Disagreeing with coworkers is rarely easy — and it’s even trickier when that coworker is your co-CEO.
Dropbox co-CEO Ashraf Alkarmi told Business Insider that disagreeing with coworkers is simply part of any job.
Alkarmi, who previously held leadership roles at Vimeo and Meta, joined Dropbox as senior vice president and general manager of its core products in 2024. He became co-CEO in May, alongside Dropbox founder Drew Houston, and will eventually become the company’s sole CEO.
“Since I joined Dropbox, I had a relationship with Drew that was really based on trust, respect, and debate,” Alkarmi said.
Alkarmi said the first step to navigating disagreements is building trust and mutual respect with your coworkers. When that foundation is in place, people know your feedback comes from a good place.
A foundation of trust isn’t enough, though. The second key to healthy disagreement, Alkarmi said, is being a truth teller.
“Use facts,” the co-CEO said. “Use a lot of data. Use what you believe.”
Alkarmi said it’s fine to trust your instincts, but your perspective should be backed by clear reasoning. He said it’s important to communicate directly rather than expressing disagreement in a passive-aggressive or hidden manner.
“I’m a believer in radical candor,” Alkarmi said. “Have the trust and care, and deliver it directly.”
Alkarmi also said it’s important not to avoid difficult conversations. Those moments, he said, are often where trust and respect are built.
“In moments where you are actually delivering something that’s hard, but with respect and care, it actually helps build that flywheel of trust and respect,” Alkarmi said.
Even after following those steps, some arguments don’t end in both parties seeing eye-to-eye.
In those situations, Alkarmi said he and Dropbox founder and co-CEO Drew Houston have developed a system. Alkarmi said he’ll continue challenging an idea until Houston uses a specific keyword — “final” — to signal that the decision has been made. Until then, he knows the discussion is still open for debate.
Once Houston makes the final call, though, Alkarmi said there’s one “critical” step that makes the dynamic work: full commitment. After Alkarmi has had the chance to discuss the issue and explain his reasoning, he treats the decision as his own and commits to making it successful, he said.
Alkarmi underscored a concept Jeff Bezos has popularized in Silicon Valley: “disagree and commit.” In his 2016 shareholder letter, Bezos wrote that being willing to take a gamble on a decision you initially opposed can “save a lot of time” when colleagues can’t reach a consensus.
Alkarmi said that once a decision has been made, both parties need to fully embrace it.
“Whether it works or not, it’s not his opinion or my opinion. It’s what we both fundamentally actually ended up agreeing on,” Alkarmi said.
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