The Storytelling Mistake to Rule them All: Generalizing

June 27, 2022
Girl pondering math problems on a chalkboard.

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?

Summary of Takeaways

The single most common error that strips a story of its power is generalizing. When speakers use broad, "we" focused language or summarize events rather than detailing them, they prevent the audience from visualizing the moment. To move from a generic update to an influential story, you must fight the urge to generalize:

  • The Problem with "We": Using "we" (e.g., "We felt that the project was a success") creates a distance between the speaker and the audience. It feels corporate and safe. Influential storytelling requires the "I"—the personal vulnerability and specific perspective that only you can provide.
  • Specifics Build Trust: Generalizations are easy to ignore or doubt. Specific details (e.g., "The silence in the room was so thick I could hear the hum of the projector") are "proof points" for your brain. They signal to the listener that this event actually happened, which makes your resulting insight much more credible.
  • Summarizing vs. Storytelling: Summarizing is for reports; storytelling is for influence. Instead of summarizing a three-month process in one sentence, pick one specific moment (a scene) that represents the entire journey. One vivid, specific moment is more memorable than a thousand generalities.
  • Emotional Specificity: Don't just say you were "excited" or "stressed"—those are general labels. Describe the physical sensation or the specific thought you had. Instead of "I was nervous," try "I felt a cold knot in my stomach as I reached for the door handle."
  • The "Mental Movie" Test: If your audience can’t "see" what you’re talking about in their mind’s eye, you are generalizing. Use concrete nouns and active verbs to help them render a "mental movie." The more specific the image, the more likely it is to stick.

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