Why Sharing Failures Makes You a Better Speaker
Founder Scott Hubbard with Hubbard Communication Client (Photo: Tyler Core)
Some of my favorite TED Talks of all time begin with moments of vulnerability.
Amy Cuddy talks about suffering a brain injury in a car accident. Shawn Achor shares a story from childhood about roughhousing with his sister—which ended in a broken leg. And of course, Brené Brown became famous talking about the power of vulnerability itself.
Most of us have a go-to story about the time we nailed it—the one we use in interviews.
Typical FormulaSituation → Action → Result
But here's what I've discovered as I've grown in my career and taught more than 2,000 professionals…
COUNTERINTUITIVE IDEAThe stories that really connect are about the times you messed things up!
Why Failure Stories Build Trust Faster Than Success Stories
When you share a mistake, something magical happens with your audience:
They think, "Hey, this person's like me. They mess stuff up too."
They lean in instead of feeling intimidated
They trust you more because you're being real
They remember your message longer because it felt authentic
I have a whole catalog of these stories now—and they've become the most effective teaching tools I have.
Like the time I put my first customer to sleep. Literally.
The Customer I Put to Sleep (And What It Taught Me)
It was my first full-time job after college—selling ad space at a small-town paper in Kentucky. I was armed with stats. Reach. Frequency. ROI. I was pumped.
So I did what many rookie salespeople do when they get their hands on good data: I dumped it all over my prospect. Slide after slide. Number after number.
When I looked up, the man was asleep. Not figuratively. Not metaphorically. Asleep asleep.
He was a landscape contractor who probably woke up at 3:30 a.m. and had already put in a 12-hour day. He didn't need stats. He needed clarity.
That day taught me one of the best lessons about communication…
REMEMBER THISIt's NOT about what you want to say.
It's ALL about what they need to hear.
How to Use Your Failures as Teaching Moments
The best presenters shape their message to the moment. They listen first. They ask smart questions. They connect through shared humanity.
Here's how to turn your mistakes into powerful stories:
Choose failures with clear lessons:
If you remember the event, you probably learned something from it. And if you learned something, someone else probably will too.
Be specific about what went wrong:
Vague failures don't teach. Specific mistakes with concrete consequences do.
Connect the lesson to your audience's world:
Show how your hard-learned lesson applies to their challenges.
Always remember the power of authentic human-to-human connection. It's still good to have a walk-off home run story. But I find stories that show our flaws to be just as valuable and less common.
When you show your audience you're human, you create space for real connection. And that connection is what makes your message stick.
Ready to Tell Your Story Better?
Whether you're sharing successes or failures, the key is making your message land with authenticity and purpose.
At Hubbard Communication, I help thoughtful leaders be heard—not because they speak louder, but because their message is clear. Let's make your next presentation the one people actually remember.
