7 lessons on low-ego leadership from DocuSign CEO Dan Springer

DocuSign CEO Dan Springer admits he wasn't always the best manager. He shared his learnings over 25 years as a CEO and how he developed skills as an empathetic and impactful leader.

Nick Darlington, Writer
2 July 20219 Min Read

DocuSign CEO Dan Springer admits he wasn't always the best manager. He shared his learnings over 25 years as a CEO and how he developed skills as an empathetic and impactful leader.

For some leaders, success is accompanied by self-importance and an overinflated ego. This heightened sense of self reveals itself in many ways. Sometimes, it’s obvious. Think of leaders who only believe their opinions, disregarding what others say. Other times, it’s more subtle. Think of leaders who work from a corner office because it’s the norm, and rarely interact with employees.

Regardless of how it reveals itself, big-ego leadership causes a disconnect between employees and leaders, with decisions often being made in a vacuum. A disconnect like this means leaders never really have their pulse on how their employees are feeling. How can leaders hope to lead when this is the case? Decisions made in a vacuum are also often not in the best interest of the company.

The solution? Low-ego leadership or empathetic leadership that involves putting the organization and customers first. It’s a leadership style that we at Front value highly and is embodied by DocuSign CEO Dan Springer.  

We decided to speak to Dan to get his key lessons on the topic—and how leaders can become more impactful and empathetic. Here are seven key takeaways.

1. Set high expectations for low-ego leadership. 

Dan recommends that leaders set high expectations for their managers who want to become better leaders. Managers need to work every day to ensure that it’s the best place their employees have ever worked.

Dan admits that managers won’t always get it right but if you don’t set the bar high, you “give people an excuse to not be great managers.”

2. The ego is a fully controllable element of successful leadership.

When Dan evaluates leaders or interviews people for positions at DocuSign, he typically looks for three factors: 

  • Whether people have the skills to be successful at their job

  • Whether people can manage their ego so they can focus on the team’s results instead of their own

  • How hard they work 

“To some extent, you can get smarter, and you can develop more skills,” explains Dan. “But we’re all given a certain level of capabilities. Once you have that, the parts you can really control are how you manage your ego and how hard you work.” And so, for those who want to improve, Dan suggests they focus on the controllable elements.

3. Low-ego leadership requires empathy.

Just like some people are more naturally skilled than others, some are more empathetic. That doesn’t mean you can’t cultivate empathy.

It’s just crucial to remember that “everyone is different in how they build their capability and awareness,” explains Dan. What works for you or Dan won’t necessarily work for someone else. 

That being said, Dan does recommend a few ways to build empathy based on his personal experience:

  • Have children. This teaches you to “love somewhere more than you love yourself,” explains Dan. Some people may already have the capability to love, and not everyone wants children. It may not even be an option for some or even make financial sense. But, in Dan’s case, it was.

  • “Encourage the people around you that really care about you to give you feedback, particularly when you miss stuff and on your insensitivities.” Dan goes on to explain that you also need to be open to that feedback and act on it. If you don’t, people will stop giving it to you. 

Speaking of feedback...

4. Feedback is a gift—the secret power that helps you overcome your ego issues.

When it comes to becoming a better low-ego leader, Dan believes in direct and constant constructive feedback. “You need to be able to explain to people why they’re 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.’”

For Dan, this feedback is the only way you can really help people. “It’s not about book learning. I mean, you can read stories, but it’s really about that intense personal development.”

Some people may find it hard to stomach the feedback at first and even apply it, but that’s why you need to build an environment that encourages it. For example, at Front, we have a meeting once a week where employees can share their stumbles (or mistakes) of the week openly with others. 

This feedback process encourages people to become comfortable with not being the smartest person in the room. It builds humility, which is “the secret power that allows you to overcome your ego issues—to get comfortable with your own challenges and your own shortcomings,” says Dan.

5. Empathetic leadership requires more than just hard work. You need awareness and focus.

“Sometimes it’s [low-ego leadership] easy for people. Some people naturally have high EQs. Their personality is to be supportive of other people. They get their joy watching people develop, so it’s easy for them to do it—and for some people, it’s really, really difficult.”

In Dan’s case, it was initially quite hard. He vividly recalls being a young 23-year-old focused on himself and his career. He was very competitive and ambitious and wasn’t great at putting people first. He also openly admits to not being a great manager.

I had some early management jobs where I wasn’t very good as a manager and was very sensitive. I was managing people much older than I was. I just didn’t have an awareness of how to do that well.

Through work, but mainly through developing awareness (via feedback) and focus over time, he became a more empathetic leader. 

To encourage other leaders to achieve this, he shares stories of leaders and their shortcomings (including his own) and how they overcome them through awareness and focus. He’s also a strong proponent of management training around inclusivity and diversity and aggressively driving education around these topics.

6. Education and training around inclusivity and diversity are needed to help build awareness and sensitivity.

Dan says it’s naive to think people who are good at their jobs will suddenly be great managers to those who are different from them. 

Companies need to train employees to be more aware of those differences so they can become better managers to those individuals. Companies can use surveys to get feedback from employees to identify areas a manager is doing really well in and areas they can improve upon. 

Dan also recommends you avoid offering diversity or inclusion training separately. Instead, integrate it into other managerial training programs, so people are more open to it.

“I think it’s more effective,” explains Dan. “It also takes away some of the cynicism because people do come into diversity training with their guard up, saying, ‘Well, you know, I’m not racist.’ That’s not a constructive way to start the communication, but you understand why people would be offended.”

Communication is also crucial, as Dan highlights with his experience at DocuSign. “At DocuSign, we started off with communication. We have to be able to talk about these things. We have a very good, transparent environment. People can ask the really tough, aggressive questions. That pushes the rest of our leadership and me to say, ‘We need to address the things that are on our employees’ minds.’”

Related resource: Set your team up for success with our guide to strong internal communication.

Finally, because what gets measured gets managed, organizations would do well to set diversity goals and publicly publish their success against these goals to assess progress and ensure accountability.

DocuSign has seen a significant improvement in the diversity of its workforce due to this approach, but Dan acknowledges they still have a long way to go.

7. To become an empathetic leader, you need to get to know and connect with your employees, especially during tough times.

Dan, who gets his energy from people, takes a lot of time to get to know his employees because he believes it’s crucial for a good job experience. It also helps him keep a pulse on how employees and, in turn, the company is doing, so he can lead better. 

Dan told us how incredibly hard it’s been because he’s been unable to connect with people like he used to because of the pandemic. As a result, DocuSign has had to adjust its approach. They started having town hall meetings (where Dan speaks and answers questions to help fill the leadership void) and more informal meetings like trivia contests and happy hours with groups. 

While Dan cannot attend all team meetings, he has dramatically increased his attendance (even if it’s for ten minutes) because he wants to and has so much more capacity now that he’s flying less. 

However, one silver lining of the pandemic is that he can now attend all “Discover DocuSign” meetings, virtually. This is a meeting all new employees are flown out to attend in Seattle to chat to Dan and learn more about the company and its values. 

Dan makes it clear at the end of those meetings that any employee can call or email him if they’re unsure how their job connects to the company’s values or they just generally feel lost and aren’t getting the answers from managers.

Related reading: 3 Inspiring reads on leading a remote team with trust.

The point is: To truly become a low-ego leader, you need to connect with staff beyond simple “hellos.” Look to see how often this is happening (maybe it’s not happening enough).  

Next, carve out time to connect and implement creative ways to do so, just like Dan and the team at DocuSign did. For example, maybe you can have monthly check-ins with departments across your organization. 

These ways don’t have to take up a lot of time, be mind-blowing or even be out of this world; they just need to be a tool to help you achieve your primary goal of fostering connection for the betterment of your people and the company.

The bottom line

Low-ego leadership is about putting your people and company first over yourself. For some, becoming an empathetic leader is easy. For others, it requires more work. 

Regardless of your situation, you can become a better leader. Just take one small step daily—and use these lessons from Dan to guide you along the way.

Written by Nick Darlington
Originally Published: 7 July 2021
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