If you’ve ever dropped the ball at work, you’re in good company.
Everyone makes mistakes — even the people at the top.
This month, I asked three CEOs from a range of industries about the biggest mistakes they’ve made.
They spoke of broad themes in their careers, rather than single instances, and shared how these lessons changed their overall approach to their jobs.
Read on to learn about the moments they messed up:
Cato Networks CEO, Shlomo Kramer
Photoset
Serial entrepreneur and Cato Networks CEO Shlomo Kramer has invested in over 30 companies, including Palo Alto Networks and Gong. He said that one of the biggest mistakes he’s made is “getting excited about things” he doesn’t understand and investing in areas outside of his expertise in cyber.
As someone who’s curious about many sectors, Kramer said he’s ventured into areas like AI-based marketing or fintech.
“It’s much easier to get excited about things you don’t understand,” Kramer said, adding that a deep understanding of a topic “gives you granularity,” which may be less exciting.
Invisible Technologies CEO, Matt Fitzpatrick
Victoria Dawe
The CEO of Invisible Technologies, Matt Fitzpatrick, said he doesn’t believe in mistakes. He believes in making decisions and learning from how they play out.
“I have this weird view that you don’t make mistakes; you just make decisions, and then you figure out what you learn from those decisions, and then you course correct,” said Fitzpatrick.
For example, earlier in his career, Fitzpatrick was starting out in the investing industry and had two private equity offers. He said one of the companies was the wrong choice by any traditional metric, but he decided to go with it because he liked the team, and the firm’s startup feel.
That ended up being the wrong choice, and the company that he turned down went on to become “incredibly successful,” he said. Making that decision had its own benefit though because it led him toward the technology sector, Fitzpatrick said.
If he really felt like it was a mistake, Fitzpatrick said he would’ve found another way into the investing sector. By making the wrong choice, though, he had him time to reflect and decided to shift toward tech.
“Most people don’t reevaluate what they’re doing until they’re given an impetus to do so,” Fitzpatrick said, adding that making the “wrong” decision can be valuable if it causes you to rethink if you’re on the right track or if you need to change something.
The Knot CEO, Raina Moskowitz
The Knot
The CEO of wedding brand The Knot, Raina Moskowitz, said her biggest career mistake is not trusting her gut enough.
“I’m learning to operate with more and more conviction,” Moskowitz said.
She said when it comes to hiring decisions, she said she’s sometimes focused too much on the candidate’s skillset, but hasn’t taken into account how excited or passionate they are.
“You need that balance,” Moskowitz said. “That’s why I feel so strong about it going forward.”
The CEO said that someone could be talented at their job, but not excited enough to be on the team. She said she wants to work for a company whose mission she’s excited about every day, because that will ensure that she’s motivated to make the team successful. The same applies to those she hires, she said.
The lesson is top of mind for Moskowitz as she builds out her “executive dream team,” she said. Since joining the brand about a year ago, Moskowitz said she has hired a new chief product officer, chief technology officer, chief financial officer, and a new EVP of commerce and consumer experiences.
