3 leaders who effectively use storytelling to transform

Written by

Jeff Davenport

Great leaders rely on varied communication tools to inspire their teams and influence others to take action. But there’s one powerful persuasive tool execs are often reluctant to use: telling personal stories.

Instead, when leaders give a presentation or speech, they’re quick to turn to impressive stats and industry news to persuade. Those same leaders struggle to tell stories of their first-hand experiences even if they know it’s the best way to connect with customers, employees, and shareholders.

Leaders shy away from storytelling because the inherent nature of a story incorporates hardship. In the three-act story construct, the second act is messy. It’s full of challenges, roadblocks, and desires the protagonist must overcome—and sometimes, they fail.

It can feel counterintuitive for a respected leader to admit faults or flaws, since they think it could undermine their credibility. But accounts of failure inspire people and research shows audiences are moved by tales of overcoming setbacks.

While many leaders hesitate to use personal anecdotes, the ones who do see great success. Here are some of the leaders who’ve most successfully found the courage to show their true selves in talks in order strengthen presentations and inspire their organizations with storytelling.

Howard Schultz

Ask any presentation expert who one of the best storytelling executives is, and they’ll probably say former Starbucks CEO Howard Schultz.

Schultz regularly returned to his own rags-to-riches origin story—he was the child of often unemployed parents in Brooklyn public housing who went on to become the CEO of the world’s most successful coffeehouse chain. He’d use the story as a starting point to describe the history and mission of Starbucks and to explain many decisions he made regarding the company.

Schultz regularly framed Starbucks’ company values and direction in a story about his father having an accident when he was a young boy. Seeing his father injured and unable to work inspired him to launch a company that took care of its workers and provided them with benefits like insurance and adequate time-off.

By framing his business goals in a personal story about his own values, Schultz made his corporate mission comprehensible and he described his strategic decisions in a way which made sense to anyone listening.

Sheryl Sandberg

It’s hard to believe Sheryl Sandberg once felt reluctant to share her own personal tale of tragedy in her public speeches. Today, the Facebook COO masterfully delivers revealing, intimate stories in her talks, and these make her messages powerful and stirring.

One of Sandberg’s most effective uses of personal storytelling happened during her 2016 UC Berkeley commencement speech, after she tragically lost her husband Dave Goldberg to heart disease in 2015. Sandberg chose to harness the painful tragedy to deliver a talk which was profoundly affecting and inspiring.

She described her experience losing her husband, then explained how she was able to rise from her unbearable grief to become a stronger, more resilient person. She said, “…when life sucks you under, you can kick against the bottom, break the surface, and breathe again…you can choose joy and meaning.”

Sandberg’s exhortation was powerful and uplifting despite its origin in a tragedy. She figured out how to unlock the power of a personal setback story for a presentation message which inspires and drives forward movement.

Rowan Trollope

Five9 CEO Rowan Trollope regularly uses firsthand anecdotes in his speeches. These stories make him feel relatable rather than like an untouchable executive, because they show he understands the wants, needs, and impulses of listeners.

When Trollope was a leading SVP at Cisco, he delivered the 2016 Cisco Keynote at Enterprise Connect, and he opened the speech with the story of his first experience with weightlessness at the “Zero G Experience.” When his instructor warned him he would laugh when he was finally weightless (all people do), he resolved instead to remain stoic. However, once he was floating in the air, he burst out laughing uncontrollably—reminding him he was human, just like everyone who’d been weightless before him (even professional astronauts).

Trollope’s story not only showed his humanity and endeared him to the audience, it also gave him an understandable jumping off point to explain to listeners what he wanted to do with Cisco products. He wanted to create devices that delighted users, whether they were professionals in the industry or just picking up the technology for the first time.

Like his weightlessness story, most of Trollope’s personal tales are entertaining and full of humility. They work to demonstrate his humanness—taking him down off any executive pedestal and making him approachable and accessible. This results in a message which feels relevant and comprehensible to everyone listening.


If you’re a leader planning to deliver an important talk, consider pulling from your own cache of personal stories first. By centering your presentation around a tale which reveals something about who you are and what you’ve overcome, you can inherently build trust with your listeners, and encourage them to adopt new mindsets or inspire them to take action.


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Illustrated by Trami Truong

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