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Leadership In The First 90 Days, And Career Best Practices, With Amy Philbrook

Stepping into a leadership role in a new organization means not only a fresh start for your career journey but also for the organization and the people within. You bring with you your experiences and offer new perspectives on what they need. Amy Philbrook is currently unlocking this career milestone. After spending more than 25 years in a wide variety of roles at Fidelity Investments, Amy is now starting as an Executive Vice President for Service with LPL Financial. In this episode, she shares with us how she is handling this transition period, how she is thinking about the first 90 days, and where she wants to focus her energy. Amy talks about dealing with culture shock and adapting her own leadership style and then offers insights on what people get right and wrong in managing their careers. Tune in now and embark on Amy’s career journey!

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Leadership In The First 90 Days, And Career Best Practices, With Amy Philbrook

Executive Vice President For Service With LPL Financial

My guest is Amy Philbrook. She is the Executive Vice President for Service with the LPL Financial role she just started. She previously worked at Robinhood in roles focused on customer care, operations and learning and development. Prior to that, she spent more than 25 years in a variety of roles at Fidelity Investments. Amy is also a public speaker and thought leader including CNN, the Society of Human Resources Management, Bizwomen, and others. She works in the Fort Worth, Texas area. Amy welcome, it’s great that we’re getting to do the show together.

Thank you. It is a total honor and a pleasure for me.

The honor goes both ways. Congrats on your new role. Do you want to start there and tell our audience about LPL and what you’re doing for them?

I’d be happy to. This is my third week with them. I am brand new and deep in the learning curve already. For those who don’t know, LPL is a broker-dealer here in the United States that has a sole focus on serving financial advisors. What was exciting to me was the chance to work for an organization that supports others and their journey to grow their business and be amazing for their clients. I haven’t had that privilege before. It’s yet another twist in the road for my career and that’s why I was excited about the opportunity. I’m going to run all of the customer service for them. Customer service and customer care operations are very familiar territory for me, but the client base and focus on business owners and entrepreneurs and folks growing their practice is totally new.

That would be fun. How did this come about? How did you first hear about the role?

Like lots of great opportunities that came through those relationships, there was a Fidelity alone that I have had the privilege of working with during our Fidelity days who is an MD at LPL and interestingly, when they were talking about filling this role, they talked about wanting somebody who had seen the scale and quality of a fidelity-like company, but could run at the pace of an innovative startup. Having Fidelity and Robinhood on my resume, I fit that bill.

What else appealed to you in terms of the opportunity?

The people. I’m never going to take an opportunity where I don’t have high confidence that I’m working with collaborative well-intended people. I kicked the tires pretty hard on the culture there and I found that it held up under scrutiny, things like diversity, inclusion, development, career paths and mobility are all top of mind at all levels of leadership including the CEO. That was appealing. It offers up a whole new learning opportunity for me. It’s early days but this is probably one of the best fits where my experience can create immediate value for them, but they can immediately welcome me to a new learning space as well.

You’re a few weeks in as you mentioned. How are you thinking about the first 90 days and where you want to focus your energy?

I hit the ground running. I spent week 1, Monday through Friday, in San Diego, California meeting with as many people, partners, leaders and my people as I could. Week 2, I spent Monday through Friday on the ground in Charlotte North Carolina doing the same. For me, the first 90 days are all about maximizing engagement. I want to hear the points of view of the business from the C-Suite. I want to hear it from my service associates who are talking to customers on the end of the phone all day every day. it’s a lot of learning and listening. It’s also about connecting the dots.

What I’m finding is you have this beautiful opportunity when you’re new to ask questions and try to connect the dots for yourself. It turns out you uncover some a-ha and you create some a-ha moments for others. Everything from talking to corporate real estate about site strategy, and equipment strategy and connecting that to our human capital teams about the learning process and speaking to proficiency and how those two things work together. Every opportunity I have to try to vocalize where dots may or may not connect is not only strengthening my learning and accelerating my journey. It’s already creating leverage opportunities for others.

You have this beautiful opportunity when you're new to ask questions and try to connect the dots for yourself. It turns out you uncover some aha moments for others. Click To Tweet

I certainly remember when I started at Janus Henderson. It’s been a little over two years. I went in and asked a ton of questions. I did a ton of meetings. You’re in massive fact-gathering mode, reading everything you get your hands on, but even in questions that you ask, you’re giving people who have been there longer a bit of a sense of, “What somebody with a fresh set of eyes wants to know about this operation writer, this business? What are their questions about? What are their observations?”

I spent a lot of time in those early meetings sharing my thoughts, be speaking too soon or out of turn before you have your fact-based together. I think if you do it in the right way, it helps because then they start to open up a bit more and you share what you’re learning and how they’re thinking about things and things that have been on their mind. That’s been good since then.

There have been three things I’ve tried that have served me well in that because I worry too about you don’t want to come in and be the person who says, “We did it this way.” I did three things. I recruited two people who are going to be in a lot of meetings with me and I said, “Let’s have a little signal for when I’m over-sharing or overstepping. You know the culture here better than me. You’ll be my manager or handler to tell me like, ‘Pull back here. Keep going lean and more.’”

The second thing I did was I started asking people, “What’s interesting to you about that?”When somebody is talking about something, they’re going deep on a particular point. I find I unlock a lot of the history and the culture and the context if I say, “When you’re spending a lot of time on this, what makes this interesting from where you sit in the business?” That’s not a question you hear a lot. You hear a lot of like, “We’re spending a lot of time on this. What does it mean for me?”

When you ask somebody, “What’s interesting about this for you?” it opens them up, I have found, in a beautiful way. The last thing is I’m trying to moderate when I share base, I try to say, “Based on experiences I’ve had, here are some of the things that have worked well, how do you think that would play here?” rather than saying like, “In Fidelity or Robinhood, we did it this way or that way.”

There’s always a danger as you say, “When I was at such and such place.” You mentioned some of the diligence that you had done to get yourself comfortable that this is the right place for you. What else did you do once you had the offer everything was agreed to get yourself prepared before you started.

I took off to Italy and spent a couple of weeks clearing my head hiking in the mountains of Northern Italy. I was in a situation in my career I’d never been in before. I resigned from Robinhood and wrapped up my tenure with them in July 2024 with no plans to even look for a job for the rest of 2023. It was going to be the first fallow period in my career by design that wasn’t a maternity leave which for me is two decades in the rear-view mirror. It was a difficult decision to make. I’m somebody who likes to do a lot of my identity and self-worth can be tied up in what I’m contributing professionally to an organization.

To make that decision was difficult, but what I found was I had a little bit of space and time. I didn’t look for a job, but certainly, opportunities and interesting ideas came my way. Because I had some space and some silence, I had real clarity real-quickly about what I needed, what I would tolerate, and what I wanted to leave behind forever.

When I accepted the offer, I spent a lot of time reminding myself, “Why was this the right opportunity? What are my must-haves? What are my okay to tolerate and what are my boundaries going to be?” I got grounded in those things and tried to make sure I had a plan for when there’s a crisis, how am I going to hold to these values in these boundaries when things are going great? How am I going to curb the temptation to overextend? That time was important and valuable. In the earlier days, two weeks in, but I feel like I’m starting off in the right place.

There are two things you mentioned that resonate with me. 1) There is value in giving yourself forced time in between jobs when you have the luxury of being able to afford it because it does give you the ability to step back to do a bit of reflection, to think about what you want in your life, your professional life and your personal life.

It’s a lot easier to do that when you don’t have the constant inbound. I’ve had that twice in my career where I’ve had a bit of time to reflect a bit on what I wanted to do next and it’s been very helpful. The other thing you mentioned I think is interesting is the idea of what you want what you’ll tolerate and what is the deal breaker?

Having that clarity on those things in particular great screening mechanism for thinking about potential companies and opportunities roles within those companies because if you know what you want then it is a two-way street, this idea of interviewing and a lot of times people are anxious to get a job and sometimes financials definitely plan to that. If you aren’t in that situation, it does you a world of good to be clear on what you’re looking for, then you can measure everything against that as opposed to it’s a very sense of what you’re after.

It’s a luxury for sure. I don’t think it’s any mystery that I’ve been working for 30 years before I was in a position to take this opportunity and view my next move from this strategic of lens. I wish this is something that we could create for everybody periodically and much earlier in careers.

We don’t have extended holiday time in the US. We don’t have sabbaticals and most companies, but there is some value sometimes to getting those breeders right and a chance to reset. You spent a long time at the beginning of your career at Fidelity, like a lot of people. A lot of people have stayed at Fidelity for a very long time. When you think back to those early days when you were fresh out of school and in your first role or two, what do you remember about learning about yourself and the world of work back then?

It was certainly different than I thought I was going to be. I started at the end of a 1-800 customer service number at Fidelity. I learned quickly communication skills were going to be my most important currency. I feel lucky that I fell into that role because having to talk to empathize with understand and take action for anyone who can show up next at the end of your phone line and you have no idea what you’re going to need to be prepared for, tremendous dexterity of communication skills.

I feel super lucky that I started my career in service. I also learned that have to self-actualize your career path. People are not going to hand you things no matter how good you are at your current role. I’m curious by nature. One of my stronger skills is asking good questions. I started asking a lot of questions. Some of those questions were things like,  “Can I shadow you for a day? I’ll use one of my PTO days to Shadow you because I don’t know how else I’m going to learn about what somebody you know who doesn’t sit right next to me does all day long.”

I learned that people were open to that. I had a mentor who talked about R before T or Relationship before Task. I would never go to somebody and say, “I want a job on your team. What do I need to do to get there?” I would go to somebody and say, “I’m interested in your area and learning more about it. Is there someone on your team I could shadow for an hour that you think would show me how things work here?” That’s putting the relationship and my interest in them ahead of what I want the task of landing a new job. I learned early on, be self-actualized, ask questions and don’t be afraid to spend my own time and energy learning about the places I want to go.

You’ve spent many years in financial services. When you are on the other end of the phone line and you’re talking to somebody who’s taking a hardship loan against their 401(k), is having to you know process a death event as the surviving beneficiary. I always valued the time that I spent listening to phone calls when I worked at Fidelity and I’ve done a little bit of that at Janice as well because you do get a sense of like, “These are real people out there who are saving children education and retirement.” It’s easy to forget that sometimes and to get caught up in the internal squirrel of things going on. For me, those times spent listening to those phone calls big ground you and they remind you of the why. I’m sure you’ve carried that with you over the years.

I was telling my boss I love to take escalations because that’s where you learn what matters to the customer and I can’t wait to talk to the clients at LPL MRI. I’ve been here for two weeks. I’ve talked to three of our end customers, and advisors directly already, engaging in some relationship building and the more time I can spend on the front line with our service teams or talking directly to our end customers the better I’m going to be able to serve the organization.

CSCL Amy Philbrook | Leadership First 90 Days

Amy Philbrook: The more time I can spend on the front line with our service teams or talking directly to our end customers, the better I’m going to be able to serve the organization.


Coming back to Fidelity for a minute. You were there for 25 years and had 14 different roles by my count on LinkedIn. Your role spans and I have to look at the list of customer service, client relations, marketing and sales risk and compliance technology QA, HR, DE&I. That’s a lot of different things. In all of these different roles, how many were situations where somebody tapped you on the shoulder and said, “I have a great next role for you,” and how many of them were roles that you pursued?

I’d add a third category, “How many were roles that I created?” It was equally 1/3. You might think, “The shoulder tap didn’t come until the later years.” That wasn’t true. What I found was the shoulder taps came more often earlier in my career. It’s easy to differentiate yourself from the herd if you’re an execution superpower. If you’re like, “I will hustle and outlearn everybody around me,” you can become visible pretty quickly and get those taps on the shoulder. The midpoint of my career is where role creation came into play.

I would have ideas and pitch them. I would say, “Who’s going to bring this to life? Why not me?” Some of my roles in sales, technology and sales operations came about from pitching an idea, seeing a need, figuring out a way to solve it, pitching an idea and then turning that into my role. It’s been later in my career where I’ve pursued things. I remember telling my boss at the time when the head of diversity and inclusion for Fidelity announced that he was going to retire. I said, “I want that job. I need your advocacy and support in order to get it.”

He was like, “Why that job?” I said, “It’s going to be important and I can make a difference.” I had to go on a campaign to land that role. There wasn’t a lot in my background that would suggest that that was a natural next step for me, but I didn’t feel like I had the credibility and the currency until this latter part of my career to go after roles that might not seem like a natural fit.

What was important to you otherwise in picking the roles that you chose to do next?

I wanted to know that I could create value, and impact and that I could learn something. It was as simple as that. It needed to be new territory for me, but territory where I knew my skillset, approach and my processes would add value. There was one pivotal development experience in my career that unlocked that for me. It was 2010 or 2011. I got to go through the Stanford Design School course on Design Thinking, and I fell in love with it.

It’s a very human-centered but practical tactical problem-solving methodology. I learned as much about it as I could. I joined an extended team of people around the firm that would teach it, coach it, and lead engagements outside of their business unit. Once I locked in on mastering a methodology that could bring value almost anywhere, all of a sudden, I had the currency to carry with me to say, “I can go to almost any area of the firm and add value because I’ve got a methodology and a process that works.”


Certainly, the idea of customer journey mapping which is closely linked to design thinking. We were doing a little bit of that when we were working together there. If nothing else it forces you to put yourself in the shoes of your customer, design thinking is the same thing. It’s an empathetic way to be thinking about how to design products and improve products and services.” I’ve certainly taken it in my different roles over the years as a tool that I pull out somewhat often to understand how we’re delivering service.

I spent about ten years at Fidelity once I acquired that skill set where I wrote my own employment contract. We don’t have employment contracts like that. Every time I got a new role or I worked with a new manager, I would say, “I spent 20% of my time working outside of our department, facilitating design thinking engagements for other areas of the business, but in return, here’s the value I bring back if you agree to let me do those new relationships, new connections, new leverage points and new understanding of the customer from different angles.” I never had a single manager turn that down. That was that’s another strategy. I coach people on that I coach and Mentor today is like, “What can you uniquely do outside of your own front yard that will bring back added value, not just for you, but for the team that you’re serving as well.”

What are some of the other things you did to position yourself for success when you started a new role? You have a lot of practice at this.

I do have a lot of practice at this. I’m a disciple of The First 90 Days that management book. In your first 30 days, you meet as many people as you can, both customers, whether they’re internal customers or external customers as well as business partners and team members, and then you get strategic about,  “Who are my advocates or my champions? Who do I need to win over who’s going to be in the adversary column? What’s my relationship-building approach going to be for folks as they fall in these different columns?”

When I say adversary, it’s always, “We’re going to be competing for resources or r priorities. It’s never more adversarial than that,” and then structure my relationship management approach. The other thing is to get clear on what success looks like. What I found both somebody new being hired and somebody who hires a lot of people, usually we have one idea, “This is what success is going to look like for you in this role. These are the key metrics and KPIs or stretch goals.”

Sixty days in, you got to revisit that conversation because both of you have changed your minds. I learned that early on as well. I always make sure we have the defining success conversation at least three times, me and my boss, in those first 90 days, and that’s been beneficial as well. A lot of people have that conversation once. It’s said it and forget it. Six months down the road, you’re like, “I’m not even working on this stuff anymore. It’s not okay.” Having that conversation early and often has been another thing that I’ve learned.


At some point along the way, you were a new manager. I’m curious to know what that experience is like for you and what surprised you most about being a first-time manager.

My first manager role was as a team manager of a phone team for Fidelity Investments. It was an incredible experience because I was now managing people who were doing what I had done. You’re never as set up with expertise subject matter or expert knowledge as you are in your first manager job because you usually get promoted to run something that you used to do. I had that blessing in that curse of having done the job of the team that I was now leading.

Instant street cred and deep subject matter expertise, you don’t get that later in life in your career. You end up managing things that you haven’t necessarily done. You don’t know backward and forwards. I think what surprised me was that subject matter expertise was limiting when it came to being a good leader for my people. I made the mistake of over-directing and overdoing it. I think it’s Liz Wiseman who wrote Multipliers. I was a rescuer. I would parachute and solve the problems because I could.

I was very uncomfortable letting my people struggle and experience the pain that’s necessary sometimes to facilitate growth. If I could do one do-over well, I have a do-over right now. I don’t know LPL’s business as well. But I’m managing a very tenured experienced team. What I’m excited to test myself on is, “Can I raise a bar for them? Can I give them new challenges and new frames of reference to look at the business through, but then let them struggle where they need to struggle in order for them to elevate even higher?”

That’s one of the things a lot of first-time managers struggle with particularly, in a situation that you are in because you’ve done the job right as you said. You know the backward and forwards. It’s easy to become the rescuer in those situations. There are times when you have to say, “What are you going to do about that? What do you think you should do?” You keep the burden on them to figure out how to solve the problem because that’s the way that they grow, but it’s a bit counterintuitive for most first-time managers.

You get promoted because of how much you can do and it’s uncomfortable to sit on your hands, but there are many opportunities that come if you can be a little bit patient.

I think about deliberately waiting to respond to certain emails. It’s a bit like not being the first one to jump in to talk in a meeting. You want the discussion to flow whether it’s in an email or in a room, and you got to let your team chime in on things themselves first, but it’s hard. I think we all have a bit of the rescuer and that’s right. You went under Robinhood after a long run in Fidelity. It had to have been some of a shock to the system to move to a smaller place, a place that was in hyper-growth mode at the time.

It was exciting. I’m definitely jumping into the cold water in terms of shock to the system. Everything was different. I didn’t even know how to use the basic operating system on the computer because they Google Suite. I had never worked with that. They use Slack. There was no email. Most meetings were fifteen minutes long. I am talking about a dramatically different operating dynamic, but that’s what I wanted.

I remember when I was interviewing there, I was talking to the CEO at the time Gretchen Howard who’s a wonderful mentor and coach for me. Fortunately, she had worked at Fidelity back in the day. She knew the culture shock I was going to experience. I told her I was looking for an adventure and all of those different dynamics were part of contributing to that sense of adventure. It was culture shock, but it was also an incredibly collaborative organization and to use her words, high execution with high humility and high Intelligence with high humility. I found that to be true.

There was nowhere that I couldn’t turn to ask for help. It was about me being humble enough to ask. I had to ask 1 million questions a day for probably the first 6 to 9 months. It’s a very technology-oriented company. They speak a different language. They operate in different systems. being humble enough to ask those questions, but ask them quickly and do a lot of self-serve.

I would spend a lot of late nights, digging for information, reading every Google Doc and figuring it out. The other thing is they did have an operating manual that was based on a cool book called Working Backwards. It’s the Amazon book. It’s the book about how Amazon runs or used to run. Robinhood had a bunch of influential leaders that had an Amazon background. They worked to leverage that methodology. Finding that resource early on and understanding that I had to take it seriously helped accelerate my integration.

CSCL Amy Philbrook | Leadership First 90 Days

What were some of the ways that you felt like the cultures of Fidelity and Robinhood were similar and how are they different?

They definitely similar in terms of customer obsession. Everything was about the customer at both firms, definitely similar in the fact that they would leverage the platform and systems-level thinking and solutions to scale. Neither of those are firms that solve a problem by throwing more bodies at it. You’ve got to find a way to automate and solve that scale. They were very similar in those respects.

I would say where they were different was the tactics of how they got work done. For example, Robinhood was all slack no email and it was not a meeting-heavy culture. There were also no slides or PowerPoint presentations, but on the flip side, there were docs deep narratives with lots of collaboration and commentary.

It’s a very Amazon-centric tool. Those things were very different and then access to the CEO. One of the benefits of Robinhood being a smaller company is anybody had access to the C-Suite and everybody got to hear directly from the CEO and the C-team on a weekly basis highly unscripted very personal and intimate dialogue very different culturally from a curated structured environment like Fidelity.

How did you have to adapt your own leadership style?

I had to get comfortable with casualness and a highly engaged and empowered workforce who felt like they could push back on any executive about anything at any time. I found myself on the hot seat in situations that I didn’t have any opportunity to prepare for in front of the entire company on multiple occasions. That caused me to raise my game. It was a wonderful and uncomfortable experience but a very enriching learning experience. The C-Suite were the most data and metric-driven people. You couldn’t go in there and talk about anything that you didn’t have numbers to back up. That raised my game on analytics as well.

I can imagine in particular that a casual environment where people can push back had to have been different. I contemplated taking a job at Bridgewater at one point when I was leaving Fidelity. That was another place where the idea was it anybody could tell anybody what they thinking. Going back and forth to Connecticut for the interviews, I’d be sitting in the car thinking like, “Can I see myself in this environment?” In the end, it didn’t work out anyway, but cultures can be different. Things that made you successful in one may not work and vice versa.

We talk about Oregon rejection a lot at every company. There are certain people that you bring in and the risk of organ rejection gets higher the more responsibility you carry. I enjoyed the challenge of adapting to such a different culture. That doesn’t mean that I decided it was the right culture for me long-term. I made a decision to exit that culture.

Culture was a part of that reason, but I would encourage everybody to experience as many different cultures as you can. I had a wonderful leader early on in my career at Fidelity named Sunil Kumar Singh. He told me like, “Go as many different places in the world as you can. Try as many new things as you can. All of these experiences add to the sum total person that you are.” I view changing jobs and changing workplaces as much a part of that as trying any new adventure whether it’s moving where you live eating different foods or listening to different media. I try to consume a very wide variety in my diet of experiences.

CSCL Amy Philbrook | Leadership First 90 Days

Amy Philbrook: Go to as many different places in the world as you can and try as many new things as you can. All of these experiences add to the sum total person that you are the same as changing jobs and changing workplaces.


I think that openness to new experiences in whatever form they take, food, travel, places you live or work and team cultures. Some of it will work. Some of it won’t work but it all helps blend into what you take with you and the rest of your life. There have been situations. I was at McKinsey for a while. The one benefit of being in the consulting world is you’re constantly moving from one project to another.

There were some companies that I didn’t like working with. There were some I loved working with there were some project managers I liked and didn’t like, but the thing is you learn from all of that. You learn what matters it comes back to, “What’s important to me? What will I tolerate? What is a deal breaker?” All of that feeds in and helps you crystallize that more as you continue to your career. The only way to do that is to see different things.

That’s what keeps life interesting and engaged. In my opinion, it is what keeps us young.

I know you were a student of leadership and career development who has been big influence for you in terms of leaders that you’ve worked with or people even maybe that you haven’t worked with so much that you admire?

You are one of them. I look at what you’re doing. You have a high responsibility, visibility role and established firm, you have this business that you’ve created out of your passion that’s become I would think more than decide hustle. It’s meaningful for people in the world. I don’t think it’s just leaders that I’ve learned the most from. I think that you can learn from everybody above, beside and below you. I haven’t met a person on this planet that I haven’t been able to learn something from.

Some of the people I’ve learned the most from are my kids. They’re navigating a world in an economy, landscape and climate. It’s totally different than what URI navigated when we were emerging out of college and starting our careers. I tend not to think of like big luminary names. I read a ton. The practitioners like Daniel Pin, Adam Grant or Liz Wiseman and her work on multipliers, like certain things have stuck with me in the art of leadership.

I try to be on the lookout for if there’s a restaurant that I go to that I like, sometimes I’ll ask to talk to the floor manager and say, “You have an amazing team. What’s your secret?” I went through a drive-thru at McDonald’s here in Fort Worth. They had a bunch of service team members in the parking lot servicing cars at the window. I’d never seen McDonald’s do that before and I said, “What do you do?” They said, “We learned it from Chick-fil-A.” If you’re a student of leadership, you keep your eyes open and wherever you see goodness, ask questions. Find the person responsible for that and ask them what inspired them. That’s more my methodology than having certain people I follow or principles that I adhere to.

If you're a student of leadership, you keep your eyes open. And wherever you see goodness, find the person responsible for that and ask what inspired them. Click To Tweet

How would you describe your own style at this point in your career?

Ever evolving. I would say my style is a combination of curiosity, empathy and high standards of excellence. There is a leader that I worked for at Fidelity for a number of years named Andrew Tappe. He taught me something simple. He said, “There are three questions that you want your teams to be able to say yes to when somebody asks them about you. Do you care about your team? Can they trust you? Are you committed to excellence?”

My leadership style is always striving to get a yes on those three things. I do it by spending time with people getting to know them being super clear on expectations both ways. In my one-on-ones with my new team I said, “I want to hear about what you need to feel supported and challenged by me. What does that look like for you? How does that work for you?” Lots of context and Clarity around expectations and then constant communication, “What am I thinking? What am I doing? What am I worried about?” I want that back two-ways.

What do you see as the most important decisions that you make as a leader?

The people on the team, do I have the right people in the right seats facing off with the right work? That’s what it’s all about every day.

What do you look for when you hire people into roles?

I’m not really good at hiring people. What I’ve learned is I can be a good interviewer. I can ask great questions, but I don’t necessarily form a great judgment about people quickly. I learned that about myself early on from building teams that weren’t so high-performing and didn’t work so well. When I’m interviewing I’m looking very carefully at who else is on the interviewing committee and how are we going to make a decision. What I try to suss out is, “Can I find the best candidates? Can I find the best people to complement what I don’t know and what I lack and judgment?” I try to build good interviewing teams.

You think so much of interviewing as I’ve seen it, people go into the interviews the interviewers, go into the interviews not prepared if there are 4 or 5 people interviewing a candidate. They haven’t thought about what they’re each going to focus on so they end up repeating and forcing the candidate to repeat some of the same answers, multiple discussions and the feedback is  “Did you like the person or not? Yes or no. You get maybe 1 or 2-sentence description. That’s a lot of hiring.”

That doesn’t work. I spend a lot of time on the process that I want to execute when I’m hiring somebody. I think about who’s going to join me in the process then we build the interview guide and we assign the sections with the questions of each person on the interviewing team, then we have a scoring sheet. I want everybody when they are done interviewing to score right then and there, and then I want a neutral party to collate all of those scores. The numbers don’t lie. You go with the person who ranks out at the top overall of that process, even if they’re not your favorite candidate. When I follow that process, I’m rarely let down by the result.

Certainly, a lot of that has come into play in the wake of a renewed increased focus on diversity, equity and inclusion because those processes like you described will help reduce unconscious bias, asking the same questions of all the candidates, having a regimented process and scoring, but that’s not a lot of hiring still. There’s clearly a lot of work to do that will help people make better highers because I think a lot of people feel like they don’t do a great job of hiring.

You think it’s something you’re good at if you’re good at talking to people, but we have terrible judgment about each other.

Hiring is something you think you're good at if you're good at talking to people, but we have terrible judgment about each other. Click To Tweet

It’s funny sometimes. I’m sure you have this with your spouse, friends, kids or whoever. Somebody will see something that you miss. They’ll have somebody pegged right one way or another that. Somebody else is completely blinded by some other aspect of that person and only discovers this attribute of them more slowly. It’s interesting how we all uniquely pick up on those cues, which goes back to like why you should form a panel of interviewers that’s pretty different.

There are two things I love to do in interviews. I love to ask people, “What’s a piece of work you’re super proud of? Could you share a version of that with us?” Sanitize it and take out proprietary information, but if you’re proud of a piece of work show it to me so I can judge something beyond how you answer questions in the interview then, I got a question in my interview process at LPL that I loved and I’m going to use which is, “What makes you interesting?” That’s a great way of getting to the total person and seeing what people are willing to share and how much of themselves are they going to invest in the job.

It’s a good question, a little bit of an indirect or a non-traditional one, but sometimes we’ll reveal things that you might otherwise get to. We talked a little bit about careers you’ve taken a bunch of steps in the course of yours. What are your thoughts on what people get right and wrong in managing their careers?

I can share what I’ve learned from my own mistakes. If you’re thinking your career is about getting to a certain level or getting a promotion, you’re typically not going to be set up for success. If you’re trying to construct a straight line, connect the dot from here to here, rarely do careers evolve that way. I don’t think they ever did. I think there are a few areas of very technical deep subject matter expertise where the line is pretty straight from point A to point B, the ladder to the top, but most careers are much more of like a rock climb where you even sometimes have to take not only step sideways but steps down to get to the better advantage point.

If you're thinking your career is about getting to a certain level or getting a promotion, you're typically not going to be set up for success. Click To Tweet

A lot of times people will come to me and what they’re asking for is, “How do I get to VP or director level?” I say like, “Why is that important to you? Is it because you want to make more money, have more responsibility or you want to manage a large team instead of a small team? Let’s pick away at why that title or that level on an org chart matters to you, then let’s think about how you get more of that which may or may not come with the title.” That’s where I see people tend to go down blind alleys when it comes to managing their careers. They’re pursuing something without understanding what they want and why they want it.

I feel like a lot of people don’t put the thought in time into it. I find it ironic given how much time we all spend working.

I tell people, “I don’t want you to have a big job. I want you to have a big life and figure out what work means in the picture of your life?” We always think about it in the context of checking a box on the level and the paycheck, but how do you think about it in terms of what work means to you in the scope of your total life and then what you’re going to go after because of that?

It is a good way to think about it. It’s thinking about the whole person or whole work and personal life in an integrated way. You must do a decent amount of mentoring whether formal or informal. I think we all get to the point in our careers where people look at us and say, “You’ve been around a while. What are you hearing from people? What are some of the topics that they most often come to you for help with?”

They almost always start with, “I want to get promoted. How do I do it?” What I have to disabuse people of or they’ll say, “You speak so well. You write so well. It must come naturally to you.” I have to disuse them of that notion quickly like, “I have to practice my skills and continue to invest in my skills all the time. Nothing comes naturally or easy to me.” The trick is making it look easy. It’s those two things, “How do I get promoted or how do I become good at X?”

There are two myths I feel like people have bought into that I try to evolve. One of them is you have to promote yourself and invest in yourself. You have to lead your own career. You have to promote yourself before anybody else is going to promote you. What I mean by that is if you want to manage money, you better go learn about it, read about it, try it out on your own with your own money, shadow people, use your vacation time to travel to invest your conferences and listen in. Buy your own ticket. You got to invest in yourself and promote yourself and be ready before anybody else is going to give it to you.

CSCL Amy Philbrook | Leadership First 90 Days

Amy Philbrook: You have to invest in yourself. You have to lead your own career. You have to promote yourself before anybody else is going to promote you.


People are often shocked that it takes that much work and time and energy. I ask people like, “How much money do you budget for your physical fitness? Do you budget the same amount for your career fitness? because you got to spend your own money.” The second thing is the idea that like, “Some people are naturally good at it. Very few people are naturally good at professional skills. Most of us have to work at it. What are you willing to do and how much are you going to continue to invest and be disciplined to stay good at something?”

Would you describe yourself as having a high degree of discipline?

I used to have a little bit less nowadays. Work has changed so much. I’m taking this call from the kitchen of an Airbnb and you know, my offices are scattered around the country. It’s harder for me to be disciplined in this much more flexible working model. Am I disciplined when it comes to focusing on my skills, keeping up my reading, staying abreast of my industry and asking for feedback? Yes. I’m disappointed in those things.

Those are the things, the reading and practicing. What other habits have helped you throughout your career?

Reading in my mind is the highest ROI impact activity I can get. I use my library card. I will not buy a book unless my local library can’t get it for me on time. It’s free. It’s an amazing benefit of living in this country and in this world. I spend a lot of time reading and I’m strategic about it. I’m reading a book on the history of Iran because I’m realizing much that’s influencing our lives both personally and professionally is happening in that part of the world. Iran seems to be at the Genesis of it and I have no context for understanding the history of that country versus what I’m seeing and perceiving.

I’m acclimating to my new role. I’m learning a lot there. I’m not reading a business book. I’m reading a book that’s going to give me context for understanding current events in the world, which are going to impact my business but in February and March 2024, I’m going to be reading the latest research on strategy and leadership development because I’m going to be putting some stakes in the ground at the end of my 90 days on areas of the business that I want to transform.

You can pick out the patterns of how your work is flowing and then you can be strategic about where you’re investing your time. The other thing I do is invest in coaches. I worked with an amazing coach. I hired her and paid for her myself because I knew I was going to be making some big career decisions and I knew I was likely going to be creating this sabbatical for myself. I didn’t have the courage to do it unaided so I hired a coach who I knew would challenge me with questions about who am I and what do I want. I invested a lot in that. I’m not going to be hiring a coach probably, but that will come back into the fold in 2025. I will set aside some capital and hire a personal coach, but I need to wait until I have clarity on what do I want to coached on.

You hit these points where it Ebbs and flows where you want that intense relationship with a working relationship with a coach because you’re going through some period of change or you’re stepping into a broader role or new job or whatever the case may be. There are other times you feel like, “I got this for a while. I can go a little bit on my own and then draw learnings, and then use that to take back to the next intensive period.”

Similar to you as well, I learned this later in life, not until my mid-40s. I need a physical challenge. I need to push my limits in a physical way. Every year I pick a domain that I’m not experienced at or I’m not performing at physically. What I’ve learned about myself is when I can learn how to push my physical limits, it automatically expands my mental limits. It was hiking, and I have a tremendous fear of heights.

CSCL Amy Philbrook | Leadership First 90 Days

Amy Philbrook: When I can learn how to push my physical limits, it automatically expands my mental limits.


I decided to take on some tough peaks and do a big endurance hiking challenge. It’s yoga. Yoga is a journey of discovery like, “What can you do? What does it feel like to do things that are very uncomfortable?” I wanted to get better at sitting in discomfort because I was taking this sabbatical. I wasn’t going to be working and it was going to be very uncomfortable. I find having a physical practice compliments the mental and leadership journey very very well. I wish I had discovered that sooner in my career.

For me, that’s always been a part of things. I mean I was doing triathlons when I was in my twenties, did a lot of cycling and then entertained the idea of going back to triathlons and that didn’t work out. I had started hiking and I’ve been doing the hiking, then I’ve come back to running over the last few years. It’s worked to fit in the runs, but I feel better. I have more energy throughout the day when I’ve gotten up and doing done around that morning, even though it’s meant especially this time of year going out of running in the dark and the cold.

There is definitely a bit of sacrifice. It’s not always like through on your T-shirt and your shorts and go out for running a nice 75-degree day, but it’s a challenge and even the focusing mechanism of signing myself for events. It helps keep me centered more generally than, in my case specific, to road race or whatever that I got coming up.

You learn so much about yourself, “Do I have what it takes to do it in the dark and the cold? Do I have that takes to hit the mat at the end of a long day when I’m already tired?” It’s making a promise to yourself and not breaking it, and that translates to leadership on a much bigger scale.

Many of us never completely figure out what we’re capable of, whether we do that in a physical, mental or whatever sense. You learn a lot about yourself from those experiences. You learn from your failures. You learn from places where you’ve mentioned earlier where you’re way out of your comfort zone and over time, it goes back to the lived experiences point you are making earlier. It’s like your worldview and your lived experience continue to expand your comfort zone the more that you push yourself into new things, whatever form it takes, yoga, hiking, running or whatever. It’s good to have those things. It gives you something to look forward to when you’re outside of work. The last question is if you had to go back and give advice to your 22-year-old fresh out of college self, what would you tell her?

I would tell her to lighten up. I would tell her that everything always works out in the end. The secret is to have a good relationship with yourself first. It took things seriously. I felt like there were a lot of check marks I had to put on the board. I had some big financial challenges starting out without any resources. I took everything seriously. Some might say, “That served you well. You were intense, but it accelerated your career.”

I missed out on a lot. I could have accomplished and be sitting where I am now, had a little bit more fun and been a little kinder to myself. What I try to tell everybody is, “It’s all going to be all right in the end. We’re people. We’re here on this planet to love each other and take care of each other. That starts with doing that for ourselves first.” It’s okay to laugh a little to lighten up. That’s what I would tell her. On my worst days, I’ve gotten in my own way because I’ve been taking myself too seriously.

We can definitely do that. Particularly, if you’re ambitious, if you want to make the most out of your professional life or life in general, you get very blinders on overly focused on things, sometimes at the expense of other things that matter or what matters to you you maybe haven’t discovered. It’s a good advice. Thanks for doing this. It was a great discussion.

I enjoyed it. Thank you for having me. Thank you for everything you’re doing with Pathwise. I turned to it as one of my go-to resources. I’ve picked up a lot of my reading through what you’ve published. I appreciate it.

Hopefully, the book summaries and some of the other things are useful. Thanks for that.

Take care and happy holidays.

Good luck with things.

I want to thank Amy for joining me to cover her new role, her broader career journey, her thoughts on leadership and careers and what’s helped make her successful. If you’d like to make the most of your career visit You can become a member. Basic membership is free. You can also sign up on the website for the newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram and TikTok. Thanks. Have a great day.


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About Amy Philbrook

CSCL Amy Philbrook | Leadership First 90 DaysAmy is Executive Vice President for Service with LPL Financial, a role she just recently started. She previously worked at Robin Hood in roles focused on Customer Care, Operations, and Learning and Development. And prior to that, she spent more than 25 years in a wide variety of roles at Fidelity Investments.

Amy is also a public speaker and thought leader, including for CNN, the Society of Human Resources Management, Bizwomen, and others. She lives and works in the Fort Worth, Texas area.


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