Successful mentoring programs pair people on purpose, give each pairing a clear goal, and measure what changes. They are formal, not left to chance. The best ones also match the format to the problem: one-to-one for skills, group for belonging, reverse for digital fluency, and sponsorship for promotion.

Most companies already run some version of this. The gap between programs that last and programs that fade is rarely budget. It is design, ownership and follow-through. This article looks at the main formats, documented examples of mentoring in the workplace, and the traits that successful mentorship programs share.

What makes a mentoring program successful?

A formal mentoring program is successful when it changes something you can count: engagement, retention, promotion readiness or skills. The pairing itself is not the result. The result is what the pairing produces.

Gallup’s research on mentors and sponsors shows why structure matters. In Gallup research based on a 2022 survey of U.S. employees, only 40% said they have a mentor at work, and just 23% have a sponsor. Employees with either a mentor or a sponsor were twice as likely to be engaged and more than twice as likely to strongly agree that their employer provides a clear career development plan. Gallup also found that formal mentoring and sponsoring relationships have a greater effect on development than informal ones.

Access is the other half of the story. When mentoring depends on who you already know, it favors people who already have networks. Formal programs open the door wider. That matters for employee career development programs built to reach everyone, not just the visible few.

If you want the step-by-step build, our sister guide on corporate mentoring programs covers it. This article stays on what good looks like once a program is running.

Which mentoring formats work, and when?

Employee mentoring programs usually take one of five forms. Each solves a different problem, so the “best” format depends on your goal.

1. One-to-one mentoring. A mentor and mentee meet on a regular cadence. It suits skill building, role transitions and onboarding. Cisco’s MentorMe program for female university students pairs weekly group sessions with one-on-one mentor matching. Each cohort runs for nine weeks. In a 2021 update on the Australia and New Zealand program, Cisco said MentorMe had supported more than 170 students, and that one 2017 participant later joined Cisco’s virtual sales team. The program is aimed at students, but the structure works as a template for early-career hires too.
2. Group and cohort mentoring. One mentor works with a small cohort, or a cohort moves through a program together. It scales better than one-to-one and builds peer networks along the way. Mastercard’s Uplift program, run by its LEAD business resource group, pairs Black men at the company with mentors in small cohorts. In February 2024, after the program doubled in size from its pilot cohort, Mastercard reported more than 30 participants across 10 countries, from entry level to executive vice president, with every participant saying the program met or exceeded expectations. Deloitte’s Women’s Mentoring Network in Bosnia and Herzegovina follows a similar cohort model. Its fourth season closed in October 2024 with 50 mentees in the final training session.
3. Reverse mentoring. Junior or specialist employees mentor senior leaders, usually on technology, tools or how the organization looks from below. A SHRM report from May 2025 traces the idea to Jack Welch at GE and lists Fidelity, Target and Cisco among firms that have used it in recent years. Procter & Gamble describes two live examples on its own site: a CIO Technical Advisory Board that explores technology trends for executives, and a Baby Care supply program launched in January 2024. One senior director said that instead of spending hours generating reports, his team now spends minutes getting the data.
4. Peer mentoring. Colleagues at a similar level trade experience, often across functions. It carries less hierarchy and works well for new managers who need a sounding board more than a senior authority. Few peer programs have publicly documented results, so treat this as a format to pilot, not a proven playbook.
5. Sponsorship. A sponsor is a senior leader who uses influence to advance someone’s career. Mentors advise; sponsors open doors. A SHRM piece from October 2025 reports that 54% of employees with a mentor or sponsor feel strongly motivated to overcome career challenges, compared with 35% of those without one. It also notes that Black employees with sponsors are identified as high potential twice as often as those without.
6. Choosing a format. If you only have capacity for one new format this year, start with the one that matches your most expensive talent problem. Weak promotion pipelines point to sponsorship. Siloed teams point to cohort or peer groups. A leadership team that lags on digital skills points to reverse mentoring.

What do successful mentoring programs have in common?

Across the examples above, five traits repeat. None is exotic, and each is something HR can verify.

1. A defined audience and purpose. Uplift serves a specific group with a specific concern: how to find opportunities and get known by executives. The P&G programs target digital skills for leaders. Neither tries to be a generic “mentoring for everyone” effort. A narrow purpose makes matching, content and measurement easier.

2. Executive visibility. Mastercard’s program draws participants from entry level up to executive vice president, and P&G’s reverse mentoring involves senior directors as mentees. When leaders participate, employees read the program as a priority. SHRM’s October 2025 reporting makes the same point from the sponsorship side: advancement happens when senior people spend their own capital.

3. Structure with room for the relationship. Cisco’s nine-week arc and Deloitte’s season-based cohorts give participants a rhythm. Fixed dates, session cadence and a closing event stop programs from drifting. Within that frame, pairs and groups still choose their own topics.

4. Training for mentors and mentees. Deloitte closed its fourth season with a final training session for 50 mentees. Mentoring is a skill. People who have been told what a good first conversation looks like use their time better. Mentees need guidance too. They get more from a mentor when they arrive with a specific request, not a vague wish for advice.

5. A feedback loop that leads to change. Mastercard reported that satisfaction grew by 23% from the previous year, which suggests the team collected feedback and acted on it. Programs that run a survey and file the results do not improve.

Mentoring also does not replace the manager relationship. Strong programs sit beside good 1×1 meetings, not in place of them. A mentor can discuss a career move that a direct manager cannot. A manager still owns day-to-day performance.

Which metrics show a mentoring program is working?

Measure outcomes, not activity. The number of pairs matched tells you little. These indicators tell you more.

• Engagement: Gallup found employees with a mentor or sponsor were twice as likely to be engaged. Compare mentored and unmentored groups in your own survey data.
• Career development clarity: Ask whether employees strongly agree they have a clear development plan. This is the same question Gallup used.
• Retention: Track 12-month retention for participants against a comparable group. Mentors and mentees both belong in the analysis.
• Promotion and mobility: Track internal moves and promotions, and look at who gets them. If sponsorship is working, high-potential identification should become more even across groups.
• Participant satisfaction: Mastercard’s result that every participant said the program met or exceeded expectations is a useful reference, but treat self-reported satisfaction as a floor, not proof.
• Mentor pipeline: SHRM’s reverse mentoring article cites that nearly nine in ten mentees go on to mentor others. A rising share of alumni who become mentors signals a program that sustains itself.

Be careful with comparisons. People who volunteer for mentoring may already be more motivated, so results can look better than the program deserves. Matching participants to a similar non-participant group reduces that bias. Retention is the metric most executives care about, and mentoring is one lever among several. Our guide to career coaching and employee retention shows how development support connects to people staying.

How do mentoring programs fail?

Failure usually has one of three causes. Matches are made on convenience, not fit. Mentors never learn what is expected of them. Or nobody owns the program after launch, so participation decays by the second quarter.

A fourth, quieter cause is network blindness. Mentors help most when they connect mentees to other people, not just share advice. That is the idea behind your network is your net worth: a mentor’s introductions often matter more than their advice. If your program never asks mentors to make introductions, add that expectation.

Scale matters at mid-sized companies. Fortune reported in October 2025 that virtually all U.S. Fortune 500 companies now offer formal programs, and SHRM data cited there says four in five organizations with formal programs find them effective against talent shortages. Fortune’s analysis means peer companies have likely set a baseline your candidates expect. You do not need Fortune 500 resources to meet it. A single well-run cohort beats a company-wide program with no owner.

Putting these examples to work

The pattern is consistent. Successful mentoring programs pick a clear audience, involve senior leaders, give participants structure and training, and track outcomes that matter to the business. Format is a tool, not a strategy.

If you are choosing a format or fixing a program that has stalled, talk to Pathwise about your goals. Our leadership coaching and development work is outlined on our for companies page.

Hybrid remote work means an employee splits the work week between a company workplace and a remote location, usually home. Employers set the mix. Some fix the office days. Others let staff choose. It is not full-time remote work, and it is not full-time office work.

For job seekers, the label is a prompt to ask which days, who decides, and where you must live. For employers, it is a policy that needs clear rules and trained managers. This guide covers both.

What Does Hybrid Remote Mean for Employees and Employers?

Hybrid remote sits between two ends of a spectrum. On one end, all work happens at an employer site. On the other, none does. Employers define the middle differently, so the same label can describe very different weeks.

Gallup’s July 2026 analysis shows how common the middle has become. Among remote-capable U.S. employees, 52% are hybrid, 26% are exclusively remote and 22% are fully on-site. Hybrid workers spend about 46% of the workweek on-site, roughly 2.3 days.

Those figures cover only jobs that can be done away from a workplace. Roles such as nursing, retail and manufacturing are outside the “remote-capable” group.

Four terms often get mixed up:

• On-site: Work happens at the employer’s location, with little or no remote time.
• Hybrid remote: Work is split between a workplace and a remote location. Also called hybrid work.
• Remote-first: Remote is the default. The office, if one exists, is optional or used for planned meetups.
• Fully remote: No regular office requirement at all.

What Is a Hybrid Remote Job?

A hybrid remote job requires some time at a company workplace and lets you do the rest from home or another approved place. Listings rarely spell out the details, and the details decide whether the job fits your life.

Ask these questions before you apply or accept an offer:

• Office days: How many days per week or month, and are they fixed or flexible?
• Who decides: Does the manager, the team or the employee pick the days?
• Location rules: Must you live within commuting distance? Is travel to the office covered?
• Equipment and costs: Is there a home office stipend, and is there a desk waiting at the office?
• Evaluation: How is performance judged when colleagues see you less often?

Employers can read this list as a checklist for their own job postings. A listing that answers all five questions attracts candidates who fit the arrangement and filters out those who do not.

Four Hybrid Work Models Employers Use

Most hybrid arrangements fall into one of four models. The right one depends on the work, the team and how much coordination the job needs.

Fixed Hybrid

Everyone in a team or company follows the same schedule, such as Tuesday through Thursday in the office. Fixed hybrid gives predictable overlap and makes it easy to plan in-person meetings. It offers the least personal flexibility.

Flexible Hybrid

Employees choose their office days within guidelines, such as a monthly minimum. This model gives the most autonomy. It also makes it harder to know who will be in the room on any given day, which complicates collaboration and desk planning.

Office-First Hybrid

The office is the default, and remote work is a limited exception, often one or two days. This fits roles tied to equipment, clients or on-site training. The risk is that remote days feel like a perk that can be withdrawn.

Remote-First Hybrid

Remote is the default for everyone, and the office is optional or reserved for planned team gatherings. This model suits distributed teams. It works only if documentation, onboarding and decisions happen in writing rather than in person.

Schedules in practice cluster around the middle. In the Owl Labs 2025 State of Hybrid Work survey of 2,000 full-time U.S. knowledge workers, three office days a week was the most common hybrid arrangement at 39%. Another 34% of hybrid workers went in four days.

Who sets the schedule also varies. Gallup reports that hybrid schedules are set by the manager or team in 35% of cases, by the individual in 34% and by the employer or leadership in 31%.

The split matters. Employees on fully self-determined schedules were 76% more likely than those on team-determined schedules to name burnout or fatigue as their biggest challenge.

The takeaway: flexible hybrid works best when the team agrees on norms together, not when every person decides alone.

How to Write a Hybrid Work Policy That People Can Follow

A hybrid policy turns a model into rules people can act on. Gallup found that teams with a formal hybrid collaboration plan were 66% more likely to be engaged and 29% less likely to experience burnout. The plan does not need to be long. It needs to answer the same questions every time.

Cover these items, in this order:

1. State the purpose of on-site time. Name what the office is for, such as connection, collaboration, creativity or culture. Days without a purpose become commuting for its own sake.
2. Define eligibility. List which roles can use hybrid arrangements and why. Explain exceptions in plain terms so they do not read as favoritism.
3. Set the schedule rule. Choose anchor days (days the whole team is in the office together), a weekly minimum, or a monthly minimum. Say who sets the schedule and how changes are approved.
4. Set core hours and response times. Give a daily overlap window for live work. Add expectations for asynchronous replies, especially across time zones.
5. Cover equipment and costs. State what the company provides for home setups, desk booking at the office, and travel for required in-person days.
6. Write meeting norms. Decide how mixed meetings run, so remote participants are not an afterthought. Examples follow in the manager section below.
7. Define how performance is judged. Tie evaluations and promotions to outcomes and written criteria, not to hours seen in the office.
8. Set a review date. Revisit the policy at a fixed interval, such as every six months, and collect feedback from employees and managers before changing it.

A policy only works if managers apply it the same way. Many HR teams pair the written policy with manager training and team workshops so the rules show up in daily decisions, not just in a handbook.

How Managers Lead Hybrid Teams Fairly

Manager skill matters more than the schedule. Gallup’s analysis associates an effective manager with four times higher engagement and wellbeing, regardless of how often employees work remotely. Three habits make the biggest difference in a hybrid team.

Reduce Proximity Bias

Proximity bias is the habit of favoring people you see in person. A version of it shows up in the Owl Labs survey: managers worried more about the satisfaction of in-office employees (33%) than that of remote employees (26%). The same pattern appeared for overwork and burnout, at 27% for in-office teams and 21% for remote teams.

Managers can counter it with simple practices:

• Review assignments by location: Check who gets high-visibility projects and stretch work. Look for patterns tied to where people sit.
• Judge by written criteria: Use agreed outcomes and goals, not impressions from hallway time.
• Check in evenly: Give every direct report the same cadence, whether in person or on video.
• Record decisions in shared channels: Decisions made at the coffee machine exclude remote colleagues, so post them in writing afterward.

Run Meetings That Work in Mixed Rooms

Mixed meetings are where hybrid teams feel unfair fastest. Owl Labs found that workers average five online or hybrid meetings a week, 77% have lost time because a meeting started late due to technical difficulties, and in-office workers spend an average of six minutes getting each meeting started.

Set meeting norms and hold to them:

• Test the technology first: Use a room camera that shows every face, or have in-room attendees join on their own devices.
• Invite remote voices first: Ask remote participants to speak before the room does.
• Share a written agenda: Send it ahead and post notes and action items afterward.
• Assign a chat monitor: One person watches the chat and raises questions from remote attendees.
• Audit the calendar: Cut meetings that exist out of habit. Guidance on workplace productivity includes a meeting audit approach you can adapt.

Communicate and Give Feedback on a Schedule

Hybrid teams lose the informal feedback that office proximity provides. Gallup reports that only 21% of employees strongly agree they received meaningful feedback from their manager in the past week, and that those who do receive weekly feedback are four times more likely to be engaged.

Replace chance conversations with structure. Hold regular one-on-one meetings at the same cadence for everyone. State priorities in writing. Treat clarity as part of the job. Managers who want to sharpen this skill can build on leadership communication skills such as listening, giving direction and delivering feedback.

Build Connection Across Locations

Connection does not happen by accident when people are in different places. Plan it. Use short team exercises at the start of meetings, pair remote and on-site colleagues for projects, and schedule in-person days around work that benefits from being together. The exercises in this list of communication skills activities work in person and on video.

How to Roll Out and Measure a Hybrid Model

HR and L&D teams can move from model to practice in about a month if the steps are clear.

1. Week one: Ask managers and employees what works and what does not today, using a short survey or listening sessions.
2. Week two: Draft the policy using the eight items above, and check it against two or three real team schedules.
3. Week three: Brief managers on the policy, proximity bias and meeting norms, and give them talking points for questions.
4. Week four: Launch the policy, publish a one-page summary, and put the review date on the calendar.

Then track results by work arrangement, not only in total:

• Engagement: Compare pulse survey results for on-site, hybrid and remote staff.
• Retention: Compare attrition across the same groups.
• Advancement: Compare promotion and project assignment rates by location.
• Meeting quality: Track late starts, technical failures and complaints about mixed meetings.
• Office use: Compare actual attendance on anchor days with what the policy expects.

Gaps between groups point to where a manager, a norm or a rule needs attention.

How PathWise Helps Teams Make Hybrid Work Fair and Clear

Hybrid work succeeds or fails on manager habits and written rules. A clear model, a one-page policy and consistent meeting norms give every employee the same chance to contribute, wherever they sit.

PathWise works with HR and L&D teams on manager development, team workshops and leadership coaching. See corporate training and manager development for teams to plan a program that fits your hybrid model and your managers.

Works Cited

• Business Wire. “Owl Labs’ 2025 State of Hybrid Work Report Finds the New Frontier of Flexibility is When Employees Work, Not Where.” Business Wire, Sept. 2025. https://www.businesswire.com/news/home/20250922965079/en
• Gallup. “Hybrid Work and Productivity: What the Data Show.” Gallup Workplace, 27 July 2026 (updated 28 Sept. 2026). https://www.gallup.com/workplace/713093/hybrid-work-productivity.aspx

The pros and cons of AI in the workplace are easy to summarize. The pros are faster routine work, better-informed decisions, and more time for judgment-heavy tasks. The cons are job disruption, biased or wrong outputs, data privacy exposure, and skill erosion. Most cons are management problems, and clear policy, training, and manager support reduce them.

This guide covers artificial intelligence in the workplace from both sides. It then shows what HR and L&D leaders can do about the risks, with steps a manager can start this month.

What Is Artificial Intelligence in the Workplace?

Artificial intelligence in the workplace means software that learns from data to draft, predict, classify, or recommend. Generative AI writes and summarizes. Machine learning models forecast demand or flag fraud. Agentic AI goes a step further and completes multi-step tasks with limited supervision.

Use is now mainstream. Gallup’s 2026 AI at work tracking shows 52% of U.S. employees use AI at work a few times a year or more, 30% use it a few times a week or more, and 15% use it daily.

Daily use reaches 42% in technology but stays between 9% and 15% in seven of the other industries Gallup tracks.

Pros of AI in the Workplace

The benefits of AI in the workplace show up in time, decision quality, and employee experience.

Faster Routine Work

AI takes first drafts, summaries, data entry, and scheduling off people’s plates. In McKinsey’s 2026 state of AI survey, eight in ten respondents say AI has improved their own productivity. Gallup finds that 65% of employees in organizations that have implemented AI report a positive effect on productivity and efficiency.

The saved hours matter most when managers point them at higher-value work, such as customer conversations, analysis, and mentoring.

Better Decisions From Data

AI can scan more data than any analyst can read. It spots patterns in sales, attrition, quality defects, and support tickets. McKinsey reports that 50% of respondents say AI helps them make better decisions. The tool gives a better starting point. A person still owns the call.

A Better Experience for Employees and Customers

Chatbots answer routine HR and customer questions at any hour. AI can tailor learning paths to a person’s role and skill gaps. In hazardous settings, sensors and computer vision can flag unsafe conditions before an injury occurs. Each use needs a human fallback for the questions a bot cannot handle.

Cons and Disadvantages of AI in the Workplace

The disadvantages of AI in the workplace fall into five groups. Four are about the tool. The fifth is about leadership.

Job Disruption and Employee Anxiety

Fear of job loss shapes how people respond to AI, and the data shows a gap between fear and fact. In McKinsey’s survey, 39% of respondents expect AI to decrease their organization’s headcount over the next year. Just 14% of respondents from organizations using AI report that AI contributed to an overall decline.

The worry still has a cost. Microsoft’s 2026 Work Trend Index finds that 65% of AI users fear falling behind if they do not adapt quickly. Roles change faster than headcount. Tasks inside a job get automated first, so job descriptions, career paths, and performance goals need updating.

Bias, Errors, and Hallucinations

AI systems learn from historical data, so they can repeat historical bias. A hiring screen trained on past hires may favor the profiles that were hired before. Generative AI can also invent facts, a failure called hallucination, and state them with confidence. Any output that affects hiring, pay, safety, or legal decisions needs a documented human review.

Privacy, Security, and Shadow AI

Shadow AI is the use of AI tools the employer has not approved. Employees paste meeting notes, client data, or code into public tools to save time. That data can leave the company’s control. Without an approved tool list and a rule on what data may be shared, the risk grows with every new tool people try.

Skill Erosion and Over-Reliance

People who let AI write every first draft lose practice in writing, analysis, and critical thinking. This habit is known as cognitive offloading. Skills fade without use, so teams need tasks where people work first and check against AI second.

No Clear Plan From Leadership

The most common con is not technical. Gallup finds that only 25% of U.S. employees say their organization has communicated a clear plan for integrating AI into current practices. Without a plan, each team improvises its own rules.

Why Most of the Cons Are Management Problems

Culture, manager support, and talent practices explain more of AI’s value at work than individual skills do. The Work Trend Index puts these structural factors at 67% of AI’s real impact, against 32% for individual mindset and behavior. Microsoft notes these are statistical associations, not proof of cause. The survey covered 20,000 knowledge workers who use AI across 10 markets.

Incentives point the same way. Only 13% of AI users say they are rewarded for reinventing work with AI even when results fall short.

Managers sit in the middle: Gallup reports that 36% of employees strongly agree their manager supports their team’s use of AI. Unclear policy, thin training, and unprepared managers drive most of the cons above. HR can fix all three.

What HR and L&D Leaders Should Do About the Cons

Pair each con with an owner and a control. Five moves cover most of the risk.

Write a Plain-Language AI Use Policy

Start with a one-page AI workplace policy that every employee can read in five minutes. Cover three things:

• Approved tools: name the tools staff may use and who approves new ones.
• Data rules: sort information into never share, share with approval, and safe to share.
• Review rules: state which outputs need human review before use, such as hiring, pay, legal, and client-facing work.

Check local rules on automated hiring tools with counsel before rollout.

Train Managers Before Everyone Else

Managers decide whether a policy becomes daily practice. Give them a short toolkit: how to discuss job security honestly, how to set team AI norms, and how to coach someone whose AI output is weak. Many companies build this through manager development programs that pair coaching with practice.

Upskill by Role and Protect Human Skills

Generic AI courses fade fast. Teach people how AI fits the tasks they do each week, and let them practice on real work. Our guide to AI upskilling for employees lays out a role-based approach.

Pair it with training in the skills AI does not replace: critical thinking, communication, and judgment. See how to keep the human touch as AI scales.

Communicate the Plan and Lead Through Change

Silence is the weak point, so close the gap. Tell employees which tasks are changing, which are not, and when the next update will come. Answer the headcount question honestly. If you do not know, say so and set a date. Managers who know how to lead through change can use ready-made scripts for these conversations.

Build Paths for Roles That Change

When tasks shift, roles should shift with them. Map which roles gain or lose tasks, and show people where their skills can move next. A strong internal mobility program turns fear of displacement into a visible career path.

Measure More Than Usage

Logins do not show whether AI is working. Track these instead:

• Clarity: the share of employees who can state the AI plan, from a quarterly pulse survey.
• Manager support: the share who agree their manager supports their team’s AI use.
• Quality: AI-related errors caught in review, and how many reached customers.
• Skills: assessed AI and critical-thinking skill by role, not course completions.
• Risk: reports of unapproved tool use and data incidents.

Three Team Exercises Managers Can Run This Month

• AI norms session (30 minutes): the team lists tasks where AI is encouraged, allowed with review, or off limits. Record the result on one shared page.
• Output review drill (20 minutes): hand the team an AI-written draft with planted errors. People find the errors and explain how they caught them.
• Role redesign map (45 minutes): each person lists their five most repeated tasks, marks which AI could draft, and names the new work they would do with the time.

Repeat each exercise after a quarter. Norms drift as tools change.

How Employees Can Stay Relevant as AI Spreads

Employees have a role too. Learn the approved tools, keep a record of work you improved with AI, and strengthen skills that are hard to automate, such as negotiation, coaching, and judgment under uncertainty. AI career planning shows how to map your skills against changing roles.

Conclusion

The pros and cons of AI in the workplace tip toward the pros when leaders manage AI as a people change. The payoff comes from everyday habits: who checks the output, which data stays private, and whether a manager can explain what is changing. Start with the policy and the managers, then widen the effort to skills and career paths.

How PathWise Helps Teams

PathWise supports mid-sized companies with the human side of AI change. Our workshops build communication, decision-making, and executive presence. Our leadership and manager development gives people managers practice leading teams through change. Explore corporate training and leadership development for your teams to plan a rollout that fits your size and priorities.

Works Cited

• Gallup, “Global Indicator: Artificial Intelligence (U.S. AI at Work),” Gallup, 2026 (page published Jan. 2026, updated Apr. 2026, figures labeled as of May 2026). https://www.gallup.com/699797/indicator-artificial-intelligence.aspx
• Tinkoff, Dan, Lieven Van der Veken, Michael Chui, and Tara Balakrishnan, “The State of AI in 2026: On the Road to ROI,” McKinsey & Company, 25 Aug. 2026. https://www.mckinsey.com/capabilities/quantumblack/our-insights/the-state-of-ai
• Microsoft, “Agents, Human Agency, and the Opportunity for Every Organization,” 2026 Work Trend Index, Microsoft WorkLab, 5 May 2026. https://www.microsoft.com/en-us/worklab/work-trend-index/agents-human-agency-and-the-opportunity-for-every-organization

Leadership communication skills are the abilities that let a leader set direction, listen, give feedback, and keep people informed so a team can act on the same priorities. The core skills are clarity, active listening, feedback, adaptability, and the judgment to match each message to its audience and moment.

These skills can be learned. Managers build them through repeated practice in real situations, not through personality. This guide covers the skills managers and senior leaders need most, with scripts you can use this week and a plan for developing them across an organization.

What Are Leadership Communication Skills?

Leadership communication is how a leader shares direction, listens, and builds trust so people know what to do and why it matters. It differs from everyday workplace talk in purpose. A leader’s messages set priorities, shape morale, and decide whether a decision gets carried out or quietly ignored.

It builds on effective communication skills such as clear speaking, careful listening, and clean writing. Leadership adds three demands. You speak for the organization, your messages must survive several layers of retelling, and your tone is read as a signal. A casual hallway comment can travel faster than the official announcement.

Communication in leadership also runs in four directions, and each needs a different format and level of detail:

• Down: direction, expectations, and context for direct reports.
• Up: status, risks, and requests to senior leaders and executives.
• Across: coordination with peers and other departments.
• Out: messages to customers, partners, and the wider organization.

Why Communication in Leadership Matters for Teams

Managers shape the daily experience of work. Gallup research finds that managers account for 70% of the variance in team engagement. Yet Gallup’s State of the Global Workplace 2026 report puts manager engagement at only 22% globally, barely above the 19% for individual contributors.

That gap is a communication problem as much as a morale problem. Stretched managers have less room for the conversations that keep teams aligned: explaining priorities, answering questions, and checking understanding.

Employees also want the conversations. A May 2026 article in HR Daily Advisor reports that 96% of employees say regular feedback helps them improve, and that nearly half do not get it as often as they need. For HR and L&D teams, this makes leadership communication a trainable, measurable manager behavior rather than a soft extra.

The 6 Leadership Communication Skills Managers and Senior Leaders Need

Six skills cover most of what managers and senior leaders do each week. Each one below includes wording you can adapt.

Setting Direction and Expectations

People cannot follow a direction they cannot repeat. State the goal, the reason, the owner, and the check-in point in plain words. Then ask the team to say it back in their own words.

• Goal: “Our priority this quarter is cutting client onboarding from three weeks to two.”
• Reason: “Slow onboarding delays revenue and ties up your capacity.”
• Owner: “Dana owns the checklist. Everyone owns their own handoffs.”
• Check: “Tell me what you heard and what you need from me.”

Senior leaders add one more step: say what is not a priority. Teams waste less time guessing when the trade-offs are named out loud.

Active Listening

Active listening means giving full attention, restating what you heard, and asking before you answer. It is the fastest way to find problems before they become escalations.

• Paraphrase: “So the delay is the vendor handoff, not the build. Is that right?”
• Probe: “What would make this easier next week?”
• Pause: Wait three seconds before replying. Silence invites the fuller answer.

In meetings, look at the speaker and keep your laptop closed. On video calls, turn off notifications so people can see you are present.

Giving Feedback

Feedback works when it is specific, timely, and about behavior. The Situation, Behavior, Impact (SBI) model from the Center for Creative Leadership gives a simple structure. Frequency matters too: Gallup reports that employees who receive daily manager feedback are 3 times more likely to be engaged than those who receive it once a year or less.

• Situation: “In Tuesday’s client call…”
• Behavior: “…you interrupted the client twice while she described her budget issue.”
• Impact: “She stopped sharing details, and we lost information we needed.”
• Next step: “Next time, let her finish and summarize before you respond. Can we try that Thursday?”

Use the same structure for praise. Specific recognition tells people which behavior to repeat.

Running One-on-One Meetings

The weekly check-in is where most manager communication happens. One-on-one meetings work best when the employee owns the agenda and the manager protects the time.

• First 10 minutes: the employee’s topics, blockers, and questions.
• Next 10 minutes: your updates, priorities, and context from above.
• Last 5 minutes: agreed actions and feedback in both directions.

Two questions open honest conversation: “What is getting in your way?” and “What could I do differently to support you?” Write down the answers and follow up at the next meeting.

Communicating Change

When information is missing, people fill the gap with rumors. A good change message answers four questions: what is changing, why, what stays the same, and what happens next. For a fuller playbook, see leading through change.

• What: “We are merging the two support teams on June 1.”
• Why: “Customers are being routed twice, and that slows every ticket.”
• What stays: “Your manager, your pay, and your core accounts do not change.”
• Next: “I will share the new structure Friday and hold open Q&A Monday.”

Repeat the message in more than one channel. If you do not know something, say so and name the date you will update the team.

Executive Presence and Senior-Leader Communication

Executive presence is how others read your credibility, composure, and clarity. Our guide to professional presence covers the fundamentals. In daily practice, it comes down to structure. Lead with the conclusion, give two or three supporting points, and state the ask. Barbara Minto’s Pyramid Principle teaches this answer-first order.

• Headline: “I recommend we delay the launch by two weeks.”
• Reasons: “Two integrations failed testing, and the fix needs ten days.”
• Risk: “Launching on time risks failed orders during peak week.”
• Ask: “I need your approval by Thursday to rebook the vendor.”

Pace matters as much as content. Speak slightly slower than feels natural, pause after key points, and keep your camera at eye level on video calls.

How Leadership Communication Changes as You Move Up

The skills stay the same. The emphasis shifts with each level of responsibility.

• First-time manager: Translate team goals into daily tasks, give small and frequent feedback, and hold consistent one-on-ones. The hardest shift is moving from peer to boss.
• Manager of managers: Cascade messages through layers without distortion. Give managers talking points, ask what they are hearing, and hold skip-level conversations.
• Senior leader or executive: Explain strategy, repeat it often, tie decisions to purpose, and balance transparency with confidentiality. You speak to many audiences at once: all-hands meetings, boards, customers, and investors.

Communication is one of the qualities of a good leader, but how it shows up changes at each level. In distributed teams, add one habit at every level: write the decision down. Post meeting notes with the owner and date so remote and hybrid colleagues work from the same record.

Common Leadership Communication Mistakes and How to Fix Them

• Announcing without explaining: People resist what they do not understand. Fix it by leading with the reason, then the decision.
• Treating silence as agreement: Quiet rooms often hide doubts. Ask each person directly, or collect input in writing before the meeting.
• Saving feedback for the review: By then the moment has passed. Move to short, regular feedback after real events.
• Using one channel for everything: Urgent items belong on a call, decisions in writing, and recognition in public. Match the channel to the message.
• Never saying “I don’t know”: Guessing damages trust faster than a gap in knowledge. Say what you know, what you do not, and when you will follow up.

Leadership Communication Self-Assessment

Answer yes or no. Ask a direct report or a peer to rate you on the same list for a more honest picture.

• Can each person on my team state our top three priorities without checking notes?
• Do I explain the reason behind decisions, not just the decision?
• Did I give specific feedback to each direct report in the last two weeks?
• Do I hold one-on-ones on a regular schedule and let the employee set the agenda?
• Do I paraphrase what I heard before I respond?
• Did I ask for feedback on my own communication in the last quarter?
• When I announce a change, do I say what stays the same?
• Do I write down decisions with an owner and a date?

Six or more yes answers suggest a solid base. With fewer, pick two items and practice them for four weeks before adding more.

How Organizations Develop Leadership Communication Skills

Individual effort helps, but organizations get more consistent results when they treat communication as a managed skill. HR and L&D teams can use six steps.

• Define the standard: Choose four to six observable behaviors, such as holding weekly one-on-ones, using SBI feedback, and giving a “what stays the same” statement in every change message.
• Set a baseline: Use 360 feedback or pulse-survey items such as “My manager explains why decisions are made.”
• Train with practice: Run workshops built on real scenarios and role play. Skills stick when managers apply them between sessions.
• Coach where it counts: Offer one-on-one coaching to new managers and senior leaders who carry the highest-stakes messages.
• Reinforce: Add talking-point templates, peer practice groups, and communication expectations to performance reviews.
• Measure: Track pulse-survey results, one-on-one completion rates, skip-level feedback, and 360 changes at six and twelve months.

Many HR teams pair internal practice with corporate training and leadership coaching so first-time managers and executives build the same shared language.

How PathWise Helps Teams Build Leadership Communication

PathWise works with HR and L&D teams to turn the habits in this guide into everyday manager behavior. Its corporate offerings include corporate training workshops, soft skills training for employees, 1:1 leadership, executive and management coaching, and a Manager Development Program.

If uneven manager communication is slowing alignment, feedback, or change in your organization, talk to PathWise about leadership development for your teams and build a plan around the skills your managers need most.

Works Cited

• Gallup, “State of the Global Workplace: 2026 Report,” Gallup, April 2026. https://www.gallup.com/workplace/697904/state-of-the-global-workplace-global-data.aspx
• Gallup, “How Can Leaders Improve Employee Engagement and Company Culture?,” Gallup, 21 Sept. 2026. https://www.gallup.com/workplace/712895/leaders-improve-employee-engagement-company-culture.aspx
• Bell, Ian, “Closing the Feedback Gap: Why Leadership Development Is Falling Short,” HR Daily Advisor, 15 May 2026. https://hrdailyadvisor.hci.org/2026/05/15/closing-the-feedback-gap-why-leadership-development-is-falling-short/

Leading through change means guiding a team through a new direction while keeping trust, focus, and output steady. A manager explains why the change is happening, sets clear next steps, listens to concerns, and adjusts as results come in. Good change leaders reduce uncertainty so people can keep doing good work.

Every manager faces this sooner or later. A reorganization, a new system, an AI rollout, a layoff, or a strategy shift can all ask people to work differently. This guide gives you a playbook, scripts, and a training checklist you can use with your own team.

What Does Leading Through Change Mean?

Leading through change is the people side of a transition: you own how your team experiences a change that someone else designed. The change leadership meaning for a manager comes down to three jobs.

• Translate: Turn the company announcement into what changes in your team’s daily work.
• Steady: Hold performance and morale while answers are still missing.
• Escalate: Tell senior leaders what is landing, what is not, and why.

Frameworks such as Prosci’s ADKAR model and Kotter’s eight-step process describe the organizational plan. This guide covers the layer they leave to you: what a manager says and does on an ordinary Tuesday. If you are coping with a change yourself, start with our guide on how to navigate change. This post stays on the manager’s side.

Why Leading Through Change Matters More Now

Most changes do not land well. Gartner research from July 2025 found that only 32% of mid-to-senior business leaders said the last change they led achieved healthy change adoption. The same release cited an April 2025 survey of more than 2,850 employees, in which 79% had low trust in change.

Low trust makes leadership through change harder for managers. Gartner’s modeling found employees were three times more likely to adopt changes on time and in a healthy way when leaders routinized change, even when trust was low. That points to a steady rhythm of short updates, not one big announcement.

Managers carry much of this load. In Wiley’s 2025 Workplace Intelligence report, based on 1,685 North American respondents, 52% of managers felt responsible for helping their teams through change. Only 45% felt adequately supported by senior leadership. Companies that want to close that gap can build manager capability through corporate training and leadership development.

A 5-Step Playbook for Leading a Team Through Change

Here is how to lead through change at any scale: use these five steps every time. Each step is one conversation or one written message.

• Name the change: State what is changing in one sentence, with no jargon. Say what is not changing too, so people can relax about the rest.
• Explain why now: Give the business reason and the cost of doing nothing. If you disagree with part of it, you still owe the team the reasoning you do accept.
• Define what success looks like: Describe the finished state and the first measurable sign of progress. Vague goals create anxious guessing.
• Set the next seven-day action: Give each person one concrete task for the coming week. Action turns worry into momentum.
• Check and adjust: Ask what is working and what is blocked, then change the plan where the team’s answers justify it.

What to Say and When During a Change

Timing matters as much as wording. Use this sequence as a default, then adapt it to your company’s rules.

• Before the announcement: Meet with HR and your manager to confirm what you can share. Take a baseline: current workload, key metrics, and team mood.
• Same day: Hold a live team meeting, then follow in writing. Repeat the same facts in both.
• Within 48 hours: Meet one-to-one with the people most affected. Ask what worries them most.
• Every week: Send a short update on a fixed day, even when nothing has moved.
• At 30 days: Review the baseline against today. Report what you learned to senior leaders.

How to Lead Through Four Common Types of Change

The right words differ by change type. Each has a typical fear and a typical mistake.

Reorganizations

People worry first about reporting lines, roles, and credit for past work. Say what is decided, what is still open, and when the open items close. Map new handoffs between teams in the first week. Unclear ownership is often where early friction starts.

New Technology and AI Rollouts

Do not assume fear. In Wiley’s survey, 68% of respondents felt excited or curious about AI. Ask each person where they stand before you plan. Explain what the tool is for, what stays human, and what the team can try without penalty. HR teams planning the skills side can start with this guide to AI upskilling for employees.

Layoffs

A layoff creates two audiences: the people who left and the people who stayed. Confirm wording with HR and legal counsel first. Tell the remaining team what changes in scope, who owns the displaced work, and what will not be dropped. Hold individual conversations within a day.

Do not promise there will be no further cuts unless leadership has confirmed it. Our guide to reduction in force explains the process.

Strategy Shifts

A strategy shift can make recent work feel wasted. Acknowledge what the team built. Say what ends, what continues, and which metrics now matter. Retire old goals in writing so people stop serving two sets of priorities.

10 Skills Leaders Need During Change

1. Focus on What Matters Most

Pick the two or three outcomes that must not slip and say them aloud. Give everything else a lower priority or a stop date. Trying to protect everything at once overloads people.

2. Take a Broad View

Look past your team’s slice. Ask how the change affects customers, neighboring teams, and handoffs. Talk to one peer manager each week so you hear about collisions before your team does.

3. Act with Urgency Without Burning People Out

Urgency means a short list of dated decisions, not constant pressure. Set a pace the team can hold for weeks. Remove one task for every new task you add.

4. Be Accountable

Own your part of the rollout, including your mistakes. If an announcement lands badly, say so and fix it. The difference between accountability vs responsibility matters here: you can delegate tasks, but you stay accountable for the result.

5. Act Decisively

Waiting for full information stalls everyone. Make reversible decisions quickly, label them as reversible, and set a review date. Save slow deliberation for choices you cannot undo.

6. Communicate Early and Often

Silence invites rumors. Share what you know, what you do not know, and when you will know more. For deeper technique, see our guide to leadership communication skills.

7. Lead with Emotional Intelligence When People Feel Unsafe

Name the emotion before you argue with it. Fear, anger, and grief are normal responses to loss of status or routine. Ask what worries each person most, then answer that worry instead of your assumption about it.

8. Practice Agility

Replace long planning cycles with short loops. A simple cadence works: one short meeting for priorities, one check-in for risks, and one written update.

9. Get Comfortable with Conflict

Disagreement during change is information. Invite it in the open, then decide. Set two ground rules: critique the plan, not the person, and do not reopen a decision without new facts.

10. Use Influence Instead of Control

You cannot order belief. Enlist respected team members as early testers and let them shape the details. People defend what they helped build, which makes leading people through change far easier.

Scripts Managers Can Use During Change

Adapt these lines to your voice. Keep the promises inside them, because teams remember who kept their word.

• Announcing a change: “Here is what is changing, why it is happening now, and what it means for our team. I do not have every answer yet. I will share the next update on Friday.”
• Handling resistance: “It sounds like you have a real concern about the new process. Tell me what you see that I might be missing. I cannot change the decision, but I can change how we carry it out.”
• Admitting uncertainty: “I do not know yet. I know when I will find out, and I will tell you the same day.”
• Giving a weekly update: “Here is what we finished, what changed, and what comes next. One thing is still unclear. What is getting in your way?”

How to Handle Resistance and Change Fatigue While Keeping Performance Up

In the Wiley survey, managers named unclear information from their organization and the challenge of balancing productivity with adaptation as their main obstacles. Few named employee resistance. Treat pushback as a signal and sort it by cause.

• Confusion: People do not understand the change. Restate it, give an example, and check understanding with a question.
• Loss: People will lose status, autonomy, or a skill they prized. Name the loss and show where their expertise still matters.
• Disagreement: People doubt the strategy. Listen, pass the useful points upward, and be honest about what cannot change.
• Overload: People have no capacity. Cut work before you add any.

Performance holds when the load is visible. Keep a written stop-doing list for the team. Protect focus blocks on the calendar. Reset targets openly instead of expecting the same output during a transition. Gartner also advises acknowledging progress on interim goals, so celebrate small milestones while the full vision is still moving.

What Leading Through Change Training for Managers Should Include

Training gaps are common. The Wiley report found that only 18% of respondents had received comprehensive change training, while 78% said it would be valuable.

Practice matters more than lectures. Gartner’s October 2025 research found that employees who applied a relevant change reflex were 3.5 times more likely to achieve healthy change adoption. Gartner recommends building practice into daily work through “micro-moments.” Effective leading through change training should therefore include these parts:

• Scenario practice: Role-play announcements, resistance conversations, and post-layoff team meetings, with feedback from a coach.
• Change-type playbooks: Separate guidance for reorganizations, AI rollouts, layoffs, and strategy shifts.
• A communication plan template: Managers draft a 30-day cadence for a real change before they leave the session.
• Listening and emotional regulation: Skills for staying calm in a hard conversation and hearing the actual concern.
• Sponsor alignment: A session where senior leaders and HR agree on one message, so managers do not hear mixed signals.
• Reinforcement: Peer groups and follow-up coaching at 30 and 90 days, tied to a live change.

How PathWise Helps Teams Lead Through Change

Change leadership is a skill managers can practice, not a trait they either have or lack. Companies get the best results when practice is tied to a real change in progress.

PathWise builds corporate training workshops, executive and management coaching, and custom programs that give managers rehearsal time with real change scenarios. Explore PathWise manager development and training for companies to design a program around your next reorganization, AI rollout, or strategy shift.

Works Cited

• Gartner, “Gartner HR Research Finds Just 32% of Business Leaders Report Achieving Healthy Change Adoption by Employees,” Gartner Newsroom, 8 July 2025. https://www.gartner.com/en/newsroom/press-releases/2025-07-08-gartner-hr-research-finds-just-32-percent-of-business-leaders-report-achieving-healthy-change-adoption-by-employees
• Gartner, “Gartner HR Research Finds Less Than Half of Employees Achieved the Change Goals Set by Their Organization,” Gartner Newsroom, 9 Oct. 2025. https://www.gartner.com/en/newsroom/press-releases/2025-10-09-gartner-hr-research-finds-less-than-half-of-employees-achieved-the-change-goals-set-by-their-organization
• Wiley, “New Survey Reveals Growing Risk of Change Fatigue, ‘Cascade Crisis’ for Employees Navigating AI,” Wiley Newsroom, 26 Aug. 2025. https://newsroom.wiley.com/press-releases/press-release-details/2025/New-Survey-Reveals-Growing-Risk-of-Change-Fatigue-Cascade-Crisis-for-Employees-Navigating-AI/default.aspx

The short leader and leadership definition is this. A leader is a person who guides others and answers for results. Leadership is the process of setting a direction and earning commitment to it.

A leader is a role someone holds. Leadership is something a group does. A title alone does not create it.

Leadership Defined: A Social Process, Not a Title

The Center for Creative Leadership (CCL) defines leadership as “a social process that enables individuals to work together to achieve results that they could never achieve working alone.” The definition says this holds regardless of position. Leadership is not a personality type or a rank.

CCL describes three outcomes, the direction, alignment and commitment (DAC) model:

• Direction: the group agrees on where it is going.
• Alignment: the work is coordinated so that individual efforts fit together.
• Commitment: people treat the group’s success as a personal priority.

When all three are present, leadership is happening. When one is missing, the team feels it. A group with direction but no commitment drifts. A group with commitment but no alignment works hard in different directions.

What Is a Leader? Meaning and Definition

A leader is a person others look to for direction, judgment and accountability. Where that trust comes from matters. Quarterdeck, a UK firm, separates authority that comes from a position from authority earned through competence and character. Good leaders build both.

Leaders come in three common forms:

• Formal leader: holds a role with authority, such as a team lead, director or chief executive.
• Informal leader: has no official authority, but colleagues seek out their advice and follow their example.
• Emergent leader: steps forward when a situation needs someone to take charge, then steps back.

Holding a role does not prove the person leads. A manager who assigns tasks but never clarifies where the team is heading is a leader on the org chart and absent in practice.

Leader vs. Leadership: What Is the Difference?

The difference between a leader and leadership comes down to who owns it. A leader is one person. Leadership belongs to the group and shows up in what people do together.

• Unit: a leader is an individual. Leadership is a pattern across several people.
• Source: a leader’s authority is usually granted by the organization. Leadership is earned each time the group moves in a shared direction.
• Durability: when a leader leaves, a role opens. When leadership is built into habits, it stays.
• Test: ask who the leader is, and you name a person. Ask where leadership is happening, and you describe decisions, handoffs and follow-through.
• Failure mode: a leader without leadership has a title and no direction. Leadership without a leader is a self-organizing group, sometimes called distributed leadership.

Any sound leader and leadership definition keeps the two apart. Searching for a better leader treats a capability problem as a hiring problem.

Leadership vs. Management

Management and leadership overlap, but they answer different needs. CCL describes management as planning and control, and leadership as people working together toward something they share. Most roles need both.

• Management: plans work, assigns resources, tracks progress and fixes problems.
• Leadership: clarifies direction, builds agreement and keeps people committed when the plan changes.

A team can be well managed and still lack leadership. Deadlines are met, yet nobody can say why the work matters. The mix shifts with seniority too. In the C-suite, executives lead an entire company through strategy, finance and culture, not one team’s task list.

Leadership Theories and Styles

Researchers have described leadership from many angles. Three theories show up most often, and a handful of styles round out the picture.

Transformational Leadership

Associated with the political scientist James MacGregor Burns, this approach has leaders lift motivation by tying everyday work to a bigger purpose. They coach people to grow, not only to comply. It fits teams facing major change.

Servant Leadership

Robert K. Greenleaf introduced the idea that a leader’s first job is serving the people they lead. The leader removes obstacles, shares credit and develops the team. Performance follows from growth and trust.

Situational Leadership

Paul Hersey and Ken Blanchard argued that no single style works everywhere. The leader adjusts how much direction and support to give based on the person’s skill and confidence with the task. A new hire needs more direction than a veteran.

Other Leadership Styles

• Authoritative: the leader decides and sets a clear course. It works in a crisis and wears thin over time.
• Democratic: the leader invites input before deciding. It builds buy-in and takes longer.
• Laissez-faire: the leader hands off and trusts skilled people. It fails when people need guidance.
• Authentic: the leader acts consistently with stated values, which builds credibility.
• Emotionally intelligent: the leader reads and manages emotions, their own and others’.

Styles are tools, not identities. The useful skill is choosing the right one for the moment.

Why the Leader vs. Leadership Distinction Matters for Companies

Most companies develop leaders. They promote a strong performer, hand over a team and send them to a course. That treats leadership as a title someone receives. The new manager has authority, but no practice setting direction or earning commitment.

Quarterdeck argues for developing leadership rather than just leaders, and for measuring leadership behaviors. CCL makes a related case: invest in leadership at all levels, grow teams together, and scale development across the organization. Both point the same way. Leadership is a capability a company builds, not a position it fills.

In practice, that changes four decisions:

• Promotion criteria: look for leadership behaviors people already show, such as running a cross-team project or unblocking a peer, not only tenure or technical results.
• Development scope: include senior individual contributors and team leads, not only people managers.
• Succession: if leadership lives in several people, one departure leaves a smaller gap.
• Measurement: track behaviors that show direction, alignment and commitment, not only completion of a program.

HR and L&D teams that want outside support can look at leadership coaching for companies, which covers 1:1 coaching and manager workshops.

How to Build Leadership Across a Team or Company

Use this five-step rollout to move from “we need better leaders” to “we need leadership everywhere.”

1. Define it in behaviors. Write five or six observable behaviors, using direction, alignment and commitment as the frame. “Explains how this quarter’s goal connects to the company plan” is observable. “Shows vision” is not.
2. Diagnose before you train. Run the team exercise below with three or four teams. The gaps show where to spend budget.
3. Give practice, not only content. Assign real stretch work: lead a cross-team project, run a retrospective, own a rollout. Pair it with guidance on leading a team through change.
4. Coach new managers early. The first year in a people role sets habits. Structured first-time manager coaching closes the gap between authority and skill.
5. Measure behaviors. Add two or three behavior-based items to pulse surveys and 360 feedback. Review them when promotion decisions are made.

A 20-Minute Team Exercise

Ask each team member to answer three questions privately, then compare answers aloud. This is a PathWise adaptation of the DAC model, not a validated assessment.

• Direction: “In one sentence, where is this team going this quarter?”
• Alignment: “Which two handoffs slow us down most?”
• Commitment: “What would I give up to make the team’s goal succeed?”

Mismatched answers to the first question signal weak direction. Repeated handoff complaints signal weak alignment. Vague or defensive answers to the third signal weak commitment. Pick one gap and agree one fix.

Manager Checklist: Is There Leadership on Your Team?

• Can each person on the team state the goal in one sentence?
• Does the team decide anything without you in the room?
• Does a person without a title lead part of the work?
• Do people know whom to ask when priorities clash?
• Would the team keep moving for two weeks if you were away?

Two or more “no” answers mean you have a leader and not yet leadership.

Traits and Behaviors of Effective Leaders

Traits matter when they show up as behaviors. Seven appear most often, and each has a visible form:

• Vision: describes where the team is headed and why it matters.
• Communication: explains decisions and listens before responding. See the communication skills leaders rely on.
• Integrity: does what was promised and owns mistakes.
• Empathy: notices when someone is struggling and adjusts the workload or the support.
• Decisiveness: decides with incomplete information and explains the reasoning.
• Adaptability: changes course when facts change.
• Supportiveness: removes obstacles and gives credit.

For a longer breakdown, read the twenty leadership qualities that define a good leader.

How to Grow as a Leader

Leadership development begins with self-awareness, according to CCL, and it is tailored to the person. These six steps work for individuals at any level:

1. Ask for specific feedback. Request one example of when you helped or hindered the team’s direction.
2. Practice in small stakes. Lead a meeting, a pilot or a handoff before leading a department.
3. Learn from people who lead well. Notice what they do in tense moments, then try one habit.
4. Build emotional intelligence. Pause before reacting and name what the other person likely needs.
5. Delegate with a purpose. Give others ownership of outcomes, not just tasks.
6. Keep learning. Read, take courses and review your own decisions each quarter.

Leadership Is a Capability, Not a Title

A title tells people who is responsible. Leadership tells them where they are going. Companies that treat the two as one buy leaders and hope. Companies that separate them build habits and measures that outlast any single manager. The question to ask of any team is not “who is the leader?” but “is leadership happening here?”

How PathWise Helps Teams Build Leadership

PathWise supports HR and L&D teams that want to build leadership across managers, not only promote leaders. PathWise corporate programs include:

• Manager and leadership workshops: live sessions on manager skills, team communication and decision-making, in person or virtual, tailored to your teams.
• 1:1 leadership and management coaching: support for first-time managers, rising leaders and senior executives.
• Custom leadership development: multi-part learning journeys and manager tracks, plus a Manager Development Program.

If your team has leaders but not yet leadership, start with the exercise above and bring the results to a conversation about where a program should begin.

Works Cited

• McCauley, Cindy, and Lynn Fick-Cooper. “What Is Leadership? A Definition Based on Research,” Center for Creative Leadership, March 15, 2026. https://www.ccl.org/articles/leading-effectively-articles/what-is-leadership-a-definition/
• Bouttell, Laura, Quarterdeck, “Leadership vs Leader: Understanding the Crucial Distinction,” Quarterdeck, December 30, 2025. https://quarterdeck.co.uk/articles/leadership-vs-leader/

Communication skills activities are short, structured exercises that let a team practice one skill at a time, such as listening, giving clear instructions, or handling a hard conversation. A manager runs the exercise, the group debriefs what happened, and people then repeat the new habit in real work. Most fit inside a regular team meeting.

These communication activities for adults suit the workplace, so each one lists group size, time, materials, steps, debrief questions, the skill it builds, and a remote or hybrid variant. Pick one, run it this week, and adjust.

What Are Communication Skills Activities?

The most useful activities in communication training share four parts. Without all four, an exercise is entertainment, not practice.

• Constraint: A rule that creates friction, such as no gestures, no questions, or a 20-word limit.
• Task: A short job the group must finish under that constraint.
• Debrief: Guided questions that explain why the task went well or badly.
• Transfer: One real conversation, message, or meeting where each person applies the skill before the next session.

Communication Skills Games vs. Communication Exercises

People search for communication skills games and communication exercises as if they were the same thing. The difference is stakes. A game, such as Broken Telephone, is playful and low risk, which helps a new team loosen up.

A communication exercise uses realistic work content and asks for a change in behavior. Adult teams usually need a game to warm up, then an exercise to build the skill. The eight activities below lean toward exercises.

Which Communication Activity Fits Which Team Problem?

Match the activity to the symptom you see, not to what looks fun.

• Unclear handoffs and briefs: Back-to-Back Drawing and Headline First.
• People talking past each other: Listen, Summarize, Confirm.
• Projects drifting from the plan: Assumption Swap and Meeting Recap Relay.
• Tense feedback or avoided conversations: I-Statement Rewrite and Difficult Conversation Triads.
• Chat messages that read as sharp or vague: Written Tone Audit.

How to Run Communication Activities at Work

Managers are stretched. Gallup’s 2026 workplace report, as summarized by UNLEASH, found that manager engagement has dropped from 31% in 2022 to 22% in 2025. A half-day workshop is rarely realistic for that audience. A 20-minute exercise in an existing weekly meeting is.

Communication skills group activities work best when the manager follows the same five steps every time. Consistent steps let the team focus on the skill, not the format.

1. Name one skill. Tell the team what you are practicing, for example “checking understanding before we act.”
2. Set ground rules. Keep scenarios fictional, let people opt out of any role, and state that nothing said in the exercise feeds a performance review.
3. Run short rounds. Two or three rounds of five to ten minutes keep energy up and let people improve on the second pass.
4. Debrief in order. Ask what happened, why it happened, and what each person will do differently on Monday.
5. Assign the transfer task. Each person picks one real message or conversation to apply the skill to before the next session.

Choose formats everyone can join. Skip blindfolds and physical contact if they exclude anyone, offer an observer role, and give non-native speakers a minute to prepare.

Communication Skills Exercises for Teams: 8 Activities With Steps and Debriefs

Each exercise below is written so a manager or L&D facilitator can run it with no prep beyond printing a card or opening a shared document.

1. Back-to-Back Drawing

• Skill built: Giving clear instructions and checking that they landed.
• Group size: Pairs, any even number. Add an observer to an odd group.
• Time: 15 minutes.
• Materials: Paper, pens, and one simple drawing per pair made of six to eight shapes, lines, and arrows.
• Steps: Seat each pair back to back. The speaker describes the drawing without naming the overall shape or using gestures. The partner draws and may not ask questions. Compare the result with the original. Swap roles with a new drawing, and this time allow questions.
• Debrief questions: What did you assume your partner could picture? Which instruction caused the biggest miss? How much did questions improve accuracy? Where do we give one-way instructions at work, such as tickets, briefs, or handoffs?
• Remote or hybrid variant: Send each speaker the image by private message. Drawers draw on paper off screen and hold it to the camera at the end. In hybrid teams, pair a remote person with an in-room person so both use voice only.

2. Listen, Summarize, Confirm

• Skill built: Active listening and paraphrasing.
• Group size: Pairs, or triads with one observer.
• Time: 20 minutes.
• Materials: A timer and a list of real but low-stakes topics, such as “a deadline I am worried about.”
• Steps: The speaker talks for three minutes. The listener gives no advice. The listener then summarizes in 30 seconds, starting with “What I heard is.” The speaker corrects anything missed and rates accuracy from 1 to 5. Swap roles.
• Debrief questions: What were you doing in your head while the speaker talked? What did the summary leave out? How did it feel to be summarized accurately? Which meetings at work skip this step?
• Remote or hybrid variant: Use breakout rooms of two with cameras on. The observer posts one missed detail in chat. In hybrid teams, keep each pair in the same mode so nobody is half-heard through a room speaker.

3. Assumption Swap

• Skill built: Surfacing hidden assumptions and aligning on scope.
• Group size: A team of 5 to 12 working on the same project.
• Time: 25 minutes.
• Materials: Sticky notes or a shared board, and the current project brief.
• Steps: Each person silently writes three assumptions about scope, owner, deadline, or customer, one per note, over five minutes. Post all notes and cluster matching ones. For each cluster, ask who believes it and who does not. Assign an owner to confirm every disputed assumption.
• Debrief questions: Which assumption surprised you? Which would have cost the most if left unspoken? What belongs on our kickoff checklist now?
• Remote or hybrid variant: Use a digital board with anonymous notes. In hybrid teams, have everyone, including in-room staff, write on the board so remote voices carry equal weight.

4. I-Statement Rewrite

• Skill built: Assertive, non-blaming feedback. This sits between passive communication skills and aggressive blame.
• Group size: Pairs or triads.
• Time: 25 minutes.
• Materials: Four blame-heavy statements on cards, such as “You never update the tracker.”
• Steps: Each person rewrites every card in this frame: “When [observable fact], the impact is [result], and I need [specific request].” Pairs read the rewrites aloud. The listener paraphrases and names the part that sounded most like a fact. Swap and refine.
• Debrief questions: Which words triggered defensiveness? Where did you slip into opinion? Was your request specific enough to answer yes or no?
• Remote or hybrid variant: Draft privately in chat, then speak the rewrite in a breakout room. Hybrid teams can run it unchanged.

5. Difficult Conversation Triads

• Skill built: Staying calm and curious under pressure.
• Group size: Triads with a speaker, a responder, and an observer.
• Time: 40 minutes: three rounds of eight minutes plus a debrief.
• Materials: Scenario cards (a missed deadline, pushback on scope, a request to take on extra work) and an observer checklist covering tone, questions asked, and escalation.
• Steps: The speaker raises the issue using the I-statement frame. The responder replies as a realistic colleague. The observer notes tone and any moment of escalation, then gives two specific observations. Rotate roles. Use fictional scenarios only.
• Debrief questions: Which phrase lowered the temperature? Where did the conversation escalate, and why? What will you try in a real conversation this week?
• Remote or hybrid variant: Run triads on video calls even for people in the same office, so everyone hears the same audio. The observer keeps notes in a shared document.

6. Headline First

• Skill built: Concise, conclusion-first messaging.
• Group size: 6 to 20 people, working in pairs.
• Time: 15 minutes.
• Materials: A timer and paper or a chat window.
• Steps: Everyone writes a three-sentence update on current work. Rewrite it as one sentence of 20 words or fewer that opens with the decision or request. Read it to a partner, who answers “What do you need from me?” The pair edits until the answer is clear.
• Debrief questions: What did you cut? Did your request survive the edit? Which updates did we receive last week that needed this treatment?
• Remote or hybrid variant: Everyone posts their one-liner in chat at the same moment, and the group reacts to the clearest. For different time zones, record 60-second voice notes and review replies the next day.

7. Meeting Recap Relay

• Skill built: Shared understanding of the decision, the owner, and the next step.
• Group size: 4 to 10 people.
• Time: 15 minutes.
• Materials: A short case card describing a low-stakes decision, such as choosing a vendor or setting a release date, and a timer.
• Steps: Hold a five-minute discussion on the case. One person recaps the decision, owner, and deadline in 30 seconds. A second person restates it in their own words. Capture the differences, agree on one final sentence, and post it.
• Debrief questions: Where did the two versions diverge? What had everyone assumed was obvious? What recap format should we adopt in real meetings?
• Remote or hybrid variant: Each person types a private recap in chat and sends it on a countdown so nobody copies. In hybrid teams, ask the remote participant to recap first.

8. Written Tone Audit

• Skill built: Clear, well-toned written messages. Pair it with written communication skills for deeper practice.
• Group size: Individual work, then pairs. Any team size.
• Time: 20 minutes.
• Materials: Three anonymized messages from your team channels (with permission) or sample messages that are vague or sharp, and a shared document.
• Steps: Read each message as the receiver, not the sender. Mark words that sound sharp, vague, or unclear about ownership. Rewrite the message. Compare rewrites with a partner and decide which messages should have been a call.
• Debrief questions: Which single word changed the tone most? Which message should have been a conversation? What is our norm for switching to voice?
• Remote or hybrid variant: This activity already fits remote work. Use comments in a shared document, and give remote staff the same access as in-room staff.

Adapting Communication Activities for Remote and Hybrid Teams

The per-activity variants above cover the mechanics. Four habits keep any session fair across locations:

• Same channel for everyone: If one person is remote, everyone joins the video call, even from the same room.
• Small breakouts: Keep rooms to two or three people. Larger rooms let quiet people disappear.
• Written first: Collect ideas in chat or a board before discussion, so speaking order does not decide whose ideas count.
• Asynchronous option: For teams across time zones, use voice notes or a shared document and hold the debrief live in one short call.

How to Tell Whether the Activities Are Working

Pick two observable signals before you run these communication skills activities. Good candidates are the number of “what did you mean?” follow-up threads, rework requests on handoffs, and recap mismatches in meetings. Count them for two weeks, run six sessions, then count again. Add a five-question pulse survey and a check-in during one-on-ones.

If you want a facilitator to run these sessions or build them into a wider manager development plan, PathWise offers team communication workshops in person or virtually.

When Communication Activities Are Not Enough

Communication skills activities build habits. They do not replace a planned program with learning objectives, a budget, and an owner. If you are designing that, read communication skills training for employees. For deeper work on conflict, rapport, and empathy, see interpersonal communication training. To understand the skill framework behind these exercises, start with effective communication skills.

How PathWise Helps Teams Build Communication Skills

Exercises stick when someone owns the follow-through. PathWise works with companies on team workshops, manager and leadership coaching, soft skills training, and custom programs. If handoffs, feedback, or meetings keep breaking down in the same places, explore PathWise corporate training and workshops to plan a communication session built around your team’s real work.

Works Cited

• Brazier, John, “Gallup’s State of the Global Workplace 2026 Report: Three essential actions for HR leaders,” UNLEASH, April 10, 2026. https://unleash.ai/strategy-and-leadership/gallups-state-of-the-global-workplace-2026-report-three-key-decisions-for-hr-leaders

Communication skills training for employees is a structured program that teaches staff to listen, explain, give feedback, and handle hard conversations at work. The strongest programs match skills to each role, build in live practice instead of lectures, and track changes in on-the-job behavior rather than course completion alone.

For HR and learning and development (L&D) leaders, the real work is choosing what to train, in which format, for whom, and how to prove it worked. This guide covers skills by role, format options, needs assessment, measurement, build versus buy, and the questions to ask any provider before you sign.

Why Does Communication Training for Employees Matter?

Communication training matters because team outcomes run through managers, and managers are less engaged than they were four years ago. Gallup reports that managers account for 70% of the variance in team engagement. The same page cites Gallup’s State of the Global Workplace 2026 report, which found global manager engagement fell from 31% in 2022 to 22% in 2025.

Clarity is where the damage shows first. In Gallup’s U.S. data for the third quarter of 2026, 46% of employees strongly agreed they know what is expected of them. The high was 61% in 2015. Expectations are set in conversation, so this gap is a communication skill problem, not only a process problem.

That framing changes how you buy employee communication training. A course people enjoy but never apply produces no return. Each section below ties a training choice to a behavior you can observe and measure.

Which Communication Skills Should You Train for Each Role?

Train different skills at each level: clarity and listening for frontline staff, feedback and expectation setting for managers, and narrative and change communication for senior leaders. One curriculum for everyone wastes time, because a service agent, a first-time manager, and a vice president face different communication moments.

Frontline Employees and Individual Contributors

Frontline communication is mostly about accuracy and speed under pressure. Focus on five skills:

• Active listening: paraphrasing what was said, asking clarifying questions, and confirming next steps before a conversation ends.
• Written clarity: emails, chat messages, and handoff notes that state the ask, the owner, and the deadline in the first two lines.
• Assertiveness: raising a blocker, declining extra work, or disagreeing with a peer without aggression or silence.
• De-escalation: staying calm with an upset customer or coworker, naming the issue, and offering a concrete next step.
• Meeting participation: arriving with a point of view and leaving with a clear action item.

Teams that need deeper work on the relational side can pair this with interpersonal communication training.

People Managers

Managers carry the most leverage, so give them the broadest toolkit:

• Giving feedback: specific, timely, and tied to a behavior and its impact. The art of feedback covers the core techniques.
• Setting expectations: stating the outcome, the standard, and the deadline, then checking understanding by asking the employee to restate it.
• One-to-one conversations: using a consistent agenda, asking coaching questions, and leaving space for the employee to talk first.
• Difficult conversations: performance issues, conflict between teammates, and bad news.
• Communicating change: explaining what is changing, why, and what stays the same, then listening for concerns.

Frequency matters. Gallup reports that employees who get daily feedback from their manager are three times as likely to be engaged as those who get it once a year or less.

Senior Leaders

Leaders communicate through other people, so message quality has to survive several layers:

• Narrative and storytelling: explaining strategy and trade-offs in a story people can repeat accurately.
• Cascading messages: equipping managers with the same talking points, then checking what arrives at the front line through skip-level listening sessions.
• Listening up: building channels where bad news reaches the top early.
• Change and crisis communication: town halls, Q&A formats, and tone under pressure.

For a fuller treatment of this level, see this guide to leadership communication skills.

Which Training Format Fits: Workshops, Coaching, Cohorts, E-Learning, or Lunch-and-Learns?

Match the format to the outcome. Workshops and cohorts build behavior through practice, coaching fixes individual blind spots, and e-learning and lunch-and-learns raise awareness at low cost. Five formats cover most needs:

• Live workshops: facilitator-led sessions with role plays built from your real situations. Communication workshops for employees suit teams that share a specific problem, such as unclear handoffs. A single session fades without follow-up.
• One-to-one coaching: best for managers and leaders with individual blind spots or a high-stakes transition. It costs more per person and does not scale to a whole workforce.
• Cohort programs: groups of about 8 to 15 move through modules over several weeks, practice with peers, and report back on real use. The accountability is the point.
• E-learning and microlearning: self-paced modules in a learning management system (LMS). They give consistency across shifts and locations and work well in onboarding, but they rarely change behavior alone.
• Lunch-and-learns: short, low-cost sessions that introduce a topic or relaunch a program. Treat them as awareness, not skills training.

A practical blend uses e-learning for shared vocabulary, a live workshop for practice, and manager-led follow-up for transfer to the job. For drills to run between sessions, see these communication skills activities.

Hybrid teams need one adjustment. Run live sessions virtually with small breakout rooms, and build scenarios around the channels people actually use: chat, video calls, and asynchronous updates.

How Do You Run a Communication Training Needs Assessment?

A needs assessment compares the communication behaviors each role requires with what people do today, using manager input, survey data, and work samples, so you train only the real gaps. Six steps keep it manageable:

1. Define what good looks like. Write two or three observable behaviors per role, such as “states the ask and deadline in the first message.” Start from the effective communication skills your company values.
2. Pull existing signals. Engagement survey items on clarity, exit interview themes, escalation and rework logs, missed handoffs, and customer complaints already hold evidence.
3. Ask managers and employees. Use short interviews or a pulse survey. Ask for specific recent incidents, not ratings out of five.
4. Sample real work. Score anonymized emails, project updates, or call recordings (with consent) against a simple rubric.
5. Separate skill gaps from system gaps. Training cannot fix unclear priorities, tool overload, or a manager who punishes bad news. Route those issues elsewhere.
6. Set the baseline. Choose the two or three behaviors that matter most and record today’s numbers. You will need them to show change.

How Do You Measure Whether Communication Training Works?

Measure communication training on the four levels of the Kirkpatrick Model: reaction, learning, behavior, and results, with behavior checked at 30, 60, and 90 days after the session.

• Level 1, reaction: ask “How relevant was this to your job?” and “How confident are you to use it this week?” Skip “Did you enjoy it?”
• Level 2, learning: score role plays against a rubric before and after, and add a short scenario quiz.
• Level 3, behavior: use manager observation checklists, 360 feedback pulse items, peer feedback, and samples of written work. Most programs stop before this level, and it is the one that proves transfer.
• Level 4, results: track business measures tied to your needs assessment, such as rework requests, escalations, handoff errors, the clarity item in your engagement survey, and retention on trained teams.

Design for credibility. Record a baseline, and where possible compare a trained cohort with a waitlist group that trains later. Report level 3 and 4 data as contribution, not proof, because other changes affect results too. Your own baseline numbers will hold up in a budget review better than a generic ROI ratio from a vendor deck.

Give every manager a one-page checklist of the target behaviors. Their observations are the cheapest behavior data you will get.

Should You Build Communication Training In-House or Buy It?

Build in-house when you have skilled facilitators, stable content, and an internal-only audience. Buy when you need speed, outside credibility, or practice scenarios run by experienced facilitators. Many HR teams do both.

Build when:

• You have facilitators with time to prepare, deliver, and coach.
• The content depends on proprietary processes, systems, or customer situations.
• You can accept a slower launch while you design and pilot.

Buy when:

• You need to launch within a quarter.
• Leaders will be more candid with an outside facilitator, especially on feedback and conflict.
• You need trained facilitators to run role plays at scale.
• The skill sits outside your team’s expertise, such as storytelling or negotiation.

The hybrid model is often the best fit. Buy the first wave and a facilitator kit, certify internal champions through a train-the-trainer program, and keep reinforcement and measurement in-house. Watch the hidden costs of building: facilitator preparation time, content upkeep, and keeping quality consistent across facilitators.

What Should You Ask a Communication Training Provider?

Ask how the provider diagnoses needs, how much session time is practice, who facilitates, how learning is reinforced, and what behavior data they will report. Use these questions in every vendor conversation about workplace communication skills training:

• Diagnosis: How do you learn about our teams before designing anything?
• Customization: Will scenarios use our real roles, tools, and customer situations?
• Practice share: What portion of each session is practice with feedback rather than presentation?
• Facilitators: Who delivers, and what experience do they have with employees at our level?
• Reinforcement: What happens in the 90 days after the session?
• Reporting: What will you report beyond attendance and satisfaction scores?
• Psychological safety: How do you make it safe for people to practice and get it wrong?
• Scope: What is included in the fee: design, materials, follow-up, and assessment?
• Pilot: Can we run one cohort before committing to the full rollout?

Treat these as red flags: a guaranteed ROI percentage, identical content for every audience, completion-only reporting, no live practice, and no role for managers.

Next Steps: How PathWise Helps Teams

PathWise supports mid-sized companies with live, facilitator-led workshops on team communication, storytelling, and negotiation, delivered in person or virtually and tailored to a team or challenge. Manager development and coaching programs extend the learning past workshop day, so new habits reach daily work.

Start small: choose one role group, set a baseline for two or three behaviors, and run a pilot cohort before you scale. To plan that pilot, talk with PathWise about team training.

Works Cited

• Gallup, “How Leaders Can Improve Employee Engagement and Culture,” Gallup, September 21, 2026. https://www.gallup.com/workplace/712895/leaders-improve-employee-engagement-company-culture.aspx
• Gallup, “U.S. Employee Engagement Below 30% for First Time in 15 Years,” Gallup, October 28, 2026. https://www.gallup.com/workplace/716117/employee-engagement-below-30-first-time-years.aspx

Interpersonal skills training teaches people to listen closely, show empathy, handle conflict, give feedback, and work well with others. It relies on practice, not lectures, so that real conversations at work change.

It suits new managers, cross-functional teams, and client-facing staff. Workshops, coaching, and courses each fit a different goal.

What Interpersonal Skills Training Covers

Interpersonal skills are the behaviors that shape one-to-one and small-group interactions. Training breaks them into parts a person can rehearse, observe, and improve. Providers also call it interpersonal communication skills training, interpersonal communication training, or people skills training, and the content is similar. Most programs cover six areas.

• Active listening: Hearing the full message before replying. Learners practice paraphrasing, open questions, and reading nonverbal cues such as tone and body language.
• Empathy: Reading how others feel and responding with care while staying on task. This builds on emotional intelligence, including self-awareness and emotional regulation.
• Conflict resolution: Naming a disagreement early and separating the person from the problem. Learners compare responses such as avoiding, compromising, and collaborating, the range described in the Thomas-Kilmann conflict modes.
• Feedback: Describing a specific behavior and its impact, then agreeing on a next step. The Situation-Behavior-Impact format is a common structure.
• Influence: Winning agreement without formal authority through clear requests, shared goals, and assertiveness. Negotiation practice belongs here.
• Collaboration: Setting working agreements, sharing context across functions, and building psychological safety so people raise problems early.

Interpersonal training is narrower than a general communication program. It centers on relationships, not presentations, writing, or company-wide messaging. For that wider design, see this guide to communication skills training for employees.

Why Interpersonal Skills Matter for Teams

Managers sit at the center of most workplace relationships, and many are stretched. Gallup’s 2026 State of the Global Workplace report puts global manager engagement at 22%, down nine points since 2022 (Gallup). Gallup does not link the drop to training. The figure still matters, because managers carry the daily listening, feedback, and conflict conversations that this training targets.

Early-career talent shows a similar gap. In a May 2026 release on job readiness, the National Association of Colleges and Employers reported that employers rank communication and teamwork among the most important skills for new graduates, yet are less impressed with graduates’ communication (NACE). Those graduates become your first-time reports and team members.

Who Needs Interpersonal Skills Training Most

Start with the roles where one weak conversation costs the most.

• New managers: They move from peer to boss overnight and must set expectations and give feedback. This guide to first-time manager coaching shows how HR can structure that support.
• Cross-functional teams: Product, sales, and operations groups hold different priorities and vocabularies. Training gives them shared working agreements and a method for settling trade-offs.
• Client-facing staff: Account managers and support teams need empathy, de-escalation, and clear expectation-setting under pressure.
• Hybrid and distributed teams: Fewer hallway conversations mean misreadings last longer. People need explicit habits for check-ins and for tone in writing.
• High-potential individual contributors: Technical experts moving toward leadership need influence and collaboration skills before they get a team.

Check your own data before you commit budget. Four sources show where the need is:

• Pulse survey comments: Look for repeated themes about unclear expectations, not feeling heard, or friction between teams.
• 360-degree feedback: Look for low scores on listening, feedback, and conflict handling.
• Exit interviews: Note how often people name a manager or colleague relationship.
• Escalation and rework logs: Count issues that a direct conversation should have settled.

Interpersonal Skills Training Formats: Workshop, Coaching, or Course

No single format fits every goal. Match the format to the behavior you want to change.

• Workshop: A live cohort session, in person or virtual, with role-play and discussion. Best for building a shared language across a team. Skills fade without follow-up practice.
• Interpersonal skills coaching: One-to-one sessions tied to real situations, such as a tense stakeholder or a team conflict. Best for managers and senior leaders. It takes more time per person and scales slowly.
• Interpersonal skills course: Self-paced modules with scenarios and quizzes. Best for a consistent baseline across many employees. It gives little real-time feedback on live behavior.
• Blended program: A workshop to start, a course for reinforcement, and coaching for those who need more. This design covers each format’s weak spot.

PathWise delivers workplace communication training as live workshops, one-to-one coaching, self-paced courses, and custom multi-part programs, so teams can mix formats.

Sample Interpersonal Skills Training Curriculum

This six-week cohort suits a group of 12 to 20 people. Each week pairs a 90-minute live session with a 15-minute practice task on real work.

• Week 1, Active listening: Practice paraphrasing and open questions in pairs. Task: use one paraphrase in three live conversations and note the result.
• Week 2, Empathy and self-regulation: Identify personal stress triggers and practice naming emotions without escalating. Task: log one tense moment and the different response you tried.
• Week 3, Feedback: Role-play the Situation-Behavior-Impact format, using the steps in giving productive feedback. Task: deliver one piece of feedback and ask for one.
• Week 4, Conflict and difficult conversations: Map conflict styles, then rehearse an opening line for a real disagreement. The scripts in dealing with difficult coworkers help here. Task: hold the conversation you have been delaying.
• Week 5, Influence and assertiveness: Practice making a clear request, stating a boundary, and handling pushback. Task: make one request using three parts: the ask, the reason, and the next step.
• Week 6, Cross-team collaboration: Draft working agreements and run a team retrospective on how the group handles disagreement. Capstone: each learner presents one before-and-after example.

For a one-day version, keep weeks 1, 3, and 4 and move the practice tasks into a 30-day follow-up.

How to Make the Practice Stick

Role-play carries most of the learning. Use triads: one speaker, one partner, and one observer who scores the exchange against a short rubric. Rotate roles every round. Ready-made drills are in these communication skills activities.

Add manager support. Each participant’s manager spends ten minutes of the weekly one-to-one asking what was practiced and what happened. Learning transfer to the job depends on that conversation.

How to Measure Behavior Change After Interpersonal Skills Training

Satisfaction scores show whether people liked the session. They do not show whether anyone behaves differently. The Kirkpatrick model gives four levels to track: reaction, learning, behavior, and results.

• Pick two or three target behaviors: Write each so an observer can see it, such as “paraphrases before responding” or “gives feedback within two days.”
• Baseline before training: Collect a 360-degree score or a manager observation on those behaviors.
• Check learning: Use scenario quizzes or a recorded role-play scored against the rubric.
• Re-measure at 30, 60, and 90 days: Ask the manager and two peers to rate the same behaviors, then compare with the baseline.
• Track business signals: Use measures already in your systems, such as escalations, rework tied to handoffs, pulse items on trust and clarity, and regretted attrition on the participating teams.
• Use a comparison group when possible: Teams not yet trained show what would have changed anyway.

Keep claims modest. Behavior ratings move first, team signals follow, and business results take longer and have many causes.

Manager Checklist for the 90 Days After Training

• Ask: What did you practice this week, and what happened?
• Observe: Sit in one meeting and note one target behavior.
• Coach: Give one piece of feedback tied to the rubric.
• Recognize: Name a specific improvement in front of the team.
• Escalate: Tell HR when workload or policy blocks the new behavior.

How to Evaluate an Interpersonal Skills Training Provider

A topic list does not show whether a program works. Ask these questions before you sign.

• Target behaviors: Which observable behaviors does the program change? “Better communication” is too vague to measure.
• Practice time: What share of each session is role-play and feedback, and what share is lecture?
• Your scenarios: Will role-plays use your real situations, such as a missed deadline or a client escalation?
• Facilitator background: Has the facilitator worked with managers and cross-functional teams? Ask to see a sample session.
• Reinforcement plan: What happens in the weeks after the workshop: practice tasks, manager prompts, or coaching?
• Measurement support: Will the provider help you set a baseline and re-measure?
• Certificates: What does the certificate attest to? Attendance certificates confirm presence, not skill.

How to Build Interpersonal Skills on Your Own

You can build these skills without a formal program. The method is the same: practice, feedback, and repetition.

• Ask before you answer: In your next three conversations, ask one clarifying question before you give your view.
• Paraphrase: Restate what you heard in one sentence, then check that you got it right.
• Request feedback weekly: Ask a colleague, “What is one thing I could do differently in meetings?”
• Script one hard conversation: Write the opening sentence, the facts, and the request. Say it aloud once.
• Review each week: Note one exchange that went well and one that did not, and look for the pattern.
• Add outside input: If you cannot see your own pattern, a self-paced interpersonal skills course or a coach supplies the feedback.

How PathWise Helps Teams Build Interpersonal Skills

Interpersonal skills change when training, practice, and manager support line up. PathWise supports that through corporate training for teams and managers: live workshops on communication and negotiation, one-to-one leadership and management coaching, self-paced courses, and custom multi-part programs.

Start by choosing the two or three behaviors your teams most need, then match a format to each. Bring those goals to a conversation with PathWise and design the program around them.

Works Cited

• Gallup, “State of the Global Workplace 2026,” Gallup, 2026. https://www.gallup.com/workplace/349484/state-of-the-global-workplace.aspx
• National Association of Colleges and Employers, “Employers Give New College Grads a Passing Grade on Job Readiness,” NACE Press, 28 May 2026. https://naceweb.org/about-us/press/2026/employers-give-new-college-grads-a-passing-grade-on-job-readiness

What happens when the strengths that made you successful become the very things holding you back?

You’ve worked hard, built your career, and earned greater responsibility. But now something isn’t working. Your team isn’t responding the way you’d hoped. Your leadership style feels less effective. Or perhaps you’ve hit a career plateau despite doing everything that made you successful in the past.

The problem may not be your skills or experience. It may be that the leadership habits and behaviors that got you here are no longer what you need to move forward.

In this episode of Career Sessions, host J.R. Lowry talks with Andrea Petrone, executive coach, leadership advisor, and author of Reinvention at the Top: The Playbook for CEOs to Lead Under Pressure, about why successful professionals get stuck, and how to reinvent yourself as a leader without losing your authenticity.

Drawing on his own experience as a young CEO and his work coaching senior executives, Andrea explains how our greatest strengths can become liabilities, why we revert to ineffective leadership behaviors under pressure, and how to recognize when it’s time to change.

Andrea’s lessons are relevant well beyond the C-suite. You’ll learn:

Why success can become a trap: How the strengths and leadership habits that helped you advance can eventually limit your effectiveness.

• How to recognize when your leadership style isn’t working: The subtle warning signs that your team may be disengaging, withholding feedback, or losing confidence.
• Why your past influences how you lead: How childhood experiences, former bosses, and early career lessons shape your leadership instincts, especially under pressure.
• How to lead with greater authenticity: Why trying to project confidence and authority can undermine your effectiveness, and how quiet leadership can build trust and influence.
• How to reinvent yourself without putting your career on hold: Practical steps to question old assumptions, change ingrained behaviors, and develop a leadership approach that fits your current responsibilities.

Whether you’re a new manager, an experienced executive, or a professional preparing for your next career move, this conversation offers a practical approach to leadership development, career growth, self-awareness, and personal reinvention.Because sometimes the biggest obstacle to becoming a better leader isn’t what you don’t know. It’s what you need to unlearn.

About the guest: Andrea Petrone is an executive coach, leadership advisor, and author of Reinvention at the Top. He works with CEOs and senior leaders to help them navigate change, lead under pressure, and develop more authentic and effective leadership approaches.

Learn more about Andrea’s work and access his leadership assessment at reinventionatthetop.com.

And be sure to check out my forthcoming book, written with Daniela De Luca, Be the Boss You Wish You’d Had: A Preople-First Guide to Management, available for pre-order wherever you buy your books. For more info, visit, https://pathwise.io/be-the-boss/

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/andrea-petrone/.

Watch the episode here

Listen to the podcast here

When Your Strengths Become Weaknesses: How To Reinvent Yourself As A Leader with Andrea Petrone

Featuring Andrea Petrone

How Strengths Can Become A Ceiling For Senior Leaders

There’s a familiar saying in the business world that what got you here won’t get you there. What if the level of change goes deeper than just learning a few new skills? What if the very qualities that have made you successful, things like your drive, your confidence, and your determination, start to become things that hold you back? What if somewhere along the way you become so focused on being the leader that you think you’re supposed to be that you lose touch with the person that you actually are?

My guest is Andrea Petrone, an executive coach, leadership advisor, and author of Reinvention at the Top, the playbook for CEOs to lead under pressure. Drawing on his own career setbacks and his work with hundreds of senior leaders, Andrea argues that leadership problems often aren’t about a lack of competence. They’re about the gap between who we are, what we stand for, and how we show up under pressure.

We are going to explore how success can become a trap, how childhood experiences can shape our leadership instincts, why authenticity becomes harder the further we advance, and how to reinvent ourselves when the old playbook stops working. Now, while Andrea writes for CEOs, these lessons matter to anyone who is stepping into a bigger role or even into the next chapter of their careers more generally, because sometimes what got you here won’t get you there. Let’s get into the discussion with Andrea.

Thanks so much for joining me and looking forward to having you on the show.

Thank you so much, J.R., for inviting me to your show. Looking forward to this conversation.

Let’s get into it. You’ve got a new book out in which you argue that the strengths that have made us successful can eventually hold us back. How does that happen?

The through line, or the story of this book, is what I noticed and observed, J.R., over many years. First of all, from myself, because I was a CEO at 35 years old. I went through this. In a number of conversations I had on my show, The World Class Leader Show, where I interview CEOs, but equally in my coaching conversations with CEOs. What I started to realize very quickly is that when you get to the top, and by the way, you do not need to be SEO to experience that. It could be at the top table or could be in any table where you have an important role or responsibility.

What I realized is that what got you there is valid because you deserve it. You’re good at what you do, meaning your strengths relate to your question. A strength gets really rewarded so often it hardens into your identity, who you really are, and it stops being a choice and starts running you. You’re starting to become like a victim of your own strengths because those strengths work so well for you and with you. You start considering who I am. These are the strengths that got me so far. Why should I change it? Why should I reconsider that? Something happens. The role changes.

When I say role changes, it doesn’t necessarily need to be a kind of new assignment or new appointment. When I say role changes, it could actually happen even when you are in the same title. Something shifts around you. The context, the people, the ownership, the team that you are working with, the model, the business, the acquisition, merger, whatever happens. As we know now, there actually is quite a frequent number of changes that happen. What one needs speed and decisiveness now may be patience and letting others decide. The reflex, if you like, stays the same.

What I think is interesting to consider is that sex removes the feedback they’re used to, correcting you somehow. People tell you maybe less, the truth, the higher you go, so you do not feel that drift. Your greatest strengths, overused and unexamined, become your ceiling. That’s what I’ve seen multiple times. It’s what I call your past identity, your past playbook. In this book, I invite you to consider that entity, that strength, at some point, might not be anymore in service of what you’re dealing with.

You had your own experience with this, that you talk about a quick rise and then some setbacks. Talk about what that felt like for you when you had that realization that what was working for you in the past wasn’t necessarily working for you in your present at that point.

Reinvention At The Top: When a strength gets rewarded so often, it hardens into your identity, who you really are, and it stops being a choice and starts running you.

I’m probably the best example. It’s so funny because I started to write this book, thinking about this book way, way later in my journey. When I then reconnected all the dots, I said, “That actually happened to me first.” It’s interesting in terms of retrospective. I was probably one of those guys who had the opportunity to have an international career. As we know, having an international career is often, if you play well, your career is always a good trampoline.

It’s a great opportunity to accelerate your development, your journey, and your growth. That happened to me. I got to the point where, in a matter of a few years, I had growing responsibility almost every single year. We were very fast. I got to a moment where I got to the top of the table. At that time, the table was a joint venture, so I was not leading McDonald’s, but it was still a very important role for me as a newcomer at the top. What I realized is that I learned something from the past, from what works, what doesn’t, from mentors, from previous bosses, from clients.

You started to experience what leadership is supposed to be through the lens of your experience. Equally through the lens of your education, through the lens of your values, through the lens of the books that you read. It’s all part of the mix. Now, I came into that role with a very clear idea of what I was going to be in that role. I need to control what’s happening. I need to direct people. I need to give instructions. I need to jump on things.

Now, there are still many leaders. They’re actually leading that way. It’s nothing right or wrong. What I experienced is that, in that role, the company needed somebody else, needed an orchestrator, needed a facilitator. I needed to come with humility. I needed to come with more of myself rather than using the title, using a mask to project a level of confidence or authority that was not needed. In the end, eventually, actually, it hurt me.

Recognizing When The Old Playbook Fails And Seeking Guidance

How did you come to that realization? Did you come to it on your own, or did you come to it with help from others?

No, that’s why I think this book could be very relevant, J.R., because it’s not something that happened that I realized was happening to me. I couldn’t name it. I knew something was off. The only way for me to fix it was, “Andrea, go back to the playbook. The playbook works and always works in a certain way. Double down, push harder, do better, just do better.” That was not the answer. The answer was different.

The only answer, as for many of us who have maybe experienced coaching in our experience, in our journey, I decided for the first time to hire a coach. For me, it was, at that moment a setback. Why do I need a coach? I’ve been successful so far. Why is that? Why are you thinking about having a coach? That was, for many, an experience because actually I had a career coach, as I thought that was just a strategic conversation to have for my career. It ended up to be a completely different journey because she helped me to look at the mirror and that was the moment of breakthrough.

I said, “I do not think I’m the person who I really want to be.” From that realization, I started to ask a lot of questions, who do I want to be? What kind of a new identity do I want to create for myself? What is needed inside of what I’m committed to right now? That shifted everything, as you might imagine. I recreated my own story. I recreated my own narrative. Most of all, I recreated myself. Is a reinvention, which is also the title of the book, Reinvention at the Top. That, if you like, is the second part of my career that really started.

You’ve talked about a couple of different things. The fact that the situation that you were in did not need the kind of CEO that you were at that point. You needed more of a facilitator and an orchestrator. You’ve also talked about the fact that you came to this realization that you were not really being the person that you wanted to be. Did you come to those realizations at the same time, or did you come to those realizations separately?

I do not think it is a click. It’s not something that clicks in that moment. It’s a journey that you’re going through. At least I went through. At the beginning, it was, first of all, the realization that something was off, as we said. Second, there was a version of me that was not connected internally. It was a mismatch between what I really think I was, my core values, and the person that was present with people. That was one moment. The second moment was probably more about the fact that I started to question a number of things I thought were true about leadership.

That was difficult because I realized that there was a time when I said, “Am I really willing to let some of the things I know about leadership go?” That was not easy because, especially if you consider yourself a successful individual, the last thing that you are open to doing is get rid of something coming from your past. Because at that time, you can see that it is the truth. That’s how things work. To me, that was a big moment. I need to let go of a number of things. That was the second moment.

The third moment, which was more deliberate, more creative, was what kind of leader do I really want to be? What is a different version? It’s not one moment. Going back to your question, it’s more about a moment of breakthrough that happens over time. That’s why it’s important. The work I introduce in this book about identity, because it’s quite pointless from experience. Fixing what you say, fixing how you show up, because they come at the end of the process, much more intimate.

It’s more really about you, who you are, your identity, who you want to be. Most of the coaches and most of the leadership development experience, J.R., in my experience, they tackle just marginally what’s going on in people because they tend to tackle the superficial element of that, meaning the behaviors. You’re not going through the identity work. It’s very difficult to make a huge difference in people.

You argue in the book that getting to that identity work often requires looking at your childhood and early experiences that shaped you and even some of your early career. How have you seen that play out with some of the senior executives that you’ve interviewed on your show or worked with? How did you see it playing out in yourself?

Uncovering Origin Identity And Inherited Leadership Defaults

The good news is what I talked about, the different identities, applies to all levels. It’s not, by the way, something that only happens to your manager or middle manager or CEOs. It happens to everybody because we are human. That is a great thing about all of us, that we have one thing in common. We are all human. What I think is interesting from my observation, J.R., is all of us, we have an inherited script and normally come from family, come from education, from values, from early experiences in company and organization, cultural corporate survival. They get installed very early.

Maybe they got awarded, and they turned into an automatic for us. That’s what I was referring to before, an autopilot. Under pressure, what I notice is that default takes over. When you even try to do something different, the context shifts, and maybe you’re thinking of doing something different. When the pressure hits, which is the point of the book, we tend to go to that default. To that inherited script that we had. The other comes from the very early, the beginning, what I call the origin identity in the book, or comes from a little bit more immediate experience, which is called the achieved identity. That’s more in the professional environment.

Regardless, that’s normally what we default to. That’s interesting because you do not choose it. That default, that identity, chooses you because that is the way inside of your mind how things should be run. Now, the freedom is that moment. The realization is, I do not want to be led by that. I do not want to be led by my past identity. I want to create something different. Sometimes people are either not aware of it, or maybe they are, but maybe they’re scared to embrace a different version than said. It’s a moment of truth. The moment of truth normally happens more frequently when you are aware, and second, when the pressure hits hard.

If you feel like you’re in one of those situations where you’re experiencing pressure and things are breaking down, how do you rationalize what you’re observing in yourself versus what you think you should be doing in terms of then course correcting?

The signals to me, there are so many, and what I find particularly interesting is the tangible signal always coming quite late. These are signals related to the performance results matrix. As we all know, that is not necessarily something that you see tomorrow morning. You might see it maybe in three months’ time. That’s not helping. What might be more useful is to start reading better what is happening in the moments. You have a meeting with your team and people.

Maybe they have stopped bringing you the truth, or maybe they are stepping back, or maybe they are not engaging in their body posture. Maybe they are not replying anymore to your messages. There are so many signals that you can read from your team, whether you are a CEO, from the board, or from how the chair is dealing with you. Even if you are a director or manager, it’s about how people are experiencing you. That is interesting because it’s not only about what people say, but it’s also about what people do not say.

It’s not only about what people do, but it’s also about what people do not do or stop doing. There are so many interesting factors. They are giving you some sort of indication that something is off. It’s internal, how you feel about yourself, but also in terms of how people experience you. That is not easy to spot unless you have an interest in how people are experiencing you, but also what level of curiosity you have. Are you curious enough to be open to reconsidering what you have been taking for granted about how people behave about you?

When you’re getting all these signals, this is something that I’ve certainly wrestled with in my own journey. How do you determine whether there is a consistency of those signals relative to it just being a quirk moment? You’re getting signals all the time. Many signals. Not all of them have the same meaning.

That is a very valid question. I would definitely look for patterns because one simple or single example might not necessarily be a reason for shifting or changing or reconsidering everything. I would say, honestly, I feel like we have some good indication of what these common patterns are that are surfacing. The question to me is, are you interested in going a little bit deeper and stopping in there and seeing what they really mean? There is one thing that I noticed, though, J.R., is especially when you get closer to the top, unfortunately, start to become your own habit.

One of the worst habits that leaders have is to really stop listening. Especially when you get to the top, you feel like it’s an obligation, given the responsibility you have, to speak more, to intervene more. As soon as you do it, your ability to listen decreases when you’re so focused on yourself in your thinking, in your speaking, in the way you’re behaving. One, you stop listening. Two, you stop really reading things because you are so focused on yourself. It’s a balance. One thing I learned from my own experience. My quality of listening has really changed after that moment.

I was so curious about people and conversations. I do not think a lot of leaders still have the level of curiosity and interest to have very generous and intentional listening when they’re in conversation. When the pressure hits, good luck with that, because the pressure will go back to your default. If you do not already have a strong orientation to people, the pressure will send you back to that survival-protecting mechanism to be the hero, to be the force, to be the driver of everything.

The Power Of Quiet Leadership And Intentional Listening

You make the case for quiet leadership. Is that going to work in all situations or does it only work in a subset of circumstances? I would imagine that there are probably some where you need somebody who’s much more confident and vocal in a moment, certainly, if not more generally.

It’s such a great point. I love to go a little bit deeper into this point because I wrote a number of articles for some magazine about this. I’m a big fan of quiet leadership. I do not know what your experience was when you were a child, J.R., but my experience, by the way, is very common to many people. My dad passed away this year and is clearly top of mind for me. Now in these moments, I actually start to reevaluate some of the things that happened when he was alive, when I was a child. One thing I realized at that time, I felt like it wasn’t missing for him. He was very quiet. He was silent.

He was listening. I think he had things in his mind. He was a busy manager. I have to say, the only time he was speaking, compared to my mom, he said something that landed with me. It was the power of influencing somebody in a conversation with the right things to say at the right time without ever raising their voice or interrupting me. He was really an interesting, quiet leader. He was a little bit introverted there, but that is, to me, slightly different than being introverted. You can be an extrovert being a quiet leader. It’s not a personality trait. It’s a way of leading.

Now, why I’m bringing this example, because I’ve seen a lot of time, a lot of great leaders, they’ve been very quiet. Quiet because they knew how to shift the context in the moment, and that was needed. On the other hand, I see so many leaders keep talking in any circumstances. That message gets diluted. First of all, because it’s repeated, but sometimes, especially when things change, even the quality of the message is not actually so well repeated. It twists it.

Sometimes it’s fluffier, sometimes more direct. Sometimes it projects one thing. Next time it projects something different. I do not believe that strong leadership is associated with being vocal or being a charismatic leader. To me, it’s what you say and how you say it at that moment. That is good news, I think, for many leaders. They consider themselves quiet, but they can really still shape conversation, people, and performance.

I lean toward that style as well and certainly try to ask more questions than make statements. I’m not always perfect at that, but I think you invite others into the conversation when you do that. As with everything else, it’s the power of having a team discover for themselves what really matters versus you having to tell them what really matters. The first is going to be a lot stronger, more effective in the long run. A lot of leaders just feel like they need to be in charge. It works against them.

It does. What I like to say is that, to me, quiet leadership is what I call control power. It’s a power to influence others in a controlled way. Where your emotions are, they are not in the way. By the way, then we can discuss about, but should leaders be showing some sort of emotion? Of course they do. It depends on how and in what context. When is it in a context of being open, transparent, vulnerable? Absolutely, yes. In the context of giving direction, maybe less.

Reinvention At The Top: Under pressure, our default takes over. When the pressure hits, we tend to go to that default, to that inherited script that we had.

The other thing as a distinction, I would say, “I want to believe because I saw that, that a loud leader creates motion.” Motion is not necessarily what we’re looking for. Sometimes what people are really waiting for from a leader is creating cohesion, alignment, a sense of ownership, empowerment, so people can take action. I just invite people to consider that there is a potentially different way of thinking about leadership. On the other hand, let’s not over-rotate it.

The risk is that people are going to stay so silent, maybe not interrupt the conversation, and let things go. This is a negative element of the interpretation of quiet leadership. Let’s clarify. Quiet leadership is not saying what you think, letting things fall apart, or not intervene when there is something that is wrong or that doesn’t work. It’s different. What we’re saying is, do not be noisy. Volume produces noise. Let’s not produce noise. Let’s produce power in a different way.

I want to come back to this idea of identity that you talked about earlier in the conversation. How would I, as a leader at any level, figure out what is an authentic strength for me versus one that I’m just portraying because I think that’s what leaders do? How do you figure out the difference?

That’s normally the work I do with leaders when we do a little bit more inner work when we are together. Honestly, that is something that many people ask me is, are you suggesting that a new identity could potentially undermine your authenticity? Actually, it’s the contrary. Actually, authenticity is going to drive the right identity that is needed in that moment because it is going to reconnect you to who you really are.

That’s why I’m thinking that what normally happens is that if your past identity is driving you, that normally is a reflection of your success, your strengths, your achievements, no matter what is needed right now. Actually, it’s very seldom that it is authentic because that is the mask. That is projected confidence. That is projected leadership. When I work with leaders, almost always I start from there.

What’s your new identity that is creating that moment? If you feel like something is off, then that process, that journey, it really actually has them going back to who they really are and who they want to be in that moment. It’s refreshing, it’s liberating, it’s freedom because people can finally reconnect with who they truly are, who they want to be, so authenticity is a very critical condition to do that work.

Shifting From A Polished Exterior To Authentic Leadership

Can you talk about an example where somebody that you’d worked with went from that polished exterior to having more of a truly authentic persona, including the warts and imperfections, and what that did for them?

I have so many examples you can imagine. I’ll probably give you a couple because they are different and they give you two different lengths. I coached a senior leader. He called me initially for what he thought was a career challenge. He struggled to get promoted. He thought, I’m so good. I provide so many great results, but why does somebody else always get a better job? His first orientation was, okay, the problem is there. It’s not me. It’s there. It’s the environment, it’s the culture, it’s politics. Great. Let’s talk about this.

I did not entertain that perspective because it was interesting to understand what was actually really happening with him. What I realized, actually, is that he had created an identity for himself that was all about success and career. They only happen when I’m able to demonstrate continuously in the environment how good. It was all about projecting. It was about showing, telling, talking, being visible, all of this identity that he created for himself. That’s so interesting because that was his strategy. Let’s talk in that way. That did not land at all. That did not produce any results in his career.

When we start to look at this identity, first of all, he started to recognize that it was something that he inherited from previous bosses because he had seen other people behaving that way. He said, “That is going to work for me too. Let me do it.” That did not work. When we went through the process, he started to create a completely different identity. That was his choice, not mine, of course. He started to create an identity that was more related to, I want to be somebody that can really empower others so people can step up, they can show up the results, and I’m the convener.

It was an easy process for somebody who so much anchored identity in his way of thinking, mindset. I can tell you, J.R., in a matter of weeks, which is the power of this work compared to the traditional leadership development journey. In a matter of weeks, I have actually interviewed people working with him, and they said, “Somebody has to show up to us.” It’s somebody who is really bringing people together. It’s not always the hero. It’s not always the person in front of them. He created space for others. He ended up having new opportunities at his job because people appreciated that identity.

What a great example of how you can shift your narrative, your story, in that way. I have another leader that is different. He’s somebody who learned that numbers win and humanity, empathy, and emotional intelligence do not matter. Giving straight feedback? No, that’s not me. He’s a very interesting leader. He got to the top with that sort of identity. That will work for me. I’ve seen that in the organization. I’m going to be exactly that kind of leader. He tried. It’s an interesting story.

He tried a number of coaches. They tried to work hard on his behaviors. You have to shift this. You have to do this. You have to get more feedback. Nothing actually stuck with him. Why? It’s because the identity work did not happen. In the coaching, he started to appreciate that there was a different type of leader that was needed. Only when he recognized that for himself was he able to embrace a different leadership and then land it.

People around him experienced somebody else. How powerful that could be. Now, J.R., you might think, “It seems very simple.” It’s simple as a concept, but it’s very difficult for some people to embrace it, to embed it in their own thinking, because we have been building this identity for ages, for decades. It’s not an easy change for people to think in a different way about themselves.

I guess another thing that’s on my mind, Andrea, is when you’re going through this process that you talk about, it’s not like you get a timeout and everybody has to hold off until you finish going through this inner work process. You can pick back up leading the organization and delivering results. How do you orchestrate that process, or give us an example of how one of your clients has orchestrated that process of reinventing themselves while dealing with stakeholders, investors, or whoever that wants to continue push every day.

You have to be comfortable staying in the gap for whatever it requires, because you’re right. The identity, the past identity, is still happening in the day-to-day when you have a conversation. Once you start to realize there is a different identity that you start creating, first of all, you are much more engaged. You are much more interested in conversation with people. People started to notice something, but primarily it’s for yourself because you started to reconnect with yourself, which is an important part, if not 50% of the work.

Reinvention At The Top: A loud leader creates motion, but motion is not necessarily what we’re looking for. What people are really waiting for from a leader is creating cohesion, alignment, and empowerment.

However, what I also noticed is try, test, learn, experience. Meaning, what I normally do with people, I do not ask them to rewrite their identity in a closed room for a month and then go back to the organization, “I have a new identity. Let me tell you what my identity is about. What do you think about this?” That doesn’t really work in that way. What does work is to start bringing, for example, what I suggest people do is take the four or five people around you, the people who cheer you, the people who trust you, the people that you are very close to, even could be your boss, by the way.

That is something I always try to see whether it’s possible to do. Go to them and say, “I want to talk with you.” I want to start a conversation about what is important to you. It’s a moment to reset expectations, for example. Let’s talk about the why. I had a number of conversations with people, and I asked something I would like to share. Some why conversation to get connected. In this conversation, you have no idea how powerful it could be for the people that I work with to test and say, “Let me tell you what is now important to me. What is a different leader I want to be because I really worked hard on myself in the last few weeks or whatever.”

Testing New Leadership Habits In A Safe Environment

It’s so interesting because you can test it in your speaking. You can see how people react, and you become much more comfortable. It’s really like rehearsing what you’re really working on. It’s an interesting story, an interesting way to bring it to life in a very safe and limited environment. Before going, for example, to your big team. Maybe if you’re leading a team, let’s wait. Let’s have this conversation first. That normally is really useful because it helps people to tweak, to refine, to have much more clarity in who you are and what you stand for, which is the part of the message, which is the pillar number two of the through line, the methodology in the book.

That is a great way to test it. It’s all about testing some specific habits, behavior that you start practicing in service of that identity and test it again in a safe environment. Maybe next time you’re one-on-one with a team member, say, “Great, now I’m going to do X because that is aligned with my new identity. I want to see how that lands.” It’s a process of testing, trying, refining, failing, trying it again. That is how it works. It’s a process that is required to get the level of transformation, if you want to call it in that way, that is required by the leader.

It takes a lot of courage to do that, even with your trusted, close people.

It does. That’s why some people, they’re not really willing to do it. Again, the default wins. When you are in doubt, where you do not see a reason for it, the default will always win. Once the default wins, look, if it’s going to produce results, great, go back to default. Normally, when we have this conversation with people, they recognize that default is not going to help. Something different is needed. Look, to be fair, I had some experiences where people initially rejected that. They wanted transformation, but they rejected the world.

They said, “Yes, it seems to be a good idea, but I do not know whether I really want to do it or not.” In the end, they changed their mind because they started to see positive traction from making their changes. Sometimes it seems to be a little bit thoughtful, but not by the coach. Thoughtful by themselves because they’re committed to something different. I can guarantee the experience will always be very rewarding and fulfilling for them.

For somebody who’s tuning in or watching the discussion, who senses that their next chapter is going to require some level of reinvention, where would you suggest they start? What would be a concrete action that they should take first?

The first one is going through that process of spending time with yourself, either alone or with somebody that can help you, a sounding board, a coach, a peer, a mentor, whatever is appropriate for you. Do some exercise, do some tests. The test is, who do I think I am as a leader? What do I believe in leadership? What do I take for granted? Great. Once you do that, then start asking the question. Are all of these things in service of what I am dealing with right now? Use the signals that we spoke about to see whether they are connected to it or they’re not.

That is a moment to say, if they’re serving what I’m dealing with, you do not need any reinvention. You’re on the right track. Keep going. If you feel like what you know about leadership is not anymore in service of what you’re dealing with, reinvention can happen at different levels, different layers, and different moments. I went through a reinvention even when I became an entrepreneur. I’m sure that you went through a similar experience yourself, J.R. That is a moment of truth. If you feel like something is needed, then start with that question.

I’m happy to let go of what I used to believe about leadership and what I would be happy to start embracing as my new narrative, my story, my identity for the future. That is the first step that you’re asking for, J.R., more into the book, because the book has a methodology called the through line, where the first part is going through the work of identity. The second part is, what is the message? What are you going to make unmistakable for people about what you stand for on the back of your identity? Finally, the presence, how people will experience you. It’s not your charisma.

It’s not your style. Is what standards you’re setting for yourself or others that are unmistakable for people because you keep repeating the same thing all over the time. It’s a true line. It’s architecture. It’s a way to see at any given time whether you’re in balance or out of balance. In the book, there are a number of sources, and on the website as well, there is a free scorecard you can take. You can see where you’re. By the way, it’s a very deep assessment. It’s not like a marketing tool. You can really play it out and see what potential gaps are. They might give you some indication of what to work on next.

This is launch week for you, right, as we’re recording this?

Yes. The book is out on 22nd of October, 2026.

I’m sure it feels like a big moment to get the book out into the world. I know from my own experience that it’s a very long process, only a small slice of which is actually writing the book.

That’s a completely different journey, as you said, in writing, then bringing to life. There is a moment of excitement because I think there is a story, a message, that is something that I never found in other books. Something was missing from the entire business ecosystem. Very curious to hear, to see how people will apply this. We’re bringing the methodology to a number of organizations as well, because that’s something that is worth bringing to, again, all the CEOs, the executive team, the directors.

It doesn’t matter where you are, because that is needed for everybody who is going through an important change and has a weight of responsibility on their shoulders. If people want to know more about it, just check the book website, www.ReinventionAtTheTop.com, where you can order the book, and you can actually download the scorecard and the PDF. If people want to talk a little bit more about it, they can contact me on LinkedIn. I’m very much present there.

Thank you again, Andrea. Take care.

Thank you so much, J.R., for a fantastic conversation.

Four Key Takeaways On Executive Reinvention And Career Growth

Really interesting conversation with Andrea. Let me give you four ideas to take away. First is that success can sometimes become a constraint. It’s important to periodically question whether the habits and the tactics that have brought you to the point where you are are still serving the work ahead, the work of you and the work of your team and your organization. Second is to know your leadership scripts. We did not talk about this so much in the conversation itself, but we’ve got these things that we perform as leaders, and sometimes, under pressure, our inherited defaults take over. We say we do not want to be defensive, but we get defensive.

We say we want to ask questions rather than talking a lot, but we start talking a lot. Recognizing these things gives you a choice as to whether you want to keep behaving in that way or whether you actually want to pull yourself back into the way that will be right for that moment. Third is that authenticity is not the opposite of authority. Credibility grows when identity, message, and behavior align. This is a big part of the through line that Andrea talked about in the conversation. That means that people can see your rough edges.

You should always be working on improving, but this idea that you have to be the perfect, polished leader is unrealistic, and it’s not sustainable, and it doesn’t come across as authentic. There’s so much power in being more authentic. Finally, reinvention requires action, not just introspection. Yes, you have to do the inner work, but then you have to figure out what am I going to stop doing? What am I going to keep doing? What am I going to start doing? All of that allows you, over time, in that test, to learn, iterate the approach that Andrea discussed, and become the leader that you want to become.

I hope you found this conversation valuable. Please subscribe, leave us a review, and share the episode with someone in your life or your workplace who is working on becoming a better leader or trying to build a stronger career. If you’re an organization, I do workshops and keynotes on a variety of management topics. If you’re an individual, you can sign up for my membership community, which is called Pathwise, and our newsletter, PathWisdom. Thanks for tuning in. I’ll see you next time on the show. Take care.

Important Links

• Andrea Petrone
• Andrea Petrone on LinkedIn
• The World Class Leader Show
• Reinvention at the Top
• PathWisdom
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter
• Be the Boss You Wish You’d Had: A People-First Guide to Management

About Andrea Petrone

Andrea Petrone coaches CEOs and senior leadership teams through the high-stakes moments that define careers: transitions, crises, reinventions and the personal demands of leading under pressure. Known as The CEO Whisperer, he focuses on how leaders think, decide and perform when the stakes are highest. His work is built on what he’s seen firsthand in the room with leaders at the top.

Over the past two decades, Andrea has worked internationally across Europe, the Middle East and Asia with leaders from global corporations, mid-market and management consulting companies He has partnered with CEOs and senior leaders from organizations including Shell, Unilever, Denora, Takeda, EssilorLuxottica, ENI and Snam. Before starting his entrepreneurial journey, Andrea spent more than twenty years in senior leadership roles, including CEO and managing director positions, across the energy sector, construction and management consulting.

Andrea also serves as a senior leadership advisor with JMW, supporting large-scale transformation programs. He is also the host of The World-Class Leaders Show, a leadership podcast ranked among the top 5% globally, where he interviews leading CEOs and global business figures about the decisions and mindsets behind exceptional leadership. He publishes the CEO Playbook newsletter and leads WCL21, a private membership for CEOs committed to leading at the highest level.

Originally from Italy, Andrea has lived and worked in multiple countries and is now based in London, UK. He holds a Master of Management from IE Business School and is a certified executive and neuroscience coach.

Are today’s managers too nice? In our efforts to create more compassionate workplaces, have we gone too far in avoiding difficult conversations, lowering expectations, and letting poor performance slide?

In this episode of Career Sessions, J.R. Lowry sits down with Matt Hunter, executive coach and co-author of Tough Enough: How to Lead a Team to Greatness Without Being a Jerk, to explore why great leadership requires more than kindness. It also demands candor, accountability, high standards, and the willingness to make uncomfortable decisions.

Matt argues that many organizations have fallen into what he calls the “Mirage of Compassion”: creating the appearance of caring for employees while failing to challenge them to grow and perform at their best. But there’s a fine line between being appropriately tough and becoming the kind of boss nobody wants to work for.

Together, J.R. and Matt discuss how to find that balance, including:

Why managers often confuse compassion with avoiding discomfort

How to establish clear expectations and hold people accountable without being unfair

Why psychological safety should encourage honest disagreement, not suppress it

How leaders can become more comfortable giving, and receiving, difficult feedback

Why the right level of toughness depends on your ambitions, circumstances, and stage of life

They also explore the risks of taking toughness too far, drawing lessons from high-profile business leaders and Matt’s own experiences as an entrepreneur and executive coach.

Whether you’re managing a team, aspiring to leadership, or simply trying to navigate a demanding workplace, this conversation offers a thought-provoking perspective on what it really takes to achieve high performance without sacrificing humanity.

The takeaway: Being a people-first leader doesn’t mean making everyone comfortable. It means caring enough to tell the truth, set meaningful expectations, and help people become their best.

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/matt-hunter

Watch the episode here

Listen to the podcast here

Are Managers Too Nice? The Case for Tougher Leadership, with Matt Hunter

What if one of the biggest problems in management were that we’ve become too nice? Not too caring or too human, but too willing to avoid the hard conversations, to tolerate mediocre performance, to soften our feedback, to protect people from the discomfort that’s going to help them grow. My guest, Matt Hunter, argues that great leadership requires something different, being tough enough. Tough enough to set ambitious standards. Tough enough to tell people the truth. Tough enough to hold them and yourself accountable, and tough enough to make difficult decisions when the situation demands it.

To be clear, this isn’t an argument for bringing back the screaming fear-based boss. It’s about finding the narrow zone that exists between being too soft and becoming a jerk. Matt is an Executive Coach and a Co-author, along with John Baird, of the new book, Tough Enough: How to Lead a Team to Greatness Without Being a Jerk. In this episode, we’ll explore whether management has overcorrected, why kindness sometimes becomes avoidance, and how leaders can combine humanity with high performance. I’m J.R. Lowry. This is Career Sessions. Here’s my discussion with Matt.

Matt, thanks for being with me. I’m glad you can be on the show.

Thanks so much for having me. It’s great to be here.

We’re doing this a day before your new book comes out that you wrote with John Baird. I want to get right into it. The basic premise, as I took away, is that we’ve overcorrected in trying to make workplaces more humane. What are we getting wrong?

Let’s say from the late 2008s, as these tech companies started to grow. We began this process somewhere along the line. Someone thought that, “If our people are happy, then they’re going to do better work.” They made some connection that if we could just make our people happy and feel good, they’re going to do better work. As we progressed into the 2010s, there started to be some of these more social movements.

All of a sudden, managers became scared of holding high standards. They had to give these employees whatever they wanted. There were basically all of these factors that incentivized managers to be nice and placate and not share how they feel. Not hold people accountable, because you don’t want to upset your people. You don’t want to lose your own job.

Although. we think that movement was helpful in the sense of, it’s good to take care of people more. It’s good to care about people. We feel like there was a strong overcorrection and that most of these companies and managers went too far. In the process, we lost our ability to drive for performance, which is at the end of the day, what we’re coming together to do at work.

We’re coming together to deliver a performance. Kim Scott calls this quadrant of her framework, ruinous empathy. You call it the mirage of compassion. In the book that I’ve written with Daniela DeLuca, we called it something like living in the lounge chair. What does that look like in day-to-day life from your perspective? How can a leader or manager of a team or somebody more senior tell the difference between genuine compassion and just avoiding discomfort in hard conversations?

We believe that all leaders have a tough miscalibration problem. Our thesis in the book is that all great companies are built by tough leaders and tough teams. If you want to get better results, you need to have higher levels of toughness. What happened because of this mirage of compassion, which is essentially this appearance of care without giving the real care that matters, which in our opinion is sitting with people, partnering with people and helping them achieve important good goals.

If you’re not supporting someone in their development, we don’t believe that is true compassion. What ends up happening is that most managers and leaders move towards the side of the toughness spectrum that we call the comfort zone. Most leaders tend to move to that zone where they have lower levels of toughness. They’re prioritizing comfort. As a result, they’re essentially ruled by their emotions. If they don’t feel like holding someone accountable, they won’t. If they don’t feel like working, they won’t. If they don’t feel like ruffling someone’s feathers, they won’t. That is a bit of what it looks like when you go over to that side of the spectrum.

The challenge, though, is eventually that’s going to come back and bite you in the backside if you’re being held accountable yourself. Maybe the whole corporate culture is that way, in which case it’s probably a company that’s falling short of its potential. If you’re living in a company that’s got a performance expectation and you’re living in this mirage of compassion or whatever you want to call it. It’s going to come back and hurt you.

There’s many companies and institutions. A lot of academia lives in the comfort zone as well. Certainly, many large companies that have been around for, let’s call it decades or hundreds of years, we see a lot of those cultures. Live in the comfort zone. Let me make no bones about it. Living in the comfort zone is not going to get you anywhere close to your highest potential. You will not be able to create great work from that zone.

I hear you. At the same time, you’ve got a lot of people who will say, “If I can get paid X thousand dollars a year and live in my comfort zone, I’m good with that.”

For sure. That feels better. If you have low levels of toughness, you’re ruled by how things feel, how you feel and how other people feel. You don’t want to ruffle other people’s feathers. You don’t want to feel uncomfortable. The end result of being over there is that you’re not going to produce great work. If you prioritize the mission, it’s likely not going to feel great. It’s going to be painful. You’re going to have to sacrifice a lot. You will create better work. It comes down to, “What do you care about?” If you don’t care that much about work, if you don’t want to put that much into it and you can get paid a salary to be in the comfort zone, that’s fantastic.

You should go ahead and milk that if that’s what’s important to you. At the end of the day, it comes down to what do you want specifically as a leader and how tough do you want to be and then just go for that level of toughness. If your choice is to be in the comfort zone, then that’s great. In our book, we have this concept called the toughness spectrum. It’s a spectrum where you have toughness on one side and comfort on the other side. As you move from comfort to toughness, you’re going to get better results, generally speaking.

If you want to live in the comfort zone, you are essentially ruled by how you feel. Now on the other end of the spectrum, when you have high levels of toughness, essentially your mission is everything. It doesn’t feel as good. It’s painful. It’s hard. You have to work hard here, but you do incredible work. What I want everyone to come away with is to pick the part on the spectrum, the amount of toughness that works for you.

I hear you say that, and what comes to mind is, I’ll say, putting myself in the shoes of somebody who may say, “I’m just at a stage in my life where I can’t afford that level of toughness. It’s not that I don’t care, but I’ve got things going on in my personal life that necessitate me dialing back a bit.

Being parents? What’s an example?

Maybe having to care for aging parents or dealing with a health challenge or whatever the case may be. I just wonder whether they feel like, “You’re shaming me for taking a step back.”

Thanks for asking this question. The book’s called Tough Enough: How to Lead a Team to Greatness Without Being a Jerk. When we talk about greatness, we’re talking about an intense playbook. That’s ultimately not for everyone, but it is for all people in the sense that you can pick and choose little pieces to improve the way that you work if you’ve got young kids. I have one young kid and I got another baby on the way. I’m not trying to work around the clock.

I’m not but there are other areas of the way that I’m working where I can ratchet up my toughness that aren’t a function of time. In the book, we have these seven habits of toughness. Some of them are very much, “If you want to get a lot done, you need to work very hard.” You need to sacrifice everything. If that’s not for you, that’s no problem.

I want you to be honest about how tough you want to show up, then just go for that level of toughness. There’s literally nothing wrong with that. There’s no shame in that. I deeply respect that. While you’re at work, there’s some of these other habits that you can apply to get better results that have nothing to do with how long you work.

People will immediately go to the idea that being tougher or being in a tougher environment means everybody has to work harder. There is some truth to that. Let’s not brush over that. At the same time, to your point, there are things you can do. It’d be great to hear you talk about what some of those are that don’t necessarily involve more time.

In an athletic context, people talk about the idea of deliberate practice versus just practice. You’re focusing on getting better at specific things. You’re going to spend that hour working out, but you’re doing it in a different way than somebody might be who’s getting on the elliptical and keeping themselves in a lower zone. If you want to use an athletic analogy here, an exercise analogy.

Firstly to talk about that piece about deliberate practice. If you think of someone like Kobe Bryant, he was doing that deliberate practice, but he was doing it all day long. He famously took like 3 or 4 naps throughout the day to allow him to be able to do that deliberate practice more than others. The working piece, how hard you work, I do think that is 100% a factor. We have these seven habits of toughness. There’s all kinds of other habits you can apply. You can have a strong, clear vision and you can live it with deep amounts of conviction.

Having high conviction around what you’re working towards. You can assemble what we call a cult of incredibles. You can get a team of highly talented mission converted people to rally around your vision. You can harness emotional thunder. You can use the power of what we call quote unquote negative emotions to get your team to focus and shift behavior. You can fiercely pursue the truth. You can be honest and have a culture of candor in your company. You already mentioned radical candor. That is a big one. Can you be honest and passionately debate ideas? Can you build what we call an accountability stack?

Tougher Leadership: High performance isn’t accidental. It requires stepping out of the comfort zone and deliberately choosing your standard of toughness. How do you calibrate your leadership style?

This is your own unique system that drives accountability in your organization or your team. This is a big one that people just miss out on. They don’t do this well. Lastly, can you use the best ideas from warfare that have been developed over thousands of years that match these intense moments? If you have an intense problem or a big opportunity, can you break out of the day-to-day operations and throw your effort behind something that matters for the company? There’s all kinds of other things that anyone at any position can pursue.

That construct of having a set of habits that you can pick where you want to be and maybe almost where you want to be in certain dimensions of your life or even certain dimensions of your work.

Exactly. Let’s be deliberate about how tough we want to be in each area and then go for it. There’s no shame. There’s literally no shame. I am someone who naturally skews to the less tough side of the spectrum. We all know the famous leaders that skew on the too tough side of the spectrum. That gets great results, but it also has a high cost. For me, my natural place that I am most comfortable is to not have the hard conversations, to not hold someone accountable. It depends on how seriously you’re taking it. If you’re taking it very seriously, if it matters to you, then you do need to up your level of toughness.

Personalize this, given what you just said. Do you want to be tougher or do you feel like you are operating in the right zone for your life now?

Toughness is also dynamic. It depends on the situation. It depends on who you’re with, how safe you feel, or how important the situation is to you. Historically, I have not been tough enough. I was a startup founder for fifteen years. I had one company that was acquired by Yelp and I had another nonprofit that has raised a couple billion dollars for charity now. The piece that I fell short on both of those endeavors is that I wasn’t willing to push harder.

I was scared of these big, more emotionally intense moments. I didn’t want to confront the brutal facts of how I was showing up. I thought that I was just crushing it. Anyone who had feedback for me about how I wasn’t, I just wasn’t willing to entertain that. There were a lot of areas where I just was not being tough enough.

Now, in my life, I have the good fortune of being an executive coach and working with startup founders, Fortune 50 leadership teams, and C-suites. I do operate at the right level of toughness. I’m not a workaholic. That’s just not in my nature. For example, when I get in a coaching session, I don’t hold back. I try to be as honest as I can with people. I try to hold them accountable. I’m digging in. I’m using those moments to apply these habits.

It’s interesting what you were just saying about you having a successful exit. You have a nonprofit that’s raised several billion dollars to help the charity, and you feel like you weren’t tough enough. Probably underpinning that as a sense that maybe you underperformed relative to what you could have in those two organizations, which is pretty striking given a successful exit, billions of dollars raised.

Let me fill those gaps in. In both of those, I partnered or worked with people that had very high levels of toughness that were in the hardcore zone. In that too tough zone, which yields the best results, but also comes with the highest cost. In that first one, my co-founder was a force of nature, very strong personality, and incredibly driven. It mattered to him.

I do think that made a big difference, and then similarly with the non-profit, which by the way I just want to be clear. I helped lead that organization. I was in the US. CEO and the president of the global organization, but it wasn’t mine. I didn’t start that organization, but similarly, that one was founded and ultimately led by a guy with very high levels of toughness, so I honestly think that’s why.

Talk about that other end of the spectrum that you were just referencing. How does somebody know when they’re in that danger zone?

We’re talking about this sweet spot of toughness where you have very high levels of toughness, but you still have compassion. We believe that in this tough enough zone with high enough levels of toughness, you can still pursue greatness while having compassion. We think that’s important. Now there’s two zones beyond the tough enough zone. The zone right next to the tough enough zone. It’s called the hardcore zone. This is where you have very little levels of compassion. There’s a little bit, but there’s very little.

This one we think does yield the best results, but it’s not the right fit for most of us to live there. By the way, most of us don’t have the wiring to be able to hang out in that zone. That zone comes with a ton of costs, reputational costs, cultural debt, all kinds of personal costs. We know the track record of many of these “great entrepreneurs.” Their marital track record is pretty abysmal, but they get these fantastic results. Many times, they go on this journey with people at the end that just don’t feel ultimately proud of the journey they went on with that leader.

That’s the hardcore zone. The danger zone is one zone beyond that. This is a very rare zone to tip into. This is where there is literally zero compassion, zero empathy. The mission is so important that even fundamental baseline commitment to ethics is overrun. You could think of Sam Bankman-Fried at FTX, Elizabeth Holmes at Theranos, Jeffrey Skilling at Enron. This is that danger zone where the ends fully justify the means.

Now, most of your audience are not going to come anywhere close to this danger zone. However, there is one habit where people regularly fall into the danger zone, which is the one that we talked about a little bit earlier about how hard you’re working. This habit is called making your pursuit relentless. We all know a lot of people that just didn’t know how hard they should push and they get burnt out. They hurt themselves. They get sick. Their bodies just start to break down and say no.

Let’s talk a little bit more about what that sweet spot looks like. I would imagine people reading or watching might be thinking to themselves that they’ve got high standards as a manager. In your view, what does it mean to hold people to a high standard in everyday management?

To hold a high standard on an everyday basis has a handful of fundamentals involved. Firstly, you want to set clear goals or clear expectations with that person present. That could be a collaborative process if you want it to, but the goals need to be very clear and mutually agreed upon upfront. In addition to the goals, when we talk about standards, we’re talking about how we’re doing our work. There might be certain ways or certain quality bars that we’re talking about.

The work needs to be above these certain bars. When you hear someone say holding a high standard, they’re talking about these ways of working and these commitments that we have. They could be goals, expectations, or “standards.” What that looks like is having some system or mechanism of tracking how it’s going so that there’s a shared reality of how the work is going that both the manager and the direct report agree upon. It’s digging in and having those hard conversations around how it is going.

Being honest as a manager when it’s not going well or when it’s under the standard or when the goal is missing the target. Having those conversations, digging in, triaging the problems, then ultimately, once you’ve given feedback, once you’ve coached, enforcing negative consequences if the work still doesn’t improve. That’s a big step that most managers and leaders shy away from. They shy away from enforcing these negative consequences. Which can be anything from having harder conversations to reassigning work to ultimately putting someone on a performance improvement plan and then letting them go.

As a manager, when somebody is falling short, how do you distinguish between a situation where they just need coaching or they need more time to become more skillful in whatever they’re doing, versus they’re in the wrong role or they shouldn’t be in your organization at all?

What we like to do is track what we call inputs and outputs. If we think of a salesperson, an input would be what’s the work they’re doing. This could be how many calls are they making? How many emails are they sending? How many meetings are they setting up? Those would be the inputs. The outputs are the results. How many sales are they making? What revenue are they pulling? If you can track both the inputs and the outputs, you can get a real good sense of whether the individual is firstly putting in the effort, because that’s one component of performing well in a role.

Secondly, do they have the skills and the acumen or the talent to succeed in that role? Understanding both of those simultaneously will give you a sense of, “Does this person have the talent or they just need to work harder?” For example, when I was in my early twenties, I wanted to be a good singer. I started taking singing lessons.

After six months, the trainer, who was this lovely guy, said, “Matt, we’ve been doing this for six months and honestly, I don’t think you have the ear for this.” Once you get the inputs and outputs, you can have a real good sense because even though I was putting in the effort, it was clear that I just didn’t have it, so you can get a good sense of whether that person’s going to be right for the role.

This is a challenge for a lot of managers to figure out. They often come back to this idea of wanting to be likable. They push off these conversations and then they give the person more time. On the flip side, I’ve worked with people who are like, “So-and-so screwed up on day three, we should just fire them.” Finding that spot in the middle of those two ends of the spectrum is something that more managers need to get better at.

I love that. That’s great. I just want to encourage managers to be in constant conversation with their team about how things are going so that there’s no real surprises here. It’s a stylistic choice. If you go into the super high levels of toughness, if you work for someone like Elon Musk or Steve Jobs, and there’s one what they would call boneheaded mistake.

You could lose your job right there on the spot. Whereas to be a fair and ethical good manager, if someone’s a cultural misfit from the start, and that’s obvious, it’s fine to let them go right away. However, if it’s some performance thing, you need to start coaching and giving feedback right away and giving them an opportunity to live into that feedback.

Certainly, most managers are not giving enough feedback, good or bad. This idea that you guys talk about that will stick with me is this idea of consent first, enforcement second. The idea being, as you were just saying, “Get everybody to agree on the expectations and the goals,” because then the team has agreed on them. It’s not like the goals or expectations are secret and you only find out about them after you’re not meeting them. If everybody truly agrees to them up front, then you should be able to hold them accountable. Both parts of that are important. It creates the context in which you can give feedback, good or bad, to your team.

Tougher Leadership: Great leadership balances deep mission focus with human respect. The seven habits of toughness show leaders how to drive high velocity without becoming jerks.

In most companies, you have an unclear set of expectations. It’s not explicit. No one has opted-in. No one has had that powerful moment of saying, “I’m up for this.” It starts to feel almost like coercion. The manager finally finds the courage to speak up about this thing. The direct report never agreed to it in the first place. That’s a huge issue. You want to be able to look that person in the eye on day one and be clear about what they’re going for, such that you can have these open and honest conversations all throughout the journey.

Talk about this a little bit more at the team level in terms of this idea of teams needing to have both psychological safety and the ability to have passionate disagreement, which you guys talk about in your book. How do you create that environment where you can have both?

It’s interesting. I do think that this term of psychological safety got bastardized. I don’t know if that’s the right word, but it just got mistaken for just keeping people feeling safe. I don’t think that’s what it is. It’s the ability for anyone to feel safe enough to say the hard thing. Once again on this spectrum, you have comfortable organizations where, in the name of psychological safety, they think that we’re just not going to ruffle any feathers because that’s what psychological safety is, and it’s not.

On the other side of the spectrum, you have Elon Musk snarking at psychological safety and thinking it’s nonsense, where he’s also wrong in that domain. Sometimes he will have these deep outbursts or he will be such an intense scary character to the people around him that they will also feel afraid to speak up in those moments. It’s safe to speak up, firstly. That’s most important.

On top of that, if you want to run a good business, you need to be making good decisions all the time. To do that, you need to passionately debate. You need to be able to tell people that things are not good enough or this idea is not good enough. You need to be able to talk it out to ultimately land on a good solution. There’s a needle to be thread for psychological safety.

Can you tell when you’re watching one of these spirited debates go on that it’s a productive disagreement and not just a dysfunctional fight?

Lots of both. A functional debate is talking about the idea, being hard on the idea. A dysfunctional one is then going to the individual, making it about the person. You’re a bad leader. You’re not a good product manager, etc. That’s one element of dysfunction. There’s many other elements of dysfunction, like getting down these rabbit holes that don’t matter. There’s so many ways that a conversation can become dysfunctional. I do think, generally speaking, you’re having a focused, targeted conversation about one aspect of the product or the idea, and it’s in service of making that idea better.

Coming back to this idea of being willing to have hard conversations, a lot of times leaders struggle to have truth spoken about themselves. They signal to people that they aren’t open to feedback, aren’t open to advice, aren’t open to others’ experience and knowledge. You coach people. You coach CEOs, and a lot of startup founders. How do you get them to be more willing to take that candid feedback if that’s an issue for them?

It’s hard. I have sometimes delivered 360 reviews around how that leader is showing up. I have delivered some of those to these, let’s call them hardcore leaders, that those conversations felt like wrestling a grizzly bear. There’s something with powerful leaders where they get quite defensive. That’s the first reaction. That’s a natural normal reaction because it’s just hard to receive this feedback. It’s very painful, especially the first time.

Tougher Leadership: Clear expectations prevent defensive friction. When managers secure consent upfront, accountability becomes an ongoing partnership rather than surprise criticism.

If you think of yourself, let’s just say you’re an overweight individual and you want to get into better shape. That first time you step on the scale, is not going to be pretty. You are not going to like the number you see. If you want to start budgeting, you start looking at how much you’re spending. It’s not going to be pretty. It’s going to be painful.

If you start to get in the habit of receiving that feedback, it’s going to become less and less painful. If you work with that feedback, it’s going to become easier to receive it. You’ll start to notice this flywheel of improvement. Your relationships will get better. Performance will get better. There’s a lot of incentive to just get in that habit. It’s just good hygiene as a leader.

You get a lot of people who, despite their success in life, are insecure and they feel like, “I’m successful enough. I don’t need the feedback, so I’m not even going to be open to it.” It hurts them in the end.

I agree. As someone who has a decent amount of insecurity, just like pretty much everyone else, it’s hard. It always stings, but ultimately, it’s for the best.

Last question. For a manager who’s reading to this or a more senior leader who’s thinking, “I’m probably too nice. I avoid conflict. I soften feedback. I give people too many chances.” What are two or three things that you would suggest to them that they should focus on right away?

All of us can take a meaningful step towards the tough enough zone. For the vast majority of us, that looks like a few different things. One, being very clear about what it is you’re working towards. What’s your mission? What’s your goal? Start to share that with a lot of conviction. Start to take it seriously. If others are not taking it seriously, step in and have conversations with them. Understand why they’re not and see if you can get them back into this place of taking it seriously. That’s the first one.

The second one is to give and receive good candid feedback. While you do that, I want to see you start to share your own personal emotions that you’re feeling about the situation. It supercharges these conversations. It helps the recipients start to code the conversation as important. If you can share that you’re disappointed or frustrated and you need something more from them, that’s a big skill that will help level up your toughness and your performance. Finally, I would love to see you build a system for holding people accountable.

In the book, we have the six steps of any good accountability stack. We’ve talked about some of them, but I would encourage you to check them out. It’s a pretty robust list and build a system of accountability that works for your context, your mission, your team, and your leadership style. If you can do that and you can run that system well, give and receive feedback and orient people to a goal that you have high conviction around. You’re going to see phenomenal results.

Good advice. I wish you well with your book launch, which, as I said earlier, is the day after we were recording. It goes out into the world. It’s an exciting time. A little bit probably nerve wracking as well. I hope everything goes well with the launch for you and John.

Thank you so much. I appreciate it. Great to be with you. This was a lot of fun.

Let’s wrap up the conversation that I just had with Matt. Here are four ideas that I hope you will take with you. First is that being people first doesn’t mean avoiding discomfort. Great managers care about their teams, but that doesn’t mean that they avoid having difficult conversations or delivering candid feedback or making tough personnel decisions when they’re required. Compassion and accountability aren’t opposites. The best leaders practice both.

Second is that high performance starts with clarity. You can’t fairly hold people accountable for expectations that they never understood or agreed to. This is the consent part of what I was talking about with Matt. Set clear standards, establish ownership, measure what matters, and create a regular cadence for reviewing progress. This helps ensure that accountability, the enforcement part, that’s the second part of that message, feels less personal and becomes more about commitments the team has made together.

Third is that toughness does need guardrails. Intensity, relentless pursuit, truth-telling, and even some of the warfare tactics that Matt describes can produce extraordinary results. Pushed too far can damage trust and culture and people’s lives by extension. The goal isn’t maximum toughness. It’s being just toughened up, hence the title of the book, Demanding Excellence While Preserving Dignity, Integrity, and Respect.

Finally, it’s this idea that you need to find the environment that’s right for you. Picking an environment that is less tough may be what’s appropriate given your ambition and what is going on in your life. At the same time, others may choose to do something that is a tougher environment and they opt-in to that. It’s what works for us. That may change depending on the task that we’re focused on. It may change in our work life versus our personal life. It may change in the season of life that we’re in.

That is okay as long as you are comfortable with the consequences of where you choose to put yourself on that continuum. I hope you found this conversation valuable. Please subscribe, leave us a review, and share this episode with somebody who is aiming to become a better leader or build a stronger career. If you’re an organization, I do workshops and keynotes on a variety of management topics. If you’re an individual, you can sign up for my membership community, which is called Pathwise, and our newsletter, PathWisdom. Thanks for tuning in.

Important Links

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About Matt Hunter

Matt Hunter is an executive leadership coach and author. He has two decades of experience founding, leading, and coaching companies, most notably cofounding Turnstyle (acquired by Yelp) and serving as president and US CEO of Founders Pledge, a community of entrepreneurs that has pledged over twelve billion to charity, with more than one billion already deployed. Today, he coaches founders and CEOs of high-growth companies backed by firms such as Andreessen Horowitz, Accel, and NEA, with a combined valuation in the tens of billions. He is expanding his work to include public companies and elite sports teams. He lives in Boulder, Colorado.

What happens when your commitment to putting others first comes at the expense of your own well-being?

Kristen Hadeed built Student Made into a successful business known for its people-first culture. But after years of prioritizing her team and company above herself, she reached a breaking point. She had lost her passion, felt disconnected from herself, and realized that the leadership philosophy she believed in had become a source of burnout and resentment.

In this episode of Career Sessions, host J.R. Lowry sits down with Kristen, author of Permission to Screw Up and Human Leadership, to explore her journey from people-pleasing entrepreneur to a leader who understands that caring for others shouldn’t mean abandoning yourself.

Kristen shares why she made the difficult decision to close the business she’d spent years building, how deeply held beliefs from childhood shaped her leadership style, and why avoiding uncomfortable conversations can actually damage the relationships we’re trying to protect.

They also discuss practical ways to become a more effective and authentic leader, including how to recognize the beliefs holding you back, make time for self-reflection, give meaningful feedback, and have difficult conversations with courage and compassion.

Whether you’re leading a team, navigating burnout, or questioning whether you’ve outgrown your current role, this conversation offers a powerful reminder: great leadership isn’t about being perfect or keeping everyone happy. It’s about having the self-awareness and courage to lead yourself as well as others.

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/kristen-hadeed/.

Watch the episode here

Listen to the podcast here

When Putting People First Results In Putting Yourself Last, With Kristen Hadeed

Kristen Hadeed has spent much of her career thinking about what it means to put people first. She built Student Maid into a company known for its culture, wrote a book about giving people permission to screw up, and became a sought-after voice on leadership. Along the way, Kristen discovered that there can be a dark side to people-first leadership. In trying so hard to take care of everyone else, she stopped taking care of herself.

As she puts it in her new book, she abandoned herself and called it leadership. That realization sent Kristen on a much deeper journey. Examining the beliefs that were driving her, learning to recognize what her resentment was trying to tell her, and finding the courage to have conversations that she had spent years avoiding. Her new book, Human Leadership, is the story of that journey and an exploration of what leadership looks like when we stop trying to be the perfect boss and allow ourselves to be fully human. Here is my conversation with Kristen.

Kristen, thanks for being with me on the show.

Thank you so much for having me.

I’m really looking forward to this conversation because it is so much about your personal journey. Why do not we not start with that at the very beginning of your career? You were still an undergrad. You started your own business and, obviously, started developing your own leadership philosophy along with that. Over the years, you realized that it was not maybe everything that you wanted it to be. What was that moment where you started to realize that the leadership philosophy that you thought was making you a good leader was actually hurting you?

I was sitting in my apartment. This was probably ten years into my journey as an entrepreneur and as a leader. It was one of those nights where I just caught my reflection in the window, and I did not recognize the person who was staring back at me. I just felt so disconnected from myself, from the work that I was doing. I did not feel in a place where I was passionate and inspired and lit up, which was always how I was as an entrepreneur and a leader.

It was just this moment where I had to face that whatever it was that I was doing was not getting me to the place that I wanted to be. I needed to rethink what leadership looked like for me because so much of this I knew was tied into my business and the way I was leading. Just a quick story, when I was nineteen, I started a cleaning business, and it was never my intention. I thought that I was going to work in finance, and I started cleaning houses when I was in school, and it turned into a company. Pretty much overnight, I became a leader of a team, and I read so many books that I could find out how to be a great leader and how to build a great company.

The Trap Of Self-Sacrifice In Servant Leadership

Everything that I read was about servant leadership and putting people first, which is something I still very much believe in. What I realized that night was that I had taken it too far, and I had put my company and my team first to the point that I had sacrificed myself and everything that I needed. I had focused so much on building this great culture for others and relationships with others. Yet I felt so not taken care of in the same culture that I had built and not connected to myself at all. That was my wake-up call.

You write about it being as if you were abandoning yourself. What did that actually mean? How did that manifest for you?

Abandonment in so many ways. I think first I was more than a decade into leading my company, and I had changed as a person. I had changed in what I was passionate about and what I was excited about. Instead of going after the things that I really wanted to go after in my life, I felt like I could not make changes because those changes would affect everyone in my company. Abandoning my own growth and evolution as a person. When it came to having hard conversations, I avoided that. If there were people who were not meeting expectations, I really resisted having those conversations because I did not want to hurt people.

I was abandoning what I needed, and the work was falling on me. Even though I had people on the team who wanted to help me, I did not see that. I saw me asking for help as burdensome, because leaders are supposed to take the brunt of it all. I kept it all on my shoulders. These were the ways, the micro ways every day that I was abandoning myself that then added up to this night where I do not even recognize the person staring back at me. This was someone who, in the beginning days of my company, would work until two in the morning without even trying.

I am not saying that should be the norm, but I was so inspired by what I was doing in building that I could not stop. Now it was this feeling of, I do not want to be doing this anymore. I feel trapped inside of this. I want to do anything but, and that was such a shift for me. It was not really about my company. What I learned as I went along this journey is that it was because I had not prioritized myself. When you do that for so long, you get to this point where you realize that you have not taken care of the things that you need, and that has to change in order for the feelings inside to change.

There is a moment you described in the book, I think, where you are asking everybody to rate on a 1 to 10 scale how they felt about the business. I’ll tell you the story.

My heart races when I think about that meeting because we had someone who was a mentor of mine who was leading my team, my leadership team, through a meeting, and he asked us to look at different parts of the business and our team dynamic and rate these areas on a scale of 1 to 10. One of the questions he asked was about our personal happiness at work. Everyone on the team went before me, and their numbers were nines and tens. My number, the truth was, was like two. I cannot remember. I said 9, or 10 or something at the moment, because I just did not feel like I, as a leader, could say I am a two.

What it really was at that point was that I had just outgrown cleaning. When I started the company, it was not something I intended, and it was an amazing company, and I learned so much in it, and I was ready for my next chapter. I was just in this place where I was working on something I was not passionate about anymore, which was an impossible dilemma. How is the leader of the company? It was so many people depending on you. Do you say that out loud in a meeting? Instead of saying the truth, I gave a number that was not true.

You decided to shut it down.

Having The Courage To Close A Thriving Chapter

That was not easy. Now when I look back, I think, what took me so long to make that decision? I thought that the most caring thing to do was to keep doing it. Now when I look back, I realise that if, as the leader, your heart is not in it, if you are not inspired, you cannot possibly build the best version of your company. It actually was not me who made the decision to close the company and transition to what I am passionate about. It was someone on my team who had the courage to say to me, “Let us go after what we are all passionate about.”

I learned that I was not alone in how I was feeling, which I think was a big light bulb moment for me in that meeting where we all rated 1 to 10. I am pretty sure I was not the only one who gave an inflated score. My leadership team also had this vision for a different future that we were all excited about, leadership development work and so much of what we were doing in the company that just was not around cleaning. Eventually decided to close it and go fully into what we were most passionate about. I do not know if I could have done it without the courage of my team giving me that permission as well.

Where does that leave you? You talked earlier about reading all these books and learning about servant leadership. Where does this experience leave you on the topic of servant leadership now?

I am still such a believer in putting other people first and caring for others. I love everything about servant leadership. I just took it too far. I took it to mean that if I am putting other people first, then I come last, or my needs are the ones that are always trumped compared to what other people need. Now I see that they are all important. I do not want to be the leader that says, “It is my needs over everyone else’s, and I do not care what yours are.”

I want to be able to be a compassionate leader who prioritizes my own needs and also makes room for what other people need. It looks like having a lot of courageous conversations. Sometimes the needs that we have are in conflict, and it is like, “This is what I need. I hear what you need.” Let us figure out a way to make this work. Maybe it does not work anymore. Having those honest conversations. When we think about servant leadership, we think about leadership. Leadership cannot be that you are not leading yourself in some way.

When I think back to how I was leading, I do not think I was inspiring anyone on my team. What they saw was someone who was burning out, who had lost passion, who was disengaged. That is not leadership. I have learned that in order to be the best servant leader and caring leader, you have got to think about filling your own cup. It is not selfish to do that. To me, it is the foundation of truly generous and compassionate leadership.

What did you change in the way that you approach your day-to-day as a result of all of these little epiphanies, maybe leading up to a big one?

Aside from deciding to transition the entire company, which was, I think, the first step. For me, that was a huge step because I realized in making that decision that the world did not fall apart. I remember the meeting I had with my team to tell them about this decision, and all of our students. I was so worried about this meeting. I thought everyone was going to be devastated. Instead, they were encouraging. Actually, someone said, “You created Student Maid as a place for us to learn about ourselves and go pursue our dreams, and we want the same for you.”

Honest Communication Builds True Connection

That was a powerful moment because this case that I had built up in my head that everyone would be upset, the evidence showed that was not true. What else am I telling myself that is not true? If I had to boil it down to one thing, the biggest change that I made was just having honest conversations when there was something that I was feeling, actually expressing that out loud. So many times I realized that what I wanted was what my team wanted too. I just never gave them the chance to help me or support me because I was not speaking it out loud.

It made our company more honest and more transparent, and it is not just me having those honest conversations. It is my team having them with me. Often I think we avoid the hard stuff because we think it is going to hurt someone, especially if we care about people. We want to be a caring leader when, in fact, it is the thing that not only takes us to the next level, but builds more trust and connection.

Somebody said to me at one point, “A nice boss is not necessarily a good boss.” You can be too nice, and you are not taking care of yourself, or you are not really pushing your team to be better, which obviously is the role of a leader as well.

I have had to really sit with what it means to be a caring leader. Is a caring leader someone who avoids telling someone when their performance is not what you need it to be when someone has not met expectations? When we reverse it, if you were in that position, if I were in that position, I would want someone to tell me. No, it is not caring to avoid the conversation or to sugarcoat it to give it a softer landing. I have learned that you can be really caring and be really honest with people. They are not separate. They are actually connected. The more honest you are, the more caring you are.

In that conversation where you went to your team and said, “Effectively, I do not want to do this anymore. How did that conversation go? What did you say? How did you position it?

Human Leadership: Walking away from a business you built isn’t failure. It’s an act of alignment and honest leadership.

What helped me is that I knew where I wanted to go. Without that piece, that would have been an even harder moment. I knew that I was ready to transition away from the business because I had a vision for what I wanted to do instead. Over the years, I learned that my real passion was in leadership development work, which was what the company was about. We cleaned houses, but really we developed students and helped them become better leaders. We had started doing that for organizations outside of our company and helping these organizations build more human cultures.

That is the work that my team, my leadership team, and I wanted to do full time. When I had this meeting with my team, I was just very honest about that. I said, “Along the way, I have learned a lot about myself, and I have learned that this is what I am really passionate about, and I am going to miss this, and Student Maid will always have this special place in my heart, you will, and I am ready for the next chapter.” We did not do it abruptly. We gave time for that transition. We were able to work with two different cleaning companies who offered everyone a job if they wanted it.

We really thought about how to take care of our people along the way. At that moment, my team saw me as human. They saw me as someone who has passions and dreams just like they do. For those tuning in and watching, no matter where you are in your career, whether you own a company or not, I think a lot of times we just make up these stories that other people are going to respond negatively when we go after the things we want in our lives. I am just so grateful that I confronted that because I think about what if I lived my whole life without making that decision, only to find out that they supported it? They wanted that for me too.

How many of them ended up coming along the journey with you into what you are doing now?

My leadership team did. There are four of us today, myself included, so a much smaller team. I think even when I made the decision to transition the business, I still tried to find a way to take all of our students with us. Another lesson in my leadership is that I promised maybe we could find opportunities for everyone. Those did not pan out. I had to go back and say, “No, that is not going to work out.”

Just in that transition, I learned even more about honest communication and saying, “This might look like us never working together again. That is probably what it is going to look like.” Just being clearer about that. It was a learning. These decisions are not easy. We all wish we could make them without the risk of hurting anyone. If we are going to live courageously, lead courageously, sometimes that means that people do get hurt. You get hurt sometimes.

I know you went on an inner journey throughout this whole process. Now that you are working with other people, how do you coach and counsel them to go on that inner journey for themselves?

It is about learning to see yourself and to really spend that time with yourself. We are taught to focus so much on others, and how often do we put that same focus inward? I do not think it is enough to just be self-aware. That is the first step. For me, I could not become more self-aware without the help of others. I had coaches, mentors, my team giving me feedback, and therapists. That is one of the gifts of being human is that we need each other. We need to say, “Where do you see me getting in my own way? How do you perceive me as a leader? Where do you see me getting stuck?”

Challenging The Hidden Beliefs That Hold You Back

Having these conversations is what helped me see myself clearly for the first time. It is what do you do after that? It is this willingness to actually change your behavior and change the decisions that you make. That is hard because it is probably a habit. For me, I learned through a coaching session that I had a belief that it is my job to keep everyone happy around me. That is why I avoided tough conversations. It is why I did not ask my team for help because I was afraid to burden them. It is why I never transitioned the company when I first wanted to.

In order to move beyond that belief, I had to be more comfortable with the fact that people may not be happy with all of my decisions and all of my conversations. It felt like stretching out of my comfort zone in the biggest way because I did not want to do that. The more I did it, I learned, “The world does not fall apart. My relationships actually get stronger and better.” It is different for all of us, but it is learning to see yourself, investing in the time and the relationships that can help you see yourself, and then doing something with what you discover.

You talked about beliefs a minute ago. A lot of us operate with beliefs that are formed in the early part of our lives. Was that true for you?

Yes. This belief is that it is my job to keep everyone happy. It definitely came from my childhood. It came from the fact that, as a kid, I was always the person in our house who kept the peace. If there was an argument between my parents, I would go find them. I would bring them together. I would say sorry. That was the role that I continue to have in my relationships. You add that with everything I had learned about servant leadership and wanting to put other people first. It was just this recipe for being so afraid to hurt people, but it is different for everyone. It could be a belief that you cannot fail or that you are not good enough, or that you do not belong, and it is usually what is underneath the decisions and actions where we are getting stuck.

Are you an oldest child?

I am.

That is very true for a lot of oldest children, maybe not the peacekeeping part, but certainly the feeling like you have to be the responsible one in the room when your younger siblings are all causing chaos.

Yes. When I learned my belief, I wanted to take that to my team because I wanted to see, “If I have this, what does everyone else have?” We had some of the most meaningful conversations, and I learned about everyone’s life. There is someone on my team who thought that she was not good enough. Up until that point, I could never understand why, any time we would have a conversation about feedback, she would shut down.

She would get really defensive. I realized it was because of that belief. It would just trigger this feeling that she could not do anything right. Once she worked on that, we were able to have such great feedback conversations. We all have them. A lot of times our beliefs help us get to where we are. There is a part to be grateful for, but then it is also, “Where am I being held back by this belief, and how do I challenge that and change my behavior?”

I would imagine having that conversation with your team was very difficult.

Human Leadership: Are you leading your team, or are your childhood coping mechanisms running the show? Unpack the beliefs driving your decisions.

It was definitely one of the most vulnerable we had had up to that point. We had the trust to be able to have it. That is a key ingredient for a conversation like that one. We were at the time I was hosting a monthly leadership session where we would come together and we would just spend a whole day together learning about leadership. When I did that exercise with my coach, I thought, “This will be great for this leadership day we have.”

It was very vulnerable. I am so grateful for my team’s courage and willingness to share, and we learned so much about one another’s lives. It increased our empathy because, for behaviors that frustrated us, we could understand where they came from. It was not a hall pass. It was not like, “You can just act that way because that is your belief.” How do we challenge each other to outgrow the parts that are holding us back?

Having this realization that you do have these biases and beliefs that shape how you think and how you react to things is a start. You talked about self-awareness being a start, but then knowing how to check yourself in the moment when it happens. The person who would get defensive with feedback because she may not believe in herself as much as she should. When she is getting feedback, it is a wholly different thing to realize that you were having that reaction and to course correct right then and there.

It does not happen if we are not willing to be curious about ourselves, to take time to get to know ourselves. It is the most important relationship of all. Something I like to think about too is how much time this week I have connected with myself. If I have a moment where my emotions are higher than they normally are, or I am feeling an emotion that is not so positive, that is a clue. That is a time to stop and reflect and think about what is happening here and to get curious about it. It is that daily habit of reflection and curiosity that I think is how you learn to lead yourself.

That is very true. Just in the sense that you do need to give yourself reflection time. Too often we just get so caught up in the heat of the day-to-day. The days are long as they are without having reflection time, but finding even little moments to have a bit of reflection can make a huge difference. Was that true in your case?

Yes. What I also realized is that when I looked at my calendar, it just showed that I was not a priority. My calendar was stacked with everything that everyone else needs. It makes sense why when I get to the end of the day, I do not want to do anything else. I just want to watch a show and not think because I have been thinking all day. I had to think about my time differently. I have a practice that really helps me. I call it my daily meeting with myself, and I start my day with it and end my day with it. Before I meet with anyone, I just have 15 or 20 minutes with myself where I reflect.

Establishing A Daily Meeting With Yourself

I reflect on the day. I reflect on how I will take care of myself today. How am I feeling today? Are there conversations I need to have today? At the end of the day, I look back, and I say, “How did I do? What can I learn for tomorrow? Also, is there anyone I need to apologize to?” Sometimes I realize maybe I did not show up in the best way as a leader. This habit of starting and ending with this connection time now is just a part of my routine. It does not happen unless we put intention behind it.

It is a great practice that you have just described. It takes discipline, obviously, but all habits take some amount of discipline until they become the habits that they are. Just giving yourself that time at the beginning and end of each day is a good way to bookend each day and help yourself get better every day. I commend you for doing that.

Thank you.

Come back to this idea of vulnerability. We teach leaders, or leaders often believe, that they should not, cannot be vulnerable with their teams. You had a very vulnerable conversation, probably multiple vulnerable conversations, around that decision point of shutting down a Student Maid. Where do you draw the line between vulnerability and oversharing?

It is tough. Vulnerability is what makes us human. If we are not allowing people to really see us, we cannot build the kind of connection and trust that is possible. Vulnerability can look different in so many ways. Vulnerability could be, I am not sure what to do, or I failed, or I am not sure of the best path forward, but this is how I feel, and I do not know what to do about it. Sometimes, as leaders, we think we have to put on this front that we always know and we always have the answers, and that any kind of vulnerability is perceived as a weakness, but it is actually perceived as a strength because people see you as a human, and then they can help you and be a part of what you are doing.

It is about vulnerability with purpose. It is Brené Brown who says that when I am thinking about something that I want to share, what is the purpose of me sharing this? It is oversharing if there is not a purpose to it. A lot of times, some of the most vulnerable things I have shared are because I need the person on the other side to understand the magnitude of where I am and what I am feeling so that we can come to a better place together.

It is a line I have learned over time. In the beginning days of my company and Student-Maid days, I had keg parties, and I was doing a keg stand with my employees holding my legs up on it. I would say that is the line that was crossed. There is a way to be a leader of a team and have those professional boundaries, but also have these relationships that are really honest. I do not think you can do it without vulnerability.

On the other end of the spectrum is strength and being willing to have tough conversations when they are needed. This is something you have talked about struggling with, and this desire to keep the peace and keep people happy. How did you learn, or what did you learn, about how to do both well? How to keep people feeling happy or at least happy enough, while also holding them accountable?

I have something I follow that has really helped me. It is called the 24-hour guideline. It is just basically a commitment that within 24 hours of feeling something or observing something, I will have the conversation. Do I always hit that? No. Sometimes I go a little beyond. In general, it helps me to stay accountable to not avoiding and just addressing it. The other thing is, in the past, I have focused so much on almost controlling the other person’s emotional experience and trying to make sure that the message is received positively, to the point where sometimes I am not able to get the stuff across that I really need to.

There is a way to be direct and clear and also be compassionate and make the person feel like you care about them. In the end, they are empowered to have their emotional experience. There is something very powerful about somebody being disappointed or frustrated or not happy with what they are hearing, and allowing them to feel that and allowing them to share with you how it is making them feel and what it is bringing up for them.

Practicing The FBI Feedback Framework

That actually builds even more trusting relationships because then you feel safe to be completely authentic with what you feel. One of my favorite methods I love is called the FBI and it is Feeling Behavior Impact. How do you feel? What was the specific behavior that made you feel that way? What was the impact of that behavior? I felt let down yesterday when you were not at the meeting, and the impact is that I fear the team is questioning your commitment to the project.

Tell me more. I am really curious about what is underneath that for you. I have learned that feedback can be a conversation, a dialogue that is really powerful when you can become curious about their emotional experience. If you are tuning in to this and you are like, “I definitely avoid tough conversations, try the 24-hour guideline.” You do not have to do it perfectly. Learn from every conversation, and each one will keep getting better.

Human Leadership: Feedback doesn’t have to feel confrontational. Use the FBI method: feeling, behavior, impact, to build trust and accountability.

Certainly, getting comfortable and practiced and developing feedback makes a huge difference, and not letting it fester. If you come to somebody three weeks later, but something it is going to feel like a much bigger deal even if it really was not a big deal.

It is almost like having the conversations about the smaller things allows you to build the trust to then have the bigger conversation. This habit of just addressing things shortly after they happen, then, when inevitably this is a place we get to in our relationships, there is something bigger. You are really frustrated with the person. Whatever it is, you have the trust built up to be able to have that conversation. If you have not had any of the conversations leading up to it, then that is a really hard one. I also just want to say that I do not find these conversations comfortable.

As somebody who writes about it and teaches it, I still want to throw up a little bit every time right before the conversation. I have butterflies in my stomach, but I think I have learned that fear is a sign of caring. It is because I care about the connection with this person, and I know that avoiding the conversation is the very thing that will threaten that connection. It really is about courage. I do not think we want to wait until the fear is gone because it might not ever be gone. It is really about learning to move forward and have the conversation even when that fear is so strong.

Avoiding it takes a toll on you, and it cheats the other person out of an opportunity to get better.

It risks trust because on the other side, the person is like, “Wait a minute, we have had so many conversations. I never knew that anything was wrong. Now I am learning this. How can I trust you next time when you say everything is fine?” Maybe it is not. It can really do a lot of damage when we avoid it.

Do you give a lot of positive feedback as well?

I do. I am intentional about that because I think that is important too. It gives people the puzzle pieces to know what to do again. If someone is only receiving the critical feedback, then they might not receive it very well because they are not also getting the positive side. With the positive, I just want it to be really genuine. I try to avoid the great work or love having you on the team. Actually, I use the FBI to be really specific about what it was they did and the impact it had. If you do that, you can actually recognize people less, but because it is more intentional, it means more.

All of this, you brought together a new book, Human Leadership. You want to tell us a little bit about it and how it builds on your prior book as well?

Yes. Human Leadership is really the story of learning to face myself and other people. It starts with the night that I looked in the window and could not recognize the person staring back at me, and the journey I went on to get to the place where I look in the window and I love the person staring back at me. I would say it is a book of all of my failures and all the things I avoided, and how they went wrong and how I learned through those moments. It is the most vulnerable thing I have ever written. To be very honest, it is a little scary to put it out into the world. I also know it was the book that I needed to read. If I had read it, it could have probably saved me a lot of heartache and maybe given me some courage to address what I was avoiding.

How does it build on your prior book?

My first book is called Permission to Screw Up. In some ways, it is just a continuation of screwing up, as it is to be human. The first book was very much about Student Maid, the story of building Student Maid and learning how to be a leader and learning that the only way that you can really learn is by failing. It picks up right where Permission is corrupt left off and everything that has happened between the two books. There have been almost ten years between those two books. It is a journey of learning to walk away from the company that started it all and really taking ownership of the life and the career that I wanted.

For our audience tuning in or watching, for you, Student Maid was not just a company as it is with a lot of founders. It had become a big part of your identity and your public persona if you want to think about it that way. For somebody tuning in or watching, what advice would you give them about how to know whether they have hit a point where they have outgrown something that has, up until then, defined you, or whether you are just going through a tough season and you need to push your way through it?

There are definitely moments where we can be working on something we love and still feel overwhelmed and burned out. We unplug for a little bit, we take a break, we get a few things off of our plate, and we come back, and we are passionate and excited to be working at it again. For me, just the underlying spark was missing. It was not something loud, which I think is important. It was like this whisper that I would just always hear that I meant to be doing something else.

Pruning Necessary Endings To Allow New Growth

I could feel my heart pulling me in a different direction, and I was trying so desperately to ignore it because I did not want to think about what that would mean. There is a great book that helped me a lot. It is called Necessary Endings. written by Dr. Henry Cloud. He talks about a rose bush, and he says, “We all have these roses, which are the things in our lives that we want to bloom, but the roses can never bloom if we do not have the courage to prune the bush.”

In order to have beginnings, you have to have the courage to have endings. I just knew that Student Maid was ending. I think we know. We just have to trust ourselves. It is also okay to not rush it. I needed to give myself time to really make that choice. The day when I knew I was ready. Be gentle with yourself and maybe think about the thing that is tugging at you, a rose in your life that really wants your attention.

Thank you. Thanks for sharing your story in your new book. I am sure a lot of people will see themselves in aspects, if not a lot of your story, because a lot of us go through this journey, particularly when we are in the early parts of our career, about who we are and who we really want to be and whether what we are doing aligns with that. The sooner you can figure that out for yourself, to really know yourself as you have worked hard to do, the happier and more fulfilled you are going to be from there on out.

A hundred percent. Thank you so much for having me, and thank you, everyone, for tuning in and watching.

To wrap up my conversation with Kristen just now, here are a few ideas that I hope you will take with you. First is this idea that putting people first should not mean putting yourself last. Great leadership requires caring deeply about others, but when that care consistently comes at the expense of your own needs, values, and well-being, it can become self-abandonment rather than service or servant leadership.

Second is this idea that better leadership starts with understanding what is driving you, and that needs to go beyond just the idea of self-awareness. We all bring deeply held beliefs, fears, and patterns into the workplace, often without realizing it, things that might have developed in our childhood. Doing the inner work to understand these forces and to know how to respond to them and deal with them in the moment really can change how we handle conflict, make decisions, set boundaries, and lead others.

Third is that human leadership takes courage, not perfection. Sometimes the most caring thing we can do is have a conversation that we have been avoiding, tell uncomfortable truths, and make a decision that disappoints someone. Being human does not mean being soft. It means being honest, compassionate, and willing to face difficult things rather than avoid them.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with someone who is looking to become a better leader, build a stronger career, or better understand themselves. You can also look to us for corporate workshops, events, and speaking, or if you are an individual, join our membership community, which is called PathWise. Information on both is available at Pathwise.io. Thanks.

Important Links

• Kristen Hadeed
• Kristen Hadeed on LinkedIn
• Kristen Hadeed on Instagram
• Kristen Hadeed on Facebook
• Student Maid
• Human Leadership
• Permission to Screw Up
• Necessary Endings
• PathWise on LinkedIn
• PathWise on X
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram

About Kristen Hadeed

Kristen Hadeed is an entrepreneur, author, and leadership speaker who helps leaders, teams, and organizations build trust, belonging, and wildly engaged cultures. At 19, she founded Student Maid, a student-powered service company that grew from a college side hustle into a globally recognized business known for developing the next generation of leaders. She is the author of Permission to Screw Up, which has sold more than 50,000 copies worldwide. A sought-after leadership speaker, Hadeed works with organizations ranging from small businesses to Fortune 100 companies and is an Optimist with Simon Sinek, Inc. She created the Human Leadership Program, which has more than 4,500 alumni. Her work has been featured in TIME, Forbes, and Inc., and on PBS, FOX, and NBC’s TODAY . One of her two TEDx talks has surpassed 3.3 million views.

A lot of people spend plenty of time thinking about how to succeed in their jobs, but far less time thinking about how to choose the right jobs in the first place.

In this episode of Career Sessions, J.R. Lowry sits down with Kelly O. Kay, managing partner at executive search firm Heidrick & Struggles and co-author of Show Up to Win: The Insider’s Guide to Getting the Career You Want.

Drawing on decades of experience advising executives and companies, Kelly shares an insider’s perspective on how to manage your career more deliberately. He explains why you should take the recruiter call even when you’re happy where you are, how to test your value in the market, what makes a candidate’s story compelling, and how to evaluate whether an opportunity is actually right for you.

J.R. and Kelly also discuss why internal candidates sometimes struggle against outsiders, how to recover professionally after being fired, the subtle ways candidates sabotage themselves during the hiring process, and why your reputation can follow you for decades.

Whether you’re actively considering a move or perfectly happy in your current role, the message is simple: the best time to manage your career is before you need to.

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/kelly-kay/.

Watch the episode here

Listen to the podcast here

You’re Always In The Job Market: How To Manage Your Career Before You Need To, With Kelly Kay

Too many people I know spend a lot of time thinking about how to succeed in their jobs and probably too little time thinking about how to choose the right jobs in the first place. For example, when should you take a job and when should you leave it? What are you worth in the market? How do you tell your story in a way that makes someone want to hire you? Perhaps most importantly, how do you make sure that the job you’re trying so hard to get is the right one for you?

My guest has had a front row seat to thousands of those decisions. Kelly Kay is a managing partner at Heidrick & Struggles, one of the world’s leading executive search firms. He has advised hundreds of CEOs and board members and thousands of senior executives on some of the most consequential career decisions that they’ll ever make. He and fellow Heidrick managing partner Jeff Sanders have now distilled what they’ve learned into a great new book, Show Up to Win: How to Land the Leadership Role You Want.

We’re going to talk about how to manage your career more deliberately by learning how to assess your value, tell a compelling story, and navigate the hiring process. We’re also going to talk about when you should take the job and when you should turn it down. I’m J.R. Lowry. This is Career Sessions. Let’s get to my conversation with Kelly.

Kelly, welcome, and thanks so much for joining me.

Thanks. It’s a pleasure to be here. Thank you for inviting us.

I’m looking forward to this conversation because anytime I get a chance to talk to somebody from the search world, I know I’m going to learn a lot and I know our audience is going to learn a lot. You’ve got a new book out with your partner, Jeff Sanders. Let’s dive into some of the topics that you cover in the book. One of them is around this idea of knowing when it’s time to move. You guys argue that some very successful people are pretty unsystematic about how they manage their careers, including deciding when it’s time to leave a job. Talk a little bit about that.

Why Career Management Can’t Be Episodic

One of the things Jeff and I frame this book is a very practical guide for career management as well as career transitions. The career management part is something that most executives just think about when they’re looking for a new job. That’s typically kind of the way career management happens for most executives. If I want to change jobs or if I’m getting recruited, that’s when I’ll start lifting my head up. It’s episodic in that way.

The reality is, there’s a very easy way to do career management, which is to say yes to phone calls and say yes to get introduced to others. Be strategic and thoughtful about it so you don’t say yes to everything. You’ve been an operating exec, senior exec for many years yourself. These roles, especially in today’s world, they’re all encompassing. It’s hard to find the time to do it, but it’s valuable to do it because it’s like a compounding effect of relationships that you build over time if you start early enough in your career. At the end of the day, my advice and Jeff’s advice start now. If you haven’t said yes to many conversations, start now and just start building those relationships.

I completely agree. I also think there’s times where you take that call and it sparks a thought of, “Maybe I’ve been missing something that I could have been eligible for.” How do you make sure that you are thinking about that decision of whether you want to stay or go or consider other things in a more systematic way, more comprehensive way?

There’s a number of things and frameworks that we talk about in the book for evaluating. Is the time right? One of the things we talk about, we list twelve different common things we hear why people want to change jobs. Everything from, I’ve plateaued, to I’m out of ideas, to there’s been a leadership change and everything in between. The reality is that in order to have success to talk about, you need to stay at a job long enough so you can point to accomplishments in a role. That’s just the ante.

Testing Your True Market Attractiveness

If you haven’t stayed long enough to achieve something and show results that you don’t have a lot to talk about. That is probably a very early filter. I’ve been here long enough to point to results that are impressive. One of the frameworks we use in this book is, I refer to it as the ABC framework, but it’s labeled in the book as the company and candidate attractiveness framework. It was meant to give leaders a lens to say, “In this market, who am I attracted to and who’s attracted to me?”

Most times, leaders who are looking for a change and trying to figure out if it’s time, which is the question, they’re unsure who they’re going to be attracted to and who’s going to be attracted to them. They miss the second part of that. They think, “I’ve had this success therefore I can get it. I want to get a job at this company or this brand or whatever.” The reality is that companies that they view as aspirational may look at them as a C quality candidate, not because they’re not a great executive, it’s just that they don’t meet the requirements of what the company’s looking for.

Fit certainly matters. How do you figure that out when you’re a candidate? A lot of times people have unrealistic views of their market value, either too high or too low or breadth of their market attractiveness, I guess I would say.

It’s a great question and I hope your readers will listen to this part because it’s one of the things that most don’t do the right way. The advice that we give is up to the leader to figure out how attractive that leader is in this market and to what type of company. As a leader, you may say, “I would view these brands or these companies as aspirational.” Forget the role for a minute, just the company itself. You might win 20% of those because it’s a long shot. It’s aspirational.

B quality companies that I would find interesting, I should win probably 50/50 of the ones I’m competing for. C quality opportunities to the executive would be ones maybe where it’s a company in their space and similar domain. Maybe a similar role. They should win 80% of those opportunities they go to interview. Go out and have conversations. Find out who is attracted to you and who are you attracted to? To your point, sometimes when you take these calls and you start to hear things and you start to meet people, your mind might shift to what you didn’t even prepare or expect to happen.

You, all of a sudden, become interested in a brand that you didn’t think of, a role that you didn’t think of, etc. A quick way to summarize that, is it’s up to the executive to go find out how attractive they are and how valuable they are in this market. Different companies are going to pay different comp packages based on the capabilities that you’re going to bring and the problems they’re asking you to solve.

You’re arguing essentially, Kelly, don’t just take the call, but go do one round of meetings.

Protecting Your Executive Optionality

I would argue to do at a minimum, yes. It’s about, as I said earlier, being strategic. When you do take that first meeting, the whole argument that Jeff and I make is keep the optionality on your side. Most leaders don’t think of a process through the lens of optionality. If you think about it, the goal of a leader is to take the time to go meet somebody. The goal is to have the person that they’re talking to want to spend more time with them, want to learn more, want to engage further so that the leader can decide if the leader wants to invest that time.

At the end of the day, we see a lot of times where leaders will approach a meeting and they’ll put up demands like, “I won’t move. It has to be paid this much money. It needs to be this title.” All those are just blockers. Those are all things that can come down the road. Go meet somebody. Go have a business discussion about what the company is doing? What are they trying to solve? What’s the purpose of why they’re looking for this role? That is the starting point for the discussion. What it’s not is, “I need this much money. I won’t move. I need this title.” That is definitely the wrong way to start a discussion.

That’s pretty counterintuitive though to the way that a lot of people approach those conversations, at least from what I have experienced, because they feel like it’s a little bit like round one of a speed dating process in a way. The idea is to figure out relatively quickly whether there’s something there.

We’re talking about the leaders that we place at Heidrick and in this industry are at the peak of their careers. It’s not about a volume of meetings. That’s not what this is about. It’s about trying to figure out, “I know enough about this company. I know enough about the sector. I know enough about this business model.” That is qualifying enough. If you don’t know some of the people, the CEO, the investors, the board, etc., are all good reasons because it may not be about the job that you end up winning.

It may be about, more importantly, the relationships that you build in the process. Remember, as these leaders show up well in these discussions, the company who has that discussion and was impressed by the leader, how they showed up, are going to go back and tell their HR leader, their CEO, their investors, “We didn’t get J.R for this role. He declined to continue the discussion, but he’s somebody we should all keep an eye on because he’s amazing.” That is what we want.

Certainly, that’s what you want. I want to come back to something you were talking about a minute ago, Kelly, in terms of A, B, and C grade companies. How should somebody, I guess in the context of managing their career, think about, “I could go get a job at this level in an A company, and I could get one at this higher level in a B company, and probably this higher level at a C company?” A lot of people would probably say, “I’d rather have the most senior role in the C company.” You guys would probably argue that it’s more nuanced and complicated than that. I’d love to get your view on how a candidate should think about company quality when they’re thinking about their options.

Executive Career Management: Do you know who’s attracted to your skill set in today’s market? Stop guessing your value and start testing your optionality.

Ironically, I hear in this market and you’re starting to see it, CEOs, former CEOs are stepping back into individual contributor. I see roles in high growth, hot companies. Most leaders, accomplished leaders, would rather be in a high growth company that is performing incredibly well than be a senior leader at a company that’s stagnated or flatline growth or a major turnaround. Those, at the end of the day, are very difficult. What we hear is that they’re not fun. The fun assignments are around growth, and that’s what the best leaders are looking for is high growth and huge TAMs.

It may be a little bit counterintuitive if you have the trade-off of a senior role at a company that is less interesting to you, versus stepping back a level or two at a company that is growing and new opportunities are being created every day. Look at some of these LLM companies, these new frontier companies. Imagine if you were a senior executive. If you went in as a junior leader, chances are in twelve months you would be a senior leader again because the opportunities are just exponential. That is the way the best leaders think about it.

If the growth opportunities aren’t there, the LLMAI companies are an extreme example. If I’m looking at two companies in the same industry, we’ll say they’re both growing roughly about the same amount. How about the optionality that going to an A grade company gives me, versus the optionality of going to a B or C company that may have roughly the same growth, but just not the same quality and prospects?

Removing Emotion From Career Decisions

One of the things that we put in the book is how do you eliminate or reduce the amount of emotion that goes into deciding between multiple opportunities? We list an example in the book, which is we talk about identifying for each leader, how do you define what a quality company is? How do you define what a quality role is?

Thirdly, how do you define what a quality offer is? What we talk about in the book and the framework that we offer is very simple. For each leader, this will be different. It’ll be bespoke and unique to each leader, but identify the 6 to 8 attributes that you as a leader would feel are the priority attributes for your definition, your unique definition of what a company is, and your unique definition of what a role is, and your unique definition of what an offer is.

When you’re in discussions and you’ve boiled your opportunities down to two competing offers or opportunities, as you just laid out. Hopefully, you’ve been able to evaluate both of those against the criteria that you have set at the beginning of your process. Now, it’s a framework only for you, J.R, or for the leader. It could change. It’s not meant to be shown to anybody, but where it is useful, whenever asked, because this is a common question by a company. What are you looking for? What is it you’re looking for?

You could easily now come back and say, “I’m looking for the highest quality company.” They’ll say, “How do you define that?” You’ve already done the work. You can say, “These are the types of attributes to me,” and you are much more prepared for this discussion rather than keeping it all in your head, which 99% of executives do, and relying on the emotion.

Let’s face it, when you’re being pursued or there is interest in your candidacy, it’s easy to get caught up in the emotion. We see executives make decisions around the emotion. If you can eliminate all the emotion or as much as possible, you can keep it focused on the attributes that you believe are authentic to you for the right company and the right role and the right comp package. You’re going to make the right decision.

Having that level of clarity is very helpful. Most people don’t. That’s probably where they get themselves into trouble because they are thinking about titles, more superficial aspects of things. Not so much what they want it to be like and feel like day to day.

That’s an overarching theme of the whole book. The feedback that Jeff and I and Heidrick have been receiving is the intentionality. It’s purpose-built career management where you’re doing things deliberately, intentionally, versus randomly accepting a call that you didn’t expect from a recruiter or a company and you took it. Next thing, you quit your job. The reality is, you didn’t test your value on the market. You didn’t test your attractiveness on the market. It may have been an old colleague or a friend that traded on loyalty or guilt or whatever, friendship. There’s a lot that just happens by randomness and by serendipity. It does not have to be that way.

There’s another point in this process that you guys talk about that’s important, which is getting into the heart of the interview process and being able to tell your story.

This is an important part of this whole discussion because telling the story doesn’t happen just when you’re interviewing with the company. It happens when you’re interviewing with people like Jeff and myself or colleagues in the industry. It happens when you’re getting a strategic introduction. One of the concepts we introduce is a strategic introduction. Anytime you meet somebody, it could be in the process or seemingly before the process.

It’s how to understand the buyer, the company who is interested, or the person you’re speaking with who’s representing the company or individuals looking for talent. Understanding what they want, understanding what they’re looking for, and why they’re looking for it. Get curious and make sure that you are clear on what the requirements are, the capabilities, the experience that they’re looking for before you start talking and telling your story. Your story has no relevance if you don’t know what you’re telling it in relation to.

Step one is just understanding what the company is looking for, such as experiences, capabilities, etc. You can then tailor what experience and capabilities that you bring to the table. It could be from the job that you ran or the most recent job, or it could be from a job or two ago, because the reality is, you’re trying to find and map the most relevant experiences and insights into what they’re most interested to hear about. Not, “Let me just give you ten minutes of a monologue of who I am and where I came from, etc.”

One of the quotes that I love in the book, there’s many that I love, but one is from Fidji Simo for OpenAI. Her comment was, “Be clear about who you are, what you believe, how you think and plan to contribute. Bring ideas. Show them how you think.” That quote kind of sums up how to show up to these discussions. It’s not the title, the comp package, etc.

You’ve heard a lot of these stories in the course of interviewing candidates. What makes a compelling story?

The number one thing that will make a compelling story is how well have you listened to what they’re looking for? It has to start there because that’s the beginning part of it, then how well does your experience match what they’re looking for. There are many times and I would say the majority of the time, especially if you’re interviewing for a role you’ve never had. You could be a C-suite level executive interviewing for a CEO role for the first time or somebody not on the C-suite interviewing for the C-suite.

It’s about making sure that even though you don’t have the most relevant experiences because you have not done that role, it’s making sure that you are at least asking the questions at the altitude and the relevance of the role that you’re interested in trying to win. The common mistake is that people will use the lens of the role they’re in to talk about the role that they’re trying to aspire and elevate to. They have to get mentally adjusted to the attitude of the role that they’re trying to win.

I’ve said many times to many leaders, it’s one thing to know how to talk to a CEO if you’re not a CEO, but learning how to speak like a CEO is vastly different than learning how to speak to a CEO. You can go down the hierarchy of roles. It’s the same concept, which is they just need to figure out how to be the most compelling for the role that they’re talking about based on the requirements that they’re looking for.

There’s a high degree of empathy that’s required in that. You have to put yourself in the shoes of the person who is looking to fill that role and think, “What do they need to see in me?” A lot of people, even the ones who are practiced at telling their story, spend a lot of time thinking about, “How do I make myself look as smart or as technically capable as possible?”

Executive Career Management: When recruiters come calling, emotion can cloud your judgment. Define your non-negotiable career attributes before you enter the room.

It’s true. It’s one of these misnomers about interviewing, and we’ve all kind of been raised to believe that when we interview for a role, that it’s a competition and we need to win. As an interviewer, I ask the questions and interviewee, you answer the questions. That is just not true. The reality is that an interview is nothing more than an executive discussion. It could be at the senior level that we just talked about. It could be at the mid-level, even at the entry level. It’s a business discussion. That’s what it is.

It’s not about using AI to get the perfect answer for a question and memorizing the answer. As we all know, there’s no authenticity to it. The second somebody catches that, they’re going to ask one follow-up question and then the interviewee has nowhere to go. The reality is it’s just being authentic to each individual and engaging in a business discussion. That’s what it is.

How do I handle situations where I’ve had some kind of failure? I could have been laid off or I could have had something not go well in my past and I get a question that goes directly at that because somebody’s familiar with that experience or they just ask about something where they want me to talk about a situation where I’ve failed. How do you answer that question in a way that’s not going to be self-sabotaging?

Taking Control Of Your Exit Narrative

Probably one of the things that I’m most interested in is the book. I’ve referred this chapter essentially to so many executives over the years who have been fired or let go. The best thing you can do as an executive is get ahead of the narrative. What I mean by that is if you’ve been fired, there’s a human condition where most leaders want to get back into a role as quickly as possible so they can show their other employer that they’re of value and they are attractive to somebody. That’s the worst thing somebody can do.

The reality is, if you have been fired, it’s best in our opinion to take the time, process what happened, and give it some time if you can afford to stay out of the job market. Now, obviously finances matter for every single human. There may not be enough luxury with finances to do this the way I’m going to articulate it, but there’s probably a middle ground somewhere, which will take at least a few weeks to process, decompress. Most likely, you’ve been in a pressure cooker. If you’ve been fired, you’ve felt the pressure. Not the last day you were there, but for weeks or months or years, maybe.

Take the time to get healthy, recharge, and reconnect. After you’ve cleared your brain and you’re not talking about your former employer, every single sentence that comes out of your mouth anymore, then go back to, I’ll say the 3 or 4 of your biggest critics at the company you worked for. Try and get them to open up and ask them for time to give you feedback. The way you set it up, essentially what you want to do as a leader, you want to get them to feel comfortable and safe to tell you what was being said about you when you weren’t in the room.

The way you set it up is, “I’ve taken time to reflect. I made some mistakes when I was there. Whether you agree that you did, whether you think you did, it has nothing to do with that.” You obviously did because you were fired. You have to admit to each of these when you set up, “I know I made some mistakes. I don’t want to repeat the same mistakes. I’m going to be in the workforce for a long time. I’d love to learn from what was being said about me.”

Now, what we’ve seen when people do that, it’s not easy to do, by the way. I will tell you, of all the people I’ve ever shared that framework with to do it, and they’ve all done it. They’ve all come back and said, “That was powerful,” and here’s why. Once you do that, and if they start giving you the truth, the worst thing you can do in that meeting is to try and correct them. If you get somebody to be open and share and trust, just accept it, say thank you, and not a sentence more. Once you get that, if you do, you have the keys to the kingdom now because the two things, you know what is most likely going to be said about you during references or when you explain what may have happened in that situation.

Think about it this way. Those people that may have been detractors or folks that could have sabotaged your career if they got a reference call, most likely went from Red to Yellow. Maybe in some cases, Red to Green. Simply because you were self-aware. You were courageous. You reached out. You admitted you made mistakes. You listened to what I had to say. You didn’t argue with me. You just took it in. Now, when I go to the company that I want to go talk to, I can say, “Here’s what I did. Here’s what I learned. Here’s what you’ll hear.” When the company goes and does references and back channels you, they’re going to hear just what you said. Now you sound super self-aware.

There’s a lot to what you just said. One is the point about being receptive to hearing it and not trying to contest it, but just taking it in because it shows a desire to learn. The fact that you potentially reduce the temperature of their comments because people will call them and ask about references. The last point is, you know what they’re going to say, and you can come up with your positioning of that when you get asked the question in future interviews but it does take courage.

Anybody reading that has had that experience. Let’s face it, I’ve been fired in my career. A lot of people have. The reality is that it’s the best thing you can do. Think about what’s the alternative, do nothing. When you do nothing, you have no idea what somebody is going to say. The people who are Red are going to stay Red, if not even go Purple. The reality is to do something. At least you have a chance.

I want to talk about internal candidates. I know you do a number of searches where you’ve got one or two or a handful of internal candidates and external candidates as well. One of the things that surprised me in the book is that they don’t tend to fare well. I’m curious to hear, and our audience would love to know, why is that? Why do internal candidates tend to underperform in these hybrid selection processes that also include external candidates?

There’s a couple of very common reasons. One, they might give an ultimatum. They may have been hired with the promise that they are a successor to a role. There may have been an expectation when they came in. For whatever reason, if it’s a public company with fiduciary responsibility at a senior level, CEO level, they’re going to want to make sure that they’ve looked and scanned the market. Even at the C-suite levels as well. There’s some time and expectation with that. It might be expected that’s going to happen.

When they find out they may have to compete for it, all of a sudden, they could offer an ultimatum. We’ve seen this happen fairly regularly, where it’s like, “If I don’t get it, I’m leaving.” It’s just a terrible way to play the hand. It backfires almost every time. That’s one. Two is they become very high maintenance. If you engage an internal candidate too early in a process, these processes take place at a senior level. They take 3 or 4 or sometimes 6 to 12 months. If you engage an internal candidate too early in the process, they’re constantly asking for updates of what’s going on.

At the end of the day, this process of recruiting is a need-to-know basis only. They’re not told a lot other than their own candidacy. They’re not told who they’re competing with. They’re not told where they’re at with the other candidates. They become high maintenance. Pushing both of those aside, the other reason is sometimes they just don’t talk about the job, especially if it’s one that’s going to elevate them. It could be into a C-suite role, into the CEO role, or a role that they’ve not had before.

They look at the opportunity to talk about during their interview internally through the lens of the world they’re in, going back to what we had talked about a little while ago. They’re sometimes afraid to take risks. At the end of the day, if the internal candidate basically says, “I wouldn’t change anything. I would do it just the way the predecessor did it.” That clearly isn’t a very compelling argument. Show some empathy to the context of what the other leader had to deal with and where the companies come from.

At the end of the day, every board and CEO and C-suite is looking for new ideas. They’re all looking for growth. There’s no company that’s not looking for growth. How are you going to grow the company? Go back to Fidji Simo’s comment, bring ideas. Show them the way you think. Those are some things that we see with internal candidates. They just don’t take enough risk in the process. Remember, they have the inside advantage because they know the culture of the company. They know whoever is going to come in from the outside, that’s going to be their Achilles heel. They may bring lots more experience, but they’re surely not going to bring the culture fit, style fit that you would.

Do you think, though, that the bar is somewhat higher for internal candidates? I felt that sometimes the hiring manager and the HR person who’s on point or the head of HR have a bias to go outside because if it doesn’t work out, there’s a higher expectation that it might not work out because you brought somebody in from the outside. It’s almost like it’s a bigger risk, a bigger bet to take an internal candidate and promote them.

I view this whole process as a benefit and risk equation. Every single candidate, it’s going back to the ABC framework we talked about and finding out your attractiveness and your value. Every decision in the hiring process is a risk reward decision. How much risk am I willing to take? What type of risk? It’s not just overall risk. Is it domain risk? Is it role risk? Is it a style risk? What is the risk that they identify?

At the end of the day, boards and CEOs and investors, they want to eliminate as much risk as possible for obvious reasons. They want as much upside and as little risk. For somebody to get the role with a lot of risk, there’s probably a backstory there that is unique because it’s usually the candidate that will have the least risk when you’re comparing side-by-side comparisons with the most upside.

Executive Career Management: Got let go? Don’t rush back into the market on the defensive. Step back, gather hard feedback, and own the narrative before others do.

I want to pull the curtain back a little bit and just talk about what this looks like and feels like from your side. How do candidates hurt themselves from the moment of that, even before the moment of that first outreach potentially from you all the way through the process?

There’s a long list, which is why Jeff and I did want to write this book. Let’s just go through a few of them. I’ll give you a few obvious ones and a few ones that I’ve seen in my career. They’ve never been repeated, but it’s hard to imagine they happened. One is they talk too much. When you’re in a discussion, an interview process, be mindful of the engagement. I don’t want to call it human nature, but we’ve all been programmed to just want to sell.

I’m selling you. I want you to know how great I am. I want to tell you how great I am. At the end of the day, nobody tells anybody how good they are. Let the data tell how good you are. Let the information you’ve achieved, the results you’ve achieved, talk for you. As the person interviewing, you decide if the data I just gave you was compelling versus like, “J.R, I’m a great guy. You should hire me. I want this job.” That’s not compelling.

Talking too much and not being relevant with what you’re talking about for the person who is hiring, because they’re a buyer, let’s face it. You’re a buyer as well, but you’re a seller in some ways. Logistic things, they go silent. You’re trying to reach them and they just don’t reply. It could be for very legitimate reasons. They’re overseas. They’ve had a fundraising round, whatever it is but it’s how to be super communicative, asking for feedback. This is one that shocks me how few leaders ask for feedback. The more senior you get, it’s hard to ask to have the mirror held up to you.

At the end of the day, the hundreds or thousands of people that work for you are all trying to tell you how great you are and how wonderful you are. The reality is, every single leader, when they’re going through a process like this, needs a truth-sayer. Somebody that will hold the mirror up to them. Ask for feedback. Ask for feedback after you’re done with the discussion. Ask for feedback from the recruiter who brought you in. Ask for feedback from the person you met with. Keep showing that mindset, that willingness to learn, and that curiosity. That’s important.

A couple that I will share with you that they’ve never repeated, so it will never happen again, I have to imagine. This is a leader from a while ago. When business cards were handed out, though, they’re not anymore, but this leader took the business card of who he was meeting and set his drink on top of the business card as a coaster. It didn’t go very well. Another one that was kind of unique was when you go into a conference room. There’s a moment where, unless you’re predetermined where you’re going to sit versus the person that’s interviewing, going to sit.

I don’t recommend as the interviewee that you take the head of the table. That’s definitely not recommended. However, people do it. Those subtle signs of etiquette, those subtle signs of consideration, all matter. All of this matters. It’s sometimes not just what people think, “I nailed the interview, but guess what? They were rude to the receptionist when they walked in,” or some other silly thing happened. Those are all things that could ruin a candidate.

This continues through into the offer process as well.

The Unseen Traps Of Executive Hiring

It does. The offer process. A couple of things that trip people up late in the process are one, negotiating. People who get too aggressive in negotiating. That can take lots of different forms, but sometimes there’s a confusion between what offer even means because there’s multiple uses of the term offer. There’s a framework of an offer, a verbal offer, a written offer, or a signable offer. They’re all very different. People get very confused when they throw the term, “I got an offer.” The only one that matters is you get a written offer and is it a signable offer. That’s the only thing that matters because you know your value.

At least for that company, your value. You have a data point. When they try and negotiate too aggressively because they think they have the opportunity in the bag, we’ve seen many opportunities where the company’s cut bait because what they’re viewing you as, and they’re watching you is, if this is the way this leader is going to show up to negotiate, is this how they’re going to show up internally or with our clients or customers? We’ve seen that happen more than a few times.

The other way is when they resign. We talk a lot about the resignation process in the book and lay out a step-by-step program to do it well. People that don’t do it well, they get counter offers. They accept counter offers, and they leave the company that gave them the offer high and dry. Jeff and I had a recent example of this where we were negotiating for a public company CEO role. The person had a written offer, was negotiating it, and said, “If we can get the compensation right, I’m going to take it.” We told that to the entire board. That was on a Friday or Thursday. That following Monday, that individual took another role in another company. Never told the company that they were negotiating with and literally just ghosted them. That is not the way to do it.

You have a lot of examples in the book. Don’t burn bridges.

For that same search I was just talking about, I’ll give you a perfect example about not burning bridges. A name came up to the search committee on this CEO search. Somebody on the search committee said, “I knew that individual twenty years ago, and that person was a jerk. We definitely are not going to consider that person.”

Think about that for a second. Somebody that knows where they were in their career acted like a jerk, had that reputation, burned that bridge. Twenty years later, that individual will not even know what is being said about him or her when they’re not in the room. Whether that person wanted the job or not, they’re not even getting the opportunities because that’s the reputation they built.

Kelly, thanks for doing this with me. I’m sure your book will be incredibly beneficial to anybody who’s in the job market and we all are at different points in our career. Getting these interactions with search firms like Heidrick is important for people. I’m sure this will be an episode that a lot of people will find very useful. Thank you for doing it with me and best of luck with the continued launching of your book.

I appreciate you having us on. I hope that your readers get a lot of value from it. Hopefully, it’s a value.

Wrapping up the conversation just now with Kelly, let me offer a few takeaways. Most importantly, manage your career before you need to. Don’t wait until you’re miserable, unemployed, or desperate for change to understand your market value, build your network, establish relationships with recruiters, or think seriously about what you want next. Career management should be ongoing, not episodic. If you’re a regular reader to this show, this is something that I emphasize all the time and feel strongly about.

Second, know your story, but don’t turn it into a script. Your resume is going to tell people what you’ve done. Your job is to explain the context, the impact that you created, what you learned, and why that experience makes you the right person for this particular opportunity. A lot of people know that they’re supposed to tell stories in interviews, but if you just tell the same story again and again, and don’t link it to what that person in that seat who’s interviewing needs, then you’re missing an opportunity to connect with them and to show them that what they need and are the right person for that role.

Third, remember that you’re evaluating the company too. The objective isn’t just to get an offer for the sake of getting an offer. It’s to find a situation in which your strengths, aspirations, values and definition of success align with what an organization needs. Kelly talked about the importance of going into a discussion with a recruiter or a company with clarity on that. If you have that, then you’re going to be able to have a much more informed conversation about whether this situation that you’re talking about is right for you.

We build our careers one role at a time. Though we’re changing jobs more often than we used to, you don’t get an infinite number of career tries. You’ve only got a finite number of them. You want each one to count and be right for you, to contribute to your broader success, and to leave you feeling happy and fulfilled every day.

Finally, is just this idea of how you show up throughout the process matters incredibly. It is not just the interviews. Your phone conversations, how you respond to email or tone, or whether you put your drink down on somebody’s business card or sit in the seat at the head of the table. A couple of things that Kelly mentioned in the course of our conversation, all of that gives the company that you were interviewing with data.

You want that data to be good data. You don’t want it to work against you. Yet a lot of people self-sabotage intentionally if they’re trying to be too hard a negotiator or unintentionally by just doing something that rubs somebody wrong. I’ve certainly seen this in my own experience. It’s a great conversation, lots of practical advice, especially if you were in the job market, but the point is you were always somewhat in the job market.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with somebody who may be looking for a job or just wants to manage their career better. In other words, all of us. You can also sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks for tuning in.

Important Links

• Kelly Kay on LinkedIn
• Heidrick & Struggles
• Jeff Sanders
• Show Up to Win: How to Land the Leadership Role You Want
• OpenAI
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About Kelly Kay

Kelly O. Kay is a partner in Heidrick & Struggles’ San Francisco office and the global managing partner of the firm’s Enterprise Software and AI Practice. With 22 years in executive search, Kelly conducts searches worldwide for a wide range of technology companies, from high-growth private and public enterprises with revenues up to $100 billion. Kelly specializes in senior go-to-market leadership roles, including board, CEO, COO, CRO, and worldwide sales. He co-founded Heidrick’s Sales & Commercial Officers Practice and is a leading voice on executive talent trends in B2B software. Before executive search, Kelly was a partner at the Center for Corporate Innovation (CCI), a CEO development and strategy organization sponsored by McKinsey & Co., and earlier held senior roles at IBM Corporation and Gemini Management Consulting. A sought-after talent adviser and public speaker, Kelly’s writing has appeared in Harvard Business Review, Forbes, and The Wall Street Journal. His HBR article on resignation best practices “Leave Smart, Land Well” was based on a national survey of more than 6,000 CHROs and senior executives and became one of the publication’s most widely read pieces on executive career management. Kelly holds an MBA from the University of Southern California’s Marshall School of Business and a bachelor’s degree in Marketing from the University of San Francisco.

You may not think of yourself as a salesperson, but every day at work, you’re selling something: an idea, a proposal, your capabilities, or even yourself.

In this episode of Career Sessions, J.R. Lowry sits down with sales expert, author, and longtime podcast host Andy Paul to explore what the rest of us can learn from great salespeople about influence, curiosity, and human connection.

Andy explains why the best way to persuade someone isn’t to push harder, but to understand what matters to them. He shares how asking better questions and truly listening can strengthen relationships, why curiosity is often trained out of us as we move through school and work, and how to avoid making conversations about ourselves.

The conversation also moves beyond sales to a bigger career question: Are you building the career you actually want, or simply following someone else’s playbook? Andy discusses why success is situational, how to find environments where you can be yourself, the importance of choosing the right boss, and why it’s sometimes better to leave a bad fit rather than keep trying to make it work.

Along the way, Andy shares lessons from nearly five decades in business, and a reminder that there’s no age limit on taking on new challenges.

In this episode, you’ll learn:

• Why everyone is selling, whether they realize it or not
• How curiosity can make you more influential
• The difference between listening to understand and listening to respond
• Why great questions create stronger relationships
• How to find work environments that fit your strengths and values
• Why you should define success on your own terms

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 athttps://pathwise.io/podcasts/andy-paul/.

Watch the episode here

Listen to the podcast here

Stop Following Someone Else’s Career Playbook, With Andy Paul

You may not think of yourself as a salesperson, but every day at work, you are selling something. You’re interviewing for a job. You’re asking for a promotion. You’re influencing colleagues. You’re convincing your boss to try something different. According to our guest, the best way to do that isn’t just to be more persuasive. It’s more about becoming more curious, more authentic, and better at understanding what matters to the other person that you’re trying to persuade.

Andy Paul has spent his career focused on helping others become better salespeople, working with everyone from startups to some of the world’s largest companies. He’s the author of a number of books, including Sell without Selling Out: A Guide to Success on Your Own Terms. In his own podcast, he has hosted more than 1,300 conversations with some of the leading thinkers in sales and business.

Our conversation isn’t about being a salesperson. We’re going to talk about why curiosity is an underrated career skill, what great listeners do differently, why following someone else’s playbook can hold you back, and how to build a successful career without trying to become someone you’re not or live in circumstances that aren’t right for you. We’re also going to explore a question that matters whether you’re 25 or 35. How do you stop following the career path that you think you’re supposed to have and start defining success on your own terms? I’m J.R. Lowry. This is Career Sessions. Here’s my discussion with Andy.

Andy, thanks so much for being with me on the show.

Thanks for inviting me.

I’m looking forward to it. Why don’t we dive right in? You have massive experience in the sales space. You’ve written books. You’ve done multiple podcasts in that space as well. For somebody who’s not a salesperson, convince them that they are selling every day.

The Hidden Reality Of Daily Selling

Look at it two ways. If you’re in a customer-facing role in any regard, whether you’re in sales or customer service, customer support, every interaction with a prospective buyer or an actual customer is a reflection on you. The customers take that as an example of what it’s going to be like to work with your company. The way people experience you and every time you have a chance to interact with them makes a difference and builds to its perspective or opinion someone has about you or your company.

My job is even at customer services. If I’m talking with a customer, what help do they need from me? How can I be the most helpful to help them achieve what they want to achieve in the shortest time possible? That’s our goal. How can I make the most effective use of my customer’s time? In my mind, there’s no such thing as an insignificant interaction with the customer because they all contribute to their perception of you.

That’s very fair. There’s also the element of just us. We are selling ourselves when we go to work every day. Hopefully not selling our souls, but certainly selling ourselves.

Whether people like the terminology or not, we all do carry a brand. Some of us consciously develop it and others don’t. People are forming opinions of you. If you have certain desires at work, you want to progress through your career or you want to achieve certain things. You have to be mindful of that. Again, there’s no such thing as an insignificant interaction with the people that matter. We increasingly, in our lives, get our work done through other people. Part of our job is, in order to succeed at what we’re trying to do is, we need to have people help us. How do we persuade people or influence people to devote some other time to helping us achieve certain things?

You’ve worked with a lot of salespeople over the course of your career. What can somebody who’s not a salesperson learn from a salesperson about how to do all the things you were just describing in terms of influencing and collaborating without coming across as aggressive or fake or manipulative?

One of the things that I live by is I’m working with you as I’m trying to understand, not just know, but understand what are the things that are most important to you that you’re trying to achieve? How can I help you get those? If I operate in life, it’s saying, my job is to understand the people that I’m dealing with. They all have things they’re trying to achieve that are important to them.

When I’m coming to pitch an idea or something, how does that align with helping them achieve these things that are most important to them? The central part of what I’m trying to do is understand this person, understand what that is. You’re so much better off. As you come from a perspective of, “I’m here to help you.” Maybe we can help each other, but I’m here to help you. I’m here to listen and understand. If you can do that, people think you’re there to serve them as well as yourself, then you’re a much better footing.

I’ve heard that the construct of approaching things with a sense of generosity is applied in networking. Certainly, that’s where Keith Ferrazzi made his name, among others. It’s this idea more generally of negotiations, trying to find a win-win. Not that you’re necessarily going to work every day to negotiate something. The concept of it all feels very similar in terms of trying to find the win-win.

I would go a step beyond that, though, because if you’re saying, “I want to understand what’s most important to you.” I’m not thinking about myself in that regard because I know that if I can help you, I am going to get perhaps what I want, what I’m looking for, and the help I need. If I’m thinking about the win-win, that tends to fall into quid pro quo. I’ll give you something if you give me something, which is the opposite of generosity. Generosity is like, “I’m going to give without the expectation of return.” When you are generous, you do get the return.

I think I said it badly earlier in terms of describing it as win-win, because I agree with the idea that you are approaching this saying, “How can I help you?” If you do that enough times, it will all come back to you.

Zig Ziglar said, “If you help enough other people get what they most want out of life, you’ll get what you want out of life.”

Curiosity In Sales: Empathy isn’t just about sharing a feeling. Learn how cognitive empathy helps you understand what truly drives your team.

It’s very well said. You were just describing a use of curiosity in terms of trying to understand what the other person is trying to get. Whether you’re in a formal sales or not a formal sales situation. Curiosity is central to the way that you think about how to manage your career and your day-to-day work life. How else does it factor in for you?

Unlocking Cognitive Empathy In Conversations

It operates on multiple levels. One is general curiosity about the world and staying informed and abreast of what’s going on and being a lifelong learner. That’s certainly an aspect of curiosity. The level I look at is more important in the long term. It’s being curious about other people. It’s making an effort to truly understand them. I write about this in my book as there’s this gap between knowing something about someone and truly understanding. Unfortunately, we reinforce this gap.

Even though there’s a segment of the population now politically in the United States that thinks empathy is a weakness. Empathy is critical, but we approach and teach empathy the wrong way. What we do is we say, “It’s important to walk a mile in someone’s shoes.” You understand what they’re feeling. We can’t help someone if we just understand what they’re feeling. There’s this difference between compassionate empathy and cognitive empathy.

Passionate empathy is to say, “Walk a mile in someone’s shoes. I understand how they’re feeling.” Whereas cognitive empathy is understanding why they feel the way they do. Now, if I understand why you feel the way you do, then that gives me information to be able to help you. As long as I just know how you’re feeling, that doesn’t give me a clue as to what’s at the root of it and how I can help you.

For me, curiosity is going beyond this knowing, “J.R feels bad about this.” I don’t go that step further and make sure I understand it. Expand that gap between knowing something, understanding it, and understanding why. It requires persistence in questioning and curiosity to get to that point where you develop a true understanding.

Listening has to be a big part of that. What do most of us misunderstand about what it means to truly listen? We think we’re listening, but we’re not.

Breaking The Habit Of Listening To Respond

The biggest thing that I see is that we tend to make conversations about ourselves. There are two things you see. One is, we listen to respond. This is one of the biggest things I see when I’m coaching people and working with people in the sales environment or even in real life. People have a tendency to want to make things about themselves. That is the opposite of what you’re trying to do to truly understand this person you’re talking to.

A perfect example of this is and you may have heard this example before. It’s this idea that when you can respond to someone, your responses fall into two categories. One is called a shift response and one is a support response. Typical example, coming to work. You talk to a colleague and you say, “How was your vacation this summer?” You say, “I showed up at this resort with the entire family,” and they didn’t have a reservation.

Now, what most people do is they say, “That’s horrible. That same thing happened to me.” What you’ve done is you’ve shifted the focus of listening from them to you. Whereas, a support response, “That must be horrible. What did you do next? How did it get resolved?” You turn it back. What’s the next question? Again, you’re trying to understand the situation. When you’re listening, that’s a critical thing because you’re thinking, “What’s the next thing I need to learn in order to understand that?” Extend my curiosity.

Whereas, we tend to turn off our curiosity. There’s very simple things you can do to practice this. One thing I encourage people to do, if they’re struggling with this concept, I say, “Go to a social setting. You’re going to meet somebody new and see how many questions you can ask that person before you have to say something about yourself.” Be able to ask at least three questions before you have to say something about yourself. If you practice that, you get in the habit of saying, “I’ve met somebody new. I’m curious about this person. What can I learn about them?”

That’s just one example that helps you become a better listener because your second and third questions are going to be based on the answer you got on the first one. Simple techniques you can teach people. If you practice these, they become ingrained but just something simple. You ask somebody a question, they give you an answer. “That’s interesting. Tell me more about that.” The response to the person that gets that question is, “This person’s interested in me.” There’s been some studies on this saying that the best way to make yourself interesting to someone else is to be interested in them. If our goal is to try to build some connection at a personal level, that’s a great way to do it.

That exercise that you just talked about is a good one. I will sometimes go through an exercise similar where I try not to say anything about myself for as long as I can get away with because it forces you to learn how to ask those follow-up questions, which is an important skill to have in life. You can also fall back on some of the things you were talking about in terms of like, “Then what? How did that feel? What happened next?” Similar questions that are general enough that you can have them in your repertoire and use them regularly.

When I wrote about the shift response, support response, I got an email from somebody who read the book. They said, “I got back from family Thanksgiving. I was just listening to the conversation. It was all shift responses. When I started practicing support responses, it’s amazing how the conversations start changing.” Again, part of the era that we live in, so much of the focus is on us. Social media is all about us. You have to make an effort to step outside that because that’s the paradigm that people are following these days.

That brings us to thinking about what we were just talking about, questions. What separates a great question from a more mundane one? Whether you’re in a sales situation or at a networking event having a conversation.

The Art Of Asking Better Questions

Have the other person talk about themselves. You want to have people feel comfortable to talk about the things that are important to them. Your job is to understand what’s most important to the other person and help them get that. That plays in every relationship you have in this world. What’s the way to be a better partner, a better spouse? To make sure you truly understand what’s most important to the other person and then help them get that. How do you be a better parent? Understand things that are most important to your kids. Help them get that. I can go through a laundry list of situations where the same thing applies.

I’m curious to get your view as to when you want to just focus on getting somebody to talk about themselves and when you want to focus on getting them to think about themselves, if that makes sense. Ask them a deeper question that’s going to push them perhaps a bit outside their comfort zone.

You have to earn the permission to do that and to get to that point. In my last book, Sell Without Selling Out, I talk about these four core elements of building these trust-based relationships, ability to connect with another person, to be curious about them, truly understand them, and be generous. You have to build that level of trust to start getting the permission to ask those questions. That’s worth doing.

If you’re trying to develop a business relationship, the relationship is not going to go anywhere until somebody reveals something about themselves that you can’t read on a website or that’s just not normally available because that’s what you’re trying to get to. It’s to be able to reveal something about themselves that’s not commonly known.

The deeper relationships are built on that knowledge, but people aren’t just going to give it to you. You have to earn the right to do that. I sound like everything’s so conscious, but we want to get to a point where these things are talking about this connection. The curiosity is ingrained and not performative. If they’re performative, then people sense that you’re inauthentic.

Curiosity In Sales: Curiosity shouldn’t be performative. Here is how genuine inquiry builds trust across teams.

They do. Being genuinely curious and being performatively curious are going to feel like two very different things to people, to your point.

The problem with curiosity, and there’s been studies done on this. I’ve had somebody once challenge me, because I believe, based on my own research and reading, that we’re all born with the same amount of curiosity. Our life tends to train a certain amount of that out of us. I found this especially true with boys because curiosity is viewed as disruptive. You’re asking too many questions. Maybe it happened to you in your life. I know it happened to me a couple times in my life. It’s like, “Enough with the questions. Do what you’re supposed to do.”

That carries on into life where people subconsciously have been coming to believe that, “If I asked too many questions it’s a negative,” and it’s not. It’s coming from a sense of real interest and true interest, then people will let you ask as many questions as you can. I started my career in sales almost 50 years ago now. I’m selling large computer systems to business owners. I knew nothing about computers and nothing about business. It’s a great combination.

I was genuinely curious. This was my first year at sales or it was my MBA. I go and talk to these CEOs and these founders of these companies. I was genuinely interested in how they had built the company, what they were doing, what was next for them. When I approached it from that perspective, I got all the time in the world I wanted with the prospects. That lesson stuck with me.

The other reason that we get enculturated is to not ask so many questions, because especially when we come into a work environment, we feel like we have to have all the answers. Being curious is almost like an admission of weakness.

Yes, it is unfortunate that is the case. I see it all the time in consultant work. The new vice president of sales needs help, but is afraid to admit they need help because, “Wasn’t I just hired because I have all the answers?” No. Somebody hired you because you have potential. Not because you have all the answers, but people find themselves backed into that corner where they refuse to ask for help. That is unfortunate.

You can’t always see ahead of time when you come into a job, but it’s one of the things for people that are job seekers that they need to think about. Success is situational. I can take somebody that is great, performing well at company A and moving to company B, and they won’t succeed. It’s the same level as I did before. They’re the same person, same set of skills. Maybe even selling very similar products, but the environment is different.

It’s important when you’re looking for work, you’re looking for the next assignment or next gig. Is this the right situation for me? Is this an environment I can succeed in? Is this the boss that’s going to be able to help me get to the next level? You should sense a lot of that through the interview process you’re going through. It’s like, “Do they think they just have this nailed or are they open to giving me the freedom, flexibility and the autonomy to succeed in a way that aligns with my strengths and my values?”

That’s important and brings us to another topic that I wanted to discuss with you, which is this idea of finding a way to be yourself. You’ve described yourself as an introvert who didn’t necessarily fit all the stereotypical images of being a successful salesperson. How did you figure out how to make that work for you in a way that was authentic to who you are?

Why Your Career Success Is Situational

Trial and error for one. What I learned was this lesson I just talked about, is finding the right situation. I was about 30 when I was between jobs. I worked for somebody that was a horrible boss. It dawned on me that as much as the company’s hiring me, I’m hiring a boss. I’m looking for someone that’s going to be able to help me learn what I need to learn in order to take the next steps in my career and will support me in doing that. That became most of my sole focus.

The roles that I was interviewing for and trying to get are like, who’s this person that I’m going to be working for? Will they give me not just their knowledge and their experience, but will they also give me the autonomy to try new things, to bring myself to the job? I found that in almost every role I’ve been in, that’s been important. Those where I’ve been able to express myself and the boss wanted me to express myself. I did much better at them.

There was a great quote and I’m going to paraphrase it. I’m a huge soccer fan. If you’re in London, I don’t know if you’re a Premier League fan. This one soccer coach said, “What I want is players who are going to show up and bring their personality to the game. Express themselves through how they play.” I thought it was a great way to talk about it. It’s the opposite of what so much of what corporate America is about. I want you to show up and fit into our process.

I want you to be this interchangeable cog in our machinery. That was just never going to be me. Again, after a few failed experiences in my twenties, once I turned 30, then I was like, “This is what is important.” By and large, I was able to escape when I started my own company, and I was 45. For this middle part of my career, I was able to navigate and find those environments where I was working with smart, talented, capable people that just wanted to say, “Here’s the job. Go figure it out.” That was great. That’s what I wanted.

Using your example of the Premier League coach who said he wanted players to bring their personalities to the field as that player or as a player in a corporate environment, how do you figure out the balance between bringing your own personality to bear but also fitting into the system? The team that you’re playing for, the system that you’re on in a corporate environment.

I don’t think they’re antithetical. I’m sure you see this too in managers, especially younger managers. They’re afraid to step outside the tightly circumscribed bounds of what they think is going on. They have to be more enforcer types and make sure people are compliant with this process. As if they’re afraid to individually manage the people on their team. I see this again in the sales world all the time. It’s like, “You got to follow the process,” but you got this person who’s got these unique skills. Develop them individually. They’re like, “I don’t have the time.”

I said, “What do you mean you don’t have the time? This is your job as a manager.” You’re only going to succeed if they succeed. It’s to help them become the best version of themselves. I’ve seen the shift in the last 20-25 years as to, “Everybody’s got to comply with the process.” It’s so self-defeating because, certainly in the sales world, chapter and verse in enterprise sales, B2B enterprise sales, where people become so focused on the process that they think the process is good and the people are the failures, when it’s the opposite.

It’s the process that’s failed. It’s too easy to point the fingers at the individuals that say, “The salesperson is no good.” When you take that approach, the process is great and the people are failures. You’re failing as a manager. You’re failing to develop them. You’re failing to give them the instruction, inspiration and examples that they need in order to succeed.

Back to your original question. You have to put yourself in a situation where you have the freedom to experiment. As an individual, that’s the critical thing, an environment where I can try new things and bring the best of me to it. Sometimes it involves leaving the situation you’re in and going find another one. Very few people have employment contracts. Go find a better situation.

One of the hardest things about this is when you’re sitting in that job interview. How do you figure out whether this system is going to be a good system for you? There is a system. I hear your point about letting people bring out their individual strengths and I’m completely aligned with you in that. One of the things that I think about and I don’t think I’ve come up with a great answer for yet is, how do you sit in that job interview and suss that out in a way that is not just the tell me about your culture and get the same boilerplate answer?

Curiosity In Sales: You are not just interviewing for a job. You are hiring the boss who controls your daily autonomy.

The hard answer is you can’t. Things are a guarantee. I was talking to a client of mine, a coaching client, where they lied to me in the interview process and I’ve experienced that. I’ve been misled. This was interviewing for a senior position where they showed me a false set of financials. The answer is you can’t be afraid to make a change. It’s okay to say, “I made a mistake.” Why torture yourself for 6 months, a year, or 2 years in an environment that’s not going to be a fit?

It’s not like in the old days where if you change jobs too frequently that used to be held against you. If you find yourself in a bad situation, it’s better to cut it off short and go find that next thing because you just learned a lesson. Don’t make it worse by staying in there because you’re not going to be happy. They’re not going to be happy. It’s worse to be in some place in a year and not have anything to show for it as opposed to cutting the cord quickly and finding something.

More generally, and you write about this in your book. How do you pursue your own definition of success versus the one that gets put onto you or ascribed to you?

Hiring Your Next Boss Deliberately

It starts with defining what you want out of any situation, what you want out of life. I was having this conversation with a client. Bemoaning the fact that they’d had an opportunity to join a reasonably hot AI startup that had announced they were going to go public. They were saying, “They had offered me a job and I hadn’t taken it. I regret not having done that.”

We had talked at the time about it, and I said, “The things that they weren’t offering were the reasons that you didn’t take it. You weren’t going to have the same autonomy that you wanted. You were going to have to relocate. The money wasn’t good enough to replace what you’re currently doing now, but what they were offering was the mythical upside of our equity,” which they weren’t even offering enough to almost compensate for the money this person wasn’t going to make in their salary.

It’s like, “You chose because you wanted autonomy. You wanted the freedom to be able to make the type of money you want to make. The situation wasn’t going to allow you to do that. You made a good decision.” It’s harder when you’re earlier in your career. You gain more perspectives. As you get older, you get a family of obligations, whatever that influences your decisions. You want to be clear headed about, “What are the things that enabled me to go to work and enjoy it?” For me, autonomy was always one.

Even as an individual contributor, one of the things that attracted me is sales in the first place, because I certainly wasn’t a salesperson by nature, inclination. In my first sales interview, the boss I’m interviewing with said, “You’re going to be the CEO of your own territory. That’s the role. That’s why you have to look at it. You’re the CEO of your patch.” That’s like music to my ears. It’s like, “I’ve got control over how I’m going to do this.” That just stuck with me. I always wanted to find those situations where I could enjoy that similar type of autonomy.

You’ve talked a little bit about this already, but what else would you want your younger self to know that you know now or advice that you would give somebody who’s in the early part of their career?

Stress less. You do the best you can. Try to learn as much as you can about the field and the world you’re in and try to have fun. Fun was certainly the element of my career. I’ve had a lot of fun and have had a lot of fun throughout my career. A lot of variety, which was important for me. In contrast with my dad, I worked 36 years with one company and I liked the variety. That’s one of the reasons I started my own consulting company.

The bottom line is I’ve had a good time doing it. I’ve made an effort to work with smart people. I wanted to put myself in situations where I was challenged. I went for a history major. I sold big computers. I don’t think about big computers, big or small. I spent fifteen years in the satellite communications business, selling highly complex technical products. I know nothing about them, but I put myself in a situation knowing I was going to have to learn and it was going to challenge me. I had a good chunk of selling large systems overseas. Again, that was just so much fun.

It’s having a sense of enjoyment of what you’re doing. We all have obligations. Again, try to find those situations where you’re going to be challenged and you look forward to that challenge. Somebody asked me once, how did I choose a particular job? I said I chose this one because the boss scared me. They said, “What do you mean scared you?” I said, “I knew it was going to be a challenge. This guy was so smart.” Especially about sales and he turned into a lifelong mentor.

He was just going to force me to think about everything I did and I loved it. It became so much better as a result and so much smarter in so many different dimensions because of just the intellectual rigor of that. For me, that was important. I wanted to work with painfully smart people. I’ve always tried to do that in my career.

I appreciate your thoughts and appreciate some of the perspectives you’ve brought to taking ownership of your career, being who you are and figuring out who that is and finding situations that allow you to be your best self. Thank you for being with me and sharing your perspectives. I wish you well and whatever is coming next for you, which is probably a lot more variety.

Redefining Success On Your Own Terms

I speak in chapter with you and I talk about chapters before we started. Career is a series of chapters. I’ve been working on my first novel. I’ve always wanted to write an espionage thriller, so I’m working on that. Another sales book I’m working on now. I’ll be stepping back into the sales thing but again, I’m always trying to do it on my own terms. These are the types of challenges you want. I don’t ever envision stopping or not doing anything, retiring completely.

I wouldn’t know what to do with myself. It’s good to pick new challenges and learn something new. My first of these 1,300 podcast episodes, I didn’t publish the first one until I was 60. I didn’t publish my first book until I was 50. There’s no limitations based on age. It’s just based on your curiosity and desire to learn new things. That keeps life fun and interesting.

Yes, it does. Thank you again.

Thank you.

A great discussion with Andy. Let me cover some wrap-up points to help you take away some things from the conversation. First is to recognize that we are all selling, whether we realize it or not. Anytime you’re pitching an idea, interviewing for a job, asking for a promotion, or trying to influence a colleague, you are asking someone to make a decision based on what you are saying to them. The best way to influence that decision isn’t pressure or clever persuasion. It’s understanding what matters most to the other person.

Second, lead with curiosity, not certainty. Some of the most effective people don’t worry about having all the answers, despite the fact that’s what many corporate cultures seem to want to promote. They’re the ones who ask the best questions and then genuinely listen to the answers. They are truly seeking to understand. Curiosity helps immensely with this. It allows you to understand other people, to challenge your assumptions, to uncover things that otherwise you might have missed. The third point is to build your career on your own terms.

Learn from successful people, but don’t assume that you need to be like them. Understand your strengths, develop your own approach, be deliberate about defining your own version of success and what you need in your life. Ultimately, taking ownership of your career means choosing your path rather than simply following someone else’s playbook.If you found this conversation valuable, please subscribe, leave us a review, and share this episode with somebody who’s looking to become a better leader or build a stronger career. You can also sign up for my membership community, PathWise and our newsletter PathWisdom. Thanks for tuning in.

Important Links

• Andy Paul on LinkedIn
• The Win Rate Podcast with Andy Paul
• Sell without Selling Out: A Guide to Success on Your Own Terms
• Keith Ferrazzi
• PathWisdom Newsletter
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• PathWise on X
• PathWise on Facebook
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• PathWise on Instagram

About Andy Paul

Andy Paul is a sales expert, author, speaker, and podcast host who has spent nearly five decades studying what makes people successful in sales, business, and their careers. He is the author of several books, including Sell Without Selling Out: A Guide to Success on Your Own Terms, and has worked with companies ranging from startups to some of the world’s largest organizations. As a podcast host, Andy has conducted more than 1,300 conversations with leading thinkers in sales and business. His work emphasizes curiosity, listening, generosity, and authenticity, as well as helping people succeed without sacrificing who they are in the process.

What if you achieve everything you thought you wanted in your career, and still find yourself wondering if that’s really all there is? Former Vertex CEO Jeff Westphal joins host J.R. Lowry to discuss how you can build a Work Life Worth Living when traditional status isn’t enough. Jeff Westphal spent two decades as CEO of Vertex, helping grow the company from roughly 75 employees to more than 1,000 and increasing its value fortyfold. Along the way, he started asking deeper questions about purpose and why listening can be far more powerful than having all the answers. He shares how an intense focus on reflection transformed his leadership and helped him create an environment where employees felt truly invested. They also examine how rapid changes in AI mean distinctly human qualities like empathy, judgment, and connection will define our professional future. Whether you’re rethinking your path or leading a team, this conversation will help you reflect on what truly makes your career meaningful.

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/jeff-westphal/.

Watch the episode here

Listen to the podcast here

Success Isn’t Enough: Building a Work Life Worth Living, with Jeff Westphal

When people think about career success, what usually comes to mind are things like promotions, bigger paychecks, and impressive titles and maybe building a company. Those things certainly matter. I would imagine that some of you have reached goals that you’ve probably worked hard to achieve, only then to find yourself asking afterwards, “Was that it?” My guest believes that’s one of the most important questions that any of us can ask. Jeff Westphal spent two decades as the CEO of Vertex and led the company through a 40X growth in value and from 75 employees to more than a thousand by the time of his retirement.

By almost any measure, he’d achieved extraordinary professional success but along the way, he also began asking himself deeper questions about meaning, purpose, fulfillment and what truly makes a work life worth living. Those reflections became the foundation for his new book, which is called A Work Life Worth Living.

In our conversation, we’re going to explore why achievement alone isn’t always satisfying and how to build a career that’s both successful and meaningful, what leaders can do to create workplaces where people thrive, and why these questions are becoming even more important as AI transforms the future of work. Whether you’re just starting your career or questioning your next move or wondering how to make your work more fulfilling, you’re going to find a lot to reflect on in this conversation. Ironically, Jeff is very big on reflection. Here’s my discussion with Jeff.

Jeff, welcome and thanks for joining me.

Good to be here.

I’m glad to have you on as well. Let’s dive right in. I know you’ve got this view and you write about it in your book that a lot of people feel successful on paper, but still feel like something is missing. You experienced a bit of that yourself. It would be great to hear your own experience when you had that first clue that success alone wasn’t everything for you. It wasn’t enough.

It’s interesting. It’s not like it wasn’t enough. I wasn’t looking for more. I was succeeding to the extent that on paper, at a cocktail party at 28 years old, I would have felt like, “I’m doing as well as anybody here.” I had multiple promotions. I started at my father’s company and sales were doubling twice. I was leading sales and marketing. Not all due to me, but still I felt like I was contributing meaningfully. I was introduced by one of our salesman’s father-in-law’s colleagues who had become a certified seven habits facilitator. Covey’s 7 Habits of Highly Effective People.

Questioning The True Purpose Behind Your Hard Work

I meet this very poised gentleman who was a former executive at DuPont, the big chemical corporation. He says very nicely, “Why are you working so hard?” I was like, “Is that a trick question? To have more sales?” He’s like, “Why are you wanting more sales?” I’m like, “This guy can’t be serious. What do you mean? Of course you want more sales.” He goes, “I get that, but why do you want more sales?” I’m like, “What is this?” I was literally confused. This man is so calm and smiling at me then he says, “How do you intend to contribute to the greater whole?” I’m thinking, “What is he talking about? Greater whole of what?” I’m like, “I got to know what this guy knows.”

Why Seeking First To Understand Changes Everything

He just helped me realize for the first time that my assumption that I basically knew what I needed to know was completely off base. He gave me the 7 Habits book. In it, I learned about seeking to understand, then I tried that with my wife when we were debating going away for the weekend. I’m like, “I wonder what she’s thinking.” I’m leaning over the chopping block in our kitchen. I’m like, “What is she thinking? Don’t try to convince her.”

All of a sudden, I’m like, “She’s worried about the children. She’s thinking, “How are they going to eat?” I’m like, “We’ll figure it out but she’s worried.” At the time, we had a 4-year-old, a 2-year-old, and an infant. I want to go camping for the weekend. I’m thinking no problem just like when we were dating. That was a huge epiphany. Between 28 and 30, between experiences like that at home and the questions this man was asking me, my whole world got turned upside down, basically. I started realizing that instead of knowing a lot, I knew almost nothing.

I wouldn’t call myself a 7 Habits disciple. The book kicks around this house somewhere, but certainly that point about seeking first to understand, then to be understood is very simple, which is the whole of that book. It’s also very powerful because we spend so much time thinking we know the answer or wanting to get our point across that we stop listening. We stop observing. That’s what that point is about. You are getting it in both those ways.

He was pushing you to observe more deeply about why you were doing work. Not just for the goals, but what was the real reason. Your conversation with your wife and stepping back and making sure that you understood where she was coming from, which you clearly needed to step back and give thought to.

It’s like a 2X4. What was shocking wasn’t so much what she cared about. That was obvious once I saw it. It was an instant recognition that I never realized before. Ostensibly, I’m a successful guy growing and doing all these things. I had no idea. My next thought was, “What do the employees think? I wonder what they care about.” I was literally a different person at work on Monday morning.

How so?

Building Investment By Giving Up Easy Answers

I went from being decisions while you wait to thinking the measure of my success was how hard I could work to help people by giving them the answers they’re looking for, because I was in a line leadership role at the time. I just realized I don’t even know why they’re asking. The line outside my door was there just like it was most days. Not all day long, but during the day, 2 or 3 people would be coming by. Instead of saying, “Go do this.” I was like, “Why do you ask?” They’re like, “It’s because of so-and-so.” I’m like, “Why is that?” I was genuinely curious, like, “What is bringing you here?”

When they started sharing, it was like, “I’ve been making decisions with practically no information needed to make the decision and the notion that they should have any say in the decision that they were going to implement was a couple of years in the future.” With the help of my mentor, I had that epiphany. He says, “How do you plan to build spirit and willfulness among the stakeholders? He’s using an ancient esoteric technique.

Basically, stretching my consciousness by giving me challenges and questions that aren’t in my current paradigm to help me search for understanding. What I came to realize was, “If you’re not a party to the decision, why would you be deeply invested in the decision?” We then moved into a phase where we became intensely collaborative in the business and it worked out quite well.

I have to imagine that first Monday morning, when you were starting to ask these deeper questions of your staff. They probably didn’t open up just right away. They’re probably like, “What the hell’s going on here?”

Using Intentional Pauses To Foster Creative Solutions

There were times. I said to my mentor, “I’ll ask a question to the group.” There’s silence or they give an answer then they look at me like, “What do you think?” I’m like, “It’s like they want me to dive in and answer for them.” He said, “Yes.” He taught me the trick of just looking at my watch to remind me to not answer, and I wouldn’t answer. It took a while. After a while, they came to realize I’m not just going to come in and give the answer that then they can go execute.

Which keeps all the responsibility and risk on me and no real commitment on them but we’re going to do this together. What emerged were insights about the decisions we were making that none of us had anticipated. Creative solutions that emerge from the intensity of the understanding that was forged that none of us had anticipated but were clearly superior answers than what any of us would have predicted the right answer was going to be. To the point where we knew going into any of these collaborations that there’s a better answer than any of us realize. It’s here to be found and we can do it together. That was ultimately what we developed over a five-year period.

That’s pretty powerful learning for a group to have that realization that they can embrace the uncertainty of a situation and know that they’re going to figure it out. A lot of groups never get to that point.

We never would have if it wasn’t for Jim Patton who was a senior executive at DuPont. He had a heart attack that moved him off the fast track, and he became a certified Covey 7 Habits facilitator at DuPont, among one of the first corporations to ever invest in actual on-staff people to help have more effective meetings. This is back in the ’70s where they started this, but they had a cyclical downturn. They cut all the soft skill people. He was then basically my age at the time. I thought he was ancient. He was 64. He became available as a consultant.

These are highlights of the journey I was on. I’m hitting the good highlights. There were more than a few hard moments where you’re brought face to face with the limits of whatever wisdom you’ve been able to scrabble together at that point. The words experience is the greatest teacher are proven true. When there’s a new product introduction that you believe in and it fails miserably, you have to withdraw it from the market.

When there’s a cyclical downturn like the Y2K collapse and what was 35% year over year sales growth goes to eight. Which was fortunate, but still now you’re looking at laying off 7% of the workforce. Hard stuff. A lot of these difficult lessons from the hard things, including my own mistakes, are in the book, A Work Life Worth Living, because they all ultimately served a deeper understanding of what matters about my work life. It’s not all just the rainbows and unicorns.

It would be helpful to hear you talk more about some of the bad moments that you’ve just referenced, particularly just thinking about how pre-28-year-old Jeff might have handled some of those situations and how post-enlightened Jeff handled those situations.

I wouldn’t say enlightened. I’d say on a path of growth, Jeff, as opposed to unconscious, clueless Jeff. The biggest difference between Jeff graduate, succeeding was only to find out because my mentor asked me that the reason I was working so hard was to prove something to my father. That was an epiphany when I realized, “That’s what I’m doing?” I was like, “That can’t be the basis of a career.” I had to work harder to figure out, “What then is a basis for a career?”

The big difference in what’s in the book is having someone you can talk to who’s not your best friend, a guy you know from the bar, somebody you played rugby with, or your uncle. Everybody has somebody at arm’s length who has a certain level of maturity and wisdom that you just know is there. It’s such a compliment to anyone to ask them, “Could I talk to you about some things that are not going the way I want in my work life?”

You’d be amazed how much clarity you can get when faced with a fork in the road, some surprise of whatever kind to just say, “I’m going to step aside for a second.” Unless the building is on fire, there’s very few decisions that need to be made tomorrow and to talk to somebody who has no dog in the hunt. The most powerful thing I ever realized. It’s not advice, but something to consider if you face that unexpected fork in the road.

Your book emphasizes this importance of reflection. Why do you think so many people avoid it?

That’s a great question. Honestly, first of all, I was never asked to reflect on the quality of my experience when I was in school. From 4 years old to 22, it was just, what’s next? Everything was laid out for me. I had some choice of courses and things, but it’s like, you’re going to take the next step. You’re going through the motions, pause and say, “How was this experience for you?” That begs the question of, “Would you like a different experience?” I can’t give you a different experience because you got to do what you’re supposed to do next. There’s no reflection in all that.

Making Reflection Your Team’s Secret Competitive Advantage

Secondly, when you get to a certain point, you invested a lot of time and energy and where you are and what you’ve done, then somebody says, “Let’s reflect on how this went.” That brings you face to face with the possibility of getting in touch with how much regret you might feel or shame or angst or fear or whatever about how it went or blame or anger. It’s like, “Don’t open that box. Let’s just move on.” That’s what it was like when Jim first introduced the idea of like, “At the end of a meeting, let’s take a few minutes to reflect on the quality of the meeting.” We’re like, “What?”

It became so powerful because we iteratively kept tweaking our process the way we met based upon the feedback people had. It started out like, “I’ll give you a reflection. This sucked.” That’s what it was like at the beginning and he’d say, “I appreciate the honesty that was shared in the room.” We’ll be like, “What are you talking about? Was there something good about this meeting?” Slowly but surely we realized that appreciation fed appreciation and when people felt appreciated, you could then have a better meeting and we were getting better outcomes because it was less of a battle.

It was more of a dance and you realize, “We’re different. I’m in sales and you’re a hardcore research guy but I can talk your language. I can hear you. Can you hear me?” The next thing, it’s like, “He does think that I have some merit even though I’m just a salesman.” Now we can talk about, “I can’t just bring the product specs in and put them in front of a guy and put a price on it and say ‘Buy it or not.’ It’s just not going to work. Do you want to learn more about salesmanship?” This is just so powerful. When you get in a habit of reflection, you can learn from your past experience and apply it to your future experience. When you do it together, it builds on itself and it becomes a positive flywheel.

For a lot of people, they’re intimidated by it for all the reasons that you mentioned a minute ago, like shame, embarrassment, or whatever. It’s a liberating thing to get to the point where you’re willing to accept all of your imperfections and your bad reactions to things and everything else and move on anyway.

I’m not focused on helping leaders because most leaders have some budget for their self-development and there’s coaches. That a custom support system is powerful. I had it and it’s great. That already exists for most people if they want it. What I’m focused on is the people who don’t have that development budget and particularly when it comes to these deeper issues of feelings and purpose. My experience is, even when the leader is a complete zealot for this stuff, a deep believer and everybody knows. It doesn’t mean they trust them because they work for you. Their job security is at stake.

Their pay is at stake and you’ve got a big economic interest in how they contribute. It’s like, “Do you care about what matters to me?” Understandable skepticism in our corporate world. I don’t begrudge folks who didn’t buy into my most gentle invitations to consider what mattered to them. I never asked them to tell me, ever. That would just be way too unsafe.

Point simply being that it’s a delicate road that we tread when we get into deeper personal issues. When we reflect, we open ourselves up to the possibility of realizing that, hey, maybe we made a mistake. Maybe we’re on the wrong path. If you’re on the wrong path and going up the wrong mountain or down the wrong ravine, the sooner it, the better. Emotionally, there’s still a sense of, “Can I afford to acknowledge that I shouldn’t have become a doctor?” We carry a lot.

People are carrying a lot. What I’m trying to do with the book and with the platform, MeaningSphere.com, is create a safe place for people to explore these issues, provide some simple guidance about how to get the support you need to sort through this before you go jump in jobs or worse, jumping off a bridge. People do that too and it’s terrible in the law and in medicine. The amount of mental health issues is in some ways wrapped up in our lack of self-awareness about the work we do.

Yet for most people, there’s very little in the way of resources to help with that aspect of their mental and emotional well-being. I’m attempting to provide people easy access to affordable and carefully curated resources to help because I’m like the luckiest guy in the world. This is my life’s work to see if I can’t pay it forward because I was given so freely these great gifts. None of this is my idea. There is nothing I’m doing that was my idea. My idea was MeaningSphere, to create a platform where people can do this together. But that’s not even a new idea.

Philosophically, certainly what you’re talking about is well aligned with why I started PathWise, the business that I run, because I too have benefited tremendously from the professional development that I’ve gotten over the years. I wanted to be able to give back and democratize some of that for people in a way that was accessible and affordable. It’s rewarding and challenging all at the same time.

I’m curious to get your experience because one of the challenges is that getting people to come to this content and these kinds of resources, a lot of people are happier complaining than they are doing something about what’s bringing them down. That’s a sad statement, but it’s a truism that I’ve discovered the hard way.

For most people, the systems that they exist within, educational and employment, all they’ve got agency to do is complain when they’re not there. Because it’s too risky to complain when you’re there. Where are they? Ever seen an example where something could change or that they could change their situation? I don’t blame people for complaining. At least they’re vending and they’re getting some of it off their chest.

I never thought about any of this stuff. I discovered I had no idea about right. If it wasn’t for both some shocking disappointments and some unplanned and unsought experiences, I wouldn’t know what I know now. No judgment about people who might be stuck or might be feeling like they’re a victim of their career. It’s understandable. What’s evident is, if you’re waiting for the world to change before you can feel better, you’ve got to be waiting a long time.

Come back to your own company and your experience and the journey that you went on with your employee base. The point you made earlier about the fact that a lot of people are hesitant to speak their minds, to reveal their true selves, to do all the things that you’ve mentioned that come with this territory. Their economic livelihood depends on keeping that job and making sure that boss or that CEO or whoever thinks well enough of them to keep them within that organization.

Even if you’re not managing by fear, people carry that fear because you are in a position of power. How did you change the dynamic? What were some of the signals that you got from employees that they were having their own epiphanies, their own wake-up moments about how different life could be?

In addition to forcing myself to not answer my own question, and when you trust people, you are committed to inviting people to share their true perspective, strap on. It is shocking to find out how much people are telling you what they think you want to hear. When they tell you what they think, you’re like, “Are you working in the same company I am? It is amazing.” Yet it is indicative of how little support people get to be able to build a frame of reference around why they’re there.

Connecting Individual Roles To The Broader Human Purpose

Typically, they’re hired for skills to do a job. That some boss tells them, “The goal is this. You’re responsible for that.” We’re in this business. That’s the connection they get to make. What do you think about how your contribution helps move the company forward? What’s that chain of connection between the work you do and the cup of coffee that we serve the customer at Starbucks? How does the tax process affect that experience? Who has that conversation?

Not too many people. When I started having that conversation, I realized that as people were joining the company. I’m like, “How do we do this?” Once we started realizing that transaction tax software is implicit in the entire economy and it doesn’t work without it. It’s way important to use the highly technical term “way.” We realize that talking to people doesn’t work. I would meet with people in groups of 8 or 10 after they’ve been with the company from 2 to 3 weeks to 2 or 3 months in groups and ask them, why do you think the company exists? You’d be amazed.

Not just young people coming in, but people in their mid-30s and 40s to increase shareholder value to meet the customer’s needs. Basically, they give me answers they think I want and be like, “Where’d you buy those boots?” They’d answer and I’d be like, “Why’d you buy them?’ They’ll be like, “I like the way they look or I need them to ride a horse,” or whatever it is. I’d be like, “Did you buy them to help the company increase shareholder value?” We’d start having a conversation about the chicken and the egg in terms of, does the company exist for the shareholder or does it exist for the customer?

If it exists for the customer, then what are we doing? They’d be like, “What are we doing?” I’m like, “Why’d you take the job?” They’d be like, “It had the best benefits. It was a convenient location. It was the best job I could get.” If I would listen, which I would try to do, people would open up. Usually, of the group of 8 or 10, there’d be like 2 or 3 who were like, “This is cool,” and they would get into it. That would make it safe for others. There’s always two who just sat there terrified, like, “I hope this ends quickly.”

That’s what I did for twenty years. As we grew from 70 people when I became president to about 1,000 when I was no longer CEO. I went on the board and was chairman for five years. The point is, it took constant dialogue. We held all employee sessions for full days, where we had professional artists help draw in murals what the employees were saying about why they felt that the work mattered and where the connections were, to try to give them an opportunity.

What I said to everybody was this, “I feel like I’m accountable to all stakeholders to lead the company toward the purpose that we share for it. It’s not my purpose. It’s our purpose. Based on your input and perspective, this is what it feels like, what it might seem like. Is that why we’re here? What do you think?” We spend the day talking about it and then feedback. We did continue engagement for new people

About every five years, we do an engagement program. Engagement meant listening to them, not talking to them. The proudest statistic that I have of my tenure was 4.5%. We had 4.5% total turnover every year for twenty years in technology. We didn’t overpay. We paid P60, but that was strategic. It wasn’t like we were just bribing people.

Did you see, as you were doing those sessions with 8 to 10 new employees at a time, I have to imagine you saw an evolution in how those conversations went. How did you look back and say, “This is different from where we were a year ago or two years ago?” What were those moments like for you? What were they like for your employees?

You would think that’s what I would have seen. Exactly the opposite. That’s why I had the a-ha that what’s needed is MeaningSphere. This is what I need to do with the rest of my life. For twenty years, they came in exactly the same. It didn’t change at all. I’ve been doing this for 10 or 15 years before Simon Sinek publishes Start with Why. That was another. Covey was big. No change. It wasn’t like the movement that we’re aware of that you and I are part of.

It was reaching people and they were coming in and saying, “I’m here because I understand this company stands for something more than just the bottom line.” The bottom line is here to help serve an even higher bottom line, which is, are we enabling an economy that meets the needs of the society or does this culture give me the space to be there for my coworker when they’ve had some life event? Can we be human here together? Those are the things that you’d hope that over 5 or 10 years, you’d build a reputation that people would be able to say those things, at most. You’d hear, “I heard it had a good culture.” That’s about it.

I’m sitting there thinking, with what I know, the amount of research I would do into what a company’s culture is like before switching jobs would be just way more than the product.” You think about what you’re signing up for when you change jobs or in any job. With that environment, it shapes you. It will turn you into a different person. We make those choices in such a cavalier way. It’s because we’re not aware of just what conditioning influences the workplace.

I had spouses come to me in tears on multiple occasions. I don’t know what you’re doing, but he’s a different person and I’m so grateful. I’m like, “It’s not me. It’s not what I’m doing. We’re doing this together.” People would go home and they’d be a little more interested in listening to their spouse. We did communications that were intended to be. Be more user friendly for the significant other about our benefits program and we started to be more conscious of relationships. I feel so very fortunate.

It’s fascinating to me that the cultural things you were doing didn’t manifest themselves in your recruitment process. People came in as uneducated in year twenty as they did in year one.

When you have people who care about the work and want to succeed and have technical knowledge, corporate tax software is a very intensely technical world. This is hard to balance. Your first thought is, “This individual better have the technical ability and skill to meet the demands of the job.” The culture is nice and everything. I love the culture too, but I’m not going to hire somebody because they love the culture.

They got to know how to program. In the hiring process, I had to walk my own talk and not do too much. Frankly, the only times I took over, we never went well. The people who had the skills were way better, even though I had “the power.” I never intervened on this, but I felt like we could have done a much more proactive job of recruiting people with skills who also wanted the culture that we were offering. I don’t know that we were ever very successful with that, honestly.

Fair enough.

Since we had such great retention, even though we were growing, we weren’t hiring as much as other companies because we were losing people.

Now, we’re in this era of AI, which is automating more and more of what we do by the day. How do you think that affects what meaningful work looks like in this new era?

The foundational primary research done in the field over twenty years, peer-reviewed, journal-published, primary research conducted by Dr. Marjolein Lips-Wiersma at the Auckland University of Technology with her partner, Sarah Wright, demonstrated that people care about mostly relationship-related issues with other people.

There’s four quadrants that the research clearly identifies, unity with others, integrity with self, service to others are 75%. This is cross-cultural. The only one that is more skill related is mastery. Mastery is very meaningful. As you develop mastery, the people’s things will become more important. With AI, it will help accelerate mastery if you’re careful and you don’t take it at its word and you do the underlying research but it will have an accelerating effect.

Will it help individuals feel like they’re working with others and in an environment where they can have integrity with themselves? That is all about relationships and the expectations that are present in the environment and your effectiveness in clarifying and negotiating those expectations. Will you feel a sense of unity with others? Do you feel unity with the machine? Maybe. Maybe some people are feeling, at least so far, some level of unity with the machine.

The jury’s out in my mind with regard to how healthy that is. We’ve got some decades of research to find out how healthy that trend might be. Count me as a skeptic. When a robot can shake my hand and I feel a pulse, I feel body warmth, I know it’s a person and I can feel the intensity of that handshake. That is different. I don’t even want to shake a hand with the robot.

Protecting Human Judgment In An Automated World

These human dimensions that build trust, that build a sense that I matter. I matter in a context of how others see me. I feel what makes being human so wonderful and also difficult and challenging. Will AI speed up all the intellectual things in dramatic ways? Absolutely. When you think an AI can decide for you what you care about, that’s where we’ve lost our way. We’re going to recognize that as a society, as a humanity and go, “This power is here to serve us and help us serve why we’re here.”

We’re not here to become subjugated to the power of this intellectual behemoth because life is richer than that. I point out in each of the action step sections of each chapter, a little bit of a hint about, is this a place where AI can be helpful? Two thirds of them, AI can be helpful but I also point out where you’ve got to own the responsibility of taking what AI is telling you and divining for yourself what matters to you. It’s the question confronting us.

It’s a key question. For some people, they will relish the ability to spend more time on deep work, deep conversation and deep interaction. Other people are going to find it terrifying and exhausting. We’re going to have to go through what that change process looks like for a lot of people, potentially. We’re obviously observing that more of the transactional aspects of work can be accomplished in an automated fashion. That’s going to leave the harder stuff and we’re going to have to rise to the challenge. The companies that do the best economically will rise to that challenge, but I hope they don’t lose their souls anymore. Most companies have already lost their souls so far.

We’re going to find out. It’s not going away. I’m an optimist, ultimately. No pain, no gain. Whether that’s working out, learning a new skill or a trade, building a company, there are going to be disappointments. There’s going to be surprises. There’s going to be difficulties, adversity. Those are all learning opportunities. AI is yet the biggest one. We’re inherently adaptable and we care. We care at a heart and soul level. Not at a, “I’m going to say words of caring because the book I just read in an instant tells me that the right word to sound caring is so-and-so,” which is basically what an LLM does.

You’ve got this book. You’ve got MeaningSphere. For somebody who reads your book, A Work Life Worth Living, what do you want their own Monday morning experience to be like after they’ve read the book?

That’s a great question. In a perfect world, the people who read my book would go to work on Monday morning in wonder, just in wonder, “What else might I discover about myself and the world of work and this environment that might not have dawned on me before having read that book? Open your heart up to insight that you might not have had before. Why is the environment the way that it is? What are the unspoken? When you start perceiving those, you start feeling them in yourself. A whole world of new possibilities to take ownership of creating the work life of your dreams becomes possible. That’s what happened to me. I hope that’s what happens for you.

I would just add on to that. Step into the breach despite whatever misgivings or fears you may have. Because it is a bit of a courageous leap to start to look at the world in a different way, the way that you’re describing. People have got to get themselves across that chasm and be willing to move on in spite of everything that comes with it, messy or otherwise.

These old words of wisdom, “No pain, no gain,” things like that. There’s a reason we say them because they’ve been borne out as true and nothing ventured, nothing gained is one of them. It sounds trite, but if you don’t swing the bat, you cannot hit the ball.

It’s very true. Thank you. A philosophical conversation. I appreciate your time and what you’re doing now with your own movement and I wish you the best of luck with it.

You, too. It’s a pleasure. Thank you so much for having me.

Take care, Jeff.

To wrap up the conversation here with Jeff, I want to leave you with a few ideas that I hope stay with you. First is that success and fulfillment aren’t the same thing. We know this intuitively, but we often forget it day to day. The promotions, titles and financial rewards are important but they’re milestones. They’re not necessarily destinations. A truly rewarding career comes from aligning your work with your values, your strengths, and the impact that you want to have on others.

Second is that meaning is something that you create. It’s not something that you find. Waiting for the perfect job or the perfect organization is probably going to be a recipe for disappointment. The people who experience the most fulfilling careers are intentional about how they show up, the relationships they build, and the purpose they bring to the work they’re already doing.

Third, and you heard this in spades from Jeff, leadership is ultimately about helping other people thrive. The best leaders create environments where people can grow, contribute and find meaning in what they do. Link it to a broader purpose. That’s good not only for employees, but for organizations as well. Vertex is certainly a beneficiary of everything that Jeff did to make that real in his company. Finally, as AI changes work, our humanity is only going to become even more valuable.

Technology will reshape jobs. It will take away certain tasks that we perform. The uniquely human things like curiosity, empathy, judgment and purpose and the ability to inspire others are going to become increasingly important. Building a work life worth living isn’t just about keeping pace with change. It’s also about becoming the person that technology is not going to replace.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with somebody who’s looking to become a better leader or build a stronger career. You can also sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks for tuning in.

Important Links

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• Jeff Westphal on LinkedIn
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• Jeff Westphal on Instagram
• MeaningSphere
• Vertex
• A Work Life Worth Living
• 7 Habits of Highly Effective People
• DuPont
• Start with Why
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About Jeff Westphal

In the mid-1990s, Jeff Westphal took over his father’s upstart sales tax software business and over the next two decades built it into a dominant industry leader. Under Jeff’s leadership, Vertex became an essential cog in the commerce machine, relied upon by more than ten thousand of the largest companies in the world. Behind this success story is another, more complex story of how a leader found, then lost and found again, meaning in his life and work, and how, by helping his employees create meaning in work as seemingly meaningless as sales tax software, he helped his company thrive. Today, Jeff is a seasoned corporate executive, entrepreneur, philanthropist, corporate culture enthusiast, and conservationist. In addition to leading Vertex for two decades, he has founded two new ventures, MeaningSphere® and Mosaic™, as he continues to give back and encourage others to create meaning in their learning and working lives.

Most professionals assume great work speaks for itself, but solid Product Positioning proves that value never communicates automatically. When competitors offer flashy feature checklists or when crowded markets blur real differentiation, buyers and hiring managers get confused quickly. Host J.R. Lowry sits down with April Dunford, leading positioning expert and bestselling author of Obviously Awesome and Sales Pitch, to unpack why building something valuable is only half the battle. They walk through actionable frameworks to move past surface features, clarify unique value themes, and align internal teams before ever pitching external buyers. Together, they break down how individuals can treat their career journeys like high-stakes B2B products by narrowing focus, embracing natural strengths, and knowing exactly when to walk away from poor-fit opportunities. Finally, they tackle the rise of artificial intelligence, outlining why automated tools raise the bar for genuine business strategy rather than replacing it.

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/april-dunford/.

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Why You? How To Stand Out In A Crowded Market, With April Dunford

One of the biggest frustrations that exists in business is watching what we would perceive as an objectively good product struggle against a competitor that’s inferior. We’ve all seen it happen in a company we’ve worked for, or a product we’ve bought, or even in our own work. We assume, perhaps naively, that if something is genuinely better, people are going to recognize it, but that’s often not how markets or even careers work. My guest, April Dunford, argues that success is much more than about building something valuable. It’s also about helping people understand why it’s valuable and why it’s different.

That’s the discipline of positioning. Few people have really shaped this field more than April. She’s helped hundreds of technology companies sharpen their positioning, accelerate their growth, and tell a story that customers actually understand. She’s the author of Obviously Awesome: How to Nail Product Positioning so Customers Get It, Buy It, Love It and Sales Pitch: How to Craft a Story to Stand Out and Win, two books that have become essential reading for founders, marketers, and sales leaders around the world.

In this conversation, we’re also going to go beyond products and companies and talk a little bit about what positioning can teach us about our own careers, why talented people are sometimes overlooked despite doing great work, and how AI is changing the way organizations and people need to differentiate themselves. Whether you’re leading a business or building a product or simply trying to stand out in an increasingly crowded world, I think you’re going to find plenty here to think about. Here’s my conversation with April.

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April, thanks for joining me.

It’s great to be here.

I’m glad to have you on the show as well. Let’s start in an area that I know you have focused a lot on, and that is product positioning. A lot of people think of that as a marketing exercise. Positioning is one of the classic four Ps of marketing, after all, but you would argue that it is much more fundamental than that. Tell us why so many of us have it wrong.

Here’s the thing. Positioning impacts marketing a lot, but it doesn’t impact just marketing. It impacts products. It certainly impacts sales. What I have found in my experience is that if we treat positioning like a little exercise that belongs in the marketing department and only the marketing department works on it, then what I’ve found is that whatever positioning we come up with, sales doesn’t like it, product doesn’t like it, the CEO founder doesn’t like it, and then there’s always a big fight. Because a shift in positioning really impacts all these other groups, it would make sense to me that we would need a cross-functional team to work on it.

Part of the reason why we want a cross-functional team to work on it is that sales knows a lot about what’s happening with customers, particularly early stages of deals where our positioning matters a lot. Product management knows something else. The founder knows something else. It’s actually good to pull in the information that the other parts of the organization know to actually develop your positioning. Let’s say, for example, we were going to shift the positioning. I work at a company, and it’s a business intelligence tool.

We were going to shift the positioning and say, “No, we’re not a business intelligence tool. We’re a data warehouse.” Imagine me in the marketing department trying to make that decision. I just show up and say to the CEO, “By the way, we’re not a business intelligence tool anymore. We’re a data warehouse.” Do you not think the CEO is going to have an opinion about that? Do you not think the sales team is going to have an opinion about that or the product or anybody else? They would. We cannot treat this as just a little marketing thing.

Although even though it may be marketing’s job to be the steward of positioning once we have it locked down, it may be marketing that if we feel that the positioning is getting weak or off track or something, it may be marketing that puts their hand up and says, “I think we got to pause game here for a second and fix this.” The actual work of doing the positioning and then even the work of making it real out of the market is not just a marketing thing.

You’ve worked with a ton of companies over the years on go-to-market topics. What are they getting wrong when it comes to talking about why their product is different?

There’s a bunch of things. I work specifically with technology companies and, even more specifically, all the companies I work with are B2B. The product is complicated enough that there is a salesperson involved somewhere in the sales process. There might be some product-led growth or zero-touch part of the sales process, but there’s a sales team that gets involved somewhere to actually close the deal. If you look at those kinds of companies, there’s a handful of things that are really common.

Escaping The Speeds And Feeds Trap

One is we’ve got a fairly technical product that we’re selling to sometimes a fairly technical audience or fairly sophisticated audience that understands the product a little bit and what it can do. There’s a tendency for those companies to sell on what my old boss would call speeds and feeds, which is features. You come in and say, “We have this feature, that feature, this feature, that feature.” We’re just going to tell you what all the features are, and you, as the buyer, are going to look at that set of features, understand what the features are, understand why those features are important or not important to your business, and make a purchase decision based on that.

Good positioning doesn’t operate at that level. Good positioning is really trying to answer the question, why should you pick our solution over anybody else’s? To answer that question succinctly, we really need to get at what value these features can deliver for your business. How is this product going to help you make money? How is this product going to help you save money? How is this product going to reduce risk in the business? The features are just how we get that done.

In order to sell this stuff well, we really have to get up to that value level. A lot of tech companies do not do a good job of getting it all the way up to that value level. Occasionally you will see companies that do, but then the problem is, they’ve just got too many points of value. They’ve got like eight points of value or ten points of value. They’ll say, “Look, here’s what we’re going to do, we’re going to save you time, we’re going to save you money, we’re going to do this, we’re going to do that. Everything with the kitchen sink.”

The customer is left to figure out, “Hang on, there’s a competitor, and they do some of that.” There’s another competitor that does this. There are ten things. I’m not sure I can remember all ten. They’re not getting tight enough on the bigger, higher picture of why pick us versus the other guys. Getting that down to 1, 2, maybe 3 value themes that a customer can really understand, “Your approach looks like this, and the value is this,” versus a competitor’s approach, which looks like this and the value is something different.

What’s fascinating to me is this idea of selling the value or selling the solution. It’s not a new idea. It certainly predates this modern rise of the technology company. Yet so many companies still want to go out and sell features.

What you get sometimes is, and I get it. The sales team will come and say to me, “Value, that’s good, April.” You do not understand. These customers are educated. They come, and they have a checklist of features. We have to show them that we meet this checklist of features. That’s a reasonable thing to say, but then I ask the question, where did the checklist of features come from? They did their research, and somehow, in this research, they decided these are the features that they need to have.

Now, if you look at what makes your product different and special, it’s the features and capabilities that the other guys do not have. Is your key secret sauce on the checklist? Probably not, because they haven’t talked to you yet. If it’s there, great, then you can tell them something. If it isn’t, it’s your job to educate them on what the checklist of features should be and in order to do that, what I’m going to have to do is I’m going to have to tell you a story. I’m going to have to paint a picture where I say, “Look, traditionally every other solution in the market looks like this.”

When we founded our company, we looked at that, and we decided that wasn’t good enough. We took a different approach to the problem. That different approach means we have a different set of features. Why should you care? This different set of features can deliver this value that the other guys cannot, and so I’m going to have to take you on that journey if I’ve got a hope and a heck of a chance of landing this deal.

If I’m the leader in the market, no problem. Their checklist of features probably looks like mine, because I’m the biggest one in the market, where maybe we can get away with that to a certain extent. Until I got a hotshot little AI native startup thing nipping at my heels that comes in and does exactly what I told you right there. They come in, and they say, “Feature Schumacher.” That’s the old way of doing it. Let me talk to you about the new way of doing it.

Different values, therefore different sets of features. Throw that checklist out. If we’re doing a good job of selling this stuff, we get to be able to talk about the differentiated stuff that we do. We cannot just assume that a customer is going to understand that because our differentiated stuff, by definition, is only something we can do.

Certainly, you’ve got the influence of a procurement function, sometimes even a third-party consultant who’s running the process, who comes with RFPs with thousands of questions on them, literally thousands of questions you have to answer, which is the equivalent of the feature checklist. It’s easy to get distracted by all of that. I would argue a consultant community has created a cottage industry for themselves just in running RFPs.

It’s hard when you’ve got that level of, “If we do not have an answer to this question, we’re going to get knocked out of the process. You get so focused on the details. You get so stuck in the weeds that it’s really hard to come up to the bigger picture level and sell the value or the overall solution or the overall differentiation. I cannot understand it.

Especially if you’re not the incumbent. If you’re not the biggie in the industry, chances are if we’re going to RFP, the biggie in the industry, this is the first call they made. They probably built the RFP based on the conversation they had with the biggie in the industry. If you’re not the biggie in the industry, then you have to decide how we are going to change this conversation. Do we have an opportunity to change this conversation? If we do not, maybe we’re not going to respond to them. A lot of the rps that cross our desk because the fix is in, man, the RFP has been built with somebody else, and we’re just never going to run that thing.

Same deal with consultants, right? I’ve worked in businesses where the consultants are really influential and really drove a lot of the purchase behavior. That being the case, we had to go figure out how we were going to get a bunch of these consultants on our side before we went and started wasting our time trying to sell directly to customers because the customer is just going to ask a consultant, and no consultants know anything about us, and no consultants are sold on us. Now we got another constituency we got to focus our sales energy on.

That was certainly true in the world that I’ve been in over the last twenty years.

It’s not uncommon.

If you’re a leader in one of these companies, how can you tell whether you have a positioning problem or a product problem?

Back when I was in-house, I spent 25 years as a vice president of marketing. I was very worried about joining a company where the product was the problem because it’s really hard to change a product if you come in and you’re vice president of marketing and the product is no good. You do not want that job. If I were doing the interview, what I’d be looking for is there traction? Are you selling stuff? Is the churn fairly low? Are the customers fairly happy? Does the growth look okay? If you’ve got a thing in market and it’s selling and there’s growth and the churn’s not too bad, I would run on the assumption that the product’s good enough.

Good enough to do some deals. If we’re doing that and the marketing looks average or not very good, I can come in as the vice president of marketing, and I’ve got something to work with here. We can make it grow because the thing looks good enough. I would always run on that assumption. Now, the harder one is when the company comes to you and says, “Look, it’s not growing as fast as we’d like it to.” We got happy customers. The churn is low. We got some growth, but the growth isn’t as high as we’d like it to be. There could be lots of different problems.

That could be a positioning problem. That could be a lead generation problem. It could be an awareness problem. Nobody knows you exist in the market. I’d be looking at things like what happens when a lead gets to sales and sales does their magic and sales closes every deal, and it’s all good. That’s unlikely to be a positioning problem. You just need more leads coming into sales. That’s a lead generation problem. Now, if the lead comes to sales and maybe a lot of them drop off there, that might be a positioning problem.

Diagnosing Weak Positioning On The Front Lines

It might not. What I would do is, if I took the job when I’m brand new vice president of marketing, I would go down and listen to what happens on a first sales call. The inside sales reps have got a deal hooked, and the customer decides, “Yes, I’ll give you an hour with an AE, and we’re going to go have a conversation.” I’d listen to what happens in that conversation, and weak positioning sounds very specific in that conversation. Often what you’ll get is a customer comes in, and the rep is there, and they’re doing a pitch, and the customer is just confused.

You can see it right from the beginning of the pitch, where the customer is making this confused face. They’re like squinting their eyes. You can see there often is this thing, and I used to see it a lot in sales calls where the positioning was weak, where the salesperson would be telling this story and it sounds pretty good, but they get to like slide 3 or 4 and the customer’s like, “Wait. Just go back and start it again. I missed something. Nothing you’re saying is making any sense.” There’s some missing piece to the puzzle where the customer cannot quite figure out what bucket to put you in.

You’d hear a lot of that where the rep thinks it’s pretty obvious, but they’re going to go back to the end. That’s one. You’d hear this other one where, and this would come up a lot, where the customer would go, “We get it.” You’re exactly like, pick your poison, Salesforce. You’re not, and then the rep is like, “No. Let me go back to the beginning.” You’re getting compared to something that you shouldn’t be getting compared to. That’s generally a positioning problem. The third one, which is actually the worst one, is when the rep gets to the end of the pitch.

The customer is, “I get it. I get who you compete with. I get what I would replace in order to bring your stuff on. I get the value of this thing.” I do not get why anyone would pay for that. Can I just do this in Excel? Can I just have a couple of interns do this thing? They get it, what you’re trying to do. They just do not think it’s all that valuable. The value is not really hitting them in the gut. If I heard things like that, then I would generally take the head of sales out for lunch and say, “Look, this is what I’m hearing in these calls. Is that common? Is it typical? Am I just cherry-picking bad calls?”

If the vice president of sales says, “We actually hear that a lot in first calls.” Even then, I wouldn’t know for sure that the positioning is bad, but I got a pretty good inkling at that point. I’d be like, “Look, dude, we call this positioning. This is how it works. When was the last time we looked at the positioning?” The answer’s like, “Positioning, what’s that?” I do not even know what that is. I’d say, maybe we need to get the gang together, marketing, sales, product, and get the CEO in here. Maybe we spend a couple of days on it and see if we cannot tighten it up.

You get everybody in the room, and you work on it. What everybody wants is a metric. If this metric from this stage of the deal to that stage of the deal looks bad, it’s probably a positioning thing. The problem is weak positioning gets you out the whole way through the purchase funnel. It’s hard to nail that down, but you can hear it in these early customer conversations, customer confusion, putting you in the wrong market category, not understanding the value. This is what I’m usually listening for.

Certainly, it makes it important, if you’re a leader, to participate in some of those sales calls, because what’s hard to tell.

A lot of times, we have gone now. They’re all recorded. You can pull them up. You can listen to it. You do not necessarily have to show up live for the call. This is getting easier and easier to do.

It is getting easier, and you do not even have to get in the car and go to the meeting. You could just listen to the recording afterwards or get the AI summarization of how the meeting went.

You’ve got to be a little careful with the AI summary. The AI summary will sometimes summarize exactly the clues that you’re looking for, so you’ve got to be really careful about that. A lot of the companies that I’ve worked with that are looking for these clues in the call recordings are actually looking at the raw transcript because it’s these little comments where the customer comes in and says, “Wait a second, is that just like Salesforce?” Or “Wait a second, why wouldn’t I just hire an intern to do that?” That might get edited right out of the call notes if you have something summarizing that. You’ve got to be careful.

Fair enough. Those things are probably picked up by most AI tools as being inconsequential to the real outcomes of the meeting. Yet there was information in those moments. Let’s shift gears and talk a little bit about the idea of positioning beyond products and take it to the idea of how you position yourself in the job market, in the job you’re in, the company that you’re working for. A lot of people go through life feeling overlooked. They work hard, they feel like they’re delivering good results, but they do not seem to get the recognition or the opportunities that they deserve. How could they apply positioning principles to help themselves?

I’m going to caveat this by saying I do know nothing about this. To be honest, I wrote a book on positioning called Obviously Awesome. It’s very specifically the methodology I’m describing in there for a B2B tech company to figure out how to do their positioning. When I first took this book to publishers, I had a publisher suggest, “Why don’t you make this like positioning your life or positioning yourself? You’d like to get a job or a date or something.” I was like, “I do not want to be a self-help guru, buddy.”

Treating Your Career Like A B2B Product

No, not interested in that. I can tell you a bit about my own personal experience and how I think this works. Early in my career, I was trying to figure out how to position myself for work, and I think it helps to look at this the same way you would a product, which would be like if they did not hire me, who else would they hire? Who’s my competition? If you look at all the other people that are out there applying to the same job as you, or maybe interviewing for the same job as you, you have to be able to answer the question why should the hiring manager pick you versus anyone else, like what do you have that’s different and special?

A lot of times, I think people aren’t thinking about this when they’re applying to the job or even when they’re coming in to interview for the job. They’re trying to convince a hiring manager that they can do the job. Everybody who’s getting interviewed could probably do the job. How are you going to do the job better? Sometimes it’s not even better. How are you going to do that differently than someone else? Why should the hiring manager care about that? Sometimes it has nothing to do with doing the job.

Sometimes it’s like, “I work really well independently. I take feedback really well. Here’s how I’m going to prove that.” It could be the proof that you could do the job. I’ve actually done a job very similar to this 5, or 6 times. Early in my career, I had an engineering background, and I landed in marketing. At the beginning, that wasn’t all that weird. As time moved on, it got to be more and more of an advantage for me that I knew how to program. I knew what a SQL query was, so I could go in and say, “Look, I’m going to work better with the product management team than people that do not have that because we speak the same language. We come from the same background.”

The developers are not going to be annoyed to work with me and be credible and say, “I’m going to work with the technical side of the business better because I have that. If we were selling to a technical buyer, I could make a case that because I had this technical background.” This was in the early days of people moving from brand marketing to doing some measurement on stuff. I would say, “Look, I know my way around a spreadsheet. The numbers do not scare me.”

That was a thing. As my career went on, I learned different things, and there were different things that I was good at. I had worked at two or three database companies, so I knew a lot about databases. I could come in and make the case for that for some companies. I had done positioning work 2 or 3 times, which is actually a lot of times if you’re an in-house person. You do not do positioning every day. It’s not a thing that every job requires. I could come in and talk intelligently about positioning and how we might fix that positioning in a way that other people couldn’t.

What I found when I was a hiring manager is that the people coming in and interviewing with me often did not really understand what made them special. They’d come in and say, like, all my jobs are B2C, but I really want to do B2B. It’s like, I do not care. I do not care what you want. You’re up against a whole bunch of people that have all this B2B stuff already. You’ve got to answer the question for me, why should I hire you? The answer cannot be because you want to work here. Everybody wants to work here.

I get a lot of that, like people would come in, very almost self-centered that would come in and say, “This is what I want.” I’d be like, “That’s nice, but let me tell you what I want.” By the way, I’m the boss. Here’s what I want. What I want matters more in this specific situation. People need to think about what makes them stand out, what makes them special. Maybe they want to focus their energy on getting in front of people and applying to the types of jobs where they’re a better fit than other people who might be applying. I had this once.

At one point I had done lots of B2B stuff, and there was a period where B2B wasn’t cool anymore in tech. Everybody was doing apps, and B2C was cool, and B2B was no good. I thought, “Man, maybe I should make the switch to B2C.” I applied for some jobs, and everybody gave me an interview. I do not know why, but I’d show up to the interview, and I’d be tap dancing. Maybe like, “How does this experience apply if you’re going to be over here as a consumer?” I did not have very good answers for that. Needless to say, I did not get the job.

In the end, I just did not make the jump. I was like, “Look, B2B isn’t hot right now, but that’s my jam. I compete pretty well over on the B2B side. The pool is smaller, but I think I’m going to have to stay over there.” I did. It was smart for me to do that because two years later B2B was all hot again, and there I was right in the middle of it. I see a lot of people coming in, and they’re not really thinking about the person who’s doing the hiring, and they’re not really thinking about answering that question why me versus the other five people you’re interviewing.

There are a couple of things I want to pick up on in what you just said, April. One is this idea that they’re not putting themselves in the shoes of the hiring manager. I think tied to that is the idea that people forget that when they’re interviewing for a job, they’re selling themselves. That concept feels really foreign and probably even uncomfortable to a lot of people. It really does come down to that. There are multiple people interviewing for this job. Why should I hire you instead of all of the other people? It’s a product differentiation thing. What makes you better than the others? If you’re not thinking that way, you’re missing the essence of the conversation.

A lot of people, I think, just really struggle with that. The other thing is just this idea of repositioning yourself. You were a B2B person, thought about trying to get into a B2C world. That’s a repositioning in essence. Those are always hard conversations because you’ve got to convince that hiring manager, in the case of a job, that what you’ve learned in this other space is actually relevant in the space that they’re in. What are some of the lessons that you can think of from how companies reposition themselves in different markets that would be applicable to how somebody could do that more effectively if they’re trying to reinvent themselves from a career perspective?

Selling Internal Stakeholders First

I can give you some examples. One is, I found that when you’re going to reposition a company, and you see we used to be a database, but now we’re a business intelligence tool. The first thing you had to do was make sure everybody inside the company believed the new position before you took it outside. Everybody inside the company had to get their heads around this shift. I had to sell everyone inside the company before we could attempt to sell anybody outside the company. The analogy to that is, let’s go back to my case. I do not think I fully believed I was a B2C person. Yet it did not stop me from applying to the B2B jobs and going out and having these interviews.

The reason I wasn’t getting the job was that I wasn’t making a very good case for me to be a B2C person. If you want to make this shift, you’re going to have to believe it. The only way you’re going to be able to get your arms around it and believe it is if you’ve got facts to back you up. If you can convince yourself and look in the mirror and say, “I’d actually be great at this. This is why I’m great at this. This is how it applies. This is how I’m going to pitch it.” You’ve got to believe it first before you can go sell anybody else. This is true inside companies. It’s way harder to convince the people inside than it is to convince the people outside.

The other thing is that it cannot just be like, I’ve worked at companies where I’ve gone in, and they said, “Look, we made all our money selling into the mid-market, but we do not like selling to the mid-market anymore. What we want to do is sell to the big companies. Let’s just reposition billion-dollar companies because we’re sick of selling to these little guys.” We’d like to sell fewer deals, but at higher prices and whatever. This is what I call aspirational positioning, which is like we wish we could position up there, but often when we have that, we look at the product, and we’re like, “Does it actually work up there?”

It’s not just the product. It’s the pricing. It’s the go-to-market motion. Do we have services? Can we support these customers? The big guys want 24/7 multilingual support. They want a professional services team. They want somebody to come on site. We’re not going to be able to sell them off the website anymore. We might have to hire a sales team to go and do that. Everything changes. That’s not just a little shift in positioning. Again, if I use my case, I had this little aspirational idea. Maybe I should go to B2C because B2C is hot. The reality was, it was the wrong product. I was trying to sell this B2B thing. Everybody liked me.

Narrowing Scope To Multiply Leverage

I was good at interviews. They’d bring me back for a second, third interview, but they’d all be scratching their heads. They’d be like, “We do not really get it.” We do not know how anything you’ve done applies. I’d be like, “Trust me, I’ll figure it out.” When I gave up on it and I went back, I ended up taking a job at a B2B company, and just the whole tone and everything else of these interviews, I was like, “What was I thinking? I’m a B2B person. I need to stay over here where I’m good.” I knew that thing. This has also been a guiding thing in my consulting business too. B2C companies come to me all the time, and they’re like, “Can you help us with the positioning, April?”

I just say no. These are companies that are literally like, “Take my money. Here it is. We believe in you, April.” I say, “No, I do not know anything about B2C.” They’re like, “We’ll be the first. It’ll be fine. Just take our money. We’ll do it.” The reason I say no is because I do not know if I can do it, and so I do not know if it’s going to be worth it. It is better for me to just say no and stick to the companies where I know we’re going to smash it. That’s my little box outside of my little box. I do not know. Maybe it’s going to work out. Maybe not.

That’s the essence of positioning yourself.

That’s it. You say yes to what you say no to because it just ain’t a fit over there.

We would be remiss if we did not talk at least a little bit about how AI is affecting the types of things that you’re doing. Do you think that AI is changing the way that positioning is occurring or needs to occur in the B2B tech world? Does it simply make execution of that positioning faster?

It’s interesting. There’s a whole bunch of levels to it. The first and most obvious level is that competition is coming from all sorts of corners that we did not expect it to come from in a lot of market areas. There have been companies that have been coasting along. Things have been good. They have competition, but it’s competition that looks just like them. Now all of a sudden they got an AI native company in there that’s taking a completely different approach to the problem. Because they’re taking a completely different approach to the problem, they can deliver value in a different way. In some market spaces, that has really thrown the cards up in the air.

Companies are having to react to that in terms of a shift in their positioning to account for this new type of competitor that can do these things in a different way and that. That’s one thing. Almost everybody in every market is wrestling with this right now. It’s the reason why I’m busy right now. The competitive landscape looks totally different than it did 2 or 3 years ago. The second thing is that not only does the competitive landscape look different, but it’s also harder to get your arms around it. It’s harder to know what’s real competition versus potential competition, but not quite competition yet. Who knows, maybe never competition, but we do not know quite yet.

A lot of companies are in a space where people talk about vibe coding and vibe coding a product. A lot of companies are in a space where theoretically a little dedicated team could maybe vibe code a thing that looks like this. A customer could do it, potentially. I’m working with a handful of companies where, if you ask them, “Who’s the competition, who should you be positioning against?” Folks on the product team will say vibe coding. We’re in big trouble with this vibe coding thing. Now, sometimes that’s true, and sometimes it isn’t, so sometimes customers come, and they’re saying, we’re looking at vibe coding things, but what you got. Maybe we’ll buy you, maybe not.

Maybe we’ll go inside. In which case, they are competing directly with a build-it-your-own vibe coding tool solution. They’re going to have to account for that in their positioning. What is the stuff they’ve got that the vibe coders just ain’t going to get right? Sometimes that isn’t the case. Zero customers are actually doing that right now. Now you’ve got to decide. If you believe that is coming down the track, if you believe we haven’t seen it yet, but it’s coming next year or the year after, then you’ve got a product roadmap problem.

What am I going to put in my product roadmap so that when that happens, we’re ready? At the same time, I do not have to position myself against the ghost. I only have to position against things that my prospects consider competitive. If my prospect’s not looking at vibe coding and I show up and say, “Let me tell you why we’re better than vibe coding, that is dumb.” What you’ve done is you’ve now taught your prospect that they should be looking at a thing that they haven’t looked at. You do not want to be doing that.

You have to be careful that your positioning is meeting your customers where they’re at right now. Now, that doesn’t mean you ignore what you believe to be true or what you think is going to happen in the future. You cannot ignore that. This is a product roadmap problem. Are we getting ready behind the scenes? It doesn’t necessarily show up on your external stuff. It doesn’t necessarily factor into your positioning yet. It’s very hard for customers to determine the line on that. These same companies are probably talking to their investors about the vibe coding thing and the AI stuff they’re doing.

They’re probably going crazy when they’re talking to investors about that. We need to tell that story with customers, yes or no. Right now it has never been so important because there’s so much upheaval and uncertainty in the market. It has never been more important. To really have your finger on the pulse of where your buyers are at, what they’re looking at, what they’re taking seriously, and what they aren’t taking seriously.

Honestly, the difference between what you’re reading on Hacker News and LinkedIn and Reddit or wherever you hang out, where the techie people hang out, what you’re selling to manufacturers, like the difference between those two things has never been starker. You got to be careful not to get so hyped up and so caught up in, like, “Everything’s happening. It’s all happening next week.” If your customers are not there yet, now in some cases, maybe your customers are, but you really got to know where your customers are, and you really got to have this positioning that meets the customer where they’re at, and that right now is really hard.

Customers are all over the map in terms of their level of understanding. I would think, though, that this makes differentiation a lot harder because there are a lot of things that you could vibe code or recreate using some AI tool that may have been secret sauce in the past that now feel like, “I could do that myself.”

Yes and no. I’ve heard this argument that people come and say, “Features do not matter anymore because anybody can add a feature because it could just vibe code it.” It’s like, that’s not how code works. I have an existing product with existing customers. It might speed up my delivery of a feature for me and my competition. We had competition before. We could code things, and they could code things. Now we could both code things faster. What’s the difference? There is no difference. We’re all just moving faster. We have differentiation in the market now. Now everybody has AI.

Confronting Artificial Intelligence Without The Hype

This is not a competitive differentiator. If you could vibe code it, they could vibe code it. They can vibe code a thing that’s different from yours and better than yours. You can vibe code a thing that’s different than theirs and better than theirs. It’s just a matter of speed. We’re all moving, and now we’re all moving faster. I’ve never worked with a company that’s in the market and successful that doesn’t have any differentiation. You have it. A lot of times, that differentiation is that the company has made a deliberate choice to approach the problem in a different way.

It’s not about a feature. The complete architecture of the thing is different. Everybody’s doing it like this, but we came in, and we’re doing it this way. There are very few markets I could point to where the number one, number two, and number three are taking the exact same approach to the problem. It’s just not how markets work. There’s an incumbent in a space, and you come in, and you’re getting any traction at all?

You’ve got serious differentiation. Otherwise, you wouldn’t sell anything. When people have this theoretical thought that anybody can build a feature, anybody, whatever, I’m like, “Tell me the two companies you’re thinking about in your brain.” Like, “Are you thinking that we’re going to vibe code Salesforce?” Now, if I was a little weak company and you said, “Can we vibe code a little CRM?” “You can.” Is it going to look anything like Salesforce?

No, it’s not going to look anything like Salesforce. Salesforce would probably be overkill for that company anyway. Can we vibe code little things? We can. Can we vibe code big things? We can vibe code big things too, but I do not think if someone’s going to come in and challenge Salesforce, it’s going to be somebody that’s taken a completely different approach to solving the problem of CRM.

That’s who’s going to beat Salesforce. Not somebody that comes in and says, I got a copycat Salesforce. It’s just like them. Except none of our people have any experience, and we do not have a professional services team, and we do not have any of the partnerships. We do not have any of the integrations. We do not have any support either, but otherwise the features are exactly the same. That’s not how this is going to play out.

Using that example, part of their competitive moat is all of those things. It’s not just the code base.

That’s right. It’s not just the features. It’s everything else. We have the whole issue, too, of there being existing code bases and existing customers and how people switch from one thing to another thing. A lot of these traditional SaaS businesses are now trying to figure out how to compete with themselves. They’re taking a big lean back and saying, “Should we just rewrite this whole thing to make it AI native? How fast could we do that? If we did, what would that look like? What do we do with the existing customer base? How do we move them over?”

All these things, these are big questions. It goes beyond positioning. What is going to win? It’s building a thing in a way that it’s different. It’s building a thing that can deliver something that’s unique. The other guys cannot have this new set of tools that operate in a different way. That should give me the ability to approach the problem in a completely different way. If you see the AI companies that are doing a really great job out there, the ones that are growing really fast, they’ve come into a market, and they’re like, with this new set of tools and this new set of capabilities, we can start from the ground up and build something completely different. They’re winning because they’re telling that story.

There’s got to be a certain element of reinvention of how the product works and is conceived. To recreate Salesforce, to recreate any incumbent SaaS product, would be the wrong way to think about it.

Whatever beats Salesforce is not going to be a thing that’s set out to copy Salesforce. It’s going to be a thing that said, what if we had the opportunity to start from scratch and build everything new, knowing what we know now? When Salesforce was built, our concept of what we wanted to do with CRM was completely different. Knowing what we know, you would approach it completely differently. You would redefine what CRM even means at this stage.

I’m sure people at companies, traditional SaaS businesses, most of the ones that I talk to, are having this conversation internally with themselves. They’re like, “What if we started from scratch and built this? What would it look like? What would we do differently?” Knowing what we know now, because when we built the original thing, it was. However, many years back. We thought about these things differently. I think these are the more interesting things that are happening with AI and any big shift in technology.

These architectural shifts have been going on for decades, and the people who succeed in these new errors are the ones, to your point, who rethink the business model, the delivery model, the value model, not just, “We’re going to take our on-prem software and dump it into Microsoft’s public cloud or Amazon Web Services and say, ‘Now we’re a cloud product. Everybody sees through that.’” The same will be true here. Having an AI chatbot that sits on top of your crummy software product that needs to be rethought is probably not selling an AI-powered product. It’s a lot different.

I’m telling you, two years ago, that was everybody’s gut reaction to it. We’re going to take a chatbot. I got a chatbot on it now. We’re AI. I think two years down the road, now we think very differently about that. Now it’s like, that ain’t it. Now we’re talking about agents. What can we do with agents? It’s very different. I do not think we’ve seen, and I do not think we’ve seen the end of that evolution yet. We’ll know a lot more about how this all shakes out and winners and losers and what this really looks like in the next year, two years, three years. A lot of what people are predicting is going to happen just ain’t going to happen. Some of it is, but a lot of it isn’t. We just do not know the difference between the two right now.

We’re definitely in that in-between era right now. With all this said, what would you want to leave our audience with in terms of the lesson that you would want them to take away on positioning their companies, their products, or themselves?

Replacing Gut Instinct With Repeatable Process

Here’s the big thing, and this has been my life’s work. The big thing with positioning is that positioning is very hard to do well if you are trying to do it from gut instinct. Now, not impossible, but if we can do positioning using a process, a structured process, like step one, step two, step three, step four, it just makes your whole life easier. If you are really good at this stuff, and maybe you think, I can feel this, Having a process so that everybody understands how you got to where you got to, and it wasn’t just your genius thought in the middle of the night.

It’s going to help everybody understand what the positioning is. The other thing is that when you do this gut-feel positioning, sometimes it works. When it works, it’s amazing, but it generally doesn’t work forever. At some point you’re going to have to shift that positioning. You got a new competitor, something changed, you changed, you did an acquisition, something changed. It’s very hard to shift that positioning because you did not use a process to get to the positioning in the first place.

If you really want to tame positioning and you really want to feel comfortable with your positioning, the number one thing you can do is use some process to say, “This is how we got to where we got to.” Doing that is going to help you in the long run. It’s going to help you when you need to shift. It’s going to help you even figure out, do I need to shift this right now or not? It’s going to have to get the whole team on board. That’s the last thing I would leave you with is that having a structured process to do this stuff is going to save you in lots of situations.

Thank you. It’s been a fun conversation. We won’t be able to vibe code our way through all of that for sure. I appreciate your time, April.

Thanks so much for having me on.

—

What should we take away from the discussion just now with April? The first thing is that being better isn’t enough if people cannot see why you’re better. Whether you’re launching a product or growing a business or trying to advance your career, value doesn’t speak for itself. You have to help people understand what makes you different, why that difference matters, and who benefits most from it. Positioning isn’t spin, and it’s certainly not the purview of marketing alone. It’s something that everybody in a company needs to be clear on, and it’s something that you need to continue to work on by putting yourself in your client’s shoes.

The same is true if you are looking for a job or trying to convey your value in the job that you’re in second, and we did not talk a lot about this, but it’s an important thing that April mentioned at the end. She’s not out there trying to support everybody. She wasn’t the right fit for B2C jobs. Many times you can actually grow better by narrowing your focus as opposed to broadening it. When you go too broad, it’s harder for customers to understand who you really are, and the same is true for you individually.

You have to make it clear where your depth is and what types of circumstances you would be good in a company. That means being clear where your product fits and where it doesn’t, and when you do that, things often just come together much more naturally because you are focused on your strongest points, not trying to be everything to everybody. Third is that in an AI-enabled world, differentiation is going to become even more important. AI is making it easier to create content, build products, and automate routine work.

Those capabilities, therefore, are becoming less distinctive. The competitive advantage shifts to understanding customers, making sound strategic choices, communicating a compelling story, building trust, and ultimately solving problems. Technology can help you execute all those things faster, whether it’s AI or anything else, but it cannot decide what truly makes you worth choosing.

Those same lessons, again, can be applied to individuals. As always, I invite you to subscribe to the show on Apple Podcasts or Spotify or YouTube or whatever your favorite platform is, and if you found this discussion enlightening, you can sign up for my membership community, which is called Pathwise, or our newsletter, Path Wisdom. Thanks. See you next time.

Important Links

• April Dunford on LinkedIn
• April Dunford on YouTube
• April Dunford on Instagram
• April Dunford on X
• Obviously Awesome: How to Nail Product Positioning so Customers Get It, Buy It, Love It
• Sales Pitch: How to Craft a Story to Stand Out and Win
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About April Dunford

April Dunford is a globally recognized expert on positioning and one of the leading voices on helping companies stand out in crowded markets. Over a 25-year career as a marketing executive, entrepreneur, and consultant, she has helped hundreds of technology companies sharpen their positioning, accelerate growth, and communicate their value more effectively. April is the bestselling author of Obviously Awesome, a practical guide to product positioning, and Sales Pitch, which focuses on turning positioning into a compelling sales story. Today, she advises primarily B2B technology companies, helping leaders understand their competitive alternatives, identify differentiated value, and give customers a clear reason to choose them.

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In this episode of Career Sessions, J.R. Lowry sits down with Dave, one of the world’s most influential thinkers on leadership, talent, and organizational effectiveness, for a wide-ranging conversation about what great leadership looks like in a rapidly changing world.

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And, inevitably, they tackle AI. Dave argues that AI makes distinctly human capabilities more important, not less. As information becomes ubiquitous, leaders will increasingly differentiate themselves through vision, innovation, emotion, judgment, and wisdom.

The conversation also explores learning agility, navigating uncertainty, admitting when you don’t know the answer, and becoming comfortable figuring things out alongside the people you lead.

Whether you’re a first-time manager or an experienced executive, this episode is a reminder that leadership ultimately isn’t about you. It’s about what becomes possible for other people because you were there.

Looking to build the leadership lessons from this episode into your organization? PathWise offers leadership coaching for companies.

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/dave-ulrich/.

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Watch the episode here

Listen to the podcast here

The Real Job Of A Leader, With Dave Ulrich

Whether you’re a first-time manager trying to lead a team, a seasoned executive navigating constant change, or simply someone wondering how to stay relevant in an AI-driven world, leadership has arguably never been more challenging or more important. My guest has spent more than four decades helping answer a simple but fundamental question, what makes leaders, organizations, and careers successful?

Dave Ulrich is widely regarded as the father of modern human resources, but that title doesn’t begin to capture the impact of his work. He’s advised many CEOs, worked with organizations around the globe, authored more than 30 books, and helped shape how businesses think about leadership and talent, organizational capability, and value creation. His ideas have influenced not just HR leaders, but executives across virtually every industry.

In our conversation, we’re going to explore how leadership is evolving in the era of AI, why experience is no longer enough to sustain a successful career, what separates people who continue to grow from those who plateau, and what Dave’s learned from a lifetime spent in the boardrooms and the C-suites of some of the world’s most successful companies. Whether you’re leading a team or simply trying to build a career that remains valuable tomorrow. You’ll come away with some practical insights and perhaps a different way of thinking about what it means to create value. I’m J.R. Lowry. This is Career Sessions, and my conversation with Dave starts now.

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Dave, welcome. Thanks for joining me on the show. It’s a real pleasure to have you with me.

What a privilege. I’m honored to be with you and our guest.

Honored to have you as a guest, so let’s get rolling. You have had a very distinguished career working with a number of companies and CEOs. If you think about leadership relative to when you first started back in the ‘80s or ‘90s. What do you think has fundamentally changed and what is different from the way it used to be?

Sometimes, we have experiences that shape the way we think. I listened to Peter Drucker once, and Peter Drucker said, “The greatest leadership ever was the pyramids.” I thought, “We haven’t changed anything since whenever that was in Egyptian history.” My sense as I take away that experience, a lot of the leadership principles are timeless. His comment was, “Look what they did in the pyramids with no technology, and no operational machinery. They built these incredible monuments to their legacy.”

A lot of the fundamental principles are the same but the practices and timely stuff do change. We’re not the same as we were 20 or 30 or 40 years ago. A few years ago, we were all obsessed about COVID and how do you manage remote workers? Now, we’re obsessed about AI. A few years ago, AI was just a dream, and we’ll talk about that. Some of those timeless principles are so important. The one I’ll just highlight because I want to make it a setting for our discussion.

Helping Others Build Their Story

One of the things I find among the best leaders is every leader has a good story to tell. JR, you have a great story. I’ve looked at your background. Your life and your story is great. Leaders don’t tell their story. They help those they lead create their own story. Leadership is not about what I know and do. It’s how what I know and do helps and you know and do what you need to do better. This episode is not about, “Dave, let’s tell your story. Here’s your research. Here’s your ideas.” Your job as a leader is to help others build their story. I hope that’s the theme. We’re here to help those reading create their story based on our experience.

We’re certainly going to get into some topics aimed to help people think about how to think about their careers and how to think about leadership. You mentioned AI. I’m going to go right there because it’s so prevalent. It’s dominating conversations at the board level, C-suite, all the way down to the front line. What do you think that means? Given what you just said about leadership and what changes and what doesn’t change. How is AI affecting leadership? What becomes more important in this new AI era? What may become less important?

We could spend the next 45 minutes on it. Let me just highlight a couple of things and I’ll try to highlight just two or three. One of the things, AI is not the goal. It’s a means. It’s access to information that we never had before. I was doing a talk at a university and I said, “I’m interested in how Plato compares with Thomas More’s Utopian society.” Boom. I had a polished report in less than 30 seconds. I thought, “When I was a graduate student, I would have been paid a semester to go create that.”

We have ubiquitous access to information. In fact, it’s interesting. AI gives you polished reports, information data that we’ve never seen before. As a leader, I can get information quickly. What’s missing is the human ingenuity to turn that information into productive knowledge. I’ll put that in a formula. HI or human ingenuity times AI or artificial intelligence. How do I navigate the balance between those? AI gives me capacity. Human ingenuity gives me capability. I’ve got to manage both.

If I avoid the AI, I’m not going to have the information I need. If all I’ve got is the algorithm and the AI and not the human ingenuity, I’m not going to differentiate myself. Quick tips, use AI. Don’t become dependent on it. There’s some amazing research coming out about cognitive decline, cognitive replacement, and cognitive surrender. Be careful to not get seduced into AI as a solution. It’s a set of ideas, a set of knowledge. It will give you a polished report. It will not give you guidance on how you have the confidence to make that report happen.

To me, and certainly one of the things that I hear coming up in conversation is that human judgment, critical thinking, and the ability to collaborate are some of the things that AI is going to have a harder time replacing. Those are the things that become more important. To your point, if you abdicate responsibility for doing your critical thinking to an AI tool and have it doing all of it for you, your critical thinking skills are bound to diminish over time. That’s what the research is starting to show.

The VIEW Framework For Human Ingenuity

By the way, my background is taxonomy. I love to take complex things and simplify. Let me give you a way to think about what you just said. What is human ingenuity? I’ve got AI, which is an algorithm, which gives me information, data and ubiquitous access to knowledge. What does human ingenuity mean that I uniquely bring? I’m going to suggest four things. That’s my taxonomy. Vision of the future. If somebody says to you, “What do you bring that complements the AI work going on?” AI can’t create the future. It only summarizes the past. Vision of the future. Innovation in the present.

What’s that beautiful human element where you get at the back of your head, your hair goes up, you get a nudge, like, “That’s cool.” Peter Drucker said the Egyptians were the most powerful leader, vision, innovation, emotion in relationships. You just said it, AI is not emotion. It’s an algorithm. It’s fake emotion. The one that you highlighted, and I’m going to call it wisdom, critical thinking, judgment, wisdom in decision-making. Vision, innovation, emotion, and wisdom view.

Human ingenuity gives me a view. I’m saying, “We’re doing a lot with AI.” Don’t get seduced. What’s the vision of the future? Look forward, not backward. What’s the innovation? What’s new here that its system didn’t give? Emotion, empathy, relationships, and then judgment, critical thinking. I hope those things are helpful. I know I miss a lot. I’m not naive about that. To me, that’s the compliment to the AI agenda that the algorithms give.

My final tip, I’ve gotten into discussions on social media with an algorithm. Don’t get into a debate with an algorithm. It’s not going to be a very good debate because they will keep flowing and flowing. I want to build a relationship. I want to look at somebody. I want to feel somebody with that emotion. Debating an algorithm is not going to be a very successful outcome.

Leadership Value: AI gives you capacity, but human ingenuity gives you capability. Strengthen your vision, innovation, emotion, and wisdom to stand out.

One of the things that relates somewhat to AI, but more generally that I’m thinking a lot about, and I want to get your perspective on. A lot of managers that I talk to are saying that their jobs are becoming harder. Expectations are rising. They’re being asked to manage more people. The pace of change is getting faster. Now, we have AI taking away some of the things that their individual contributor team members used to do, and frankly, that they used to do. What’s left for them, I’m hearing a lot of them say, feels genuinely harder. Are you hearing that in your own travels as well? I would love to get your thoughts on it.

I have two responses. The first is no question. What AI does, it doesn’t replace jobs, it replaces tasks. If you look at any process, let’s say staffing process, hiring someone. There’s ten steps in hiring someone, defining the skills, getting the resume, etc. AI can do four of those ten tasks efficiently. Sometimes leaders like doing those tasks because they are easy and they let us do something. I can’t do the more complicated tasks that require vision, innovation, empathy, and emotion. We’re stuck with those.

At one level, it is tough to be a leader now. At another level, if I went back and talked to some older leaders, they’d say, “It wasn’t all that easy in the ‘60s when we had revolts. It wasn’t that easy in the ‘70s when we had major crises.” Leadership has never been the easiest job in the world. Again, this will be the last time I mention Peter Drucker’s Pyramid. Go back to building the pyramids. I don’t imagine it was easy. They were built through horrible command and control logic, slavery, etc. It probably wasn’t very easy back then either.

Leadership has never been easy. What I’m finding around expectations that I like is people are getting more conscious and intentional about their expectations. Do I want to be a leader? Leader comes with a price. We talk about mid-career. It’s like, “My career is stalled out. Am I comfortable doing what I’m doing now or do I want to pay the price of ambition to move into other leadership positions?” It’s hard to be a leader working twenty hours a week remotely from Montana or from an island South of Boston. It’s hard to lead.

Paying The Price Of Ambition

A lot of people say, “I want the flexibility that comes in the world.” You have every right to that flexibility, but recognize it comes with a consequence. I faced that early in my career. I went off to be a professor at the University of Michigan. We had 2.2 kids. That tells you where we are in that status. My wife started a PhD program. We looked at each other and said, “We are choosing not to outsource our kids. We are going to raise our kids and muddle through parenting.” I can’t believe I’m getting emotional because it was a tough decision. For the next five years, I cut back.

That wasn’t the greatest time of my career to cut back and stay home while my wife did her PhD. I stayed home two days a week. I took the kids to school. I did stuff. I paid an ambition price so that I could do some other things that I chose to do. I’m not advocating that anyone should make those choices, but that was our choice. I ended up not getting tenure. That was a conscious choice. Sometimes, as careers, we say, “I want to have it all. I’m going to be the greatest. I’m going to be the greatest everything in the world.”

I hope leaders are clear about their expectations with intentionality. By the way, I wouldn’t change anything we did because it allowed us to balance. When my wife finished her PhD, we looked at it and said, “Here’s what a psychologist makes. Here’s what a consultant makes. I’m going to go do a little more consulting.” She said, “Go,” but we then still negotiated. Our deal was I would never be gone on weekends. You know what travel is. I’ve looked at your career map. Travel is tough, especially from the United States if you’re in the Gulf States. I love the Gulf States.

You can’t travel and not be gone on weekends if you’re going to do work in the Gulf States. I didn’t do any work in the Gulf States for fifteen years because that was the deal. Takeaway, we’re helping you create your story. Be conscious. What do I want? Recognize it’s a long career. When our kids left home, my wife looked at me and said, “You could be gone more.” That may not be the best solution and answer, but the decisions we made then were good for them and good for us.

They aren’t good for anybody else, but those decision records may change. I spent 15 or 20 years on the road a lot, and that was a choice. I’d ask leaders the question, “What do you want? How do you define your success?” Recognize that’s not a one-time answer. That may change at 25 when you’re single, at 30 when you’re newlywed, at 35 with kids, at 40 or 45. At my age, it changes again. What do you want? Be intentional about that. Be clear about what determines my definition of success and value? You pay a price. Long answer to a very fair question about expectations.

There’s a lot to take away from what you just said. Probably most important is this point at the end about the fact that what works for you then is what matters. It’s going to change at different stages in your life. Your story highlights that perfectly. As long as you’re intentional and thoughtful about it, it’s hard to look back with regret because you’ve made conscious choices.

May I tell a quick story? This one, I love to tell. I’ve told it before, but it’s a powerful story. This was a CEO. I would not recommend this for almost anybody, but he’s a very successful and very senior CEO in New York. I’ve been coaching him. I go in and he’s down. I say, “What’s going on?” He said, “Work is fine and we’re dealing with all the issues, but my fifteen-year-old son and I aren’t getting along very well.” I said, “That’s never happened before. Tell me about your son.”

He’s like, “My son’s terrific.” I said, “What does he love?” He said, “He loves baseball.” I asked, “Who does he love?” He said, “The New York Yankees.” I looked at the CEO and I said, “They’re in the World Series and it’s going on. Go to a game.” He gave me one of the dumbest answers of a smart executive I’ve ever known, “I don’t have a ticket.” I said, “Your son is You are a total doofus. What do you mean you don’t have a ticket? Get online. Get great seats. Get your son out of school. Get a car. Go eat hot dogs. Get sick. Go to the game.” He said, “Can I do that?” I said, “Are you kidding me?”

He called two days later and said, “You reminded me of what mattered most. My son and I had a great night. We’ll remember that for decades.” I hope at your level, wherever you are in your organization, don’t be afraid to do those kinds of things because they have such meaning and such impact. When I was traveling so much, my mother was retired. We had three kids. I was doing work then around the world. I called mom and I said, “Mom, do you want to see Hong Kong?” She said, “Yes.” I said, “Good. Let’s go.”

My mother has traveled with me to some of the greatest spots in the world with my three kids. She watches them during the day, then we have dinner. There’s a lot of ways you can begin to manage the life balance that I hope those who are reading make conscious choices. Now, where did this start? Don’t assume that you can have everything and still be promoted and move up. There’s a price that you pay but the price that you might pay is a good one. There are other people who make another choice. I want to move in my career. I enjoy the status. I enjoy the power. I enjoy the influence through hierarchy. If that’s your choice, we have the right to make that choice.

You’ve talked about defining success and also defining value. You mentioned value in passing, but I know this is a very central concept to the way that you think, this idea of what value are you creating. Talk a little bit more about your thoughts on that, because it’s going to set up this idea of how people can stay relevant over a long and uncertain career journey.

Connecting Values To True Value

Great question. There’s two words, values and value. Values are, what is my identity? What am I known for? When COVID hit, it changed my career. I was traveling. Guess what? You’re not traveling. What’s my core value? What are my values? I want to learn. I’m going to have to discover a new way to learn because I’m not going to learn by flying around. I’m going to learn through webinars, through doing things like this, with podcasts, through social media. I’ve never done social media.

My first question to somebody is, what are my core values? What matters to me? That’s the question we started. What do I want? How do I want to be known? What’s my identity? What’s the story I want? That’s 50%. The other 50% is, how do my values create value for someone else? If my values don’t create value for someone else, it’s not long-term viability. It’s narcissistic. It’s hedonism. Leaders are not hedonists. The leader affirms their success by the ways others behave when the leaders aren’t in the room because their values have created value for someone else.

I love to talk about what you value and how your values create value for somebody else. As a leader, first question. Who am I serving? Is there somebody I can serve and create value for? I got that headset. That’s what senior leaders do in a company. Who are you creating value for? How will my values help them build their story? I’m going to go back to that story metaphor. I’m not here just to create my story and impose it. I’m here to create my story so that you can create yours even better.

Particularly in the frame of a leader, this idea of giving up the self for the other is an important mindset shift that not all leaders remember every day. They start to believe their own hype. They forget that there are many people around them who’ve made them successful over the years. There’s a lot of people who depend on them. That constant, who am I here to serve and how can I create value for them? If you can ask that question of yourself, it will help keep you grounded. That’s something that I take away from what you just said.

The So That Query For Calendars

I love it. By the way, I love simple exercises. That’s the taxonomy PhD. Look at your calendar and say, “Who am I going to meet with? What am I going to do? What’s going to happen in their lives because of what I do?” Teach a class. I won’t go through the class in detail, but I was looking at utopian society and how do you build organizations that are utopian? What do I want those students to leave with? It’s the same question. I want to set a vision for that. I want to manage change so that. Who’s going to benefit because of what I do as a leader?

Leadership Value: Having values is only half the battle. The real question is how your values create tangible value for someone else

I want to engage my people so that those employees feel ownership for the work we do. I want to set a vision so that our customers are more likely to buy our product. I want to be disciplined about making change happen so that an investor gives us a premium in price earnings ratio. The so that for me turns my calendar into outcomes for somebody else. It’s a very simple little query that I have found helpful for me. The so that takes me out of my values into the value that I create for another.

I love it. It’s a very simple framework that’s easy for our audience to take away. Thinking longer term, there’s this idea that you hear a lot about. How do I future-proof my career? I would love to get your thoughts on the fallacies of trying to future-proof your career and what you can do.

Staying Sharp With Learning Agility

Two thoughts. One is in the research that Bob Eichinger and the Center for Creative Leadership have done, they look at skills that leaders have that seem to be predicting long-term success. Learning agility comes out high. When is 50% of what I know out of date? I’ve been a professor. I was a professor in Michigan for 43 years. When I teach that course every year, what percent of my teaching notes are new?

There are some professors you can tell the time of day by their jokes because it’s no longer a course. It’s a Broadway play because the joke is scripted. I never went there. My rule of thumb in my world, and everybody’s got to determine their world, about every 18 to 24 months, I should have 25% to 30% new stuff. Am I learning agile? Am I continually reinventing and experimenting? That, to me, is part of what you do. I’m going to give two tips for reinventing your career. Learning agility, keeping fresh, and try new stuff.

By the way, I share this with students sometimes. One of the worst things about, in order for me to be learning agile, I’m going to teach 125% of what I know. You’re not perfect the first time out. The first batch of cookies is never very good. I’m always going to experiment. I’m going to weave into my sessions new stuff. Leaders, try new things. Go experiment. They go, “That didn’t work. I’m not going to do that one again.” There’s a great insight.

The second tip, learn to navigate paradox and tension. Everybody says, “I’m going to manage the paradox. I’m going to be like this.” We live in a world of inherent paradox. Am I long-term or short-term? Yes. Am I top-down or bottom-up? Yes. Am I focused on individuals or teams? Yes. Am I focused on profit, performance financially or caring for the people? Yes. One of the things I love to see in leaders is they say, “This is an inherent paradox. Do you want to be the servant or the master?” Yes.

I love leaders who can say, “I’m navigating paradox and I’m going to lean a little bit this way, then I’m going to lean a little bit that way. I’m going to constantly navigate.” I don’t know if you’ve ever sailed or flown a plane, but you’re always navigating. You’re moving back and forth. Learning agility and paradox navigation become two of those process skills that you can begin to apply as you go forward.

Have you felt like over the course of your career that there have been things that you’ve had to let go of that were central to your way of thinking as the world continued to adapt?

Many. Let go of, did I have an answer? Let go of, tell me the answer. What do you think? I love that question. I don’t have to have an answer. What do you think? Let’s talk. That I have to be prepared. One of the things I’ve learned as I’ve gotten more senior in teaching is a lot of teachers say, “You’ve got a three-hour workshop with executives on pick a topic, like talent or strategy. What are you going to do in 90 minutes? What are you going to do in 120 minutes?”

Lately, I’ve gone into those classes and said, “We’re going to talk about talent. We got 15-20 people here. What’s the biggest talent challenge you face? We make a list on the board. Vote. Good.” We’ve now spent 10-15 minutes. We have three new challenges that are on top of your list. Let’s take the one with the most votes. By the way, I tell people that when I do workshops they freak out. What are you going to do 90 minutes in? I don’t even know the topic 90 minutes in.

I have enough confidence that we’re going to co-discover what’s real. I’ve had to learn to have confidence in the process of learning with the people I lead and the people I work with and sometimes you have no clue. I was in one. They said, “How do we manage the mobility of our employees in China who change jobs so often?” That got a top vote. I can tell you a secret. I have no clue. I said, “I have no clue. What do you think?”

We spent twenty or 30 minutes thinking through the principles of mobility and how they may apply in that Chinese context. People said, “That was helpful. You didn’t just share your latest statistics or research.” That’s the piece that has been helpful for me. It’s just trusting the process to get there. It doesn’t always work perfectly. I’m not stupid about that but I love that dialogue. Question and answer is literally a question.

Listening to what you just said, it feels like it touches on a lot of the things we’ve talked about in terms of how more of the world is going to work because we’re all going to have more of these conversations that are about bringing our collective wisdom to bear. It sits on top of all the factual knowledge that we can now get at our fingertips.

I posted a thing with Charles. It used to be that you learn it at the training program, you know, and then you go do. Flip it upside down. AI tells you what to do. Now you got to figure out what you need to know to make it happen. I love your comment about collective wisdom. If nobody knows, let’s talk. Let’s discover. Let’s co-create. To me, that’s exciting because that’s how we also stay fresh, is learning together and we’ll make mistakes.

There’s a great line, “I’m not failing. I’m learning.” It comes from Carol Dweck’s work in Mindset, “Failure is an opportunity to learn.” In fact, I say to leaders, “Tell me about a failure recently. What did you learn? How did you make that better?” Those were the lessons where people at any career stage, early, middle, or late, to stay fresh.

I think the idea of learning agility in particular, just adaptability. Take your example of how we do mobility for employees in China who are switching jobs all the time. These are new problems. Nobody has necessarily figured out the answer to them. The same is true of what the world is going to look like in ten or twenty years because of AI. Nobody has a clue. There’s some perspectives that are better informed than others.

What that means for you as an individual is you need to accept the fact that there’s a lot of uncertainty about how the world will unfold. You need to make sure that you’re giving yourself optionality. You give yourself optionality by being adaptable. You can’t go much further than there. Your workshop analogy probably fits here, too. You’re 90 minutes in, same things. You can’t predict what you’re going to be doing ten years from now.

One of my favorite workshops is when we bring in senior HR leaders, small groups, fifteen, and we say, “What’s on your mind?” Some of those are some of the most creative discussions that I just find delightful because we’re allowed to co-create and get ideas out that will be interesting. I find that fascinating. Let me just pick up on your comment. We live in a world of uncertainty and we love to solve the uncertainty. Let’s do scenario planning.

Anchoring In Certainty Amid Chaos

What I love to do in a world of uncertainty is start with certainty. Don’t chase the uncertainty. Stop. What are you certain about? Let me go back to where we were. In the world of COVID, when’s travel going to open up? Is it going to come back? I have no clue. What am I certain about? What are my values? I am committed to learning. That’s useful. In a world of uncertainty, we don’t know what’s going to happen with interest rates, inflation, tariffs, regulation, elections, and toxicity. We hope we can get over toxicity.

My first question is, what are you certain about? How can you then live your certainty? How can your certainty help others live their lives better? That’s the value in values. I hear people, “The world is uncertain. It’s ambiguous. It’s volatile, uncertain, and complex.” The VUCA world that we’ve talked about and they get all obsessed. Let that go. How can you live that value and make that value a value to somebody else? In that world, I don’t know what your career will look like but if you’re living your life with certainty. I shared that it was spending time with young kids. For a while, it’s been something else. Those things become helpful in navigating certainty in a world of uncertainty.

Leadership Value: Reinvent your career before it stalls. Experiment with new ideas and refresh your knowledge base every eighteen months.

A lot of people reading probably still feel some level of discomfort because we take mortgages that have 30-year paybacks. We’ve got commitments to family and other things that are important to us. Yet the ability to safely say, “Am I going to have a stable income stream for the next 3 years, 5 years, 10 years, or however many years?” It’s hard sometimes. That level of uncertainty is still challenging for people because they’re forced to make some decisions that hopefully won’t go against them.

They may go against them. I didn’t get tenure. That’s not a good thing. Sometimes putting those things in context. The other side is people said, “How did you handle PhDs, muddle and careers?” We simply muddled. We didn’t have a perfect vision. We didn’t have everything laid out. We muddled. Muddling means you try it. It didn’t work. You experiment. It didn’t work. You learn quickly, fail fast. Our kids now have kids. We have grandkids. Our kids are going, “Dad, life is complex. It’s tough. Are you muddling enough?”

Live with the muddle and it’s okay. Again, I empathize. Will I have a career? Can I pay for a mortgage? No question. Those are demands that are so demanding, but muddle. I don’t know where the word muddle comes from, but it captures the feeling of what it’s like to be in the middle of all of these demands and just muddle.

Brené Brown uses a similar concept when she talks about braving. Being willing to be vulnerable and find your way through all of this in spite of the uncertainties and the doubts that you might have.

I like that word, too. Be brave, muddle, try it, and then fail fast. That didn’t work. Good. Here’s a great insight. Guess what? Stop doing that. That’s not always easy. By the way, it’s much easier to look back and say that than it is to be in the middle of it, which I appreciate.

You forget all the pain from the moment. Last question. What gives you the most optimism about the next generation of leaders?

Spending time with them, just listening to them and seeing in their eyes the bright lights, the curiosity, the ambition. I don’t know about you. I’m so glad I’m not 25 again. When I’m around them, the most optimism I ever get is spending time with the next generation. I walk away knowing they’re going to struggle. You’re going to have struggles. You’re going to have difficulties.

I can give you a preamble to that. I can prepare you for some of that, but I can’t take it away. The struggle is part of the healthy thing. What gives me optimism is my granddaughters from two different parents, email me two or three times a week and text me and just say, “Grandpa, what do I do with this?” That just gives me optimism. Our hope is in the next generation. If we can help that next generation discover their story, that won’t be mine at all, that gives me great optimism.

You especially get to do that with grandchildren, and that’s part of the joy of being a grandparent.

I’m not going to end it yet. What gives you optimism? We never get to learn from you. What gives you optimism?

In the scheme of things, it’s easy to get down about all of the things that are going on in the world, and yet the human spirit seems to persevere. If you think about the world we live in, in 2026 and what it was like 100 or 200 or 300 years ago, it was a lot harder back then. It was a lot more uncertain back then. It was a different uncertainty. You were worried about whether your two-year-old child was going to die of the flu.

You were worried about whether you were going to have war with the tribe or the clan or whatever that was five miles away in another village. We don’t have that to the same degree now. We have different issues that affect us, but we find a way to keep carrying on. It’s not always easy, and there are certainly harder times than other times, but we will find our way through this.

Each generation proves we all have doubts. We all look at the teenagers, when we get older, and we say, “They don’t know anything. I can’t believe this generation is the way they are.” That was certainly said by our parents of us and their parents of them, but every generation finds their way eventually. They are the future, so they will be the future leaders too.

Thank you. That’s very helpful.

Thank you as well.

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As we wrap up our conversation with Dave Ulrich, there are a few ideas that I hope you’ll take with you. One is that leadership isn’t becoming less human because of AI. It’s becoming more human. The leaders who succeed in this new era are going to be the ones who understand what gives them uniquely human skills. That human insight and wisdom that Dave talked about in the conversation and how to marry that with artificial intelligence and all of the other tools that we have at our disposal to do good work in service of others, to create value for others. That is the essence of Dave’s message.

That brings us to this notion of how he defined value. Thinking about what your values are, but then how you can use those to deliver value to somebody else. Getting up every day and thinking about that, whether you’re an individual contributor or a frontline manager or a leader who’s moving up through an organization or a CEO. All of us are delivering value in our work environments to support others. Be they our colleagues, the shareholders, vendors, customers, whoever. That’s what the world of work is about, is creating value.

If you’re constantly thinking about that and adapting as the world moves on, you will continue to be able to create value and have continued success. That requires, and this gets to another point Dave made, learning agility, being willing to adapt, to let go of old thoughts, to bring in new thoughts, to bring in new sources of information, and to create new ways of learning. Go into conversations where you don’t know the answer and say, “I don’t know. Let’s figure it out together.”

That will become especially important in an era where knowledge is readily available, but wisdom isn’t quite as available. The collective intelligence of bringing people together to solve problems together and to learn from each other will still be a unique part of the human experience and a way that we work even with all of these great AI tools that are coming to bear. A lot to think about from our conversation with Dave.

I hope you found this conversation valuable. If you did, please subscribe or leave us a review. Share this episode with someone who is looking to become a leader or build a stronger career. You can also sign up for my membership community, which is called PathWise and our newsletter, PathWisdom. Thanks for tuning in.

Important Links

• Dave Ulrich
• Dave Ulrich on LinkedIn
• Dave Ulrich on X
• Bob Eichinger
• Center for Creative Leadership
• Mindset: The New Psychology of Success
• The RBL Group
• PathWisdom Newsletter
• PathWise on LinkedIn
• PathWise on X
• PathWise on Facebook
• PathWise on YouTube
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About Dave Ulrich

Dave Ulrich is the Rensis Likert Professor Emeritus at the Ross School of Business, University of Michigan and a partner at the RBL Group. He has published over 200 articles and book chapters and over 30 books. He edited Human Resource Management for ten years, served on editorial board of four other journals and on the Board of Directors for Herman Miller (16 years), has spoken to large audiences in 90 countries; performed workshops for over half of the Fortune 200; coached successful business leaders, and is a Distinguished Fellow in the National Academy of Human Resources. He posts weekly and comments daily on LinkedIn (over 380,000 followers and 3,300,000 page views in 2024) and has a free weekly newsletter with over 230,000 subscribers. His work creates ideas with impact about how to deliver stakeholder value through human capability: talent + organization + leadership + HR.

Finding a job has never been easy, but today’s hiring process can feel particularly frustrating. Hundreds of applicants compete for a single role, AI is reshaping how candidates are screened, and qualified people often struggle to get noticed. At the same time, employers insist they can’t find the talent they need. So what’s really going on?

In this episode of Career Sessions, J.R. Lowry talks with Lorena Prego, founder and CEO of Prometeo Talent, who has spent two decades in recruiting and helped companies make more than 5,000 hiring decisions.

Lorena takes us behind the scenes of the hiring process to explain what recruiters and hiring managers actually look for, and what separates candidates who consistently land opportunities from those who struggle to break through.

They discuss why applying to hundreds of jobs may actually hurt your search, how to take more control of an interview, what recruiters notice when comparing your resume and LinkedIn profile, and how to build productive relationships with search firms. They also explore how AI and remote work are transforming recruiting and why communication, critical thinking, adaptability, and the ability to keep learning will become even more important.

Whether you’re actively looking for a job or simply want to position yourself for your next opportunity, this episode offers a practical insider’s guide to getting noticed, telling your story, and managing your career for the long term.

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/lorena-prego-ojeda/.

—

Watch the episode here

Listen to the podcast here

Why Hiring Feels Broken (And How To Get Hired Anyway), With Lorena Prego Ojeda

Finding a job never feels easy, but for a lot of people now, it feels harder than ever. You submit dozens, perhaps even hundreds of applications, and you hear nothing back. You spend hours tailoring your resume only to wonder if a human being is even going to look at it. You hear that AI is screening candidates, recruiters are overwhelmed, and companies can’t find the right talent. Which is it? Why does hiring seem broken for everyone? In this episode, we’re going to go behind the curtain and talk about how hiring works with somebody who does it for a living. My guest is Lorena Prego, who is the Founder and CEO of Prometeo Talent.

Over the past two decades, she has helped companies make more than 5,000 hiring decisions, particularly in technology and engineering. That gives her a unique perspective on what separates candidates who consistently land great opportunities from those who struggle, even when their qualifications may look the same on paper. We’ll talk about how AI is changing recruiting, what recruiters look for, and the biggest mistakes candidates make.

Also, how to build relationships with search firms before you need them, what catches a recruiter’s attention, and what skills will matter more as AI continues to shape the economy. Whether you are actively looking for your next role, hoping to future-proof your career, or responsible for hiring great people yourself, this conversation will be packed with lots of practical advice that you can start using immediately. Let’s get started.

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Lorena, thank you so much for joining me.

Thank you.

I’m looking forward to our conversation. You have been involved in a lot of hiring over the years. I think something like 5,000 people you have been involved in the hiring of. What’s fundamentally different about hiring now compared with even five years ago or when you started your business?

I started my business in 2010, and I’ve been a recruiter for the last twenty years. It changed many times in many ways. Lately, what changed, everybody’s talking about AI and technology. Companies have access to a lot of information of candidates. Huge databases of candidates. That changed a lot. We use a lot of AI tools. We use tools with AI as well. It changed in that way.

I want to come back to AI later, but across these hiring decisions. What separates the candidates who consistently get offers from those who seem on paper equally qualified, but don’t end up getting the nod in the end?

Overcoming Poor Interviewing Tactics

In my perspective, first of all, candidates are able to communicate properly their experience. I always say to candidates, “You have to be prepared that the interviewer is not very good interviewing.” Hiring managers are not used to doing interviews. They are managers and once in a while they have to interview people.

They’re not usually trained properly, so you have to be able to present yourself. Even though the hiring manager is a bad interviewer. Communication is very important. Preparation is another thing that is very important. Gather information of the company you’re applying for. Organize the things you want to express and communicate in that interview. That’s important.

That point, not all hiring managers are good interviewers. You’ll get some who will have a checklist of questions. They’re going to run you through methodically. You’ll get others who will want to have a casual conversation. Your job is to make sure you get your message across no matter what. For a lot of candidates, they will respond to the questions and think they’re doing great. They will respond to the conversation and think they’re doing great, but they’re missing the opportunity to get their message across.

Correct. Sometimes, I go with hiring managers to interview the finite candidates. I remember once that I was having an interview with a hiring manager. A finite interviewer. I said, “I want to see the way you interview and everything.” The interview was a hiring manager talking all the time. The candidate didn’t say anything. At the end, the hiring manager said, “I love this candidate.” I said, “Why?” They said, “I like her.” I was like, “Why does she want to change now? What is she doing now?” She’s without a job.

I asked him like two or three things. He said, “I should do this interview again.” Usually, hiring managers are based on feelings. I like this person. I identify with this person. This person went to the same university or did the same path. This is crazy. You should try to prepare yourself and organize the things you want to communicate because this person you have in front of you is a manager. Not an interviewer.

A lot of them never get trained on how to do an interview, which is just mind blowing to me.

Correct. It’s not that frequent for a manager to do interviews. They forget. It’s not them to blame. It is what it is. Candidates do not understand this. As a candidate, you have a lot of power in you to be able to have more chances to get hired.

That’s very true because when you’re out doing interviewing, you’re doing a lot of them. You’re better practiced coming into that interview than the hiring manager is going to be. You need to remind yourself, “I’m here to make sure they know this.” Even if they don’t ask those questions, I got to make sure that gets across.

For me, this is fascinating because I do interviews all day. I love interviews and interactions. If you ask me one book that helps everybody to do better interviews like the book, How to Win Friends and Influence People by Dave Carnegie. At the end, you have a person with small things like thank you and you want for them to like you. That gives you a huge advantage. It’s a small thing. At the end, you have a person in front of you that needs to like you to work with you at the end of the day.

It does matter, but sometimes we overemphasize, “Do I like this person? Do I think they will fit into the team?” We don’t zero in hard enough on their actual technical skills. You’ve got to get it both if you’re the interviewer.

That’s why as recruiters, we train hiring managers as much as we can or we are allowed to, but we are not always allowed to do that.

Has remote work significantly changed how companies think about who they are willing to consider in their hiring pool relative to what might have existed pre-COVID?

Navigating Remote Work Timezone Hiring

It changed dramatically in a huge way. The way we work as well in our company Prometeo, because our clients are asking for time zones. They don’t care about countries or cities. They ask for, “I like this time zone plus two hours.” We do look at the map and search for people where they want to search. It changed everything because before that, you had to be in a city or in a specific place to have more chances to be hired. Now, you can be in a small town where cost of living is lower and you’re able to have a great job as well.

Out of curiosity. What percent of jobs that you’re involved in are they willing to consider a remote candidate?

All of them. All of our clients search for remote talent. Eighty-seven percent of our clients are in the US. They search in Latin America and in Europe.

Do you think that’s a consequence of the mix of business you’re in? I know you do a lot of technology recruiting, or do you think it’s because of general factors? I thought at one point, LinkedIn or Indeed, one of them was reporting even a few years ago. That percent of listings that were remote peaked at something like 15%, and then it started to decline again.

In technology, you have this advantage that you’re able to work from anywhere because everything is in the cloud. On the other side, the shortage of talent is something that keeps hiring managers awake. They want to have a bigger pool of talent in a huge geography to be able to find talent. For example, we are hiring AI engineers in Poland because Poland is a great hub of AI engineers, but the company is in the US.

I said we’re going to talk about AI, so let’s talk about AI. It’s hard not to talk about AI when it comes to recruiting. It’s pretty much seeped into just about every aspect of it. From your perspective, where do you think it’s helping? Where do you think it’s hurting?

Leveraging AI Tools Without Spamming

It’s helping in the sense that you’re able to use AI to automatize a lot of admin, and be centered on the most important things. Making the right decision or searching for the correct profile. Sometimes clients do not know exactly what they’re searching for or what they need. On the other side, there are companies that are overusing AI. For example, sending a lot of messages through LinkedIn without any personalization. In a way, spamming candidates and the ratio of responses. At least on LinkedIn, it’s getting lower and lower. You’re able to use AI, but if you use it incorrectly or too much in the wrong way, you damage the process.

For candidates who are frustrated with the fact that they apply to a job on one of the big job boards, they attach their resume, they click the button, and it goes into a black hole, probably viewed by an ATS, an applicant tracking system of some form. Whether they’re using AI or not. How do they get themselves around that process and gain traction when they’ve got a job that they feel like they’re a strong fit for? When you see 500 or 1,000 people applying for a job, even in like the first 24 hours it’s posted, it’s a numbers game that’s hard to win.

Escaping The ATS Application Hole

It is, but to be honest, I’m on the other side. My nightmare is that I need to find talent and I do not find enough good talent. I’m on the other side of the coin. With AI, both sides, candidates are able to apply to many hiring processes at the same time. Companies and agencies are able to access more data. I still believe that you should be applying to hiring processes that are aligned to your skills or your experience. It’s not winning the AI. It’s applying to a position that you are aligned to because if not, you’re getting frustrated, but you’re not necessarily aligned to that position you’re applying.

When people are applying to 100 or 200, when I see these posts online, I applied to my 500th job. My reaction is, “I don’t have a ton of sympathy for that because you clearly are not being focused in your job search.” If you picked 50 out of that 500 and worked at them, you probably would get more traction than you’re getting by blasting 500 resumes out to 500 different firms for 500 different jobs.

Correct. I totally think that as well.

Beyond the recruiting process, specifically, Lorena. How do you see AI changing the kinds of careers that people should be preparing for over the next 5 to 10 years?

Cultivating Essential Future Proof Skills

It’s a tough question. It’s hard because we don’t know exactly what is happening and the scope of what this change means. If you ask me, to be honest, this applies to technology very well. The people in technology and technology changes very fast. The people that go well in their careers are people that are able to learn how to learn and quickly. People that are able to learn new technology or new apps or new ways to do things is the key.

Things are going to start changing and the cycles are getting quicker and quicker. People that are able to learn by themselves, and people that are able to communicate well. Critical thinking is another massive thing because you have a lot of information from AI. Now, you should be able to analyze and think what are you receiving, if it makes sense or not. It’s not only data. It’s the human in the loop. The human that is you as a candidate, you should be able to have critical thinking and process that information in a critical way. Learn how to learn. Be able to communicate properly and have critical thinking.

Some of those critical thinking, decision-making, and problem-solving type skills will always be room for that. You highlighted the importance of continuing to learn. If you’re not focused on making yourself relevant, no matter what the change is, it’s AI now but it was data analytics, was machine learning, mobile applications, and internet many years ago. I can go as far back in business history as we want to go, but it’s always something that’s changing. You’ve got to make sure that what you’re doing professionally is relevant. For a lot of people, that message just doesn’t fully sink in terms of the way that they manage their careers.

Correct. It’s critical to keep on learning, studying, and improve yourself. It never ends.

It does never end. Let’s talk a little bit about this from the hiring perspective. You said a minute ago that you’re out there trying to find talent and there’s a shortage of talent. I see that more and more, this sense of both sides are frustrated. People who are looking for jobs can’t seem to get hired. People who are looking for candidates can’t seem to find the candidates that they’re looking for. Where’s the disconnect from your perspective?

That’s a trick question, and I ask myself that question very frequently. I sense this frustration on the candidates and on the clients as well, because they’re like, “We need to hire a good candidate.” It’s very hard to find a good candidate.

Maybe use an example or two of where that’s playing out in something you’re working on. Is it the companies in a bad location or the salary’s not enough or they’re asking for things that are unrealistic? I’m just curious where the bottlenecks tend to be from the hiring firm’s perspective.

Resolving Corporate Hiring Bottlenecks

You’ll be surprised. Usually, the first gap that we find in our clients is that they’re searching for something that they don’t need. They’re searching for a person that in technology is full stack is front-end, back-end, DevOps, and QA. These are four roles in one. It’s like, do we need to find this person? Where is the priority? What is the problem or the challenge you need to solve?

Therefore, we help them to organize their hiring process or their job description and determine that what they need is only a UX or UI, like a designer, for example. This is the first gap. Every company’s CEO or COO main challenge is to have their costs under control. Every hiring, in a way, is an investment for the company. It should be controlled. They try to solve many challenges with one role. I don’t know if it makes sense. That’s the first gap.

The other ones are, for example, they want someone with a lot of experience, but the budget is very low. It’s like, are you able to hire someone junior and go through the gap of training this person? If not, we need to hire someone with this seniority or sometimes the company is not willing to invest or they want to hire someone they’re not able to hire.

Sometimes you get a hiring manager who just wants to have another person on their team. DevOps, full stack developer thing. It’s like wanting a unicorn because they don’t know exactly what they need. They just know they want somebody else.

Exactly. There are many problems. Sometimes, in the hiring process, the problem you find is that the chair manager and the hiring manager are not aligned. They interview someone and then the hiring manager is interviewing someone else. They’re not aligned and they’re searching for different things. The candidate goes through the interview, but then the hiring manager says, “I don’t like this person.” I have a fintech and we’ve been searching for six months and one says yes and the other one says no. The HR says yes. There’s no alignment or whatsoever. It’s very hard.

Which I’m sure is very frustrating to all involved. If it takes you six months, there’s a message in there for the hiring firm that they need to rethink what they’re looking for and what they’re willing to give.

When this happens, what we agree with the client is that what you need is a consultancy process. Not a hiring process. We do start working as a consultant in terms of who is involved in the process, how we can align this process, and why you’re not getting any results because the company is frustrated as well.

What are some of the other things that tend to separate the organizations that are good at hiring from the ones that are just more average?

The companies that are good in hiring first are the ones that they know what they’re searching for. Not only skills, but culture. That’s very important because it’s important for you to hire someone that is aligned to the company they are going to be working at. The other one is that the companies that train their hiring managers in interviews are. These companies that are able to understand that they don’t need to hire replicas of the hiring manager. They need to build a team and the team members should be different from each other and from the hiring manager. If you find a team that everyone is the same, like a replica, we are in a huge problem.

Diversity is a benefit. Whether you’re thinking about it in whatever form, but certainly diversity of thought, background and experience in a team makes a huge difference. To have 5 clones or 10 clones of the hiring manager just means that you’ve got a collective blind spot because they’re all good at the same things.

Correct. Another thing that is getting great hirings is candidate experience. That the candidate has a great experience through the hiring process. The companies that are working on their employer branding. That is, they start communicating what they’re doing internally to be able to connect with potential candidates in the future when they want to hire. They’re investing on communicating what they’re doing inside.

A lot of companies, like a lot of candidates, most candidates don’t worry about this until they need a job. Most hiring firms don’t worry about what they’re looking for until they need to fill a role. Both sides need to do more to prepare.

Exactly. Companies that work on their employer branding get better applications and candidates because they are all out there already.

Anything else as a recruiter that you wish hiring organizations would do better or differently to make the process better?

Flexibility. Usually, we get frustrated. It’s hard to work with the client that is rigid. We go to the market and we give the clients a lot of data. Where is the client located geographically? What are the skills and the salary ranges? We give them a huge scope. Especially with AI, you’re able to scrape data and you’re able to have a lot of information. When they say, “I don’t care about this data. I want to go there because I want to.” I’m like, “This is going to be hard.” When we give the clients feedback, they are able to fit things a bit more flexible.

I want to come back to the candidate’s side. You talked earlier about the best candidates being better communicators. What are some of the mistakes that you see candidates making when they’re trying to tell their professional story?

One is not knowing that they have more control in their interview than they think. Sometimes candidates talk too much and are not accurate about the position they are applying for or their skills. The candidate should be responding with what they’ve been asked. The candidate’s so nervous that they start talking nonsense. Be accurate. When you said what you wanted to express, make a pause. If the interviewer is not very good, they don’t know how to manage time and how to interrupt you a bit to do another question because they have a list of questions they have to do. If you talk and talk, you are going to make yourself worse in the process.

I’ve certainly seen candidates who ramble. It is hard for most hiring managers to pull that back in to make sure that you end up getting the questions answered, then 30 or 45 minutes or 60 minutes goes by and you’re like, “I didn’t get all my questions asked.” That’s a problem for you in the end, because then you’re making a less informed decision or you have to have the candidate come back again, which is a bad use of everybody’s time.

At the end of the day, as we said before, prepare for the interview, and understand what are the topics you want to talk about, but be accurate because this person is going to interview many people. Not only you. Probably three at least. If you’re not accurate, this person will forget what you said.

What advice would you give candidates in terms of how they work with you? The search for morals is fairly opaque to most people, but what’s the best way to work with recruiters who tend to work in the markets that you are looking for work in or working actively in?

To give you data. In our database, we have 100,000 candidates. They’re current candidates. They are not older than eighteen months due to GDPR. If every candidate wants to search for a job, contact me through LinkedIn saying, “Could you find me a job?” It’s very difficult because I’m searching for the positions that I have.

Usually, what I recommend is for candidates to connect with the recruiter after they apply for the position they want to and tell the recruiter, “I found a hiring process that I could fit for.” It’s something to connect and then the recruiter will look at your LinkedIn and if it makes sense, will make you go through quicker. If you connect with the recruiter every time you want to search for a job and it’s not in their pipeline of hiring processes. It doesn’t make sense.

Does it make sense if part of the traditional wisdom has been that you should build relationships with recruiters when you don’t need a job because then they know who you are? In this era of databases and artificial intelligence, do you still need to have relationships with recruiters or do you just need to be in their databases?

Both. If you’re not in a database, it’s harder for us to search for you. What I would say is that when you participate in a hiring process, although you’re not hired or you’re not moving forward, make a professional way through the hiring process. Do not disappear. Don’t be a non-responsive candidate. Things that make you look unprofessional.

In the future, when this company or agency has another hiring process, we’ll consider you as a potential candidate. You never know. Make a good impression. Behave professionally in every hiring process because you never know. That’s building a relationship with an agency or recruiter because we have notes on our databases and we say, “Strange behavior. Non-responsive. This is not professional.”

As a simple example. A lot of people don’t take calls from recruiters. They ignore them. I always tell people, why not pick up the phone and take the call? At worst, it’s going to be ten minutes out of your life but you have an opportunity to at least get on somebody’s radar. Maybe get something favorable entered in their database about you as opposed to something unfavorable about you. Why would you not seek that opportunity? For a lot of people, it’s like, “I’m not looking for a job. Why should I talk to a recruiter?”

Maybe as a candidate in the future or now, you can have more data about what your value is in the market now or other conditions that you can ask for your current employer. There’s nothing to lose.

I agree with you. You must look at an awful lot of resumes and LinkedIn profiles. What types of things catch your attention positively or negatively?

Aligning Resume And LinkedIn Profiles

For example, what we do is that we ask for the candidates to attach their LinkedIn profile, paste the link, and also if they want to, attach their resume. The thing I do now is compare their resume to their LinkedIn profile. If they’re incoherent, because LinkedIn is public. My guess is that the candidates are more honest with on LinkedIn than their resume. It’s like, if there is a huge gap between both, this is a huge red flag for me.

On the other side, jumping from one job to another, gaps in their experience, and things that are too big. You’re not like, “I’m the manager or responsible for,” and you’re not clear on what. If you go to the LinkedIn company, they are the only employees there. Probably, it’s their own company. At the end of the day, we want transparency from the candidates. It’s both ways. I’m very honest when I find some candidate that is not suitable for the company. I tell them, “I don’t think this is the right position for you. Anyhow, if you have any questions for the future, let’s get connected.” Again, for the candidates, we expect the same.

I just think a lot of candidates don’t think enough about these kinds of things and the way that they’re coming across. It’s pretty hard to be invisible. Some people actively take themselves out of all forms of social media as a way of maintaining some semblance of privacy. The vast majority of people don’t do that.

All these data points connect a perspective on you. You can go to pick your favorite AI tool and say, “Tell me what about me.” That’s the same thing you’re doing, I would imagine. When you have a candidate that you haven’t had any exposure to before because it’s a way for you to gain information about them. If you don’t like what you’re reading, as a candidate, you probably need to do something about that.

The senior candidate or the profile is, the more information as a recruiter, we’re going to search for. The company they work for, the consistencies, and inconsistencies. You should be more aware of these things.

Last question. From everything we’ve talked about, Lorena, if you were going to leave our audience with one bit of advice from all of these thousands of hiring decisions that you’ve been involved in. What would it be?

If you ask me, I should say, do what you love. Working takes a lot of time. I know it seems romantic. Maybe I romanticize, but if you have to be someone that needs to be learning all the time, improving yourself all the time, because it’s very competitive. You’re competing against the whole world. Not the whole world, but it’s geographically bigger.

If you enjoy what you’re doing, you’re always improving yourself, studying and getting better and better. One thing is do what you love and keep on learning. Keep on listening to podcasts. It’s very realistic. It’s not like a book that was published many years ago. No. Keep on searching for information to improve yourself and your career nonstop.

Very good advice. I agree with the notion that you should continue to invest in your career journey because otherwise, things are going to run out of rope for you at some point. Thank you for doing this. I appreciate it. I’m sure our audience will get a lot of good insights out of the discussion that we had. Thank you for spending the time with me.

Thank you very much for this episode and the invitation.

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What do I want you to take away from my discussion with Lorena? Hiring has changed a lot since 2021. It started with the pandemic and the impact that had on remote work. Now, we’ve got AI to contend with. All of those things have transformed how companies recruit, but employers are still looking for people who can solve problems, who communicate clearly, who will create value, who will collaborate well with their colleagues. That’s what you need to be showing them in your social media profile, in your resume, in your cover letter, in your interviews, and your references. It all needs to be coherent.

Second, remember that your resume gets you noticed, but your story is what gets you hired. You have to get that across. The strongest candidates connect the dots. They explain their impact. They make it easy for employers to see why they’re the right fit. Importantly, if you’ve got a hiring manager that is not letting you get at that, you need to find a way to get that message across when you’re in the interviewing process.

Third, think of recruiters not as career agents. They are business partners. Understanding how they work, when to engage them, how to interact with them, how to build relationships with them will dramatically improve your career opportunities over time. You definitely want to be in their database, but you also want what’s in their database to portray you favorably.

Finally, treat your career like a long-term investment. Not just a series of job searches with a drab job in between. The people who are consistently landing the best opportunities are building skills, growing their network, strengthening their reputation, and staying visible long before they need their next role. That’s what true career management is about. As always, I invite you to subscribe to the show on Apple Podcasts, Spotify or YouTube. If you found the discussion enlightening, please sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks.

Important Links

• Lorena Prego Ojeda on LinkedIn
• Lorena Prego Ojeda on Instagram
• Prometeo Talent
• How to Win Friends and Influence People
• PathWisdom Newsletter
• PathWise on LinkedIn
• PathWise on X
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram

About Lorena Prego Ojeda

Lorena Prego is the Founder and CEO of Prometeo Talent, an international recruitment firm connecting companies in the U.S., Europe, and Latin America with exceptional talent. A psychologist by training, Lorena transformed her understanding of human behavior into a career that has shaped the hiring strategies of startups, scale-ups, and global organizations, helping companies make more than 5,000 strategic hires over the past 15 years.

She is also a professor at Universitat Pompeu Fabra, in Barcelona, speaker, and a recognized voice on leadership, careers, and the future of work. Few people spend as much time studying the tech talent market as Lorena. She follows the industry, analyzing how artificial intelligence, new technologies, economic shifts, and changing workforce expectations are redefining the way companies hire and professionals build their careers.

Her perspective comes from the front lines. Every week, she works with founders, executives, and candidates making critical hiring decisions across multiple countries. That combination of psychology, business strategy, and hands-on recruiting gives her a unique view of where the market is heading and what separates companies that consistently attract outstanding talent from those that struggle to grow.