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Your Work Friends
The Ego Equation: How CEO Dan Springer Balances Leadership Success
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 = Success. 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 performance reviews that actually motivates
- Signs your ego might be sabotaging your leadership success
- The mindset shift that helped Dan lead through IPOs and layoffs
Whether you're a new manager or seasoned exec, this episode delivers real talk and actionable strategies to lead with humility, clarity, and purpose.
Join us as we break down Dan's ego insights into strategies you can use right now—because leadership is chaotic enough without having to figure it all out alone!
Episode Highlights
⏰ 3:45 The Ego Equation: Dan's brilliant formula (Skills ÷ Ego × Hard Work = Success) for measuring your leadership effectiveness and why a score of 16 is actually pretty damn good
⏰ 9:30 Leadership Origin Story: How Dan transformed from self-described "prodigious ego" guy to discovering the power of putting the organization first
⏰ 14:20 The Layoff That Changed Everything: The shocking moment when laid-off employees checked in on HIM that completely transformed Dan's leadership philosophy
⏰ 19:45 We Not Me: Why saying "we" instead of "I" gives you unlimited bragging rights (and actually works better for your career)
⏰ 23:10 Performance Reviews Reimagined: The counterintuitive approach Dan used at Responsys that flipped traditional performance management on its head
About Dan Springer:
Dan Springer is the former CEO of DocuSign and a seasoned tech leader with decades of experience scaling some of the biggest names in SaaS. Before DocuSign, he was Chairman and CEO of Responsys, which he successfully led to a $1.6 billion acquisition by Oracle. He’s also held leadership roles at Modem Media, Telleo, NextCard, and began his career at McKinsey. He’s led billion-dollar exits, built high-growth teams, and knows first hand how ego can make—or break—great leadership.
Disclaimer: This podcast is for informational purposes only and should not be considered professional advice. We are not responsible for any losses, damages, or liabilities that may arise from the use of this podcast. The views expressed in this podcast may not be those of the host or the management.
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I try to define ego is.
Speaker 2: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 family. It could be. Any type of organization you're involved with puts that first.
Speaker 1: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 ran 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.
Speaker 3: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. Yeah, there is some secret sauce that he shared with us. That's pretty awesome.
Speaker 1: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, teleo, 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. And you're right, mel. He brought this refreshingly honest take on what it really takes to lead well.
Speaker 3:I think this is one of my favorite episodes so far and one of my favorite guests. The insights he brought were really valuable and others will get value out of this too.
Speaker 1:It wasn't his Dave Matthews story.
Speaker 3:I did love Dave Matthews as a fellow DMV. The fun fact in Connecticut I was at the Meadows with my friend for a DMV when there was an entire flipping of the cars and arson back in the 90s 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 Impel lot.
Speaker 1:Listen my favorite Dave Matthews story, can I tell you, yeah. So there is something I celebrate every year, which is the anniversary of the Dave Matthews Band tour bus. Oh, the bridges in Chicago. And if you don't know this story, Mel, can I tell this story? Yes.
Speaker 3:They're probably like please not again, just when we're not brought up, so I've never been in Chicago.
Speaker 1: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, etc. They are typically open boats, so think about massive kind of pontoon boats looking up and admiring all the skyscrapers.
Speaker 1: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 graded bridges and the bus driver accidentally decided to dump the toilet out and it dumped all over this architectural horror 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 it's so man dave matthews, you know what I'm saying.
Speaker 3:If you were on that boat, the universe was just like f you, in particular today. What like?
Speaker 1:but you've got some explaining. 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 back 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?
Speaker 3:And you can do this equation yourself tomorrow to gut check your own ego. Yep, good tool, right away, great tool, and with that here's Dan Dan.
Speaker 1:how are you today?
Speaker 2:I'm doing great Thanks for having me.
Speaker 1:Great, absolutely All right. I want to get you right into this. We're here to talk about ego and leadership and your background. I'm so excited for it.
Speaker 3:All right, we want to start in understanding your origin story around the whole concept of so and ego and the role ego has played, and so I'd love to understand how your own relationship with your own ego evolved throughout your professional career.
Speaker 2: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 is high ego is putting yourself as the primary, putting yourself first in the context. It could be your family, it could be your office, it could be your company, it 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.
Speaker 2:And my own origin story, I think, is a good, healthy, I mean growing up with the world being presented to me.
Speaker 2:In a certain way. It was 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, been really dedicated to whichever 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 a selfish SOB, maybe it would be more accurate. 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 that was probably my. So I was. I'm embarrassed to say that now, but early thirties before I probably got to a reasonably evolved sense of ego.
Speaker 3: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 it's totally understandable. We're in the non-judgment zone, by the way.
Speaker 2:All right.
Speaker 3:So 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?
Speaker 2:Yeah, so 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, a econometrician, I did modeling and I showed up and they didn't have sophistication at Pacific Valley at that time. So I quickly got promoted less than a year in my first job as a 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.
Speaker 2:But I couldn't figure out for the longest time why. And it was because I was a little jerk. I couldn't figure out for the longest time why. And it was because I was a little jerk. And who's this little jerk telling me he's experienced and good people with probably a condescending ear if we want to be honest about it. But I eventually got that feedback so 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 the it 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 and I ran a company you've never heard of called Tellio. It was my first time as the CEO and I ran it into the ground.
Speaker 2:we sold it for 50 bucks to our Donnelly maybe a little more, not very much money, and so that's why you've never heard of it and I will bury the details of the company. It's important to me but it won't be to your audience. But something happened is right after I joined. It was like 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, in a manager role, in a manager role. I've been a consultant at McKinsey, so I've 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 telling you to beat the crap out of?
Speaker 2:me, I can figure out why they don't want to stay around 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 of years.
Speaker 2:That was this incredible strong feeling.
Speaker 2:Every time I thought about it it made me feel worse, obviously, because these are 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.
Speaker 2: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, 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, and not everyone feels that way. I think it's really important If you're not feeling that way, not caring that much about your people, what are you doing in management?
Speaker 3: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, so life is bigger than that.
Speaker 1: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 were being a jerk to the Yellow Pages people. 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 that lesson around. Don't be a total asshole to people. But one of the things that I love about what you've come up with is an ego equation or an equation 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 degree 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.
Speaker 2: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 people we can really grasp these concepts. The simple expression which I've used in this so like sewing needle and 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.
Speaker 2:As I mentioned earlier is your ability to control your focus on yourself versus to the broader organization, and then, as you said, how hard you work. And the equation for 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 yourself. I'll give you my own self-assessment, so yeah, and then we're, we're on this spectrum think of this bell curve spectrum, not a one to five.
Speaker 2:When it comes to skills that have been built, I think I'm a four. Most of my life asserted I was a five, but we can get to the ego point. I just had a lot of good fortunes. It's not so much that I'm smarter than other people or more skill, I just showed up in some really good situations that made me look good. So I've had a lot of serendipity. And then the ego. And again I don't think I was ever a five.
Speaker 2:On the ego, Maybe I was a four. There's a distribution curve and there's other people out there that could be pretty condescending, jerk like 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.
Speaker 2:So if you use the four, two, four, you say four divided by two is two. You raise that to the power of four and you get two, four, eight, 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, it 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, it's effective. A person working really hard has all focused on themselves could actually be a detriment to an organization. So that's how I think about the formula and have to 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.
Speaker 1:Let me ask you this so you're 16 and you're 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.
Speaker 2:16 is good and again, it's my form. I'm not going to create a system that I have a terrible outcome in.
Speaker 2:And you're like, wow, I really need work, I have to change the model. But 16 is good, have to change the model there. The 16 is good and the real challenge is it's the most of us, of course, most situation. I'm talking about me as a software exec to 16. Um, by the way, the only place I've ever been better is actually in in in sports, and the reason is and this is that you're really fortunate if you have this makeup my whole life, life I played sports all through college, division III college, but still some of my college soccer and lacrosse teams.
Speaker 2: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-knowledge 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, cross, whatever but nobody worked harder.
Speaker 2:I don't believe anyone on any team I was ever on. I know it was a pretty aggressive statement to make, but I can't. How are you going to know? How are you going to refute it?
Speaker 3:anyway, Ever Sounds a little like. Ego Sounds a little like ego.
Speaker 2:Yeah, I hadn't thought about it that way. Can you have ego about how hard you work? 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's work, and that was the joy I had as being a playmaker and trying to make other people score and succeed. So in sports it's the only time I've ever been ever better than I have as a profession. But I would just clearly say 16 is taking 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, and so if you had a team of 16s, that would be a killer team.
Speaker 2: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.
Speaker 1:Is there ever a situation where you need to have hot ego?
Speaker 2: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 they can be healthy ego for sure, in the construct that I'm defining. I don't think so. I think it's optimal is 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.
Speaker 2: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 should answer your question. That's supposed to be a high ego place. Now, over time, that can have become destructive, and yeah, but I think that's the balance. Leadership and 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 together.
Speaker 1:You've taken your career where it is based on this model. You see it and evaluate your teams based on this model. We doubled down on ego, but I would love to understand what do 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.
Speaker 2:One thing I tell you about the skills side, the hardest part about skills, it's the one I think we can do the least Now it doesn't mean you can't take classes and get training things, but core thing that drives and in fact you didn't ask if I stole this idea. There's no SEW, 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, clemenger, and he actually initially his thinking was it wasn't skills, it was smarts. It's also smarts are trainable. It's a very McKinsey way to think about it. Right, and he'd been a career 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.
Speaker 2:You can work on it. You're born with what you got. Thank or don't thank your parents, but 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 quote unquote improve your smarts or your skills it's the learning you get, it's taking wisdom from your experiences. So what makes you smarter, effectively or more skilled is the fact that you have 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.
Speaker 2:You're given processing capability and then the one is applying yourself, and if you just do more and you're active, it goes back to the work. How hard you work. If you take on opportunities. Every time you have 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 smart skills and on work, that's probably the least complex, right?
Speaker 2: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.
Speaker 1: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 like these magical times, right, these magical cultures where you wanted to show up, right, it's the context of it, or is it the individual that's always going to have that lens, or is it a combination of both? I think it could be situational, right.
Speaker 2:Yeah, but your point about the magical times what makes people remember times as magical is because they work really hard with a group of people they respect and care for and built a great album, 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 Responses 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, it felt more like a college reunion than a company had been part of. You had something special and that culture that you were part of will always be important to you.
Speaker 1:It's the power of when you have this in masses, right, when everybody is pulling in their weight or has a high SO score, right. That's the power of that too. 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. I think that's common.
Speaker 2:I think that experience you're describing is probably common and I would say there are times, particularly in 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're riding 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, it's not as special to you as if you know that you really applied yourself fully.
Speaker 1:Yeah, you got to be invested.
Speaker 3:Something that really resonates with me with what you said, because, as another former athlete but I will say I was D1. Just rubbing it in 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.
Speaker 3:Oh, the people who give heart, like you have the heart in it. Is that what you mean when you say hard work absolutely?
Speaker 2: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 again, I never rode crew in any close to 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 on the West Coast, I'm going to start and for the next six, 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 that's our form, and there's probably some track and field things that are like that a little bit, and it's the only one you do in unison, depending on three other, seven other I guess, four and eight if you count. But what a crazy bond that people must have with the team when you go through that.
Speaker 2:You've probably seen it, but you see the boys in the boat. There's a movie from the book the Boys in the Boat. The book was better than the movie. Usually Not always, but usually it's the University of Washington men's crew that won the Olympic gold medal in 1936. No-transcript.
Speaker 3:Oh, I loved crew. By the way, I think when I talked to any of my teammates, most of us did it so we could watch the sunrise before class, because it was just a fun experience at 5 am.
Speaker 3:I wanted to go back to those high-performance work cultures, because we've all worked in them, right, like I worked in big law. We work cultures because we've all worked in them, right, like I worked in big law. We've worked in the big four, all of those things. Do you think something has to happen in terms of, like performance management? Performance management set up in a way to be egocentric or to build ego, because there's always this kind of back and forth? Do you brag about the work you've done and that impacts your potential bonus and your raise or your opportunities for growth, but none of us get our work done, necessarily as individual contributors. Even when you're an individual contributor, you still need others to complete your work, and 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?
Speaker 2:I think so. Yeah, and I'll tell you the first thing. There's certain things in business life that are close to universally. True. There's probably none that are quite, but there's two I want to talk to One related to your question, but first I'll do the other one.
Speaker 2:It's amazing how what we learned in kindergarten is so important for what we do in life. Saying please, saying thank you and saying I'm sorry when appropriate is the simplest thing to do, and when we don't do it oftentimes it leads to fairly significant conflict and problems. I'm not saying it always solves everything, but at least creates the opportunity and the space to be successful. And one of the things that I think is really corollary to that is about teams that you described. And if you say we instead of I, first of all people know.
Speaker 2:So if you're so worried that you have to be clear that you did something, the detraction that you're going to get from your colleague to everyone else I need you to point out that it was you Way swaps, any extra benefit you might get in bonus time or what you're just got, is my opinion.
Speaker 2:But if you do that chest beating and you do it around a wee, it's amazing how everyone gives you license to brag all you want because it's about wee, and if you figure out a way to try to give the credit in a credible way to other people, because we've all seen the bullshit, the fake oh, thank the little people, because it wasn't me and you just look and you're like, okay, that not only gets you the credit for having delivered the great results that your team's done, but, more importantly, that we language makes everyone else feel great and it sets us up for another success, because now everyone wants to do it again. So you're also building followership from teams. So I think that's the answer to the question is just be a we oriented and get away from needing to point out what people probably already know when you've done something great.
Speaker 1:Yeah, I'll tell you too, where I've seen people be really successful is with that we language and that authentic we language like you talked about, with their team, and also cross-functionally as well. When you can be we, when you're reaching across the aisle with finance and HR and marketing and you're going at it we as one, that is hugely powerful, especially as you're going up in the ranks.
Speaker 2:And I would also tell you I think it's powerful when you're the hardest grader on yourself. A lot of people say they're the hardest grader on themselves, they're toughest on themselves. I don't always find that to be the case and I find if you can do that and get a reputation amongst your colleagues for being tougher on yourself than you are on them, it's a really exponentially improving opportunity. I'll give you one sort of dumb example. But at Responsys I had this thing where I tried to change the way we thought about performance reviews. So we did everything out of 100. It's just just like a hundred. But a hundred was perfect Pretty hard to be perfect and I was CEO for 10 years at Responsys. I had twice a year had a review and I would submit my self-assessment, just like I would have all my managers first submit a self-assessment, and I never had a hundred. I never got above low nineties and we had a couple of quarters that led to a half year performance that you would say those were pretty good and I had a board that would push back and say come on, this has got to be a hundred percent and I'm like a hundred, how can you get a hundred? But what would happen is I'd come in and say, yeah, I think I had an 82. And they'd be this is crazy. You at least have a 90. We have to argue this up to a 90. Think about that.
Speaker 2:Normally my experiences before that was the other way around. I think I'm about 115. And then someone else has to say, god, we really think he's about a 90, but now we've got to say he's an 80 to try to compromise. So it just totally changes that. Every single executive my direct reports at responses but one and I'll get to the one in a second Over time grasped that and said this is the way I want it to be.
Speaker 2:I want to be in a situation when I come in tougher on myself and my manager was me says no, I think better than that. Those conversations are so rewarding and I did. One executive who was very talented and a great executive and he had grown up in a sense of I'm above 100%, everything I do is above 100%, and the math major in me says there is no above 100%. It's impossible to be above 100% Asymptomically. Approaching 100% on most things is almost impossible, and so that mentality to get out of that I got all Ben Antonio, but I got everyone else there and it was I think it was a big part of our culture that then went down and trickled down wherever what it was saying like. Let me be tougher on myself.
Speaker 1:Let me ask you this In those moments, did you want to rate yourself 100? In the back of your mind, were you like I actually was 100, but I'm going to put it in myself at a 91? Or were you like, no, I was genuinely in 91, you wasn't you can't what's truth I think there's times where I thought I was pretty damn good.
Speaker 2:Yeah, we had a lot of challenges too, but the early parts of the company was a complete turnaround. There was some, I think. You know I often talk I'll give you a. Let me answer your question, then I'll give you them. Yeah, there were times when I thought I was great, but because I defined it it as 100%. It's just yeah, you can't.
Speaker 2:One of my pet peeves when people say I gave 110%, you don't have 110. There is no 110. And I appreciate what the construct they're trying to say pushing yourself. No, it's like the crew thing, like my 100% is to get us there in six minutes. I got us in five minutes and 55 seconds. I did more than a hundred percent. Well, you just reset. What a hundred percent is? That's new love.
Speaker 2:But but that concept, yes, there are probably some times when I might've been a little bit I don't know too cute by half about saying no, the IPO was great, it just wasn't really the accomplishment I wanted for the company. I think we could have done better. Or my last time I sold the company at the highest multiple SaaS offer company I'd ever had. That was a pretty good outcome. Ceo should feel good, the whole team should feel good about that. But there were some things that just weren't quite optimized in those periods and I think it's important to always tell yourself that the grade you would give yourself is lower than the grade you'd give the company If you're the CEO or general manager for your business, because telling people I'm better than you are and I'm pulling us up, it's a hugely odd message to send, and you and I have talked about this before.
Speaker 2:I think the leadership model I try to think about is the inverted pyramid. Instead of a CEO at the top and then all these people coming down, I say the job of a leader is to make everyone else on the team successful. So you should think about it as an inverted leadership model. And the simple example is that if you think about a company, particularly if it gets to scale, even if you have a lot of self-confidence, managed ego I have a lot of self-confidence. The best I could be at a company of scale let's say there's a thousand employees maybe I could be as good as three or four people. I would have to just be in my A game constantly. Best case, I could be as good as three or four actually, but if I could make each of those thousand people 10% better, that's like hundreds of people you've added of good work, so it just swamps it, and so if you get your mindset to think like that versus to think top, down ones, so it just swamps it.
Speaker 2:And so if you get your mindset to think like that, versus to think top down, I think it helps you to achieve.
Speaker 3:I like the we, not me, concept over there. Yeah, when you think about how leaders can accurately assess where they fall on this scale, can they accurately self-assess, or does it require some external measurements? I'm the only one that can self-assess.
Speaker 2:You're the only one Awesome, sorry, sorry. Of course, everyone can do your own self-assessment. In fact, doing a self-assessment is great. More valuable for most of us probably two is to ask the people you work with, ask your colleagues, ask the team you manage, ask your manager hey, how do you think about me? In this format, and that would be the fun exercise. If you're doing it as a management team, I should do this actually my next gig. You should actually just ask everyone to do that assessment for everyone on the team and then you give people the sense of here's what you said about you and here's what the rest of us said about you.
Speaker 2:In each of these dimensions, I think it could be really powerful way, and I'll tell you that the hard part about it is assessing. You try to think about assessing people when you don't have a lot of data. Most people, if you work with colleagues and you ask people oh yeah, francesca, usually people have a pretty similar view. The hard part is like when you're interviewing someone and you meet them and you say, hey, should we hire this person? You're trying to assess how successful they'll be. It's much harder to figure out some of these things. There's some things that are typically around the smarts and skills. People have degrees and things, or people have a track record where they've delivered tremendous performance. So you see some areas where you can get that.
Speaker 2:The ego one, of course, is the hardest one, although the work one is interesting because a lot of people tout how hard they work and again they're just about working hard. It's about working smart. Sometimes you can't completely rock that. You get a better sense from other people, but the ego one is the hardest one and the way I'll give you my fun interview question. I love to ask people. If it were you, mel, I would say hey. So, mel, if I had in the room everyone that you've been working with for the last five years, but you weren't there and I said to them what's really great about what Mel does? What would they say? And then you answered that question and then, when I'm finished, I said, hey, if I asked that same group, what are the things Mel should be working on? What are some areas where you know Mel could be a little more effective?
Speaker 2:What would they say to that? And of course, everyone loves the first question. First of all, they'd say I'm the smartest person. They give you, as they should. You're giving them a softball to say what's great about you, yeah. But the second question is interesting because there's basically three buckets of answers and some people are in tune with issues that they're working on and they've gotten feedback in the past. Maybe they've made some improvement, they know there's more, and that's a really thoughtful and great answer. Another answer is I don't think they have anything to say. Look, that would be it.
Speaker 3:Look at what we're saying. Such a weird response.
Speaker 2:Really they just have. No, they actually just they've never dawned on them that people might not think they're perfect and they may be great but just like. That's an indication that we ought to be probing further how effective they are in teams if it's never sort of done. But the worst answer of all is what I call the faux answer. And the faux answer is let me tell you what they'd say Now. First of all, they say I work too hard and carrying the load of the whole team makes everyone feel terrible because I do so much more than everyone else, and that's a real problem for people.
Speaker 2:And they give two or three things that you're like the most ridiculous fake critique of all time. Then you actually realize this person's smart. They probably have some awareness of things that they could work on and be better, but they're manipulative and they're full of shit and they're basically going to say let me tell you how I can smooth that. That's actually indicative to me. They could be skilled and there might be certain roles where that sort of ability to communicate and feel if they're going to be an actor or something you might say that's a great skill, to be able to have right To improvise that answer. But to be a colleague, that's a person that's I'm going to be wary, I'm going to be wary. Can they really dedicate themselves to a mission to work with other people? So that's a great question to ask.
Speaker 3:I love that question, Someone who worked in talent acquisition. I think it's such a smart question to ask because I've heard also those rehearsed answers and you're like, oh OK, yeah, I don't know about that. What are some ways? I guess, when you think about warning signs Because I would see that as a warning sign, just as you did but 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?
Speaker 2:Core issue of where an ego is a problem is usually not in someone's self-led efforts around their interactions with the team, and so I think where we see people who are less effective team members and aren't able to the company or the team first, that's where you see it and you see it from their colleagues. And what do I be careful about? I'm a big believer in things like 360 feedback. I'm not actually a huge believer in massive programmatic you have your talent, background, sort of solutions but I think the discipline of getting feedback in a thoughtful, targeted way, as opposed to just lots of forms that people start filling out in a shitty way, is not, honestly, the key to success. It is in a thoughtful way, given the person and the individual. You as a manager do work, but getting that feedback from folks is great. One thing to be careful about is just because other people are unhappy with someone or complain about someone doesn't mean they're the problem. Are unhappy with someone or complain about someone doesn't mean they're the problem. A lot of times we ask someone to carry some pretty heavy water and drive some pretty aggressive performance and some people might not like that and they might say that's a bad person. A lot of times. Let's get this at.
Speaker 2:Docusign or CPL would say they're not living the DocuSign values. They were very important. We had this really strong set of values. Docu DocSend's an amazing company and it's got some things that are really strong. By the way, we've had some challenges last couple of years. Some of those values have allowed us, I think, to maintain more success. But it's really easy to pull the values card and say I don't like the way Mel's doing that and so I'm going to say throw the value set. I'd be really careful that the person that's willing to throw that might not just be doing well, they might be actually saying the scrutiny and management I'm getting is making me uncomfortable. And the person is trying to give me aggressive feedback and somehow I missed the memo that said feedback is a gift and since I didn't think feedback was a gift, I think the person's riding me really hard, but actually they're trying to make me better. So get feedback but make sure you're triangulating and then get observations yourself. That's how I'd propose attacking that role.
Speaker 1:Okay, here's a question. I feel like we have a lot of representations of ego in the extreme. I've seen very high up leaders, board members, ceos, it could be even a manager. I've seen individual contributors and they're so egocentric they're bordering on narcissistic or maybe they are or just a straight psycho. We've all worked for them. What do you like? Some of those environments incent that, incent that behavior, reward that behavior. If you're in an organization that you feel like that's happening, or you're walking into a culture where that day that's happening, how do you start to advocate for more of this balance? How do you operate as yourself? If you're someone that isn't that way and likes to operate with more of the balance, do you go? What do you do? What's the play there?
Speaker 2:So, the first thing is why? Why do you want to do what you're describing you want to do? Do you diagnose that there's a problem in the company? You see a performance challenge happening at some point, or we have a nutrition problem because we have some people's behaviors driving good people out. I'd like to try to understand what the thing I'm trying to fix is before I take my remedy. But in general, I'm a big believer in we motivate people with incentive structures. Some of those are financial incentive structures, some of the praise, all sorts of levels that we have for incentives for people. And so if you're driving behavior and you're seeing it not just one individual, but you're seeing it more creep into your business in a way that you think it's not healthy, I'd look at your incentive structure.
Speaker 2:And so one of the phenomenas is you might say we have a lot of individual achievement awards. Let's go to a team award and a company could take a bonus approach and say it's subjectively based on each individual's performance. Or you could say we're going to have a total team outcome. These are our top three goals, and if we achieve them we all win in that award, and if we don't, that's one lever. But I think that kind of concept is thinking about what you've put in place in your organization to drive the behavior you're driving. And the other one and this is one that I don't understand why more people don't do it other than you know. I have some conflict avoidance in my own nature, so I understand it's a human phenomenon. We often avoid conflict, francesca, less you than the rest of us. You're so nice.
Speaker 2:You spiked on that in a good way, but the answer is talk about it. I don't know. We have this thing where everyone's in a closed room secretly saying, oh, Billy's doing this and Susie's doing this. Hey, Billy, Susie, people think you're being a jerk and I don't know why. That's not who I think you are. So let's go show them that's wrong and what are the things we're going to do together to have it? And I think, same thing Not everyone accepts feedback as a gift at the beginning, but you have to explain to them.
Speaker 2:You want to be successful here. You're going to work with me in addressing this feedback and I think you would find most people 90%-ish people if they know that you care about them and they know that you respect them, they will take that feedback and they will want to be better. And there's some people who just can't take it or see it feels too personal and they have to say it's not me, it's the person that's complaining. Understand that there's a cycle. You go through that process. Past that, I think most people can say you know what? I want to be better, I want to be more effective, so I want to work on it.
Speaker 1:Yeah, Mel and I are. We're writing a book and we just came out of research and that's the number one thing around being feeling like you're being respected and valued. You cannot have feedback, trust, development, conversation, anything without that. That is the base, for you have to have that mutual respect and that mutual value, and I think it's something that we overlook or we assume it's just there yeah, right and we've never had a goddamn conversation about it.
Speaker 2:Yeah, and I'll, yeah. Um, and you have data. And so what happens when you have data? You sometimes that ad is just nobody cares what you know until they know that you care. And so if you're there, you say I got all this information, make you better. I'm like, are you trying to make better? If you're there and you say I got all this information to make you better, I'm like are you trying to make better? Are you setting me up for failure? Like when I understand that you're. When you show up to tell me something, it's because you care about me and you care about the success of what we're building together. Yeah, then I really do want to know, I want to understand, I care about this feedback that's going to make me better.
Speaker 1:Yeah, I think starting with care is such a huge thing. Starting with care might be your answer to my next question, which is I'm dead. It's a little crazy out there these days, but it's a little uncertain. Yeah, hashtag tariffs, speaking of incentive structures as opposed to sticks. I am curious, though if you're a leader, especially if you're a C-level executive, and you have the entire company on your shoulders and you're trying to navigate uncertainty it could be now, it could be in the future, I don't care, but I am curious about how you protect that balance of your ego as you're going through that, because I have to believe that it might be up and down, depending on what situation you're in, what win you have, what punch you just took in the phase. How do you maintain and balance that ego when you are just in a blitzkrieg of bullshit?
Speaker 2:Yeah, two things. One, it was harder for me to insightfully answer that question today because I'm at a place where I've had so much good fortune in my career and I've gotten a lot of boost. That makes me feel good about myself professionally, and not that I don't have things I'm constantly working on, for sure, but I've been so fortunate that I don't walk around with a chip on my shoulder that I, you know, because of this crisis or some other, I either need to prove myself. I do feel like I need to prove myself every day, but I don't feel like I'm coming from a defensive way of doing that and proving myself. So that makes it easier. But if I go back a couple IPOs ago, yeah, I think it's a real challenge.
Speaker 2:I think what you're describing is absolutely a challenge, and the more that the market gets crazy your market, whatever that is it's easy to feel like it's unfair and lashing out and attacking, and then sometimes even the people that are close to you. You should be pulling together. Some people are critical of them. We're blaming. You know the blame game. If you just sold more, we wouldn't have this problem. So it's your fault.
Speaker 2:Sales is fault, which has been a huge issue, by the way, in enterprise software the last couple of years, the number of companies, because I spent a lot of time talking to people about running more software companies that say a company is great, the only problem is our sales team. If we just had a new head of sales, it's going to be great. I'm like really, because every software company is saying the same thing. Is it really just the sales leaders? I don't think so, and so I do think the hard thing when everything is going crazy like that is to just go back and say what can I control and what can I not? I can't control tariffs, I can't control any of these things. I have to make decisions based on the fact that some externalities are there and those external factors are happening. But I have to go back to our team and say I don't know what the outcome is. I just can't tell you what the outcome is going to be, but I can tell you what the inputs are and we're going our very best at doing it in the way we believe and at the quality that we believe we can deliver for our customers, for employees, whatever. And let's just do that, because that's what we can control, and I know it's the same thing like stock price is a phenomenon.
Speaker 2:Companies go public and every CEO gives the same speech, or pretty much every CEO. Guys, we can't control the stock price. You shouldn't be spending time looking at the stock price. That response is early on. I made this thing. I said I'm not going to look at the stock price except for Friday afternoon every week. I will not look at the stock If you ask me about it. I don't want to know. I don't care. I don't want to know what the stock price is. What am I going to do on any given day? How are you.
Speaker 1:This is a backward.
Speaker 2:This isn't that. Leaving is a backward indicator. We got to be focused on our business and getting people out of that mindset. Actually, one thing we did response is we had the IPO and we didn't go ring the bell in New York. We did the IPO. We came back to the office and we were with the office and the people and the day after IPO we said let's play Sales to do. We got product to build. We got customers to take care of. We said what happened to go public yesterday? It's fun and Our customers take care of it. What happened to go public yesterday? It was fun and we should all feel good about it. It was a nice accomplishment. Back to work, because it doesn't matter. It doesn't matter in the context of what we have to do every day. I'm sure we care about it and create liquidity for people. Lots of wonderful things that happen. I'm not against celebrating. I'm all about celebrating. Why do we have the opportunity to celebrate?
Speaker 3:Because, because we did these other things really well for the last several years, so let's keep doing those things. Looking back at your younger self and what you know now, what do you wish you could tell your younger self?
Speaker 2:I think probably a couple things. One is I didn't have a lot of patience, I was in a hurry and I think it's okay to be moving fast, but I think I would tell myself as part of that smell the roses, enjoy the time, enjoy the experiences you're having, and I sometimes skip things to get on to the next, and sometimes I think that's a mistake a lot of us make. And life it's not the end, it's the journey and really making sure you enjoy the journey. And that probably is mostly then around investing in relationships, and not necessarily just like your most important relationship, but the people you know that are just wonderful. It could be colleagues, could be friends, any number of places. Really take advantage of those personal relationships. That is what life is fun to do. So that'd be number one.
Speaker 2:Number two, and there's no question, after the practice speech I gave you on this topic earlier, I would tell myself to chill, cool my jets a little bit about then and realize that the joy I was going to get in life, the real joy I have, comes from seeing other people being successful, and I had to accumulate a certain amount of professional success and personal success before I could start to do that. So I missed a lot of years of a lot of joy I could have had. I think I had little snippets of it. I'm not a total jerk. I did care about the people I worked with but it was all in the lens of they could be successful to make me more successful. And if I think I could have just appreciated them more for them and been better for them, starting that sooner I would get a lot more joy. So those would probably be the two things. There's probably a lot of things I would tell myself, but those would be the. Those would be the.
Speaker 3:I like it. The second one, especially when you think of giving their best advice to emerging leaders, that's like a big takeaway that they can start today. Okay.
Speaker 1:Rapid round questions. You can answer these with one word or a sentence, or however long you want. Sometimes these are our most interesting questions. Are you ready to play? I'm ready to play. Okay, it is 2030. What does work look like? Work will be very similar to what it is today in the post-COVID world Very similar.
Speaker 2:All right, interesting. No, I should elaborate. I thought I was supposed to do rapid fire.
Speaker 1:Wait, now, I want to know the answer. Wait, why do you think it's going to be similar? Why do you think it's going to be similar?
Speaker 2:I think we've had a lot of transformational change going into and coming out of COVID and I think the amount of change in the way we work, assimilate is limited. We're humans and we have our patterns and we have our trends. So I think we've gotten to this place. I don't think it's exactly equilibrium, but in terms of our people going to be in the office, are they going to be remote, I think we're getting to that zone of where we're going to be. I would add, I think artificial intelligence will change the way we work, but I think it's going to be less impact. It'll be massively impactful on business, less impactful on people than I think we realize, because we're adaptable and the things that get automated and then we do things as humans that can't be automated. So I don't think that will change as much as some people are forecasting in the next five years.
Speaker 2:Are you an AI optimist? I'm an optimist, for sure. Yeah, I definitely. I have my I call it terminator awareness of what's happening. I just don't see it. I really don't. Maybe it's my. I'm an optimist. I'm also. My faith in humanity is pretty high. Yeah, I'm pretty optimistic.
Speaker 1:That's good. There's a lot of really awesome possibility there. I'm stoked for it. I'm stoked for it. Yeah, what music are you listening to right now?
Speaker 2:I've been listening to Dave Matthews almost nonstop the last 10 days. Nothing wrong with a little DMV. We had Dave come to an event. Jane Goodall introduced him to me. We did an event at DocuSign. He is the funniest person I've ever been on stage with. If he was an actor, I don't know if you know this before he became a musician he was an actor.
Speaker 2:He's been in a number of films since he's become famous, but he is just the funniest. He has the driest, quick-witted sense of humor that I never would have fully understood, even though I've been a fan for years and then joined C&M on stage, so Dave was the bomb Best session ever. At any event, Get out. Yeah.
Speaker 1:I always read him as like either really awkward to talk to or making like really uncomfortable jokes period.
Speaker 3:Yeah, I got the impression. He seems like a good call.
Speaker 2:So he roasted me in front. He had the DocuSign employee base and customers and he was constantly making fun of me in a way that the docuside employee based and customers and he was constantly making fun of me in a way that, of course, that audience love oh sure so you know he knew his audience.
Speaker 2:Um, yeah, he's a musical genius. So you're right, sometimes there's oddities with people who are creative geniuses. Uh, there's some of that awkwardness. He's so genuine. I'll just say one little snippet. We should move past dave matthews, but he moved to seattle from charlottesville where they really got going. So he lives in in the seattle area and up until this is about five years ago, he just moved out of a one bathroom house with his three children and his wife and he was just like, yeah, and driving his 1970 something volvo, he's just a guy, that's like.
Speaker 2:I don't have any heirs. He's just the same person that I think he wanted to be ever since he was probably 20 or something like that. Yeah, he's a treasure.
Speaker 1:See that story restores my faith in humanity. Honestly Like that's it. Okay, what are you reading? What are you reading?
Speaker 2:So I just finished reading something I half read. It was embarrassing Principles by Ray Dalio, which is a tome of a big book. But the exciting thing that I just started reading again and I think I read it before. But I'm embarrassed. I can remember his Profiles in Courage. It was a Pulitzer Prize winning, jfk wrote it and it's one of those books that everyone knows about, but then you just maybe never read. And anyway, jillian got it for me and I saw it at a bookstore. He's a bookstore and I'm reading it and he's a gifted writer, in addition to being such a special politician.
Speaker 1:It's also interesting to go back, even if you have read something way back, to go back and reread it. All right, here's my last question for you. What piece of advice would you give someone? What's your best piece of advice for them?
Speaker 2:Oh, if it's mildly professional advice I suppose there's other realms, but I guess this would fit more broadly is in life the key is to find I used to be a consultant, so I like to do everything in two by two matrices. It is to find the combination of the things that you're good at and the things you like doing and get into that upper right corner. And I think the biggest thing that people sometimes forget is the things you like, and I think we're naturally drawn to. We get positive feedback on the things we're good at, but finding that intersection of the things you really love doing, that's the thing that you need to focus on.
Speaker 1:It makes it really enjoyable, right? I look forward to it.
Speaker 3:Cool, love it. We appreciate you being with us today. Thanks for joining us.
Speaker 2:Me as well. I really enjoyed it. Thank you for having me.
Speaker 3:This episode was produced, edited and all things by us myself, mel Plett and Francesca Ranieri. Our music is by Pink Zebra and if you loved this conversation and you want to contribute your thoughts with us, please do. You can visit us at yourworkfriendscom, but you can also join us over on LinkedIn. We have a LinkedIn community page and we have the TikToks and Instagrams, so please join us in the socials. And if you like this and you've benefited from this episode and you think someone else can benefit from this episode, please rate and subscribe. We'd really appreciate it. That helps keep us going. Take care, friends. Bye, friends. Thank you.