Why Great Pitches Come From Customers

5 questions for pinpointing why they buy

A few months ago, the CEO of a growth-stage software company on the East Coast engaged me to align his team around a new strategic narrative—the high-level story they’ll pitch in sales, fundraising, recruiting, everything.

After a half-day kickoff session with the team, the CEO and I had dinner at a crab restaurant, where he told me he was concerned.

“How are we going to take all of my team’s divergent ideas,” he said, digging the meat from a stubborn claw, “and merge them into one simple, powerful narrative?”

To be sure, judging by the opinions expressed in the kickoff session, you’d think some of his team members operated in completely different markets.

Thankfully, experience has taught me that this is almost always the case, and not to panic. Because there was one voice we hadn’t yet heard from—the voice that has the ultimate power to align any team.

“Let’s see what happens,” I said, savoring the distinctive blue crab flavor that you miss after living two decades in San Francisco, “when we speak to customers.”

Getting Past “False Knowledge” of Customers

The strategic North Star guiding every great startup is a story—not about its team or its products, but about its customer. If that sounds trite, remember that most of the stories leaders traditionally tell—like mission, vision, and positioning statements—are structured as self-centered narratives (even in the grammatical sense) that cast the company as protagonist:

“Our mission is to be the most trusted provider of ___”
“We’re disrupting ___”
“The unique value we offer is ___”

Even when you pitch to investors, if you start with that kind of statement, they’ll eventually ask you to cut the crap and explain why customers have to buy. (Similarly, customers will be the recipients of your investors’ first due diligence calls.)

I’ve written in other posts about how to structure a customer-centric pitch narrative, most notably in the Greatest Sales Deck I’ve Ever Seen (which, as savvy readers point out, is not about a sales deck, but about the strategic story leadership tells).

Still, how do you align your team on a single, simple version of that story?

Toward that end, one of the biggest mistakes I made early on was making customer interviews optional. After all, the teams I work with typically boast millions of dollars in revenue. Aren’t their senior executives a reliable enough proxy for understanding the customer story?

I quickly learned that the answer was often no. One reason, I think, is that startups can accumulate what the venture capitalist Scott Maxwell, of OpenView, calls “false knowledge of the customer.” According to Maxwell, product and marketing people, in particular, are commonly “cloistered in the office,” insulating themselves from the real drama playing out in customers’ lives. (In contrast, salespeople are “out there touching prospects all the time,” Maxwell says, “and as a result have idiosyncratic knowledge of the people with whom they are interacting.”) Maxwell estimates that 50% of startups he meets have an inaccurate understanding of why customers buy:

“The problem is that no one believes they have false knowledge of the customer. But believe me, some of you reading this do.” — Scott Maxwell, OpenView

Of course, even if you have true knowledge of customers, members of your team may focus on different aspects, or simply express it in ways that sound divergent.

5 Questions For Aligning Your Team Around True Customer Knowledge

When we talk about “knowledge” of customers, what exactly are we trying to know? We are not, first and foremost, trying to know what they think about you, your product or your team (though that’s valuable knowledge, of course.)

Rather, we’re trying to name the drama playing out in customers’ lives that propels them to buy. This is different from what most pitching and positioning advice tells you, which is to brag about the superiority of a “solution” that you sell into a static world of “needs” and “problems.” Perhaps the very earliest adopters, who may be acutely experiencing the drama, have enough context to evaluate that sort of pitch; everyone else needs a story about why what you’re pitching matters.

For that reason, I now make customer input a part of every engagement I lead. After getting the lay of the land from the leadership team, we interview representative customers over the phone. While there are many valid methods for obtaining customer input, I like interviews because I get to hear the emotion in people’s voices and the words they use in regular conversation, both of which you miss out on if you just collect data on them or send out a survey.

I’m always honing the list of questions I ask, but these are the five—in this order—that I’ve found to be most effective:

#1. The “Promised Land” Question: How have we changed your life?

Of all the questions I ask, this is the only one that mentions “us.” It does so in service of getting customers to reflect not on the problems we’re solving or what we’ve delivered, but on why those things matter to the person we’re talking to. Answers to this question are gold because they inform the way you structure a statement about what should be the real mission—the “Promised Land” you’re committed to helping customers reach.

(What if you don’t have any customers yet, or if they haven’t yet experienced some new version of your product? Ideally, find some early adopters who can weigh in. Otherwise ask, “How do you imagine this would change your life?”)

#2. The “Change” Question: What’s different about the world now, such that what you just described is more valuable than it would have been, say, 5 or 10 years ago?

This is the biggie. Yes, the Promised Land may sound awesome, but what has changed in the world such that this person was willing to take extraordinary measures (i.e., buy) to achieve it? The answer to this question informs your strategic narrative’s change statement—the dramatic engine of a customer-centric positioning narrative—like Zuora’s “Subscription Economy” and Salesforce’s “No Software.”

#3. The “Happily-Ever-After” Question: What does winning look like for you?

We all want to tell a narrative that drives urgency, which is to say we want to hook people emotionally. In story terms, that means getting them to connect the change they cited in #2 with stakes—opportunity and risk. While #1 (about the Promised Land) probes for a concrete way customers want to see their life change (for example, if we’re talking to a ride-sharing customers, “Now I can get a ride whenever I want”) this one asks them to reflect on higher-level meaning (“I can get more done and be more successful in my career”).

#4. The “Hell” Question: How about losing?

You’d think this question would be a waste of time—isn’t losing just the opposite of winning?—but I’ve found that it isn’t. That’s because people describe vivid, emotionally charged scenes when they talk about losing—colleagues going crazy, bosses pulling their hair out, etc.—that are priceless for crafting the story. Teams I’ve worked with have used this kind of input to portray an “anti-Promised Land” (a.k.a. hell) that customers can identify with because they desperately want to avoid it. In other words, answers to this question and the one preceding (#3) help you frame the stakes that drive emotional buy-in and, as a consequence, urgency.

#5. The “Monsters” Question: What are your biggest obstacles to winning?

Aligning your company around a customer-centric strategic narrative means no one ever talks about disembodied “features” and “benefits”; instead, you describe your capabilities only in the context of how they help customers overcome obstacles to winning. Each obstacle, of course, is an opportunity: a monster you can slay with new product capabilities.

Customers, the Great Aligners

In the week following our crab fest, the CEO, his team, and I interviewed several of his early customers using the questions above. (How many is enough? My rule of thumb is to keep going until I can tease out words and ideas I’m hearing over and over; usually that’s between 5 and 10, sometimes more.) We then pored over the interview transcripts.

While I’ve learned never to expect unbridled unanimous agreement at any stage of this challenging work, at our next team session, the points of contention were orders of magnitude narrower. Nearly all of the big controversies had been resolved by the consistent themes—and words—we found in the transcripts.

As the CTO noted of one customer’s response:

“The way she put it, I just never would have thought to say it that way. But yes, that’s exactly what I meant in last week’s kickoff session.”

Interestingly, others rallied around the same point, even though they seemed to disagree over it the week before. I’ve seen this happen so many times now that sharing customer comments has become my favorite part of every strategic narrative engagement.

Next, the CEO and his team will be testing the new narrative in sales calls. Based on what we learn, we’ll refine the story and roll it out on their website, in recruiting discussions, and everywhere else. I’m hoping to visit again in a few months to check on their progress—and not just because it’ll be the start of soft shell season.

About Andy Raskin
I help CEOs and leadership teams align around a strategic story — to power sales, marketing, fundraising, product, and recruiting. My clients include teams backed by Andreessen Horowitz, KPCB, GV, and other top venture firms. I’ve also led strategic storytelling training at Salesforce, Square, Uber, Yelp, VMware and General Assembly. To learn more or get in touch, visit