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12 management classes from Dan Springer, CEO of DocuSign

18, 2020

7 min read

The opinions expressed by the entrepreneur's contributors are their own.

In the ongoing series from Comparably in collaboration with Entrepreneur, If I Knew Then: Leadership Lessons, I hold virtual fireside chats with top-class CEOs of major brands from Nextdoor and Blue Apron to Waze and Warby Parker. As a host, I ask talented leaders to share some of the valuable lessons and practical career advice they have learned during their careers. Available as a source of inspiration for current and future entrepreneurs, these rare, honest glimpses into the lives of notable catalysts for success in the business world should not be missed. When CEOs get transparent, they can't help but lean on.

For the last episode, I sat down with DocuSign CEO Dan Springer, who leads thousands of employees worldwide and enables DocuSign to modernize organizations by making every agreement 100 percent digitized. Fostering innovation and growth in technology and the Software-as-a-Service (SaaS) industry is an example of Springer's leadership and experience over the past 25 years. Prior to DocuSign, the Harvard MBA graduate was Chairman and CEO of Responsys for a decade, where he revolutionized and grew the business from a private startup to a leading cross-channel global marketing automation platform. This led Oracle to purchase $ 1.6 billion worth of Responsys in 2013.

A veteran of Silicon Valley, Springer is both the Bay Area's most admired CEO and the best CEO. He was awarded the 2020 Robert F. Kennedy Prize for the Ripple of Hope for Human Rights, and shares that award with leading US infectious disease expert, Dr. Anthony Fauci, as well as Colin Kaepernick from San Francisco from 49 for his leadership role in the area of ​​social change during these difficult times. Barack Obama, Hillary Clinton, Bono and the late Representative John Lewis also received this award, catapulting Springer into the society of greatness.

This conversation covers, among other things, Springer's genesis – from "winning the ovary lottery" to attending the famous Lakeside High School with alumni like Bill Gates and Paul Allen – and lays the foundation for his early life before he becomes a serial entrepreneur. Here are the 12 most important takeaways from our chat:

1. Successful leaders don't all come from the same mold

Everyone has a different background and life path; Use that to move you forward. Springer shares that he grew up with a single mother in an affluent suburb, which may have given him a chip on his shoulder early in his career at McKinsey. However, he turned this initial uncertainty into something positive by surpassing and exceeding it.

2. Use mistakes to push you to do better

Springer explains the concept of grit and the notion that surviving a small mistake pushes you to do better. Failure pushed him that way, and he often thought I would keep trying to fight my way through and not let the experience define me.

3. There is an element of chance in all of our careers

When he looks at each of the things he's done, Springer admits that he only gets a third of them to develop the way he wants: “I think you have to be in a position that lets you accept both happiness and happiness. Unhappiness will get in your way. You can't get overly down or up and complacent. You have to have this energy to keep charging. "

4. A great leader knows how to play out people's strengths and bring people together

Know how to bring people together. For example, sometimes the innate qualities of people who have fun and avoid conflict are of tremendous value. Springer used these positive qualities to build teams: "I always tried to get everyone to work well together."

5. Humility makes you a better leader

Accepting that there is always room for improvement is key to being a great manager of people. Springer says that a healthy respect for your peers in an ecosystem is the future of leadership rather than hard charging via your ego.

6. There is a three-part formula for rating people

To calculate this, take your intelligence and strengths or "S", divide that by your ego or "E" and then increase this to the strength of how hard you work. "If my ego gets too high, the other components are wiped out," says Springer. "You can improve some of your skills over time, but your ego and hard work are part of this formula that you can control – and mastering what you can control has a huge impact."

7. It pays to be at the top of your game to stay home

Springer talks about the opportunity to focus on being a single father to his two young sons after selling his previous company. He recalls that at the top of his game he stopped focusing on fatherhood as one of his best personal and professional decisions. "Men should choose parenting rather than work rather than pressure on women to do so."

8. Empathy is the key to success as a citizen

Springer taught his sons a great lesson when he told them that when they help others in life they will be happier in the long run: “We are very committed to the Boys and Girls Club. We select organizations that we really want to leave behind with our focus and time that goes beyond our money. "

9. Be a servant leader and take an interest in making your co-workers successful

When Springer returned to the workforce after a four-year hiatus to raise his sons, he found he had failed to help young people develop their careers. He is a firm believer in leading servants and prioritizes staff success. By embracing all points of view and focusing on the professional development of staff, a servant leader can instill more trust and loyalty within the organization.

10. Hire smart people with expertise and let them drive

Nobody can be an expert on everything. Be aware when you are overwhelmed in a particular area and trust to hire people with that expertise and then let them drive you. "We don't hire smart people and tell them what to do. We hire people who are smart so we don't have to tell them what to do," says Springer.

11. Knowing exactly how you are spending your time is important

Knowing when and when you won't need those extra hours in the office is critical. Springer admits that he was notoriously one of the people who felt fulfilled when he crossed things off his to-do list. He would spend hours doing things that were just reactions to people and not necessarily time for big strategic thinking. He suggests that we pick and choose when to show up and deliver, and when to sneak away to play with our kids.

12. Get rid of the little things so you can focus on the big ones

An example of this is getting everything out of your email inbox before you go to bed. "If I can't put it on a yellow glue, it's too complicated," says Springer. “I tell people that if we have a 45 minute meeting I want to see the slides the night before. This type of discipline makes everyone more productive, and without focus and attention we cannot solve problems well. "

Check out the full webinar for more insight from this incredible leader.

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