The Storytelling Mistake to Rule them All: Generalizing

June 27, 2022

In our work as storytelling coaches, one of the most common challenges our clients face is bringing their stories down to specifics. Recently, Stephanie had a client, let’s call her Jane,  come to her for support in preparing for an interview. Jane knew that she was going to be asked about her origin story. In her case, the question was going to be something along the lines of, “What inspired you to get into the field of Mathematics?” Here’s a rough approximation of the story she started with:


When I was a kid, my dad would always bring a math problem to the dinner table. My sister and I would work through the problem while we ate—often with the gusto of competition that only siblings know. The challenges were varied, but the solutions were always elegant and simple, and would showcase a kind of grace in mathematics. I remember being inspired by these problems every night, and of course it was especially fun when I would solve the problem before my sisters. I looked forward to these evening dinnertime challenges, and through them, developed a love of Mathematics.

This is a very common starting point for storytellers. They have a generalized memory—a habit, routine, or repeated behavior that they recall— and they consider that enough to be a story. The trouble with this generalized approach is that it remains high-level. It doesn’t give space for the audience to see and feel the mental, physical, or emotional drama.


After some coaching, here’s a refined version of the story Jane developed:


It’s Tuesday evening at 6pm. At 8 years old, I sat at the dinner table holding my fork.  My heart beat raced in eager anticipation of tonight’s math problem.


“Daddy! What’s today’s problem?” My older sister eyes me as she chews a meatball. She isn’t going to let me beat her to the solution again.


My father began. “A poor man was very sad. He smoked his last cigarette and didn’t know what to do. He couldn’t afford more, but his body was suffering from withdrawal. He went to a magician and asked for help. The magician told him that if the poor man brought him 7 cigarette butts, he would use his magic to transform them into a new cigarette. The poor man scoured the park and brought back 49 cigarette butts. How many cigarettes did he smoke?


“Seven!”I know my division tables. Ha! I win! I look at my sister.


“Wrong. Think again.” My dad’s eyes twinkle.


“Huh?” My sister and I look at each other again. “How?”


For the rest of that dinner, between bites of spaghetti, my sister and I pow-wow. We allied against our father. We had to figure it out. How was it not 7? It had to be 7! What were we missing? We scratch our heads. 


An hour later my father says, “Ok, I’ll give you the answer. It’s 8. But you have to tell me why.”


My 8-year-old brain struggles some more. Then, suddenly, a lightbulb! “I know! I know!”


Almost every night, my parents brought math problems to the dinner table. Every answer always felt so clever and graceful, elegant and clean. It was magical. When it came time for me to choose a career path, Math was the obvious choice. 


In this case, the choice to focus on a specific math problem on a specific night allows this general memory to become a full-fledged and information-packed story. 


  • The second story is more visual. The dinner table, the characters, their movements and thoughts can all be imagined as if they’re in a movie scene. This makes the story more interesting, easier to follow and more experiential for the listener.
  • The second story does a better job of engaging the listener’s curiosity. The audience can try to solve the math problem themselves because they hear it and Jane doesn’t rush to the answer in the telling of it.
  • The second story feels more real because we understand the specific emotional connection Jane has to math via experience and the emotions it creates for her.


It is specificity that allows all of the above to be possible.


A common objection that we hear is that the second story is longer than the first. And that’s true… It contains almost three times the number of words. When brevity is the most important thing, stories may not be the best tool of choice. But when coming across as a compelling and memorable communicator, consider stories—especially ones that lean on specificity—to carry your message.



What other strengths do you notice in the second story?

Share this article

Recent Posts

December 15, 2025
Stephanie and Kara both learned early in our professional lives that follow-through matters. As students at Michigan Ross School of Business, it was drilled into us: after an interview, send a thoughtful thank-you note that references the conversation. It was presented as a way to stand out and be polite… a nice finishing touch to remember you by.  But although a thank you is polite, it doesn’t build momentum.
December 1, 2025
Early in our Wolf & Heron days, Stephanie facilitated our Influential Storytelling workshop for a major new client. It was a high-stakes moment: 100+ people in the room, a huge win for us, and her first time delivering the workshop solo. She opened with a story she had polished, rehearsed, and delivered successfully many times before.
November 17, 2025
Carissa came to Stephanie frustrated. She had a 15-minute slot with her executive leadership team, and she wanted to understand why her user-research findings weren’t influencing leadership action. She had spent months gathering insights, synthesizing trends, and surfacing recommendations, yet every time she presented them, leaders nodded politely and moved on. There was no change or follow through. 
People seated around a table, one speaking, others listening, against a yellow background.
November 4, 2025
We’ve all sat through meetings that looked good on paper but left us frustrated. Stephanie was recently invited to a meeting that included an agenda right in the calendar invite!
Show More