Why Leadership Storytelling - Medium PDF

This document summarizes an interview with Andy Raskin about the importance of leadership storytelling. Raskin explains that leadership inherently involves telling a story to inspire others. Effective leadership stories are like movie pitches that invite others on a journey to a promised future. Leaders must be vulnerable and share their struggles and care for others to build trust. Raskin advises leaders to focus on answering questions about their vision, challenges, and ability to deliver when integrating storytelling into their leadership.

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Why Leadership Storytelling - Medium PDF

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Claudio Chagas

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Andy Raskin
Helping leaders tell strategic stories. Ex @skype @mashery @timeinc http://andyraskin.com
4 days ago · 3 min read

Why Leadership = Storytelling

“The great storytellers have an unfair competitive

advantage.”— Bill Gurley

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.

LEADFULLY: Why is storytelling a must-have

leadership skill?
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 di erent from the stories

we tell around the camp re, 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.

L: Can you share an example of a leader achieving

concrete results with storytelling?

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.
L: Do leaders need to be vulnerable —to share
something about themselves —in order to be e ective

at storytelling?

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.

’
L: What s your #1 piece of advice for integrating

’
storytelling into one s leadership style?

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.