6 CEOs on the most unexpected lessons they learned in 2020

Like everyone else, executives took away a few surprising realizations from 2020.

6 CEOs on the most unexpected lessons they learned in 2020
[Source image: sunstock/iStock]

Amid the chaos, changes, and profound losses of 2020, there was a lot to learn. Last year inspired many of us to make discoveries—business leaders and executives included.


We spoke with six CEOs on the unexpected lessons they’re taking into the new year. For many leaders, this year offered a new perspective on what is most important to their companies, to themselves, and to those who work under them. Some of these lessons surprised, and many fortified them for the year ahead. These quotes have been edited for length and clarity.

1. Dan Springer, CEO of DocuSign

I am much more of an extrovert than I realized. It has been difficult for me to not see my colleagues in the office on a daily basis or to meet in person our new employees. I’ve learned to take more time to recreate my typical interactions virtually to make up for this.”

2. Jeff Maggioncalda, CEO of Coursera

“I’ve learned how productive remote working can be, and how it has fundamentally changed how Coursera works. We’ll never go back. Before the pandemic, I thought in-person collaboration was crucial for innovation and agility. Remote work is a great equalizer, minimizing the impact of how you look, what you wear, and where you sit. While there is still a critical value for in-person communication, tools like Zoom and Google Docs enable us to meet face-to-face and work collaboratively on shared documents, and many employees enjoy the increased flexibility that comes with virtual work. Remote work is here to stay, and I look forward to building a more robust virtual workforce at Coursera beyond the pandemic.”

3. Julie Bornstein, CEO of The Yes

“I learned that adults don’t go to work just to work. We don’t send our kids to school just to learn. And people don’t go to restaurants just to eat. Human interaction is essential for our well-being, even if technology has advanced to a place where we don’t technically need to go places.”

4. Joel Flory, CEO of VSCO

“This year has been such a test of patience and resilience. Even as someone who believes there’s a lesson in every hardship or challenge, this year has been one for the books. There were weeks that felt like one long day, one Zoom call after the next. Nothing brings me more joy than to share a meal with someone to talk business or fun, and not being able to do this in person felt jarring and awkward. But we still showed up. Every day, we showed up. Our resilience is what I will remember most about 2020.

My 2021 focus is to build deeper connections with VSCO members and the people I care about. It is these deep connections that helped me get through this past year and it is one I want to invest in even more this new year.”


5. Enrico Frezza, CEO of Peace Out Skincare

“My first company is Peace Out, and the first time I’ve been the boss of more than 20 people. Before the pandemic, I thought I knew the power of teamwork. When COVID-19 hit, the team came together at warp speed to build and execute an entirely new strategy for every area of our business.

To watch the team develop and implement the new game plan—and then to experience the amazing growth cycle as a result—I realized that what I’d read in books was true: The foundation for the success of any company lies in its teamwork.”

6. Priscilla Tsai, CEO of Cocokind

“We need to have a backup for the backup! We’ve always been a company that has adapted well to change, but this year showed us that circumstances can drastically change overnight, so we need to be more prepared with backup plans to our backup plans.”

About the author

Diana is an assistant editor for Fast Company's Work Life section. Previously, she was an editor at Vice and an editorial assistant at Entrepreneur