Five Seconds, Real Stakes: Matthew Dicks on How to Tell Stories People Remember

Dicks says every story is about a singular moment, which he calls a five-second moment and says could even be one second. It is either a transformation, where you used to be one kind of person and are now another, or more commonly a realization, where you used to think one thing and now think another. The change builds over time through an accumulation of events, but the flip itself happens in a single instant.

The purpose of the story, he explains, is to bring that moment to the greatest clarity possible so the audience can experience the flip along with the storyteller. About 98% of the story is context for it. He says this holds for spoken stories, novels, films and television.

To illustrate, he tells a story from that very day. A fifth-grade student named Eileen, who has some anxiety, had not been called to the board, and when he asked her about it she replied, "First of all, I don't like that cheeky smile of yours." That was his moment of realization that she trusted him enough to joke with him, and he knew she was ready. He also reads Star Wars the same way: a boy with no religion who ends with one, switching off his targeting technology to trust the Force.

Dicks says true stories begin at the end, because you have already lived the moment. If your moment is that Eileen is ready to step forward, the opposite is that she lacked confidence, and the story runs between those two opposed points. This is why you can often guess a movie's ending from its first 10 to 15 minutes, as in a romantic comedy like When Harry Met Sally, and still enjoy the journey.

Knowing the ending also prevents the common mistake of simply reporting events in chronological order that lead nowhere. He adds that people will watch a movie dozens of times but never ask to see a PowerPoint twice, because our minds are wired for story. Children asking for the same book 50 times show the same instinct.

Change matters, he says, because it gives the story importance and a universal hook. If he and his kindergarten-teacher wife each reported their school days, they would hardly connect, since one is teaching the letter C and the other multiplication. But a story about someone finding confidence connects with anyone who has lacked it or tried to build it in a child or employee.

Dicks describes the dinner test: even on a stage, your story should resemble what you would tell at dinner, without performance tics like opening with unattributed dialogue or a sound effect such as "bang, the door opened". It can be a slightly elevated version, with more shape and fewer verbal fillers, but it should sound natural.

The second rule is that it must be your own story. A story about someone who is not in the room is close to fiction for the audience and allows no real vulnerability from the teller. He teaches the children and grandchildren of Holocaust survivors to tell stories about themselves and then show how a parent's or grandparent's experience changed their own lives.

Most vacation stories, Dicks says, are just recounting a trip and should be avoided unless a moment of change happened. Then tell only that moment: the Thursday dinner, not the beach, the scuba diving or the plane. The shortest version is the best, and quoting Kurt Vonnegut he says to start as close to the end as possible; his most frequent revision note is that someone started in the wrong place.

Stakes are what the audience should worry about or wonder about, Dicks says, and if they are not wondering what you will say next they are no longer listening. Business people often assume they have the room's attention because of their title, whereas he assumes 100% of the time that nobody wants to hear him. Star Wars opens with a big ship shooting a small one, and Hitchcock opens with a chase across a roof, so we care before we know who anyone is.

He offers a toolkit: an elephant at the start that signals something is at stake; a backpack, where you tell the audience your plan so they carry your hopes, like in Ocean's 11; breadcrumbs, which are hints such as the gun in the room; an hourglass, which slows time at the moment of greatest anticipation; and a crystal ball, which predicts a bad future, such as Eileen crying in front of 22 classmates.

Stakes should not be front-loaded in fear of losing attention; they should keep building, with most arriving in the first half so the second half can run like a roller coaster. He points to his Charity Thief story, where two-thirds of the action is just getting to a porch and needs every tool. Other stories, like performing as a stripper in a McDonald's break room at 19, have the stakes built in.

Dicks separates surprise from stakes: stakes make the audience wonder, while surprise is the moment they did not see coming and that then feels inevitable. Every story has at least one, because the moment of realization is itself a surprise for the teller. He says it is the best thing you can offer an audience and is usually ruined by storytellers.

Responding to Lenny's reference to David Mamet, he agrees that endings must be both inevitable and a complete surprise. You plant the information early, but hide it in a way that the audience cannot connect the dots until the reveal, after which they say "of course". He calls this ninja-level storytelling that is nonetheless teachable.

Dicks says that if you do not tell stories in business, you are mediocre like everyone else and likely to be forgotten. People love the buzzword storytelling but do not want to be storytellers, because standing apart from the herd feels risky. He contrasts two speakers at an education conference: a man who held up his childhood lunchbox and told a story of parents with nothing, which he and his wife still remember, and a fluent executive neither could recall 15 minutes later.

His example of a business storyteller is factory owner Boris Levin, who told a story about his son striking out in a Little League championship and then immediately running off laughing to get ice cream. Boris used it with his sales team, who sulk for days after losing a big deal, to say that it is fine to be sad but they must collect themselves and move on. The story worked better than a scolding because it revealed Boris as a caring father.

Dicks contrasts "band-aids" with "bricks". A band-aid person comes with a problem and wants a story to fix it, and keeps needing a consultant; Boris is building a vault of stories he can deploy later. Becoming a storyteller means gathering stories first and applying them to business afterwards.

Dicks describes working with Marsha Rakofsky, then Slack's director of corporate communications, on a narrative to compete with Microsoft Teams, which had copied the product and bundled it free. Marsha's idea came on a lonely pandemic Tuesday night after two glasses of wine, when she wrote three words on a napkin. She initially left that out, but when she added a 30-second anecdote to a lower-stakes talk, people came up afterward saying they felt the same way.

He also teaches a personal interest inventory: a list of things about yourself, each with an addressable market and an intensity of connection. Being married has a large audience but a moderate connection, while being a marathoner has a tiny audience but an enormously intense bond. The aim is to be full of color and flavor instead of "round, white and flavorless".

To work these in without sounding self-absorbed, answer ordinary questions with a bit of yourself. Asked how he is doing, he will not say "great" but "My fifth graders were actually decent human beings today," which slips in his job and a touch of humor. Whenever asked a question, he tries to include an item of his personality alongside the answer.

Dicks says that, because no one in business wants to listen to you, there are four ways to keep people listening: stakes, surprise, suspense and humor. He cites Steve Jobs as a master of surprise. Humor is the hardest because people want to have been funny, not to risk being funny: an executive he coached pulled all his jokes at the Javits Center after the first two speakers were not funny, though Dicks says he would have risen like a phoenix.

He has 26 strategies for being funny and shares two that suit business. Nostalgia, such as a 22-pound VCR, is always funny; he suggested a recruiting company open with 1983, when finding a job meant a teenager on a Schwinn delivering newspapers with help-wanted ads, then flip to today where every job in the world is on the internet. The CEO rejected it with "Nobody cares about the 1980s", which Dicks considers wrong.

The second is the Sesame Street game, "one of these things is not like the other": two expected items and one unexpected, such as a hardware store with shovels, nails and a faceless self-checkout machine. Dicks says to embed humor within a story so that if a joke fails you are still telling a story and people may not notice you tried.

Dicks tells of a biotech company that sells 12 correctly sized versions of an experiment tube while competitors sell one that must be retrofitted. One scientist skipped data and told a story about buying apples for his family, each wanting a different kind, and ended with "that's what my company does". He got more leads than the other four scientists combined, which unsettled the vice president of marketing until Dicks pointed out the leads would still want the data.

He adds that the story creates a lasting positive association: whenever those conference attendees buy apples they may think of the company. Dicks calls this advertising woven into people's lives without them noticing. Companies call him "metaphor man", although he is really taking stories from life and removing himself from them, leaving a metaphor, simile or example.

The technique, he explains, is speaking with adjacency: match theme, meaning or message rather than content. The scientist was not really talking about tubes but about people deserving what they need. When the audience realizes you were talking about apples but meant tubes, the snap is powerful, and Dicks says he uses it with students who are in trouble.

Dicks calls Homework for Life the most important thing he teaches, even for someone who will never speak publicly. About 15 years ago, worried about running out of stories, he began writing one story-worthy moment each night in an Excel spreadsheet with a date column and a long second column. He expected 12 stories a year and instead found far more than he could ever tell.

Over time he developed a lens: the first year he found 1.8 moments per day, and he now finds 7.6, not because life is more interesting but because he knows what to look for. About 10% of the entries become stories or parts of stories, yet the other 90% still hold on to his days. He argues time seems to fly because we fail to account for each day, and he prompts himself by imagining he must tell a story about today to get his family back.

He describes therapeutic benefits: slowing time and holding onto moments of his children's lives, and noticing patterns, such as realizing he "fights" with his wife silently by angrily installing air conditioners and mowing the lawn. A dull cookout with neighbors became the opposite half of a story when both neighboring couples announced divorces within a day of each other. He says old memories also resurface once you start looking.

To begin, he says, start right away and do it every day, even when the best you have is a cookout, and have faith that it takes years to build the skill. Capture things during the day, tag old memories as memories, and keep the data in a spreadsheet. Then find people willing to listen and start telling stories, since most storytelling is poor and storytelling is about decisions, not vocabulary.

Dicks says he has been nervous on stage only twice. For most people, he explains, 98% of nervousness comes before they begin speaking and falls away once the talk starts. Knowing that, and knowing that even famous performers are nervous backstage, can be a relief.

His main preparation technique is to record the talk and listen to it passively while shopping or doing chores so it sinks into memory the way a movie does. He can retell a story he has not told for a decade after one listen. He also listens actively for transitions, since people usually forget the links between sections, and may create a mnemonic where a transition is weak.

He recommends knowing the scenes and their order, and avoiding word-for-word memorization, since memorizers are "the most tortured souls in the world". Practicing aloud gets frustrating, so listening to yourself is a good substitute, and he notes it suits auditory learners especially.

Lenny mentions David Sedaris saying yes to everything for the stories. Dicks partly disagrees: great stories do not require crazy adventures, since most moments of realization happen in your head, such as while walking across a parking lot. Saying no, he says, presumes you already know what is behind a door you have never entered.

He argues that a yes can always become a no: step through, try it, and step back if it is not for you. At 100, he says, nobody will ask you to step through more doors, and you will regret those you passed. A yes can also create extraordinary causal chains, such as meeting someone who opens another door.

Lenny cites the quote "The cave you fear contains the treasure you seek." Dicks says he does standup because six years ago a friend suggested it, he replied no, then realized it was because he was terrified, and immediately wrote back yes. He has done it many times, performing at the New York City Comedy Festival, while the friend has never done it.

Asked for one tactical tip, Dicks says to begin every story with a location and an action. A location activates imagination, since saying "I'm standing in the kitchen" lets the listener supply a thousand adjectives, and action signals that the story is moving forward, like the opening of Star Wars.

He adds that people from marginalized groups have told him this opening signals that a story is starting, so the room gets quiet for them, like a movie beginning. He says that alone can make you roughly 50% better. He also shares that his favorite interview question is how someone got into their current job, which has made two people cry.

In closing, he suggests listeners create space for storytelling by asking people for their stories. When someone says that something like that happened to them once, they are really saying they wish someone would ask. In the lightning round he recommends The Heart of the Sea and The Tale of Despereaux, praises The Last of Us for its stakes, and quotes a fourth-grade teacher's line that a positive mental attitude will be your key to success.