Delivery Message Presentations Storytelling

5 Reasons Why Your Story Falls Flat

Person with glasses on and yellow shirt who looks nervous. Orange background with a book, notepad, cup, and whiteboard floating.

For years, communicators have been told about the importance of telling a story in a professional or business setting. They know stories leave a greater impact on listeners than facts alone, persuade audiences toward action, and help keep listeners engaged.

But many communicators are hesitant to heed this advice. Why? Mostly because they’ve heard others tell stories in a presentation, sales conversation, or meeting which left no impact on the audience or obfuscated the speaker’s primary point.

It’s important to tell a story, but it’s more important to tell a story well.

To help you tell a better story, let’s consider five reasons stories often fall flat in a professional setting.

Mistake #1: The Story Has No Point

How many times have you heard someone tell a story and then thought “Uh… what was the point of that story?” This is common.

When people decide to tell the first story which marginally relates to the topic at hand, they often end up telling the wrong story. The wrong story is a story which doesn’t have a point and doesn’t connect to the audience.

A powerful, effective story has a point. Aesop knew this. The ancient Greek fabulist wrote his fables (a short story featuring humans and/or talking animals) to express morals. Those morals were lessons designed to help the listener understand how to live a better life. “Slow and steady wins the race.” “Heaven helps those who help themselves.” “Don’t count your chickens before they hatch.”

Every story you tell should have a point. And the point should be able to be wrapped up into a helpful statement to guide the listener to a helpful insight. Like Aesop’s fables, “Necessity is the mother of invention.”

Some examples of story points in business settings include:

  1. If you sign up for v.2 of our software soon, you won’t experience a gap in service.
  2. A reorganization will help improve company morale.
  3. We’ve overcome challenges like this… and we can do it again.

Your audience can sense when your story has a clear point. And a clear point gives them instructions to act differently.

Mistake #2: The Audience Can’t Relate to the Story

At its essence, a story is about a Hero who wants a Goal but has to overcome Obstacles to attain it. Those three items—the Hero, the Goal, and the Obstacles—are the foundational elements of the story. When a listener hears a story, they need to feel connected to the Hero, the Hero’s Goal, and the Obstacles standing in the way.

Relatability is the listener’s ability to see themself in the Hero, recognize the Goal as familiar, and overcome the Obstacles. When a story is relatable, the listener is more likely to be moved. When a story is not relatable, the listener is left wondering why the story was told.

This doesn’t mean that the Hero, the Goal, and the Obstacles must be exactly like the listener, the listener’s goals, or the obstacles the listener is facing. If this were true, no viewer could connect to a moisture farmer from a desert planet (Luke Skywalker in “Star Wars”) or a juvenile wannabe wizard (Harry Potter) or an heiress on a sinking ship (Rose in “Titanic”). But it does mean there’s something about the main character, their wants, and their challenges, which feel familiar to the listener.

When you decide to tell a story in a professional or business setting, think about your audience before you think about what story you want to tell. Who is the audience? What do they want? What’s standing in their way? Then, think of a story which lets them see themselves in it because they relate to the Hero, Goal, or Obstacles.

If you’re talking to a prospective customer, think of another customer who faced similar challenges and how your product or service helped them.

If you’re speaking to a struggling team, draw on an example of when another team you worked with overcame similar barriers.

If you’re trying to get your boss to see you as trustworthy, speak to a time when you proved your mettle in a similar situation.

When a story is relatable, the audience feels more connected and engaged.

Mistake #3: The Story Lacks Emotion

One of the reasons story is such a powerful means of communication is because it engages the listeners’ emotions.

In his book, The Happiness Hypothesis, social psychologist Jonathan Haidt describes how humans are only moved to action if both the logical side of their brains and the emotional side are engaged. Emotions provide the power and muscle needed to move from “a good idea” to a practical action.

Stories, by default, engage the emotional side of a listener’s brain. When you describe a customer who really wanted to hit a revenue Goal (anticipation) but hit an Obstacle (frustration) only to find a possible solution (hope), you help the listener feel something.

But if you were to tell this story in a way which undercut those emotions and made it into more of an exercise in logical progression, you’d undercut the very thing—emotional engagement—that makes stories so powerful.

It’s natural to think, in a business setting, you want to avoid over-rotating on emotion for fear of coming across as overly dramatic. That’s fair. But such concern often causes communicators to end up swerving way too far the other way by removing all emotion from their stories.

Lean into emotions. If the customer was excited, tell your audience they were excited. Show excitement on your face as you tell them. If the team was afraid, talk about their fears and let us know how they really felt. If there was relief once a solution was discovered, make the audience feel relief.

Emotions help logical decisions become reality. Don’t overlook them when telling a story.

Mistake #4: The Story is Too Long

Smart storytellers understand that while stories are engaging, they don’t need to go on forever. If they go on too long, even engaged audiences get impatient. Stories must end. Perhaps the group most in danger of missing the value of your well-told, but overlong, story are busy executives.

Busy executives want information quickly. This doesn’t mean they’re immune to the charms of a well-told story, it just needs to be concise.

Stories which back up a point, bring a situation to light, or show a path forward are highly valuable to an executive, as long as they are sharp, to the point, and quick.

In a presentation given to a team, you might have five or ten minutes to spin out a long, engaging yarn. But not in a meeting whose guest list includes the fast-moving boss. And definitely not in a one-on-one, quick-hit conversation with them.

So what do you do? Avoid telling a story? No! Tell your story, but tell an abbreviated, low-on-detail version. Don’t overlook key elements of your story its foundational structure, just hit your beats with no fluff.

Sharp and efficient storytelling will make busy executives take notice.

Mistake #5: The Story is Untold

All the teaching and instruction about the importance of storytelling in a professional environment, the key elements of a powerful story, and how to structure a story well are for naught if a communicator doesn’t ever tell a story in a business setting.

Change is hard. And changing the way someone communicates is doubly hard. We all have habits and default settings which are comfortable to us.

Stretching ourselves by working on something new doesn’t come natural to most human beings. By its very nature, the unfamiliar is… well, unfamiliar. But if you’re going to become a better communicator, you must challenge yourself to improve your communication techniques and add new tools.

For many people, storytelling is an unfamiliar communication tool. It’s new, it’s different, it feels hard… and, because of all of that, many people opt not to tell stories.

When you choose not to tell a story in a situation which could benefit from one, you’re not only doing your audiences a disservice, but you’re also doing yourself a disservice.

Conclusion

As Steve Jobs said, “The most powerful person in the world is the storyteller.” When you go out of your comfort zone and take on the role of storyteller—in a sales conversation, a team meeting, an update, a one-on-one with the boss—you flex your communication muscles and become a more powerful human.

Yes, it’s possible to make mistakes when telling a story. That’s true. But don’t let fear of those mistakes stop you from taking risks, discovering the right story to tell your audience, leaning into that story, and delivering it in a way which inspires your audience to act.

In the long run, your audience will thank you for telling a story well. And you’ll thank you, too.

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Illustrated by Trami Truong