5 mistakes leaders make when telling stories

I was running a storytelling workshop a few months ago for a group of senior leaders, and I asked them to do something simple.

I said, tell me a story about a time your team solved a genuinely hard problem.

One by one, they went. And almost every single one of them did the same thing. They described the situation, listed what they did, told me the outcome, and sat back down.

Clean. Organized. Completely forgettable.

What they gave me was a report. What I asked for was a story. And here’s what I’ve come to understand after running enough of these workshops and sitting through enough leadership communications: most leaders genuinely believe they’re telling stories when they’re doing something else entirely.

They’re summarizing. They’re reporting. They’re presenting. But they’re not telling stories, and the room can feel the difference even if they can’t always name it.

So here are five mistakes I see leaders make consistently, drawn from workshops, conversations, and years of watching people communicate what matters.

Mistake 1: They start with the outcome and wonder why no one leans in.

A few years ago, I was in a room where a CEO was addressing his leadership team after what had clearly been a brutal quarter.

He opened with: “Despite the challenges, we delivered 23% growth, and I’m proud of what this team accomplished.”

There was all-around applause. And then everyone in the room went straight back to checking their phones.

We lost three of our top clients last quarter. I was convinced we were done, and what saved us wasn’t a new product but a single conversation, Anita, our mid-level account manager, had with our client.

This was a conversation that nobody told Anita to have. This turned around all three clients. That’s what the 23% was built on. Now, you’re listening.

But the CEO started with the number, and so nobody felt a thing. The story was there. He just told it backward.

Mistake 2: They make themselves the hero.

I run storytelling workshops, and I have a small exercise where I ask participants to tell me about a time when something went wrong and what they did about it.

Almost without exception, the story ends with them solving it. Their instinct, their call, their intervention. Even the most self-aware leaders in the room structure it that way.

The most powerful stories I’ve seen leaders tell were the ones where the hero was someone else, such as a customer who gave them an honest piece of feedback that changed everything, a junior team member who spotted something everyone else missed, or a failure that became the actual turning point.

When the leader positions themselves as the person who learned something rather than the person who knew it all along, the audience trusts them more, not less. It’s counterintuitive, but it’s consistent.

Mistake 3: They tell the audience what they should feel at the end.

I think about the 2006 interview I had for a Marketing Head position at an IT services company. As part of the process, I met the EVP for lunch.

For 75 minutes, he asked me exactly one question, “Tell me, Saba?” and every time I paused, he said, “Tell me more, Saba.”

That was the entire interview.

When I recently told this story to a group of HR leaders, I deliberately stopped after describing the lunch and didn’t say anything for a moment.

Someone in the room said, quietly, “That’s the most respectful interview I’ve ever heard of.”

I hadn’t said that. I hadn’t needed to. But imagine if I’d ended with, “And that taught me that listening is the greatest form of respect you can show another person.” The room would have nodded, moved on, and forgotten it by the time they reached the car park. The lesson they arrived at themselves is the one that stayed.

Mistake 4: They open with context when they should open with a question that the audience doesn’t know the answer to

At the CX panel I hosted recently, one of the panelists started answering a question with, “So, in 2022, we had just completed a platform migration, and the team had been working on it for about 14 months, and we’d hit most of our milestones…” I watched the room. People were with him physically. Mentally, half of them had already wandered off.

Then, about a few minutes in, he said almost as an aside: “We tested the technology. We never tested the context.”

The room snapped back. People sat forward. Someone wrote it down.

That one sentence, which came buried in the middle, was the opening line the whole story had been waiting for. Everything before it was setup he didn’t need.

If he had opened with “We tested the technology. We never tested the context,” and then explained what that meant, he would have owned the room from the first breath. The loop was there. He just didn’t use it.

Mistake 5: They tell company stories when the human being at the center of the story is the whole point.

When I was working on the 9 Types of Stories eBook, I interviewed a founder who wanted help articulating his company’s origin story.

He kept telling me about the gap in the market, the founding team’s combined experience, and the timing of the opportunity.

All of it was accurate. None of it was interesting.

So, I asked him: “Who’s the first customer who ever trusted you with their money?” He paused for a long time. Then he told me about a woman named Priya, a small-business owner who had met him at a networking event, heard him speak for 12 minutes, and called him the next day to say she wanted to work with him.

She didn’t ask about his team’s credentials. She didn’t ask for references.

She said, “I just think you understand what I’m trying to do.”

He said that call changed everything, not just commercially, but in terms of what he believed the company could be. That was the origin story. Priya was the whole point. The market gap was just the backdrop.

The strange thing about these five mistakes is that none of them requires skill to fix. They require awareness.

Most leaders are already sitting on genuinely powerful stories, experiences from their careers, from their teams, from the work itself, that would land exactly as intended if they just stopped managing them so carefully.

Stories work when you trust them. The mistake most leaders make is that they don’t.

If something in this edition sparked a thought, I’d love to hear it. You just reply, and let’s talk. And if you know a leader who could use this, forward it along.

Until next week.