The Lost Art of Storytelling
How Great Leaders Win with Narrative
When I was 13, my father took a job for a year on Long Island. He stayed with my grandmother during the week and came home to Boston on weekends. On Sundays, we’d catch up while wandering through a neighboring town eating ice cream - his way of bridging the gap between a teenager who knew nothing and a man who’d seen too much.
It was on those walks that I learned the power of storytelling.
He’d talk about childhood weekends at Coney Island with his aunts and uncles, including a memorable one when a pigeon relieved itself on his giant swirl lollipop - trauma that, by his account, took years from which to recover. Or the time a sleepover turned into a police search for a missing child (and the near demise of his Aunt Frances). My then-five-year-old father was later discovered out of sight, wedged between the bed and the wall.
His stories were absurd, human, and unforgettable.
Through them I learned macro-lessons: pursue what you love and can excel at and micro-truths, like the virtue of keeping spare nuts and bolts in old pickle jars “just in case.” Storytelling, I now realize, was how he made sense of a life that had seen antisemitism, war, economic struggle, and joy all in equal measure.
Today, we live in a world that prizes analytics over anecdotes. Leaders weaponize dashboards, and shy from motivating dialogue. Yet the HBR shows that up to 70% of CEO-led change initiatives fail, often because employees can’t see themselves in the company’s story. Data explains what is happening. Narrative explains why it matters to people.
Even my father, an electrical engineer in the emergent age of mainframes, understood this. He could describe a CPU in a way that made you want one as a best friend. He knew a good metaphor could light up the brain faster than a schematic.
The same holds for business today. Whether you’re launching a new strategy, merging cultures, or pitching investors, success lies in the story you tell. It’s what connects logic to emotion, turning information into conviction. Yet in too many boardrooms, lengthy jargon-filled PowerPoint has replaced plot.
A compelling narrative has structure, characters, conflict, resolution and a rhythm that guides people through it. Narrative invites participation. It lowers defenses. It encourages behavior change.
There are some tricks to doing it well.
Pick an archetype. Is yours a Hero’s Journey? Rebirth and Renewal? Every transformation needs a dragon to slay: competition, complacency, or complexity. Frame it clearly.
Set the scene. Give context. The market, the moment, the stakes. Without it, your audience can’t locate themselves in the story.
Map it out like a comic strip. Draft it with a Sharpie Marker on the back of recycled paper. Pin it on the wall. Check the flow.
Create “expectation violations.” Surprise people. Start in the middle of the action, drop a provocative fact, use a visual twist, or try a six-minute PechaKucha instead of a sixty-minute monologue. Attention follows novelty.
Understand your characters. Who’s the audience? How will the story resonate? Is there something to satisfy everyone?
Rehearse like a performer. Great storytellers aren’t born; they’re practiced. A writing or acting coach can build presence faster than another AI workshop. PhD students would chew the eraser off their #2 pencil for the chance to teach.
Storytelling is equally critical in the world of social media. Instead of the obsession with “hyper-personalization” think about your brand story; with LLMs now driving visibility, your brand needs a narrative arc, repeatable assets and threads that tie them together. Take a page from Duolingo (who staged the death of its mascot), or Apple’s Shot on an iPhone spots, some only :05 seconds long. Stories needn’t be long to make us take notice. Iver’s thrifty half-second Superbowl ad in 2009 was the ultimate expectation violation.
Storytelling isn’t just a tactic; it’s a critical business skill. It shapes culture, motivates behaviour change and creates believers. It can be what my friend and former business partner Angus Tucker calls storyselling. When done well, it can turn a quarterly update into a call to arms.
My father loved stories almost as much as apple pie. He devoured both voraciously for more than nine decades. But in the end, irony got the last word. One evening he stumbled on his way to the kitchen for a second slice. We always knew the pie would get him.
With his dark sense of humour, he would have appreciated the punchline.