Storytelling for Speakers

Stories are the speaker’s most powerful communication tool, but how does storytelling work? Why do some stories connect while others don’t? I share the answers in the video from my February, 2020 workshop on storytelling and in the text below.

When I was a young man still in college, I found myself—quite through happenstance—in the company of an odd band of folks who lived aboard their sailboats in the free anchorage in Miami. The stories they told about harrowing adventures in faraway places captured my interest. Up until that time, I’d been a private prep-school student headed toward some sort of advanced degree and the career that followed, but when I realized that stories of adventure at sea were not just the stuff of books and movies, I resolved to find stories of my own. Thus began my storytelling journey.

Stories inspired me, and the secret floating village of Miami’s Dinner Key anchorage was a storybook Steinbeck himself would have envied. I took notes and photographs and began to develop my “story consciousness.” I didn’t know exactly what stories were, but I made it my business to look for them. My first big realization was that no matter how grandiose the setting or how severe the storm, stories are always about people. This is the golden rule of storytelling. Put colorful people in a colorful setting and give them colorful things to do, and you’ve got stories to tell. Take away the people and you’ve got nothing. If a tree falls in the forest and there’s no one around to hear, does it make a sound? No.

Not long after graduation, I found myself on a tiny blue sailboat in the middle of the Gulf Stream en route to the Bahamas. Over the years, I made several Gulf Stream crossings, spent thirty-eight days transiting the North Atlantic, ran aground, battled storms, speared fish on the reefs, anchored in the lee of tranquil islands, climbed an 8000-foot volcano, met wonderful people, experienced deep solitude, got seasick a few times, and returned home.

But having voyaged in search of stories and found them, I still wasn’t sure what a story was. I knew that stories were about people, but I also knew that stories ran deeper than journalistic accounts of who, what, where, when, and why. I worked in a number of disciplines and wrote a number of books before I solved that mystery.

If you’re talking about prices, processes, ingredients, and data, you’re not talking about people.

If you’re not talking about people, you’re not telling stories.

If you’re not telling stories, you’re not connecting.

If you’re not connecting you’re not selling.


Yes, whether you’re offering a product, a service, or an idea, you’re selling. Trying to get a kid to go to bed? Selling. Trying to get a new job? Selling. Trying to get that attractive person to say yes? Selling. Trying to get an audience to embrace your message? You get the idea.

A story is a metaphorical boat that sails from the rocky, stormy seas of conflict to the safe port of transformation. Whether it’s Cinderella finding “happily ever after” or a business coach challenging her clients to understand their value and charge what they’re worth, the story is about the outcome—the transformation.

Storytelling Elements - Conflict and Transformation

For the story to engage—for the boat to make the passage—the water has to be deep enough; the conflict has to be authentic. Whatever boat you choose must be a metaphor for your listener’s story. We care about Cinderella because we all want to find our prince or princess. We all want to be loved for the subtle, nearly invisible things that make us who we are—our walk—that glass slipper that fits only us. The Cinderella story is authentic, even if it isn’t true or plausible.

Storytelling Elements - Authenticity

To make the crossing, the sailboat needs wind—an invisible, powerful force—magic. Cinderella had her fairy godmother, but perhaps you’re a business speaker who can transform the culture of an organization in forty-five minutes. Do you teach autistic children to speak or shoot photographs that transport viewers to other worlds? Do you invent drugs that save lives or play music that makes people dance? Are you great at math or chemistry? Do you make wine or cook transcendent meals or show people how to climb mountains…? You get the idea. Magic is quite real; it’s no more confined to the realm of books and movies than adventure is.

Storytelling Elements - Magic

I call this model StorySailing.® A story is a ship full of people that’s pushed from conflict to transformation through the deep waters of authenticity by the winds of magic.

How do you put StorySailing® to work? We all have to learn to navigate and trust our compass. We all deal with storms and calms and mechanical breakdowns, and we run aground sooner or later. As a captain of industry, you learn about leadership. It’s up to you to keep things shipshape. Everything that happens on your ship is your responsibility, even if you’re not the one who messed it up.

Your story—whether it’s a climb to the top of Mt. Everest or a trip to the grocery store—is a metaphor for your listeners’ journey. Find your story, discover your magic, understand your audiences’ authentic problems, and deliver the transformation they’re looking for.

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