Want a Better Pitch? Play This Game.
By: Andy Raskin
Tags: Storytelling, Entrepreneurship, Startup, Fundraising, Pitching

Want a Better Pitch? Play This Game.

Teaching pitch structure to CEOs, founders, and Uber engineers.

In the last four weeks, I’ve led strategic messaging workshops for Uber’s engineering team (on how to use narrative structure to more effectively pitch ideas to internal colleagues), for the founders of an Andreessen Horowitz/First Round-backed startup, and for international entrepreneurship students visiting Stanford.

In these workshops —as in my strategic messaging and positioning engagements — everyone comes in wanting to tell a more compelling story. But not everyone comes in knowing exactly what that means.

So I wondered: Is there a fast, fun way to give people a sense of how much better their pitches and strategic messaging can get by applying the fundamentals of narrative structure?

There are plenty of articles on the subject (Stewart Butterfield’s “We Don’t Sell Saddles Here” is excellent, and many people tell me they’ve benefited from my narrative breakdown of Elon Musk’s Tesla Powerwall pitch, “Want a Better Pitch? Watch This”). But I wanted an exercise I could do with a live audience that would get the point across quickly.

I searched every book I could find on the topics of pitching and business storytelling, to no avail. Then, on Amazon, I stumbled across a guide for elementary-school teachers called Super Simple Storytelling (by Kendall Haven). Near the back, I found a game called “Is it a Story Yet?” — designed for second-graders — that is now part of every workshop and strategic messaging project I lead. I’ve found no quicker way to get CEOs, founders, engineers, marketers, salespeople and product managers excited about applying storytelling craft to their pitches.

How to Play “Is it a Story Yet?”

Before starting the game, I go around the room and ask a few people to give their elevator pitches. Almost always, the pitches start and end with a product, a feature, or a service, or make reference to upending a category:

We do healthcare analytics. We’re going to disrupt payments. I want us to switch to a new database for the XYZ application. (internal project pitch)

My goal is to get attendees to re-frame their pitches around the difference they’ll make in people’s lives.

In the elementary school version of “Is it a Story Yet?”, the teacher reads the class a tale about a boy who forgets his homework. After each sentence, the teacher pauses to ask, “Is it a story yet?” Students get to vote, and explain why it is or isn’t.

For adult audiences, I use a more familiar narrative. I start the game by saying:

There’s a lightsaber that glows green and can cut down enemies. Is it a story yet?

Everyone agrees it’s not. “Why not?” I ask.

“Because there are no characters or context,” someone will usually say. So I add a protagonist, a couple of other characters, and some context:

There’s a boy who lives on sandy planet, and an old man shows up asking the boy to rescue a princess. He offers the boy a gift: a lightsaber that glows green and can cut down enemies.

Still not a story, everyone concurs, because the main character hasn’t set off to rescue the princess. So I add that piece:

The boy demurs until the bad guy’s forces destroy the boy’s home, killing his family. Now he goes with the old man to rescue the princess and stop the bad guy.

“We need a resolution,” someone always says. “How does it end?”

He defeats the bad guy and rescues the princess.

At this point, some people think we have a story. Invariably, though, someone will say, “But how did he defeat the bad guy?” Finally, we add this, which most people agree makes it a story, even if it lacks a few details:

He has lightsaber duels, gets himself and his friends out of a trash compactor and, finally, drops a charge that blows up the bad guy’s weapon. He defeats the bad guy and rescues the princess.

Now, to bring the lesson home, I return to the earlier “What do you guys do?” answers, and compare them to the first line in the game:

We all agreed that ‘There’s a lightsaber…’ wasn’t a story. And surely none of us, when asked to summarize Star Wars: Episode IV, would start with that. Yet when we look at our pitches, they’re all essentially variations on ‘There’s a lightsaber.’”

I was initially worried that this would come off as pedantic or shaming. But in my post-session feedback surveys, participants always cite the lightsaber among the most valuable takeaways.

“Is it a Story Yet?” as a Roadmap for Emotional Pitch Narratives

Naturally, this begs the question: How do you turn what’s essentially a product or feature description (“There’s a lightsaber”) into an emotionally resonant pitch story?

The answer is to describe the difference you’re making in people’s lives by filling in the same missing pieces we added to the Star Wars story:

Main character

Who is the person whose life will be transformed by what you’re offering? Usually this is your customer. If you’re a non-profit, it’s the people or communities you’re helping. Why now?

Why is the main character compelled to act ? In other words, what is causing that person to struggle? In Star Wars, it’s the Empire hitting Luke where he lives, leaving him with nothing. For Zuora, the subscription payments platform, it’s what the company calls the “Subscription Economy,” in which many businesses are shifting from outright purchase to renewable service plans. (For more on this, read For Startups: The Power of “Why Now?”) Promised Land

What will the world look like for your main character (customer) if he/she buys what you’re selling? In Star Wars, it’s the princess rescued and the bad guy defeated. For Airbnb, it’s that you’ll “Belong anywhere.” (For more on teasing the Promised Land, read: Master the “Move”) Obstacles and gifts

OK, now it’s time to talk about that lightsaber. But do it in the context of the obstacles you’ll help your character overcome to reach the Promised Land. Luke has to overcome a bunch of bad guys and their weapons to defeat Darth Vader. What obstacles will your customer have to overcome, and how does your product/service help? You’re Obi Wan, furnishing your customer with gifts that will help him/her reach the Promised Land. Evidence

The one element of a pitch story that doesn’t appear in the game is evidence. In pitch stories, unlike movies, the ending hasn’t happened yet. What evidence can you offer that you’ll make the story come true? (I discuss evidence in more detail in Want a Better Pitch? Watch This.)

Once these pieces are in place, it’s easy to construct a compelling pitch narrative, even if you have limited time. The format for an effective, bare bones pitch is:

For [MAIN CHARACTER], [WHY NOW]. So we thought, what if we could [HELP THEM REACH THE PROMISED LAND].

For example, the Airbnb founders’ early pitch story was essentially,

For travelers, it’s really hard to feel connected to the places they visit. So we thought, what if it we made it easy to find locals willing to host them?

If you’re successful, your audience will be thinking, “Sounds great, but how do you do that?” Now, having established what’s at stake, you’ll find people pay a lot more attention when you then talk about the cool features of your product (your “lightsaber”), describe the obstacles it helps overcome, and share evidence that you’re not just spinning fairy tales.