Why Leadership Equals Storytelling

Andy Raskin by

Editor’s Note: The following post is based on an interview between Andy Raskin and Leadfully, a service of SYPartners. You can read the original interview here.

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.”

The Core Leadership Story Is a Pitch

For leaders and their followers, “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, I always start by familiarizing leaders with the structure of fairy tales and movies. That’s because the same structure underlies all narratives that connect on an emotional level — be they leadership stories or campfire stories.

Unclear Story, Unclear Strategy

It follows from my definition of leadership (above) that any leader who achieves anything does so by telling a great, credible story. As Andreessen Horowitz’s Ben Horowitz explains, startup leaders tend to think of story and strategy as two different things, but they’re not:

“Companies that don’t have a clearly articulated story don’t have a clear and well thought-out strategy. The company story is the company strategy.

One of my favorite examples of a clear, powerful strategic story is Elon Musk’s keynote for Tesla Powerwall — the division of his company that sells batteries. When people ask me for help with their strategic story, 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.

Tales of Struggle and Caring Make You Likeable

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, of course, 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.

How to Improve Your Leadership Story

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. When I’m consulting with leaders who want to hone their core strategic 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?

How are you crafting your leadership story? Let us know in the comments.

About Andy Raskin
Andy helps leaders align around a strategic story — to power sales, marketing, fundraising, product, and recruiting. His clients include teams backed by Andreessen Horowitz, First Round Capital, GV, and other top venture firms. He’s also led strategic story training at Uber, Yelp, General Assembly, HourlyNerd, Neustar, and Stanford. To learn more or get in touch, visit andyraskin.com.

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Strategic Messaging & Positioning Leader