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How to tell better stories | Matthew Dicks (Storyworthy)

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 — Brought to you by OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door: https://mauinuivenison.com/discount/LENNY?utm_medium=podcast&utm_source=show_notes&utm_campaign=lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew 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/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Matthew’s background (04:27) The five-second moment (10:29) Knowing the ending (14:28) The importance of including a transformation (15:59) The dinner test (18:19) You can’t tell someone else’s story (20:24) Vacation stories (23:14) Adding stakes to the story (25:12) The power of surprise (29:20) The benefits of storytelling in business (32:20) An example of adding stakes (34:02) Storytelling in the workplace (44:29) Using personal inventory to make stories relatable (48:46) Four ways to keep people listening (50:52) Using humor in business storytelling (53:09) Advice for adding humor (58:43) An example of how storytelling helped a biotech company sell product (1:02:06) Advice for people who don’t want to become storytellers (1:06:35) The power of “Homework for Life” (01:15:26) Practical tips for starting Homework for Life (01:19:28) Dealing with nervousness in public speaking (01:24:42) Preparing for a talk or presentation (01:25:24) The power of saying yes (01:30:55) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Matthew DicksguestLenny Rachitskyhost
Dec 14, 20231h 42mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Mastering Business Storytelling: Five-Second Moments, Stakes, and Yes

  1. Matthew Dicks, champion storyteller and author of *Storyworthy*, explains how to craft powerful stories for both life and business, centering everything on a single "five-second moment" of transformation or realization.
  2. He breaks down practical frameworks: finding that core moment, structuring beginnings and endings, adding stakes, surprise, suspense, and humor, and ensuring stories pass his “dinner test” of sounding natural and human.
  3. Dicks shows how storytelling makes you memorable in otherwise forgettable corporate contexts, and offers concrete tools like Homework for Life to systematically surface story ideas from everyday life.
  4. He also covers managing stage fright, weaving personal details into business communication, and the life philosophy of saying yes to scary opportunities to create richer experiences and more compelling stories.

IDEAS WORTH REMEMBERING

5 ideas

Anchor every story in a single five-second moment of change.

Identify the precise instant where you (or a character) realize something new or transform, then build 90–98% of the story as context leading to that flip; this gives your story focus and emotional punch.

Start with the end, then design the beginning as its opposite.

For true stories, you already know the ending (your five-second moment); define what’s emotionally or conceptually opposite at the beginning so the audience clearly experiences the arc from ‘before’ to ‘after.’

Use stakes, surprise, suspense, and humor to keep attention.

Dicks outlines tools like elephants (big stakes upfront), backpacks (sharing your plan), breadcrumbs, crystal balls (predicting futures), and hourglasses (slowing time at peak tension), plus nostalgia and odd-one-out patterns for humor.

Make business communication personal and story-driven to be memorable.

Instead of abstract decks and platitudes, tell short, human stories about yourself (or colleagues), then explicitly connect the theme to your product, team, or strategy; this builds connection and retention far better than facts alone.

Adopt Homework for Life to systematically uncover story material.

Every day, capture one meaningful moment in a simple spreadsheet (date + a single line of description); over time this trains your eye to notice stories, slows down your sense of time, and gives you a deep library of usable anecdotes.

WORDS WORTH SAVING

5 quotes

The risk you take if you're not telling stories is that you will be forgotten. 100%, you will be forgotten.

— Matthew Dicks

Essentially every story is about a singular moment… a moment of either transformation or realization.

— Matthew Dicks

Most communication in business is round, white, and flavorless.

— Matthew Dicks

Storytellers are people who think before they speak. They make strategic, tactical decisions before they open their mouths.

— Matthew Dicks

A positive mental attitude will be your key to success.

— Fourth-grade teacher (quoted by Matthew Dicks)

The concept of the five-second moment (transformation/realization) at the heart of every good storyStructuring stories: starting from the end, opposites, and the “dinner test”Creating stakes, surprise, suspense, and humor to hold attentionApplying storytelling in business: pitches, internal talks, product narratives, and salesHomework for Life: a daily practice for finding and preserving story materialMaking stories personal and relatable (personal interest inventory, vulnerability)Overcoming fear of public speaking and the philosophy of saying yes

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