November 5, 2023 / Esther Choy

In this month’s Forbes article, I shared about how to turn a personal story into a leadership story in three steps. Like learning any new leadership skill, business storytelling takes practice. We need to become familiar with both how and when to tell stories.

In our Certified Storytelling Facilitator Training we like to share examples because hearing stories in action can help us recognize when we have the opportunity to share stories, and remind us of our story-worthy moments that can be used in leadership storytelling moments.

Here’s a story from our client Matt, who workshopped it during a Leadership Story Lab training session designed to help business leaders practice their leadership skills. The context for this was that Matt had an employee who wasn’t taking ownership of his role or tasks. This employee was opting for the easiest way to complete a job or not completing the job because of some unforeseen obstacle. Both options always led to poor results and frustration for all of his colleagues.

At the end of the story you will find guiding questions help you practice this must-have leadership skill, using your own story-worthy moments to craft your leadership story.

Here’s the story:

On my dad’s birthday when I was four years old my mom wanted to bake him his favorite cake, pineapple upside down cake. But she was missing one of the key ingredients: maraschino cherries.  Since my one-year-old sister and I were home sick with fevers, my mom’s only option to get that last ingredient was my six-year-old brother. We only lived two blocks from a grocery store, and this was a different time. So my mom wrote out “MARASCHINO CHERRIES” on a piece of paper, handed it to my brother and sent him on his way.

My mom stood out on the sidewalk in front of our house and watched him walk the two blocks and then turn to go toward the store. After a few minutes she came back in to check on me and my sister. After a few more minutes she went outside to check on my brother. She looked down the sidewalk, but saw no sign of him. After another few minutes she looked down the sidewalk again and still no sign of him.  At this point, she realized it had been more than 30 minutes. She started to get nervous.

Just as she was about to go in and call the store she saw my brother walking down the street carrying a brown paper bag. When he got to our house my mom hugged him.  When she opened the bag, there was a can of pineapples.  So she turned and asked my brother why he didn’t buy the maraschino cherries.  He looked up at her with sad eyes, pointed in the air and said, “The cherries were way up there, and the pineapples were right here.”

I have often thought of that story and what my brother must have been thinking about in the store.  He must have walked up and down that aisle a few times trying to think of a way to get those cherries. He probably thought about asking someone for help but remembered that he wasn’t supposed to talk to strangers. So after much internal debate he remembered my mom was making pineapple cake so he should buy some pineapples.

What is the point of this story you might ask? Well at times in your career you will be faced with similar situations.  You will:

  • Be given a task
  • Be challenged to complete the task
  • Sometimes you have people around to ask for help, sometimes not
  • Need to think through options and make decisions
  • Either come back with nothing, leaving the task incomplete and giving the impression that you don’t care or you aren’t smart enough
  • Or bring back an alternative that you know will add some value, demonstrate care, and show that you are smart enough to recognize needs

So wherever you are in your career, remember that bringing back pineapples is always better than not bringing back anything at all.

Matt’s story demonstrates his leadership skill in crafting sharing his expectations for his employees by using a childhood incident as an analogy. While he doesn’t prescribe his expectations point by point, he shares a leadership principle that matters to him, in a way that is hard to forget.

What happened after Matt told this story to his team? He shared with us that the person working for him devised several new strategies that successfully improved sales and ROI on our company’s promotional investments.

So, now it’s your turn. How will you practice this leadership skill and craft own story that motivates your employees to be creative self-starters?  Use these three guiding steps.

  1. Consider what outcomes you are looking for. You might want to inspire your team to have ownership over a project’s progression or to experiment with new ideas. Knowing exactly what kind of outcomes you are looking for will help you find the best personal story.
  2. Mine stories from your personal experiences; situations that seem far from your work and team environment can be best to capture your team’s attention and imagination.
  3. Be 100% clear on the takeaways of your story and how they relate to the present situation. Elaborate on your expectations and how you want your team to perform.

Want a place to practice your newly crafted leadership story? Sign up for Story Lab and you will receive constructive feedback in a safe environment with other people learning how to tell their own leadership stories.


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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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"This is an amazing and insightful post! I hadn’t thought of that so you broadened my perspective. I always appreciate your insight!" - Dan B.

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