The fastest way to kill a story is to ask for one

A friend called me last week, a little deflated.

He works at a large multinational. The company had given him a role he actually wanted: storytelling mentor to three new joiners spread across different countries. One hour a week. Help them use stories to connect, influence, and build credibility at work.

His first session did not go the way he imagined.

He asked them to share a story. All three froze. Not the polite, awkward pause you can talk through. A proper freeze. The silence stretched. Everyone stared at their own lap. He waited. Tried rephrasing. Tried making it smaller: “just any story, doesn’t have to be work-related.” Nothing.

So, he did what most good mentors would do. He told a few stories himself. Warmly, generously. Hoping they’d loosen up. That something in his stories would remind them of something in their own lives. They listened politely. Nobody shared anything.

“I don’t know what I’m doing wrong,” he said.

Here’s what I told him.

The problem isn’t that these three people have no stories. Everyone has stories. The problem is the word “story.”

The moment you ask someone to tell you a story, they start performing. Some internal critic wakes up: Is this interesting enough? Is this even a story? What’s the lesson supposed to be? Am I telling it right? And under all that weight, they go blank.

The fix is simple. Stop asking for stories. Start asking questions.

• What was your first day here like?
• Was there a moment in the last month where you thought, okay, this is somewhere I want to stay?
• Tell me about something that surprised you, good or bad, about how things work here.

These don’t feel like a performance. They feel like a conversation. And when people answer them, they don’t give you bullet points. They give you scenes. They tell you about the colleague who sat with them for two hours on day one and showed them every shortcut, or the one who barely looked up. The meeting where something clicked. The moment they first thought, wait, is this normal?

That’s a story. They just don’t know it yet. And you don’t need to tell them it is.

My friend said he’d try this in the next session. I haven’t heard back. But I’ve seen it work enough times to be fairly confident he’ll have a different kind of conversation.

That whole exchange got me thinking about something else.

A quieter mistake I made for years, one I never got around to mentioning to him.

For a long time, I genuinely believed the six most powerful words you could say were: Let me tell you a story.

I used it as a signal. A way of lowering the volume before I started speaking. Graceful, I thought. Inviting.

It wasn’t. It was a warning.

The moment I said those words, people leaned back slightly. A courteous blankness settled over their faces. They’d already decided to be an audience. And audiences are passive. They receive, they don’t participate.

What changed things for me was when I stopped announcing and just started.

“I was presenting connectivity solutions to a state transport corporation. The evaluating agency had already made up its mind before we walked in, and we could feel it. Instead of opening with slides, we started off with a story, playing a short video. Real end users. Real voices talking about what the solution would mean for them. Nobody in that room had expected that. By the time the video ended, the room had changed. We made it to the next round purely on the strength of that opening.”

Nobody checks out when you start like that. A scene has already begun. There’s a person, a place, a problem. The listener is inside the story before they’ve decided whether to be.

And here’s the thing I didn’t expect: when you start without announcing it, people don’t just listen. They start quietly reaching back into their own memories while you’re still talking. Something you say touches something in their life. By the time you finish, they’re not passive anymore. They want to talk.

That’s when a conversation actually goes somewhere.

Aren’t they related?

These two things are the same problem, really, just from opposite ends.

The new joiner who freezes when asked to “share a story.” The speaker who loses a room the moment they say “let me tell you a story.” Both become self-conscious the instant they’re reminded that a story is supposed to be happening. And self-consciousness is where stories go to die.

Stories work when they feel like they just happened. Like someone started talking, and you ended up somewhere you didn’t expect. The skill, if there is one, is in making it feel accidental. Asking the question that sounds like curiosity but is really an invitation. Starting a scene so naturally that nobody notices the door they just walked through.

We teach communication at work as if it were a performance. Here’s the structure, here’s the arc, here’s the framework. Then we’re surprised when people freeze on command.

Stories don’t live in frameworks. They live in the answer to “how was your first day?” They live in whatever someone says when they actually stop and think about it.

And they live in the moment someone starts talking, and the room leans in. Not because anything was announced. Just because something true began.

What question has unlocked the best stories in your conversations? I’d love to hear.