However they may have left, what most share in common is a hard time letting go. Many founders have trouble giving their successors absolute authority. Schultz once wrote that it's like being a “parent standing back and watching his children make their own choices.”
“Their DNA does not allow them to step back and be an independent board member,” said Peter Crist, chairman of the executive search firm Crist Kolder Associates. “They still involve themselves. They still meddle. They still call someone three levels below and ask what's going on.”
Management experts say that transition could be more challenging for Kalanick, who has a reputation as an aggressive, win-at-all-costs chief executive who built a “Hobbesian” culture that's been under fire for unprofessional, frat house conduct and allegations of widespread sexual harassment.
“He has this competitive streak,” said Jeffrey Sonnenfeld, a professor at the Yale School of Management who wrote a book about the psychology of CEOs departing their companies. “This is not a guy who's going to go softly into the night.”
In addition to his personality, Kalanick's management style has been described as particularly hands-on, a micromanager who's gotten involved in details as minor as a redesign of the company's logo. He had such a consolidated level of power that the first recommendation in the report by the law firm Covington and Burling on Uber's cultural reforms urged the company to reallocate some of Kalanick's responsibilities.
Even after he took an unspecified leave of absence last week, Kalanick was reported to have stayed in frequent contact with executives, interviewing candidates for the many vacancies on Uber's executive team and dialing in with his thoughts. After director David Bonderman made a disparaging remark about women during a company meeting designed to address the company's cultural issues, Kalanick personally worked the phones to get Bonderman off the board, according to a report in the New York Times.
“The next CEO of Uber is going to do things differently, and Kalanick is going to have a hard time with that because of his emotional investment,” said Kerry Sulkowicz, a psychiatrist and psychologist who advises boards and CEOs, including several running successful start-ups. For many CEOs, “there's a high risk of succumbing to the temptation to meddle. Or worse: to actively undermine the new CEO by unconsciously behaving in a way that destroys what’s most important to him, as a way of proving to himself and the world that he was indeed irreplaceable.”
It's also possible Kalanick could be emboldened by his equity stake. Because he and his allies retain so much voting power through the shares he owns, management experts say it makes sense that he remains on the board. “You know the old joke ‘gone, but not forgotten?’ ” said Charles Elson, the director of a corporate governance center at the University of Delaware. “He’s gone but has too big a stake to be forgotten.”
The Uber investors who wrote the letter calling for Kalanick's resignation have called for two of three empty board seats to be held by “truly independent directors,” according to the New York Times, which would dilute Kalanick's vote on the board. A company spokeswoman declined to comment further on what else the board might do.
Sometimes, having an involved former founder on the board is a positive, a connection to the company's origins and a font of institutional knowledge and vision. Schultz is widely seen to have revived a fading Starbucks when he took back the reins from a successor, hearing complaints from employees and recognizing the company had drifted from its roots. And founders such as Bill Gates at Microsoft were seen as constructive board members to their successors after they stepped out of the CEO's seat.
But there are plenty of times when a CEO, even by his own choice, leaves the top job but clashes with his or her successor. Ralph Lauren handed the CEO title to outsider Stefan Larsson, but the two couldn't agree on creative direction and Larsson left the company less than two years after he started. Lululemon founder Chip Wilson, who hadn't been CEO since 2005 but remained on the company's board until 2015, argued with a successor over things like putting Ayn Rand quotes on shopping bags and voted against company directors over the direction of the company.
When such changes come amid an emotional personal hardship — as has happened to Kalanick, whose mother recently died in a boating accident — the change can be complicated, Sonnenfeld said, unless the founder gets involved in something new.
“I have seen this before where there's a personal tragedy,” he said. “[Former Nike CEO] Phil Knight stepped out after his son died, but he got a second wind, came back, and pulled the rug from beneath [successor] Bill Perez, who was doing a good job.”
Kalanick's board presence could also give some recruits to the CEO job pause. While plenty would probably jump at the opportunity to overhaul what has become the most disruptive and valuable Silicon Valley start-up of this era, others could look warily at how much Kalanick will stay involved.
“They’ll swallow hard, close their eyes and they’ll do it,” said Crist, the executive recruiter. “But it doesn’t change the fact that his influence and personality are still going to be quite evident.”