Tell Me More. The three words that unlock every story

Somewhere in the mid-2000s, I sat down for what I thought was a job interview.

It wasn’t. Not in any way I recognized.

I had lunch with the interviewer, a senior gentleman I’d never met before. Seventy-five minutes, a proper meal, completely unhurried. And in that entire time, he asked me exactly one question. Two versions of it, really.

Tell me, Saba.

And when I’d pause: Tell me more, Saba.

That was it. No competency questions. No “where do you see yourself in five years?” No structured format of any kind. Just those four words, repeated gently every time I ran out of steam.

And I talked. I talked about everything, like the things I’d done, things I’d tried, things that hadn’t worked, things I was still thinking about. I wasn’t structured. I wasn’t performing. I wasn’t trying to say the right thing. I just talked because the question kept creating space, and

I kept filling it.

By the time lunch ended, I felt like I’d said more about myself in 75 minutes than I had in years of formal interviews combined.

That’s the power of “tell me more.” It doesn’t ask for anything specific. It doesn’t narrow the conversation. It just opens a door and waits.

Finding stories

Most of us think finding stories in an organization is about observation. But the richest stories, especially the ones that explain why a team behaves the way it does, why a product was built the way it was, why a company survived something it probably shouldn’t have, don’t surface on their own.

They need to be invited out.

The problem is that most invitations are too specific. “Tell me about a time you failed” puts people on guard. “What’s your biggest challenge right now?” gets you the safe, rehearsed answer. The moment a question has a shape, people fit their answers into that shape. And in doing so, they leave out everything that doesn’t fit, which is usually the most interesting part.

“Tell me more” has no shape. It can’t be gamed. It doesn’t signal what kind of answer you’re looking for. It just says: keep going, I’m listening.

But here’s what nobody talks about.

Sometimes you ask, and what comes back is technically an answer, but it’s too clean. Too practiced. The kind of answer that closes a conversation rather than opens one.

I was talking to a marketing leader about her content plans.

“Tell me more,” I said.

“We’re focusing on thought leadership this quarter,” she said.

Smooth. Confident. Complete.

I didn’t move.

“What does thought leadership mean for you here?”

She smiled slightly. “You know…the insights, trends, industry pieces.”

I stayed with it.

“What’s one idea you’ve held back from publishing?”

She stopped. Then laughed a little.

“There is one. But it’s a bit controversial.”

That laugh was the door opening. We hadn’t been somewhere real until that moment. The first two answers were the version she’d already decided to share. The third one was something she hadn’t quite said out loud before.

That’s what you’re listening for. Not the clean answer, but the moment just after it.

The other kind of silence is different.

It’s not polish, but frustration. Someone who has something to say but hasn’t found the words yet, or hasn’t been asked the right way.

I was in a conversation about sales and marketing alignment. A familiar topic, and usually a fraught one.

“Tell me more,” I said.

He sighed. “Sales just says the leads aren’t good enough.”

A familiar script. I’d heard it a hundred times.

“What exactly do they say is missing?”

“They say the leads aren’t ready.”

I leaned in.

“Do you remember the last lead they rejected?”

He thought about it for a moment.

“Yeah. They said the prospect didn’t even understand the problem we solve.”

And just like that, the issue wasn’t lead quality anymore. It was messaging.

The leads weren’t bad. The market didn’t understand what the company did. That’s a completely different problem with a completely different solution, and it had been buried under a familiar complaint that everyone had stopped questioning.

He’d known something was off. He just hadn’t been asked the question that helped him see what it was.

Circling back to “Tell me more.”

I think about that lunch from the mid-2000s often, especially now that story-finding is the work I do professionally.

What that interviewer understood, and what took me years to fully appreciate, is that the best way to understand someone isn’t to ask them better questions. It’s to ask them fewer questions. To create enough space that they stop thinking about what you want to hear and start saying what they actually know.

When someone gives you a clean answer, stay with it. Tighten the frame slightly. Ask about the one thing they haven’t mentioned. Ask about the last specific instance, not the general pattern.

And when someone goes quiet, really quiet, don’t fill it with your own story. The moment you start talking, the thing they were about to say goes back inside. Sit with it one beat longer than feels comfortable. Most people, if you don’t rescue them, will rescue themselves.

He asked me two things in 75 minutes. I told him everything.

The organizations with the richest stories aren’t the ones that have done the most remarkable things. They’re the ones with someone willing to sit down, lean in, and say: tell me more.

And then actually wait.

Let me know what you think of this. Maybe you should try this out and let me know how it went.