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Episode 8

Lessons in Low Ego Leadership with DocuSign CEO Dan Springer

In this episode, Mathilde sits down with DocuSign CEO Dan Springer to hear his journey towards becoming a low ego leader and how that impacts the team and business for the better.

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Mathilde Collin All right. Hi, everyone, I’m Mathilde Collin, Co-founder and CEO of Front. Over the years I’ve shared my journey as a leader and as a founder. But really, everything I’ve learned so far has been by talking to people that have more experience than me and that are wiser than me. And this is what I’m going to be doing today. I’m here today with Dan, the CEO of DocuSign, who is known for low ego leadership. And since that’s one of our values that I’m excited to hear his take on it today. Thank you again for being with us. 

Dan Springer Thanks for having me. Excited to be here. 

Mathilde Collin So you’ve been the CEO of DocuSign for four years, if I’m correct.

Dan Springer I want full credit. Four and a half!

Mathilde Collin Four and a half—even better. So I’d love to ask you, what do you like the most about this job?

Dan Springer Well, of course, DocuSign, for me, has been an opportunity to see tremendous growth, and one thing that comes with business growth is the development of the people. And so the real joy I get out of work is seeing the people on my team developing their careers achieve their aspirations. I’ve pretty much achieved what I’d like to achieve. So I’m less sort of driven by my personal sort of accomplishments, if you will, and more by watching those people develop in their careers. And the other part is that I’m still pretty competitive. So I like winning in the marketplace. And I’ve had a pretty good run for all of those four and a half years. A lot of good success. And that’s also really rewarding for me as well.

Mathilde Collin Great. I’ve heard from many people that you’re a great leader and I think you’ve already spent twenty five years in leadership positions. And I’m curious if you have any philosophy on leadership that you’d like to share with our audience. 

Dan Springer Yeah, I mean there’s a slightly geeky term that I like to use to sort of simplify how I evaluate leaders in the company or when I’m interviewing people about potentially bringing in a company which is sort of combining three different factors that I think are really critical. The first one is whether people have the right sort of skills and smarts to be effective in their job. The second one is, are they able to manage their ego and so that they’re able to be manager, you go well, folks on the teams results as opposed to their individual results and credit analysis is simply how hard they work and how much they apply themselves. And the formula that I like to use with those three things is I take the S or the smarts and skills divide that by the ego. Did you want to do a better job minimizing that and then raise that quotient to the power of how hard you work and you can play around with numbers like one to five and do your own assessment. And so to see this sort of interesting things, you do play around with the math. But the key thing for me is to realize that to some extent you can get smarter and you can develop more skills. But we’re all sort of given some certain level of capabilities that we have and some better for some jobs. Once you have that, the parts you can really control with how you manage your ego and how you really apply yourself and how hard you work. And so I try to encourage people to say that’s where you should put your focus and developing yourself as an individual contributor, but particularly as a manager is are you going to be successful by those two variables you can control?

Mathilde Collin And I’m curious, how do you teach people or help people work on their ego?

Dan Springer So that’s the part that’s interesting because sometimes it’s easy for people, some people naturally have high cues. Their personality is to be supportive of other people. They get their joy out of watching people develop. So it’s easy for them to do it. And some people, it’s really, really difficult. And the thing I would tell you is that we’re all on a journey. And when I try to talk to people about ego management, if you will, I try to go back and say, hey, let me tell you, I think today I’ve gotten to a point on a one to five scale, which is I’ve gotten to about four. I think I do a pretty good job of putting the organization first. Customers first. The other employees first over myself. But when I was twenty three, a young person I go, I probably was a one or two on ego. I you know, I was very focused on my own career. I was competitive, I was ambitious. And, you know, I was not great at that. I had some early management jobs where it wasn’t, I don’t think, very good as a manager and very sensitive. I was managing people much older than I was, and I just didn’t have an awareness of how to do that. Well, so you sort of start off and say, I’ve been there is someone struggling, I’ve been where you are. It takes some work. But what it mostly takes is awareness and focus. And so that’s what I try to tell them stories about. Here’s places that I wasn’t aware of. So not just me, so I could be other stories of other people. And here’s what they did to be more successful, because that’s one. And the second big thing is giving people feedback. And I would say feedback is a gift and you need to be able to explain to people why you see them underperforming on the ego dimension and say, this is how I saw you interact with your teammates. And this is what other people say when they come out of interactions with you and why they maybe feel bruised or not supported whatever it might be, and giving people that direct, you know, and really critical feedback on how they’re showing up is, I think the only way you can really help if it’s not about book learning. I mean, you can read stories, but it really is about that intensely personal development.

Mathilde Collin Yeah, that makes sense. One thing that we also do address is every all hands, a weekly company wide. We have this thing called Stumble of the Week. And so anyone that has made a mistake can share the learnings. And I think then you create an environment where people are more comfortable talking about the things that they’ve done well and what they’ve learned with it.

Dan Springer So personal. I tell you, I love your story about the Stumbles because I think humility, I always describe that’s sort of the secret power that allows you to overcome your ego issues just to be able to get comfortable with your own challenges and your own shortcomings. Once you stop, I would say at McKinsey, we always talked about how a lot of people are trying to prove they’re the smartest person in the room all the time. And that’s not great ego management. So you need help to be able to say, you know what, people who aren’t trying to show that they’re smarter than everyone else all the time. Those are the people who are crushing it on the ego management dimension. Let’s celebrate that and your stumbles are a perfect example for how to do that.

Mathilde Collin On the topic of leadership, one thing that I’ve heard is that you have a commitment that is every person deserves a great manager and every manager deserves the tools to become great. Can walk me through some of the tools that help managers become great?

Dan Springer Yes, a huge topic. Can I try to be not too long winded? I mean, I think the first piece is management training. I mean, so one of the things we realized early on as we promoted a lot of people in the first time managers is we are growing. And we in the early days, I think we made the mistake of just assuming, well, if you’re good at that job, if you don’t if you’re a sales development rep and you’re good at that, now you’re managing other assets, you’ll just tell them what you did. And of course, that’s naive. In fact, people could be great at a job and not have those skills. So some of that is around actually feedback and coaching is one of the most important modules we talk about within that management training piece, I think is really important is that we have increasing diversity, an area that tech has not been as successful as we’d like, whether that’s gender diversity, whether that’s racial diversity. And so we do a lot of our management training where we embed the concept of how do you create an inclusive environment? How are you successful as a manager for people that are different than you are? And again, to people early in their careers, they sometimes don’t have that same sensitivity. In the example I used before about myself, I said I was managing people that were that were significantly older than I was in my first manager job. And I did a terrible job of thinking about how they were different than I was, how their motivations were different. I did not create an inclusive environment. I created something far less. So those are kinds of things that I think we do. I’d also say the one thing we heavily leverage is surveys. So we do a lot of employee surveys that I try to do my job better by understanding. We also get information from managers and say, hey, here’s how your department is doing. Here’s how your team and your group are feeling about things. And we use those those things as spotlights to say you have an opportunity where you’re underperforming. You have opportunities to do more of the good. Definitely you focus, do more of the good. But here’s an opportunity where you might not be crushing it. And here’s how the surveys came back. And then the last thing that I would say that gets missed a lot, but I think the most important thing you can do for managers to make them great managers is have incredibly high expectations for them being great manager. And I think we get so much so we can be apologetic and excuses for people and that’s difficult. One of these, we say, is that if you have a direct report team, your job is to make sure that each one of them is doing the work of their life here at DocuSign. And I’m not saying everyone will be a hundred percent successful. Not every single employee here do we get there. But as a manager, if you’re not going to work every day saying your job is to make each of my reports have this the best place they’ve ever worked, and that’s not a high enough expectation. You need to go to work with that goal. "Because this person’s really difficult or this person is...", No, your job is to be successful and you won’t always be. But if you don’t hold that expectation really high, I think we give people an excuse to not be great managers. So that’s that be the last tool that I think is important.

Mathilde Collin That makes sense. And I don’t think I’ve heard as you as you can see, I’ve heard a lot of things about you in leadership and the way you say it is that you personally take a lot of time to get to know employees and you believe that it’s an important part of helping them have the best possible job. And I’m curious, during the past year and a half where we couldn’t travel, how did you build these connections and specifically at scale when you are almost at six thousand employees, if I’m not mistaken. 

Dan Springer That’s right. So the first answer is, so this has been the worst year and a half pretty much in my professional career because one of the big reasons why I haven’t been able to do that. Our business has been thriving, but it has been so difficult for me personally, personally. Part of it is just my own natural style is I’m outgoing and I like interacting with people and I get energy, a big source of my energy is interacting with my colleagues. So it’s really difficult for me trying to do it in this medium. I prefer we’re having this conversation, I wish we were sitting face to face. It would be easier for me in a lot of ways, but so in developing those relationships and investing in the people, we’ve had to adjust. So I’ll take a couple of things. We’ve done what is we’ve done more frequent, sort of all hands communications, town hall meetings where I’m just actually interacting and speaking with both. He doesn’t get me quite as much. I get Q&A at the end, but I think it helps a lot for the employees that are saying there’s a leadership feeling of void where we’re not getting to see Dan or other executives out. And so particularly in international offices where that was a big part of our rhythm, if I was going to be in those offices, we go see customers, I spent time employees, social time together as well and really feeling a sense of sort of an intensity. And so you can’t replace that if you can’t get your butt on a plane and get to those places. But we’ve done some other things that I think are important. One of them is we’ve actually done a lot of informal things, like happy hours with groups or trivia contests and all the things that people are trying to do. And I try to join. So not every single meeting in the company, but I’ve dramatically increased the number of events that I attend around like team meetings. And so I’ve told people you’re having a team meeting and you want me to show up for ten minutes and give a quick update on things going on in the company and take questions? All day long. Because remember, I saved a lot of time by not having to fly around and travel all those offices. I have capacity to do a lot of half hour calls. So I actually try to fill my schedule with meeting with smaller groups where you can have an interaction. And then the last thing, if there’s like a silver lining there a lot. But one silver lining to cover this, we used to have an event for all new employees would come to what’s called Discovery. We fly them to Seattle from wherever in the world they join. That’s where the company was founded and still our largest office, even though headquarters now in San Francisco, and they go through several days of discovery at DocuSign and different people come in and talk. If I was able to be in Seattle during Discovery DocuSign, of course, would always do that. But the reality is, as the months go by, I don’t get to very many Discovery DocuSign. But in a virtual world, I go to every single one. So every new employee that joins goes to a couple of day event called Discovery DocuSign, and they meet me and they interact with me and I answer questions and tell them about the company and talk about our values. At the end, I tell them all the same thing. Here’s my email address. If you ever have a question when you’re not sure how your job connects to our values and you talk to your manager and do not get the answer you need, so you need call me or email me and I will make sure you feel part of DocuSign and be successful here, and how can you do that with 6000 people? Well, the vast majority of people, of course, don’t call you and follow up, because that’s a majority of people were doing stuff right. DocuSign. And they’re lost. Well, no, they don’t need me. But for those people that get lost there or for those people that want that little safety net, it’s actually reassuring. And some people reach out and they reach out oftentimes to help me see a problem. But we’re not doing something well to get their job aligned with our values. So those are examples of things that you can do more of, even independent.

Mathilde Collin One thing that strikes me when we’re chatting is you seem to be a very empathetic person. And one of the things that I’ve learned from the past year and a half is more than ever people in the company needed this empathy. I’m curious if you have any tips on how you can teach people to be empathetic and just what you can do, because I think it’s a great value to bring to the workplace. 

Dan Springer So everyone’s different in how they build their capabilities and awareness on things. I’ll tell you about my path there. I’ve not some of these things might not work for other people. The first thing I say is have children. And when you have children, two great things happen. One, you now have the ability to love someone more than you love yourself. Some people probably had that capability before and I never had that capability beforehand. And then, of course, it was magically easy as soon as my first son was born. So that’s a that’s a no brainer. It might not fit in all your lives as an option, but if you do have it, that’s a great one. Second one is, I think, encourage the people around you that really care about you to give you feedback and particularly give you feedback when you miss stuff and feedback on your insensitivities. Right. So, you know, I’ve got a long history of getting feedback from people I was in relationships with that cared enough about me to make me aware of my shortcomings. So so I think you have to be open to it. I mean, I think you have to encourage people that you’re open to it and then you have to be open to it and then you don’t ever act on it or show any progress. People stop giving feedback because it’s you know, it’s a chamber that’s just echoing and you’re not listening. So it takes work and you have to sort of focus on doing it again. We talk about a development. When I was twenty five, I wasn’t building a lot of empathy and I wasn’t listening to a lot of feedback on my shortcomings in that field. So you have to make it important to have people around you that you care about, know that you want them to share that when you have the misses and that’s where it really is fundamentally awareness. I know people are good people. People want to be helpful. They want to do the right thing when they don’t appear to have empathy, it’s usually because they’re just not aware, it’s an ignorance problem as opposed to a problem. There are a few jerks in the world that are just going to be jerks anyway. But that’s you got to assume good intent. And most people are coming to a place that they want to develop, but they just need help because we’re all human and we’re all imperfect in that way. 

Mathilde Collin Well, I’m very glad I had a daughter nine months ago.

Dan Springer Oh, congratulations.

Mathilde Collin I’m very glad to hear that will make me more empathetic. It has already made me more. Earlier in the chat you mentioned when we were talking about how to coach managers to be great managers, you mentioned that diversity was important. And in the past year we’ve witnessed a lot of racial injustice. And I think tell me if I’m wrong, but I think you said that it was important that we aggressively drive the education process around these topics. And I’m curious how you brought awareness at DocuSign on this topic and why you think this education is so important for diversity and inclusion. 

Dan Springer Yeah, well, so multiple reasons. But we start off by saying everyone likes to talk about their when they achieved something they feel proud of. They talk about that end state. And sometimes we forget to talk about the journey that’s important for people to understand. You don’t get don’t get intimidated by someone saying we’ve accomplished all these great things, we’ve achieved some training goals or some diversity inclusion goals. How do they get there? So I’ll be clear on these journeys that I talk about, that I had a huge gap in my awareness over the last three years. I mean, I’ve I’ve dramatically changed my perspective around social justice aspects that we’ve seen in so many ways, particularly in the last year, year and a half. And I also think that my consciousness was a big gap first. But but my ability to get mature and understand the complexity of some of these issues and severity was big. So if people out there if you’re saying you don’t get it, it’s OK, the water’s warm, come on and start the journey and start pushing yourself to understand. So like a DocuSign, we started off with communication and we said we have to be able to talk about these things. We have a very transparent environment, people can ask questions. We do our all hands, all companies there, people can ask tough, aggressive questions, and that pushes me and the rest of our leadership to say we need to address the things that are on the minds of our employees. So communication was big. We allocate a lot of time to talk about things, particularly with Black Lives Matter situation and sort of the explosion of the awareness for so many of us that we were just missing. And now, of course, we think, how did I not see that? Second when we talked about training, we’re actually trying to put some of that DEI training in all of the managerial training and all of the individual training that we do, not as separate, but sort of said instead of saying now we’re going to do diversity training and if people come in and focus on that and said, how do we integrate that? I think it’s more effective and also takes away some of the cynicism because people come into diversity training with their guard up saying, well, I’m not racist. And that’s not a constructive way to start the conversation. But you understand why people would be defensive, whereas if you embedded in the other programs, the guards come down and they’re more open to it. So that’s been a big focus. Integrate that into training. And the last thing is you got to take some actions at some point. Can’t just be talk. So the kind of things we did is when we put a lot of money behind it and we put matches in place. So actually starting at the time with Black Lives Matter. So the escalation last summer, we did some training education with some speakers and then we said let’s let’s fund some social justice organizations. And we said for employees that give money, the company will match all of their gifts. And then I personally would also match all their gifts so they get three dollars for every dollar that they would put forward and we dramatically increased our dividend. So that was fantastic. DocuSign has really stepped forward with that incentive to give more to these causes. And then the last piece, but maybe the most important is we have to take the actions internally. So we started to publish all of our diversity information. So we now say every year we publish our success against our diversity goals and what our actual demographics are in the company and with the adage that what gets measured and published, gets managed. We’re seeing significant improvement. We still have a long way to go, but we’re seeing significant improvement in improving the diversity of our workforce.

Mathilde Collin I’m sad because we’re you know, we’re almost at the end of our interview and I’m learning so much and I have many more questions, I think I can afford two more questions. But thanks for sharing so transparently everything that you’re doing and learning. If I’m not mistaken, I think you after you sold Responsys, you took two years, four years to just be with your family. And I’m curious why you made the decision and if you feel like that’s impacted the way you lead now. 

Dan Springer Yeah, well, it was a really easy decision to make. When we sold Responsys, I was a single father and had two sons full time and I wasn’t doing a great job being a public company CEO and a single dad to be clear about it. And I thought most of my career, I’ve been focusing on that first one. And so it was an opportunity, a wonderful gift to be able to focus on the other while they were still home for they’d eventually go off to university. And it was probably the best four years in my life as an adult. And it was a wonderful time to be close with my boys, help them through some kind of really formative issues and trying to become young men and hopefully being able to put a little positive stamp on the kind of young men they become, which was great. And also they loved all the sports. They played soccer and lacrosse and sports I played it when I was in college, so I got to go to all their games and that was hugely rewarding. But in terms of what is a good decision, I mean, it was no question a good decision because I enjoyed it so much. I think it made me better when I came back to full time work. I think back to your empathy point—dramatically increased. One of the first things we did and I got the DocuSign was put in a six month parental leave program. And even though be clear, I was taking care of a much older child, I wasn’t doing the hard work that people have to do when you have a nine month old, as you do. But I thought, wow, I mean, I grew up with a single mom and I never had been aware of just sort of thinking about that. Like, this is so important. We need to support all of our parents in the States. So my empathy around issues like that dramatically improved. I think the last thing is it let me get comfortable that while I sort of used to define myself a lot around my professional success, I get comfortable to say, no, I’m just a person. And I’m Dan and I’m proud of who I want to be. I’d like to make changes and get better and a lot of things. And now when I get back into full time building company, it allowed me to even take my ego down to another level and say, it’s not about me, it’s not about me. It’s about the other people, whether it’s my kids or the company, other people’s careers. I can really focus and just get excited about driving the success in that front. So I’m a little more aggressive. I think I’m willing to take a few more chances. And because I don’t have to be afraid of failure, I’ve achieved what I want to achieve. And so now I want to help other people achieve what they’re going to achieve. And I go harder, so that I think from that standpoint, it was a huge, huge success for me. I encourage anyone that’s fortunate enough to have the opportunity to do full time, particularly dads. I know people don’t think it should be a mom thing, which is crazy. It’s like dad as much or more, I think, than Mom should be trying to figure out a way to really be focused on caregiving with their own kids.

Mathilde Collin My husband would love hearing this. We’re at the end of our time. Thank you so much. And I have so much energy and I learned so much. And I’m sure that everyone that will listen to this interview will learn a lot. Thank you. It is really inspiring.

Dan Springer All right. Thanks for having me.

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