Storytelling for Non-Storytellers

Last month, I heard a fantastic story from a friend about his two recent vacation encounters with Barack Obama on different golf courses in Hawaii.

This particular story had all the ingredients of a slam dunk: a once in a lifetime coincidence (he had no idea Obama was playing golf that day), another once in a lifetime coincidence (“and get this!” – he ran into Obama again the next day), and finally a moment of suspense (“Did he remember you from your first encounter? Yes he did!”)

I’m happy to say that my friend Brian (his real name) told this story well on every occasion I asked him to repeat it to our friends. Go Brian!

But perhaps you consider yourself a person that, even when all the ingredients are there, can’t seem to get through the slam dunk story. I feel for you. I’m the guy at the table that’s still listening, even when everyone else has abandoned you. “And then? And then? You can do it!”

Everyone has a storytelling voice. I’ve even gone into detail before on some specific tips for finding your storytelling style. But when it comes to telling a story to an informal audience, there are a few ways to shoot yourself in the foot before the story even gets started.

Hedging – “It’s not really that funny, but here we go.”

By tempering your audience’s expectations, you’re giving them permission to tune out from the onset. He said it wasn’t that funny! So, I’m gonna check my phone…

Some of the most entertaining storytellers I know tell absolutely horrendous tales, but it’s their ability to convince us a payoff is coming that keeps us tuned in.

Most of the time, especially with strangers or loose acquaintances that aren’t familiar with your stories, people will take you at your word when you say a story’s not that good.

The Handoff – “No, no, you tell it. You tell it better.”

This usually happens in couples and tight knit friend groups. The original storyteller is brutally aware of the fact that a more engaging storyteller at the table knows the same details and thus should just take over.

In improv comedy, one of the core tenants is to act like you know what you’re doing, even if when struggling onstage. If the audience perceives that no one is at the steering wheel, there’s an elephant in the room: we know you’re floundering right now. It’s uncomfortable and avoidable (especially with strangers – with friends it can be kind of funny).

The handoff usually comes after some hedging. Often times, the original storyteller wants the story to be told regardless if he or she is the one to tell it. In that case, it may just be better to start off by saying “someone tell the story the story about Obama in Hawaii,” and usually a friend will jump in.

Note – the handoff is different from the hijack. In every group of friends, there’s the person chiming in to add details or interrupt, until eventually he or she takes the reins. Sometimes this works great (like a play-by-play paired with a color commentator), but it’s usually uncomfortable and worth a discussion offline if it’s a recurring problem.

Context – “Is this story right for the situation?”

When out with a group of friends, the max length of an engaging story is about 5-8 minutes. To know how long a story will take you to tell effectively, it’s important to ask yourself, “What’s the context?”

If you want to tell a story from a golf summer camp when you were a kid, that’s probably fine if you’re out with other golfers or people that went to summer camp. The context of summer camp and golf is already “installed,” so you don’t have to do the legwork.

If you’re out with a bunch of coworkers that haven’t done either, you’ll find yourself trying to explain the game of golf (good luck!) and describe a summer camp setting before you even get to your story. By that time, attention spans will have run dry.

Avoid longwinded stories by acknowledging the contexts you share with your audience. Or, tell a story to introduce a context, and build off of that story to introduce the next one later.

Lastly, often the context doesn’t matter! Your friends will probably be shouting, “Get on with it!” because it’s not important to know the context to enjoy the story.

Enjoy your next happy hour with these new thoughts in mind.

Chris Severn delivers corporate trainings through improv comedy techniques for organizations in the Bay Area. Visit  or email to schedule a an introductory class.