6 Rules For Great Storytelling, From A Moth-Approved Master Of The Form

Moth storytelling champ Margot Leitman has been hired by Facebook and others to help them learn how to spin a yarn. These are her rules.

6 Rules For Great Storytelling, From A Moth-Approved Master Of The Form
[Photo: Rebecca Rotenberg; Flickr user CleftClips]

Some years ago, writes Margot Leitman in her new book, Long Story Short: The Only Storytelling Guide You’ll Ever Need, when she was an aspiring actress in New York, she was preparing to rush to an audition when she burned her neck with a curling iron. “It looked like a giant hickey,” she writes. “There was no makeup that could cover it up; I had to go with it.” She entered the audition room and explained away the burn–not a hickey, she said; her dating history had been terrible lately. The casting director asked her to explain, and she responded with a story about a disastrous recent date where the guy actually balanced his checkbook at the table.

Long Story Short: The Only Storytelling Guide You’ll Ever Need

She had the casting director laughing before she even read for the part. And a few days later, she got the call saying she got it.

It was a moment that crystallized for Leitman the power that stories can have. Soon, she began to shift her performing energies towards live storytelling. She established long-running storytelling shows and classes at Upright Citizens Brigade in both New York and Los Angeles, including a sex-themed show called “Stripped Stories,” and she’s won storytelling competitions several times at The Moth. She gives workshops at places like Universal McCann and Facebook, companies that reckon good storytelling is good communication, and good communication is business. She has taught, by her own count, thousands of students to date.

And now, with Long Story Short hitting shelves and screens everywhere, Leitman shares with Fast Company a few key lessons on storytelling from her book.

Lesson 1: Make People Root For You

“In everything from politics to acting,” says Leitman, “the way to get ahead is often to get people to root for you.” When starting a story, first quickly introduce yourself as a clear character: “I’m the type of guy/girl who . . . ” The next step will run against the grain of what you’ve been taught about how to present yourself. In interviews and resumes, you’re supposed to talk yourself up. But in storytelling, people want to root for an underdog. Storytelling is not pitching. “When people pitch themselves, I’m put off by that.” Puffing yourself up makes people want to take you down a notch. When Bill Clinton insisted he “didn’t inhale,” no one could let it go, reminds Leitman. But when Obama readily admitted to smoking in his youth, people commended his honesty and moved on.

Lesson 2: Have A Few Go-To Stories At The Ready

You should have a polished story or two in your repertoire. You never know when it’ll come in handy, says Leitman, pointing to a moment in Steve Jobs’s original iPhone keynote when the slide deck failed, and he sprung gracefully into a story he had at the ready. “I think it was a story he told socially a million times,” says Leitman. “Probably it worked socially, so he decided to tell it in front of the crowd. To me, it’s the most memorable part of that speech. Rather than talking about the components of the iPhone, he’s taking a moment that makes him human.”

Margot Leitman

Lesson 3: Stories Are About How You Felt

“It’s really not what transpired that makes a good story,” says Leitman, upending conventional wisdom. “It’s about how you felt about what transpired.” The “plot” of your story is almost irrelevant when it comes to making a connection with your audience. “It’s not a matter of, ‘We won the game.’ It’s, ‘How did you feel when you won? What did you believe was impossible that now suddenly you can do?’” A corollary of this: Stories can be about very small stuff, so long as the emotions involved are big. Leitman tells a story about wandering into a Whole Foods in the midst of a personal medical nightmare. The cashier invited her to donate to the Haiti earthquake relief, and an emotional Leitman signed over $50. “The cashier said, ‘Wow, you’re a really nice person.’ I started crying, ‘I am! I am! a good person!’” Though small in scale, the story always gets a laugh.

Lesson 4: This May Seem Obvious, But . . .

“Stories have a beginning, middle, and an end,” says Leitman. Yes, it sounds obvious, but in years of teaching storytelling, she wouldn’t repeat this fact if it weren’t necessary. Think about it: Have you ever been at a wedding and heard one of the toast-givers drone on and on, without focus? “A lot of people never get to the story. I don’t know why they can’t. But they talk and talk and never get to a point,” she says.

It might have something to with the fact that life itself is noisy; we drift around, we have trouble finding the thread. “But it’s something that can be taught easily,” she promises. Leitman herself somehow always had the lesson internalized, she says, telling about the 22-page journal entry she wrote about losing her virginity. She wrote about all the hours before the event, and everything after. “My God, it needed an edit. But I sort of got it even then!”

Lesson 5: Good Stories Are Universal

Your story needs to framed inclusively; there has to be something your audience identifies with. Leitman remembers a student who began a story, “So I went to Yale.” The story that came after was really interesting and funny, about being seized with paranoia that a car was following him. But his opener, “I went to Yale,” didn’t mean for most audiences what the student thought it did. For him, “I went to Yale” immediately communicated, “ . . . which is in New Haven, Connecticut, which has some dangerous neighborhoods in it.” But all anyone else heard was: “I went to a fancy exclusive school.” It was an invitation for most audiences to tune out. The lesson has an analogue in a term from tech and design: Try to think about the “user experience” of your story.

Lesson 6: Don’t Be Boring

Leitman doesn’t mean that your story shouldn’t be boring (though that’s true, too). She means you should stop living a boring life. This lesson should be taken with a grain of salt, because she believes that all of us who’ve been on this earth a few years have a trove of stories worth telling. Even so, why not use your newfound interest in storytelling to reconsider some of your risk-avoidant habits? “We get into a groove in life where we get scared of trying new things,” says Leitman. “You have to say yes to things that scare you, otherwise you won’t have a very story-worthy life. And the legacy that goes on after you pass are the stories people tell about you.”


She impersonates a eulogist fumbling awkwardly for something to say about the deceased: “She . . . really loved her DVR.”

Related: TV Legend Norman Lear Tells A Story About How He Busted Writer’s Block

About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal