How to tell better stories | Matthew Dicks (Storyworthy)

How to tell better stories | Matthew Dicks (Storyworthy)

Lenny's PodcastDec 15, 20231h 42m

Matthew Dicks (guest), Lenny Rachitsky (host)

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

In this episode of Lenny's Podcast, featuring Matthew Dicks and Lenny Rachitsky, How to tell better stories | Matthew Dicks (Storyworthy) explores mastering Business Storytelling: Five-Second Moments, Stakes, and Yes 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.

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

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.

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.

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.

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.

Key Takeaways

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.

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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.’

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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.

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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.

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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.

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Signal the start of a story with location and action, naturally.

Begin every story with a concrete place and something happening (“I’m in the classroom, and I’m debating whether to call Eileen to the board”)—this activates imagination, feels conversational, and quietly commands the room’s attention.

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Say yes to uncomfortable opportunities; you can always say no later.

Dicks argues that refusing unknown experiences is usually fear masquerading as discernment; saying yes opens unexpected doors, generates growth and story material, and any yes can be reversed once you’ve truly seen what’s behind the door.

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Notable 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)

Questions Answered in This Episode

How can I identify the five-second moment in my own experiences or product stories, especially when the change feels subtle?

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.

Get the full analysis with uListen AI

In my current role, where are the non-obvious places I could replace dry explanations with short stories without seeming self-indulgent?

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.

Get the full analysis with uListen AI

Which of Dicks’s stakes tools (elephant, backpack, breadcrumbs, crystal ball, hourglass) do I most underuse, and how might applying them change my next presentation?

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.

Get the full analysis with uListen AI

What would my own Homework for Life practice look like in concrete terms, and what obstacles will make it hard to sustain daily?

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.

Get the full analysis with uListen AI

What scary ‘door’ have I been saying no to that might actually unlock growth and better stories if I chose to say yes?

Get the full analysis with uListen AI

Transcript Preview

Matthew Dicks

Everyone loves the word storytelling in business. It's a huge buzzword. They love to think of themselves as storytellers. But when they come to me, they don't really want to be storytellers, because to be a storyteller means you have to separate yourself from the herd. And in their mind, that risks them getting picked off, right? Getting picked off by some predator. But the- the alternative is, you're in the herd, which means you're forgettable. I mean, how many times have you gone to a conference, listened to someone speak, and by the time you're pulling into the driveway, you really can't remember anything that they said? Because that's what happens if we don't speak in story. Our minds are not designed to remember a pie chart or facts or- or statistics or, you know, platitudes, or ideas that are not attached to imagery. So, the risk you take if you're not telling stories is that you will be forgotten. 100%, you will be forgotten.

Lenny Rachitsky

(Instrumental music) Today, my guest is Matthew Dicks. Matthew is the author of my all-time favorite book on storytelling, Storyworthy, which a previous guest of the podcast recommended to me and I couldn't put it down, so I reached out to Matthew and got him on the podcast. Matthew is a 59-time Moth StorySLAM winner and nine-time Grand SLAM champ. He's also the author of nine other books, including fictions, rock operas, even a comic book. In his day job, he is an elementary school teacher, and on the side, teaches both individuals and teams at companies like Slack, Amazon, Lego, and Salesforce the skill of storytelling and public speaking through his company, Speak Up. In our conversation, we get very tactical about how to tell better stories, both in life and in work, how to feel more comfortable speaking on stage, how to come up with story ideas that you can deploy when the need arises, why every good story is centered around one five-second moment of transformation, and so much more. Matt is an incredible human being, and I am excited to spread his message more widely. If you're interested in this topic, definitely pick up his book, Storyworthy. It'll change your life. With that, I bring you Matthew Dicks after a short word from our sponsors. Today's episode is brought to you by OneSchema, the embeddable CSV importer for SaaS. Customers always seem to want to give you their data in the messiest possible CSV file, and building a spreadsheet importer becomes a never-ending sink for your engineering and support resources. You keep adding features to your spreadsheet importer, but customers keep running into issues. Six months later, you're fixing yet another date conversion edge case bug. Most tools aren't built for handling messy data, but OneSchema is. Companies like Scale AI and Pave are using OneSchema to make it fast and easy to launch delightful spreadsheet import experiences, from embeddable CSV import to importing CSVs from an SFTP folder on a recurring basis. Spreadsheet import is such an awful experience in so many products. Customers get frustrated by useless messages like error on line 53 and never end up getting started with your product. OneSchema intelligently corrects messy data so that your customers don't have to spend hours in Excel just to get started with your product. For listeners of this podcast, OneSchema's offering a $1,000 discount. Learn more at oneschema.co/lenny. This episode is brought to you by Maui Nui Venison, a mission-based food company bringing the healthiest red meat on the planet directly to your door. I actually joined Maui Nui Venison earlier this year after hearing their ad on The Tim Ferriss Podcast, and I'm excited to be spreading the message further. Not only does this company provide the most nutrient-dense and protein-dense red meat available, their operation produces the only stress-free 100% wild-harvested red meat on the market, that is the only one of its kind in the world, actively managing Maui's invasive axis deer populations, helping to restore balance to vulnerable ecosystems, food systems, and communities in Hawaii. Also, it is seriously delicious, not at all gamey, and easy to cook. My wife and I made stew and steaks and all kinds of grilled goodies with the meat. We also feel great about it as a protein from an ethical standpoint. I highly recommend trying their all-natural venison jerky sticks for an optimal protein snack, as well as a wide variety of fresh cuts, all available in their online butcher shop. There are limited memberships available, but you can sign up and get 20% off your first order at mauinuivenison.com/lenny. That's mauinuivenison.com/lenny. Matt, thank you so much for being here. Welcome to the podcast.

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