In this solo episode of the Not Another CEO Podcast, host David Politis explores imposter syndrome as an almost universal experience for founders and CEOs, regardless of company size or personal success. He opens with a personal story from his time at BetterCloud, where despite raising $180 million and leading a fast‑growing business, he questioned his competence and wondered if he deserved the trust of investors and executives. Politis defines imposter syndrome using a standard psychological definition and cites a TED talk by Atlassian co‑founder Michael Cannon‑Brookes to illustrate that even highly successful leaders feel like frauds. He frames the condition as having two possible outcomes: it can either paralyze decision‑making, erode confidence, and spread insecurity throughout a team, or it can become a catalyst that pushes leaders to improve, stay humble, and prove their worth. Drawing on a Buddhist monk’s teaching that thoughts are neutral until we assign meaning, he argues that the way we interpret imposter feelings determines their impact. He then offers concrete strategies: treat the feeling as a growth signal, use it to identify skill gaps, focus on areas where you are or become an expert, maintain humility while staying hungry, solicit feedback, and cultivate a healthy dose of paranoia that drives preparation without tipping into destructive anxiety. Politis warns against over‑compensation that leads to ego inflation, and he shares anecdotes of top performers who also experienced imposter syndrome, showing that the feeling can coexist with high performance. The episode concludes with a call to listeners to share the episode with anyone wrestling with self‑doubt and an invitation to reach out with thoughts or questions.
Chapters
Imposter syndrome either crushes you or it drives you. As the stakes get higher, the imposter syndrome intensifies. When you really let that imposter syndrome win, you end up in a place where you, you've lost trust in your own intuition. Welcome to Not Another CEO Podcast. I'm your host, David Politis. Every week we talk to inspiring leaders and get the true stories and the ups and downs, the lessons learned and come away with actionable advice for our own journeys. Hello everyone. Welcome to our February Pulse episode. The topic I want to talk about today is imposter Syndrome. I've spent the last couple of years meeting with and interviewing literally hundreds of founders and CEOs one on one. And when I sit down with them, many of them open up about struggling with imposter syndrome. This is first time founders who are chasing product market fit, who feel it, and serial CEOs running companies doing hundreds of millions of revenue, who feel it. Success, age, experience, really doesn't matter. This is something honestly that I have gone through, that I still feel today. I mean, at Better Cloud, there was a point we had raised over $180 million, had over 300 employees, had this amazing executive team, 2,000 customers, crazy revenue growth. And I remember thinking to myself, am I equipped to run this kind of a company? Do I deserve to get this kind of trust and this much money from all these literally top tier invest. Why are these experienced executives wanting to come work for me? Am I delivering what these customers actually need? And yeah, there were, of course there were days that I was confident about what I was doing. But then there were days where I really did question it. And what I've learned from all of those conversations and from my own experience is that imposter syndrome really doesn't go away. And the chances that you experience it, not even just as a founder CEO, but, but as, as a leader, are close to 100%. And it's more about the question of how you choose to deal with that. That's, that's what makes the difference. My view is imposter syndrome either crushes you or it drives you. If it crushes you, it slows down your decision making. It paralyzes you, you know, and it could, if you let it drive you, it'll push you to get better, to overachieve, to, to prove that you deserve the position that you're in. So I, I want to talk a little bit more about what I've seen and, and some recommendation that I have. So I went and I, I looked up Imposter syndrome in the dictionary. And the definition is imposter syndrome is a psychological condition that is characterized by persistent doubt concerning one's abilities or accomplishments, accompanied by the fear of being exposed as a fraud despite evidence of one's ongoing success. And this is something that literally every, I mean definitely every, I think most founders, CEOs deal with this. If you have any self awareness, you probably are going to experience imposter syndrome. And there of course is some spectrum, but I think that, that especially the high achievers, they experience it to some degree. And to think like this is something that we're going to get past, I don't think that's true. Many people think like, oh, I'm going to hit this revenue milestone, I'm going to, I'm going to raise this money, I'm going to. And then this self doubt will disappear. It doesn't actually. I think as the stakes get higher, the imposter syndrome intensifies. There's a TED talk with Michael Cannon Brooks, who's the co founder and CEO of Atlassian. And the exact quote he says, most days I feel like I often don't know what I'm doing. This is a person running maybe one of the most successful software companies of all time and he's talking about feeling like he doesn't know what he's doing. So really it doesn't matter what you've accomplished. These feelings, they don't go away. And like if you keep growing and the business keeps growing, then you're going to constantly be stepping into roles and making decisions that you've never made before. So again, my view of this is that there are two paths forward when it comes to imposter syndrome. Path number one is that you can let it paralyze you. This is really where imposter syndrome becomes your enemy. It slows you down, it makes you second guess everything. I've seen this with people who have really good businesses and who have navigated their businesses to, to, to good scale with great investors, great customers and they start questioning their gut instincts. They assume that somebody knows better. They tell me, oh, it's, you know, this investor. They must know the answer because they have access to billions in capital. This CRO must know better because they have 30 years of experience. This customer knows better because they're an executive, have been in the, in that role for a long time and they're at some huge company. And so when you really let that imposter syndrome win, you end up in a place where you've lost trust in your own intuition, you think there's no chance that your gut feeling is right. You start feeling like you're getting away with something, like someone's going to find out that you don't know what you're doing. And so to be going down this path, this really slows you down and, and makes you spend too much time thinking about what others think. You start avoiding taking risks because of, you're scared of whatever the consequences are going to be. And, and it's maybe the worst part is that the insecurity creates this ripple effect. And now your team, the broader company, your investors, the customers, they start feeling less confident and they don't really feel like following you or, you know, because they can feel that. And the other option on this road of, of when you, when you're feeling that is to let it fuel you. This is, I think, where imposter syndrome becomes your competitive advantage. You, you don't let it paralyze you. You again, you, you let it drive you. You know, we, I recently took a trip with my family. We were in, we were in Thailand and we were. One of the things we did, we, we sat with a Buddhist monk in Chiang Mai, Thailand, and something he said really stuck with me. He's, he said this, this Buddhist philosophy of thoughts themselves are neutral. They're not inherently good or bad. It's only when we assign them meaning that they take on that value. And so as I was preparing to do this, I was thinking to myself, imposter syndrome kind of falls into that. You, it's a thought. You have this feeling at a moment in time and the question is, what value do you put, put on it? And I make the point today, I'm trying to make the point to all of you that I think that the best people take this feeling of imposter syndrome and then use it to push themselves to get better, to prove without a shadow of the doubt that they deserve the position that they're in. And now I do want to say this is important. I have seen people overcompensate and I've seen CEOs who basically because of this feeling and because of show, they need to show strength, they almost become too egotistical, too confident. And it's like this weird dynamic because they're so self conscious, they're overcompensating for, for, for that, with this overconfidence, real heavy ego. That's not good either. So like, to me, I think when, when, when you channel that imposter syndrome correctly, properly, it actually lowers your Ego makes you a better listener, a more grounded leader, but at the same time drives you, drives you to prove that you deserve that seat. And so here just some ideas as you're. If you're going through this again, which statistically the chances are that you are, is how do you deal with it? So, firstly, I would recognize this, this feeling you have as a signal that you're growing. It means that you're stepping into something new. Something feels uncomfortable, probably because you haven't done it before. But it's not evidence that you're failing. It's evidence that you're pushing beyond what you already know how to do. And also is a big one. It's evidence that you care, that you give a shit and it matters to you that you're successful and you don't want to disappoint others. The other thing is, I think it can really identify the skill gap that you need to fill when you're feeling this, when you have that imposter syndrome hit, you ask yourself, what am I feeling unprepared for? What skill or gap this exposing in. In my knowledge, in whatever. And I, I've had this myself. Actually. For me, a big thing I speak very publicly about it is how bad I was at public speaking, how uncomfortable I was, how bad I was, how uncomfortable it made me. And when I really dissected it, because it started getting really bad, like truly paralyzing. And when I really dissected, I realized that I always felt like the audience knew more than me on a specific topic or that they would think that my points were stupid or they were questioning me. And it really forced me to say, okay, how do I get better at public speaking? I have to deal with that imposter syndrome. How do I deal with that imposter syndrome? I need to make sure that whatever topic I speak on, it is. I am an expert in that topic, like truly an expert. And so now whenever I present, I make sure that I am only presenting on topics that I'm an expert on or that I'm becoming an expert on before I speak on it. So that when I get on stage, I know and I think it. Honestly, I think it's made me more, much better as a speaker. The other thing is it I, I believe that again, like I said before, that imposter syndrome can keep you humble. Humble yet hungry. Humble and wanting to continue to learn. The, the best CEOs are vulnerable. They're asking for feedback. What am I doing well? What am I not doing well? They're. They're they're never really satisfied with their own growth. They're leading from the front, showing their team the growth mindset. And I, I think that when you use this the right way, you say, okay, this is a moment of time for me to, to understand for my team their ideas where again, where they think I can get better, what they need my help with and change the, the, the dynamic of how you feel around this imposter syndrome. And then the last is, lets you create paranoia. And you could say the paranoia is not good, but I think in this case you can have healthy paranoia driven by imposter syndrome. So I, I always think about, in my entire career, 20 plus years of running companies, my best people, my best best. I'm talking about the top 2%, 5% of my people, many of them had imposter syndrome. And I know this because I would call them into my office to talk about an initiative, share an idea, because they were one of my best people. And they would come into the office and the first question they would ask me is, are you firing me? I said, are you, Am I firing. Why would I be firing you? You're like the, you're literally the best person at the company. And they say, oh, but you're calling me for this meeting one on one. I thought that, you know, you were going to fire me. And I've actually, I've had that feeling at points with the various boards that I've worked for, and I feel like I'm going to walk into the boardroom and I'm going to get fired. Now is the reality that they wanted to fire me? No. But that imposter syndrome drove that paranoia. And I actually think that that could be really healthy. Not, not to the extreme, but it can drive you to overachieve, to prove the, that you, you like, that you earn that seat at the table. So with all of that being said, imposter syndrome isn't going to go away. You're going to feel it now, tomorrow, next month, when you raise the next round, when you hit the next revenue milestone. It doesn't matter. Like, you're going to continue to feel it. And it's just a question of what do you do with that feeling. Do you let it freeze you up or do you let it drive you forward? And I, I really believe that channeling this for good is an opportunity for all of us and a good reminder for all of us. So I really hope this is helpful to you or someone you know that's been dealing with this. If it is please share with them. And really, as always, if you have ideas, thoughts, comments on this questions, feel free to reach out and we'll see you for the next episode of Not Another CEO Podcast. That's a wrap for this week's episode of Not Another CEO Podcast. Thanks for joining. For show notes and more, please Visit not another CEOPodcast.com we'll see you next week.
