The five most common storytelling mistakes leaders make (and how to fix them)

I’ve spent a lot of time in rooms watching leaders communicate. Town halls, board presentations, client pitches, team meetings, all-hands sessions. And the same mistakes show up, with remarkable consistency, regardless of industry or seniority.

What’s interesting is that most of these leaders are intelligent, experienced people who care about being effective. The mistakes aren’t from laziness or indifference. They’re from habits that were never examined and assumptions about communication that nobody ever challenged.

Here are the five I see most often. Let us look at them and also see what to do about each one.

Mistake 1: Starting with the company instead of the problem

This is the most common and the most costly.

A leader stands up to present to a client, to their team, to an investor, and the first five minutes are about the company. Who we are. What we do. How long have we been doing it? Our clients. Our methodology. Our awards.

The people in the room are thinking about themselves. Their problem. Their situation. Their pressure. And for the first five minutes, nothing in the room is about them.

By the time the leader gets to the part that’s relevant to the audience, they’ve already lost the room’s best attention. Polite attention remains. Genuine attention has moved on.

The fix is a sequencing change, not a content change. Most of what leaders say in those first five minutes is useful, but it just belongs later. Open with the audience’s world. Name their situation specifically enough that people feel recognized. Then earn the right to talk about yourself by demonstrating first that you understand them.

A presentation that opens with “Here’s what we’ve observed in organizations like yours, and it usually comes down to this one thing…” is a fundamentally different experience from one that opens with “Let me tell you about our company.”

Mistake 2: Telling people what to feel instead of showing them what happened

This is the one that kills otherwise good stories.

A leader says, “It was an incredibly inspiring moment.” Or: “The results were remarkable.” Or: “What happened next was something none of us expected.”

Each of these sentences is the leader doing the emotional work that the story is supposed to do. They’re telling the audience what to feel rather than giving the audience the experience that produces the feeling on its own.

The moment you tell someone a story is inspiring, you’ve made it slightly less inspiring. Because now the audience is evaluating rather than experiencing, was it?

The fix is to cut every sentence that tells the audience how to react, and replace it with the specific detail that produces the reaction. Not “it was an inspiring moment.” Tell me what happened in that moment. What did the room look like? What did someone say? What was the pause before they said it? Give me the thing someone did with their hands. Give me the one sentence that changed how you thought about everything.

The detail is the story. The emotional label is a shortcut that doesn’t actually get you there.

Mistake 3: Using examples that could belong to anyone

I hear this version of a story more times than I can count: “We worked with a large enterprise client in the technology space. They were facing challenges with internal communication and team alignment. We helped them implement a storytelling framework, and the results were significant.”

That story could be told by three hundred consulting firms. It identifies nothing. It proves nothing. It stays in the room for about four seconds after you’ve finished telling it.

The problem is not that the story is untrue. It’s that it’s been scrubbed so clean of specifics that there’s no texture left. And texture is what makes a story real. Texture is what makes it believable. Texture is what makes it memorable.

The fix is radical specificity. Name the client if you can. If you can’t, describe them precisely enough to be recognizable, such as their industry, their size, their specific situation, and the particular form their problem took. Name the person you worked with. Describe the moment things shifted. Quote what they said, if you can remember it. Give the audience something real to hold onto.

When I work with leaders on improving leadership communication, this is often the fastest win. The story was always there. It just needed the specifics put back in.

Mistake 4: Skipping the struggle

Most leadership stories go like this: here’s what we were trying to do, and here’s what happened. Beginning, then end. The middle, where everything was uncertain and difficult and could have gone either way, gets compressed or removed entirely.

This is understandable. Nobody wants to dwell on the hard parts, especially in front of people whose confidence you need to maintain. But the struggle is not a weakness in the story. It’s the reason the story works.

Without struggle, there are no stakes. Without stakes, there’s no reason to care. A story in which everything went according to plan and success arrived on schedule is not a story. It’s a press release.

The most trusted leaders I’ve worked with are the ones who talk about the doubt, the wrong turns, the moments when the plan wasn’t working, and they didn’t yet know what to do instead. Not as a confession of weakness, but as evidence that the success that followed was real. That it cost something. That it was earned.

There’s a reason we remember the stories where something almost didn’t work. It’s because that’s where the real information is. Anyone can look good when things go well. Character is visible in difficulty. And an audience watching a leader navigate difficulty, honestly and without performance, learns more about whether to trust that leader than they would from a dozen polished presentations.

The fix is to find the moment in every story you tell where you didn’t know how it would end. That moment is the heart of the story. Stop skipping it.

Mistake 5: Ending without landing

The last thirty seconds of a story are the most important thirty seconds. They’re what the audience takes away. They’re what determines whether the story did any work or just occupied time.

Most leaders end their stories too early; they stop when the events are over, before the meaning has been made. They describe what happened and then move on to the next slide.

Or they end by telling the audience what the story means in the most explicit possible terms, “and the lesson from that is…,” which is the storytelling equivalent of explaining a joke.

The fix is finding the landing. The landing is the sentence, sometimes just a phrase, that closes the story in a way that lets the meaning arrive without being announced.

It’s not a summary. It’s not a moral. It’s the moment where everything that came before clicks into place and the audience understands something they didn’t understand before.

Sometimes the landing is a single image. Sometimes it’s a line someone said. Sometimes it’s a question that the story leaves deliberately unanswered, because the audience already knows the answer, and the not-saying is what makes it land.

This is the hardest skill in storytelling, and the one that separates leaders who are good with a story from leaders whose stories actually change rooms. It takes practice. It takes listening to your own stories and asking: what’s the last thing I want in someone’s head when I stop talking?

And then building backwards from there to make sure that thing arrives cleanly.

The pattern underneath all five mistakes

If you look at these five mistakes together, they share a common thread. They’re all ways of avoiding the real story.

• Starting with the company avoids the vulnerability of showing you understand the audience’s problem.
• Telling people what to feel avoids the risk of trusting them to feel it on their own.
• Scrubbing out the specifics avoids the exposure of claiming something real and being judged on it.
• Skipping the struggle avoids the discomfort of being seen in difficulty.
• Ending without landing avoids the commitment of saying something that actually means something.

Good storytelling is an act of confidence. Not the confidence that you’re impressive. Confidence that the truth of what happened is interesting enough that the real specifics, the real difficulty, the real outcome, told honestly, will do what you need them to do.

Most leaders underestimate their material. The stories they’re sitting on are more powerful than the polished version they’ve been telling. The work is not finding better stories. It’s finding the courage to tell the real ones.

Story It works with senior leaders on the practical skills of leadership communication, from finding the stories worth telling to building the narrative confidence to tell them in any room. If you’re making some of these mistakes, that’s not unusual. It’s also not permanent.