When someone in your team fails… what do you do? Featuring Winston Churchill and Michael Jordan.

21 October 2025

A project misses the deadline.
A rep loses a key deal.
An ambitious idea flops.

And just when the person most needs support — their leader turns cold.
Withdraws.
Punishes.
Emotionally discards them.

But here’s the thing:
👎 That moment isn’t just a test of the employee.
✅ It’s a test of 𝘺𝘰𝘶 as a leader.

𝗠𝗶𝗰𝗵𝗮𝗲𝗹 𝗝𝗼𝗿𝗱𝗮𝗻 reflected:
“I’ve missed more than 9,000 shots in my career.
I’ve lost almost 300 games.
26 times, I’ve been trusted to take the game-winning shot… and missed.
I’ve failed over and over and over again in my life.
And that is why I succeed.”

𝗪𝗶𝗻𝘀𝘁𝗼𝗻 𝗖𝗵𝘂𝗿𝗰𝗵𝗶𝗹𝗹 suggested that: “Success is the ability to go from one failure to another with no loss of enthusiasm.”

As the story goes, 𝗧𝗵𝗼𝗺𝗮𝘀 𝗝. 𝗪𝗮𝘁𝘀𝗼𝗻 𝗦𝗿. (founder / leader at IBM) was once asked whether he’d fire an employee whose mistake cost the company $600,000. His reply reportedly was: "I just spent $600,000 training him — why would I want someone else to hire his experience?"

As a leader, you can’t always stop the fall.
But you get to decide how someone 𝘭𝘢𝘯𝘥𝘴.
Do you kick them when they’re down? No matter how unintentional.
Or do you help them make sense of the failure - so they come back stronger?

🎯 Because in any bold action, there are only two outcomes:
You win, or
You learn.

Great leaders know this.
And they create a culture where people are safe to try & stumble - and grow.

💬 What’s the best way 𝘺𝘰𝘶’𝘷𝘦 𝘴𝘦𝘦𝘯 𝘢 𝘭𝘦𝘢𝘥𝘦𝘳 𝘩𝘢𝘯𝘥𝘭𝘦 𝘧𝘢𝘪𝘭𝘶𝘳𝘦 in their team?

Written by Jonathan Stern
ICF Certified Coach | Gallup CliftonStrengths Certified | Former MuleSoft ANZ Leader
I coach high-potential leaders and high-potential scale-ups.
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