means things are not normal. Everything is not easy and comfortable. That’s what under pressure means. As soon as the situation goes off kilter, that’s under pressure.
Can you maintain your presence of mind? Maintain your state, maintain that discipline, and that collectiveness, even when things are not going the way that you want them to go. That’s what presence is about. How can someone develop their presence? The first thing is you have to learn to quiet the mind. Quieting the mind means not allowing whatever outside noise is happening to throw you off the game that you’re supposed to be playing at the moment. It’s lessening your reactivity, your output, and the noise going on in your mind and noise that you put up.
In our presence, we talk about four specific things. The first one is groundedness. Groundedness just means being rooted in the reality of what’s happening in the moment. If you listen to the biohackers, there’s a lot of them down here in South Florida. They talk about when you start the day. The best way to start the day is to get some sunlight while the sun is still coming up because the UV rays are not as strong. You want to let your bare feet touch the ground. Touch actual grass or dirt or something like that. These days, some people would call it touching grass, like you need to touch grass. What does it mean? It means you’re connected to what’s happening. Connected to the Earth.
Groundedness means you are focused on the present moment. Where you are is where your mind is. Your mind and your feet are in the same place. What happens with a lot of people these days is that their mind is somewhere way different than where they’re at physically because there’s so many distractions that we have. It’s like a person. They’re at the park playing with their kids, but with one hand, they’re looking at their phone. Mentally you’re in one place but physically, you’re in another. That’s the opposite of groundedness. Groundedness is where you are.
The second one is stillness. Stillness means reducing your mental output. What’s coming out of you through what’s going on in your mind. In other words, if you are angry or frustrated, not allowing that anger or frustration to show through what you’re saying or through your physical presence. The third one is containment. Containment is lowering of the actual tangible output things that you do. Not doing more than you need to do. Not fidgeting. Being able to stand still. Being able to maintain actual solid eye contact. Not reaching for your phone every five minutes when you’re standing at the airport gate waiting for your flight.
It’s physically not moving when you don’t need to be moving. Stillness and containment are about the emotional and the physical, keeping it in. The last one is calibration. Calibration is about you offering a proportionate response to the situation at hand. If you ever see somebody overreacting, that’s an uncalibrated response or somebody under-reacts. When someone’s calibration is off, then they can say all the right things, but the message doesn’t quite land the right way. When you get those four things aligned groundedness, stillness, containment and calibration, that’s when the signal of all those aligned comes out as what people call presence.
How do you factor into the idea of being both decisive in these moments of pressure and also being empathetic?
Leadership Demands Distance
Being decisive is about coming up with all other options. The word decision comes from a Latin word. The root of it is a Latin word means to cut off. That’s what a decision is. You’re cutting off everything else and this is all this way. When it comes to being empathetic, it’s about understanding how other people feel. Maybe not necessarily feeling it yourself, but understanding somebody else’s feelings. What a leader must do and this is something that I’ve told people for years. A leader has to have the ability to disappoint people at a rate at which they can accept a leader.
A leader cannot please everybody. You cannot lead people and need people at the same time. That’s not possible. As a leader, you can’t be the class clown and everybody’s friend. Even if you want to be, you can’t do that as the leader because you lose authority. Leadership requires a certain amount of distance between you and the people that you’re leading. The empathy part is helping people understand, “I know this may be disappointing to you. However, this is the decision and this is the way that we’re moving forward. You can let me know how you feel about it and what you think about it. Most importantly, let me know what you need from me so that you can best help us as a team move forward with the decision that has been made.”
That needs to be communicated in a calibrated way in a way that people understand that I’m not asking you if you’re going to follow it. I’m telling you this is what it is. I’m asking you what you need from me for me to best help you and follow through on what we’re going to do. It’s an important point with people who need that presence. You have to be able to communicate this in a way that you don’t have to say what I just said explicitly, but people should still get the point. That’s what leadership is about.
How do you demonstrate that presence in the absence of pressure? There are going to be moments in business where you are not fighting for your life. You’re not on the playing field metaphorically as you are when you’re an athlete but they’re just in the everyday moments. How do you show presence when the pressure isn’t as present in the room?
It is when you establish, first of all, from the beginning who you are and how you’re showing up. How you walk in the room is how you walk out of the room. You have to establish yourself as that leader even when you don’t have a leadership title because that’s what gets you promoted. You can be competent but you don’t get promoted just because you’re good at the job. You get promoted because the people who are promoting you see you as someone who can lead and inspire others who are going to be doing a job once you move up. Not just because you can outpace everyone else.
It’s the way that you show up on a consistent daily basis. Being present with people when you’re talking to them. Being able to motivate and inspire. Being able to set the tone and setting the bar and the standard. Upholding the standard to where other people look at you when they’re trying to figure out what to do. That’s what makes you a leader. A boss is a person who can tell people what to do and they have to comply.
A leader is a person who gives other people to do something because they want to. They see you and they want to get to where you’re at so they start following you even though there’s nothing that says they have to follow you. That’s how you start to establish it even when everything is calm and normal. Human beings are social creatures. We are oriented to follow the leader. Who is the leader here? Who’s going to take that leadership position? Even when no one has been appointed. You put a group of people who never met each other together, get them stuck in an elevator and somebody’s going to take the lead. Everybody is going to be following the lead of that person. That’s just human nature.
Who is that person who is calm? They seem to have an idea of what to do. They’re willing to take on the risk of possibly being wrong. |Everybody else who would rather follow them than make the decision themselves get behind that person when you carry yourself in that way. Again, it’s not something that you announced. It’s all in your energy. People have to remember that 85% of communication or maybe more is nonverbal. It’s not what you say. It’s how you carry yourself. It’s what’s being said, even when you’re not talking. People get a pretty good read and understanding of who you are and what you’re about before you even open your mouth. That’s where you establish leadership.
I would imagine you work with early tenured people as well. What do they misunderstand? For example, when an individual contributor becomes a manager or when that frontline manager becomes a manager of managers about what’s required to be successful at the next level.
The first thing is they have to understand that a certain amount of distance is required. Leadership and authority requires a certain amount of our distance between you and your subjects. Meaning you can’t be the one joking in the lunchroom the way that you were before. You can’t do it because it undermines your authority. People see you as a peer and they see you as a friend, then when it’s time for you to use that authority, they’re going to be offended by the fact that their friend is trying to tell them what to do or what not to do.
It’s accepting the fact that leadership comes with it in a package deal. A little bit of distance, and a little bit more isolation. A lot of people, when they ascend to management, don’t want to deal with that isolation. They’d rather be part of the group. This is just a human thing. Many humans would rather be part of a bigger group than part of a smaller group because they feel more connected, but that’s the reason why leadership is a burden. Not only just a reward. That’s one thing.
The second thing is that, what got you here is not the same thing that’s going to get you there. What was working for you to move up? It was you doing the job and also showing the leadership tools but when you move up to a new position, you have to adjust to that position. Adjusting to that position means figuring out, “What works here?” What worked there versus what’s going to work here. Usually, if you got promoted, you got moved up or promoted, the people who promoted you know what it takes and they’re going to tell you.
What I find is, a lot of times, people either are confused by what they’re told. They don’t know what to do with it or they hear it and reject it because it seems a little bit cold and a bit distant. “I don’t want to be that type of person,” as they say and then they go out and try to do it their way. It ends up not working and now they’re stuck. It’s heating the advice from the people who already are in the position that you’re in and asking yourself, “How can I develop more of that?” A lot of it is not technical. It’s not to say, “Push this button and send this memo.” It’s all in a way that you’re carrying yourself.
Again, that 85% of communication is nonverbal. That’s where leadership lives. It doesn’t live in speeches. It doesn’t live in memos. It lives and that communication. When people can feel that energy, they can peg you as a leader, even though they don’t know who you are. The example I get from people is that if you were watching an Amazon board meeting. We were just watching it on camera and I turned the sound off. You can’t hear anything anybody says. You don’t know anything about Amazon.
I would ask you after about ten minutes, “Who’s Jeff Bezos?” “He’s the guy who runs the company.” “Point him out.” Everybody can point him up and why is that? You’ll see everyone in the room orienting towards the boss, the leader or whoever it is. People physically orient towards them in a way that you can tell even if you can’t hear what’s being said. It’s the same thing with human beings in any environment.
You’ve taken a lot of initiative in the course of your career. There’s clearly an entrepreneurial bent to the way that you think. A lot of people seem to be waiting for permission. How do you coach them to become more the masters of their own destiny?
The number one thing is, even if you are not an entrepreneur in name. You must be an entrepreneur in spirit because even if you don’t own the company, you own your career. Where do you want to go? You own yourself because one day, you’re not going to be working here. Whether it’s the day you retire, or you change companies or you change Industries. Where do you want your career to go? What do you want your career to be about? You have to take ownership of that because the company that you’re at, as long as you’re doing a good job, they’ll keep you. Is this where you want to go?
If you want to go somewhere else, then you need to ask yourself where is it that I want to be, and what is required there? The first step again is not the technical skills. It’s the interpersonal abilities, presence and the, how do I see myself when I’m looking in the mirror? You carry yourself in a certain way that makes people know without you saying it and without them asking it. They’re like, “This person looks like, they feel like the type of person that we want in this position that we need fulfilled.” It’s not necessarily, “Do you have the skill?” Skill these days is a dime a dozen.
I’m not saying that skills don’t matter. Develop your skills, work on your game and get better at the technical tools. Skill can be easily replaced by a lot of people. Most of the people reading, there are 100 people in your industry who can replace you and do the same job that you’re doing with the similar training that you have. That’s not what makes you valuable. What makes you valuable is how you are as a person. Not who you are.
In the venture capital world, what a lot of them would say is that when we’re looking at an entrepreneur and deciding who to invest in. We’re not asking for someone who has all the answers or necessarily the best product because you never know what’s going to work. You invest in some and you think they’re going to be amazing. They’re trash and you invest in some and you think there’s going to be small then they blow up. We’re looking for someone who is magic about to happen, someone who was frightening in a bottle. That’s a feeling. That’s not a technical thing that you can write down and count.
Do you feel like lightning in a bottle?
Yes.
What’s the mix? Tell us about the mix of business things that you’re doing.
The main thing these days is our execution reliability. Execution reliability is all about how you show up consistently and execute the way that you’re supposed to execute. Upholding the standard, following the disciplines and getting done what needs to be getting done. Especially in organizations where the biggest challenge is not strategies or skills or mindset even. Its execution drifts.
Slowly, over time, human beings when not corrected or checked or held to accountability standards slowly drift off the path of what they’re supposed to be doing. Not because they’re trying to, but because without parameters and rules, you get chaos and disorder. Execution reliability is all about making sure that companies at scale even as they expand, everyone stays on the process. That’s our main focus.
Thinking back to when you started this journey, what something about leadership that you felt back then that you’ve changed your mind on since?
The number one thing with leadership is about how people are responding to you, not necessarily about what you know. I’m a high processing person. I could explain for hours any subject and I like doing that, but that’s not what makes people follow you. That makes people think that you’re smart but doesn’t make them follow you. What makes people follow you is the energy and that’s much less about what you say. It’s much more about how you carry yourself. What makes you a leader has nothing to do with talking. You talk, give speeches and say things, but that’s window dressing. Real leadership is just about who people decide to follow when they have a choice.
For our audience, that’s trying to figure out what to do who has a career, uncertainty and maybe they’re facing layoffs. We’ve got a lot of that going on. AI is looming in the background as this threatening thing that a lot of people are feeling. What advice would you give somebody about managing their career over the next 3 years, 5 years or even 10 years?
I Cannot Replace Human Judgment
AI is going to replace a lot of duplicatable tasks. It’s already doing that and it’s going to continue to do that. It will be a long time before artificial intelligence can replace human judgment. AI cannot do human judgment the way humans do judgment. Your ability to discern, lead, and make tough decisions when you have incomplete information and when you have unclear information. They’re a lot of different choices you could make and they all look equally good and bad. What you do in that moment and how you can get other people to remain confident and steady by following your energy. There’s no artificial intelligence system that can do that, because the human touch cannot be replicated by a computer chip.
At least not yet. Any last thoughts you want to share with our audience before we break?
The biggest thing is that execution is what makes the professional organization a professional organization and also the professional as a person. Continually doing what the standard says to do even under pressure.
There’s lots of good lessons here. You are clearly a coach and teacher. It comes across as strongly as your presence, Dre. I know you enjoy that. It shows just even in the brief conversation we’ve had. I appreciate that you reached out to me to get this set up and it was good to talk to you. Thank you for your time.
Thank you for the time and for sharing your platform.
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What a fabulous discussion with Dre and so much practical wisdom that he shared. The first thing to understand is that you have to take ownership for your career. Dre describes people being constrained by a lack of ownership. Not necessarily a lack of talent. Those who are consistently advanced are the ones who stop waiting for these external validations, and start treating their careers like they’re the CEO of their own business.
As Dre said, you don’t necessarily own the company, but you have to own your career. The second thing is that discipline creates opportunities that motivation alone never will. Sustainable success comes from the things that Dre talked about such as mindset, strategy, systems, and execution, doing that stuff day in day out, even and especially when you don’t feel like it and when conditions aren’t perfect. That’s when everybody else gives up and that’s when you start to stand out.
The third thing is that leadership starts with self-leadership and building presence. That presence piece that they talked about comes in moments of pressure where you’ve got to demonstrate that groundedness, the stillness, and being connected to what’s right in front of you and not distracted by the many things around you. That’s something a lot of people struggle with. It’s frustrating for rising people in their careers because they often get told, “You lack executive presence,” and then they ask what that means. They don’t get a good answer.
Dre gave some practical advice there that you can apply whether you’re an Individual contributor, a new manager, a leader, or even in the C-suite. Lots of good advice from the discussion. It was great talking to Dre. Again, thank you to him for joining me. I invite you to subscribe to Career Sessions onApple Podcasts,Spotify andYouTube or any other platform that you happen to use. If you found this discussion enlightening, which I hope you did, please join my membership community which is calledPathWise and subscribe to our newsletter PathWisdom. Thanks.
Dre Baldwin built Work On Your Game® to turn disciplined execution into dominance. A 4x TEDx speaker and 43-time author, Dre played pro basketball for 9 years. Today, he helps experts and entrepreneurs install mindset, systems, and strategy to scale from six to seven figures with presence and power.
The Leadership Lesson I Learned By Becoming My True Self, With Katherine Dudtschak
July 20, 2026
What if becoming a better leader has less to do with learning new management techniques and more to do with becoming more yourself?
In this episode, former RBC executive and HomeEquity Bank CEO Katherine Dudtschak shares a deeply personal journey that transformed not only her life, but also her philosophy of leadership. After publicly affirming her gender while leading thousands of employees, Katherine discovered that vulnerability, compassion, and authenticity weren’t leadership liabilities. In fact, they became her greatest strengths.
In this episode, you’ll learn:
Why success and fulfillment aren’t always the same thing
How fear-based leadership limits both people and performance
Why vulnerability builds trust faster than authority
How curiosity and compassion can outperform command-and-control management
Why doing the inner work is one of the most important responsibilities of a leader
Practical ways to lead with greater authenticity without sacrificing results
Whether you’re leading a team, navigating your own career, or simply questioning whether the life you’ve built truly reflects who you are, this conversation will challenge the way you think about leadership and yourself.
If you’re interested in the impact of capitalism on leadership and innovation, make sure you tune in.
Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.
Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/katherine-dudtschak/
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Watch the episode here
Listen to the podcast here
The Leadership Lesson I Learned By Becoming My True Self, With Katherine Dudtschak
The Success Gap
This conversation is about something that a lot of people spend their entire lives or much of their lives awaiting, the gap between success and truth. My guess is Katherine Dudtschak, a former Senior Executive atRBC, former CEO ofHomeEquity Bank, one of Canada’s most accomplished business leaders and now the author ofSincerely, Katherine. At age 50, while leading thousands of employees and one of the country’s most visible corporate roles, Katherine publicly affirmed her gender identity.
In doing so, she triggered a question that goes beyond gender or identity politics. How many people are living lives built around expectations that they never consciously chose? We live in a world that is very focused on achievement, productivity and image. What does that cost us if it’s not true to who we are? Why does reinvention, particularly midlife, feel so threatening? We’re going to be talking about leadership and conformity and the tension that exists often between success and internal alignment. I’m J.R. Lawry. This is Career Sessions.
It’s wonderful to be here with you and all of your guests.
I appreciate your joining. You’ve got a new book out. It’s been a few weeks. Thanks for putting it up there for those who are watching on video, it’sSincerely, Katherine. You describe what many people would consider to be a successful life before you realize that something was missing. Something very important was missing for you and you made it a very visible, personal transition while in a big leadership executive role. How did that change the way that you view authenticity and people? Particularly those who are in an executive leadership role.
Defining Masculine And Feminine
It changed a lot. I’ll give you some backstory. I was known as a fairly empathic leader before June 17th, 2019. The reason I share that is, it was around the year 2000 that I definitively cried at work the first time. I think of human behavior as either masculine behavior or feminine behavior. There are feminine and masculine attributes in every human being. There’s a unique mixture in each of us. We would describe/showing sensitivity or emotion at work as a feminine behavior. Not female, but feminine.
If you look at my essence in childhood before my parents, community, and school tried to shape me into behaving a certain way, or performing a certain way. I would have been a fiercely curious human being. I would have been a sense-making systems thinking human being, which are more mechanical or masculine characteristics. I would have equally been highly emotive, highly sensitive and expressive. I started to embrace my more sensitive side in around the year 2000. I got to be known as a fairly empathic leader.
When I affirmed my gender in 2019, I had come through a 24-month period of deep heavy mental health challenges. I was suicidal the year before I came out. I thought it would have been better for my life to be over. I built the perfect career. I had four beautiful children and got married. It was the perfect life in materialistic terms, yet I was complete. I went through a dark period, then a friend pulled me aside who could see my symptoms. She’s a psychologist or psychiatric nurse and she said, “Do you want me to send you research on the intergenerational trauma caused by suicide?”
The Dark Period
She literally walked me off the cliff. I ultimately made a pledge to myself to come out in my job leading 25,000 people at Canada’s largest company. I was in one of the most senior executive jobs in the country. I didn’t come out of that job because it was going to be popular. I came out in that job in order to keep my job and be able to finish putting my children through school. Right up until my coming out, I expected to be homeless. I expected the worst. Partly, because I had childhood trauma associated with fears of abandonment and fears of rejection.
Everyone was saying, “You’re going to be met with such love and such embrace,” yet I feared the worst. What happened in that moment of my coming out or of the video going out to the world is I started to receive hundreds and eventually thousands of emails from people about bravery and courage. Neither of those are sexy words. Bravery or courage is about moving forward with something to be true yet fearing the worst. You’re in the presence of fear but you’re moving forward because you feel you need to survive.
I expected the worst, yet I got all these emails about bravery and courage and people started volunteering their own life stories to me. Aspects of identity that they had hidden from the world. Aspects of hurt and hardship that they had never told anybody about. Yet they are writing to me and they are from all walks of life. A gentleman from the East Indian Community talking about ostracizing his best friend in India who had told him he was gay. Who later took his life because he was put into an arranged marriage. He carried that guilt forever.
There was a woman talking about emotional and physical abuse from a former spouse. The stories were countless. The fact that I was fairly empathic before and trusted, then I showed high vulnerability in my coming out. It resulted in me being met with a level of trust that humbled me to the core and because of the kindness, the empathy and the embrace that I received and because of the trust I received from others telling me their stories. This gets to the root of your question. I was forever changed as a human being.
Redefining Leadership
When you get to see into the soul of others, and they trust you with such vulnerability and to be embraced the way that I was. It’s pretty damn hard to go and be a command and control manager after that. It’s pretty hard to be a dictator after that. I was immediately changed. I could no longer be directive in the way that I might have been in the past. I learned how to suspend my own anxiety and my own fear of meeting targets and expectations as a manager. I learned how to suspend that and shift my manager’s approach or leadership approach to kindness and curiosity.
Kindness and curiosity that would lead to empathy for what people are sharing with me. I became a much flatter leader. My executive team would tell me they knew what the root cause of a problem was of what we were trying to solve. It didn’t feel right intuitively to me, so I would go to the front line employees and say, “Tell me what’s going on here.” The front line employee goes, “It’s this, this and this.” I go, “What should we do about it?” They’d go, “We should do this, this and this.”
I go back to my executive team and I go, “We’re not listening. We’re not showing empathy and listening effectively to the people that know the best.” Everything got turned upside down for me because I saw a side of the human condition that I didn’t see at scale before. There’s so much hurt or conditioning that occurs that causes people to not share. I became so much more compassionate, empathic and curious that my leadership style changed forever to being much more human-centered and much more heart-centered. The funny thing is, our business performance was record-breaking through the entire period of that.
It’s a significant personal change for you and in what you revealed that day, but also in what happened afterwards. Having now reflected on that, do you feel like the corporate world is evolving or are they still stuck in the mode where leaders need to be these personas and can’t be their authentic selves?
Yes and yes. Both are true. There are pockets of light everywhere of humble, selfless, heart-centered leaders that lead with kindness and curiosity, show empathy and compassion. Take input from all levels. All corners of the organization. That’s what inclusivity is. It isn’t fancy. It takes psychological safety and belonging, but it’s about getting everybody’s input to come up with more holistic solutions. There are leaders like that everywhere. Many of them are flying beneath the radar. Not because they’re shunned necessarily, but because the organization and senior management is under so much pressure to perform.
Nobody takes enough time out to see and understand what makes this more human-centered, heart-centered inclusive and compassionate leader effective. There are bright lights everywhere. There are also and I saw it, at the most senior levels, there are very human-centered, planet centered senior executives and CEOs. The challenge we’re dealing with, and it’s a Western world, if not global societal issue. For a long period of time, we have built a world that is extractive and performative. We’ve been on a path for several thousand years that have created this consumerism, capitalistic, extractive and performative world that we live in.
It’s not good or bad. It just is. That extractive world has quarterly performance targets, quarterly reporting, risk management, board governance, a set of linear, logical, mechanical practices that keep CEOs and senior executives on this performative treadmill in order to keep the governance, the risk management and the production of the organization moving. It takes a lot for a senior executive to be able to pause that and embrace more regenerative and more coherent ways of leading and running a business.
Even the attempts of ESG have been pushed backwards. It’s hard. There’s great people everywhere, and great intentions everywhere. Yet they often get masked by the performance pressures within an organization from the top down, to perform and to deliver. It takes a very conscious leader or a very aware leader who is conscious of their own behavior and their own tendencies to create enough space to pause the anxiety associated with that performative way and create enough space in their day and in the way that they lead to be more human-centered and heart-centered.
It’s why I speak at Sincerely about the pathway to a regenerative world and a coherent world. It starts within the leader himself in order to create calm and peace within ourselves so that we can shift from anxiety or fear-based ways of being to kinder, more curious and inclusive ways of being. Both are true. Is it shifting? Yes. Is that at the pace it needs to? In order to save humanity and our relationship with nature and the planet, I don’t think it’s moving fast enough.
A lot and what you just said, both the notion that the way that we approach leadership has flaws but also the broader environmental consequences of it. Talk a little bit more about what that journey was like for you as you evolved your own leadership style and discovered that you could lead people in a very different way than perhaps you would have been leading up until that point.
I’ll give you 3 or 4 data points. The first time I cried at work was around the year 2000. A gentleman that was reporting to me, who I idolized, who I was junior to at one point. Now, I am a senior too. We were doing their leadership review, and it called out that they were risk adverse and they were pensive as a manager. I said to him, “You’re called out as risk adverse. Where does that come from?” He trusted me and he started to cry. He said, “Every time my parents made a risky decision, they failed. As a child I promised myself I would not take risks that would result in failure.”
He’s bawling his eyes out and I started to cry because I felt his pain. I also felt that he trusted me with a side of himself that he had not shared before at work. That moment for me was the beginning of learning to slow down and get to know the whole human being that you work with. That it’s okay to cry at work. It’s okay to be sensitive and to be vulnerable. That went on. I led the restructuring of a bank across nineteen countries in the Caribbean. I was the CEO. The restructuring by the board was seen as wildly successful.
The company went from losing money to back to sustainable profitability in less than 24 months. The board was blown away, yet I was heartbroken because in these small countries of the Caribbean, we reduced 40% of the workforce during that period as part of the restructuring. Employees didn’t trust management anymore. They were going to the media. I said to somebody, “We need to tell them the truth that we’re losing money. We need to tell them the plan to restructure the company.” The person says, “We’ll tell them when we’re done,” and I go, “They’re adults. They deserve to know.”
Every six weeks, I’d have a call with 6,000 employees. Eventually 5,000 and eventually 4,000 and I would cry with them because I got questions and I didn’t have answers. I said, “I’m sorry. I’m sorry this is hard and I’m sorry this is heavy. I promise you I will do everything in my power to save this company and as many jobs as humanly possible.” As soon as I was honest and vulnerable, I would cry alongside the employees, not out of weakness but just out of feeling. They stopped going to the media and employee engagement on the team over that 24 month period went up over 20% at the same time we restructured.
Again, I learned that it was okay to be human. It was okay to be vulnerable. Everybody deserves to be brought on the journey, then I came out. I went through my own personal transformation. Now, it’s not a corporate transformation. I was met with the level of love, kindness and trust that I shared with you earlier and it changed me. I had to lead in an inclusive way with compassion and less command and control. I focused more on inputs or activities and behaviors. Less on financial outcomes as a leader. Again, we went on to achieve record performance and this was the turning point.
I’m now living in a woman’s world. Not a man’s world. I’m worried about being judged for being too feminine and too sensitive. I was carrying that, yet I became an enigma. I was in my mid-50s and at that point, I made a decision to leave. Amazing company that I spent 37 and a half years at. Yet I had grown so much as a human being, neurodiverse, lived in a man’s world, lived in a woman’s world, and grew up as a poor farmer to war surviving immigrant parents.
I had made sense of all of this stuff but I got to a point where I said, “I need to leave. I needed to leave,” because so much had changed for me that I needed another chance to meet new people where they’re at and have them meet me where I’m at and move forward from there. In that case, I chose to leave a company I had spent many years at in order to not start over but start clean. Start from a clean place. I wanted to prove to myself, myself as a woman, and also as a heart-centered leader, that it wasn’t a fluke.
I became a CEO of another bank and within 60 days or 90 days, we were achieving record performance just by showing compassion and sensitivity to employees and giving them permission to come together and work side by side with their peers to come up with creative solutions. The company’s mission was all about approving the quality of life of aging people, people 55 years of age and older. We started to achieve record performance. Again, this more compassionate heart centered leadership worked and I just needed another chance.
I wanted another opportunity to prove it. As you know, I’ve since moved on from that and now, I’ve set up my own company called Sincerely. There’s 3 or 4 events in my career that groomed me, that opened my heart and opened my mind to a more compassionate inclusive way of leading where I learned to suspend fear and anxiety, but it didn’t happen overnight. It’s about going on a journey of inner discovery and self-discovery as a manager that brought me through that fifteen-year period to the point that I’m at.
Listening to everything you’re saying and thinking about what you said earlier in the conversation, Katherine, about the fact that we’re in a culture where there’s all this constant quarterly pressure to deliver. In the scheme of things, if I think about the way that most leaders need to perform as a piece of advice. A bigger piece of it is the lack of willingness to do the inner work. We end up with these cultures.
I’d love to get your view of having observed things from multiple lenses, living as a man, living as a woman, being able to see how a change in leadership style played out in your case at least. It feels to me like we’re living in this regime of command and control, top down and managing through fear and all those things that you’ve mentioned and threatened in through what you brought up so far. A lot of that persists because people just aren’t as willing to look within themselves and find a better, deeper, richer way to lead.
It starts with looking within. It’s also important to be kind enough to ourselves and realize that this extractive and performative world is all around us. It’s been built over several thousand years and it’s been intensified in the last 50 years in a way that’s become almost unimaginable and would appear to be unsustainable. In the world we’re living in, the level of social fracture and the level of economic divide between countries or people and the level of planet degradation and the level of over-information and disinformation. Those four forces combined, social economic, planet, and volume of disinformation and information is unmanageable for any human being, I believe.
I don’t think we were built to deal with that much anxiety and pressure from the outside world. It doesn’t just exist at work. I have four children. If there’s one thing that my former spouse and I did well, it’s that we did not jam our children into an excruciating schedule of extracurricular activities. We would go visit family in the country on most weekends or go to a family cottage where we would hang out in the wilderness and the outdoors as a family.
Since I have four kids within four years, they became best friends with each other, but we did not have this performance intensity day and night. We had some relief in our life. This idea of an extractive and performative world is all around us, consumerism is a byproduct of it. The way companies run is a byproduct of it. This going inward is more than being a manager or a leader. It’s a human journey. It’s a human journey to say, “I am not at peace with the level of pressure and anxiety that exists in my life because of family, spouse or my job. I want to go on a journey to calm my nervous system and find some peace within me.”
Taking the time and space to go Inward and be reflective is more than management. It is about life. It is about going back, finding your way back to your true essence as a person, and finding a level of inner common, inner peace within you. At Sincerely, I describe the world we live in as extractive and performative. I describe the world we have the potential to move towards, which is regenerative and coherent. What I mean by coherent is a world where the human being lives from their essence, their essential self through their physical and inherited self, genetics outward through our lived experience.
Back to performative. Most human beings are taught from a very young age to suppress parts of our identity to fit in. It’s like, “Don’t be too expressive, Katie. Don’t be too sensitive, Katie. Learn to talk with a deep voice. Don’t be creative. Perform.” Most of us have aspects of identity we suppress throughout our life. That creates a level of anxiety within our nervous system because it’s not natural. What we have is a society that values education or a job resume. It might value whether you’re male or female, but it doesn’t value what are the unique human traits of J.R.
Moving to a world that is regenerative and where you as a human being are more aligned and coherent, involves going inward to revisit that inner child and learn to love and like the parts of yourself that your parents might have told you were not appropriate or your teachers might have told you weren’t appropriate. To heal that, and to ultimately create habits in your life that calm your nervous system like meditation.
I meditate now twice a day. I lead a very quiet life. I used to go from 6:00 in the morning till 11:00 at night every day. As an executive, that doesn’t happen anymore. Making conscious choices to go inward and learn to love yourself and to create peace and calm within yourself is a human journey that leads to coherence that allows you to become a better leader and also a more whole and complete human being.
Now that you’re doing what you’re doing with Sincerely and have shifted out of the corporate world. You’re out speaking and writing on this. What are you hearing from people about how to practically incorporate some of the things that you’re talking about into the way that we run our world day?
A few things and I’ll be tight. One is it’s never too early to go on an inner journey to start. Whether it’s learning to meditate or hiring professional help. I’m a strategic advisor to leaders and businesses. I’m a storyteller. I’m not a therapist. Surround yourself with the right professional help or healers or mediums, surround yourself with two or three people that you admire, see the best in you, and you can confide in those who are friends. Not going to take you into pity city and create some habits around wellness. Whether it’s yoga, Pilates or meditation.
Creating some of those habits in your life that help you calm your nervous system and tune into yourself is step one and you can never start too early. The second point is it takes time. Since the complexity of my journey was at least a decade long. I said back in 2020, “If you put a performance expectation on your inner journey, you’re going to just exacerbate what already exists in your life. Don’t do that.” Start now and build the community, build the professional support, and build the practices. Be kind to yourself.
Be kind to yourself that it’s a journey. It’s part of your lifetime. It’s not something that you deal with overnight. The third thing that I would say. At Sincerely, I am launching my own show. I’m the host of a global podcast called the Sincerely Show and everyone that I’m interviewing is living a life of service or contribution. They’re all doing interesting things for their local community, for humanity and for our planet.
Every one of them has been through an awakening of sorts. Every one of them has been through deep darkness. It’s mind-blowing that as humans, so many of us have to go through deep mental health challenges and what I call collapses of our ego, our fabricated identity in order to awaken into something that is more whole and more complete in order to feel spared and to dedicate your life to contribution, to service to humanity and to our planet.
The Life Of Service
The reason I share that as a common arc of the people that I’m meeting and interviewing is it’s a metaphor. It is Joseph Campbell’s Heroes Journey, but it is a metaphor for the human journey. An inner journey can be hard. It can involve collapses. Sometimes, it involves divorce or other forms of upset. It doesn’t need to be about affirming your gender. It can be heavy. The sooner we build mental health practices and wellness practices and the sooner we learn to love and live in a line with that inner child, the less harsh that upset is going to be because they can be hard. They can be heavy. That would be my advice for people. Those would be my lessons I would share with people.
Overall, you are saying that if you have conviction, that this is about who you are and what you believe in. Going through whatever upheaval that it causes will be easier. I use that word with a lot of trepidation that it will at least be easier for you to feel that you are doing what was necessary and right for you. If you don’t necessarily build that conviction, I’m sure it’s much harder.
In every human being, again, it depends how spiritual you are. Love is real. I know it in the core of my being. Human beings’ innate ability from our essence or our soul outward is love. It’s innate. Fear is the opposite. It’s a conditioned human trait. We needed fear, survival instincts to put food on the table and to defend against the saber-toothed tiger. Yet the extractive and performative world has fed off of anxiety and fear of being good enough to perform to appoint that it’s dominated our life. It’s almost become fabricated and embedded within the human psyche to a point that we’ve lost the ability to create commoner life and space in our life to be coherent to realign.
I’m saying this from the standpoint of your word conviction. Anybody reading that is on a journey to be a better manager or better leader is because something in you knows that you’re not operating from a place of balance or from a place of wholeness. Somewhere in you, you want to be loved just as much as your employees want to be loved or cared for or nurtured. That’s the right place for conviction to come from. Conviction from ego will be met with some form of a human breakdown or collapse.
Conviction from this place of a deeper calling that you want a world that is more inclusive. You want a world that is kinder. You want a world where we live harmoniously with self, each other and nature. You believe deep within you, to your point about conviction. It’s worth going on that journey, because if not us, then it’s going to be up to our children or the next generation. If that’s where the conviction comes from, which is what you meant, then I say yes. That is the right conviction because it’s from a place of service. It’s from a place of wanting to leave the sandbox better than it was when we took it over.
You’ve left us with a lot to think about. I sincerely appreciate your candor, your authenticity and what you are now turning to do in service with Sincerely. Thank you.
Thank you for the invite. Thank you for what you’re doing because it matters. We’re human beings and there’s an opportunity to be the most full and authentic version of human beings possible. That’s what you’re pursuing and I applaud you for it.
Thank you.
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What would I like you to take away from the discussion with Katherine? Probably, most importantly, is its success and alignment aren’t necessarily the same thing. One of the most powerful ideas from everything that Katherine said and there was so much there is that success often coexists with internal misalignment. She reached a point in her life prompted by depression and suicidal thoughts were she realized that she needed to reveal who she was to the world.
She did it in a very brave fashion through thousands of employees across the company that she was working for at the time. She heard back from people things that they’d never revealed to anybody else. People were willing to share with her in a very vulnerable way because she was vulnerable with them. It begs the question of, how many people are out there living lives that weren’t the lives that they’d intended? Living identities that aren’t who they are, or who they want to be. That, to me, is one very powerful idea from the episode.
The second thing is this idea of how leadership can be very different than the way we often perceive it. Katherine, by virtue of now living a woman’s life, had to adopt what she felt like was a more feminine way of leading. In doing so, she realized that command and control fear-based approach, not that she necessarily would have had that in the past. That approach was even more different from what she wanted to be than perhaps it had been in the past. She started to lead more through compassion and that’s been a revelation for her as you heard her describe.
Again, it raises a question of, can we bring more of this into our leadership approach in a way that will be better for our employees and a way that will help them connect to themselves and to us as leaders and to the organizations that we represent without sacrificing performance? As she said, these things are not necessarily at odds with each other. Finally, just as this idea about the extractive performative world that we live in, and the notion that we should slow down live more as we were meant to be, live a more regenerative life, both for our own mental health, but also for the broader collective health of the human population and the planet that we live on.
This ultimately is playing a big role in what Katherine is now doing withSincerely. As she says, living a life of service at that point and trying to deliver this message again and again. There is a different way of thinking about the way that we act, the way that we lead, the way that we interact with each other and the way that we live on our planet. I hope you all took away some other lessons from the conversation. I invite you as always to subscribe to Career Sessions onApple Podcasts,Spotify andYouTube. If you found this discussion enlightening, sign up for my membership community,PathWise and subscribe to our newsletter PathWisdom. Thanks.
Katherine Dudtschak is a former banking CEO turned conscious leadership advisor and creator of the Sincerely framework. After more than 30 years in senior executive leadership, including serving as President and CEO of HomeEquity Bank and Executive Vice President for Personal and Commercial Banking at RBC, she now helps leaders move from survival‑based identity to authentic, essence‑led leadership.
Katherine is widely respected for bridging elite corporate performance with deep human integration. She publicly came out as a woman in front of 80,000 people while still in executive leadership, marking the beginning of a new chapter focused on psychological safety, identity integration, and sustainable leadership from within.
Her work supports executives, founders, and high‑performing leaders who have mastered the external game of success but seek wholeness, clarity, and purpose.
Why Experience Is Becoming Your Biggest Career Advantage, With Dan Pontefract
July 13, 2026
Everyone talks about AI as the future of work. But what if the bigger story is something we’re overlooking?
In this episode, JR speaks with leadership strategist and author Dan Pontefract about why experience—not youth—may become one of the most valuable assets in tomorrow’s workplace. As workforces age and labor shortages grow, Dan argues that organizations must rethink how they hire, develop, and retain talent—or risk losing decades of knowledge and expertise.
In this episode, you’ll learn:
Why demographic change may have a bigger impact on work than AI
What “age debt” is—and why organizations aren’t prepared for it
How ageism affects professionals at every stage of their careers
Why traditional generational labels may be doing more harm than good
Dan’s “Rivers, Rocks, and Rubies” framework for understanding career growth
How organizations can turn experience into a competitive advantage instead of treating it as a cost
What professionals can do to build careers that remain relevant and rewarding for decades
Whether you’re just starting your career, leading a team, or thinking about what’s next in your 50s, 60s, and beyond, this conversation will challenge many of the assumptions we’ve long held about work, careers, and retirement. You’ll come away with a new perspective on why experience may be one of the greatest advantages you can build—and why the organizations that recognize its value will be the ones best positioned to succeed in the years ahead.
Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/dan-pontefract/.
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Watch the episode here
Listen to the podcast here
Why Experience Is Becoming Your Biggest Career Advantage, With Dan Pontefract
The world of work has a demographic problem, but most organizations and their leaders are pretending it doesn’t exist. We are living longer and working longer. Yet, somehow, we are still building and running organizations that behave like careers, ending at 65 with a cliff where you just stop working fully one day. We’re practicing subtle and, frankly, not so subtle ageism for anybody in their 50s. In the meantime, we’re seeing experience walk out the door. There aren’t enough younger workers to fully fill the gaps. The people in the middle are being stretched thinner and thinner.
We talked endlessly about the future of work, particularly related to topics like AI, flexibility and culture but we’re missing one of the biggest shifts that’s happening out there. It’s hiding in plain sight. The workforce is getting older. It is also getting more complex. What if the future of work isn’t young or disruptive but grey? Our guestDan Pontefract is making a point that we’re facing something he calls the age debt. A slow-building crisis that organizations aren’t prepared for but he also sees an opportunity.
What if experience isn’t a liability to manage but an advantage to unlock? In his new book,The Future of Work Is Grey, he challenges everything we think we know about generations, career journeys and what it takes to build organizations that work for everyone and for the long run. I’m JR. Lowry. This is Career Sessions.
I appreciate that. Congrats on your new book,The Future of Work Is Grey. Let’s get into it. You talk about something you described is the age debt. What’s the simplest way to explain that to the uninitiated?
It’s like a head in the sand of four key things, demographic change, ageism and inability to see and how to capture wisdom. The fact that we’re living longer, but no one is prepared for it.
You hit at this point that we’re living in the world of the past where people retired at 65. It was a hard cut off. You went from working full-time one day to trying to figure out what to do with your life the next day. That’s not how we’ll want it so much anymore but most organizations and their leaders are still operating in that world. Why is that?
It’s a cracking of the code I was trying to do within the book and I still don’t have an answer, quite frankly. I’ll say two things. First of all, there is an antiquated way of thinking that has just leached itself onto the point like, what is the definition of retirement? It happens in Japan at 60. It happens in Germany at 62 and North America at 65. That’s how we’ve always done it. The organizational and societal norms are that, and that’s a problem I would say.
The second thing is individual. We continue to think, “There’s this golden watch date. I’m 65 or whatever the date is, and then I’m going to be free.” I’m sure you see these stories. Lots of individuals a year or two years in are like, A) I’m bored out of my mind. B) I am lacking a sense of purpose for whatever is I want to do next because I’ve done enough golf and gardening to fill an entire Mars planet up with. C) They slowly look at the 401(k) or other savings. They’re like, “That’s going down faster than I thought or I didn’t save enough. What am I going to do now?”
I’m at that point in my life. I was working in corporate jobs up until 2025. I now run my own business. The question is, is that all I do or do I fill other things around it? I wasn’t ready to quit working and yet I was thrust into that model. I’m sure you found out by doing the research for your book and maybe personal experience, it gets a lot harder to find work when you get older. There is a lot of ageism out there. It just doesn’t feel like the world is geared for taking advantage of people who are like me. Not that this is about me, but people who want to keep working maybe less than full-time and maybe in a more flexible way but not just flip the switch completely off.
Your spot on JR. Whether you’ve been involuntarily removed from your role and/or organization at the same time. You’re like, “I didn’t expect that.” We, as individuals, and also, again, back to organizations are creating these constructs that are from the ‘60s or ‘70s. It’s still there now. That is, the only way to grow your career is to go up the career ladder. Even if you don’t go up the career ladder, you might get stuck halfway there, then you’re stuck. That day comes when you can no longer work for us and we’re going to get rid of you or you will retire yourself from the role you’ve had.
It’s just like, is that the only way? I blame tons of folks. I blame senior leaders in the C-suite who have collected enough of that money as retirement savings to not care. They’re like, “Whatever. This is never going to affect me. I don’t worry about the other 95% of the organization.” I blame HR, PNC or people in culture. Again, they have not paid attention and/or shove this under the rug and the carpet so to say about what is good culture these days.
Are they planning appropriately for the talent conundrum that they will face from the absolute demographic math that is going to math very soon in North America? There’s lots of blame to go around, but then thirdly the individual. When I’m doing my therapy and counseling sessions for those that reach out and say, “I’ve just been whacked by, name your tech company or name your organization. What should I do? I put 58 resumes and applications out. I’m not getting any callbacks.”
One of the other things we got to be thinking about as individuals is transferability and those skills that you have that you might have to lift and shift over to another industry, another role, or another type of job that you never thought of, but you’re smart. You’ve got scars, and you’ve got wrinkles from all these good experiences. You can transfer those to another type of opportunity that you might not be thinking about. There is blame to go around a lot of different ways.
What’s the biggest consequence of this that you’re seeing in organizations because of the fact that they’re not adapting?
Everyone’s love-hate relationship with Boeing is a pretty good real-life example. You’ve seen over the last 10-12 years, multiple incidents that are public. Let alone the ones that you don’t know about. One thing you can think about from a Boeing perspective, they’ve been public in Congress hearings about what has gone wrong. One of the issues is the fact that they both had voluntary and involuntary departures from a lot of these mechanic roles, operational roles, production roles, etc.
Not only did they lose wisdom that was chopped at the block. Again, either they chose to leave or they didn’t. They’ve had to backfill and figure out where’s the wisdom and how we train new people into these roles. Things are getting missed and things are lost. Things weren’t recorded, so we didn’t have any transfer of that wisdom let alone the capture. There’s one company of a kazillion where we could go into and say, “There might be real-life consequences or real business economic consequences if we are not thinking about talent in different ways. What could Boeing do?”
I’ll give an example with BMW, who’s doing it much better. The same thing. They make cars but they don’t make plans. It’s the same but different. BMW in Germany took a look at their aging workforce and said, “We got a lot of folks over the age of 50. Not a lot of young folks coming up.” In fact, Germany has one of the lowest birth rates in all of Europe. They’re like, “We don’t have a lot of immigration happening. What are we going to do?”
They start a program called the Senior Expert Program. The Senior Expert Program is a way for them to build up the skills of the middle aged leaders and individual contributors so that they know they’re going to move up into these new leadership roles. The people who are in the existing roles, who might be older or what I call Rubies. They’re offered the opportunity to stay full-time or on contract or part-time or whatever they wish to still be at BMW well into their later life. That’s a conscious decision of a C-suite saying, “How can we take care of our organizational talent and repurpose it in different ways?”
I’m sure there are lots of examples of companies that are starting to wake up to the fact that in most of the developed world, more people are aging out of the workforce than are coming into the workforce. It got this whole immigration debate that’s going on in many places. Without immigration, the math is the math. More people are leaving than coming in. It’s going to create, at some point, a labor shortage. Maybe that’s what people want. At the same time, we’ve got all this AI stuff going on and people are saying, “We don’t need as many workers as we used to have.” Maybe the math will end up working out for them but it’s a big gamble.
When it comes to artificial intelligence, to me, it’s too early to tell and it’s a bit of a red herring because tech was over-hired during COVID and post-COVID. Now, they’re just trimming the books and that’s getting all the mainstream media headlines. If you look at the actual data that says, “Is AI doing anything to replace young middle aged or older workers?” It’s nowhere near that. It’s, in fact, complementary rather than replacement. That being said, there are actual examples whereby organizations are not hiring young people.
My book is for all ages. When young people aren’t being offered those out of school internships or first time roles. They’re off doing jobs where they’re overqualified for indeed. Those organizations that aren’t doing the hiring and they’re preventing that friction learning from happening. That young people need to get in order to become more senior experienced people down the road. That, I would suggest leaders need to take a good hard look at from that perspective.
Now, flip it to the other end, to your earlier point. When we make rash decisions about workforce dynamics or talent composition, and then we’re just looking at EBITDA and saying, “JR and Dan, you two are making $200,000 a year. That’s $400,000. We’re going to get rid of you two and we’re going to replace it with a $70,000 individual. Two for one, we’re going to save $330,000.” Now, could you possibly maybe work with JR and Dan in a way that is, first of all, humane but looking at that talent composition as, “Maybe you could get two for one. Those two maybe want to work 50% each for like 3 or 4 or 5 years.”
The $200,000 each is $100,000 or even less. You’re just looking at the economics of your cost and P&L essentially differently so that you don’t lose immediately in 100% all that wisdom and the tacit knowledge that’s basically walking out the door. Both ends of the spectrum, you can see organizations not planning for that demographic inevitability. With immigration cuts, in both Canada and the US from North America perspective, it is inevitable that the over 50 crowd is increasing at a rate faster than the under 30 crowd. For those organizations not thinking about the longer term, you are going to be in for a world of hurt.
How much of the study do you think is exacerbated by the fact that you’ve got this incredible financial pressure that most companies feel to drive better returns, have consistently improving quarterly results and squeeze as much out as they can? Whether for the shareholders or senior management or both. Pushing that experience out the door because it is viewed as expensive and maybe not as productive as they would like it to be.
We were chatting and I was mentioning how this is rightly or wrongly, my 6th book across the library of Dan Pontefract books. Many years ago, my second book was published. It was called The Purpose Effect. In that book, I basically speak to three types of purpose such as personal purpose, role purpose and organizational purpose. Do you have a sense of purpose in your role at work? Now, why do I bring that up? It’s because it’s been ten years since that book. In the organizational purposes thesis that I suggested, organizations who continue to align with Milton Friedman’s shareholder primacy theory, which is essentially at all costs serve the market or the profit seekers for the quarter, which is AKA known as short-termism.
You will rue the day downstream if you’re thinking so short sighted in this with short-termism not thinking about the better health of your org over time. We’ve seen examples of this in the last decade where organizations who are myopic and just thinking in the short term have either fallen off the cliff from a fleet street or Fortune 500 perspective or they’ve had to do remedial efforts of trying to save where their economic value and output is. They might not be as innovative.
Examples could be things like research, motion and blackberry. There’s one perfect example whereby they weren’t thinking it through and then what happened? Everything was for the short term and the company almost went belly up. Now, my point is, you take that short term as I’m thinking and layer on the demographic inevitability that your workforce is shifting from a bell-shaped demography to a light bulb shape demography.
There’s less people in the bottom and way more up at the top. What are you going to do? Are you going to work for the short term or are you going to think about the health and longevity of that organization for which you work and say, “Maybe we should be doing things differently? Maybe we should do it for the long-term.” The two ten years apart are related but in different ways.
You mentioned Rubies a minute ago, Dan. I know you’ve got a different framework for thinking about the generations than the traditional ones of Millennials, Gen Z and Gen X. Talk a little bit about rivers and rocks and rubies.
What has happened forever basically, since maybe 1964, is that we have coined individuals in the organization and outside of it by these 14 to 18 year segments. To your point, Boomers, Gen X, Gen Y/Millennials, Gen Z and now Gen Alphas. How is that helpful, first of all, inside an organization who’s trying to be innovative, serve customers, and create a great employee experience? What it basically does is it takes societies tropes and means and places them inside the organization. It just compounds ageism
Whether that is ageism or directed at young people, or middle-aged sandwich workers, as I call them, who have to take care of ailing or dementia-based parents and the young kids at their raising. Maybe older workers who are just dealing with the fact that they’re getting older but still at work. Generations enforce ageism. If we were to just take a look at this and say, “You and I are both props of the same vintage.” Everyone will go through three career eras. As opposed to generations, all of us, regardless of your age and when you were born, go through three eras. I called them rivers, rocks, and rubies.
I’m paying homage to basically some early work with a psychologist, LaMotte. Basically, we have two types of intelligence. We have what’s called fluid and crystallized intelligence. Fluid is when you start and then that fluidity eventually morphs into crystallized intelligence. I was like, “Not quite.” That’s not what I see in my role as a people in culture executive for 30 years. I’ve seen three eras or three types of intelligence. Essentially, fluid intelligence or what I call the rivers, that’s when you’re just getting going.
Again, you could be 16 to 30 or 16 or 34. It doesn’t matter. The number doesn’t matter. You’re in your young era, but then you start to figure out things. In that same river, you start dropping what I call rocks. You solidify a little bit. Your river is still flowing around you. You’re still fluid, but you have now ideas on how and what works right in the right way because you get context. You develop that and more wisdom. As the river continues to undulate around your rocks, those rocks get polished and they crystallize over time to become rubies.
You, I, all of us, start as a river, become a rock and then eventually become this ruby. Again, you don’t have to use the vernacular but if you were to just say, “All our organizations and all our team members, regardless of whether they’re born in 1946 or 2026, it doesn’t matter. There’s these three eras and it happens. How might we look at intergenerational teams made up of rivers, rocks and rubies? How might we look at rivers as ways in which we help them become rocks? How may we look at the rubies and say, “The rubies are shining. We should keep a bunch of those shiny objects around so that we can help rocks and rivers become better employees.” That’s the type of frame I’d love to see.
What’s interesting about the whole generational labeling and stereotyping is, it’s fun but it’s also rife with accuracy. You are highlighting a lot of times. Somebody our age, we would have been rivers back in the day, trying to figure out what we wanted to do. Meandering through and ultimately figuring out a path that felt right for us, betting down and becoming one of those rocks. We look at those kids, they’re kids because they’re even younger than my kids are at the point, in their early twenties and think, “They’re different from the way that we were.”
They’re clearly different in the sense that they’re digital natives and we weren’t. There are definitely some things that will affect their adult lives relative to what has affected our adult lives. We blend so much of this stuff. The context of what’s going on in the world while you are coming of age. What is relevant to you in your twenties relative to what’s relevant to you in your 30s or 40s or 50s or 60s. The fact that they are somewhat different from what you and I were like when we were in our early twenties.
The problem is, when you start unpacking all of that, these differences aren’t nearly as big as we make them out to be. They become an excuse, a label, and a stereotype. They get in the way of people figuring out what’s the best way to work with everybody as individuals. To me, that’s the part about the generational labels that’s just flawed.
My dad was born in England during just the end of World War II. He grew up in an era whereby he put to work at sixteen. He was in an apprenticeship program. He was an Engineer, but they never had TV. They couldn’t afford a TV. Their entertainment was out and about in the community in England where he lived, but the radio. His stories at work were about radios. When he enters his rock era with other rivers who now are in technicolor, can have TV and its color. Now, these conversations are happening like, “Interesting. I never thought about TV that way.”
My point is, wherever you are, we all have tool change. Whether it’s from the radio, to the TV, to the internet, to AI. These tools change. Why is it that we can’t evolve our thinking to say, “Even though I might be a ruby, can I learn AI?” Of course. This is not the point. Can a river learn about the Beatles and the Stones now? Sure. I think they can.
You can go pick up some catalog of music and say, “That’s pretty cool music from the ‘60s and ‘70s. That’s the thing. We myopically consider and classify people based on an era where they were born. In my case, between `years of 1964 and 1980 being Gen X. Does that mean that I am not able to enjoy Wet Leg, Will Fallas or Wolf Parade or Harry Styles these days because of their river bands? No. The same thing can apply at work and that’s what I’m trying to get.
You talk about the title of the book, The Future of Work Is Grey, and there’s an implicit focus on the aging population and what’s happening with them. There’s a lot of ageism of mid-level people, middle managers, and others who are in their 30s and 40s. It feels like they’re under attack. We’re trying to thin out management layers and get rid of management numbers in a more general sense. The people who are left end up with 10 or 12 or 15 people reporting to them, who they can give no time to. What do you see happening with that population?
They’re the highest, on a percentage basis, increase in stress and anxiety as a cohort inside of our organizations. In the rock era, some of them are dealing with aging parents and young kids or kids, giving the birth rate to collapse. Nonetheless, having to do it to your point expands in layer increase. Not only is there the hollowing out of middle management. It’s like putting more on them. You’d have 8 to 12 direct reports in this span and layers thing. They’re being over six layers between the CEO and that frontline team member.
These days, the minimum it seems is that team size starts at 16 and then goes up to 50. To your credit, how are you supposed to have great coaching conversations, performance management, just normal development and being a leader and a manager at same time with a team of 50? These are consequential decisions that are being made. That is adding stress and anxiety on this middle cohort. What happens? Not only do you have that stress and anxiety going up. Performance issues will ensue, and then they start looking for other roles.
It’s like, “Can I possibly work for our company or organization that is pro midlife knowing that I am this sandwich generation leader and all these things going on?” What happens is you start having a talent exodus. That is another thing that could be thought through when you look at these three river, rock and ruby eras and say, “If we hollow out our rocks, who’s going to become our rubies one day?” It’s some short-sighted thinking there.
Have you worked with an organization and gotten them thinking in this rivers, rocks, and rubies construct? If so, what changes you see them making to make it better?
No organization specifically yet, because I’ve been immersed in the development of the body of work. In the research and the interviewing and then the working with organizations on pieces to the puzzle I was trying to put together, there are lots of good lights of hope around the world. An example are companies like L’Oreal and British Columbia Lottery Corps, in my home province in Canada here in BC. They have instituted phase retirement programs. Instead of you ducking out off a cliff at the age of 65, they ask you if you like to phase that out over 3, 4 or 5 years and maybe go from 100% to 80% to 60% to 50% time.
We’d love that. We’d love to support you. We get to use you still for that period of time over those 3, 4, and 5 years. How fantastic is that? We’d love to keep you around, learn from you and help you onboard your replacement or whatever the case may be. Those types of programs are pretty good. Unilever has another program, which is neat. It’s called Uwork. What they do is they allow you, whether you’re a river, rock or ruby.
They’re thinking about the longer-term play for their talent composition. Your work allows you to basically have a side hustle. As long as you’re not in competition with Unilever, you can start your own gig. You can work for another gig up to a percentage basis or a number of hours per week and as long as you’re doing your job. As long as you fit that in somehow, they promote it. You will have these new learnings and new opportunities then potentially also bring back into Unilever. There’s lots of good examples. It’s just that there’s no big, massive one, “We’ve become pro age and we’re going to do everything as I’m recommending.”
One of your other terms is experience dividend. What does that mean? What does it look like in a real company?
First of all, the book I wrote is like an album, side A and side B. Side A is the problem. Those are the problem tracks. That’s the age debt. If you flip the album over or get to side B on the book, the experience dividend, essentially. You can turn debt into a dividend if you erase your thinking, at least evolve it. The three good examples that are nucleus points, I call them as follows. One is the longevity lens. The second is the wisdom wheel. The third is the career canvas.
When I’m asking the leader to consider, whether you’re a small, medium-sized business, or you’re a unit leader or maybe you’re a big company or public sector. It doesn’t matter. The longevity lands are basically you say, “How are we going to be more age inclusive in our culture?” It’s our job descriptions. The fact that people are living longer and having open conversations about that. The fact that those rocks and some ruby women, 52% of them suffer from perimenopause, premenopausal and menopause. What are we doing about that and so on?
It’s just like these longevity items that we never talked about. If we were to become more age inclusive and pro age, maybe we should. That’s number one. Number two, on the wisdom wheel. Going back in time a little bit and saying, “Might we allow apprenticeships? How can someone shadow someone?” We learned from them. How do we make sure we don’t terminate rubies by not capturing their wisdom, and then sharing that?
There’s a great example of AI. Why not have a whole bunch of cameras or contraptions? Whereby, we are capturing the knowledge of people. Using AI not only to capture, but then to put that into nuggets of learning so people could learn from customer relationships that people have but never talked about. How you run the line and that production line and again, share that. Wisdom, mentoring, coaching, rotations, etc.
The career canvas is my point of taking a very large match in setting the career ladder on fire. This is where small, medium-sized businesses do this because they’re told to by edict, I suppose, from past lore. Large organizations still do this. The only way is up. A terrible song, but that’s not the way our career should go either. They should be multifaceted, multidirectional. What’s wrong with a 48 year old taking a two-year down spin and saying, “I don’t want to be the Director for a while. I’m going to be an individual contributor. Is that cool?” Why not?
Is there a stigma? We call it demotion? Why do we call it demotion? That’s terrible. You’re just taking a break but you’re still a full-time employee. You just don’t want to run a team anymore. That organization shouldn’t lose you if you want to do something different for a while. That’s what I’m getting at. The canvas is, you and the team or the organization, rethinking about every career goes up. In fact, it could be multidirectional and like a good painter, you have all these paint colors and brushes. How might we basically paint a better picture using the canvas of opportunity?
So much of this just strikes me as you’re talking about this, Dan. HR people and cultural organizations are so pressed for time. They’re besieged. They’re getting pressured to halo themselves out and use AI across everything. They don’t have time to think about this. An enlightened manager, if somebody 48 years old came to them and said, “I want to downshift for a couple of years because I’ve got something going on and my personal life and I’d like to go back to doing what I was doing.”
An enlightened manager, an enlightened HR person, an enlightened organization, you put all those things together, and that might happen. The odds of each of those things being in place, is certainly well less than 100%. Multiply them all together and you get something probably approaching zero. That’s why this doesn’t happen so much. It’s because it requires work and it’s so antithetical to the way that people tend to think about the career ladder and the idea that if you step down, it’s permanent. You can’t come back to what you were doing.
I do love the word antithetical. This type of thinking is anathema to the longer term rethinking that any organization of any size needs to be doing. Again, if I were to chat with you in ten years time and we say, “In 2026, Dan, you said demographic disruption is an inevitability. The math math’s on this one. Ten years later, in 2036, how did those organizations do?” The good ones will be making the plans and preparations now to do exactly what you said to carve out time in calendars to say, “What will this organization be like in 5 years or 10 years?” If you’re not a leader who suggests to everyone, “We got to invest a little time on this,” then that conversation you and I will have ten years from now. We’ll be talking about a lot of broken organizations and people.
There’s so much disruption going on now. I haven’t felt this way since the internet era was blossoming many years ago in terms of what’s going on with AI. I feel like the broader geopolitical sense and how people are thinking about those forces and their careers. It feels like the next ten years are going to be interesting. It’s hard to know how any of its going to play out.
I don’t disagree. The only way I would disagree with it is that we’re running out of people. If we’re running the people, that tells me there’s a supply and demand scenario that is unfolding that we might want to pay attention to.
Apart from the fact that we’ve got the supply demand inequity that you’re talking about. You also make an argument that thinking about this more creatively helps with innovation. Not just filling seats but also with doing better work, driving work, innovation and growth. How so?
If I told you that in Japan, adult diapers outsell baby diapers. It might be a bit of a shock for those that haven’t heard that before and it’s true. South Korea is the same thing, by the way. The diaper manufacturers, when they started looking at the demographics, they’re like, “Maybe we should start thinking about what that consumer pool looks like. If it’s shifting demographically, maybe we should shift with the times.” There’s a hidden point in this book.
The book is called, The Future of Work Is Grey. Grey is meant to be a double entendre, which is that we are aging as society but also, there’s fog. Grey can mean fog. What I’m trying to do with the fog is to lift it and then when you lift that fog, what should there be is, hope for an opportunity. Which is why the cover is Gold. I think the future of work is a golden opportunity. Whether you’re looking at that from what consumer opportunities, what business opportunities, and what B2B opportunities are there as society ages. You’re like, “We can put our heads together here and maybe think about different ways in which to help.”
This isn’t just like, “We need more elder care homes and health care options.” We do, but that’s not the end of our innovation that we should be thinking about. If you get intergenerational, rivers, rocks and rubies, thinking creatively about what we might do economically from a production, innovation, output perspective. Maybe you come up with your own adult diaper strategy, and maybe there’s something else metaphorically there that helps you for the long term.
It’s hard to do a follow-up question when we’ve been talking about adult diapers and baby diapers, but I’m going to do my best. For an organization that’s thinking about this, somebody picks up your book, reads it and is thought-provoking to them. What do you want them to start doing, stop doing and continue doing?
It’s not in the right order in the book because I wrote it in a way that just said, “You can pick up any track whenever you want,” because I don’t even call them chapters. I do think that if I were to pin the tail on the proverbial age donkey, ageism is the one that is the immediate remedy opportunity and what’s happening. You see on one end, older rubies, even rocks scrubbing their tenure from LinkedIn. They’re embarrassed or finding that they’re not getting through to the recruiters or talent teams or even hiring managers. They might have worked for six years between 1995 and 2001. That’s dated on their LinkedIn.
There’s this, how old is your inferiority complex that has enveloped the Western world? As if we’re not supposed to say our age. As if I am looking into this camera, it isn’t 55. I’m supposed to be 38. That is ageism but that’s self-ageism. Meaning I am embarrassed by the inevitability that I am aging. We all age. That needs to be self-corrected but then, you’ve got the age against the machine, as I call it, issue. That’s the organization.
Whether that’s talent teams, hiring teams, or HR teams who use ATS and are consciously looking for age and to scrub those people out from the potentiality of being hired or getting to the interview stage. That’s wrong. That’s ageism. Ageism is how you craft your job descriptions. Ageism is how you craft who gets considered for promotion or the projects inside your organization.
Ageism is how you communicate in the town halls by recognizing only the rivers or vice versa, never recognizing the rivers. All of this has an opportunity. If we just looked in the mirror and said, “We all end up six feet under. Age is inevitable. What is it that we’re doing to be more inclusive rather than age negative and ageist?” I think that’s the opportunity.
If people start working well into their 60s or their 70s and maybe even into their 80s. What do you think’s going to change most about the way that the workplace works?
There’s going to be all some practical changes. Westpac is a bank in Australia who took a look at their workforce. They got 33,000 people or so. They recognize that just 22% of the workforce was over the age of 55. They’re like, “That’s like 7,000-ish people. Maybe we could do some ergonomic accommodations for whether they’re bank tellers or things that’s happening within their actual branches and so forth.” They made a conscious decision to be pro age, age inclusive and then look at things ergonomically.
When I was visiting a couple car manufacturer plants in Japan, they too have done the same thing on the lines. Both with the use of AI and VR headsets and the way in which the lines are crafted to be more pro age for potential physical labor work as these examples I’m giving you. It can be done in a way that’s a little bit more healthy. You got that, the physical, ergonomic, easy, low hanging fruit stuff.
Does anyone out there think that they’re training people to understand their unconscious and conscious bias of age? Do we have age training or ageism of training? Are we a pro age company by talking a good game and putting up posters of people of three different eras but not teaching people how and what they’re doing from a biased perspective and enlightening them? That, to me, is a conversation at a leadership level. Your line leader or you as a team lead could be having it and good on you if you are. It is a conscious culture change opportunity that the C-suite and the senior leaders need to be having.
You wrote this book because you saw a gap in the way that people were thinking about this. Having now gone down the rabbit hole of looking at this very deeply, where are you in terms of optimism, pessimism about where organizations are and what the future holds for us?
I’ve been an executive at Telus and SAP for about eighteen years, running culture, leadership development, all the CLO capacities and I never thought about age. Not once. If I consider myself semi-smart with a bunch of degrees, running culture change in the development of leaders and teams for two organizations over nearly two decades and I never once thought about it. I’m trying to perhaps remedy a little bit of my own past mistakes and to enlighten others that certainly I would argue aren’t thinking about it either.
Now that the book is out in the world, the conversation will blossom because people will be able to pick it up and start talking about it more. I appreciate you taking time, especially given that this is launch week talk with me. Thank you, Dan.
It’s been great to chat with you, JR. Thanks to the opportunity. I appreciate the new friendship.
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What I would like you to take away from the discussion with Dan, first is this idea that age is real. In most of the developed world, we have fewer people coming into the workforce than we do leaving the workforce. It’s going to compound just given what’s going on with population trends. The idea of age debt reflects this demographic change as something that organizations and leaders are ignoring. The cost is starting to show up in talent gaps, disengagement and lost knowledge. That’s what is providing the spark for Dan writing this book in the first place.
Second, we talked about generational labels and how we often use them as a crutch and not a strategy. This idea of rivers, rocks and rubies rather than Gen X, Y, and Z. The way we talk about this isn’t just semantic. We need to rethink how we design teams, careers, and leadership to reflect the fact that we have a multi-generational workforce and that we’ve got to create something which sustains itself over time and gets the best out of all those populations. Also, recognizes the life constraints that they’re operating in and what they need from their professional lives at that point in their lives.
Third is, this idea of the experience dividend. Flipping on its head the idea that experience is costly, older and unproductive workers. Start to think about how we get as much out of these people as possible and take advantage of them. Potentially, an alternate labor model from the traditional idea of a full-time person who steadily rises up the corporate ladder. This idea of getting more out of these people will be especially critical as we are relying more and more on experience. Especially when we’re hollowing out junior roles with AI.
Finally, it’s this idea that we’ve got to think differently about age in the workforce. The companies that are going to be successful, probably aren’t going to be the ones that are the youngest or the ones that are the most disruptive. They’re going to be the ones over the long term that integrate talent across ages, skills and perspectives.
That’s going to require redesigning careers, rethinking leadership and letting go of some outdated assumptions about how long and how linearly people work. I invite you to subscribe to Career Sessions onApple Podcasts,Spotify andYouTube and others. If you found this discussion enlightening and I hope you did, please sign up for my membership community, which is calledPathWise and subscribe to our newsletter PathWisdom. Thanks.
Dan Pontefract is a renowned leadership and culture strategist, author, and keynote speaker with over two decades of experience in senior executive roles at companies such as SAP, TELUS, and Business Objects. Since then, he has worked with organizations globally, including Salesforce, Amgen, State of Tennessee, Nestlé, Canada Post, Autodesk, BMO, Government of Canada, Manulife, Nutrien, UBC, McGill University, Virgin Media O2, City of Toronto, among others. Dan has firsthand experience in turning leaders and corporate cultures into a competitive advantage. Dan has written five books: WORK-LIFE BLOOM, LEAD. CARE. WIN., OPEN TO THINK, THE PURPOSE EFFECT, and FLAT ARMY garnering multiple awards including the Thinkers50 Top New Management Book and the Axiom Business Book Awards Gold Medal. Dan has also written for Forbes, Harvard Business Review, Leader to Leader, The Globe and Mail, Inc., among other outlets. Dan is a renowned keynote speaker who has presented at four TED events and delivered over 600 keynotes. He is an adjunct professor at the University of Victoria and has received over 25 personal awards. Dan’s career is interwoven with corporate and academic experience, coupled with an MBA, B.Ed, and multiple distinctions. Notably, Dan is listed on the Thinkers50 Radar, HR Weekly’s 100 Most Influential People in HR, PeopleHum’s Top 200 Thought Leaders to Follow, and Inc. Magazine’s Top 100 Leadership Speakers.
Why You’re Overwhelmed At Work (And How To Fix It), With Liane Davey
July 6, 2026
Why does work feel so overwhelming, even when you’re getting everything done?
In this episode, leadership expert and bestselling author Liane Davey explains why the problem isn’t your workload—it’s your thought load: the hidden combination of cognitive demands, emotional burden, and depleted energy that makes work feel harder than it should.
In this episode, you’ll learn:
Why working harder won’t solve the problem of overwhelm
The difference between workload and thought load
How constant context switching and emotional stress drain your performance
Why attention is your most valuable resource—not time
A practical framework for prioritizing what matters most
Simple strategies to reduce overwhelm, regain focus, and protect your energy
You’ll walk away with practical tools you can use immediately to feel less overwhelmed, improve your focus, and do your best work without burning yourself out.
Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/liane-davey
Buy Liane Davey’s new book, “Thoughtload”, subscribe to Career Sessions on Apple Podcasts, Spotify, or YouTube, and join the PathWise membership community today at pathwise.io.
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Listen to the podcast here
Why You’re Overwhelmed At Work ( How To Fix It), With Liane Davey
A lot of us are feeling overwhelmed in our professional lives and a lot of times, we blame our workload for that. Too many meetings, too much email, and all the administrative work. The priorities that are constantly changing with unrealistic deadlines. What if workload isn’t the problem? What if the real issue is in how much work you have but everything that comes with it? The constant context switching is like multitasking. The emotional labor of managing up and down and sideways. The mental tabs that are probably still open as you’re trying to fall asleep at night.
If you’re a manager, the pressure of knowing that you’re accountable for your team success, but also knowing that you’re barely keeping your own head above water. Our guestLiane Davey argues that we’ve been diagnosing this all wrong. That it’s not about workload, but about something she calls thought load. The hidden combination of cognitive demands, emotional burden, and depleted energy. That’s the real killer performance.
If she is right, then working harder isn’t the solution. Working differently is. Liane is a New York Times bestselling author, leadership, advisor and someone who has spent decades inside teams trying to figure out why smart capable people so often feel stuck and burned out and ineffective. In her new book,Thoughtload, she offers a different lens in a very practical playbook for escaping the madness. We’re going to be challenging some deeply held assumptions about productivity and leadership and what it takes to do great work. I’m J.R. Lowry. This is Career Sessions.
I’m so glad to be here, J.R. I’m looking forward to our conversation.
It’s nice to speak with a fellow page to offer. Your book is coming out in a few weeks. It’s calledThoughtload. Let’s get right into it. You make a key argument in the book that what’s over all of us isn’t our workload, but it is our thoughts. Explain the difference for us.
Workload is the effort that you put into producing outputs that are the key piece of your job. I sent the report. I got the signed contract or whatever. Thought load is much bigger than that. It’s everything other than the actual works. I call it an invisible tax on our performance. It comes from rising cognitive demands. Everything we have to pay attention to, so the work and everything else. Increasing emotional burdens because we’re living in an emotionally dysregulated society.
There’s a lot of emotional residues sitting on us and how we’re trying to do all of that with declining energy reserves. Workload is what you have to accomplish for your job. Thought load is what you have to cope with as not only an employee, but a human and all you carry with you. The problem is, the higher your thought load the harder it is to get through your workload.
It makes intuitive sense once you explain it that way. As I was reading the book, I was thinking about my most recent full-time experience. The workload was always high, but it became impossible, when you’re getting assaulted from all sides. Assaulted from vendors and employees. Not in a physical sense, to be clear. Assaulted from above, board, boss, all of those things.
When all of that is hitting here, it’s a lot harder to maintain that emotional regulation and the multiplier effect if you want to think about it in the way of thought load being a multiplier on workload. It goes from being like 1X to being like 10X. It makes it almost impossible to keep up with things because you’re never at your best and you’re constantly having to play defense on one of those things and the work is still there.
Exactly. You finally carve out an hour to make some meaningful progress, but the thought load is so high that you get distracted as you’re going or the emotional stuff is making you feel like, “Am I even up to doing this?” All of that means that hour doesn’t get you as much forward momentum as you hoped it would. You spend the next hour feeling crappy about the fact that you just wasted the last hour. It is a multiplier effect in a negative direction.
What was the moment where you had the a-ha about the idea of thought load?
There were two key spots. Before COVID, people kept asking me as a keynote speaker to talk about change management and I had this reaction. As a psychologist, our reaction to change has been the same for Millennia. Anyone who’s trying to tell you differently doesn’t understand how the brain works. I thought it was a little dull until I started looking at, not how the human reaction to change is any different but how change has changed in organizations.
Gartner released a study that was probably the first moment that showed that, in 2016, the average employee faced two enterprise level transformations each year. Only six years later, it had gone from 2 to 10. That’s the moment when I had my first realization that change has changed. We need to manage differently in this perpetual change than we did in our simpler era. That’s when I started thinking about how we have to manage our attention, our anxiety, and our energy.
The core of the thought load equation came then, but it was in front of a live audience, giving a keynote. Somebody asked a question at the end and said, “Isn’t our workload way too high to do this?” Live from the stage, I just came out with, “It’s not our workload that’s killing us. It’s our thought load.” As soon as I created the word live in front of an audience, the room went silent. All I could do was go, “Could somebody write that down?”
You probably wanted to run off the stage and go make a bunch of notes on it.
Those two pieces. First, I had to have this realization that change has changed and we need to manage ourselves in one another differently in perpetual change. Secondly, realizing that we’ve been putting way too much attention on workload and what we have to think about is our thought load. Those were the two pennies I had to drop before I was often running.
I have done a lot of transformations in my day. You do realize as you do more of them that it’s not just managing people through change like, “I have to do something differently than I did it yesterday.” It’s more of the human part of getting through that. Even for the project team themselves. They’ll be completely committed to the end state but when these things go on for months and months or even multiple years. The adage of, it’s a marathon. Not a sprint. It’s a little bit trite but, at the same time, it’s true.
I was giving a talk at a conference over in London on this very topic of, how do you manage the human element of these big transformation programs? That’s arguably the hardest part. It’s not technology. It’s not the process of change. It’s just bringing people in the project team and around the project team for the duration of that journey and keeping them engaged especially to your point. It’s like, “This follows the last change or it’s going on in parallel with three other changes.” It’s constantly changing. It’s hitting us all the time. It’s hard for people to keep up with that. That’s a big factor that’s hitting at this idea of thought load as well.
That changes the team, it’s their primary role. Think of all the people who are on the receiving end of the transformation and the thought load equation is terrible. A) You’re asking me to do this off the corner of my desk with a tenth of my attention. B) You’re probably not creating a forum for me to process the emotions that are coming up for me about whether this change is going to make me redundant or change my control or whatever else. You’re expecting me to just do this change after the last change and burning me out. It’s one thing for the team that’s central and focused on the transformation. If you think about everybody on the receiving end, it’s even worse. We’re amplifying this thought load effect in our organizations at our peril.
I agree. We talked a little bit about the three things you talk about in the book, the cognitive demands, the emotional bird and the energy depletion. Why is it so important to think about all of them in combination and not individually?
There’s a lot of people out there talking about each of them separately, but nobody’s talking about all three together. The reason is, and this is partly my husband and my business partner who’s a neuroscientist who helps me understand. That each of the three components, both amplify and exacerbate the others. I’ll give you a couple of science-based examples. As your energy reserves run out, particularly your frontal lobe, which is your executive functioning. Which runs out fairly quickly, because it burns a lot of glucose and releases a lot of glutamate.
Your frontal lobe goes offline fairly quickly. When it does, one of the first things to go is your ability to calibrate what should I pay attention to and what should I not. All of a sudden, the cognitive demands go up as you’re paying attention to everything. The next thing to go is your ability to differentiate between something that’s a social threat and something that was a sarcastic remark or whatever. As your energy goes down, your emotional burden and your cognitive demands go up.
Another interesting one is one of the most common emotional burdens for us as anxiety. Particularly anxiety about our workload and how much we have to get done. What we find is that, as your anxiety rises, you try to multitask. You increase your cognitive demands. As you multitask, your energy depletes faster and your productivity and your quality suffers. You’re doing that in the wrong direction. The reason you need to understand and try to tackle all three is that, if you only solve two of them, particularly if you try to ignore the emotional things. Our brains are very wired for fear to just take out everything else.
You could be building the nicest time management plan whatever else. If something hijacks you, because you’ve decided it’s a risk to your belonging in the group or whatever else. It doesn’t matter how great your time management plan was. That’s why we need to think about them because physiologically, each one of them amplifies and exacerbates the other so we have to deal with them together.
It’s especially hard for managers or leaders because they’re not only having to worry about themselves. They also have to worry about this for their teams. How do you help managers figure out even where to start with this?
The answer for managers is start with yourself because managers with a very high thought load, leave a very big week behind them. If you are struggling to know what to pay attention to and trying to juggle many balls. Your team is going to be looking to you for prioritization and they’re not going to find it. They’re just going to be looking at somebody who’s like, “It’s all important.” If you are emotionally triggered in some way, impatient, frustrated, or feeling demoralized, the emotional contagion from a manager to their team is incredibly potent.
You’re going to leave them just feeling deflated as well. Start with yourself as the answer and in starting with yourself, I encourage folks to start with focusing their attention. It’s hard to deal with the emotional stuff or to get your energy back if you haven’t zoomed in on what matters first. Start with your attention, then learn some of the emotional literacy that we don’t have so that you can process your emotions more quickly, then you can work on the energy.
Certainly, you can dabble in them all but the first thing is your attention. Once you’ve created some order in the chaos in your own head, then you’ve got a hope of going out and supporting your team. If you are leaving a big week behind you, both terms of priorities and emotional residue. There’s little hope you’re going to help your team.
A lot of people think that time is the most precious resource. I’ve certainly said that to my team again and again, but you make the point that it’s your attention. Time is limited. Attention is even more limited, which is what makes it more precious. You’ve got some great tips to help people think about how to focus themselves on what matters. Share some of those for us just to give our audience some practical takeaways.
I love it when we talk about time as if somebody magically has more than 24 hours a day. No time is fixed. We all have the same amount of time. What do you think about both your attention and your energy at that time? That’s what I was alluding to earlier. If you have one hour and you have that one hour with a low thought load, with real clarity on the most important thing you need to accomplish. With everything ready to go when you start the hour, with the things that are weighing on you parked for a time when you address them.
In that hour, with both strong attention and good energy, you will move through so much. You’ll get so much accomplished. I had this. I thought I had a meeting at 9:00 AM but it turned out it was 10:00. I sit down at my desk. I get my microphone ready. I’m all good to go. I open my calendar and see that I have an hour. Interestingly, I wasn’t ready to have an hour then. I didn’t know what’s the most important thing. I’m in the middle of a book launch. There are a million things I should be doing.
I didn’t know. I didn’t have focus. It was in the morning. I hadn’t gotten moving yet. I made very little use of that hour that could have been really meaningful. It’s figuring out, how do I have a clear quest? What is it that I have to accomplish? How do I have mise en place? How do I have everything ready so that when I start to work, I don’t have to open my email to find something? If you open your email to find something, I promise you something else is going to distract you or if you have to go on the web and search for something or whatever else. How do I do that?
How do I go in with clarity and remove the distractions? It’s not having the hour. We can usually make the hour. It’s what we make of the hour so that we get something meaningfully done. If that happens at the end of the hour, then also, you get this emotional lift. It’s like, “That feels amazing. I shipped that code. I sent that contract. I did the thing.” The next hour is going to have benefits. I always talk about it. If we have to do something hard, start on a downhill. If you’ve just had that hour, the next task is going to feel like you’re starting to go downhill. I got momentum here. Let’s go. Follow that energy. Time is not the issue. When you have the time, the same 24 hours as I have, how do you use it?
I was a CEO of an asset management company. At one point, that is thousands of people working for me. It’s a big role and I say that not to brag about it, but just put it in stark contrast to the life I’m living. My days there were very busy but they were also very programmed. You knew how certain pockets of your time were going to be used a day in advance, a week in advance and sometimes even longer in advance.
What I’m finding out that I’m doing my own thing is I got to figure out what every day looks like. I have found it much harder to be focused and much harder to get good use out of my time because there’s a million different things that I could be doing. I’ve literally had to block like, “I’m going to spend 30 minutes on this task. I’m going to spend an hour on this task.” That’s the only way that I am finding that I am able to get through things and to do them while and to feel like I’m productive.
Otherwise, I get to the end of the day and feel like I got pulled in fifteen different directions and I didn’t get anything done. That’s something I never felt to the same degree even running a big organization in a corporate job. That’s been a real learning for me over the past roughly a year that I’ve been doing this and I’m still learning, to be honest with you, about how to focus my attention and get as much out of those hours as I can.
I love that you’re being authentic about that because I feel every bit of it. This is year eleven for me in my owning business and I got to a pretty good point on being productive. All of a sudden, I ran into this massive very painful realization that while I was being incredibly productive, it was not effective. I realize that while I was patting myself on the back for creating a lot of output, that output wasn’t moving the needle on the things that I cared about. That was excruciating. For many years, I had written a blog every single week and I was so proud of myself. I would look down on the people who started a blog or a podcast and only did it for like seven weeks or whatever. You’re like, “Those people.”
I was so proud of myself for just churning it out but at some point, I said in 2026, is what people are looking for advice about achieving amazing things together. Are they looking in the same places? Do they need the same content? The answer was no. I was so proud of how productive I was and not asking the hard questions about but is that productivity in service of the ways I want to change the world? That’s the other thing.
If we can make the transition from focusing on activity to output, that’s good. That’s an improvement. Responding to a lot of emails never changes the world. It’s good if we get out of that and even harder shift because our world is incredibly focused on productivity and just not nearly focused enough on, is that productivity serving anything? AI is the greatest example of that. AI makes it easy to create a lot of schlock.
It’s not going to change anything. The good news for an entrepreneur is that, at some point, you go, “If I am clear on my quest in the world, on the outcomes I’m trying to create, maybe there’s a bunch of stuff I don’t need to do. Maybe I could have a better life while running this business.” It’s very interesting but I had to make the epic fail before I figured that one out the hard way.
All having to let go of a lot of things in terms of the way that we’ve done them in the past and AI is striving for that. It’s probably the single biggest factor at the moment, but it’s not the only one. That’s hard. If you’re a content creator, that world has changed tremendously in the last five years. You talk about activities, outputs and outcomes. You have to continue to focus on outcomes. Ultimately, if you’re an entrepreneur, your job is to bring revenue in for yourself and your company if there are others around you. It doesn’t matter how many likes you get or how many impressions you get or how many followers you have. None of that stuff. It’s all helpful.
Even there are places where getting views are not the views that are helpful. It can be vanity.
There are vanity metrics. People talk about that a lot in the creator space, but they’re vanity metrics in the corporate world as well. It’s easy to get drawn into them like, “I cleared my inbox out or I went to five meetings or I put out three articles on the corporate internet site,” or whatever the case may be. If you keep yourself focused on the things that matter then it will help Focus your attention. You have another framework that I thought that was helpful, this idea of the three priority lists.
When you have a high thought load, having a to-do list is a nightmare. First of all, because every time you look at it, it’s demoralizing. Secondly, because when your thought load is high, you tend to pick what to do off that list using a terrible criterion. Maybe that criterion is, which of those tosses are associated with the scariest person or like, “What’s the one I just wrote down? What’s the thing that just came into my inbox? I’ll just do that one.”
When we have a high thought load, having just one long to-do list isn’t helpful. If we can understand that most of us operate on three to-do lists at least for work, the first one is, what are the things I need to do to advance my quest? The thing that I’m here to accomplish. What’s the number one? Number two, and number three things I could do that will significantly progress the things that matter most? We all need that list. If you work in an organization, there’s a second list because we don’t live in Pollyanna world.
The second list is other people’s very important quests that they think I need to be a part of. Maybe you’re an expert in the automotive industry and your firm’s automotive account team wants you to come and be part of the team. That may be important and there’s a wide variety for us in cross-functional organizations and matrix organizations where you need number 1, number 2, and number 3 to-do list for ways you support other people.
We all have the third list, which is the side quests. I got to do the compliance training. I got to send my invoices. I got to book my trip. If all of those things are on the same list, it’s easy to just look and pick off things for all the wrong reasons. If you start with, “I need to be making sure that the things from my number one list get slotted into the calendar first.” The things from that side quest list get put in the lower value part of my week, they get put in between tasks or when I’m on hold with the help desk or whatever else. Three party lists, not one, makes a world of difference.
You can’t compare one versus the other. The thing that’s important that your boss has asked you to get done may not be the most important thing toward your outcomes. You still have to do it or the thing that your kid wants you to get done with them that night when you get home for work or whatever. Managing things and thinking about both, the different lists and also how you use your time and marry your time up with that I thought was helpful.
It’s also a great thing to be able to take your list to your manager. If your manager asks you to do something, just share, “It’s Wednesday. I haven’t made any headway yet on the things on my most important list. Where does that thing you’re asking me to do fit in? How do you want me to prioritize that?” When you’re managing it that way and you look accountable and take ownership of your time. That’s a constructive conversation to have with your manager.
Let’s talk a little bit now about the emotional aspect, the second of the three. You describe it as an invisible load. You also talked about the fact that people in the middle of the organization are arguably dealing with even more conflict because they’ve got to below, across, up, and at home. What advice do you give people to help them think about their own emotional load? Also, this issue that you talked about in terms of emotional contagion where a manager can infect their team for lack of a better way of saying it.
Maybe be infected by their team and all managers have that day. What we’re missing is emotional literacy in our society. The starting place in the book is to talk about some of the neuroscience of how this works. Which is that, an emotion is a pre-conscious physiological experience we have in our body. There are a lot of data on emotions. There’s lots to learn from emotions. They’re there to keep us safe and help us be effective in our environment. They are very different from our feelings, which are the cognitive stories and narratives that we come up with to rationalize what we’re experiencing in our body.
Most of us don’t know that. Therefore, most of us believe our feelings as if they’re true. We give them too much credit. We take too much stock in them and while emotions can get us lots of data, feelings get us lots of drama. That’s the first thing we need to understand. First of all, there’s no such thing as turning off your emotions at work because they are pre-conscious but the key thing is to interrupt that fiction weaving process of telling yourself this grand story why they made you upset and all these things that make us feel not in control of our own emotional experience of the world.
First of all, understanding that and learning a process to intercept the emotional experience. Learn from it. Interrogate it before it turns into some great fiction. That’s the first piece. Once we understand that’s what’s going on, to be more attuned to it going on in the people around us, so that if they’re having an emotional experience, we don’t unintentionally or unknowingly pick it up. That’s what happens in emotional contagion. You can feel the whole room go down. One person is feeling deflated and all of a sudden, you feel the whole room go down.
The book takes you through a process for, how do I notice the emotion? How do I extract the data from that emotion? What is that about? Where is it coming from? What is it exactly? What story am I telling myself that is reinforcing how I’m feeling about this and then to get to some action to make things better. Teaching people how to process their emotions more efficiently and then what to do if you’re seeing that from somebody else and how to prevent that from spreading to you.
Learning that emotional literacy of the difference between emotions and feelings and then learning how to process our emotions more quickly so that they don’t take us down or leave an emotional residue for the day or the week. That’s just sitting in our thought load. You bought real estate in our thought load. I’m just squatting here and I’m not leaving.
I love the story in the book where you were describing the snow storm and being mad at your husband for taking one of your shoveling turns because you thought that it meant he thought you were weak. He was just trying to be nice. You describe this as an example of the fiction that we tell ourselves about why something’s happening when it’s not true. One of the things I took away from that part of the book because the idea of pulling the thread. You talk about knowing your treasure. It would be great if you could help our audience understand this idea of how you get to the why that you’re feeling that thing and sometimes how it’s a multi-step approach.
As I was writing the book, I was trying to make the book what I described as buoyant. How do I make this something that for somebody who has a heavy thought load that it’s enjoyable to read. It feels like something that lifts you up or helps you get your head above water.
Enter self-deprecation.
There’s a lot to share with you about all my failures. We started with the night on its epic quest. When we got to the emotional section, I shared a story I’ve used for a long time, which is when the dragon is breathing fire, it’s because they’re protecting treasure. If you, on your noble quest, bump into a fire breathing dragon, do not do what we tend to do, which is build a wall of facts between us and the dragon. You’ll recall the email of April 2nd that said this and this or in policy 17.3 point range. That does not help when a dragon is protecting their treasure. All it does is build this wall. The dragon is still back there.
The idea is that the fire from the dragon is the emotion. They’re angry, yelling, crying or whatever it is. If that’s what you see, that’s not the important point. That’s just a good clue that, “Somehow I’m encroaching on their treasure. They feel a threat. They’re triggered and that’s what I’m seeing.” The key thing is, I talk about it as they’re on the other side of the moat trying to protect themselves and their treasure. You need to get them to open the drawbridge. What can you ask? What can you try and understand? What’s at stake for you here? How do you imagine this playing out? What mistake do you think we’re making?
These kinds of questions that get the dragons open the drawbridge and draw you the map to what the treasure is in this situation. What is it that they value? What’s precious to them that feels under threat with this conversation or this plan? Once we understand the fire breathing dragon metaphor, at some point, you stop and you go like, “Sometimes, I’m the dragon.” When we have that emotional reaction, something feels at risk and that’s how we protect ourselves. You can ask yourself the open drawbridge questions. What story am I telling myself that’s causing me to react this way? How am I seeing this playing out?
You can then ask other questions, like what else might be possible? What else could be going on here? As you come up with answers, share those answers with the room, “The reason that I just raised my voice there is, I’m imagining having to go back to my team and tell them that I wasn’t successful in advocating for our project. I’m feeling like that reflects poorly on me as a leader. They’re going to be upset with me.” Being candid in the room about what’s going on for you. Not in a way that’s like, “I’m so angry.” You’re not like losing your cool, but you’re doing the investigative work to figure out what’s the treasure going on, open the drawbridge and share with everybody else what’s going on.
It just creates a much more constructive conversation. I tell the story in the book of a real team, where they were trying to figure out which projects to cut because they needed to do a big budget cut. The leader was not engaging in the conversation very honestly or with integrity. He was trying to defend his thing and it was because this is what he was imagining. Having to go back to his team and tell them that three months of work was going to be wasted. When he finally was able to say, “This is what’s going on. This is why I’m not having this conversation.”
Honestly, everybody else came right to his rescue. It was like, “How do we help you? How do we support you in getting the right message back to your team?” It was amazing, because until then, everybody thought he was just being a dragon. Once they understood, “That’s meaningful treasure. We get it.” All of a sudden, they were on his side trying to problem-solve about how they did it. It makes a massive difference.
You got to know your own treasure. The more you can understand the things that are likely to trigger you in any situation, the better prepared you are. Also, when it happens, to know, “I got to do the work myself to figure out what’s this about and to get that into the conversation.” It’s amazing how different it is. Once I tell people about when the dragons breathe fire, it’s because they’re protecting treasure. They’ll tell me ages later, “That’s so helpful. I think about it so differently now.”
That’s a powerful metaphor and it works well. Let’s talk about the last one. I think about energy management, Tony Schwartz. That’s how I was introduced to this. His firm came and did a training program when I was working at Fidelity many years ago. Help us understand where that fits into this equation of thought load and how you can manage your energy in a practical sense.
The top of the thought load equation is the cognitive demands in the emotional burdens, that’s the load. I’m sure you can think of a day where you were carrying a heavy load no sweat. You’re like, “I got this>.” You’re well rested and in a good place.
That was 1988.
It was a great year, but then you can probably think of another day where even something that wasn’t very heavy loaded at all just felt too much because you were depleted. That’s how energy factors into the equation. There’s three things I talked about. We take our night and we get them past the fire breathing dragons, and now they have to figure out how to fill their chalice. How do I fill my cup? How do I make sure I have the energy to keep going?
There’s three things. One, how do I find waterfalls to fill my cup from? How do I get flow into my week? Work that matters or work I’m interested in. Chunks of time where I am able to work unimpeded, undistracted. Finding waterfalls, but also finding wells. I have an assessment tool that I share with folks on the website that allows them to figure out what is your unique brand of overwhelm. We have people who are overwhelmed and become whirlwinds just like acting to feel busy. We have other people who become sticklers who just go back to the rules because that makes them feel like things are a little more predictable.
There’s four different styles. Knowing which one you are helps you understand what’s the well you can dig deep and find energy from. Whether that be planning and order or physical activity. Maybe you’re a rogue and you can deal with your overwhelm and build your energy by connecting with others more socially. It’s understanding that. When you can’t find a waterfall, you at least can tap a well of energy that you have. The third and final piece is, if your cup has cracks in it, no matter how much you’re doing to try and restore your energy. It’s not going to help.
Figure out what’s in your week. Are there a bunch of meetings in your week that are cracks in your cup? Are there relationships that are toxic? Are there conflict depths you have that because you’re trying to work around that conflict that you’re burning a lot of extra energy? Thinking about, what are my waterfalls, what are my wells and how do I make sure to fix the drains so that my energy becomes a renewable resource instead of what it feels like now. It feels like we’re burning fossil fuels in this finite energy like I got no more left. Humans are the ultimate renewable energy machines if we treat our machines well.
There’s a ton of things in the book, Liane. You did a great job of being practical and being buoyant. There’s a lot that people can take away individually for organizations and the leaders of those organizations. What message would you want to leave them with in terms of how they can better create the conditions for success to ease this following burden that’s endemic around organizations?
I would say stop managing workload and start managing thought load. Managing workload is not enough anymore. If you don’t know what’s in your team’s thought load, that could be tasks coming from parts of the matrix in the side door and the back door that you didn’t know about. Also, what are the stresses they’re experiencing or what are the things that are burning them out. Manage for thought load. Not workload. If we take one example. AI is that great example.
Whereas chatbots and agentic AI may be wonderful for their workload, the research is showing it’s hard on thought load. If you’re going to integrate AI into people’s workflow, great. We need to understand how it affects their cognitive demands, where it creates emotional triggers and makes people less productive instead of more. A lot of AI sends you off in multiple directions. How is it burning our energy? Is it doing it wisely? As leaders manage for thought load, not just workload. You will find you get so much more creative work, more innovative, more collaboration, and just so much less stress. It’s a positive thing when we can make that switch.
It’s easier said than done.
It is.
A lot of organizations and leaders are so output focused. They’re so financially driven. Taking that step back, even since the end of the COVID pandemic feels like we’ve taken a big step back and having this wellness, emotional health conversation that we are having in spades in 2020 because people view it as a distraction. They want to ignore it because it doesn’t help them hit quarterly goals. That’s unfortunate because we’re trying a lot of people.
I do think the way you said it is true. We’re focused on outputs and burning people out may get us lots of output. I’m quite convinced it does not get us the outcomes that we want. Those short-term measures that we’re using may look healthy but the long-term measures aren’t. I don’t even need a leader to believe that someone’s thought load is intrinsically meaningful.
If you want Innovation, sustained performance, or a great customer experience, all of those things, I promise you that managing thought load is essential to getting the outcomes you want. It’s when we’re stuck in this productivity trap of thinking the more we churn out, the more effective we are as a corporation. That’s why we’re stuck.
That’s a big part of why we’re stuck, too. Thank you. Thanks for doing this. As I mentioned at the outset, your book Thoughtload is going to be out by the time this episode airs. People will be able to buy it right then and there and benefit from it. Thanks for writing about it.
I needed to read it and I needed to live it. I’m constantly managing my own thought load, too.
Thank you again.
—
A terrific discussion withLiane. What I want you to take away from what we talked about, first and most importantly, is this idea that what is consuming you, what is overwhelming you is not just your workload. It is your thought load, which plays a multiplicative effect on top of your workload. This idea of cognitive switching is like multitasking, the emotional burden that we’re all carrying either because of things going on at home or at work and depleted energy. Which is definitely a crisis in the United States if not elsewhere. All of these things contribute in a multiplicative way to the work that you’re doing. It’s not just the tasks on your plate.
The second thing, as we’re talking about cognitive load. Attention is your most valuable resource. We talk a lot about time and time is definitely very valuable, but you’ve got to make sure that you are using your time well. You can use your time poorly. If you’ve got attention, it means you are using your time better. By definition, you will be more productive and more effective. We then talked about emotional load. That is a big part of the job. We are all carrying a lot. We’re always carrying a lot, whether it’s driven from things going on at home or at work.
If you’re a manager, you’re carrying that from your team and potentially contributing to their thought load because you are bringing your emotional burden and creating this sense of contagion to them in addition to them doing it to you. Finally, is this idea of energy being a huge performance lever. It’s how you manage both the things that bring you in energy and the things that deplete your energy. You have to constantly keep enough gas in the tank. If you’re not doing enough things that bring you energy and you’re doing a lot of things that deplete it. You’re just going to burn yourself out. You’re not going to be able to have attention. You’re not going to be able to handle the emotional aspects of your job.
All these things are related. Again, a terrific discussion with Liane. Her book. Thought load is available. If your interest has been piqued by this conversation, please go buy the book. Thanks for tuning in. I invite you to subscribe to Career Sessions onApple Podcasts andSpotify andYouTube and any of the other platforms that are available. If you found this discussion enlightening, sign up for my membership community, which is calledPathWise and subscribe to our newsletter PathWisdom. Thanks.
Liane Davey is an Organizational Psychologist, CEO advisor, and sought-after keynote speaker with more than 25 years of experience researching and advising teams on how to perform at their best. Known as the “teamwork doctor,” she works with teams from the frontlines to the boardroom, across industries and around the world, from Boston to Bangkok. Through her work with hundreds of teams, including 26 Global Fortune 500 companies (and counting), she has developed a practical, research-backed approach to solving the challenges that prevent teams from working effectively together.
Liane is a New York Times bestselling author of You First: Inspire Your Team to Grow Up, Get Along, and Get Stuff Done, The Good Fight: Use Productive Conflict to Get Your Team and Organization Back on Track, and her forthcoming title, Thoughtload: Manage the Madness and Free Your Team to Do Great Work (Page Two, May 2026). Her work focuses on increasing productivity, strengthening engagement, developing leaders, and helping teams navigate conflict in healthier, more effective ways.
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Informative article we have similar thoughts https://remaplife.in/