How to tell better stories: Matthew Dicks on the craft of storytelling

Executive overview

Most business communication is forgettable because it reports information rather than tells stories. The human brain is not designed to retain facts, statistics, or pie charts — it retains story. Matthew Dicks, 59-time Moth Story Slam winner, teaches a practical framework built on one core insight: every good story is anchored to a single five-second moment of transformation or realization, and everything else exists to bring that moment into focus.

The risk of not telling stories is not mediocrity — it's guaranteed forgettability.

The five-second moment

• Every story turns on one moment: a transformation ("I used to be X, now I'm Y") or a realization ("I used to think X, now I think Y").
• The entire story is context built to make that moment land — 98% setup, 2% flip.
• Identify your five-second moment first; it tells you how the story ends, which tells you where it must begin.
• Begin at the opposite of where you end — the story moves from one state to its contrast.
• Most realizations happen in ordinary moments, not dramatic ones: walking across a parking lot, sitting at a desk.
• Start as close to the end as possible. Front-loading backstory is the single most common mistake Matthew corrects.

What makes a story worth telling

• Change: something must shift — in belief, understanding, or circumstance. Without change, you're reporting, not storytelling.
• The dinner test: tell it the way you'd tell it at a meal — natural, direct, no performance-art openings, no unattributed dialogue, no sound-effect openers borrowed from bad elementary-school writing advice.
• It must be your story — only you can provide the vulnerability an audience connects to; stories about other people feel like fiction.
• The exception: stories about others become yours when you center them on how that experience changed you.
• Vacation stories almost never qualify — unless a five-second moment happened, the location is irrelevant and the audience is just subsidizing your nostalgia.
• The shortest version of every story is the best version.

Building stakes

Stakes are what the audience worries about on your behalf. Without them, people stop listening. Five tools:

1. Elephant — plant something at the very opening that signals what kind of story we're in; the audience needs to wonder what happens next within seconds.
2. Backpack — share your plan before you execute it, so the audience carries your hopes and feels it when things go wrong (Ocean's Eleven works this way).
3. Breadcrumbs — drop hints of what's coming without revealing it; Chekhov's gun is a breadcrumb.
4. Hourglass — when the moment of truth arrives, slow down, load the scene with detail, and make the audience wait as long as possible.
5. Crystal ball — predict a plausible (even false) future; planting a bad outcome in the audience's mind creates worry whether or not it comes true.

Spread stakes across the whole story — don't front-load them all. Most stakes should land in the first half; the second half is the ride to the end. Adding a new stake mid-story is "dropping a dead body" — it refreshes tension without requiring a dramatic plot event.

Surprise, suspense, and the inevitable ending

• Every moment of genuine transformation is inherently a surprise — the audience didn't see it coming.
• The best surprise feels both inevitable and unexpected: plant A, B, C, D early so the audience can connect the dots only when you want them to.
• Hide the setup so it can't be assembled until the reveal — then the audience thinks "of course" rather than "where did that come from?"
• Suspense is distinct from surprise — it's prolonged wondering. Build suspense deliberately, then deliver the surprise inside it.
• Knowing the ending doesn't kill a story. When Harry Met Sally tells you the outcome in the first scene; the journey is still worth taking.

Holding attention in business

No one wants to hear what you have to say — assume this and become relentless about earning attention. Four methods that apply to every talk, pitch, keynote, or all-hands:

• Stakes — as above; they work identically in business storytelling.
• Surprise — Steve Jobs engineered surprise into every product reveal. Plan at least one moment the audience doesn't see coming.
• Suspense — withhold the resolution deliberately; don't rush to the answer.
• Humor — most people want to have been funny, not actually be funny, because being funny requires risk. Two accessible techniques that work in business:
  • Nostalgia: describe the past state of your industry honestly; historical absurdity is reliably funny and demonstrates expertise.
  • Rule of three: expected, expected, unexpected — the third item lands as humor without requiring a punchline.

Storytelling in business contexts

• Don't try to match content to content. Match theme, meaning, or message — then snap a personal story into the business point. A scientist told an apple-shopping story to sell laboratory tubes and got more leads than four data-presenting colleagues combined.
• The snap — the moment the audience realizes "you were talking about apples but you meant tubes" — creates a powerful, lasting mental anchor. Every time those leads walk into a grocery store, they think of that company.
• Build a personal interest inventory: know which facts about yourself have wide addressable markets (married, parent) and which have intense niche resonance (marathoner, elementary school teacher). Work them in organically when answering ordinary questions — don't announce them.
• A 30-second personal anecdote embedded in a corporate narrative transforms a spokesperson into a human being and changes how an audience receives everything that follows.
• Two approaches to business storytelling: bricks (build a vault of stories over time, then deploy them as situations arise) vs. band-aids (find a story on demand to solve one problem). Bricks make you a storyteller; band-aids make you a repeat client.
• The band-aid process: ask what feeling you want people to have about the thing you're presenting, find a story in your own life that produces that feeling, then snap it over.

Homework for life

• Every day, identify one moment worth telling as a story — even a minor one. Write it in a spreadsheet: date in column A, one screenful of description in column B.
• The prompt: "If someone kidnapped my family and demanded a story about today before returning them, what would I tell?"
• The goal is not to collect stories; it's to develop a lens that sees story-worthy moments in ordinary life.
• Matthew started finding 1.8 moments per day; after 12 years, he finds 7.6 — not because life got more interesting, but because the lens sharpened.
• About 10% of recorded moments become stories or parts of stories. The other 90% preserve your days, surface behavioral patterns, and allow old memories to rise back up.
• Once you start looking through a storytelling lens, dormant memories from years earlier resurface and become available — the lens works backward as well as forward.
• Tag recovered memories separately (e.g., MEMORY in caps) so they don't get confused with current entries.
• Practical habit: check in at lunch (what happened this morning?), when you arrive home (this afternoon?), and in the evening (since then?). Don't wait until bedtime — specific moments get lost.
• Time doesn't fly; it goes by unaccounted. People who feel their children "grew up overnight" are losing those days. Homework for life is the act of accounting for them.

Public speaking and nerves

• 98% of nervousness occurs before you begin speaking. Once you start, it almost always falls away — even for very famous performers.
• Knowing this is genuinely relieving: the experience you're dreading is almost entirely the anticipation.
• Preparation reduces nerves. The most effective method: record your talk and listen to it passively (while cooking, commuting, folding laundry). It seeps in without the frustration of active repetition.
• Passive listening creates the same kind of deep familiarity that lets a person watch When Harry Met Sally for the hundredth time — you know every scene, but you're still in.
• Speakers almost never forget content; they forget transitions. Identify every move from one section to the next and build a mnemonic only for those.
• Avoid memorization — it produces the most tortured speakers. Know your scenes and your transitions; let the words find themselves.

Starting every story

Open with two things, every time:

1. Location — one word activates imagination and implies a thousand details. You don't need to describe the room; naming it is enough. The audience builds it themselves.
2. Action — something must already be happening. Not context, not credentials, not a rhetorical question — action. A big spaceship shooting at a small spaceship. A police officer chasing a man across a roof.

This combination signals to the audience that a story has begun, which earns silence and attention. It is especially valuable for anyone who has to work harder to hold a room — the "movie's on" signal crosses demographic lines and creates space for people who are too often talked over.

The case for saying yes

• Saying no to an unfamiliar opportunity assumes you already know what's on the other side of the door — which you don't.
• A yes can always become a no after you've stepped through and looked around.
• The best stories don't come from doing extreme things; they come from noticing what happens in your head during ordinary moments. Saying yes expands the number of moments available.
• The things that frighten you are most often the things most worth pursuing. When an opportunity feels frightening, run toward it.
• Yeses chain: saying yes to one uncomfortable thing forces you to meet people and enter rooms you'd never otherwise encounter, which opens entirely different doors.