Andy Raskin on the art of strategic narrative

Andy Raskin is a legendary strategic narrative consultant whose clients have included Salesforce, Uber, Square, Yelp, VMware, Intel and General Assembly, as well as venture-backed companies funded by Andreessen Horowitz, First Round Capital, GV and other top investors.

Whenever I need to work on a presentation, I return to Andy’s crystal-clear 2016 post, The Greatest Sales Deck I’ve Ever Seen. He delivers a similar message in 2015’s Want a Better Pitch? Watch This (But, trigger warning: That 2015 post highlights a guy who is now busy kneecapping the federal government as fast as he can.) I’ve used the narrative structure Andy outlines in those two posts countless times, and I frequently recommend them to writers and content creators I’m working with. 

Here’s a more recent video of a 30-minute presentation where Andy shares his latest take on these ideas and his framework.

I overlapped with Andy when we were both contributors to Business 2.0, back in the dot-com days, although I didn’t know him well then. I took a class from him on content strategy sometime in 2015, and he’s been kind enough to stay in touch since then.

When I started doing this series on content pros, I knew I wanted to interview Andy. Even though he’s not a content guy per se, his approach to using story as strategy is something any business writer could benefit from. I know I’ve learned a lot from him.

So I was thrilled when Andy made time for me earlier this year. Here’s an edited version of our conversation. 

This is the latest in a series of interviews I'm doing with top content creators, editors, and writers. To get these posts in your inbox as they appear, subscribe now!

Dylan Tweney: Thanks for making the time to talk, Andy. So, tell me what it means that you do "strategic narrative."

Andy Raskin: The traditional way people pitch their companies is what I learned in business school. It's a formula that comes in various packages, but it's basically: You have a problem, I have the solution, and let me tell you why it's the best.

I call this the "arrogant doctor" approach. The metaphor is the doctor curing an illness, and we're bragging about why our cure is the best. This approach is great for most things. Like, I was shopping for a soldering iron the other week on Amazon, where each vendor lists all their great features, and I made a purchase decision based on the ones that mattered to me. This is how we buy in many situations.

But I started to see that really successful founders, starting with (Salesforce.com founder Marc) Benioff, were doing something different. When he started Salesforce, Beniof’s pitch was, "It's the end of software." This is not the arrogant doctor approach. In fact, this is not about Salesforce's product directly at all. It's a story about the world. It's a story about an old mindset—software as this thing we're going to code, buy, host, maintain, do the upgrades, run on our computers—shifting to this new mindset, which, of course, he called the cloud.

Benioff crystallized what was happening in the world in a boiled-down way: old mindset, new mindset. Sometimes I call it "old worldview, new worldview."

Dylan: That Salesforce story is also stated provocatively, right? It's not just that software is now cloud-based. He's actually saying software is dead—which is not really true, but it's certainly attention-getting.

Andy: Yeah, it's got that blasphemous edge to it, and that's very scary for many leaders. Not everyone is comfortable going that far. But I think all the good narratives have that property to some degree or another. In a sense, the most powerful narratives are always “wrong,” in that they’ve sacrificed completeness for brevity.

Dylan: How do you know if your company needs a narrative versus a regular sales pitch?

Andy: First, I don't think those two are mutually exclusive. What I would say is that the narrative was the core of Benioff's sales pitch. It just was a different structure.

I think the arrogant doctor approach is great for business-to-consumer (B2C) things where there's very limited interaction and the product is relatively simple. But the arrogant doctor starts to break down for B2B. Take a product like Salesforce, which has thousands of features. The buyer is a group of people, each with their own problems to be solved and values they want out of it.

This arrogant doctor approach runs into problems because: Whose problem are we solving? And these B2B platforms tend to be complex — if we make a claim that "ours is the most blah blah blah," it’s very difficult for buyers to validate those claims.

In these situations, what those who've adopted Benioff’s approach are doing is championing a movement. They're getting all the buyers to agree on where we're going. They’re creating alignment in the buyer group. They're setting the terms of how we'd even evaluate a product that will help us get there..

And not just alignment among buyers, but also across the company. Most of my clients  are CEOs of business-to-business (B2B) companies, typically Series B up to public companies, where they've got large numbers of people who they want to align on the story.

Dylan: OK, so tell me more about that. Some might think that what you're doing is a marketing function, but you're not working with marketing—you're working with the CEO.

Andy: I wouldn't say I'm not working with marketing. But the way I structure my engagements is that the CEO is the leader. The CEO is the one who's spending the most time with me, at a desk or on a Zoom call, where we're building the narrative together and then iterating on it.

The first line of feedback and input comes from a small team that usually includes the head of marketing—very important—but also head of product, head of sales, etc. Sometimes there’s a co-founder or COO type person, too. So it’s not just marketing.

When this is seen as just a marketing thing, it's more prone to fail. We want this to be the story we're telling everywhere, not only for go-to-market, but also, for example, for guiding the product, how we talk to investors, how we talk to recruiting candidates. Everything we're doing and building should be driven by this. 

Dylan: So the narrative is not just generating alignment among customers so they'll buy something, but also internal alignment within the company. 

Andy: Right. I think traditionally, the story, maybe because it has words, is seen as a marketing thing. And it is a marketing thing, but it's not only a marketing thing. The way I see it, the story is very much a leadership thing, a strategy thing. 

When it works, it becomes a guiding light for everyone in the company, informing how they make decisions.

Dylan: You told me before our conversation that you typically work on sales decks, not on messaging documents, mission statements, or things like that. Why is that?

Andy: There are a lot of these templates of things we're supposed to do that have gotten built up over the decades. The question is this: In what format are we going to write this thing down such that it becomes the thing everyone's talking about? The traditional answer is to put it in some internal document that the world never sees. Some marketers call it a "messaging house." It's usually a chart with labels on the left: this is the problem we solve, this is our mission, this is differentiator number one, differentiator number two, and so on. The idea is everyone is going to come back to this and pull words from it when they want to talk to someone. 

In my career, people wouldn’t actually come back to that internal document, especially people outside of marketing. And even if they did, it was very hard for them to take these pillar messages and construct something like a sales deck or website and have it be compelling.

I experimented a lot and eventually came—for my work with B2B clients—to the sales deck as the core narrative asset. 

This is controversial. Many people see the sales deck as the output of some more fundamental strategic document. I'm talking about the high-level, simple thing that we all can use to guide decisions when the CEO may not even be in the room. I found that the sales deck could do that.

Dylan: That makes sense. The sales deck also has the advantage that it's an asset that a lot of people are looking at all the time. So it becomes a very good place to put your core messages.

Andy: Right. Especially in these B2B companies. If the messaging is just in marketing, then it's like marketing is imposing their will on sales, and we don't really know how this is going to land. 

This is almost going the opposite way, saying, "Hey, let's get the message in sales right, and then marketing, you take it and go from there."

Dylan: So you're dealing with the CEO plus a small group of people who are acting as a sounding board. How do you bring those people together? How do you help drive people towards consensus? 

Andy: A big influence in my life was how we changed the way we ran meetings back when I was at Business 2.0 as a writer and editor. The weekly idea meetings there would be run by Josh Quittner, who would sit at the head of a long conference table with his lieutenants, then the line editors, then the copy editors, and the freelancers and writers at the end. He would go around and say, "Okay, who has an idea?" Some poor soul would raise their hand and start talking, and about five seconds in, one of the lieutenants would start criticizing the idea. Then others would join in the attack, and pretty quickly people got very scared. No surprise that we had a hard time coming up with good ideas: we were lucky if Josh assigned one or two.  

At the time, I was taking an improv class, which is the opposite approach. In improv, when an idea comes out, it's our job to make it a great idea, whatever it is. We're supposed to just do the best we can with "yes, and."

So I proposed a new way of running the idea meeting. Everyone would write their idea on the board first, just a headline, so we knew how many ideas we had and could divide the time so that everyone’s ideas could be heard. Then we agreed that when Josh called on people, they got 90 seconds to talk without any interruption. At the end, people would vote for their favorite ideas, but this was non-binding. Josh would still say, "Okay, as editor-in-chief, I want to assign these stories. I'm not sure about the rest," and he would explain why. 

We measured how many actual assigned articles came out of meetings run this way, and we typically got 10, which was a 5x improvement. As for why, I think it was a combination of allowing space for ideas to breathe before being attacked, but also getting to hear clearly from the leader about why decisions were made.

When I'm gathering feedback from a team now, I ask two questions: "What's working?” and “What's not working?" I have them write down their answers before any sharing. This might be the key thing—writing down the answers. 

Then I go one by one and have them share first what's working, because we always want to jump to why it sucks, but I want people to focus a little on what's good first. Then I go around one by one and ask each person to share, and no one else can talk while they're sharing.

People have told me afterward how much they love being in that kind of meeting because they got to talk and felt seen and heard. 

Then the CEO and I go back together separately and say, "Okay, how do you want to respond to that? Do you want to take that suggestion? Do you have a reason why not?" And then we'll make a new version and come back to them and say, "Okay, here are the decisions, and here's why." In other words, there’s a clear break between gathering feedback and reacting to feedback. 

It's about creating a forum for the participants to feel heard and have their space, but also the leader having the authority and mandate to make the call and communicate it.