The CEO question that stumped a room full of COOs

One of the more striking moments at this year’s Fortune COO Summit came when Dennis Woodside, the CEO of Freshworks and a former COO of Dropbox, asked the room a simple question: Who wants to be a CEO?

Not many hands went up.

Woodside found that surprising. His view, he told the crowd, is that if you hold the COO title, it’s usually because your CEO and board already see you as potential CEO material, even if no one has said it out loud.

“If you have the title of COO, you have it for a reason,” he told the audience. “The board and your CEO decided that you are on a path to being ready, potentially to be the CEO.”

That observation resonated with me because, over the years of interviewing chief operating officers, I’ve often encountered the same hesitation. Many COOs are reluctant to say publicly that they want the top job, even when their careers suggest they are being groomed for it. Some genuinely prefer the operator role. Others seem wary of appearing overly ambitious.

But Woodside argues that leaders should be honest with themselves about whether they........

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