The Question That Improves Every Pitch

Learn More About HubSpot's Sales Email Template Builder
Andy Raskin
Andy Raskin



When a pitch goes badly -- sales pitch, investor pitch, plea for company resources, whatever -- there’s usually a specific moment when it falls apart.

Before that moment, your audience gives you the benefit of the doubt. After that moment, they’re tuned out. You can almost feel them turn against you.

I’ve noticed that nine times out of 10, when things go south, it happens at a single, identifiable point in the story:

The moment when you introduce the thing you’re pitching.

Why Does This Happen?

Let’s take for granted that the thing you’re pitching -- your solution -- is super compelling. We’ll assume also you’ve laid the groundwork in your pitch by describing a big problem that it addresses. (I prefer the “Promised Land/obstacles/gifts” framework versus the more common problem/solution one, but what I’ll discuss here applies to both.)

When most people pitch, they introduce their solution as an assertion. It usually sounds like this:

So to solve that problem, we’re building X, which does … "

Introducing your solution this way seems obvious and straightforward. And certainly, most pitch advice tells you to do it.

However, I regularly see negative audience reactions immediately after the solution is presented this way. Here’s why:

  • You become less likable: Stating categorically that you’ve got the solution to a big problem -- especially if you’re just starting out -- can make you appear arrogant and/or naive. Even if you’re correct, your audience will be skeptical.
  • You invite attacks: An assertion prods your audience to ask, “Is he/she right?” In other words, the assertion invites people to hunt for reasons you’re wrong. And if there’s one thing skeptical audiences (read: VCs and potential customers) love to do, it’s find ways that you’re wrong and, by implication, they’re right.
  • Your credibility on everything that follows takes a hit: You’ll need to offer evidence that your solution is promising (traction, market size, etc.). But because you’ve already introduced your solution as correct -- even implicitly -- everything you say from that point forward is contaminated by bias. Your audience will be thinking, “He/she is pushing this solution, so of course he/she’s going to handpick data that supports his/her case.”

A Better Approach: Your Solution as a Question

Any time I’m pondering how to get an audience engaged, I go back to basics. For me, that means consulting the storytelling wisdom of the world’s modern god of audience engagement, "This American Life" creator Ira Glass.

According to Glass (and other narrative theorists), the secret to audience engagement is building dramatic tension. How do you do that? By asking and answering questions:

The whole shape of the story is that you’re throwing out questions to keep people watching and listening, and then answering them along the way." -Ira Glass

So how can we introduce our solutions as questions? I went looking for speakers who do this, and found some illustrative examples:

1) Airbnb founders Nathan Blecharczyk, Joe Gebbia, and Brian Chesky

Here’s Airbnb co-founder Brian Chesky recalling his now-famous founding story, in which he and co-founder Joe Gebbia offered up air mattresses to traveling designers:

We had this idea that the designers coming to attend the conference needed a place to stay-- we had no money -- so what if we created a bed and breakfast for the design conference?" -Airbnb co-founder Brian Chesky

Chesky’s not pitching, of course, but you can imagine how, back when he was, framing Airbnb as a question would have drawn audiences in.

2) Uber CEO Travis Kalanick

Next, check out Travis Kalanick pitching Uber’s car pool service, uberPOOL, in his February 2016 TED talk, "Uber's plan to get more people in fewer cars":

And so we started thinking about, well, how do we make those two trips and turn them into one. Because if we did, that ride would be a lot cheaper -- up to 50% cheaper -- and of course for the city you’ve got a lot more people and a lot fewer cars. And so the big question for us was: Would it work? Could you have a cheaper ride cheap enough that people would be willing to share it?" -Uber CEO Travis Kalanick

3) Harvard Business School Associate Professor Amy Cuddy

And here’s social psychologist Amy Cuddy, in the second-most popular TED talk of all time, “Your body language shapes who you are,” introducing the idea that posture can affect your mental state and how you interact with others:

… [C]an power posing for a few minutes really change your life in meaningful ways?" -Amy Cuddy

How to Frame Your Solution as a Question

As you can see, the general form of these questions is:

“So we thought, what if we built/tried X … ”

So I thought, (yes, dogfooding it!) what if I tried this with leadership teams that are my clients?

We immediately saw -- in investor pitches, sales conversations, change leadership speeches, whatever -- the opposite of what used to happen:

  • You become more likable: People are more willing to go on the journey with you when you project curiosity instead of certainty.
  • You invite collaboration: Now, when audience members voice their own ideas about how you might proceed, the conversation feels more like they’re collaborating with you on an experiment, rather than attacking you. The feeling of collaboration seems shared by speaker and audiences alike.
  • You build engagement and credibility: Because you’ve positioned your solution as a question, your audience starts thinking, “How will it turn out?” (That’s what Ira Glass meant by dramatic tension.) Everything that follows is more engaging and believable because you haven’t attached yourself to an outcome.

If you try this, let me know how it goes.

Based on promising results, I’m considering making this -- introducing the solution as a question -- a part of all the strategic messaging that I build. Still, I’d be fascinated to hear from others who try it. How did it go?

Editor's note: This post originally appeared on Medium, and is published here with permission.

Andy Raskin helps leaders align around a strategic story -- to power sales, marketing, fundraising, product, and recruiting. His clients include teams backed by Andreessen Horowitz, First Round Capital, GV, and other top venture firms. He's also led strategic storytelling workshops for leaders at Uber, Yelp, General Assembly, HourlyNerd, Neustar, and Stanford. To learn more or get in touch, visit

HubSpot CRM

Topics: Sales Pitch

Related Articles

Get Started with HubSpot's Sales Email Template Builder for Free


Powerful and easy-to-use sales software that drives productivity, enables customer connection, and supports growing sales orgs