World Reimagined

The Hardest Leadership Lesson to Learn: Interview with DocuSign (DOCU) CEO Dan Springer

Dan Springer, CEO of DocuSign

The Covid-19 pandemic has forced businesses of all kinds to rewrite their playbooks. Employee engagement and communication, customer service, supply chain management—it’s all been redefined in this new virtual environment. Central to this seismic shift is a new definition of leadership that is emerging. In this series, Nasdaq will be speaking with today’s leading CEOs about how they’re reimagining their role as they guide their organizations through this pandemic. We’ll see what that transformation looks like and how it is helping them prepare for the next normal.

Today, we’re hearing from Dan Springer, CEO of DocuSign (DOCU). In a pre-pandemic world, physical signatures were the norm. The move to an all-remote environment has driven the need for a virtual alternative and, as a result, DocuSign has soared. It provides the ability to sign everything from sensitive bank documents to medical release forms with a simple electronic signature. Over the past year, the San Francisco-based company has seen revenue grow nearly 50% and has added 2,000 new employees—all remotely. We spoke with Springer, 57, recently about how he’s staying connected with his remote workforce, the leadership lesson that’s been the hardest for him to learn, and his favorite questions during job interviews. Some excerpts from our interview:

You’re running a company that has done very well during the pandemic. Can you give us a sense of what the last year has been like for you?

Let’s just say I’m very happy to have 2020 in the rearview mirror. But I think the lessons will make us better. Working remotely has been a roller coaster of learning and one of the first things we all realized was that we could actually do it. I have to admit that I did not see the ability to have the productivity that we’ve had. We were growing in the solid 30% range before the pandemic, and we grew nearly 50% last year. It was a crazy productivity improvement and we did it while people were not with their colleagues.

There’s been enough time for companies to see what works better in-person and what's actually better remotely. Any surprises there?  

Every month we have a program called Discovering DocuSign. It’s for all the new employees and it gives them an introduction to our company and our values. We used to do that in person in Seattle where the company was founded. Now, it’s all remote. In the old days, I didn’t get to too many of these. Today, I make every one of these virtual events and I get to meet every single new employee. This is a perfect example of understanding the learnings of the pandemic in order to make things better when we do go back.

Can you talk a bit about the role of empathy in leadership? How do you define it?

The first part for me, which is often missed, is that you have to be a great listener. And even if you’re not naturally a good listener, which is kind of where I put myself, you have to force yourself to do it. You have to take the time. What did Woody Allen say—90% of success is showing up? Well, 90% of empathy is listening. And I spend a lot of time listening to folks, and trying to be interactive and build relationships.

What has been the hardest leadership lesson for you to learn and put into practice?

I think a lot of that depends on where you are in your own development as a leader. We’re all on a journey. When I was an early manager, my lessons were all about trying to stop proving that I was the smartest person in the room, and to try to make other people successful. Before I had children, I was an egotistical S.O.B some of the time. When I was 23, 24 and managing people my parents’ age, I did not have the sensitivity to understand how to relate. Those are things you learn along the way.

Has has this evolved throughout your career?

I have about 18 years of experience as a CEO if you count DocuSign and other companies I’ve led. The first half or so was trying to learn how to be a CEO. It really means being a general manager, being responsible for the whole entity. And then the second half—I would say the last eight or nine years—has been about understanding people, thinking about career development for other people, and what motivates them.

What does that look like in practical terms?

I used to think that everyone should be motivated the way I was, right? We have company goals, and here are the numbers, and we’re all going to go take the hill. And that is a huge part for many people. But I had to learn that people are motivated by different things. For some people, it really is about approval. It’s like they’re saying, ‘I want you to show me that I’m doing a good job.’ As a leader, it’s your responsibility to recognize that and then find ways to give them that win. There are other people that are motivated by money. They want career growth and financial freedom. We have this weird thing where we think we’re not supposed to say that—not supposed to say that we’re motivated by money. When I didn’t have a lot of money, I cared about having more money. That’s a normal thing. So I think a big part of this is meeting people where they are.

Are you looking for different traits in the folks you hire because of the pandemic?

Yes, skills are less important than I thought. Twenty years ago, especially during my days at McKinsey, skills were all that mattered. Now, I still think smart, skilled people are incredibly important, but once you have that, there are other things that need to be present in order to be successful. For managers, the ego needs to be suppressed so they can focus on the development of other people. I need each manager here to say that it is their mission to enable each employee at DocuSign to do the work of their lives. If you don’t feel some obsession, as a people leader, you’re missing something that we really need.

How do you uncover that in the people you’re looking to hire?

One of the questions I like to ask during the end of an interview is that if I had all your coworkers here from your last job, what would they tell me was great about you, and what would they say you had to work on? And what happens is that basically everyone falls into two answers for that last question. They answer, ‘I work too hard, I do more than my share.’ Or they say, ‘I micromanage sometimes.’ Well, most of us have those things to work on. But about 25% of the people will come back with good, thoughtful answers and explain specific things that they’re working on and how far into the journey they are. Those people have self-knowledge, and that’s so important. When I hear that kind of self-awareness, I just know they’re going to do great.

Rapid fire:

  • A fear that I’ve gotten over in the past year is: Believing that productivity and people development would suffer in a pandemic because people need to be physically together for the magic of innovation to happen.
  • A strength I’ve gained is: Empathy to better listen to, engage with, and understand colleagues as we all continue to tackle unique challenges.
  • A skill that I’m working on is: The pandemic has made me realize how much I crave human interaction and in-person collaboration, but I’m staying (relatively) patient and flexible until we can soon return to a sense of normalcy.

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

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Susan Caminiti

Susan is a writer and senior editor whose work covers a wide range of business and social topics including corporate profiles, personal investing, entrepreneurship, health and wellness, work/life issues, and wealth management for both editorial and corporate clients. She is a former staff writer for Fortune magazine and her work appears in Fortune,, and in a variety of other print magazines.

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