The Storytelling Mistake that Makes You Look Like a Jerk

Whenever I’m working with people one-on-one, they reference a story they want to tell. When I ask them to share it, they all do the same thing.

They hedge and then say, “I don’t know if this story is any good.”

It’s a verbal pause that really means, “I feel vulnerable telling this.”

It doesn’t matter if they are first-time managers, CEOs of large companies, or philanthropists.  People who are confident and influential in other parts of their work and life can suddenly become uncertain when they have to tell a story.

But “Is this story any good?” is the wrong rubric.

I rarely listen to a story and think, “That’s a bad story.” But what I do notice is when a story doesn’t do the work of building an idea and outcome for the audience.

Which is exactly what happened when I was working with a CEO who told this story:

“It was time for our annual planning. We were coming off years of dramatic growth, and I had an aggressive goal for the year.

As I brought my team together to talk through our goals, I noticed one of the team members start sniffling. That turned into her biting her lip and fighting back tears that eventually tumbled over her cheeks.

I couldn’t believe it. She was crying because of this goal?”

I cocked my head to the side the way a dog does and raised one eyebrow. 

“You can’t tell this story like this.”

“Why?”

“Because it makes you look like the jerk that made your team cry.”

As we unpacked what happened, there was more to the story.

He asked what was making her upset. She said she didn’t see how they would achieve the goal. They had grown dramatically over the past few years, but she wasn’t sure how that growth could continue. It felt like too much. She was worried she would be overworked, stressed out, and end up burnt out.

He laid out the roadmap behind his vision and the steps to get there. He explained why he felt it was achievable, and how everyone would contribute without burning out.

By the end of the discussion, she was nodding and bought in.  

Those are two completely different stories.

I showed him the difference between the two versions. The first version asks the audience to judge the crying. The second gives them enough information to understand the tension that produced it by describing the a-ha moment when he realized the team needed to see the path before they could believe in it, and the resolutions once he laid that path out.

Telling the story and stopping on her tears misses the whole point it’s supposed to build.

The CEO had told the part of the story that fascinated him: his surprise at her crying. He was stunned that she couldn’t see the path forward when it felt so clear to him.

That is a core detail that belongs in the story. He also needed to share his realization that his team didn’t share his understanding and vision. He had to back up, identify what they were struggling with, and bring them forward with him.

The first version makes him look like a leader who cared only about the outcomes and not for the team delivering them.

The second shows a leader who recognized a gap between his vision and the team’s understanding, listened to what was getting in the way, and helped them see a path forward.

It’s still the same conversation with the same people and tears. Just not the same story.

This is a classic storytelling mistake. We tell the version of the story that fascinates us and forget that the audience needs something different from it. This doesn’t mean making up details that didn’t happen. The details are usually there, they’re just easy to miss.

When you’re telling a story you love, you’re focused on what makes it interesting to you. You may not notice the small details that would help someone else understand what was happening, why it mattered, or what changed.

That’s where much of the refinement I do with people happens. They already have a story with the main beats. What they’re lacking are the details and moments that help the audience experience those beats in the way you intend.

Those details are seeds. On their own, they look small, incidental, and easy to skip over. But placed with intention, they’re what grows into the idea you’re building toward. They are the things that ensure the audience gets the payoff the story is supposed to produce.

There’s a reason why one of my storytelling principles is: stories start with audiences.

Instead of asking, “What story do I want to tell,” ask:

“What does this story need in it to build the outcome I want?” 

The question changes how you look at the story and what you notice.

The CEO nodded as I broke it down and agreed.  Then he said “Oh and we smashed those goals that year.  And when it was time for goal planning the next year and I shared the targets, she cried again.”

Before I could smack my forehead he said “I know, I know, I can’t stop the story there. It’s only part of what should be told.“

Exactly.

It’s not about whether a story is good or bad. It’s whether the story builds the idea you need your audience to leave with. Will the details already there help them see it, feel it, or understand it?  Those are the seeds you have to plant.

This is the work only you can do. No outline or AI tool hands you the detail that changes the meaning. That comes from paying attention: knowing the people in your story, understanding your audience, noticing the moment something shifts, surprises or changes a mind. Then comes the judgment: what does your audience need for the story to land the way you intend?

The next time you find yourself wondering, “Is this story any good?” ask whether it’s doing the work you need it to do.  Most bad stories just aren’t finished.

The next time you find yourself wondering, “Is this story any good?” ask whether it’s doing the work you need it to. Most bad stories just aren’t finished.

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Karen Eber is an award-winning author, TED speaker, and storytelling keynote speaker. She is the author of The Perfect Story and her TED Talk on how the brain responds to stories has been viewed more than 2.25 million times. As CEO and Chief Storyteller of Eber Leadership Group, she helps leaders communicate ideas that inform, influence, and inspire.