Lenny's PodcastHow to tell better stories | Matthew Dicks (Storyworthy)
CHAPTERS
- 0:00 – 0:51
Why business storytelling matters: standing out vs. being forgotten
Matthew opens with the core business case for storytelling: most professional communication is forgettable because it’s detached from vivid imagery. He frames a tradeoff between blending into the “herd” (safe but invisible) and taking the risk of standing out through story.
- •Storytelling is a business buzzword, but many people fear the vulnerability required to do it well
- •Audiences don’t retain charts, stats, and platitudes as well as images and narrative
- •Being “in the herd” feels safe, but makes you forgettable
- •Conferences illustrate the problem: polished talks without story vanish from memory
- 0:51 – 5:12
Who Matthew Dicks is and what this conversation will cover
Lenny introduces Matthew’s background as a champion Moth storyteller, prolific author, and elementary school teacher. He sets expectations that the episode will be highly tactical, spanning storytelling craft, workplace use cases, and public-speaking confidence.
- •Matthew’s credentials: Moth wins, multiple books, and corporate storytelling training
- •The episode’s promise: practical techniques you can use immediately
- •Storytelling as a life skill and a business skill
- •Teaser themes: five-second moment, transformation, and story idea generation
- 5:12 – 7:06
The “five-second moment”: every great story centers on a single flip
Matthew explains his defining concept: every effective story revolves around one brief moment of transformation or realization. Most of the story’s job is to create context so the audience experiences that internal ‘flip’ alongside the storyteller.
- •Stories are built around a single moment of realization or transformation
- •The shift often feels gradual but occurs in one identifiable instant
- •98% of the story is context that clarifies the moment of change
- •This applies across media: spoken stories, novels, TV, and film
- 7:06 – 10:29
Examples of the five-second moment: Eileen’s quip and Luke’s faith
Matthew demonstrates the idea with a real classroom moment where a student’s teasing comment signals newfound confidence and trust. He then scales the concept to pop culture, explaining how Star Wars hinges on Luke choosing faith (The Force) over technology.
- •Eileen’s “cheeky smile” line as the exact moment Matthew understands she’s ready
- •How a small moment can be expanded into a longer, richer narrative
- •Star Wars reframed as a story about adopting belief (religion)
- •Why audiences connect to ‘before vs. after’ mental shifts
- 10:29 – 14:28
Start at the end: knowing the ending reveals the beginning and structure
Lenny and Matthew discuss why strong storytelling begins by identifying the ending—what changed. Once you know the ending, you can craft a beginning that stands in opposition, making the arc inevitable even if the journey stays entertaining.
- •For true stories, the storyteller must know the end because they lived it
- •A story’s beginning and end should operate in opposition
- •You can often predict a movie’s ending from the first 10–15 minutes
- •Knowing the destination doesn’t ruin the experience; execution matters
- 14:28 – 18:19
Why transformation is non-negotiable (and the ‘dinner test’ for authenticity)
Matthew argues that change is what makes a story universally relatable beyond shared job context. He introduces the ‘dinner test’—good stage or business stories should still sound like a slightly elevated version of how you’d speak at dinner, avoiding theatrical gimmicks.
- •“Reporting your day” rarely connects; change creates universal appeal
- •Dinner test: avoid unnatural devices (unattributed dialogue, sound effects)
- •Aim for natural speech with less verbal filler
- •Start as close to the end as possible (Vonnegut’s guidance)
- 18:19 – 20:24
You can’t tell someone else’s story (and how to ethically ‘center yourself’)
Matthew explains why stories must be personal: telling someone else’s story blocks vulnerability and feels like fiction to listeners. He offers a workaround—tell your story and show how another person’s experience shaped you, making the connection authentic.
- •Audience connection depends on vulnerability, which requires personal ownership
- •Third-person stories often lack emotional credibility on stage
- •Technique: connect historical/other-person narratives to your own transformation
- •Example: descendants of Holocaust survivors telling impact-on-me stories
- 20:24 – 23:14
Vacation stories and the art of ruthless focus: cut the travelogue
Matthew humorously dismantles the typical vacation recap, arguing that unless a true change happened, no one cares. Even if it did, you should tell only the relevant scene—often the moment at dinner, not the beach, flight, or itinerary.
- •Most vacation stories are chronological humble-brags without transformation
- •If change occurred, start at the moment it happened and ignore the rest
- •Shortest version of the story is usually the best version
- •Location only matters if it meaningfully affects the change
- 23:14 – 34:01
Stakes and momentum: how to keep people wondering what happens next
Matthew defines stakes as what the audience should worry about, hope for, or question—without it, they stop listening. He outlines multiple practical tools to add and escalate stakes throughout a story, then separates stakes from surprise as its own powerful ingredient.
- •Stakes = audience concern and curiosity about the next sentence
- •Business speakers often overestimate baseline audience interest
- •Tools: the ‘elephant’ up front, backpacks (state the plan), breadcrumbs, hourglasses (slow time), crystal balls (predict a future)
- •Surprise should feel both inevitable and unexpected; it’s often mishandled
- 34:01 – 37:43
Storytelling at work: being memorable, not ‘round, white, and flavorless’
Matthew transitions into business applications, arguing story is the antidote to mediocre, forgettable corporate communication. He illustrates memorability with the lunchbox conference story, contrasting it with polished but instantly-forgettable executive talk.
- •Not telling stories keeps you ‘like everyone else’—and forgettable
- •The lunchbox story demonstrates vulnerability, imagery, and meaning
- •Facts and fluency aren’t enough; narrative creates recall
- •Storytelling requires standing apart from the herd to be remembered
- 37:43 – 44:41
Deployable business stories: Boris’s ‘failure’ story and Marsha’s Slack narrative
Matthew shares concrete workplace examples: a factory owner uses a Little League strikeout story to reshape sales-team resilience, and a Slack comms leader learns that a brief personal anecdote can dramatically increase connection. He introduces ‘bricks vs. Band-Aids’ as building a reusable story vault versus solving one-off messaging needs.
- •Boris uses a parenting story to teach faster recovery from sales failure
- •Story beats scolding: it reveals the leader’s humanity and model behavior
- •Marsha’s Tuesday-night inspiration shows how small personal context boosts engagement
- •Bricks vs. Band-Aids: build a library of stories you can reuse strategically
- 44:41 – 53:13
Relatability by design: personal interest inventory + four attention levers
Matthew explains how to be strategically human at work using a ‘personal interest inventory’—details about yourself that create connection. He then outlines four universal ways to keep people listening in business: stakes, surprise, suspense, and humor, emphasizing that humor is feared because it demands risk.
- •Personal interest inventory: share identity details with ‘addressable market’ and ‘intensity’ in mind
- •Tactical trick: answer common questions (‘How are you?’) with a revealing, human detail
- •Four attention levers: stakes, surprise, suspense, humor
- •Humor differentiates, but most corporate speakers retreat to the herd
- 53:13 – 1:06:37
Humor you can actually use at work: nostalgia and ‘one of these things’
Matthew offers practical, non-cringey humor strategies suited for business storytelling. He highlights nostalgia as a reliable laugh generator and the Sesame Street pattern (expected, expected, unexpected) to create punchlines without resorting to stand-up-style jokes.
- •Nostalgia is inherently funny and useful for product evolution narratives
- •Example: job hunting ‘in 1983’ as a humorous, expertise-signaling opener
- •‘One of these things is not like the other’: two expected beats + an unexpected third
- •In-story humor is safer: if a line doesn’t land, you’re still telling a story
- 1:06:37 – 1:15:30
Homework for Life: building a story bank and slowing time down
Matthew introduces his most important practice: write down one story-worthy moment every day in a simple spreadsheet. Over time, it trains a ‘story lens,’ recovers lost memories, reveals patterns, and makes life feel longer because more days are accounted for.
- •Daily habit: date + short moment description (not full story drafts)
- •Goal starts small (e.g., 12 stories/year) but expands into abundance
- •Therapeutic benefits: preserve parenting moments, notice personal patterns, regain forgotten memories
- •The prompt: if your family were kidnapped and you had to tell a story from today—what would it be?
- 1:15:30 – 1:19:26
Getting started (today): practical setup and habit mechanics
Lenny asks for concrete steps to begin Homework for Life immediately. Matthew recommends committing to daily entries, capturing moments throughout the day to prevent loss, and using spreadsheets for durability and later organization.
- •Start with Excel/Google Sheets: two columns (date + moment)
- •Capture during the day (lunch, after work, evening) to avoid forgetting
- •Label older resurfaced moments as ‘MEMORY’ to avoid timeline confusion
- •Consistency matters: each missed day is permanently lost detail
- 1:19:26 – 1:25:25
Public speaking nerves and preparation: reduce fear without memorizing
Matthew reframes stage fright: most nervousness happens before you start, and drops once you’re speaking. He shares preparation methods—especially recording and passive listening—to internalize flow, and emphasizes mastering transitions rather than memorizing scripts.
- •Most nerves are pre-talk; starting to speak dissolves anxiety for many people
- •Everyone is nervous (Matthew is the outlier), which normalizes the experience
- •Record and listen repeatedly to internalize structure and phrasing
- •Practice scene-to-scene transitions; avoid full memorization
- 1:25:25 – 1:31:08
The power of saying yes: stepping through doors (and why it’s not about stories)
Matthew argues that saying yes isn’t primarily a tactic to generate better anecdotes—it’s an antidote to fear and premature certainty about what’s behind a door. He explains that yes can become no after exploration, but refusing to step through doors limits the surprising causal chains that create growth.
- •Saying no often comes from fear and overconfidence about outcomes
- •A ‘yes’ can be tested and later reversed; a ‘no’ forecloses possibilities
- •Life gets smaller with age; doors stop appearing, so take them now
- •Example: Matthew pushed himself into stand-up because it terrified him
- 1:31:08 – 1:42:56
Lightning round + one tactical storytelling rule: location then action
In the rapid-fire close, Matthew shares favorite books and recent shows, then ends with a crisp storytelling tactic: begin every story with location and action. This instantly activates imagination, signals ‘the movie is on,’ and can help marginalized speakers claim space and attention.
- •Recommendations: Heart of the Sea, Tale of Despereaux, Sedaris/Klein, plus recent favorites like The Last of Us
- •Favorite question: ‘How did you get into the job you currently have?’
- •Tactic: start with location to trigger imagery and instant context
- •Tactic: start with action to create momentum and silence the room
