Am I proud of this?

This has become one of the most important questions I regularly ask myself. I also ask people in my team: are you proud of this?

As a company starts to scale, there will be others making decisions, building functionality, and creating experiences. As that happens, you should not expect that others approach things exactly as you would. You need to give people space, and let them surprise you with their creative ways of solving problems. But this can become a trap, too. Sometimes you try to let people do things their own way, but the quality isn't there, and you don't see the results you need. As a leader, you have to maintain a high bar, otherwise the product, service, culture will deteriorate.

Asking "am I proud of this?" cuts through all of this. It's a beautiful question, because the answer is clear. I'm either proud of the work done, or I'm not. And what's really special about the question is that someone could propose an idea or a solution that I would never have thought of, and I can absolutely be proud of them, and proud of Buffer, for putting that value out to customers.

I've also found that asking my team "are you proud of this?" can help them snap out of trying to meet my expectations, and encourage them to look within themselves, to actually use their intuition and gut. It can nudge people to go deeper in understanding customers, so they can emerge from that context with a more natural sense of the right thing to build, or the right way to respond.

This question can help ensure that people don't stop short of producing something truly remarkable. It's easy to let viability and constraints get in the way of greatness. I often find in meetings we can be so focused on having data or expectations give us the answer, and asking "are you proud of this?" can sometimes feel jarring (in a good way), it's often not expected to actually check in on how you personally feel about the work you're doing. I believe companies and customers need more folks who are invested enough to feel their own conviction on something.

Asking "am I proud of this?" can guide you as a leader towards maintaining a high quality bar, while having a wide variety of approaches to solving problems. I wish I'd started asking myself this question a decade ago. Try it out and let me know how it feels for you.