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Dan Springer
Former Chief Executive Officer, DOCUSIGN INC

The Ego Equation: How CEO Dan Springer Balances Leadership Success

📅 Apr 15, 2025 Your Work Friends 56 MIN 81 VIEWS 80 SEGMENTS · 3 SPEAKERS
What makes great leaders different—and how do you measure it? In this episode, we sit down with former DocuSign CEO Dan Springer to unpack the Ego Equation(Skills ÷ Ego) ^ Work = Your SEW Score..Dan shares leadership lessons from decades in tech, including how ego almost derailed his career and what changed after a layoff turned into a leadership awakening. Listen for: The Ego Equation and how to assess your leadership effectiveness How Dan’s leadership style evolved from ego-first to impact-driven Why using “we” instead of “I” boosts credibility and career growth A fresh approach to perform...

Questions asked in this interview

12
  1. 7:13What other kind of pivotal moments did you have that really transformed your understanding of ego, especially in leadership?
  2. 14:18What's considered like a good score?
  3. 17:54... double down on ego, but I would love to understand when you think about skills and when you think about hard work, what would you recommend people consider when they're looking at upping those potentially just to balance out the equation?
  4. 20:29The context of it, or is it the individual that's always going to have that lens, or is it a combination of both?
  5. 24:47And so do you think there's an opportunity for organizations to think differently about performance management and how you brag about the things you've done while also bringing along everyone else who helped you get there?
  6. 30:38In those moments, did you want to rate yourself 100?
  7. 37:19But when someone's in the job, what are some of the warning signs that indicate ego might be creeping up or interfering with their leadership effectiveness?
  8. 48:02Looking back at your younger self and what you know now, what do you wish you could tell your younger self?
  9. 49:50Sometimes these are our most interesting questions. Are you ready to play?
  10. 50:21Why do you think it's going to be similar?
  11. 51:14Next slide. Are you an AI optimist?
  12. 53:21What are you reading? What are you reading?
Dan Springer 0:00 ↗
I try to define ego: high ego is putting yourself as the primary, putting yourself first. And low ego, which is preferred in this context, is someone that puts the organization or the greater goals — or again, it could be family, it could be any type of organization you're involved with — puts that first.
Interviewer 0:31 ↗
First, we brought Dan Springer on to talk about leadership and ego. And he's probably one of the best people to talk about this with because this guy has run mega organizations as a CEO, as a board member. He's genuinely a really nice guy, and more than that, he knows how to get returns in a business and really create these workplaces that people love to work at. If you ask anybody who's worked under Dan Springer, they loved where they were working. And so we wanted to figure out what was it that made him who he is and what did he attribute to his leadership success. And what he talked about was ego.
Mel 1:14 ↗
Yeah, he was such a great example of somebody who can focus on the human in the workplace while also having very successful business results, and how those two things went hand in hand together.
Interviewer 1:25 ↗
Yeah, there is some secret sauce that he shared with us. That's pretty awesome.
Mel 1:28 ↗
Totally agree. Dan Springer is the former CEO of DocuSign. He's also still on the board. He's an incredibly seasoned tech leader with decades of experience scaling some of the biggest names in SaaS like Responsys, Telio, NextCard, and he began his career at McKinsey, was a partner there. He's led billion-dollar exits, built high-growth teams, and knows firsthand how ego can make or break great leadership.
Interviewer 1:54 ↗
And you're right, Mel, he brought this refreshingly honest take on what it really takes to lead well. I think this is one of my favorite episodes so far, and one of my favorite guests.
Mel 2:04 ↗
His insights were really valuable, and others will get value out of this too. It wasn't his Dave Matthews story.
Interviewer 2:10 ↗
I did love Dave Matthews.
Mel 2:13 ↗
Yeah, as a fellow DMB fan. Fun fact: in Connecticut, I was at the Meadows with my friend for a DMB concert when there was an entire flipping of cars and arson back in the 90s. So, what the hell? At a Dave Matthews concert. It got out of control. I don't know what happened. And we parked in a McDonald's parking lot. This is just a side story you can take out, but it got towed and we hitchhiked with some randos to go find our car at the impound lot.
Interviewer 2:41 ↗
Listen, my favorite Dave Matthews story. Can I tell you? So, there is something I celebrate every year, which is the anniversary of the Dave Matthews Band tour bus over the bridges in Chicago. And if you don't know this story — Mel, can I tell this story? Yes. They're probably like, 'Please, not again, just when we've been brought up.' So, if you've never been in Chicago, there's the river in Chicago and then it dumps out into the lake. And over the river are a series of bridges that are grated and they can lift up and down so tall boats can go through to the lake. Keyword: grated. The other thing I want everyone to know about Chicago is it's a massive architecture town. So, they have these wonderful architectural cruises. If you ever go to Chicago, you have to go on them. They're fantastic and you can see all of the different buildings and the stories behind them. They are typically open boats. So, think about massive pontoon boats looking up and admiring all the skyscrapers. On this very warm summer day, there was an architectural boat cruise cruising down the river, looking at all the skyscrapers. And at the same time, the Dave Matthews Band tour bus was going over one of these grated bridges and the bus driver accidentally decided to dump the toilet out and it dumped all over this architectural boat. So, it is one of the most disgusting stories, but also one of the funniest stories on the planet. I love to tell it just because Dave Matthews, you know what I'm saying? If you were on that boat, the universe was just like, 'F you in particular today.'
Mel 4:19 ↗
I love talking with Dan, not only about the Dave Matthews story, but about his experience and how he's really looked at ego in this equation. If you don't know Dan, he's also a mathematician — well, liberal arts major, which I love. But he has this idea of how do you manage ego with skills and hard work. How do you pull that into balance to really set yourself up for success and to set your team up for success as well? And you can do this equation yourself tomorrow to gut check your own ego.
Interviewer 4:49 ↗
Yep. Good tool right away. Great tool. And with that, here's Dan.
Dan, how are you today?
Dan Springer 5:06 ↗
I'm doing great. Thanks for having me.
Interviewer 5:08 ↗
Great. Absolutely. All right, I want to get you right into this. So we're here to talk about ego and leadership and your background. I'm so excited for it. All right, we want to start in understanding your origin story around the whole concept of ego and the role ego's played. And so I'd love to understand how your own relationship with your own ego evolved throughout your professional career.
Dan Springer 5:29 ↗
I've been called by many, particularly as a young man, to have prodigious ego. So I guess this is a good topic. The simplest construct around that: I try to define ego as high ego is putting yourself as the primary, putting yourself first. In the context, it could be your family, could be your office, could be your company, could be your sports team, whatever it is. And low ego, which is preferred in this context, is someone that puts the organization or the greater goals — or again, it could be family, it could be any type of organization you're involved with — puts that first. And my own origin story, I think, is a good, healthy bug. Growing up with the world being presented to me in a certain way, when I was growing up I was pretty egocentric. I think I was pretty focused on Dan. And although I had wonderful role models like my mom, my hero, who demonstrated to me by putting me first and really dedicating so much of her life to me, I probably should have seen that sooner. But I was a little slow on the uptake. And somewhere probably in my late 20s, I at least became aware of the fact that I was a little bit of a selfish person, or selfish sob maybe it would be more apt. And then professionally I started to figure that out a little bit in leading people. But it wasn't until I had my first son that I think I really figured out that it wasn't about me. And once you have that ability to love someone more than you love yourself, it opens up your ability to just be much less egocentric in everything you do. So I'm embarrassed to say that now, but early 30s before I probably got to a reasonably evolved sense of ego.
Mel 7:13 ↗
Yeah, that makes sense, right? Our brains aren't even fully formed until we're about 24, I think. So to make good decisions and things like that, so totally understandable. We're in the non-judgment zone, by the way. All right. Thank you. So I think having your son, obviously, major pivotal moment. What other kind of pivotal moments did you have that really transformed your understanding of ego, especially in leadership?
Dan Springer 7:32 ↗
Yeah, two actually. One before I had my son, in my first job managing people. So I worked for the phone company. I was a forecaster, econometrician. I did modeling and I showed up and they didn't have sophistication at Pacific Bell at that time. So I quickly got promoted, less than a year in my first job after college. And I was now managing people my parents' age that had been professional forecasters but didn't have some of the technical skills I had. And I quickly realized how bad I was at the job. But I couldn't figure out for the longest time why. And it was because I was a little jerk. And this little jerk was telling experienced and good people what to do, probably with a condescending ear if we want to be honest about it. But I eventually got that feedback. I did get a snippet: being a jerk is not the best archetype of manager that you probably want to have. Then I think fast forward to probably having a son. But there was one period that I think was really powerful for me where I started to respect how wonderful some of the people we work with are. I ran a company you've never heard of called Telio. It was my first time as a CEO. And I ran it into the ground. We sold it for 50 bucks, Jon, maybe a little — not very much money. And so that's why you've never heard of it. I will spare you the details of the company, important to me but won't be to your audience. But something happened: right after I joined, it was a dire situation and we had to do a slight restructuring. It was a small company but we had to do a layoff and I had never done that in a role as a manager. I'd been a consultant, McKinsey, so I'd been around a little bit of cost cutting. And that night after the layoff, I was in my office late and four of the guys that had been laid off were standing outside the doors, like a glass door, looking in. And they knocked and they came in. And for a minute I had this thought: are they coming in here to beat the crap out of me? I couldn't figure out why. And these four guys sat down and they just asked to check in on how I was doing. And they said they could tell how difficult it had been for me to go through the layoff — their layoff, not my layoff, their layoff — that they were worried about me. And I'll tell you, for the next couple years, that was this incredibly strong feeling. Every time I thought about it, it made me feel worse, obviously, because these are like the greatest human beings that could get laid off and they're worried about the guy that just came in to be their boss that had to carry out the action. And two, it just made me realize how wonderful people can be. And it's just always stuck with me as a message that we have a responsibility when we lead an organization for those people. And I vowed I would never — it hasn't happened yet, but it could — never have a layoff of people who were doing their job well and were losing their opportunity because leadership, in this case me, failed to provide the opportunity. So don't overhire. Don't get into that situation. And when you have it, it's a painful lesson, but it was hugely eye-opening for me against the quality of people and the really serious responsibility we have as leaders for the people that work for us.
Interviewer 10:31 ↗
Not everyone feels that way. I think it's really important. If you're not feeling that way, you're not caring that much about your people. What are you doing in management?
Mel 10:41 ↗
Yeah. You have to think about the whole person and get down to humanity. At the end of the day, we are bigger than our jobs. Life is bigger than that.
Interviewer 10:49 ↗
Yeah. So Mel and I didn't go to math school, Dan. We did not go to math school. I know you did. I know you have a — you were being a jerk to the Yellow Pages people. Okay. Let's talk about how you were a jerk, Dan. No, I'm just kidding. I was sitting there thinking like you were 30 — I think I was like 35 before I got that lesson around. Yeah. Don't be a total jerk to people. Well, one of the things that I love about what you've come up with is you have an ego equation, or an equation for how to think about ego, because we have all these stories around: it's about how smart you are, it is about your strategy and you're playing five-dimensional chess over here. Or maybe it's about the fact that you work your ass off. I'm wondering if you can talk about the mathy equation you have to think about ego and work and skills as it relates to success.
Dan Springer 11:40 ↗
It's a little bit geeky. Sure. It's only geeky when you put numbers to it. Conceptually, even liberal arts majors like myself — even though I was a math and liberal arts college person — we can really grasp these concepts. The simple expression, which I've just sewn like sewing needle to thread, is: you have your skills, that are usually highly correlated to the fortune you were given with your smarts and your ability to build skills. And then you have your ego, as I mentioned earlier, which is your ability to control your focus on yourself versus to the broader organization. And then as you said, with how hard you work. And the equation, to the geeks out there like myself, is you take those skills that you have, the S, you divide it by your ego. So you want to have less ego, obviously. Then you take that and you raise it to the power of how hard you work. And if you do play around with little numbers, I generally use one to five. And you assess — I'll give you my own self-assessment so you can see where we're at on this spectrum. Think of this bell curve spectrum, not just a one to five. When it comes to skills that have been built, I think I'm a four. Most of my life I asserted I was a five, but we can get to the ego point. I just had a lot of good fortune. It's not so much that I'm smarter than other people or more skilled. I just showed up in some really good situations that made me look good. So I found a lot of serendipity. And then the ego — again, I don't think I was ever a five on ego. Maybe I was a four. There's a distribution curve and there's other people out there that could be pretty condescending jerks, like a two, but I was probably in the four zone. I'm down to about a two in my self-assessment. So I'm pretty good. Not the best, but I'm pretty good at trying to really put the organization first and get out of my own ego. And then on how hard I work, it's four or five. I've been a five at times. Sustaining five is very difficult, but I think I'm a good solid four. So if you use the 4-2-4, you say four divided by two is two. You raise that to the power of four and you get 16. And that's pretty good. And of course, when you're a competitive person like I am, you play this game and you go, 'Okay, what I really want to do is be a five over a one.' Raise it to the — it just really probably doesn't happen very often. And quite frankly, if you have people operating with a high ego, you do the math. If you're around a one, it doesn't matter how hard you work, you're not going to get the number any better. If you're below one, this person working really hard who has all focus on themselves could actually be a detriment to an organization. So that's how I think about the formula, and I could chat about each of the elements more, but I use that in evaluating people and thinking about how effective they can be in our organization.
Interviewer 14:18 ↗
Let me ask you this. So you're at 16, and in your SO score, is there a range? Let's say you're building out a C-suite for example, or you're building out whatever, and you're trying to gauge where people are at. What's considered like a good score?
Dan Springer 14:32 ↗
16 is good. And again, my formula is: I'm not going to create a system that I have a terrible outcome in. You're like, 'Wow, I really need to change. I have to change the model.' The 16 is good. And the real challenge is that most of us, of course, in most situations — but I'm talking about me as a software exec. And by the way, the only place I've ever been better is actually in sports. And the reason is — and this is that you're really fortunate if you have this makeup — my whole life I played sports all through college, Division III college, but still my college soccer and lacrosse teams. But all through school, all through every team I ever played on, I don't think I was ever the most skilled player on my team. And I had just enough self-awareness to know. I think sometimes I was one of the better players. I knew I was never the most skilled player on any — whether it was football, soccer, basketball, lacrosse, whatever. But nobody worked harder. I don't believe anyone on any team I was ever on — I know it's a pretty aggressive statement to make, but I can't — how are you gonna know? How are you gonna refute it anyway? — ever worked harder.
Interviewer 15:40 ↗
Sounds a little like ego.
Dan Springer 15:42 ↗
Yeah, it does. Yeah, I had thought about it that way. Can you have ego about how hard you do it? Maybe. And I do think if you look at the stats score, you'll always see not as many points but a lot of assists from Dan. And that was the joy I had as being a playmaker and trying to make other people score and succeed. So in sports is the only time I've ever been better than I have as proficient. But I would just clearly say 16 has taken me a career to get to. I was realistically a one, two probably most of my career because of the ego that suppresses the ratio of the smarts.
Interviewer 16:16 ↗
And so if you had a team of 16s, that would be a killer team.
Dan Springer 16:22 ↗
Everyone could get their egos down. Some people might get it by a five and a three. You're playing the different modes. But yeah, it's all about getting that balance, right?
Interviewer 16:31 ↗
Is there ever a situation where you need to have high ego?
Dan Springer 16:35 ↗
Yeah. And again, the problem with the definition of the word ego in general — there could be a lot of different nuances and interpretations of that. And I think there can be healthy ego for sure. In the construct that I'm defining, I don't think so. I think it's optimal to be a team player because not only does it help the team's output, but then it forces other people because of that behavior you exhibit to do the same. People want to be drawn, I think, to something bigger than themselves and if other people lead that way it makes it easier. So you have a knockoff effect on other people when you bring down your ego and some cultures can get to the place where that happens. But just to be clear, there's high-performing cultures that have high ego. I worked at McKinsey. There are investment banks. I would tell you most of them is a model where people are fighting, particularly in banks, for their compensation. It's a big thing. It's a 'let me show you how great I was and the deals I got done. Therefore, I deserve more compensation' in that model. By definition, I think you answer your question. That's supposed to be a high-ego place. Now, over time, can that become destructive? Yeah, but I think that's the balance. Leadership in that kind of organization has to figure out a way to maintain that competitiveness around individual performance and at the same time still figure out how do we have some collegial nature that we can build a firm.
Mel 17:54 ↗
You've taken your career where it is based on this model. You see it and evaluate your teams based on this model. We double down on ego, but I would love to understand when you think about skills and when you think about hard work, what would you recommend people consider when they're looking at upping those potentially just to balance out the equation?
Dan Springer 18:15 ↗
One thing I'll tell you about the skills side: the hardest part about skills, it's the one I think we can do the least about. Now, it doesn't mean you can't take classes and get training and things. But the core thing that drives — and in fact you didn't ask if I stole this idea, even though it wasn't — there's no formula quite like the way I do it — but this construct of these sort of three forces in determining how effective people are in their work was stolen from a guy I worked with at McKinsey years ago, an Australian guy, Clem Doherty, and he actually initially his thinking was it wasn't skills, it was smarts. Which is also a very McKinsey way to think about it, right? And even a career at McKinsey was: we just want smart people because smart people will figure out problems, but they'll also figure out how to learn and grow to some extent. Your clock speed — you can work on it. You're born with what you got. Thank or don't thank your parents that you got what you got. So that one is much harder for people to control. And I would tell you the best thing you can do to either improve your smarts or your skills — the learning you get — is taking wisdom from your experiences. So what makes you smarter effectively or more skilled is the fact that you have the ability to take feedback and say, 'Oh, I got to move a little bit over this way.' So that's probably the most important piece, except that a lot of it is going to be your given processing capability. And the other one is applying yourself. And if you just do more and you're active — goes back to the work, how hard you work — if you take on opportunities every time, a chance to do something new and different, you do it. And then you listen and learn about how you did. That's the best thing I think you can do to improve your sort of smarts and skills. And on work, that's probably the least complex, right? And it's just how will you apply yourself. It's definitely about working smarter, not just harder. Although I sometimes think we use the excuse of working smart, not hard, to not fully deploy ourselves and really invest ourselves in the things we're working on. But that could be personal, professional, across the board. We often know when we're just showing up. And there's days sometimes where that's all you can muster, just showing up. But if you find yourself only just showing up a lot of the time, you're probably not in the right place because you just don't have that enthusiasm for your work to allow you to get up to a four or maybe even a five on how hard you work.
Mel 20:29 ↗
Yeah. It's interesting when you have those — where you — is it context? You know what I'm saying? Like when you're in a situation — I know when you were at DocuSign or Responsys, for example, too, it felt like that was these magical times, right? These magical cultures where you wanted to show up. Right? The context of it, or is it the individual that's always going to have that lens, or is it a combination of both?
Dan Springer 20:50 ↗
Yeah. And I think it could be situational, right? Yeah. But your point about the magical times — what makes people remember times as magical is because they worked really hard with a group of people they respect and cared for and built a great outcome. And when you do that, it bonds people. I think we were chatting the other day and I told you that there was this 10-year reunion of people from when we sold Responsys to Oracle. And I thought the whole idea was a little wacky in the first place, to be completely honest with you. And then when hundreds of people showed up and said it was a really special way for them to be back with people — felt more like a college reunion than a company they'd been part of — you had something special, and that culture that you were part of will always be important to you. It's the power of when you have this in mass, right? When everybody's pulling their weight or has a high SO score, right? The power of that, too.
Interviewer 21:46 ↗
Come to think about it, I don't think I've ever had a magical work experience where I phoned it in, or where I was very egocentric, or like I was the smartest person in the freaking room. Like that never ever happened.
Dan Springer 21:57 ↗
I think that's common. I think that experience you're describing is probably common. And I would say there are times, particularly in the technology industry, where you get on a wave and you probably could continue to have great success with phoning it in a little bit. Although be careful, because when you ride in that kind of wave it's going to crash at some point. But I would tell you, I bet it's not a magical experience. I think it's very difficult if you didn't really work hard at something to truly enjoy the success and the outcome because it's not as important. And it's not as special to you as if you know that you really applied yourself fully. Yeah. You got to be invested.
Mel 22:45 ↗
Something that really resonates with me with what you said, because as another former athlete — but I will say I was D1. Just bragging a little, just a little. But I was a rower, so it doesn't really count. As a former athlete throughout my life, one of the things that I heard time and time again from my coaches — and like you, I was never the best. But what I always got was the heart award because when you're the one giving heart — and in my mind when I keep hearing you say hard work, that's what I keep hearing. Oh, the people who give heart, like you have the heart in it. Is that what you mean when you say hard work?
Dan Springer 23:16 ↗
Absolutely. And in fact, it's funny. I was thinking about your point about crew. It actually is a great example because if you think about — and again, I never rowed crew in any close semblance of a real way, but oddly enough, I went to a strange high school in Seattle that happened to have crew, which is unusual, particularly unusual then in the west coast. But I have a huge amount of respect for a sport where you say, 'I'm going to start and for the next six — in about six minutes — I'm going to get increasingly uncomfortable to the point that my body's going to hate what I'm doing and I'm going to collapse in exhaustion.' And you go and that's what we do every time. And there's probably some track and field things that are like that a little bit, and that's the only one you do in unison — depending, what, three other or seven other, I guess four and eight if you count coxswain — but what a crazy bond that people must have with the team when you go through that. You've probably seen it, but you see The Boys in the Boat — there's a movie.
Mel 24:22 ↗
Oh, from the book, The Boys in the Boat. The book was better than the movie, usually. Not always, but usually.
Dan Springer 24:25 ↗
It's the University of Washington men's crew that won the Olympic gold medal in 1936.

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Springer, D. (2025, April 15). The Ego Equation: How CEO Dan Springer Balances Leadership Success [Interview transcript]. Your Work Friends. CEOInterviews.AI. https://ceointerviews.ai/interview/2950384/

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Dan Springer. "The Ego Equation: How CEO Dan Springer Balances Leadership Success." Your Work Friends, 15 Apr. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/2950384/.

BibTeX
@misc{springer2025_2950384,
  author       = {Dan Springer},
  title        = {The Ego Equation: How CEO Dan Springer Balances Leadership Success},
  howpublished = {Interview transcript, Your Work Friends. CEOInterviews.AI},
  year         = {2025},
  month        = {apr},
  url          = {https://ceointerviews.ai/interview/2950384/},
  note         = {Speaker-attributed transcript with timestamps}
}