How To Tell A Captivating Story Like A Stand-Up Comedian

Want to be a better storyteller? Comedian and writer Ophira Eisenberg shares the secrets of how to connect with your audience.

How To Tell A Captivating Story Like A Stand-Up Comedian
[Photo: Flickr user CleftClips]

A story well-told is powerful. It grips us and keeps us engaged, then leave us somewhat changed–perhaps a little happier, more understanding, or determined–because of it. Good storytelling skills can be a powerful asset in business, helping you in every area from presentations to crafting a great rationale for a new project.


Ophira Eisenberg tells good stories. A stand-up comedian, radio host, and writer, she is a frequent host of popular New York City story slams staged by The Moth, a nonprofit dedicated to the art and craft of storytelling. She says the rise of social media has played a huge role in our renewed interest in storytelling.

“People want something more meaty than 140 characters,” she says. “So we go back to storytelling and maybe to revitalizing the human connection.”

Whether it’s about business or life, Eisenberg says good stories have several common elements:

1. Problem

A story hangs around a problem that needs to be solved and which involves some risk, Eisenberg says. Listeners perk up when they hear a problem that holds immediate risk, like when you lock yourself out of your house on your wedding day–and your dress or tuxedo is on the other side of the door.

As a business leader, you may be facing a crisis in your business or you may be trying to tell a story that mirrors a problem your customer is facing.


2. Vulnerability

Along with the risk comes the humanity reflected in the possibility of failure or loss. The subject of the story needs to face down some of the universal fears that we all have, since that’s what truly surprises people, she says. When you tell the story of eschewing the law career your parents wanted for you, or overcoming a big financial mistake from which it took years to recover, being honest about the challenges, fears, and failures you faced gives the story power.

“Vulnerability catches people off guard sometimes and that’s when they perk up a bit,” she says. “It’s a nice reminder of the human condition–that we just really want to connect. And the best way to connect is to showing your courage.”

3. Color

The story need details to set the scene–perhaps what you were wearing or how hot it was that day. But make sure that the details you include serve your narrative because it’s easy to try to cram too much in, and make your tale too long and convoluted.

Stories at The Moth events are typically five or 10 minutes. While the ideal length varies depending on the format, good storytellers know how to edit themselves for greatest effectiveness. Eisenberg says you have to “lose your darlings” sometimes to keep your stories tight and clear.

4. Truth

In work she’s done with corporations, Eisenberg says that nothing brings a room together like a leader telling a heartfelt story about a challenge he or she overcame. It might be accomplishing something important or bouncing back from a mistake, but she says people are drawn to those who share their personal truths with some emotional weight.


She says that hierarchies can cause us to forget that we’re all human and that everyone faces similar challenges. That’s where storytelling is a great equalizer and allows you to reach people in a powerful way, she says.

5. Resolution

To qualify as a story, your problem has to have a resolution, even a partial one. Otherwise, what you have is an anecdote, Eisenberg says.

An anecdote leaves you the same before and after. A resolution solves the problem and makes you different in some way. Sometimes, it takes time for the story to be fully formed, she says.

6. Growth

Good stories show how you’ve changed from the beginning of the story to the end of it, Eisenberg says. If you can show how you overcame your weakness and you’re changed because of it, you’re at little risk of your audience “zoning out,” she adds.

“Those are the stories we’re dying for,” she says. “Everyone has a weakness and everyone is searching for how to get over it–how to rise from the ashes and get over something. It is way better to talk about weakness overcome than strength that persists.”


About the author

Gwen Moran is a writer, editor, and creator of Bloom Anywhere, a website for people who want to move up or move on. She writes about business, leadership, money, and assorted other topics for leading publications and websites