Lenny's Podcast: Product | Career | Growth

How to tell better stories | Matthew Dicks (Storyworthy)

December 15, 2023

AI Summary

5 min read

Matthew Dicks, author of Storyworthy and a Moth storytelling champion, explains that effective stories hinge on everyday moments of personal change, making them memorable tools for connection in business and life. He shares practical techniques drawn from teaching and performance, emphasizing how stories outlast facts or stats because human minds retain imagery tied to emotional shifts.

The five-second heart of every story

Good stories center on a single moment—often just seconds long—where the teller transforms (becoming a new kind of person) or realizes something new (shifting beliefs after accumulated events). The rest of the story provides context to let listeners experience that flip. For example, Dicks recounts hesitating to call anxious student Eileen to the math board, then realizing her growth when she quips about his "cheeky smile"—a moment proving her confidence. Stories start and end in opposition: if the end is "Eileen is confident," the start is her lacking it. This structure ensures meaning, unlike chronological reporting, and works because change universally resonates, even if the specifics (like teaching math) don't.

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What you'll learn

1 **[00:54] Guest Intro & 5-Second Moment Core**
2 **[05:28] 5-Second Examples (Eileen & Star Wars)**
3 **[10:29] Story Structure: Start at End with Opposites**
4 **[16:00] Good Story Checklist & Vacation Caution**
5 **[23:16] Stakes Techniques for Engagement**
6 **[34:00] Business Benefits & Examples (Boris, Marsha)**
7 **[44:41] Personal Inventory, 4 Attention Tools, Humor Strategies**

+ Full timestamped outline available in the app

Show Notes

Matthew Dicks is a best-selling author, columnist, blogger, podcaster, playwright, and teacher. He wrote my all-time favorite book on storytelling, Storyworthy. He is an elementary school teacher by day and by night teaches storytelling and public speaking to individuals, corporations, universities, religious institutions, and school districts around the world. He’s taught storytelling at Yale, MIT, Harvard, and Purdue, along with Amazon, Salesforce, Slack, Lego, and others. In this conversation, Matthew shares insights and techniques for effective storytelling, including:

• The benefits of good storytelling in business

• The five-second moment and why it’s so important

• Why you should start every story at the end

• How to build a vault of stories that can be deployed in business situations

• Tips on how to be funnier

• His life-changing “Homework for Life” practice

• Advice for dealing with nervousness in public speaking

• The power of saying yes

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew

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Where to find Matthew Dicks:

• Website: https://matthewdicks.com/

• X: https://twitter.com/MatthewDicks

• LinkedIn: https://www.linkedin.com/in/matthew-dicks-84a95711/

• YouTube: https://www.youtube.com/channel/UC4K0fcEJkzJLso5h6CN00LQ

• Storyworthy: https://www.storyworthymd.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com