• February 1, 2023

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

T.The Covid-19 pandemic has forced companies of all kinds to rewrite their game books. Employee engagement and communication, customer service, supply chain management – everything has been redefined in this new virtual environment. At the center of this seismic shift is a new definition of leadership that is emerging. In this series, Nasdaq will talk to today’s top CEOs about how they are redefining their roles as they lead their organizations through this pandemic. We will see what this transformation looks like and how it helps them prepare for the next normal.

Today we hear from Dan Springer, CEO of DocuSign (DOCUMENTARY). In a pre-pandemic world, physical signatures were the norm. The move to an all-remote environment has increased the need for a virtual alternative, and as a result, DocuSign has grown dramatically. It offers the ability to sign everything from sensitive bank documents to medical clearance forms with a simple electronic signature. Over the past year, the San Francisco-based company saw sales grow nearly 50% and hired 2,000 new employees – all remotely. We recently spoke to the 57-year-old Springer about how he stays in touch with his remote workforce, which leadership lesson was the most difficult for him to learn, and which questions he liked most in interviews. Some excerpts from our interview:

You run a company that has done very well during the pandemic. Can you give us an impression of how the last year has been 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 was a roller coaster ride of learning and one of the first things we all realized was that we could actually do it. I have to admit, I didn’t see the ability to have the productivity that we had. We grew in the solid 30% range before the pandemic, and we grew nearly 50% last year. It was a crazy productivity boost and we did it while people were away from their co-workers.

Companies have had enough time to see what works better in person and what is actually better remotely. Any surprises there?

Every month we have a program called Discovering DocuSign. It is for all new employees and gives them an introduction to our company and our values. We did that personally in Seattle, where the company was founded. Everything is far away now. I didn’t get too many of these before. Today I do each of these virtual events and get to know every single new employee. This is a perfect example of understanding the insights of the pandemic to make things better when we return.

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

The first part for me that is often overlooked is that you have to be a great listener. And even if you are not naturally a good listener, as I imagine, you have to force yourself to be. You have to take the time. What did Woody Allen say – 90% of success shows up? Well, 90% of empathy is listening. And I spend a lot of time listening to people and trying to be interactive and build relationships.

What was the hardest leadership lesson you could learn and put into practice for you?

I think a lot of it depends on where you are in your own leadership development. We are all on a journey. When I was an early manager, my class was about stopping proving that I was the smartest person in the room and making other people successful. Before I had kids, I was a selfish SOB at times. When I was 23, 24 years old, dealing with my parents’ age, I didn’t have the sensitivity to understand how to act. These are things you will learn along the way.

Has this evolved over the course of your career?

I have roughly 18 years of experience as CEO if you include DocuSign and other companies I’ve run. The first half tried to learn how to be a CEO. It really means being a general manager and being responsible for the whole company. The second half – I would say the last eight or nine years – was about understanding people, thinking about other people’s careers and what motivates them.

How does that work in practice?

I used to think everyone should be as motivated as I was, right? We have business goals, and here are the numbers, and we’re all going to take the mountain. And that’s a big part of a lot of people. But I had to learn that people are motivated by different things. For some people, it’s really about consent. It’s like saying, “I want you to show me I’m doing a good job.” As a leader, it is your responsibility to recognize this and then find ways to bring them victory. There are other people who are motivated by money. You want professional growth and financial freedom. We have this weird thing about which we think we shouldn’t say that – not say that we are motivated by money. When I didn’t have a lot of money, it was important to me to have more money. It’s a normal thing. I think a big part of it is meeting people where they are.

Are you looking for different traits in the people 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. I still think that smart and skilled people are incredibly important, but when you have that, other things must be there to be successful. For managers, the ego needs to be suppressed so that they can focus on developing other people. Every manager here has to say that their mission is to give every DocuSign employee the work of their life. If you are not obsessed with being a popular leader, you are missing something that we really need.

How do you find out about the people you want to hire?

One of the questions I like to ask at the end of an interview is if I had all of your staff from your last job here, what would they tell me was great about you and what would they say you had to work on it? And what happens is that basically everyone falls into two answers to that last question. They answer: “I work too hard, I do more than my part.” Or they say, “I’m a micromanager sometimes.” Well, most of us have these things to deal with. But about 25% of people will come back with good, thoughtful answers explaining certain things that they are working on and how far in the journey they are. These people have knowledge of themselves and that is so important. When I hear that kind of confidence all I know is that they’ll do great.

Rapid fire:

  • One fear I have overcome over the past year is: Believing that productivity and employee development would suffer from a pandemic because people need to be physically together for the magic of innovation to take place.
  • One strength I have gained is: Empathy, better listening to, connecting with and understanding colleagues as we all continue to face unique challenges.
  • One skill I am working on is: The pandemic made me realize how much I crave human interaction and personal collaboration, but I will remain (relatively) patient and flexible until we can soon return to a sense of normalcy.

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

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