Esther Choy on How Leaders Can Get Better at Business Storytelling

We’ve all been there.

It’s Friday afternoon, the sun is out, people are getting ready for the weekend, but instead of enjoying the weather, you’re sitting in a stuffy conference room looking at numbers on a chart.

You look down at your watch for the fifth time in as many minutes and wonder why time seems to go so slow. There’s a bunch of numbers on the chart in front of you, but none of them seem to make sense. You hear your colleague talk, but it’s becoming crystal clear you’re going to forget everything about this presentation the moment you leave the room.

Whether we like it or not, businesses are built on storytelling. You need stories to keep your team motivated. You need stories to make prospective customers envision what it would be like to work with you. You need stories to make people care.

Facts and data are just half of the equation. If there is no meaning behind them, they’re useless. And that’s where storytelling shines. A good story weaves facts and data together in such a way that it’s clear and memorable.

Of course, knowing that storytelling is important and doing it are two completely different things.

That’s why we talked to Esther Choy, founder and president at Leadership Story Lab, during our Business Storyteller Summit. She explained to us how organizations can create a story that persuades people.

In this article, we’ll explore the elements of a good story, how to get better at storytelling, and the common pitfalls you should avoid. If you want to listen to the talk you can do so here:

The elements of a good story

Committing yourself to get better at storytelling is daunting. Still, it’s such an important skill to learn if you want to draw attention to your brand. Media outlets, influencers, your team, and your target customers will resonate with you better if you get this down pat. What makes it challenging is that there just aren’t any clear cut rules. There are, however, a couple of elements that need to be in every story.

“The most important thing is a sound story structure,” Said Esther. “Just remember this: I.R.S. It stands for intriguing beginning, riveting middle, and satisfying ending. If you remember this structure, you’re 50% there.

Each story, no matter how simple or complex, goes through that structure. A story without an intriguing beginning is uninteresting. A story without a riveting middle is boring. A story without a satisfying ending is frustrating.

After you have the basic structure in place, you need a theme. Without a central theme, your story will be all over the place and people won’t know what to take away from it. A theme can be as simple as saying what it’s about in a sentence or two — as long as it’s succinct. Or as Esther said:

You have to be able to say it in one short sentence. If you go on and on for paragraphs and paragraphs, that is not a theme.

Lastly, every story needs a challenge and a change. What difficulties did you have and how did you overcome them? Esther said: “I’d like to say challenge is the nerve center of a story. And change is the soul of it.

Now that we know what makes a story tick, let’s look at some ways we can practice it.

How do you get good at telling stories?

The short answer is: by doing it.

No course, no matter how good it is, is going to magically baptize you and turn you into a good storyteller,” Esther said. “So instead, ask yourself every single day, ‘what is one thing I can practice to become a better storyteller’. And I guarantee you, even after a month, you’ll be much better.

Our days are filled with opportunities to become a better storyteller. However, they’re not always obvious.

“Everywhere, every day, there are countless opportunities for us to tell stories,” Esther added. “The key is that you might not be asked explicitly: ‘Hey, tell me a story.’”

Instead of telling your boss all the facts in chronological order, tell them a story that encapsulates the commitment, the challenges, the setbacks, and ultimately (or hopefully) the triumphs you have achieved.

Another moment where you can practice storytelling is sending emails. Sending emails in particular is a good way to practice storytelling because it’s a quick way to go through the entire framework. Emails have a central theme (why are you sending an email in the first place?), they have a beginning ( the subject line), a middle (the first few lines), and an end (the last few lines).

Instead of writing an email and hoping the other person reads it, spend some extra time thinking about how you can add a little surprise and suspense to the subject line. Especially with people you work closely with, you can ask them if they are more inclined to read the email once you put more suspense in it.

Besides directly practicing it, a good habit that’ll make you better at storytelling is collecting other people’s stories. At first, this seems a little counter-intuitive, but hearing other people’s stories helps us improve ours. Esther remarked:

Otherwise, what’s coming from you will tend to be all from a similar point of view. If you incorporate other people’s stories and other voices, that’s going to enrich your stories.

We all have our own way of looking at the world, our own experiences, and our own way of thinking. Only engaging with your own stories will cause them to have the same angle every time.

Not only that, but listening to your customer’s stories, for example, can help you create better website-and email copy, blog posts, and sales pitches.

Esther recommends asking other people questions that can lead to a good story.

Here’s another thing that you can practice. What is one great question that I can ask today that gets other people to tell me their stories?

Stories are everywhere if you look for them. Stand up comedians, copywriters, authors, all of them tell stories for a living and can help you create more suspense or make stories more surprising. As an example, just look at these opening lines from famous books:

  • It was the day my grandmother exploded. (The crow road by Iain Banks)
  • All children, except one, grow up. (Peter Pan by J.M Barrie)
  • It was a bright cold day in April, and the clocks were striking thirteen. (1984 by George Orwell)

Those first lines sold millions of books. How can you not continue reading after that? What do you mean ‘Thirteen’? Which child didn’t grow up? What shenanigans did grandma pull to get shot to the moon? All of these first lines teach you how suspense and surprise can pull you into a story.

Or listen to Dave Chapelle’s Unforgiven:

If you take the story element out of it, Dave walks you through quite ‘normal’ situations. Another comedian ripped off a joke, executives got him a bad deal, and he wants to get paid. But the way he manages to take you through the story is masterful. Before you know it it’s over and you’ve been listening to him talk for 20 minutes.

Collecting examples and seeing what makes them tick will help you improve your own stories. Now let’s look at some mistakes to avoid.

Common storytelling pitfalls.

One of the things that makes storytelling so difficult is that you can lose your listeners in a heartbeat. One second they’re listening, the next their eyes glaze over and it’s like talking to a wall. So how can you tell a story without losing people in the process?

Esther identified 3 major pitfalls when telling a story:

The number one mistake storytellers make is they try to show their audience how much they know, instead of helping the audience get to their needs.

This often happens in business environments. A presenter will throw around big words and jargon to impress the colleagues around them. But instead of being impressed, they end up being bored and confused. No one has ever complained something was too easy to understand, so it’s best to keep your language simple.

“And number two, there’s that inherent burden of proof that we have to prove we’re the best. At least we’re much better than our competitors, instead of explaining how we serve you best.”

Both of the first two pitfalls boil down to the same thing: you’re not thinking of what other people are getting out of it. The presentation is all about the presenter. Instead, we can learn something from copywriters. There’s a saying in copywriting that people only listen to radio WIIFM (What’s In It For Me). Keeping this in mind while you’re creating your story will make it more focused on your audience and make it much more interesting for them.

The last mistake is that there’s this inherent burden to feel like you have to be thorough, instead of being intriguing and informative.

This one has more to do with not being able to prioritize what information people need and what can be omitted. This, in turn, comes from not knowing what information your audience actually needs.

If you know your audience, if you know what level of skill they have and what they’re experiencing, you can tailor your presentation to give them enough information to be effective, but not so much information they get bored or overloaded.

Easy to learn, hard to master

The basics of storytelling are simple, but they can take a lifetime to master.

Instead of waiting for the perfect moment to tell a story or until you come up with a new Marvel movie, try to incorporate the basics into your everyday life. You’ll progress much faster, you’ll increase your results, and you’ll have more fun doing it. The world needs more storytellers.

If you want to learn more about Esther you can read Esther’s book. Or check out some of her free resources aimed at helping leaders become better storytellers:

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