How to get better at getting it wrong
Why the best leaders don't just tolerate failure, they get better because of it.
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Let’s talk about something most teams avoid: getting it wrong.
Mistakes. Errors. Slip-ups. Misjudgments. Or, as some teams I work with prefer to say - “things that didn’t go to plan.”
Whatever you call them, they’re happening. No individual or team is perfect. But in many senior teams, no one talks about them. In fact, in my experience, the more senior the team, the less they’re talked about.
And that’s a problem.
If people aren’t sharing mistakes, they aren’t being open with each other.
And when that happens, teams miss out on the learning, adaptation, and growth that come from failure.
High-performing leaders and teams don’t avoid mistakes - they get better at handling them. They operate with the mindset that learning is an iterative process.
Practice: Try something
Fail: It doesn’t work as expected
Learn: Talk about it, tweak it, improve
Repeat: Do it again, but better
But this cycle only works if people feel safe enough to talk about what went wrong.
And this is where leadership is crucial. Psychological safety - the ability to speak up without fear of blame or shame - is what allows learning to happen.
If you lead a team, ask yourself:
Do people feel comfortable telling me when something hasn’t worked?
Do I talk openly about my own mistakes?
Do I model learning from failure rather than hiding it?
But many senior leaders have perfectionist streaks. They want things done right the first time, especially when it comes to their own performance. And this makes it even harder to talk about when things haven’t gone perfectly.
And let’s be honest. You’ve reached the level you’re at because you’ve done things well. Not because of the mistakes you’ve made. So it’s normal to be mindful of your reputation and credibility - and to want to protect it.
But if you’re in a team that never talks about what’s not working, it doesn’t mean everything is perfect. It means people aren’t sharing what’s not working. And at worst, they’re hiding things. That’s a big business risk.
The best teams and leaders? They don’t just tolerate failure - they use it. They extract the lessons, refine their approach, and improve.
And that’s where the gold is.
Below you’ll find five sets of coaching tools that you can use alone or with your team, to explore how you can get better at getting it wrong, today.
Reflect: The way you respond to mistakes will shape your team’s culture. If you’re uncomfortable with mistakes, your team likely will be too. Take a moment and consider:
How do you react when something goes wrong - curiosity or frustration?
Do you openly share when you’ve made a mistake, or do you keep it to yourself?
What happens in your team when failure occurs - silence, judgement, or learning?
Invite: Instead of letting failures go unspoken, create space for learning. This shifts failure from something to fear into something to learn from. Ask your team:
What’s something that hasn’t worked as expected in the last month?
What adjustments have we made as a result?
What can we do differently next time?
Where do we need to give each other more permission to experiment?
Focus: Leaders set the tone for how mistakes are handled. If you want your team to be open about failure, you have to lead the way. Consider:
How can you role-model openness about what hasn’t gone to plan?
Where could you share a recent failure and what you learned from it?
How do you respond when your team shares a mistake? Do you listen or jump to solutions?
Reframe: The goal isn’t perfection - it’s progress. But many leaders and teams still attach stigma to mistakes. Words shape culture. Make sure yours invite reflection, not fear. Ask your team:
What language do we use around things that don’t go to plan?
Do we treat mistakes as a source of insight or a source of failure?
How can we talk about things that don’t go well in a way that encourages learning?
Grow: The best teams don’t avoid failure - they build the muscle to recover and improve. And the teams that grow fastest expect failure - and get better because of it. Use these three questions with your team to talk about what you can do to keep on driving progress:
What’s one way we can create more psychological safety in the team?
Where do we need to experiment more and embrace iteration?
What’s one small shift we can make this week to normalise learning from failure?
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