The Power—and Danger—of Storytelling in Leadership

The most charismatic leaders, from Chesky at Airbnb to Kalanick at Uber, invested as much in their stories as in their products. They crafted origin myths—moments at design conferences, desperate nights gluing cereal boxes, breakthrough conversations over ramen—that helped orient new recruits, rally investors, and galvanize users. But these narratives, while essential, often mixed memory with legend, sometimes bending facts for dramatic effect. Author Brad Stone, tracking and interviewing these leaders, noted how the tale of ‘just needing to pay rent’ gradually became a story of global mission, and how tales of adversity—at times—conveniently downplayed the network, privilege, or lucky breaks that also mattered. Research in leadership studies warns that the strongest teams aren’t those with the most inspiring mythology, but those that balance compelling narrative with honest self-reflection. Too much mythmaking distances leaders from their teams and reality, eroding credibility over time.

In groups large and small, having a story that binds is crucial—but always weigh the drive to dramatize against the value of trust. Reality, including the messy parts, is often the most powerful connector.

Write your journey or project’s story with pride, but then share it with a candid friend or group and ask them to flag any parts that sound exaggerated or one-sided. Check your impulse to hide the awkward chapters—sometimes, these make your story more useful and trustworthy to others. In meetings or essays, try highlighting turning points where things went off script before things turned around. This makes your message both more powerful and more authentic.