Overcoming Imposter Syndrome With Andrea Fryrear

Jan 25, 2023

Every first-time CEO is going to have imposter syndrome at first. Join Andrea Fryrear, the CEO of AgileSherpas, as she talks about how she dealt with the imposter syndrome of being a first-time CEO.




I am so excited to introduce you to our guest. I’m sitting face-to-face, in person, with my friend, Andrea Fryrear. How she came to become my friend is an interesting backstory. Her company at the time hired my company to coach every one of their employees and give them a gift of basically a career development plan. I got the chance to hear this amazing woman’s story back in those days.

She had this idea for a marketing agency that would be based on Agile principles. I heard a lot of people’s ideas, and I fell in love with this idea. At the time, I said to her, “I think you need to start a business.” Here we are now, and look at what she’s done. She started a business, and she’s been rocking it. We get a chance to hear her story of how she turned the corner and created an incredible environment for people to thrive. Andrea Fryrear, welcome to the show.

Thanks for having me.

Let’s talk about AgileSherpas. That’s the name of your business. Tell us a little about your start as a solopreneur and how you have grown it now to the number of employees you have and everything.

It was an idea at first that I discovered Agile because I was doing marketing at a software company. I saw how much better off our development team who were using Agile was compared to our marketers, who were always behind. We could never quite stay on top of things. It was always fire after fire. I convinced my boss at the time to let us try using Agile to run our marketing processes.

It was so much better. Everyone was happier. We were more productive. After that, I couldn’t shut up about it. I thought everybody needed to know about this. I was writing and speaking about it. Lots of people kept reaching out to me and saying, “That’s really cool. Could you help my marketing team do the same thing?”

Overcoming Imposter Syndrome With Andrea Fryrear Click To Tweet

Eventually, I thought I could actually do this as my full-time job, and that’s around the time that you and I met. It was such a good validation for somebody to go, “You’re temperamentally suited to this, and this is a good idea.” I had never thought of myself as an entrepreneur. Even for the first couple of years of AgileSherpas, it was myself and my cofounder.

I went out and helped clients. He stayed behind the scenes, running operations. I thought that would be what we did forever. If I could make a decent salary at that, I would call it a win. It turned out we were super onto something and couldn’t keep up with the demand for what we had. We had since gone from the 2 of us to now 22 full-time employees since 2017 when we started. I went from a full-time consultant to a full-time CEO who’s running a company. It’s been crazy years.

I love hearing that story. Let’s talk a little bit about how it’s been going from being an employee to being a solopreneur to growing this team. What have you noticed in yourself that’s had to shift over the years?

It’s been a real need to be committed to learning all the time. It feels like every week, month, or quarter, there’s some other thing that I need to knuckle down and understand better. Not master it because I feel like I’ve got years to go before any of this is mastered, but to at least be able to implement things and put things in place that will support me and the team.

As soon as we got those first couple full-time employees, it was a total shift in how I thought about things because now these people rely on AgileSherpas for their livelihood and career development. My Cofounder’s name is Peter. When it was Peter and I, if we messed it up, we’d both go back to our corporate marketing careers. No harm, no foul. We gave it a good try. Now, there are dozens of people that need us. It’s been ratcheting up in pressure, but also, every day is exciting, and there’s always something new to learn. It’s been a completely different trajectory than I thought I was on, but amazing all the time.

I’ve noticed that people who go from being the worker to being the leader sometimes struggle a little bit with delegating and shifting from knowing that it’s not going to be done exactly the way you would’ve done it. How was that emotional transition for you?

It’s been tough at times. We brought on a lead trainer ahead of training. He’s about to celebrate his two-year anniversary, so in 2021, he started. He stepped in and took over all the client-facing activity. That was difficult because that was me. That was what I did, and that was my baby. All of the presentations and workshops were things I made up and put in place. To hand them over to someone was challenging.

He was our second full-time hire. Both of our first hires were brilliant, dedicated and excited about Agile, just as excited as I was. That was the only thing that made it possible for me to delegate and hand things over. It was to know that it might not be exactly the way I would do it, but 9 times out of 10, it was better than what I would’ve been able to do.

I was trying to run a business, so it was still like everything was 10% of my time. When somebody could come in and make it 100% of their time, they made it so much better. Now, that team has fifteen employees, and he loves all of them and gives them the attention that I couldn’t do. Seeing that happen with him early on has made it easier to hand off function after function, to step away, and to hire very carefully to know that that person is going to be able to do it better than I would’ve been able to do it.

You bring up a key point that we haven’t talked too much about on the show in the past. In addition to hiring people against your values, which is something I’ve talked a lot about, you also want to hire against the why. In your case, the why was this different way of doing marketing, doing it through the model of Agile. That’s totally unique. It’s a completely different way of doing marketing. That’s basically what this guy had. He not only was capable but he was bought into the mission, in the why.

Absolutely. I can be confident that he’s going to make choices based on our values. Even if the actual implementation might be 5 or 10 degrees off from what I would’ve done, it’s still going to be in keeping with our core mission and values. That will ultimately make it all work together.

With that growth, too, I suspect you probably have also had times where you’ve felt like, “Now, I have 22 employees.” If you don’t mind sharing, what are some of the head crash that’s come up for you? We all have it.

There have definitely been Imposter syndrome kinds of moments where I’m a first-time CEO and a first-time founder. There’s a little bit of, “What do I know about this? What right do I have to bring these people on and tie their livelihood to my crazy brain?” I’ve had a CEO coach from the moment that I stepped formally into that role.

I wasn’t a CEO at first. That wasn’t my title for several years because there weren’t employees. It felt silly to call yourself a CEO when it was just two of us. Once we started making hires, it was clear that somebody had to steer the ship. From the moment I stepped into that, I’ve had a coach, which has been so important to have somebody I can be open with, who’s outside the business and gives me that perspective.

It’s the Imposter syndrome and the idea that I don’t know what I don’t know. For sure, I’ve made mistakes. Having people around me, too, who are rooting for me and want me to succeed has helped with that a ton. There’s this sense of fear of always, “I’m about to make a big mistake because I’ve never done this before.” The coaching, I read all the time. I have workshops, retreats, and things like that. You have to.

It’s hard to make time for that, especially when we’re growing so fast. There have been so many things that I’ve been like, “I was going to mess that up, but now I’ve learned a better way to do it,” and not being afraid to say, “No. We’re changing that. We’re going to do it differently now.” To have people who are behind me saying, “We trust you to make that decision,” helps quiet the Imposter syndrome voice.

Imposter Syndrome: As a first-time CEO, there will be times when you think you’re going to mess up, but you just have to learn. Don’t be afraid to say “I’m changing that” or “We’re going to do that differently now.”


It’s amazing how the leaders that I see have a coach or some support group around them are the ones that do tend to miss some of those rough turns. Others who don’t take it on and think that they can figure it out all themselves are the ones that later on fail consistently over and over. It’s so important to commit to that growth.

There’s a piece of us that feels like we should know it, but none of us do. Reading a bunch of books doesn’t help either because you get a little bit of an idea over here and a little bit of an idea over here, but you don’t know if that stuff worked. If you have someone sitting side by side with you as a coach who’s maybe run a business in the past, they can say, “I tried it this way, and then this was the better benefit or the better outcome.”

Also, seeking out communities of other entrepreneurs, too. I joined EO, the Entrepreneurs’ Organization, a few years ago, and that’s been transformative as well. You have people around you who have either made this mistake already. They can be like, “Look out. Iceberg ahead,” or are struggling at the same time with you, and you can bounce ideas off of people.

You instantly get exponential growth in the number of ideas you have access to for people who have already been successful or are trying to grapple with the same things you are. That’s been great as well. It’s an investment of time, money, and intellectual energy to be a good member of that community that will ultimately lead to those outcomes. It doesn’t just happen because you wrote the membership check.

No. You have to be involved. You do get out what you put into those things. I’m a member of a couple of communities, too. I don’t know how I would’ve survived the last several years without them. It’s very important. Getting a coach and surrounding yourself with a community have been two things. Anything else you want to add to that formula?

A lot of self-reflection is important. I’m a big journaler. I think well on my own and taking the time to work through, “What is going on? What do I want? Why am I trying to do all of this?” It’s easy to get caught in the trap of, “We grew 89% year over year. Let’s do it again. Let’s hire twenty more people.” To pause and say, “Why? Is that actually going to help us help more people?” Maybe it will, but will it not be that much better?

Overcoming Imposter Syndrome With Andrea Fryrear Click To Tweet

It’s avoiding that kind of growth for growth’s own sake and knowing what you want as a founder and CEO. Bringing on more people and making more money is expected at a certain point and figure out, “Is that actually what you want?” If yes, great. How are you going to do that? Maybe no. Maybe there’s a point at which you’re happy to put it into cruise control, let it be an amazing business, and have everybody love to work there. I don’t know the answer to all of those ones yet. To take the time to reflect is the other.

One of the most helpful pieces of advice I had when I first opened up my business was somebody saying to me, “You can make it as big as you want to make it.” If you want to make it and it’s just three of you, there’s nothing wrong with that. If you want to make it where there are hundreds or thousands of people, then you can do that, too. You can make it whatever you want. Some of the joy and freedom of being an entrepreneur is getting to make those choices. Rapid growth does have some major consequences. You’ve probably experienced a little bit of that. What has happened? What’s been some of the bumps in the road along the way as you’ve added people?

We’re getting to the point where I’m realizing some of the, “What got you here won’t get you there” moments. That could be tools, processes, or people that were great for the moment we were in but, for whatever reason, are not the right fit for moving ahead. Those have been hard. Ripping out a tool and putting in a new one is challenging.

Imposter Syndrome: As an entrepreneur, there will be “what got you here won’t get you there” moments. There’ll be some tools, processes, or people that can be great for the moment but will not be the right fit moving ahead.


Having a conversation with someone to say, “It’s been great, but we’re going in a different direction,” sucks, but ultimately was what’s needed for the business to keep going and keep growing and to make it a great place for the employees to work. A bad process, a bad tool, or a mismatched person has this much bigger impact and ripple effect now. Be diligent about monitoring those things and then making choices where they have to be made.

The people part of that is almost sometimes a little bit easier to understand. Where with the tools and systems, we’ve just ended up with technology proliferation. You bring a tool in that you think is going to serve you, and then you get entrenched in it. You’re like, “That didn’t actually help with the growth, and now I have to add another tool,” and you get another tool. It’s such a pain. With the people side, it’s just heartbreaking when you’ve had a hire that wasn’t a fit, and you have to let them go.

Before I started the business, I was an individual contributor with maybe 1 or 2 direct reports. I never had to fire anyone. The first time going through that was the worst. I feel a little bit like it’s a rite of passage. Not that it’s ever going to be easy, but now I can do that when I have to. I did not die. Nothing catastrophic happened from it. It’s getting to know how to run a P&L and understand your numbers and stuff. It sucks for a little while because your brain doesn’t like it. It’s not the way that my brain traditionally worked, but now I have a lot of confidence in it. It’s more of that growth.

My experience now has been that it is so much better to fire fast when you realize you’ve got somebody who is not a fit instead of hanging onto them and hoping it’s going to continue to work. Did you find yourself in that circle or that situation at the beginning?

Definitely. When I started realizing this would have to happen, I started listening to a bunch of podcasts and reading about it because I’d never done this and felt the need to educate myself. Here is one of the ones I heard, I can’t remember which exact source it came from. They said, “By the time you as a senior leader are aware of this issue, everyone around you has known for months that this is a big problem.” I was like, “That’s so true.”

Overcoming Imposter Syndrome With Andrea Fryrear Click To Tweet

What triggered it for me was people starting to come to me and say, “This is a problem.” By the time they’re doing that, they’ve been struggling for months before they’re willing to bring it to you as a senior leader. It was definitely beyond time by the time it happened, but I’ve never talked to anyone who was like, “I got right out in front of it,” the day that I knew it needed to happen.

It’s one of those tough lessons. What are other things you feel in the early days you don’t do anymore because you’ve turned the corner on it?

A good example is we went to market with two new course offerings. In the olden times, I’d have been the one looking at slides, mapping them to learning objectives, and making sure that those courses were on point and totally perfect. I did not touch them. The team took them over. Our most recent one is Business Agility Foundations, which we abbreviate as BAF.

We ended up even with a hashtag across all of our Slacks. It was like #BAF because everyone was talking about it all the time. I have never looked at that deck. That workshop deck, it’s been delivered. We got amazing feedback from the client on it. I’ve never seen it. The team took it, ran with it, and did an amazing job. It was professionally designed slideware. We passed the accreditation. They’re doing it all faster and better than I would’ve done.

It’s getting out of the way and letting them run with it. That takes a pretty strong leader to do that, especially a leader and founder.

The team is amazing. They’re smarter and better than me at what they do. It makes it easier to get out of their way.

If you were to onboard a brand new employee and they were to say, “What’s your job, Andrea?” how do you describe what you do for AgileSherpas?

I’m very much stepping into more of the visionary role, where it’s my job to try to see over the hill and understand what the future of the company is going to look like and to make sure that we are headed in that direction, staffed appropriately, processed appropriately, and equipped to get there. That looks like strategic thinking, looking at the market more, understanding the competitive landscape, talking to customers about what they are missing from us and what they wish we had that we don’t have. I spend a lot more time looking at spreadsheets these days, forecasting. We’re projecting this level of profit for the next quarter. How are we going to reinvest that money? What are we going to need to do to attract more talent? It’s looking at the business more broadly. Whereas I used to be down deep in the trenches of different things day-to-day. I’ve slowly ratcheted myself up over time.

Are you having fun?

I’m having a great time. I got burned out over the summer. Five years, I grow all the time. I traveled so much before COVID. 60% to 70% of the year, I was on the road, and so I really hit a wall. I took a month off. Did not open my computer and was like, “I don’t know if I can do this. I don’t know if I’ve got it in me to do another five years.” I took a month off, and it was transformative. Since I’ve come back, it’s been fun again, “I’m ready to go. What else is out there? What else are we doing?” I’m excited again instead of, “I can’t believe I have to have another conversation like this. I have to do this again.” It’s been an inflection point for me.

I didn’t think about it at the time. I knew I needed to do it. When I came back, everybody was so appreciative that I took that time away when I needed it because they felt like it gave them permission to take time when needed. We had a couple of people get married. They’re like, “I’m going to take two weeks from our wedding because I feel like I can,” because that behavior was modeled. I never even thought of that as a potential benefit, but it turned out to be a great side effect.

What do you think was the biggest realization for you? What switched for you in that month?

It was back to what do I want out of being an entrepreneur. I can’t go back. I’m totally unemployable at this point, and I can only work for myself going forward. It was, “Do I want to keep working for myself in the same way?” At this point, I feel like every client has the same questions, issues, and concerns. When I get in the weeds with clients, it feels like Groundhog Day, where it’s the same over and over again. The great thing about having a team now who’s primarily responsible for that is that’s their core skillset set, and they’re excited to help clients all day, every day, whereas I had done it too long.

Realizing that I can’t get pulled back down into day-to-day client stuff and that I have to work hard not to do that was my main takeaway. It feels guilty when you started as a builder and a doer in the early days, it feels like I’m neglecting my child or something, but it works better when I can look out and be that strategic leader because if I’m not doing it, no one’s doing it. That’s a real danger for the business.

Imposter Syndrome: As a CEO, know that you can’t get pulled back down into the day-to-day things. The business will work better if you can be that strategic leader because if you’re not doing it, no one is.


If I were to map your journey as an entrepreneur, you started as a solopreneur, and you started building this business up. Over time you’ve learned that more people can come onto the team and do the work even better than you, it’s allowed you to open up your mind to more of the strategic side, which is so critical for growth and for scaling.

If you don’t create that space to think and be strategic, you’re always in the weeds. It’s impossible to grow because you’re holding the reins back instead of letting that horse gallop. That’s neat that you were able to do that and take that time. On that note, it seems like a great place to potentially stop here. I want to thank you again for meeting me here. We are at Kiln in Boulder. Fantastic spot. Andrea Fryrear, we’ll check in with you again in a couple of months and see how you’re doing. Thank you again.

Great to be here. Thanks.


Important Links


About Andrea Fryrear

Andrea Fryrear is CEO and co-founder of AgileSherpas. She specializes in organizational design and executive coaching, but now spends most of her time focused on the vision, culture, and strategy of AgileSherpas.

Prior to co-founding AgileSherpas, Andrea spent over a decade in marketing. Her roles included content strategist, content marketer, project manager, and editorial assistant for both brands and agencies. Once she discovered Agile ways of working, however, she dove in and has never looked back.

Andrea is one of the co-authors of the ICAgile Marketing Agility curriculum, as well as two books on marketing agility: Mastering Marketing Agility and Death of a Marketer. She holds numerous Agile certifications, including Certified Agile Leader (CAL-1), Certified Professional in Leading with Agility (ICP-LEA), Certified Agile Coach (ICP-ACC), Advanced Product Owner (A-CSPO), Scrum@Scale Practitioner, Certified Professional in Marketing Agility (ICP-MKG), ICAgile Certified Instructor, and Certified Scrum Master (CSM).

Her non-Agile achievements include a Bachelor’s degree in English from Austin College and a Master’s degree in Women’s Studies from Oxford University.

Although once referred to as “The Beyonce of Agile Marketing,” Andrea does spend time away from her kanban board occasionally. Her favorite pastimes are camping, skiing, and hiking in her adopted Colorado home, ideally followed by a local microbrew and a British mystery novel.