May 26, 2020 / Esther Choy

Sunrise Kilimanjaro - Identify Good Stories

In 2015, Neha Agrawal, a marketing executive at a global medical company, was selected as one of the opening speakers at her company’s multi-day leadership off-site. She needed to set the tone for the day as she spoke with peer senior executives on the topic of leadership. She had about 45 minutes to speak, with no other specific guidelines.

She needed to find a good story fast.

Ultimately, she chose one not from the realm of business but from her personal life. She told her audience of managers the story of climbing Mount Kilimanjaro in 2008 with her parents, sister, husband, and three children—nine people representing three generations and ranging in age from seven to seventy. Not a single one was an outdoor-adventurer type. “We’re more like eaters and strollers,” Agrawal said.

So Agrawal did everything she could to prepare everyone for the trip. For example, she packed everything each person needed each night in a separate Ziploc bag with a clear label, to avoid confusion on the mountain. Of course, they still faced plenty of obstacles, including challenges posed by her seventy-year-old parents’ health, and the fact that her children weren’t allowed past the second climbing station.

For 45 minutes at the leadership off-site, Agrawal regaled her audience with the riveting tale of this extraordinary family journey, with humility and humor. Given the event’s theme, she ended with a list of leadership lessons, like “prepare your team well” and “recognize all the different forms of leadership you will need.”

Many leaders find themselves in Agrawal’s shoes. They know they want to tell stories but are left scratching their heads about how to go about it. Sometimes they even tell themselves, “But I don’t have any stories!”

Everyone has stories. Each and every leader is sitting on top of a goldmine called life. It just takes some digging to find the right story. Keep in mind that it doesn’t have to be work-related. Rather, it can be from your personal life, just like Agrawal’s story. It can even be from your childhood—as long as you make it relevant.

There are two important questions to ask when searching for an effective leadership story.

1. Is It A Story, Or Is It A Leadership Story?

Like any story to be shared with a wide audience, a leadership story has to be a good one. It doesn’t have to be a story about how you saved the world, or even a story about how you saved a project. And it doesn’t have to be a story about an impressive feat like climbing Mount Kilimanjaro (though if you’ve done so, by all means share it!).

“Given the choice between trivial material brilliantly told versus profound material badly told,” says screenwriter and story consultant Robert McKee, “an audience will always choose the trivial told brilliantly.”

A leadership story must be more than just a “good story.” Yes, a riveting story is the baseline, but it also has to meet two other criteria:

  1. Your audience has to know right away why you are telling it.

  2. They have to feel something and do something about it.

Start with these two criteria when you are searching for the right leadership story. Consider the change you want to see and find the story that inspires emotions that will motivate people to act.

To find out if your audience will understand why you’re telling the story, what they’ll feel and what they’ll want to do about it, ask them! Specifically, ask them these three questions:

  1. What info do you recall from my story? (People forget quickly. In seeking feedback, what your audience remembers matters more than what you feel compelled to share.)

  2. How does my story make you feel? (Emotion is the engine behind action. Assessing how your story makes audiences feel will guide you towards the desired action.)

  3. After listening to my story, what questions do you have for me? (Are their questions aligned with what you most want to talk about? What you most want them to do with this information?)

2. Is It A Pitch, Or Is It Truly A Story?

The meaning of “story” can easily get stretched, so that it’s difficult to differentiate between a pitch and a story.

A pitch is a litany, while a story is a journey. A pitch lists your qualifications, credentials and competence without giving your audience a sense of progress, challenges or obstacles. A story, on the other hand, takes the audience from point A to point B, whether that takes one minute or one hour. A story is about change. If challenge is the nerve center of the story, then change is the soul of it.

Confused about whether you’re working on a pitch or a story? Test your audience’s reaction.

  • If it’s a pitch, it will lead to more questions, and then a ‘yes’ or ‘no’ on whether they want to work with you.

  • If it’s a story, the audience will want to tell you their own story, or ask questions about various points in your story, or tell you about similar experiences that have happened to them. This is a really good sign! It means they have fully heard your story and will remember it!

So test your material. Ask close friends or colleagues for feedback on what you will be sharing, and decide from their response whether it is a pitch or a story.

Here’s an example:

I’m a recovering investment banker who now works in corporate philanthropy and social responsibility. My career has always focused on helping the world and the people in it. Our corporate program was recently overhauled, and we would love to work with you to help solve problems that face our community.

Is it a pitch, or a story?

“Recovering” is an excellent, creative touch. But don’t be fooled. This paragraph doesn’t take us on a journey yet, but rather lists reasons the audience should work with this person, so it is still a pitch, not a story.

Here’s another example, from Leadership Storytelling participant Malina:

I am the middle child with an older brother and younger brother. I grew up in a family and time when girls were told they should take care of boys. 

I was only encouraged to go to college so I could find a husband and take care of him, but not only did I complete an engineering degree, I got a PhD in electrical l engineering. Because a sense of fairness and justice were what encouraged me to keep taking the next steps in my career, I am careful to uphold both values when I work with my teams, and I would love to work with teams at your company.

This one has a beginning, middle and end: a journey from childhood to accomplished adulthood in a matter of a few sentences. This one is a genuine story.

If you’ve been able to categorize your own message as a story, the next question of course is… is it a good story?

If it’s a good story, your audience will feel closer to you. They don’t have to like you, but they have to feel like they know you better. For instance, I am currently taking Malcolm Gladwell’s MasterClass, and from the first session, I have felt like he’s my friend. His stories make me feel an affinity for him.

I felt like he was talking with me, not speaking at me, and definitely not presenting to me. He was really “into it.” There’s also the occasional head scratching and nose rubbing that some fellow students criticize as unpolished. But it made me feel like he was at home, comfortable and talking like how my friends would talk with me. This is how your audience should feel too.

Two Prompts To Generate Effective Leadership Stories

Need a prompt to get your leadership story started? These two have consistently launched high-quality leadership stories for my clients.

1. Think of a time when you’ve changed your mind or realized something you used to believe was wrong. Why did you change? What did you learn?

A few years ago I hosted a newly admitted MBA students’ dinner. I asked them about a time they’d changed their minds. One responded by talking about how his views on Obamacare evolved. The dinner was designed as a “reverse-sell” and networking event, so he definitely took a risk by disclosing his views on a controversial subject among strangers! He said he used to be against Obamacare, but as he talked with those who supported or benefited from it, he realized his blindspots. He was not converted, necessarily, but he was able to see the holes in his argument. His story— and especially the risk he took in telling it—gained respect!

How does this story meet the criteria for leadership stories? This story could be used to change others’ minds. In searching for the right story, ask yourself first, “what do I want people to do about my story?” In this case, a leader might work with people who are very single-minded, and perhaps a little too stubborn. If the leader is thinking, “I want them to be more adaptive,” he or she could start with a story like this. It works well because it shows that you can, in the words of Gandhi, “be the change you want to see in the world.” You show that you, yourself, have had blindspots but have learned to embrace new perspectives.

2. Tell the story of a challenge you’ve faced and never expected you’d have to face.

One of my clients shared the following story of a humorous challenge:

I was on a business trip from Geneva to another European city. I was chatting with my colleague, enjoying the food and company. When it was time to get off, I couldn’t find my suitcase. My colleague was surprised by my reaction. Instead of panic, I was laughing. I had travelled for business for 25 years, and this was the first time I didn’t have my suitcase. I considered myself extremely lucky!

This leader didn’t expect the challenge that came his way, but he overcame it with humor and a healthy perspective. And he was able to tell his story right away. When he showed up to his meetings the next day wearing jeans, he was able to share a humorous tale that illustrated his character.

This week, take a moment to sift through your life—your goldmine—and find stories with a clear central purpose that motivates your audience to action.


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We’d love to help you identify good stories to tell in your unique business context. We’ll help you choose and shape the right stories for the right opportunity. Schedule a complimentary working session with us. For more examples of the right stories to tell at the right time, sign up for our monthly guide. My book, Let the Story Do the Work (published by HarperCollins Leadership), is now available and serves as your business storytelling toolkit.

#LetTheStoryDoTheWork #RobertMcKee #MalcolmGladwell #Pitch #StoryPrompts #BusinessStorytellingPrompts

Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
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