Operating Well: What I Learned at Stripe

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. If someone dissent

Once you’ve set goals, you need to reinforce them everywhere. Constantly restate the goal and how it maps to your vision and strategy. Ask how every initiative contributes. The first order effect is to make sure your team is working on the most important things. But the second order effect is to ensure your team is applying the goal to the thousand

Consistency just feels good to our system centric product/engineering/design brains. But it creates a huge coordination cost and prohibits local experimentation – everything has to be run against a single standard that multiplies in communication complexity as the organization gets larger.

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. After a few slips with someone I trusted, I’d just ask directly. “I noticed this work isn’t being pushed forward at the rate I expected or at the quality you

Some of the questions I repeatedly ask:

• 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

Give good feedback (and ask for it, explicitly). A lot has been said elsewhere so I’ll go with: do it frequently and immediately, from a place of care, as a set of things you have observed, explaining the impact.