12 Leadership Lessons from DocuSign CEO Dan Springer

by Jason Nazar

In Comparably’s ongoing series in partnership with Entrepreneur, If I Knew Then: , I host virtual fireside chats with high-profile CEOs of major brands from, Nextdoor and Blue Apron, to Waze and Warby Parker. As the host, I ask talented leaders to share some of the valuable lessons and practical career advice they learned during their career trajectory. These rare, candid insights into the lives of remarkable catalysts for success in the business world are accessible as a resource of inspiration for current and future entrepreneurs and are not to be missed. When CEOs get transparent, you can’t help but lean in.

For the latest episode, I sat down with Dan Springer, CEO of DocuSign, who leads thousands of employees globally, allowing DocuSign to modernize organizations by making every agreement 100 percent digital. Driving and growth in technology and the Software-as-a-Service (SaaS) industry exemplifies Springer’s executive leadership and experience for the past 25 years. Prior to DocuSign, the Harvard MBA graduate served as chairman and CEO at Responsys for a decade, where he revolutionized and grew the business from a private startup to a leading cross-channel global marketing automation platform — resulting in Oracle’s $1.6 billion purchase of Responsys in 2013.

As a veteran of , Springer holds honors as both the Bay Area’s Most Admired CEO and Best CEO. He is also a 2020 recipient of the Robert F. Kennedy Human Rights Ripple of Hope Award, sharing this accolade alongside top U.S. infectious disease expert, Dr. Anthony Fauci, as well as San Francisco 49ers Colin Kaepernick, for his leadership on social change during these trying times. , , Bono, and the late Representative John Lewis have also received this award, catapulting Springer into the company of greatness.

Among other topics, this conversation covers Springer’s origin story — from “winning the ovarian lottery” to attending the famous Lakeside High School with alumni such as Bill Gates and Paul Allen — laying the foundation for his early life before becoming a serial entrepreneur. Here are the 12 essential takeaways from our chat:

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

Everyone has a different background and path in life; use that to propel you forward. Springer shares that he grew up with a single mom in an affluent suburb, which might have given him a chip on his shoulder in the early part of his career at McKinsey. However, he turned that initial insecurity into something positive by excelling and overachieving. Continue reading

Managing the COVID stress crisis with finesse, compassion

By: Tracey Ferstler

With the pandemic causing new anxieties, employers need to rethink their benefits to provide a better mix of tools for managing stress, burnout and depression.

Everyone faces stress in their life, but the ripple effect of COVID-19 has caused new sources of financial, social and physical stress that go far beyond the norm. These stressors are lasting and pervasive, piling up to the point where they pose a significant threat to employee well being if left ignored.

According to a new MetLife mental health study, employees say that their top stressors are financial issues (81%), job insecurity (77%), fear of catching the virus (60%) and social distancing (47%), followed by concerns about the presidential election, social justice issues and not having access to healthcare because of COVID-19. On top of this, separation of work/home life is increasingly blurring, especially for parents trying to juggle children at home.

Never before have employees had to cope with so much at one time, and never before have benefits programs been tested across the spectrum of holistic health, including physical, financial, mental and social health. Per the study, nine in 10 employers say their organization is not completely ready for a mental health crisis, although one in five say the United States is in crisis right now.

This is the perfect opportunity for employers to rethink their benefits approach to provide a better mix of tools for managing stress, burnout and depression. This will not only help employees become more resilient and productive, but will also improve long-term business recovery.

Start with understanding key stressors

Anxiety is at an all-time high, with 5.5 million employees saying they no longer feel mentally healthy and 38% of adults reporting symptoms of anxiety or depressive disorders, an increase of 27% since 2019 (pre-pandemic). In addition, 41% of employees say they feel stressed, burned out or depressed at work on a regular basis.

Financial stress is the No. 1 driver of overall mental health stress, up 29% since 2019. The biggest sources of financial stress rest in concerns about long-term savings and medical bills/expenses followed by fears about stock market volatility and retirement plans.

These concerns, combined with all the other top stressors listed above, are creating a workforce at the tipping point. This is compounded by the fact that not everyone can “self-diagnose” the warning signs of mental health. When asked, employees don’t always think they have a problem but say they have specific symptoms. Most employees report at least five key signs of burnout—such as feeling emotionally and physically drained—and at least five signs of depression, such as feeling tired, hopeless or unable to sleep.

Next, create an environment of support

As they plan for business recovery, 76% of employers say resilience is very important. Compared to least-resilient employees, those who are most resilient have better mental health, are more likely to be holistically well, and are less likely to be burned out or stressed.

To help return employees to good health, benefits plans should try to span every area of holistic health since financial, mental, physical and social health are interrelated. Organizational support tools can include effective tools like employee assistance programs that offer everything from financial consultations; to counseling for stress management, work/life and substance abuse; to childcare and legal support. Employees with EAP access show 17% more resilience than employees without EAPs.

Insurance programs (like life, disability, hospital indemnity, critical illness) may also help employees boost financial security.

It is one thing to offer the right mix of tools, yet quite another to create an open culture that makes mental health a priority. This culture also should build awareness about available resources, educate employees about the warning signs and remove the stigma of asking for help.

The ability of employers to manage the looming mental health crisis with finesse and compassion can only help drive loyalty, productivity and long-term success.

Source: Human Resource Executive

Human After All: Organizational Change’s Critical People Factor

Creating the right organizational chart is just the first step. Behavior change must follow.

Why do companies change their operating model? Often they wish to become more agile. Sometimes they hope to increase collaboration. Almost always it has something to do with behavior. But as the overhaul gets underway, facts and data become the focus instead. And by the time organizational charts are drawn up, rolled out to teams and explained, management is exhausted.

Then someone remembers: We did all this to change how our people act. Oh, and those people are worried. Worried the changes aren’t good for them and that they are going to lose some of their power.

In the end, organizations don’t change, people do. And that tired management team still has a lot of work to do.

Cognitive biases’ role in organizational change

Behavioral science teaches that change triggers biases in the way humans process information and perceive threats. We are averse to loss, fear losing control and tend to view everything as a zero-sum game. We perceive losses more acutely than we anticipate gains. It’s quite natural, then, that any new organizational structure immediately sends employees into an examination of their position relative to peers. The new org chart becomes a scorecard: Some people are winning, others are losing.

Even when we understand intellectually that change is for the greater good, we balk when it diminishes our personal authority. One CEO broke down these tendencies by using a sports metaphor. “We’ve been operating like a golf team,” he said, “but now we have to play basketball.”

Metaphors can be clarifying for businesses in transition. Think of moving from a swim team to water polo, from track to soccer, from instrumental soloist to a jazz band, or even from stand-up comedy to membership in an improv troupe. In each case, strong individual performers shift from an environment that tracks and rewards independent effort to one of interdependence, in which success is determined by cooperation.

This CEO’s company still needed and appreciated great talent, as the metaphor helped make clear, but everyone needed to accept the critical importance of contributing to the team.

Anticipating the tough moments critical to organizational change

For any company to reap the full value of an organizational overhaul, its people will need to behave differently than they did in the old system. If they fall back to their old ways of working, the value will be lost.

Transforming behavior requires focusing on a few critical moments during which people will choose either the new behavior or their old habit. These moments of truth can be predicted and planned for. Leading companies do this early in the process, working with employees to anticipate the tricky moments and then ensuring everything from streamlined reports to employee support is in place to encourage adoption of the new way of working.

When a global consumer products company recently updated its operating model, one of the organizational changes was to bring all digital marketing into a centralized marketing department. It was simply too expensive for each business unit to build its own digital capability. This is quite consistent with the direction many organizations are headed today as they look for ways to build interdependencies and move away from autonomous silos. But it can lead to feelings of losing power and control, especially at the business unit level, where marketers now must turn to the center on digital topics.

The company’s executives and staff carefully anticipated which issues were likely to create discord between the business units and the center, talked them over, and decided how they would address them. Business unit heads understood that the solution rested in their hands: By modeling collaboration with the center, they would set the example for staff to do the same in their own work.

It emerged that the moment of truth for the business unit heads would be when they were asked to referee a disagreement between their team and the central digital team. Would they always side with their team against the center, or would they try to find a constructive solution?

To support choosing the constructive solution, the company created feedback loops that ran the duration of the transition. In that feedback, executives sought not only information about how the process was going but also what they themselves could do better. Over time, a pattern emerged in the data. Leaders who learned from this upward feedback and improved were rewarded with strong increases in employee engagement.

Moving forward

In the New York City Marathon, there is a hill at the 15-mile (24-kilometer) mark—the crossing of the East River from Queens to Manhattan over the 59th Street Bridge. It’s one of the greatest challenges of the race, but as runners finish their descent and head north up First Avenue, they know that 11 more miles (18 kilometers) remain.

For executives who have put months into studying what functions their organization needs, how it will be organized, and who reports to whom, it may be hard to accept that they have only finished the first leg of the race. There are many hard miles yet to go, and getting to the finish line depends on helping the humans in the organization change their behavior, too.

Source: Bain

Continue reading

‘Be Human’: Marshall Goldsmith’s Best Leadership Advice Right Now

In any time but the current one, this is the last place Marshall Goldsmith, one of the most in-demand CEO coaches in the world and bestselling author of leadership classics like What Got You Here Won’t Get You There and Triggers, would be. Back in B.C.—Before Covid—Goldsmith was a legendary road warrior with 11 million frequent flier miles, tracking how many nights a year he was at home with his family, rather than vice versa, in the hopes of improving that KPI.

Yet, here he is, with a green screen behind him, chunky Sony earphones locked on snuggly, ready to talk from his home in Covid-subdued La Jolla, California. And, as you’d expect from someone who is obsessed with prepping leaders for change, he’s okay with it. “I’m a Buddhist,” he shrugs. “What is is, so you just make peace with what is and do the best you can and move on.”

This kind of equanimity takes work, of course. Lots of it. In the midst of crisis, Goldsmith is practicing what he preaches, meeting with a group of 50 or so high-performing people each weekend (virtually, of course), talking about issues, feelings—and fears. He’s working with his own coach, trying to improve his behaviors, checking in nightly on how he’s doing relative to expectations. And, more than anything else, he’s listening and trying to help his clients—many of whom are household names in global business—tackle a very, very tough time.

In a conversation with Chief Executive, Goldsmith, who will be the keynote speaker at our upcoming annual CEO Leadership Conference on November 5, talked about how Covid is disrupting his clients, what he’s counseling them and why this period of unparalleled change and challenge is an essential time to work on your own behavior and improve your emotional intelligence. The conversation was edited for length and clarity. Continue reading

Hiring in 2020

Recruiting and interviewing during the COVID-19 crisis with the stay-at-home order, remote interviewing has become a requirement, not a luxury. Tech tools for hiring such as Zoom, Skype and Go-to-Meeting, have been a boon to remote job interviews. Seeing the candidate is so much better than just interviewing them by phone. However, remote interviews can be more troublesome than in-person interviews.

We had the opportunity to tap into our network of professionals on both the corporate side (looking to hire the talent) and candidate side (the talent for new opportunities) to get their input and thoughts around new issues and processes that they have encountered – and how to improve the remote interview experience.

From the corporate side:

  • You want to show all potential candidates that just because the interview is remote, it is no less professional than if you were to meet face-to-face.
  • Introduce your company culture; your candidates might not have the opportunity to see your office and meet your team. Or maybe you don’t even have an office. So make sure candidates don’t miss out on finding out all about you.
  • Communicate the interview details when remote interviewing.  It is better to over-communicate: this may be your hundredth remote interview, but for the candidate it might be their first and the tools you’re using might be new to them.

From the candidate side:

  • Get to know your video platform beforehand. These days, a lot of different video platforms require a myriad of account sign-ups, app downloads, or permissions on your device.
  • Don’t just dress for where the camera can see. Professional dress codes are expected in video interviews. The best way to guarantee your confidence and seriousness in the conversation is to dress the part.
  • Hiring managers are drawn to candidates that show up curious, so come prepared with a list of questions that will prove you’ve done your research.
  • Control your environment. In addition to properly preparing for your job interview, you have the added challenge of preparing the right space within your home for this important meeting. Find a spot in your home that’s quiet, clutter-free, and well-lit. Download any necessary software or updates ahead of time and test the equipment with a friend to ensure your lighting, audio volume, and the positioning of your camera is just right.