How to be a better storyteller


Chris Walters

Chris Walters

Blog author Chris Walters

Chris Walters writes for Policygenius, a digital insurance brokerage trying to make sense of insurance for consumers. He previously wrote for The Consumerist.

Published July 31, 2014|3 min read

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If you want a real-world example of that cognitive blind spot where a person is too incompetent at something to know better (aka the Dunning-Kruger effect), look to your group of friends and family. Which one among them can't tell a good story to save her life? There's your Dunning-Kruger; the reason she's terrible at stories is because she has no idea she's terrible at stories.Of course, if none of your friends is terrible at storytelling, then you know what that probably means. But either way, it's likely there is someone in your life (maybe you) who hasn't mastered the art of entertaining others with a story.It's the chucklehead whose PowerPoint presentation seems to last 6 hours instead of 6 minutes. It's the wedding guest who brings the reception to an awkward standstill. It's your dad on the phone.There are plenty of books available that will try to teach you how to tell a good story, but save your money. If all you want to do is make your stories less painful to sit through, you just have to break a few bad habits and keep in mind a handful of simple rules.So whether you need to forward this to a friend (or parent), or read it by yourself in secret shame, here are some guidelines on how to avoid telling a disastrous story.


Or, how to make your stories not terrible, at least

  • Keep it short.Nobody likes to sit through a long story. Nobody needs to sit through a long story. If you can't tell it in less than 3 or 4 minutes, and you're not the narrator of "The Princess Bride," then you're probably telling too much story. Find the main narrative arc—the setup, the conflict, and then the resolution—and save everything else for future stories.

  • Don't get hung up on details.One of the most common traps of storytelling is the dreaded "forgotten detail"―the name that you can't quite recall, or the exact phrasing of one of the participants. Never interrupt the story with something like, "What was her name again?" Your listener shouldn’t have to answer questions before she can hear the entire story.

  • Tell one story at a time; NEVER link or nest stories.Some people think storytelling should be the verbal equivalent of Katamari Damacy, where you grab your suffering listener in a bear hug and roll all over creation accreting random junk.

This is the single worst rookie mistake you can make, and because humans are too polite, nobody will tell you that you are a horrible person for taking them down a cascading wreck of half-stories for 45 minutes.Remember: We are not trapped in an inception. Your story is not part of the Arabian Nights. You are not Sally Menke. Seriously, I cannot stress enough how annoying this habit is. People cringe you when you start to "tell" a "story" because they know they will never hear the end of any one story, but they will hear the beginning of, oh, seventy or eighty.If you ever hear yourself saying, "Oh that reminds me," in the middle of your story, just stop talking immediately. The only thing it should remind you of is that you are a bad storyteller.

  • Never wait for a reaction.You might be tempted, if you have a story that you think is particularly strong, to pause at the important parts and wait for the anticipated verbal response from your listener. Don't do this. Even if you know in your heart that your next sentence deserves a shocked "oh no you didn't!", you should tell your story as if you aren't aware of this. Listeners can pick up on it when you anticipate their reactions, and then they'll become self-conscious and freeze up.

  • Tell your story in one go.Your story is not an HBO series.

  • Make sure your story has a good ending.If you're going to make your listener sit through an entire story, you'd better have a good reason why by the end of it. Careless storytellers will sometimes start to tell a story because they think it has an interesting beginning, but they won't take a moment to visualize how they plan to end it. This can lead to hurt feelings all around.Here's a recent example from my own life that will illustrate the pitfall of the weak ending:

Start of story (addressed to office mates): "Yesterday when I left here I was so wound up, and I saw that bar across the street and thought about how delicious a beer would taste."End of story (a few seconds later): "But then I just went home."

I actually told that story, and now the people in my office don't like me anymore. Here are some go-to endings that are proven winners with listeners. Try to work them into your stories.

  • A comeuppance - You learn the hard way why you shouldn't have done x.

  • A twist - The story is heading towards ending x, but then you explain why it's really all about y.

  • A lesson learned (aka an epiphany) - You have a profound realization that will impress the listener.

Note that if you're preparing a story for a business audience, you can reframe both the comeuppance and the lesson learned as "customer insights," and you will be praised for your innovative synergy of the quarterly monetization.


Or, training for The MothIf you can master the techniques above, you'll be able to tell a halfway decent story in almost any situation. But if you master the techniques below, you'll be able to captivate an audience the way a hungry cobra hypnotizes a shoebox full of mice.

  • Watch your listener and adjust your story accordingly.Some listeners will pay rapt attention to you and ask for more and more story. They are ravenous. Others will settle in with a sort of "oh boy" sigh at the very start, and watch you through half-lidded eyes. Adjust the length of your story based on the type of person listening to you.

  • Maintain velocity.Good storytelling is a sort of verbal bobsledding. A good story need not be brief, and it also doesn't have to be told at a breakneck pace. But it should move briskly and have a lot of energy behind it, and maybe feel a bit reckless at certain points.

  • Stick with comedy unless you're a professional or an inspirational speaker.(And actually, the best inspirational speakers tend to use comedy, too.) In most areas of life, comedy is harder to pull off than drama. But when it comes to casual storytelling, you'll find that most people want to laugh and will try their damnedest to have a good time with you.


Finally, here are some optional techniques that can help you turn a "ha ha, that's cute" story into a "wtf? that's awesome!" story.

  • Never describe your dreams unless they meet the following conditions:

  1. The dream can be told in less than ten seconds, and

  2. One of the following elements is part of the dream:

  • sex with a celebrity

  • cannibalism

  • Don't tell dad stories (or mom stories).In my family this means don't just repeat the story a second time in an attempt to get a stronger reaction from your despondent listeners. In other families it may mean you shouldn't use catch-phrases over and over, or it may mean you need to stop bringing everything back to the topic of grandchildren and why you hunger for them so. The only thing your story needs to do well is entertain the listener. If it's not doing that, find a better story. And tell it better.

  • Avoid the topic of death in most situations.Don't tell stories that involve death unless you can make them (a) cartoonishly shocking or (b) so bizarre that they cease to feel realistic.For example, I have a story about a dead cat. I don't tell that story, because it grosses people out and makes them sad. But I have another story about a birthday pony who died because of a sweet elderly couple, and that story I do tell, because it's so outrageous that people forget all about the death part and just marvel at the rampant absurdity.

  • Don't Kanye your story.Never make yourself the hero of the story. First of all, it's probably untrue, and second of all, nobody likes to hear all about someone else’s happiness. You can’t root for a character if her life is already perfect.

  • Don't repeat yourself (if you're called out on it).If your listener says something like "You've told me this" or "Oh I read about that" then immediately stop telling the story. Your inclination will be to go ahead and rush through the rest of the story anyway, as if your listener still needs to be reminded of what it was about. But she doesn't, because she already told you that she remembered it.

  • Do share things that are inappropriate―but not offensive!An easy way to spice up a story (while also protecting yourself from the Kanye trap) is to overwhelm the listener with unexpected details that no normal human being would consider sharing publicly. These details can include: public arrests, disastrous first dates, and overactive neuroses. Read older David Sedaris pieces for perfect examples of inappropriate details.

So at your next book club party / meeting with your parole officer / blind date, try out these storytelling tips and enjoy the social rewards.

Photo: Teymur Madjderey