What makes a great story?

I'm publishing,?The Perfect Story: How to Tell Stories that Inform, Influence, and Inspire, with HarperCollins this fall. At the end of each chapter are interview vignettes with different storytellers. They include what you might learn if seated next to the person at a dinner party.

Some of the interview vignettes include a co-founder of Sundance, an Executive Producer at The Moth, the TED Radio Hour Host, a former creative director at Pixar, a Physician, a Video Game Writer, an Advertising Executive, a Head of Data Analytics, a Neuroscientist, and a Museum Director.

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EVERYDAY LEADERSHIP

One of these interviews is with Drew Dudley . You likely have seen his “Everyday Leadership”?TED Talk when he describes a “lollipop moment.” If you are like me, you've adored Drew from the moment you saw the talk. If you haven't seen it, go watch the five-minute talk and become a member of the Drew Dudley fan club.

This story has won the heart of people all over the world. It's about an unintentional moment of leadership that changed the lives of two strangers. In under six-minutes, Drew tells a great story. I wanted to break it down and show you why.

GIVE A SETTING

Drew starts by telling the setting. He describes being at Mount Allison University in New Brunswick. This lets you picture a university setting – placing ourselves next to him. He sets the context with:

“On my last day, a woman came up to me and said, ‘I remember the first time I met you.’"

Now you know this is going to be good. People tend to say impactful things at moments of endings.

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WHAT IS AT STAKE?

"The woman describes being in her hotel room with her parents the night before starting at the university. She was overcome with fear and doubt, unsure she was ready to be there. Her parents encouraged her to go to registration the next day. If?she decided she couldn’t do it,?they would take her home."

Now you know what is at stake. This woman is describing her fears, discomfort, and doubt. You can appreciate this hard moment. It may have even triggered a memory of a moment filled with question?and doubt.

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?DETAILS AND DELIVERY

"The next day at registration, she feels overwhelmed. As she turns to tell her parents she wants to leave, a door flies open.

“You came out of the student union building wearing the stupidest hat I’ve ever seen in my life. It.was.awesome.”

You visualize Drew bursting through the doors of a student union, in a goofy hat, like he is about to take center stage in a play. Your brain begins to wonder, “What color was this hat? What made it stupid? Does it have a propeller on it? Is it the hat he is wearing in this video?”

Drew's adopts the woman's mannerisms through his cadence and punctuation. He draws you into the moment with his inflection on stupidest and his cadence on It.was.awesome.

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CADENCE AND PAUSE

"You had a big sign promoting Students Fighting Cystic Fibrosis and a bucket of lollipops. You were handing them out to people in line.

You got to me and stopped.

And you stared.

It.was.creepy.”

You feel yourself squirming as this woman did from the way he uses pauses between each sentence.?You feel like you are this woman, unsure what this man in the weird hat is about to do.

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TELL THE STORY WITH YOUR BODY

"You reached into your bucket and pulled out a lollipop. You handed it to the guy next to me and said, 'You need to give a lollipop to the beautiful woman next to you.

Both the woman and the guy next to her are immediately embarrassed and turn beet red.

The guy reluctantly took?the lollipop and just held it out like this…”

Drew acts out this moment in an exaggerated manner. He bows his head with his eyes glued to the ground, extending the arm that sheepishly holds the lollipop. Through his gestures, you picture this shy guy holding out the lollipop and willing the man in the weird hat to move on.

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UNEXPECTED EVENTS

"She felt bad for the guy, so she took the lollipop. As soon as she did, Drew looked at her parents and said, 'Look at that! Look at that! First day away from home and already she’s taking candy from a stranger?'”

Drew uses great vocal inflection and humor punctuating each word. You laugh at this unexpected moment. You also feel the wave of relief across the nervous students queueing to register.

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Everyone started laughing. The woman’s fear and doubt dissolved, and she knew she shouldn’t quit. She never spoke to Drew again, but when she heard he was leaving, she had to tell him this story.

She thanks him and starts to walk away. Then turns back and says, “’You should probably know this too: I’m still dating that guy, four years later.’

A year and a half later, I got an invitation to their wedding.”

A great story builds and releases tension. You learn the unexpected news of them dating and getting married. All because of this moment he created. The tension that was building throughout the story is released. You experience the awe that Drew felt being told this.

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“Here’s the kicker. I have no recollection of that moment. I’ve searched my memory banks because that is funny and I should remember doing it, and I don’t. That was such an eye-opening, transformative moment for me. To think that maybe the biggest impact I had on anyone’s life, a moment that had someone tell me ‘You’ve been an important person in my life,’ was a moment that I didn’t even remember.”

Drew throws you one last unexpected event by telling you he doesn’t remember this at all. You share his confusion about this incredibly important moment in someone’s life that doesn’t exist in any corner of his memory. Instead of coming to a quiet ending, you get one more burst of energy.

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THE TAKEAWAY

“How many of you have had a lollipop moment where someone said or did something that fundamentally made your life better? How many of you told that person they did it?”

There it is – the takeaway. Recognizing moments of impact and sharing them, especially as a leader. Drew could have included research on leadership and recognition or even described some leadership theories, but you wouldn’t remember his talk.

His story connects you to emotions around fear, doubt, humor, and recognition. His use of tension, specific details, unexpected events, gestures, pacing, pause, and inflection, immerses your brain in the three-minute story. He connects this feel-good story to a business context with the memorable term: “Lollipop moment,” making you think of when you’ve personally experienced or created them.

Great stories don’t have to be complicated. But they do need to engage the senses and emotions – even in business. Next time you tell a story, include unexpected events, specific details, and emotion. Create a lollipop moment for your audience.

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If you liked Drew’s talk, you will love his interview in?The Perfect Story! Welcome to the Drew Dudley Fan Club!

Grab the free “Lead with Story” Guide

Great leaders are often great storytellers. They know how to captivate, inform, inspire, and, when called for, entertain their audience. The problem? So often, 6 storytelling mistakes sabotage our ability to tell powerful stories. Learn how to spot and correct these 6 mistakes here.

Click here to learn more about my book, The Perfect Story: How to Tell Stories that Inform, Influence, and Inspire, publishing with HarperCollins in October 2023.