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He was a Google VP and Stripe’s CTO. He has 2 pieces of advice for conducting engaging meetings.

September 9, 2025
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He was a Google VP and Stripe’s CTO. He has 2 pieces of advice for conducting engaging meetings.
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A meeting is pictured.
Former Stripe and Google exec David Singleton gave advice for keeping meeting attendees’ attention.

filadendron/Getty Images

David Singleton wants leaders to stop and think before they attend a meeting.

Singleton, the former CTO of Stripe and vice president of engineering at Google, recently appeared on “The Peterman Pod,” where he offered two tips to leaders who want to command attention and engagement at their all-hands meetings.

The first is to prepare in advance.

“I have made this mistake many times, where I’d be told, ‘Oh, just show up and give us a bit of your top of mind,'” Singleton said. “What’s on top of my mind right now is that I’m kind of hungry, and I’m not going to say that.”

Meeting leaders should “think about what is the most useful context for that audience to hear about and put some thought into it,” he said.

“They’re all spending 15-20 minutes of their time listening to you,” Singleton said. “The least you can do is spend 30 minutes of your time preparing.”

Other business leaders agree. Jamie Dimon, who famously hates meetings, said that he reads ahead of time and asks his employees to do the same. Jeff Bezos and his Amazon successor, Andy Jassy, ask leaders and participants to write memos before meetings to be read by participants.

Singleton’s second piece of advice: Take a beat before answering questions.

The lesson dates back to Singleton’s days at Google, where he worked under senior vice president of engineering Alan Eustace. Singleton said that, when Eustace was asked a question, he would articulate back to the room why the question mattered before he answered it.

Singleton said that Eustace’s technique worked because “folks who weren’t already immediately familiar with the problem at hand could actually both understand what was going on, and could actually learn something broader from that.”

“I aspire to be like Alan,” he said. “I’m certainly not that good, but I noticed that and it really stuck with me. That’s part of: Take a beat. Is it possible to take a step back and explain the context behind what you’re about to jump into?”

Singleton said that explaining the context behind questions helps keep workers engaged.

“If you’re talking about something that the people have no idea what it is, they’re never going to pay attention,” he said.

The post He was a Google VP and Stripe’s CTO. He has 2 pieces of advice for conducting engaging meetings. appeared first on Business Insider.

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