Tyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here?

Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company under various titles, most recently CEO. I left in October. So it's been about nine months now.

Rick: One of the big reflections I had was sometimes how I treated people. Sometimes I was super impatient with people and put certain immediate business goals over really trying to make people feel good about what we were doing or where we were going. And I regret those moments because it was so short sighted, right? And so, as I look back and analyze why did I do that? I think a lot of those situations where fear-based. I was scared of missing a short-term goal, or I was scared of what I want to talk to you today about. Feeling like I might be found out as a fraud, as a CEO. And so I want to talk to you about this because I wonder if you ever feel this way? I guess impostor syndrome could be defined as a fear of being found out as a fraud. But I would go a step further and say, do you ever feel like a fraud in your job or catch yourself making decisions not based on what's right but out of fear?

Tyler: Yeah, I mean, okay. So I definitely feel like a fraud all the time. I'm of the opinion that the only people who aren't are sociopaths. Everyone I've ever talked to no matter how accomplished they are, everyone's like, “Oh, I don't belong here. Everyone's smarter than me,” and all that. I definitely feel that way just constantly, yeah. It's surprising to me to hear that you did so much.

Rick: Oh, yeah. Constantly. And I think it caused me to work a lot more than I needed to. That's the fear of failure. It caused me to stress and worry about things that were outside of my control unproductively, and I think it caused me in certain situations to make the wrong decision.

Tyler: Interesting. Yeah. Well, so the reason I was surprised to hear that is because on the surface maybe more than anyone I've ever met you seem like the classic CEO type.

Rick: Are you calling me a sociopath?

Tyler: No, no. What I mean is you're type A personality. Do you agree with that?

Rick: Define a type A personality?

Tyler: Like you... Well, yeah, maybe I don't have the best definition. But I interpret that to mean like, you aren't afraid of conflict. You kind of say what you mean. You're just kind of a person who's in control and likes being in control. And maybe this was me just not seeing what's beneath the surface, but you work really hard. You read a million books, you network, you make connections. To be honest, half my impostor syndrome comes from looking at you and being like, oh, no, that's what a CEO looks like. I'm not doing any of that stuff.

Fear-based decisions and regret

Rick: The interesting thing to me isn't to discuss whether people feel this way because I think everyone does. I think what's scary is... I think what I reflected on was not necessarily that I had this, it's how I dealt with it.

Tyler: Okay.

Rick: And so, I think that, let's assume for purposes of this part of the conversation that everyone has some feelings of impostor syndrome or being fraud. And that's a fear thing. What I think in certain situations I did was, let that dominate my emotions. And that could have resulted in me not being thoughtful about how I was communicating with someone in a moment, or making a decision that was fear-based versus opportunistic. I hypothesize that a lot of decisions leaders make, they make out of fear and maybe those are the decisions that they regret the most. Does that resonate with you?

Tyler: Yeah. I think I have a very different reaction to it than you do. I think that using kind of generic words like fear and regretting a decision, I think those still apply, but like, it takes a very different form for me. But yeah, definitely. I'm trying to think of the worst decisions that I've made.

Tyler: The number one worst one was certainly made out of fear, although I'm not sure it's a fear that was rooted in feeling like an impostor. And that was that I had an employee that I needed to fire. It was obvious to me that I did but I was just like, oh, I'll make it work, this or that. And I just waited for him to quit and he did eventually, thankfully, because it could have dragged on forever. But that's by far when I look back at myself as a leader. That's my weakest moment ever. It was fear-based. I don't think it was impostor syndrome based for me.

Rick: What was the fear?

Tyler: Well, first of all, I just hate confrontation. I guess this is maybe a little different from impostor syndrome. Part of it is that I took a big risk hiring him and I convinced him to take a big risk accepting the offer. And you're admitting you failed is one of the things. Now, I'm normally not too afraid of failure, but when it's really impacting another person's livelihood or something like that, the pressure is really high. And I think I was just afraid to say, I'm putting an end to this. I don't know.

Tyler: I've definitely had other moments though, where... The thing is, I think my reaction to impostor syndrome is to remove all of the things that I feel unconfident about. And so it's less. I think maybe it sounds like you were saying you kind of lash out almost. I do the opposite. I withdraw and say, "Oh, well. I don't think I'm good enough of a leader to do this thing. I'm just not going to do it." The company doesn't do that. That's not in our core competency.

Rick: Interesting. So yeah, maybe it kind of gets into fight or flight.

Tyler: Mm-hmm (affirmative).

Rick: I have a fight response, while you have a flight response.

Tyler: Yeah, when you were talking I was thinking exactly that. You're one of those animals that gets real violent when they're backed into a corner.

Rick: Yeah, when I've been under the anesthesia for surgeries before, and I had to learn this, I always forget because I don't get surgeries very often, but I do know this now. Before I go under, I have to tell them when they bring me out of the anesthesia they have to tie me down because…

Tyler: Wow.

Rick: ... I come out and I come out swinging. Which isn't great when you're getting a shoulder surgery.

Tyler: Yeah, seriously. Wow. I didn't even know that was a thing. But yeah, I mean, I don't want to...

Rick: You probably come out going boohoohoo!

Tyler: Yeah, probably crying about something awkward I did in third grade. But yeah, okay. So I think we're saying we experience the same things, but we have very different reactions to them.

Rick: Yeah, but do you regret that reaction? I guess, do you feel like you're missing out on... Are you fleeing from something and making decisions for the company that are fear-based, flight-based that aren't the right decisions?

Tyler: This may be taking...

Neil Atkinson, "Transformer: Klopp, the Revolution of a Club and Culture" (Canongate, 2024)