Why Leadership = Storytelling

“The great storytellers have an unfair competitive advantage.” — Bill Gurley

Andy Raskin
Jan 24, 2017 · 3 min read

Leadfully (a service of SYPartners) recently published this Q&A about my work helping CEOs and leadership teams achieve better results through strategic storytelling. I’m reposting it here with their permission.

RASKIN: Leadership is the art of inspiring others to make a story come true. Therefore, if you’re leading people, you’re telling them a story — by definition. Of course, your story might not be connecting as deeply as you’d like, and that’s why leaders benefit from becoming better storytellers. As Benchmark’s Bill Gurley says,

The great storytellers have an unfair competitive advantage. They are going to recruit better, they will be darlings in the press, they are going to raise money more easily and at higher prices, they are going to close amazing business developer partnerships, and they are going to have a strong and cohesive corporate culture. Perhaps more to the point, they are more likely to deliver a positive investment return.

L: How are leadership stories different from the stories we tell around the campfire, or in movies?

RASKIN: The biggest difference is that “happily ever after” hasn’t happened yet. The core leadership story, in other words, is a pitch: Come with me to the Promised Land. That said, in my strategic messaging and positioning engagements with CEOs, as well as my storytelling workshops for teams, I always start by familiarizing leaders with the structure of fairy tales and movies, because that same structure underlies all narratives that connect on an emotional level — be they leadership stories or ghost stories.

RASKIN: It follows from my definition of leadership (above) that any leader who achieves anything does so by telling a great, credible story. One of my favorite examples is Elon Musk and his keynote for Tesla Powerwall — the division of his company that sells batteries. When people ask me for help to tell better strategic stories, I often start by sending this breakdown of Musk’s narrative. His stage presence is sub-par. He’s nervous and fidgety. But by the end of Musk’s talk, his audience cheers. For a battery.

RASKIN: Yes, and in specific ways. Why do we like the characters we encounter in movies and TV shows? It boils down to two things: (1) We see them struggle, and (2) we see them care about others. Take Breaking Bad’s Walter White. He cooks meth and murders people, yet we root for him (for a few seasons anyway). Why? Because we see him struggle against a series of ever-nastier bad guys (Tuco, Gustavo, etc.) and because we know that he cares about his family (and his sidekick, Jesse). By sharing relevant stories about their struggles and how they’ve helped others, leaders offer evidence that we can trust them to lead us to the Promised Land of which they speak.

RASKIN: In my view, storytelling isn’t a fashion accessory that leaders can decide to wear or not. Very literally, leadership is storytelling and leaders are storytellers. Of course, a lot goes into building an effective strategic narrative and aligning everyone around it, but when I’m consulting with leaders who want to hone their leadership story, I always start by asking these five questions:

  1. Whose lives, primarily, are you out to change?
  2. What’s at stake (for them) if you succeed or fail?
  3. What does the Promised Land look like?
  4. What are the obstacles to reaching the Promised Land, and how will you help overcome them?
  5. What evidence can you offer that you can really make the story come true?

About Andy Raskin:
I help CEOs and their leadership teams align around a strategic story to power success in sales, marketing, product, and fundraising and recruiting. Clients include teams backed by
Andreessen Horowitz, NEA, First Round Capital, GV, and other top venture firms. I’ve also led strategic storytelling workshops at Uber, General Assembly, HourlyNerd, Neustar, and Stanford. To learn more or get in touch, visit andyraskin.com.


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