celebrating mistakes | “i saw you mess up!”

Celebrating Mistakes | “I saw you mess up!”
June 24, 2024

My sister and I often talk about work and we were reminiscing about one of her favorite team-building practices we’d developed together: rooting each other on when we fail.

The practice went something like this: During a staff retreat, she asked the team of ten leaders to each go around in a circle and name a medium-sized mistake they’d made recently. Not so big that it’s a complicated story or so heated that it’s an active conflict. No qualifiers, excuses, explanations, or apologies. She started first by owning up to an email she should’ve sent a week ago and was showered with no-mess confetti poppers, pom-pom shakes, and cheers from laughing teammates.

It ended up being the practice with the most requests for repeats.

The debrief afterward made it obvious why: giggly adults basking in relief. There’s power in telling a group of people who depend on each other, “I see you mess up. I mess up, too! It’s normal in our work and I’m still in this with you.”

That particular organization was a startup that required a lot of experimentation and trust, which in turn requires a lot of tolerance for mistake-making. But as leaders, we’re expected to succeed, never be wrong, and stay bulletproof. The reality leaves most leaders to either disengage from an impossible standard or approach work from a place of shame.

The more shame we carry, the more we finger-point, hide, and resent, making our work miserable.

When we’re already doing so much new, the security of a learner's mindset and culture is essential. Normalizing mistakes makes it easier to give and receive harder feedback that lets us course-adjust.

For this particular practice, as time goes on, the debriefs become golden deepening opportunities -- what if someone’s mistake had an impact they didn’t see? What if there was shared accountability for making a mistake that’s gone unnamed? And if you’re very lucky, What if we named something that is hurting our work right now?

In the next installments of this series, I’ll talk more about the structural supports that lessen the likelihood of mistakes and feedback and accountability practices that help in the aftermath of mistakes.

Til then, tell me what you think. Would you own a mistake in a circle of your teammates?

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