What’s Your Most Embarrassing Story?

If you’ve ever been to a team-building offsite, you’ve probably played—or narrowly  avoided—that trust exercise where someone falls backward and the person behind  them is supposed to catch them. 

I hate that game. 

It’s ridiculous. No one actually trusts it. And more importantly, no one wants to die in the  name of teamwork. So let’s agree: falling exercises do not build trust. They build anxiety  and awkward HR conversations. 

But the impulse behind the game is right. Leaders want trust. They want safety. They  want teams to stop posturing and start being real with each other. 

There’s another way to do that. And it doesn’t involve gravity. 

Years ago, I walked into a management team that didn’t really know each other yet.  Smart people. Capable people. Polite. Guarded. Everyone was doing what high performing adults do when they don’t feel safe yet: saying very little and managing  impressions very carefully. 

So I tried something different. 

I said, “Who wants to hear about the most embarrassing thing that’s ever happened to  me? But there’s a catch. If I go, everyone else has to go too.” 

Then I went first. 

And no—I will absolutely not tell you what that story was. It truly is the most humiliating thing that’s ever happened to a human being. 

But something interesting happened.

A few people jumped in immediately. Others sat back, arms crossed, watching. And of  course, there was that person—the one who said, “The most embarrassing thing that  ever happened to me is that I’m a perfectionist and once got a 99.9 on an exam.”  

Thank you for your bravery. Ugh.  

But then… slowly… something shifted. 

With the help of a little wine, stories started to flow. And I mean some real GEMS. I’m  talking blood, guts, indecency, maybe clothing maybe be no clothing, maybe criminal  consequences, it was absolutely fantastic. Stories that made you think, I will never see  you the same way again. 

And you don’t. 

Because once someone shares something genuinely vulnerable—something they  absolutely do not want repeated outside that room—you now hold something together.  You have shared information. Shared risk. Shared humanity. 

That’s trust. 

What are the consequences of that kind of vulnerability? 

They stop performing and start collaborating. 

They give each other more grace. 

Maybe when the time comes, they will have your back  

And yes, you also learn a lot. 

You learn that some people you assumed were extroverted have nothing to share—or  hide behind nonsense. You learn that others who seemed buttoned-up have lived entire  lives you never imagined. You learn who understands the exercise and who is still  protecting themselves. 

And here’s another important lesson: give people a second chance. 

Fear and embarrassment take time to wear off. Sometimes the best story shows up  later, once people realize the room is actually safe. When it does, it’s usually worth the  wait. Second chance stories are usually better than the original. 

For CEOs and senior leaders, this matters.

Trust is not built by slogans. 

Safety is not built by posters. 

And vulnerability is not built by telling other people to open up. 

It’s built by leaders going first. 

So the next time you’re tempted to run a trust fall, don’t. 

Try this instead: 

“Who wants to hear the most embarrassing thing that’s ever happened to me?” 

Then mean it. 

Then go first. 

Then protect what’s shared. 

You might just build the kind of trust no one is willing to fall backward for—but everyone  is willing to stand up inside.