From Self-Doubt to Success: The Mindset Shift Every Leader Needs

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Nathan Tanner: I found when it comes to internal stories, it's very important for us to not say, okay, like I'm just not good at this or, AI is a hot topic right now. I just can't learn AI or I can't do this. The reframe of, okay, I'm not good at this yet, or I haven't learned how to do this yet, creates room for possibility and getting in front of that internal story becomes really important.

David Rice: Welcome to the People Managing People podcast. We're on a mission to build a better world at work and to help you create happy, healthy and productive workplaces. I'm your host, David Rice.

My guest today is Nathan Tanner. He is a former HR leader at DoorDash, Neighbor and LinkedIn, and the author of "The Unconquerable Leader". We're going to be talking about overcoming internal challenges of leadership and putting imposter syndrome in the rear view mirror.

Nathan, welcome. 

Nathan Tanner: Good to be here. Thank you so much. 

David Rice: Awesome. You've worked at some pretty high profile companies, DoorDash being one of them. And I've heard you know on some other shows that you've done, that you started at DoorDash.

It was worth like 600 million. And by the time you left, it was worth 71 billion. And how chaotic that was at times. Take us through that experience. I'm curious, how much was imposter syndrome an issue for you in that role? 

Nathan Tanner: Yeah, absolutely. I joined DoorDash in late 2016 and I was at LinkedIn where I was an HRBP.

There were about 250 employees at the time. And I'd been telling myself for a long time, like I want to get into a startup. Like I want more responsibility, more impact, all those things. And Oh my goodness. DoorDash was be careful what you wish for moment. It was a rude awakening jumping into that environment.

DoorDash had raised a lot of capital at that point, but certainly, far from profitability, Uber Eats was coming into the space. Grubhub was a large player. And it was a very high stakes, high pressure environment. It was an incredible opportunity and a big challenge for me because I was doing so many things that I hadn't done before.

And imposter syndrome hit really hard. I remember the first three or so months at the company waking up with a pain in my stomach almost every single morning. A couple weeks in, I remember talking to my dad about this and telling him like, Hey, I think I made a bad decision. And he was like can you go back to LinkedIn?

I'm like, no, that opportunity is sailed. And I was like it just sounds like you just got to figure it out. And the boats were burned. I had to figure it out and it was a huge challenge. But one thing that was fun is after I got through those first three or four months, I started gaining some more confidence and started developing those skills that were needed to be successful.

And I found that I really liked that fast pace, high pressure environment. And so I think we all face imposter syndrome and sometimes we may question whether or not we can do it. And sometimes like just putting our heads down and figuring out and moving forward and fighting through that imposter syndrome is how we build confidence.

David Rice: That's interesting. Cause you were talking about like the high pressure, fast paced environment. And I think like the pace of change is something that I feel cripples a lot of people because it's like, it's not even just keeping up with changes in the workplace, right? There's like the chaos of the world, the developments that sort of naturally take place in our own lives.

It feels like I can't keep a grip on any of this. It's that sort of insecurity breeds insecurity, right? I'm curious, how much do you think that sort of fuels imposter syndrome and breeds negativity in the internal story that we tell ourselves? 

Nathan Tanner: It absolutely can if we let it. And I love that you touched on that internal story that we do tell ourselves, because that's really big.

I found when it comes to internal stories, it's very important for us to not say, okay I'm just not good at this. Or, AI is a hot topic right now. I just can't learn AI, or I can't do this. The reframe of, okay, I'm not good at this yet, or I haven't learned how to do this yet, creates room for possibility. And getting in front of that internal story becomes really important. 

David Rice: Yeah, no, I think you hit the nail on the head there. When it comes to that internal story, take me through some of the key elements of keeping it focused on growth. Showing yourself a bit of grace, too, because I think that's a key aspect of that internal story is to keep it positive and to ultimately have it be a productive story.

Nathan Tanner: Yeah, we need to be very careful about the stories that we do tell ourselves. I love this quote from Paul Graham, who's the founder of Y Combinator. He says, the more labels you have for yourself, the dumber they make you. And first off, pausing and be like, okay, what are the labels that I am either attaching to myself or letting others do that.

And so I'd invite, those listening what are those? And then when it comes time to tell a new story, there are really three elements that I think of three step process. First is identifying the story, that negative story that may be holding you back. The story I'm telling myself is blank.

I'm not a good people manager. I can't keep pace with the change that's going on in the world, whatever that story may be. The second step is telling a new story. So a new story I'm going to myself, I'm going to tell myself is blank. I'm not good at this yet, or I can be good at these areas.

And then the third step is going out and finding evidence, going out and doing something, taking some sort of action that is going to provide evidence for that new story. An example of this, I'll share, I'm big into triathlon. About a month ago, I participated in the world championships out in New Zealand.

It was an incredible experience. But if I go back to middle school, I could not run the mile. We ran the mile every couple weeks in gym and I could not finish it. I get about halfway through and I'm walking. And so I just told myself I'm not athletic. I'm not a runner at all. And eventually I was like wait, I don't think I want this story to take place.

This story, I'm telling myself that I'm a bad runner. What is a new story? And it's I can't do this yet. And then I started to run a little bit. At first it was a quarter mile and a half mile, and over time I found evidence to create that new story, or to solidify that new story, and to build confidence.

So yeah, those three steps. Identify that story you're telling yourself. Two, tell a new story that you would like to be true. And then three, go out and find evidence for that. 

David Rice: Oh, I love that. And that kind of reminds me of my own thing with running, cause I can remember when I was a kid, I hated running.

And then I started running cross country and all, that's just changed my relationship to it. It was like, I needed these little motivating moments, I had always been very athletic and I had these very high expectations of myself. So it was interesting to see that happen too.

Cause I think expectations as now as an older person, right? I think sometimes expectations are a bit of a dangerous thing. 

Nathan Tanner: And that point, before we continue, some of these stories go really deep. They go back to childhood. They go back to a kid in our class who made a comment about us or expectations of a parent or whatever it may be.

And so a lot of these stories, we may be telling ourselves without even realizing it. 

David Rice: Yeah. And that's great that you said expectations of a parent, right? Because you do, you internalize all of that and you start to develop some interesting sort of expectations of yourself out of that.

And I think our expectations for ourselves can be a bit out of whack with like reality at times, right? Particularly for people who maybe they spent a lot of their lives or careers being labeled as like high achievers or high potential. You get into leadership roles and you start holding those same expectations that you have for yourself, but you hold them for other people and that can lead to a lot of frustration.

I'm curious, what advice do you have for preventing your expectations from creating that frustration and ultimately impacting your mindset as a leader? 

Nathan Tanner: It's really important when shifting to a leadership role or a people manager role, just to reset those expectations. Go back to beginner mode. There's a great book from Marshall Goldsmith, and I love the title.

He says, "What Got You Here Won't Get You There". And that's really true when becoming a people manager where you're an individual contributor, your head's down, you're developing skills, you're getting things done. And that's what success comes from. And then you move into a people manager role, and your success is based on your ability to influence and to help other people get things done.

And I found that when making that shift, we default to one of two ways. The first is we're super, super hard on ourselves. But maybe a little bit soft on others and not being able to hold people accountable and hold high expectations. Or we are way too hard on others and the expectations that we have may be too high and we don't spend the time or energy to coach and develop them.

And so it's definitely a big adjustment when we go there and it's go back to beginner mode. What got me here is not going to get me there.

David Rice: That's a good mindset shift. It's an interesting time right now, right? Because there's like all this uncertainty. There's a lot of external pressure often centers around creating.

If you're working in certain spaces, right? Like it takes tech or SaaS, there's this idea of like infinite growth that gets peddled off. And when things maybe don't go your way or you and your teams, don't get the results that you're looking for. You can get into this head space where you overthink things, or you start to question, am I the right person to lead this group?

What could I do differently? That kind of thing, talk a little bit about overcoming that doubt and not internally I would say, catastrophizing failure. When you're feeling those external pressures. 

Nathan Tanner: Absolutely. I have left the corporate HR world and now I'm an executive coach and I work very closely with startup CEOs, founders, senior executives at larger companies. And these are people who are reaching like the pinnacle of success in their career. And it makes it really hard when you have had success to get used to overcoming these setbacks and dealing with some of the failures that come when you put yourself in the arena.

And so one of the tools I found when working with people who are high performers is this principle called the gap and the gain. This comes from Dan Sullivan and Ben Hardy. But I really like it is there's these very highly ambitious people. We're often unhappy when we don't constantly reach a new level of success, and we focus all of our time on the gap.

Here's where I'm at. Here's where I want to be. And Oh, it just seems so far away. And it it makes me want to give up. It makes me depressed, whatever it may be. And so what I do when I work with people is push them to do the opposite of let's focus on the gain. Let's look back a year ago, where were you a year ago?

Think about your day to day responsibilities and what were you doing maybe even five years ago. And let's focus on that growth. Let's celebrate the growth that you have seen, and then use the energy that comes from that to fuel even more growth. And so yeah, rather than focusing on the gap that we have, let's just pause and take a look at the gain.

And one of my favorite tools that I do as a part of this is I call this a greatest hits folder. And it's take all of the big successes that you've had in your career, David, and let's write them down. Like the promotion you had, the challenging deadline that you hit, high praise you've gotten from someone.

And I think about this specifically, for me, I, when I was writing my first book, this was about a decade ago, it was I'm dealing with this imposter syndrome of who am I to write a book? I felt like it was good, but I still lacked confidence. And I remember sharing it with a man named Dave Ulrich, professor of Michigan, one of the top HR gurus, and I was asking him to write a blurb for it.

And I sent it to him and I'm like, Oh, I don't even know if he'll read it. And he wrote back later that night and had found time to read it and wrote the most glowing piece of feedback for it and like it just changed everything for me and so that goes into my greatest hits folder and okay if i'm writing something and i'm struggling with confidence i'm like oh You suck.

You're terrible. That negative self talk comes in. It's nope. Let's go back to some of that positive. Let's avoid focusing on the gap and spend some time on the gain. 

David Rice: Yeah. It's like almost like internalizing that idea of no one remembers your losses, but you remember your wins, like the old Michael Jordan quote. I always love that. Definitely celebrate your wins, right? 

I saw a post you put up recently and you were talking about the power of realizing that no one cares about your journey like you do, right? And this is a good segue. So everyone is consumed by their own journey. Nobody really has time to judge you or impact what you're doing in a significant way, really.

Talk to me about how liberating that realization can be for you and how it changes the stories that we tell ourselves. 

Nathan Tanner: This was actually a fairly controversial post because I came pretty hard, like no one cares about you, which I'll get to in a second. I was telling this story from my experience of I started my career in investment banking.

I networked, and I got this job on Wall Street, and I was so excited, and then it was at Lehman Brothers, and Lehman Brothers implodes, it's the largest bankruptcy in U.S. history, but I stay in finance for a while. I decide finance is not the right path for me for a variety of reasons, and I'm about to make this big transition to the human resources, people space, which is a drastic jump. 

And some would argue, in iBanking, it's a very prestigious role, and people, may think highly of you, and I'm going to HR, and HR gets all these jabs and jokes, and you think of Toby from the office. And I was like, so worried about what people were going to say, even though I knew this was the right decision for me.

Oh, what are my peers gonna think? What are some of the mentors that I have going to think? And as I told them, I'm like I'm like hemming and hawing about it. And nobody cared. Nobody cared. And when I say no one cared, it's not that nobody cared about me. They certainly cared about me. They wanted me to be successful.

They wanted me to be happy. But no one was like, Oh, why would you do this? Or why would you do that? And so I think there are times where we can get caught in our heads a little bit around how people may be judging some of the career decisions that we have. And just do it have conviction and like the people who really care about you, they're going to support you, they're going to champion you, they definitely care about you as a human, they just don't care about the steps you may be taking to get to your ideal path.

David Rice: I think it's also reassuring, right? It means that your identity isn't attached to The specific thing that they see you as like a human being, a complex creature, right? It's not just Nathan, the finance guy. It's, it's, you're a person if you want it, if that's your goal, then, you go for it and people just support you.

Nathan Tanner: It becomes very freeing. And I think once someone has done this before, it gives you the confidence to then do it again. I think it can be very challenging if you've been in a career path for an extended period of time. That takes some courage and that takes maybe some support for mentors and peers and all of that.

But once you do it, there is a renewed confidence that can come. 

David Rice: That's something that we're going to be seeing a lot more of, right? Because we're seeing right now, a lot of people are going to have to upskill or change careers. They may be going in new directions in some case in midlife. And it really has the potential to tamper with how they see themselves, their identity, right?

Their sense of self and how they see their value, of course, like it impacts our internal narrative that we're talking about crafting here. So what advice do you have for people who, as they shift maybe into something new or start having to do something that they never expected in terms of the story they tell themselves, how can they make it themselves a little bit more resilient through this and build that into the story?

Nathan Tanner: The first step is realizing you're probably going to have to take a step back. And that may be in terms of job title. That may be in terms of compensation. It may not, but often when you're making a big change, there can be a step back. And that's really challenging because it feels Oh, all of my experiences that I've had, all that I've learned is out the door.

And I felt that way when I made the jump from finance to HR. I'm like, Oh, I spent five years grinding and 80 plus hour weeks and all that. Now I'm starting from scratch. This was a waste of time. When I moved into HR, it was a very different story. In fact, I got hired at DoorDash because I had an investment banking background.

The CEO was a former consultant and he really liked the skillset that came from that. And then I've also found that while working in HR, coming from a different background, a finance background, it really gave me a lot of credibility with the leaders that I was supporting. And so no experience is wasted.

I would urge people like focus on skill acquisition, regardless of the path you're on, sales, marketing, finance, HR, whatever it may be. Focus on skill acquisition and down the road, I promise you'll find a way to combine all those unique skills that you've had. And that's really going to fuel your growth going forward. No experience is wasted. 

David Rice: No, I love that. I couldn't agree more. I've experienced that myself, 

nathan, I definitely want to thank you for coming on today. Before we go, I want to give you a chance to promote, whatever it is you're working on, tell people where they can find you learn more about what you're doing.

Nathan Tanner: I'm very active on LinkedIn. Come say hi on, on LinkedIn. Also, as you mentioned, I wrote the book, "The Unconquerable Leader: Mastering the Internal and External Game". And that's where I dive deeper into some of the principles that we discussed and also create a plan and a roadmap for how to implement those things.

So yeah, check out the book and then come say hi on LinkedIn. 

David Rice: Definitely looking forward to reading it. The other thing that we always have to do here on the podcast, we have a little tradition where you get to ask me a question. So I want to turn it over to you. Ask me anything you want. 

Nathan Tanner: Yes. I love that you do this, David.

I'm curious, what's an experience you've had in your career that felt like a failure at the time, but in hindsight turned out to be a major blessing? Or said differently, what's a setback you've had that actually turned into a success? 

David Rice: I think, it was the start of my career was really rough when I came out of college, the recession had just happened.

It felt like a collapse at the time, cause all the opportunities dried up really fast and it was I had to really grind to get by for the first five years. And that felt like it's never going to happen for me. It's just never gonna, I feel like it's never going to break. And I was learning a lot because of the amount of work that I was doing and the type of work that I was doing, I was having to be very flexible.

I had this sort of identity coming out of college, like I wanted, I thought I was going to go down this path, and I'd always charted that course, and that was how I thought it would be when I came out, because I worked really hard to make that happen, and when it didn't form, it didn't form. I had to just be very open minded about what the possibilities were and start writing all kinds of things, and it felt like this isn't the realization of my dreams, right?

This isn't what I wanted. And I went and I did something else for a couple of years, and I realized I definitely didn't want to do that. But when I came back, what I'd found was that there was this whole industry that had opened up around content marketing, and they were looking for people that could just tell stories in really compelling ways.

That's what I'd been mastering during those grinding years. Like I had been working really hard to become good at that. And so actually it wasn't a failure. It was just setting me up for the rest of my life. You know what I mean? Those first really painful years where I was like barely paying my bills and my credit cards were getting maxed out all the time.

Every time the car broke down, which was a lot, cause I didn't have a very nice car back then. It felt like this big grind. And I kept thinking like, while this didn't work out, I failed. And the truth is I was really just setting a foundation that I didn't realize was going to bloom into something completely different later and become my long term career.

Nathan Tanner: Excellent story. And as a good reminder that like success takes time, even when we're doing the right things, there's just a level of consistency and time that needs to take place in order for us to reach that. And I'd imagine if I don't know, after the first year or two, you're like, Oh, things aren't working out, throw it out the window.

You wouldn't be here now. It's a great lesson. 

David Rice: Yeah. I appreciate that. Thanks again for coming on today. I really appreciate it. That was a good question. 

Nathan Tanner: Thank you so much for having me. My pleasure. 

David Rice: Absolutely. 

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