Strategic Storytelling is Product Management

Andy Raskin, a strategic messaging consultant, shares the five key components of an effective story and the secrets to getting buy-in for a big decision.

Here are the highlights:

  • How is storytelling an effective tool for product managers and how can they benefit from it? (5:50)
  • What are the key elements of a story that enables people to align behind change? (7:15)
  • What is “The Move” and how does it relate to the five most important aspects of a good story? (10:15)
  • What role does a villain play in storytelling and what is a practical example? (12:40)
  • Andy has written about the notion of the promised land, what is it and how does it evolve with a company’s long-term goals? (14:10)

And here's the transcript:

Andy Raskin: I'm Andy Raskin, and I help CEOs and their leadership teams get aligned around a high level strategic story. If you think about it, what you're doing as a leader and as a team, everything really hinges on whether you're able to tell a story that makes people want to join you. Whether that's fundraising, sales, recruiting, or building product. Strategic storytelling is product management.

Mike Fishbein: We've talked about the role of storytelling in product management throughout this podcast. Andy emphasizes some interesting nuances. I can't think of a better way to get started than for him to share his story about how he got into the field of storytelling.

Andy Raskin: Well I started out as an engineer. I was a computer science major in college. A friend of mine and I had an idea for an app, a Windows app, that we thought we could build a business around. Of the two of us, by the time this happened I'd been to business school and I spoke English, so I wrote the business plan. We sent it out to a whole bunch of VCs, and it did not go very well.

One day we get this rejection letter from this guy who says, "Listen. I rate every business plan that I get on a scale of one to 10. Yours is a one". Then he wrote, "Worst", just in case we weren't sure that one was the worst. Then in the margin he had actually printed out our plan and mailed it back to us, and in the margin he wrote, "Not a compelling story". We were very focused on the, "One", and really bummed about it.

But a couple weeks later I was walking by this Barnes and Nobel. There was this big sign in the window and it says, "For anyone who wants to tell a compelling story", and there's an arrow to this book. "Okay, that's us". I buy the book, and it turns out it's about screenwriting. It's a book called, "Story". Everybody in Hollywood has this book. I read it from cover to cover and I thought, "What if we tried rewriting our plan based on what he's saying?". We did it, and lo and behold, everything changes. We start getting invited to pitch. Our pitches go better. Within about three to four months we had a term sheet from a pretty well known VC.

This really kind of floored me. What is this story thing that really changed everything? Nothing about our product or team or business model changed. Only how we were conveying it. That got me really interested. I eventually went on to become a journalist after that company was sold. I started writing in different magazines about just all kinds of things that interested me.

Then though I got kind of drawn back into the tech world when a friend of mine at Skype was looking to tell a really great story to the eBay board. That led to me taking on a product management roll at Skype. Then I started getting really interested in the stuff, the story piece, which led me to product marketing. First at Mashery. Then eventually I started my practice about three years ago to just help teams on this very specific piece.

Mike Fishbein: At the risk of getting too meta, I asked Andy to break down the framework and strategy behind the origin story he just told.

Andy Raskin: I'm still working on my own origin story. I always tell it a little bit differently, and that's one of the messages I try to convey to people that I work with, is that you're never really done. You're always honing it and seeing how it plays for different audiences. What I've learned over time is that it conveys a few things that I like people to think about myself. One is that there are stakes around telling a great story. In my case it was about getting funded or not funded. For a lot of folks that's it, or in some cases for sales people it's making a lot of deals happen or not. Or for product people it's building a product that people are really excited about or not.

Another point that I hope comes across in that story, I will sometimes hit explicitly if I'm telling it to people I'm working with, is that you can get better. There's this quote by Bill Gurley of Benchmark about how the great storytellers have an advantage in business. How he's actually looking, when people are pitching him, he's actually looking for storytelling ability as one of the criteria to make his investment decision.

I think there's this idea that we're sort of born as a great storyteller or not. I certainly was not, and through that experience and lots of just having interest in it and practicing and learning more, I think I've at least gotten a lot better. I hope it comes across that anyone can get better at doing that.

The last piece is just that I'm somebody who's sort of interested and curious in a lot of things, and particularly in this stuff. In the story stuff and how it works.

Mike Fishbein: Although storytelling doesn't come naturally to Andy, he explains how being adaptive has helped him continuously iterate and improve. Why is this important to the field of product management?

Andy Raskin: If you're leading a product team or you're a CEO leading a team, leadership is really about enrolling others in change. "The world is like this. What if we could make it like that?". There's just so much wisdom in the fields like film and other narrative arts about how you engage people emotionally to bring them along on that journey. I think whether, if you're a CEO leading a team you're about, "We want to change the world in this way. How can we tell that story in a more engaging way that's going to make people invest in us, buy our products, join our team?".

In the product world, obviously the word, "Stories", has already become part of the job through user stories. But then can you also define the high-level story that really your product is making come true. That question I think is the big one that a lot of product people struggle with, and if they can really define it well then it really improves their ability to deliver a great product.

Mike Fishbein: Storytelling is about aligning people to affect change, Andy argues. It's about getting emotional buy in. Whether for building new features or starting a company altogether. What are the key elements of a good story or pitch?

Andy Raskin: I see it as five elements. Number one, the undeniable change in the world that's creating stakes for your audience. Number two is naming those stakes. What does it mean to win? What does it mean to lose? Number three, what is it going to take to enter what I call the promised land? What is the final battle we need to win in order, that the audience needs to win in order to reach the winning rewards?

The third one, your magic. What are the magic gifts you're going to give to your audience to help them along the way to reach that promised land? The fifth is evidence. What evidence can you provide to a naturally skeptical world that you can make this story come true?

In the world of movies, obviously every movie is structured pretty much this way. In Star Wars there's this change in the world. The Empire, you could take the first one. The Empire builds this Death Star and kidnaps Princess Leia. Stakes? Pretty much, evil wins or good wins. Everyone is happy, or everyone we care about is sad or maybe worse. The gates to the promised land is, "We're going to have to defeat Darth Vader". The magic that Luke is going to get along this quest comes from this helper. This helper in this case, Obi Wan, is going to give him light saber, Jedi mind tricks, his experience, all that stuff.

How do these play out for a business story? One of the greatest I think is a company called Zuora, which does subscription billing. If you ever hear their CEO talk, he always starts with what he calls the move to the subscription economy. He doesn't start by talking about his product. He doesn't start by talking about features or anything like that. He just talks about this change in the world that's happening. It's really outside of him, that that's affecting his customers. He talks about the stakes. What it means to win in that world and what it means to lose in that world.

Then once that stage is set he talks about his magic. The very different kind of customer record that Zuora offers as a base for winning in this subscription economy world, and of course many others as well.

Mike Fishbein: Andy outlines five key aspects of a good story. He also recently wrote an article about the move, which I asked him to expand on within this context.

Andy Raskin: Sometimes I find that those pieces at the beginning, the change in the world and particularly the stakes, are missing in a lot of pitches. The move is about making sure that those pieces are clear upfront. As an engineer I was really trained to make arguments and build my case first before making any claims. I think people like me, we tend to say, "Okay. It's got this feature. It's got this feature. It's got this great stuff. Therefore you're going to be able to enjoy these great benefits and this great life".

People who really tell strategic stories well do instead is, they start with what that great life is going to look like. Essentially the promised land. They move it up in their story before they start talking about features, or even their product. A great example of this, Steve Jobs did this every time he did a keynote. One of them, just one example was when he introduced the iPhone. Before showing the device he shows this two axis two dimensional graph with ease of use and smartness on the two axes. He shows how all of the current devices are not that smart or not that easy to use. He puts the iPhone at the top and says, "What if you could have a world where it was super easy and was super smart?".

Obviously he's going to have to make that story come true with the product. But by making the move, he gets people excited. They understand when they see the product, when they see things like gestures that he's going to show them, why those things matter.

Mike Fishbein: Moving the aspirational state to the beginning of a story primes the listener so that they understand why the rest of the story is important, and how it all ties together.

Andy Raskin: Yeah, and the features are supporting the story. You know, they're like the light saber. If we just sort of see the light saber apart from the whole story of Star Wars, if that was how we got introduced to it, we might not think that much of it. "Oh, okay. Cool thing". When we see it in the context of, "Oh. This is a really important piece of magic that's going to help us achieve our goal, defeating Darth Vader", then it takes on this whole new light.

Mike Fishbein: Another aspect of Andy's strategy is the concept of an antagonist. What role does a villain play in storytelling, and what is a practical example?

Andy Raskin: I mean I think the enemy is really the embodiment of change that causes the stakes. In the movies, especially in epics, it's some person and usually some evil person. Though it isn't always. If it's a love story this change is two people, like When Harry Met Sally or The Notebook, two people meet each other and that's creating stakes.

I actually prefer the term, "Change in the world", to, "The enemy", because it's not always some evil thing. In Zuora's case, that subscription economy is this change in the world that's creating stakes. It's not an enemy unless you fail to adapt to it. That's where stakes comes in. You see a lot of product messaging that's something to the effect of, "We're transforming payments", or, "We're reinventing finance". You get the sense, "Okay. They probably mean it's going to get better". But they're kind of punting on, "Better how?", or, "Worse how?", if you don't go with them. The change in the world has to be accompanied by, "What does happily ever after look like?", and, "What does Darth Vader winning look like?".

Mike Fishbein: Finally, Andy has written about the notion of the promised land. He's touched on this a bit so far, but I asked him to go into greater detail.

Andy Raskin: The promised land is, in the stories, let's go back to Star Wars again. The whole goal of the movie is defeating Darth Vader. Defeating Darth Vader is kind of like the gate to the promised land. If we can do that, we can enjoy this sort of happy life where good triumphs over evil. What is that for your product or for your company in terms of, what is the ultimate goal for your audience? What is the thing they have to achieve in order to enjoy the rewards of winning that you're promising?

The one great example I love to look at has been Uber, because Uber's promised land has actually changed over time in reaction to the way that Uber's strategy has changed and the way that we as consumers have changed. If you look at Uber's homepage from 2011, the promised land message is, "Everyone's private driver". You're going to have a chauffeur.

A few years later they introduce Uber X, and the promised land message changes to, "Moving people". Moving around. It becomes much more about mobility. If you can move, go wherever you want on-demand, then you enjoy the benefits of the promised land. The most recent messaging is something about, I think the exact wording is, "Your day belongs to you". They kind of up-leveled it into this higher-order, more having control over your life.

I think in 2016 we understand what that means because we have experience with Uber, and it has meant that in our lives. Not only for passengers, but also probably for drivers. Yet if they had started with that promised land back in 2011, I think we have no idea what they're talking about.

There's an interesting way that the promised land I think has to evolve over time based on strategy, strategic changes, and also changes in the marketplace and your audience's familiarity with what you offer and what it means to them.

Mike Fishbein: The promised land is a moving target so to speak. It evolves as the company's strategy and long-term goals evolve. I wonder what company is doing the best job at strategic storytelling and why?

Andy Raskin: Again I have to really point to Zuora. It's just amazing. You look at, you can pull up anything that Zuora does. I just pulled up the other day an interview that the CEO did on Jim Cramer's show, Mad Money. Jim Cramer's like, "Tell us about what you guys do", and Tien does not say, "We're a platform for doing this", or, "We're the ...", you know. He starts with the change in the world. He says, "Listen. We're moving from an economy where people bought things to an economy where people are using things on subscription and rental basis.

He's talking about what that means in the world, and Jim Cramer, his audience is saying, "Yes. I see that change and I see how it's creating stakes in my life and changing my life". Once that happens, he's prepared now to hear more messages. I think that is a really powerful lesson. That what you're selling is actually not your product, but is the change in the world and your ability to help people thrive in the midst of that change.

Mike Fishbein: Regardless of whether or not an argument or a position is innately worthwhile, using strategic storytelling to communicate is an effective way of impacting listeners and driving change. Next up is the benchmark. Let's see how Andy reflects on the next series of questions we ask all interviewees to ask themselves.

Andy Raskin: How do I eat my own dog food? Well, I think I'm in very much the same predicament that a lot of CEOs and product people are. I'm doing something that hasn't really been done that much before. There aren't that many people you meet who are making a living doing strategic storytelling training. I too have to, I'm challenged to put it in terms of, "What's the change in the world? What's the promised land that I'm offering? What are the stakes?".

I try to do that, the place where I do that the best is in the articles that I write on Medium and LinkedIn. There I'm always trying to write about someone that I'm helping who is struggling. It could be to pitch their enterprise software platform, or to raise money for their startup. I'm trying to show examples of folks who have done it really really well, and then how the person I'm helping is, they're taking those lessons and running with them.

I guess the way that I eat my own dog food is that I'm trying to not focus so much on, "Here's my technique. Here's my process". But what's at stake, and what does it look like when you win?

How do I get out of the office? Well one thing that I love to do is teach. I've been teaching this stuff at General Assembly for about the last two years in a class I call Storytelling For Success. I'm really pretty adamant about getting feedback after the class and changing it up for the next time. I'm always trying to see how the way I talk about this stuff can be improved, can be made easier to understand. I've learned so much from the students who come to these classes, as also from clients as well. Just about how I can convey this stuff so that it's more effective.

What am I reading right now? Well I read The New Yorker religiously. I love reading it on Kindle because it's just super easy to read, and I can literally get through a whole magazine. Whereas they used to just sort of accumulate on my floor. Recently, one of my favorite articles recently was this profile of Sam Altman written by Tad Friend. Just first of all how he's this really interesting character. But also how what he's doing at YC is really upending the whole VC world. I thought that was just a great piece.

What's a recurring product management nightmare that I have? Well, I'm not a product manager these days. But in the days that I was one and with the product managers that I interact one, I think one of the biggest fears is that you're going to kind of be building this roadmap, building out this product, and the leadership is going to somehow switch the story on you. That you're going to be building toward making a certain story come true, and the rules will change and you're going to have to now make another story come true. Which can throw your roadmap into disarray and all the rest.

I think the one way to avoid that nightmare is to consciously get on the same page with the leadership team about, "What is the story that we're making come true?". At least for a while, recognizing that, "We may have to change it, just like Uber has, when the market changes or our strategy has to change. But we're going to do it in a conscious way that we gain alignment on it every time before we go ahead and do that".

Mike Fishbein: Listeners can find out more about Andy on LinkedIn and Medium @Raskin. Or on his website, That's our show. Until next time, this is Mike Fishbein from Alpha.

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