Becoming a Better Storyteller

Adam Davidson recently stopped by the Every Discord to give a talk for subscribers about how to become a better storyteller. This article is a summary of his most actionable ideas.

Adam Davidson wants to help you become a better storyteller. He believes it’s a non-negotiable skill in the 21st century economy: “Back in the ‘60s, Don Draper could be a storyteller, while the rest of us just had to do our stupid job,” he says. “Now, in my view, we all need to be storytellers.” 

Sounds great, in theory. Until you remember that telling a good story is really, really hard. We all know that feeling (at least I know I do): gearing up for the big interview, the big pitch, the big product launch, channeling our inner Don Draper, ready to wow our audience with our storytelling prowess… only to fall flatter than a new comedian bombing their first set. 

You know who else knows that feeling? Adam himself. He’s told stories at the highest level in pretty much every medium you can think of: print, as a writer for The New Yorker and author of the book The Passion Economy; audio, as a journalist for This American Life and one of the co-founders of the popular Planet Money podcast; and even film, as a consultant on projects like The Big Short. 

And as he points out, even he and the greats that he’s worked with in all of those fields⁠—Ira Glass, Alex Blumberg, Adam McKay⁠—don’t nail it on the first attempt.  

“If you're in a story meeting, you're going to hear some of the dumbest worst story pitches of your life,” he says. “I’m working on a project with a big director right now, and if you could see our texts, you’d see⁠—it’s just not there yet.” 

Adam wants to help more people bridge the gap from “not there yet” to awesome, compelling, persuasive storytelling. The question, of course, is how do you get there? He and his business partner JP King joined us on the Every Discord to share some of their favorite frameworks for building a better story in business. 

Like most things, it starts with using the right template. 

Lesson #1: Find your minimum viable story 

Most of us learned in school that a story has a beginning, middle, and end. Adam’s version is a bit more specific⁠—and more actionable: 

Person + setting + an outcome that matters (also known as stakes).

This is the simple formula that drives all storytelling, from Disney movies to pitch meetings to Super Bowl commercials. “There’s a person, in a specific place and time. The person wants something. They might get it, they might not get it, and it matters to them whether or not they get it,” he says. 

Adam and JP call it the minimum viable story formula. And as Adam points out, it’s a formula that is hard-wired into our brains. Humans are, as a species, “absolutely obsessed” with this simple pattern: a human being, in a place and time, who wants a thing, and it matters whether they get the thing they want, or they don’t. 

So it’s no wonder something so elemental to the human condition can have such a big impact on human behavior. Think of Apple’s early ad campaigns, telling the story of the bold nonconformist, breaking free of the stifling status quo with their choice of hardware. Think of the story of the housing crisis: millions of homeowners pursuing their vision of the American Dream, only to have it slip through their fingers. 

You can apply the minimum viable story formula to your life, too: whether you’re a manager rallying the troops for an ambitious group project, or a job seeker prepping examples for an interview for your dream job,  just ask yourself: 

1. Who is the protagonist (maybe it’s you, maybe it’s someone else) 
2. Where and when are they? 
3. What do they want? 
4. Why does the outcome matter? 

Let’s use a story you might tell in a job interview as an example. You might try to tell a story like this: “I worked on that project and then when we shipped it it was really successful.” But that doesn’t have much oomph. It’s not going to be sticky.

You can supercharge your story by applying the minimum viable story formula and filling in more of the who, the where, the what, the when, and the why. For example: 

“My team and I had been working on a new feature for months. It was a key part of our product roadmap, and we knew that getting it right was the difference between closing our Series B and not. I remember the day after we shipped it—the whole team had our eyes on the user count, and when we saw we got 10,000 sign ups in the first ten minutes, we knew we nailed it.” 

You can see how the second version packs a bigger punch. That’s because it situates the listener in a place and time, with a strong sense that what’s happening matters. And that’s the minimum viable story formula at work. 

Lesson #2: Dial in your details 

Once you’ve got the basic foundation of your story in place⁠—you have the who, the where, the what, and the why⁠—the next step is to fine-tune the details you use to bring that minimum viable story framework to life. 

As Adam points out, finding the right details⁠—and the right amount of detail⁠—can be a balancing act. “The number one problem with stories is too little detail,” Adam says. “The number two problem is too much detail. 

To go back to the interview example above, you’ll notice that Adam didn’t dwell on where the job seeker sat in the office, or what the team had for lunch that day. He chose his details strategically, to support the story’s objective: helping the listener (probably a hiring manager) understand just how much the project that this interviewee worked on outperformed expectations. 

As JP points out, a big part of dialing in your details has to do with knowing which details are going to mean the most to your audience. “You're always telling it to someone,” JP notes. “And the best writers always have that person in mind when they're writing.” 

If you’re in an investor meeting pitching your software product to venture capitalists, you’re probably not going to go deep on the specifics of your product’s code base; you’re going to focus on the target customer, what their problem is, and how you’re solving that problem better than anyone else on the market. If you’re a manager trying to rally enthusiasm for a new initiative, you’re not going to focus first on the mountain of tasks that need to get done; you’re going to highlight how much easier everyone’s lives will be once the change is implemented. 

When choosing the details you add to your story, it’s important to keep in mind how familiar your audience is with the subject matter you’re talking about. Add too much detail for a sophisticated audience, and you risk boring them; move too quickly for an audience that is encountering the subject matter for the first time, and you risk losing them. 

The phrase “know your audience” gets used so much in storytelling circles, it’s beyond cliche at this point. But when you understand why understanding your audience matters⁠—and how it should shape your approach to storytelling, specifically when it comes to the details you include or exclude in your story⁠—you will be able to make it work for you. 

Once you’ve dialed in your details in your story, the next step is to think about raising the stakes.

Lesson #3: Set your stakes with the five whys 

We’ve talked several times in this post about “stakes”⁠—the “why it matters” part of the minimum viable story structure. Stakes are essential to the storytelling process, because they’re how you get your audience to care about what happens in the story⁠—and, by extension, to care about the message you’re trying to convey. 

If you want to convince an investor to back your company, that investor has to care about what’s at stake for the customer you’re serving. If you want to convince a customer to buy your product, that customer has to care about what’s at stake for them if they do it⁠—or don’t. To return one more time to the job interview example, if you want the hiring manager to believe that you have the skills they’re looking for to fill the position, the hiring manager has to believe that the work that you did in your past roles had a meaningful impact. 

A framework that Adam and JP recommend for getting to the stakes of your story is something called the Five Whys. To use it, simply start telling your story and then ask yourself this one question, five times: Why does that matter? 

How do you know you’ve gotten to the really core stakes of your story? When you’ve gotten to a place where the stakes are clear enough that even someone who lived 1,000 years ago can understand them⁠—even if the subject matter you’re talking about seems extremely complex or contemporary on the surface. 

“You could be talking about your new NFT fund, and there are maybe a thousand people in the world who understand the jargon. But you should be able to get to a place where the stakes are articulable to a peasant in rural India a thousand years ago,” Adam says. 

“The essential needs tend to be universal, you know?” he continues. “Love and death and belonging, etc. That doesn't mean that's where you keep the story. You want to keep the story in a specific detailed place in time. But you want to know that that's when you know, you're really scratching that deep, formative place.” 

Lesson #4: Build up your sensor for storytelling 

A final thing to note is that none of this comes naturally. 

“I always like to point out that I don't think that this is an inherent skill,” Adam says. “The difference between great storytellers and not great storytellers is just that they told a lot of stories badly, and then told them more, and then told them a little less badly.” 

Adam references a popular excerpt from an interview that renowned radio journalist Ira Glass gave on the creative process. “The very act of feeling like you're a crappy storyteller is a very promising thing, because it means you have some intuition about what a good story is,” Adam says. “And at the end of the day, the key to telling good stories is to build up that muscle that that sensor in your heart and your brain that you know what a story is.”