Some were born to lead. But many are just “accidental managers.” Take Dustin Moskovitz. The millennial cofounded Facebook with his Harvard roommate, Mark Zuckerberg, and went on to become the company’s first CTO before leaving to found Asana, a project management platform, in 2008.
Again, Moskovitz led the startup (this time as CEO), taking the company public in September 2020 and growing it into the $3 billion company it is today, before stepping down last year. But looking back, he admitted the top job was never really for him.
“I just found it quite exhausting,” Moskovitz told Stratechery in a 2025, adding he’s really an introvert.
“I don’t like to manage teams,” he admitted, adding it was never his intention to do so—even after founding his second startup, Asana, with Justin Rosenstein. “I’d intended to be more of an independent or head of engineering… Then one thing led to another and I was CEO for 13 years.”
The result? Having to “put on this face day after day,” he said.
The CEO hoped putting on a mask would get easier as the company scaled and he could delegate more to focus on actually running the company from behind the scenes, but actually the opposite was true.
“The world just kept getting more chaotic—the first Trump presidency and the pandemic and all the race stuff—it made it just a lot less of the company building, being a CEO is a lot more reacting to problems and doing this sort of thing,” he said.
Like Moskovitz, nearly all bosses are ‘accidental’—and it’s actually the top reason they end up quitting
Moskovirz isn’t the first boss to admit he never intended to manage people. Like Gen Z, who admit they would rather remain individual contributors forever than climb the greasy pole, many managers before them have secretly thought the same.
In fact, research shows that as many as 82% of bosses are “accidental”—they had zero training and were simply thrust into the role because they were at the functional or technical aspects of the job. So it made sense to promote them to show others how it’s done, whether they actually want to lead or not. A quarter of them wind up in senior leadership roles.
As a direct result of this, businesses end up with managers who aren’t confident in their ability to lead, and who struggle to deal with the various challenges that come with managing people, leading both employees and struggling managers to resign.
Gerrit Bouckaert, CEO of Robert Walters, a recruitment firm that works in 31 countries, said the trend of accidental management has become more “pronounced” in recent years—all the while the demands of the job are only getting tougher.
“In the past, a manager’s primary role was to keep employees motivated and productive,” he previously told Fortune. “In today’s world, they are required to drive the culture and inclusion in the team, lead on digital adoption, possess an innate ability to know if a member of their team is struggling mentally, and also be the bearer of bad news—be it delayed promotions, or muted pay rises.”
A version of this story originally published on Fortune.com on October 23, 2025.
Read more career advice from Fortune’s Orianna Rosa Royle:
- Backstabbing is the new office norm: Gen Z and millennials are blame-shifting, snitching, and setting others up to fail—but so are managers
- $5 billion CEO calls the managers that candidates didn’t list as references—and he’ll even ask coworkers they clashed with what they really think
- L’Oreal exec tells Gen Z new hires to be that person who grabs their manager’s coffee—instead of making you look junior, she says it can get you noticed
- Cisco’s top exec spent 25 years climbing the ladder at one firm—she tells Gen Z and middle managers ‘you just need to be patient’
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