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The 3 Reasons You’re Not Good at Telling Stories

by Hanna Brooks Olsen
featured, money & life

It’s happened, at least once, to everyone: You’re talking to someone, maybe at work, maybe at a social gathering, and you start to tell them a story. Then, about midway through, you realize you’ve made a terrible miscalculation. Your story isn’t endearing them to you, it isn’t making them laugh — it isn’t doing much of anything. Or maybe you’ve sat down to write a blog post for your small business, and you’ve got a story that you know is great — it’s your business’s origin story, or the tale of a time when you had a really great instance of customer support. And as you’re typing away, it hits you that this just isn’t as great as you thought it was.

What went wrong?

The human brain likes and even expects a good story. As Vanessa Van Edwards points out, MRI scans have shown that when people hear stories, their brain “lights up like they’re the one in the story.”

“We actually feel like we’re there,” she explains, and even begin to map out or figure out where we think the story is going next. A story that doesn’t seem good, then, is usually one that doesn’t live up to our expectations.

how to tell better stories


“There are some very basic parts to [a story,]” explains podcaster and public radio storyteller Alex Blumberg. “It’s a sequence of actions. Once we hear actions in sequence, we are sort of wired to listen to them, at least for a little bit. If it goes on too long, we lose interest. Or if they don’t go to an interesting place, we lose interest.”

The differences between a good story and a bad story — or maybe a good story and a non-story — usually come down to two elements: Content and delivery. Basically, if your story has a ton of great details, but the method of telling isn’t ideal, it won’t be interesting or compelling. And if your story doesn’t have great details, or you don’t know which details to highlight, it doesn’t matter how good the telling is.


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So how do you get better at telling stories, whether in writing or verbally? Alex has a very simple equation for framing a story, and it works in almost every instance. Just treat your story like an algebraic problem and solve for the unknowns.

His equation is: “I’m telling a story about X, and it’s interesting because Y.”

By asking yourself what the main subject and element of interest in your story are, you can begin to fill in the details, and make sure you tell the story in order, with all of the most relevant parts highlighted. Consider which details are surprising, delighting, intriguing, and which are nonessential, superfluous, off-topic, or plain boring. Then, diagram the story to make sure everything is in the right order.

Especially important, says Alex, is what he calls “the punchline,” or the conclusion of the story.

“It has to resolve into something,” he explains. The ending needs to either be satisfying, or unexpected, or humorous, or insightful — but if your story just ends, your audience will wonder why you told it at all. And often, that’s where a story really breaks down — the person telling the story or writing it started without actually deciding on the important details, including what the end point will be.

“The biggest mistake I see people making is they tell the punchline first,” says Alex — something that can easily be avoided

And if you’re really worried that your story won’t pass muster, borrow a trick from Vanessa — end your story with a question. That way, you ensure the conversation continues, and gives your audience the signal that it’s time for them to share their stories.

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Hanna Brooks Olsen

Hanna Brooks Olsen is a writer and editor for CreativeLive, longtime reporter, and the co-founder of Seattlish. Follow her on Twitter at @mshannabrooks or go to her website for more stuff.