Operating Well: What I Learned at Stripe

• Can we re-frame this in terms of the customer’s problem?


• What’s the soonest we could get this done?


• What would you need to get this done tomorrow instead of next week?


• What would we need to do to get twice as many customers? Ten times as many customers?


• How does this relate to our goal? Is this the most important thing we can do for our goal?


• What’s mos

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When something isn’t getting done, it’s because the person a) doesn’t have the time b) doesn’t have the skill or c) has some sort of psychological block. The third case is surprisingly common.

What you don’t want to happen is unsustainable stress, or for people to not share failure or tell you when you’re wrong. So you need to actively fight this as the leader by: a) asking for dissent (“does everyone agree this is the right path? Does anyone disagree”? and letting a silence hang until someone speaks) b) reward debate.