Listen to the original at Lenny’s Podcast ↗lennysnewsletter.com
By Lenny Rachitsky · with Matthew Dicks · lennysnewsletter.com · @lennysan on X · YouTube · LinkedIn
Matthew Dicks, a 59-time Moth Story Slam winner, elementary school teacher, and author of the book Storyworthy, discusses how to tell better stories. The conversation covers the core structure of stories built around a single moment of change, practical tools like stakes and humor, and how storytelling can make business communication memorable.
01Key learnings
- Build every story around one five-second moment of transformation or realization, and make the rest of the story context that leads to it.
- Start stories as close to the end as possible, because the ending moment determines what you need to say and where to begin.
- Apply the dinner test: tell stories the way you would at a dinner table, only slightly elevated, without performance tricks like unattributed dialogue.
- Tell stories about yourself rather than others, since vulnerability is what makes an audience connect; avoid vacation stories unless a real moment of change happened.
- Keep audiences hooked by continually adding stakes, using tools like crystal balls, hourglasses, backpacks, breadcrumbs, and an opening elephant, rather than front-loading them all.
- Assume no one wants to hear what you have to say, and use stakes, surprise, suspense, and humor to keep listeners engaged.
- Practice Homework for Life by logging one or more daily moments in a simple spreadsheet, building a bank of stories you can deploy later in business.
- Use theme and message adjacency: find a personal story sharing the same meaning as your product or idea rather than matching content directly, and insert personal details that create connection.
“Our minds are not designed to remember a pie chart or facts or statistics or platitudes or ideas that are not attached to imagery.”Matthew Dicks · Lenny’s Podcast · 00:00:00
“The shortest version of every story is the best version of every story.”Matthew Dicks · Lenny’s Podcast · 00:22:24
“Storytelling is not about facility with the language or your vocabulary. It's all about decision-making.”Matthew Dicks · Lenny’s Podcast · 01:16:59
02Frameworks mentioned
Five-second momentDinner testStakes tools (elephant, backpack, breadcrumbs, hourglass, crystal ball)Homework for LifeSpeaking with adjacency
Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.