How to train your team to say "I was wrong" without drama
Practical rituals to normalize the awkwardness
First weeks in the new company, still wrapping my head around the processes, and then came the need to roll back a release. In the rush to “fix it quickly”, I actually made things worse. In the end, we had to pull off a pretty unorthodox rollback with the team’s help.
I had just started, trust still at zero, and I was facing two options for handling my first real fail: Downplay it, blame the docs, pretend nothing happened or just treat it as a normal part of life.
I went with the second one, the one that felt more like me. I wrote in the team’s Slack channel: «Hey, I messed up the rollback. I wasn’t clear on the process and ended up improvising (badly). Here’s what happened [details]. Can someone hop on a call and give me a hand?». At the next team meeting: «For anyone who missed it, I’m the one who turned a 5-minute rollback into an escape room. AMA».
That rollback story isn’t special. You’ve probably lived through moments like that dozens of times. The real difference is what happens afterward.
Working on the culture around mistakes and normalizing them is probably one of the most powerful levers for helping people work with peace of mind. A team that hides mistakes is a team that lives in constant anxiety. A team that shares them is a team that learns fast.
You already know this. I’m not revealing anything revolutionary.
Psychological safety, fail fast, learn from mistakes: you’ve heard those ideas to death. The real problem isn’t knowing they’re important. The real problem is Monday morning, when someone screws up and you’re not sure how to handle it. Or when you’re the one who messed up and your first instinct is to downplay it.
So in this issue, I want to share something more practical. Not theory, but small rituals and behaviors I’ve seen actually work to break the ice. Things you can start doing tomorrow.
But first, we need to talk about what ruins everything before it even begins.
Two poisons that kill a learning culture
Overdramatizing Mistakes
«I’m SO sorry».
«This is ALL my fault».
«I can’t believe I was that STUPID».
Stop.
When you turn every mistake into a Shakespearean tragedy, you create two problems:
The people listening to you feel awkward on your behalf
You raise the emotional bar for admitting mistakes («So if I have to admit a mistake, I need to mentally prepare myself to put on the same kind of dramatic performance too»)
Mistakes should be treated the same way you’d talk about what you had for lunch. Just factual. Normal. «I pushed to main instead of the branch. Fixed it this way. Moving on».
And the same goes in the other direction: don’t obsess over the mistake someone on your team made, don’t go on a blame hunt. Focus on solving the problem and, once it’s fixed, work with the team to figure out how to prevent it from happening again.
Nothing new, probably obvious, but I still think it was worth saying out loud.
Gossiping about other people’s mistakes
I’ve already talked about the negative effects gossip can have inside a team. If you want to dive deeper:
I’ve seen it happen way too often and I’ve been part of it too. A manager laughing with another manager: «You won’t believe what Luca did with that deployment…». A tech lead sharing a junior’s mistakes with the seniors over a coffee break.
When you gossip about someone’s mistake, you’re sending a very clear message to the team: If you mess up, you’ll be coffee-break material.
The result? A team of secret agents, everyone busy covering their tracks.
Rule number zero, non-negotiable: mistakes are discussed with the person, never about the person. And if you really need to share someone’s mistake for learning purposes, ask for permission and let them be the one to tell the story.
Practical rituals to normalize the awkwardness
Once you’ve cleared out the poisons, you can start introducing rituals that make admitting mistakes feel normal, almost trivial. Here are a few that actually work.
For remote teams: the #oops channel
On his very first day, a new colleague (who had tried it successfully in a previous job) suggested this: a Slack channel dedicated to everyday mistakes. No judgment: only positive reactions, and a healthy dose of irony highly recommended.
Preventive Post-mortem / Pre-flight check
Before starting an important project, the team imagines all the possible ways it could fail. When some of those actually happen, there’s less awkwardness because they were already “expected”.
From a smaller point of view, instead: before every major deploy or release: «What are the three things that could go wrong?». Write them down, share them. If they actually happen, no surprises. If they don’t, you’ve still thought through the fallbacks.
LLL Retrospective
If your team is used to retrospectives, using a format in which teammates can share what they learned is a good way to enable the team to talk about mistakes.
An easy to use format is The Three L’s.
Personal Error Budget
The idea comes from the concept of an “error budget” in SRE (Site Reliability Engineering), but applied to people instead of systems. You tell your team: «Everyone gets three “free” mistakes per month. These aren’t mistakes to hide, they’re expected. If you make it to the end of the month without using any, let’s talk. Maybe you’re not trying anything challenging enough».
It flips the narrative and the focus: from «Did you mess up?» to «Did you use your budget to learn something?»
How to implement it without sounding like a Motivational Guru
Here are some tips that actually worked in my experience:
Always go first. Always. Don’t ask for vulnerability you’re not willing to show yourself
Don’t force it. Some people will jump in right away, others might take months. Don’t call out those who don’t participate
Keep it light. This isn’t group therapy, it’s work stuff
Be consistent. Rituals only work when they become routine, not special events
Celebrate the learning, not the mistake. The focus should always be on “what we learned”, not “how stupid we were”.
TL;DR
Embarrassment doesn’t go away. It’s human to feel vulnerable when admitting a mistake. But you have a choice: let it fester in silence and gossip until it becomes toxic, or turn it into a normal story you tell while pushing the fix.
The difference lies in the tone you use when talking about your mistakes. It’s in the gossip you don’t start. It’s in the small rituals that turn «I messed up» from a confession into just another status update.
Credits: Illustration 1