The power of strategic narrative | Andy Raskin

Andy Raskin: The way I learned how to pitch in business school, and I think the way most people did is what I call the arrogant doctor. So you have a problem, a pain, I have a solution, a treatment, and I’m going to tell you why it’s better than all the other treatments. And the structure that I read about in these movies was different. Every movie starts with some kind of shift in the world, and I call this shift the shift from the old game to a new game. The archetypal example of this, I think in the business world, is what Benioff did with Salesforce. So he comes in and he says, “Hey, software is over and there’s this new world called the cloud, a new game, new rules. That’s the new way to win. And we’re going to help you if you’re in there.” This structure really is about defining a movement, and that’s very different from, “Hey, I’m going to solve your problem.”

Lenny: Welcome to Lenny’s Podcast where I interview world-class product leaders and growth experts to learn from their hard won experiences building and growing today’s most successful products. Today my guest is Andy Raskin. Andy helps CEOs and company leaders align their teams around something he calls a strategic narrative, which as you’ll learn all about in this episode, is essentially a simple story that helps people understand why they need your product. And with that helps you align your sales, marketing, and product teams along with your fundraising and even your hiring efforts.

Andy has worked closely with some of the most successful founders and companies out there, including companies like Gong, Dropbox, Uber, Salesforce, Square, IBM, and many others. In our conversation, Andy explains why most people are pitching their product completely wrong, why focusing on the problem you’re solving for people is no longer an effective pitch and how the strategic narrative helps you frame your solution in a much more effective way. Andy also shares a ton of examples of the framework in action, why focusing on categories and category creation is so limiting, signs your narrative needs to work and so much more. Enjoy this episode with Andy Raskin after a short word from our sponsors.

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Andy, welcome to the podcast.

Andy Raskin: Oh, thanks Lenny. So great to talk with you.

Lenny: You are quite known as someone that helps CEOs optimize their pitch, their story, their strategy, which we’re going to get deep into. But before we do that, can you just give us a little glimpse into how you found your way into this line of work?

Andy Raskin: I started as a coder. I was a computer science major, undergrad, a friend and I had an idea for an app. So this was like during the dot com years. So Windows app, and we coded a little prototype and we started, we put it out there, we started getting some users and we thought, “Oh, okay, maybe we can get some investments.” So of the two of us, I spoke English fluently. So we decided, okay, I’ll write the investor pitch. So I wrote the pitch, we sent it out and the reaction was really bad. One VC wrote back and said, “Listen, I rate every plan I get on a scale of 1 to 10, and yours is a 1,” and the next to the one he wrote in parentheses, “Worst,” in case we thought maybe that was the top of his rating scale.

Lenny: Brutal.

Andy Raskin: Yeah, brutal. But then lower down, so this was back when they would like you’d print, send the hard copy of the plan and they might mail it back with comments written in. And he had written in, “Not a compelling story.” A few weeks later, I’m walking by this Barnes & Noble and there’s a sign in the window that says, “For anyone who wants to tell a compelling story,” okay, that’s me. And there’s an arrow that points to these books and they turned out to be screenwriting books. I didn’t know anything about this, so I started reading these books and it strikes me a movie is a pitch. What is Star Wars a pitch for? It’s a pitch for be good, care about people, trust The Force in their terms. But I don’t have couple hours. I’m pitching a business. It’s very different. I’m not writing a three X screenplay.

So what applies, what doesn’t apply? I mean these are questions I think I’m still asking, but I did my best to take some of the learnings of how the movie was structured. It was very different from how my pitch was structured and kind of restructure it. And we did that and we sent the pitch out and we start getting more interest. It was really clear. And then we had a term sheet I think a few months later and I’m like, “What is this story thing?” That we didn’t change the product, it was basically the same business just sort of how we talked about it. That was really interesting to me.

I mean, over the next 10, 15 years, I thought about, “Hey, maybe I could do consulting with this.” CEOs who heard about this were asking me about it. But I still was like, “No. No CEO’s going to budget a line item for the story. That’s not a thing.” So I just didn’t do it for a really long time until eventually I was proven wrong about that.

Lenny: And how many years ago was this at this point?

Andy Raskin: So this was dot com. This was like ‘98 when I was pitching that company.

Lenny: Amazing. I think there’s a couple interesting tidbits about this. One is that interesting opportunities arise when you’re doing something you’re excited about. So you had the startup, it didn’t work out, but you had a problem that you solved for yourself and that led to another, a bigger opportunity for your career.

Andy Raskin: Yeah, totally.

Lenny: So that’s interesting. And then also just some of the best opportunities arise from solving your own problem, not planning to start something with it, but just like, “I have a problem.” Turns out [inaudible 00:07:44]-

Andy Raskin: Yeah, I think that’s same with you. Right, Lenny? You started writing about stuff and boom, that became the thing.

Lenny: Absolutely. It was not quite boom, but eventually it became boom.

Andy Raskin: Feels like boom from outside.

Lenny: Yeah, that’s how it goes. It always overnight for everyone else that isn’t here.

Andy Raskin: Right, exactly.

Lenny: Yeah. Okay, so let’s get into it. So you help CEOs at this point come up with what you call a strategic narrative and you help them not only come up with this strategic narrative, but you help their teams align around this strategic narrative. So let’s just start with what is a strategic narrative?

Andy Raskin: Yeah, you’d think, I’ve been doing this for 10 years, I’d have a very snappy definition of it there, and I don’t know if I’m really happy with … like I’ve ever found one that totally gets at it yet. The one thing I say is it’s this one story that the CEO uses to drive success in marketing, sales, but also product. That it becomes like a north star, strategic north star for product roadmap, for fundraising, for recruiting, really everything.

What I think is really interesting as a kind of qualifier is that this story has a certain structure. Like I said, when I found those screenwriting books, I sort of shifted the structure. And the traditional structure, the way I learned how to pitch in business school, I think the way most people did is what I call the arrogant doctor. So you have a problem, a pain, I have a solution, a treatment, and I’m going to tell you why it’s better than all the other treatment.

Not to say it’s not better, but just this is the structure of it, and it kind of sets you up for bragging. Let me tell you why it’s so great. And the structure that I read about in these movies was different. In the movies, every movie starts with some kind of shift in the world, in the character’s world. And I call this shift the shift from the old game to the new game. And the archetypal example of this, I think in the business world is what Benioff did with Salesforce. So he comes in and he says, “Hey, software is over,” meaning software in the sense that we’re going to own it and maintain it, “And there’s this new world called the cloud, a new game, like the new rules, everything has changed and that’s the new way to win. And we’re going to help you if you’re in there.” This structure really is about defining a movement and that’s very different from, “Hey, I’m going to solve your problem.”

Lenny: I think the Salesforce example is an awesome example of your approach. If they were thinking about it in the old way, what would Salesforce have done? How would they have pitched it if not for, “Everyone’s moving to the cloud, your dumb for using desktop software,”?

Andy Raskin: Well, I think they would’ve just come out and said like, “Oh hey …” I mean CRM by the way, was already a category. I mean, already Siebel was the huge giant of that space. There were already even companies doing it online, doing it through the web. And so they would’ve come and said, “Oh, we’re easier to install, faster to get up and running than Siebel,” or, “We have this much functionality compared to,” I think it was, was it NetSuite? Or, I don’t know. It was some early Salesforce-like thing that was out there. They would’ve done these sort of comparison things.

And Benioff, I mean he is a pretty proud guy. I think he did still say like, “Hey, we’re the number one CRM,” but wasn’t what they led with. They led with this story about this fundamental paradigm shift and, are you in or are you not in? And what they did was instead of just saying, “Hey, we’re better than,” they said, “Hey, all those others, those Siebel’s, they’re part of that old game. You want to play that software game? Be my guest, go buy Siebel,” and of course we know how it played out.

Lenny: So the crux of the approach is instead of, “Problem, solution, you should go do this,” it’s, “The world is changing, here’s where it’s going and we’re going to help you get there.” I want go in a little more depth of the framework. But before that, what are some other examples to give people a sense of like, oh, I see, I understand what this might be.

Andy Raskin: Yeah, so another great example and no coincidence, so is Zuora. So Zuora is the company I wrote about in this post called The Greatest Sales Deck I’ve Ever Seen, the CEO of Zuora, Tien Tzuo, was employee number 11 at Salesforce. So he learns this from Benioff. And he’s pitching, “Hey, in the old world, businesses operated on transactions. You sold things to people outright. In this new world,” he calls it the subscription economy, where people want the benefits of those things without necessarily having to pay for them. And of course gives all these examples of all the winners in this, look at all the winning companies. They’re all basically going to this new model.

And so he’s pitching someone like Ford and you can imagine they’re going to Ford and pitching a subscription for car service, which is quite different from just a lease. And they’re starting out with this. This is the big shift. Another one, team I worked with early on, and I think they’d agree their story came out of this work was Gong. So Gong everyone probably knows by now, they take the video recordings of all your sales calls and they stick AI onto it and come out with all these insights. And that story is, hey, goodbye opinions. Used to be a world where sales is run on opinions. Hello reality, that now all the winners are adopting this new mindset where we really have to see what’s really going on.

Lenny: In the Gong example, let’s say, what would they have done if they were going, “Here’s the problem, here’s the solution, here’s what we’re going to do for you,”?

Andy Raskin: Yeah, I mean that’s kind of what they were doing when they started out. And I’m not saying that didn’t work totally. I mean already by the time they started doing this, they were starting to become a big company. I remember Bendov said to me, “Listen, Andy,” they were around series B, I think this is around 2018. It’s like, “We’re going to be a huge company. The question is how huge. And I think that this narrative along the lines of Zuora or Salesforce, if we get this right, this is going to be a multiplier on our growth.”

So I don’t remember exactly the pitch beforehand, but it was very much like, “Hey, we’re going to record your calls. We’re going to get insights from them. They’re better than the insights you could get from Salesforce.” There wasn’t this kind of unifying kind of movement ideology that put it all in context. And what was really interesting was one thing, I don’t think they’d be upset if I shared, and maybe it’s known. Initially, they were seen as a tool for sales operations, for someone who’s going to record the calls and what this narrative did for them. And I think it was already starting to happen, but what it really coalesced was this is a tool for sales leadership.

Lenny: You talked about Zuora in the post you wrote, and I imagine many people listening are like, “Oh, shit. This is the guy that wrote that post that everyone’s always sharing with me about how to make a deck.” And I wanted to ask, how impactful was that one piece of writing for you in your career, just like as a tangent?

Andy Raskin: I had written some other posts on Medium in particular. Medium has changed quite a bit, but back then I found that I could write stuff there and get really a lot of people who were interested in what I was interested would sort of come in and create some noise about it. So I was already doing this kind of work for a couple of years, but that post immediately got something like 2 million views around the world and I started getting inquiries from teams all over the world.

And it was I think what really allowed me to say no, okay, I could do this work. That CEO’s would budget a line item for this. Because I think if you really understand that post, it’s not really about a sales deck, it’s really about this story that Tien, the CEO is telling everywhere and that is showing up in the sales deck and structuring it that way.

Lenny: I think it’s just another example that comes up a bunch on this podcast is just the power of writing and the power of content. Yeah, and you’re shaking your head.

Andy Raskin: Totally. I mean, I had a little mini career as a journalist, as a freelance writer and I really loved that. I actually, I took a class in New York called How to Write a Magazine Article, because I was sort of mid-career, I was curious. And the class wound up being more about how to sell a magazine article. And I found I really loved that, pitching articles, but one thing that was always a downer for me was there’s always this editor sort of deciding what’s going to be out there.

And when you work with a great editor, it’s great, they make yourself better and they’re priceless. But still there’s this intermediary. What started to happen, I think around when I started writing around 2013, ‘14, you start to see these platforms, like Medium, even LinkedIn where you can just write and have this audience and I think no way I could do this, the work I do if that development hadn’t happened first.

Lenny: I’m taking us off track, but I want to go a little deeper with this. I find that there’s kind of two paths to writing online. One is your path where you write one piece that just blows up like crazy. The other path is more my path where I just write consistently for a long time, and both work and most people try to go your path and they never succeed. It’s really hard to make something gets 2 million views, but you can go that path.

Andy Raskin: This is like you said earlier, hey, it seems like boom, but really it didn’t. So that was probably the 30th or 40th piece and they were gradually getting more and more traction. There was one I wrote before that about, it’s kind of dissecting Elon Musk’s pitch for the Powerwall, the battery that they sell. And that one got maybe few hundred thousand views and also was a big jump. And then the next one got some poultry number. So what I find is like, yeah, there’s this a while where you’re writing and it feels like you’re talking to nobody and then gradually it grows and you’ll have these peaks, but then over time is where the magic is.

Lenny: Okay, I’m really glad you pointed that out, that it rarely is just you write one thing and it’s boom.

Andy Raskin: I’ll also say, sorry, because I worked in a magazine, I haven’t done a newsletter because that idea of having a deadline all the time and constantly having to, we used to call the magazine Feed the Beast, I feel so free not to have that. So for now at least I haven’t done that.

Lenny: I know that well, so let me take us back on track and let’s talk about just the high level framework here. So you talked about, it starts with this idea of tell people worlds changing, join this movement. What’s the simple way to think about this, the pieces of this strategic narrative framework?

Andy Raskin: A lot of times people will contact me, say, “Hey, I tried it, didn’t work.” Well, one very common thing, at least earlier was they would basically just take the Zuora deck, they’d get ahold of it and just put their logo on it. And so that’s not going to work. One thing is we’re not just saying, “Hey, the world is changing.” And then sometimes I’ll see, “The world is changing,” and there’ll be, “Used to be,” and there’s a long list of things and then, “Now it is,” a long list of bullet points.

What’s really, I think key is naming it, naming that old game. The examples you saw, software, cloud, transactions, subscription opinions, reality. This very, very concise naming is really key. And it’s hard because in making it compact you’re losing completeness. So you can imagine you’re in a meeting, someone says like, “Hey, how about we do transactions to subscriptions?” And someone says, “Well I don’t know, there’s a lot of things I don’t really subscribe to. Subscription economy, really?” So we’re always kind of overstating it in a way, but it’s not a problem. I don’t think people say like, “Oh that’s wrong, subscription economy, because I still go to the grocery store and buy things.” So anyway, that’s the first piece.

The second piece is what I call naming the stakes. And there’s a few ways to do this, but one that’s really great if we can do it is to name the winners to show that winners are already playing this new game. So for instance with Zuora they’re saying, “Hey, look, look at all the new winners,” this is like 2015 so, “Airbnb, Box,” all these companies, they’re already doing this subscription thing.

And by the way, overall they show this scary stat about the longevity of Fortune 500 companies. It’s getting smaller, and so it’s a little disingenuous, but basically they make this case that, “Hey, companies are dying, the ones that are winning are doing this.” And so to the extent we want to make this life and death just like a movie. This is again, I’ll make the parallel to Star Wars. So Luke, he spends the first 15 minutes of the movie belly aching. He wants to be a pilot, he wants to go out and have adventures in space. So Obiwan comes, he says, “Hey, we got this mission, this princess we got to go,” and all this stuff, “Let’s go. I’ll teach you to be a pilot. We’ll go have adventures in space.” What does Luke say? He says, “Ooh, you know what, I can’t really get involved. They got to go home. It’s late.” Who does this sound like? The reluctant buyer.

So yeah, “I want to be innovative and all this. Ooh, you know what? I don’t have budget this quarter.” So how does George Lucas change Luke’s mind? He basically kills the aunt and uncle, sorry, spoilers, it’s been 40 years though. If you haven’t seen it, you’re probably not going to see it. Kills the aunt and uncle. Now it’s pretty clear they’re coming for Luke. Now the stakes are life and death. Probably he’s going to be dead. But there is this other path that Obiwan holds out for him.

And whenever I work with teams and I talk about this, so they’re like, “Okay, I guess we got to then for kill the prospect’s aunt and uncle,” and basically yes, I mean figuratively. We got to show them that the future is not going to just be sort of okay. People talk about making it emotional and I’ve always wondered, what does that mean? Literally, what is the definition? This is for me the definition, is that the prospect doesn’t see the future as sort of okay. They see it as split between a very negative outcome and a potentially very positive outcome.

Andy Raskin: The third piece is what I call naming the object of the new game. I used to call it the promised land message, but I’ve changed it to this because I’ve found that it’s sort of a little more fruitful. This subscription economy, transactions, it can get a little highfalutin and sort of big, but on the website when we just have to boil it down to a couple of words that’s going to be clear right away, what can we say? And I find that what’s the object of the new game really boils it down as kind of the rallying cry of the movement. So the example with Zuora, the object for a while was turn customers into subscribers. Very simple. It just sort of flows from it. Airbnb for a while had this one, live anywhere. If you think about-

Lenny: Belong anywhere.

Andy Raskin: Well actually it was-

Lenny: Oh, live like a human.

Andy Raskin: So you’re right, it was, “Belong anywhere,” and then it switched to, “Live there.” I may have the chronology wrong, but it was the two of those things. You know better than I do. But either one, I mean think they’re saying very similar things. Hey, there’s this new world where you don’t have to live in hotels, you can stay in people’s houses. What’s the object of that game is to belong anywhere, but live there. And I love it when it works that way where it’s almost like an asymptotically unachievable thing. You are never literally going to live there. And if you think about it, this buyer mission statement, this rallying cry, I think of it really as the mission of the company. I mean, what is the mission of Airbnb other than to help people live there if they’re going to be customer focused and all that?

The fourth piece is, okay, well this object of the game, winning this game, it better be hard because if it’s not, why would we even exist? Just with the movie, if Luke can just go destroy the Death Star then no movie. So there’s got to be sort of obstacles in the way, things that are preventing them from. So saying, “Okay, you want to turn customers into subscribers.” So whereas Zuora, where they go next is to say, “Okay, well how are you going to measure lifetime value?” Because now you have this always on thing. “How are you going to measure preferences and how they’re changing over?” All these new kind of challenges that didn’t exist before. And then these are like the monsters in Lord of the Rings or the Empire in Star Wars, these are the obstacles.

I think about them because they sound like problems. This is what people would normally say, “Oh, these are the problems we solve.” But by setting up this story thing first we’ve repackaged them as obstacles to a new goal state that we’ve already positioned as life and death. So they take on this much more emotional meaning. We understand why they matter. And then of course the last piece is now talking about, well, how are we going to overcome these obstacles? Narrative people, in the movie business they call these the magic gifts that the main character gets to go help them win. What are the ways? Now we can talk about that and success stories and all the rest of the stuff.

Lenny: There’s some obvious parallels to the hero’s journey here. I imagine that it was a source of inspiration, and the Star Wars I think is the epitome of that journey. Can you talk about just how related those two are, how you think about that?

Andy Raskin: Yeah, I mean so hero’s journey is this book that comes from, I think it’s Hero of A Thousand Faces is a book by Joseph Campbell, a sociologist. He looks at myths over different cultures and different times and he finds this kind of common structure that he calls the hero’s journey. I mean it’s some controversy about that, about his book. Is it a very male oriented sort of take on things and a bunch of things.

But even that aside, I found when I would talk about hero’s journey and stuff, it’s just like, it didn’t really tell me what to do. Yeah, okay, yeah I got to do this pitch. So in the hero’s journey there’s like refusal of the call. That’s actually that thing where Luke says he doesn’t want to go and where the buyer says, “Hey, I don’t have budget.” But I don’t know, it was just too theoretical for me to really … when I use it, people seem to sort of glass over. So I just don’t really talk about that at all. But yeah, I mean that’s behind a lot of this stuff for sure.

Lenny: Yeah, that makes sense because I think if people hear about that all the time when they’re like, become a better storyteller, tell your story in this hero’s journey, and it’s like, “I don’t know what I’m doing.”

Andy Raskin: Also, I would say there’s storytelling as a skill kind of thing, which is a great thing. Learn how to tell stories better, blah, blah, blah, blah. I’m not really interested in that in my work, what I’m interested in is the one story and the structure of that one story. And this one story, it doesn’t really have … like, the world is moved from transactions to subscriptions. There’s not a main character in that story who’s like having a problem and getting saved. It’s almost as if what’s happening is we’re turning the person we talk to into the main character. By spelling out the shift, we’re changing their world and we’re saying, “Hey, you got to change and you want to come with us.”

Lenny: It’s almost like you’re putting them into the hero’s journey, like, “Here’s how you win.”

Andy Raskin: Exactly. I love that.

Lenny: Let me just try to summarize what you shared, this five step framework. So you start with here’s a new movement that’s happening and you want to name it, you want to name the stakes and there’s winners and losers and here’s already happening and it’s really important. Then you want to name the object of the new game, like turning customers into subscribers. Then show the obstacles, here’s why it’s challenging, and then talk about how you’re going to overcome these obstacles.

Andy Raskin: And by the way, the naming of the object of the new game, I find it often is really nice to do it as a question. So we hey, there’s this shift from transactions to subscriptions and look, everyone’s doing it. So we asked a simple question, what would it take to turn every customer into a subscriber? And this way we’re kind of bringing the person we’re pitching to almost like they’re coming along with us as a co, I don’t know, adventurer in crafting this story.

Lenny:

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Andy Raskin: Okay, great. So there’s a company called 360Learning. So this company, I don’t know if folks know, but this company is raised over $200 million. They’re in the space of corporate training software. So big companies, they have to train their people on all kinds of stuff. So you want to go through that one?

Lenny: Yeah, that sounds great.

Andy Raskin: Okay, great. By the way, Nick Hernandez is the CEO and Nick’s been on my podcast, so he’s talked about this. So they for a long time were pitching themselves as collaborative learning. So they have features that let people sort of collaborate on courses and all kinds of stuff. And Nick is often pitching CEOs, of course his team is as well. And he told me that it was sort of falling a little bit flat. People, collaborative learning, whatever. How are you different from this learning platform, this learning platform?

And so when we worked together this collaborative learning, it’s almost like a category name or a descriptor or something. They were so embedded that I decided, I don’t even want to take it out, but can we define it in terms of a story? So the story they came to was, hey, used to be that companies train their people through basically a mindset of top-down learning. There’s going to be some learning guru at the company, they’re going to get all the courses, they’re going to put it all together and sort of send out this training material to everybody.

What’s happening now is winning companies are approaching this differently. They’re adopting this approach we might call upskill from within, which is if you look at Google, there’s this page where I think you can go, it’s a public. You can connect with Google’s AI experts. They literally turn their internal experts into champions that are educating, not even just the company but even external people. They’ve created this culture of our own people are going to be the educators. So that’s the shift from top down to this upskill from within. And of course I just even started to do the second piece which was like, hey, look at the big companies who are doing this.

And then I think they showed, “Hey, you’re not doing this. Look, training is becoming very expensive. People don’t care. So this is the downside. So we’re creating these sort of stake …” And also I think he has something about how training now, like companies, if you don’t adapt, if you can’t get these skills to your people, if you’re a car company and you can’t get these skills around electric cars, you’re dead.

Nick was in France and he saw this poster, a recruiting poster from McDonald’s and it said, “Hey, if you work at McDonald’s you’re going to learn from everybody else on your team.” And it was like, wow, there it is. So there’s another example we used as a kind of winner example. And so then the question became, I can’t remember exactly, it was something like, how do you upskill from within? What would it take for you to turn your experts into champions of learning in the company and turn them into stars, and all this?

And then I’m going to forget here what all the obstacles were. But I think it was things like, well, how are you going to make it possible for anybody to create a course? People who might have expertise in electric engines but don’t know how to create a course, how are you going to make sure that there’s still the learning department, they’re going to keep control and can … all this. You can imagine all the different kind of questions. And then of course now 360Learning starts talking about all that stuff.

What Nick has told me, I’m actually going to be on a webinar with Nick where someone asked me, “Could you bring in a CEO who could talk about this stuff? Not just you B blabbing on about strategic narrative.” And so Nick is going to join it. And we had a dress rehearsal the other day and he was telling me it’s just like when he starts with this now he doesn’t even get the question anymore of well how are you different from this other learning platform? Which used to always be the thing. It’s just a much more seamless, okay, yeah, talk to our learning people, get this going. So it’s just sounds like it’s been really effective for them.

Lenny: That’s actually was what I was going to ask next is what kind of impact have you seen with someone shifting their pitch story from this doc? What was the arrogant doctor approach to the strategic narrative?

Andy Raskin: Yeah, I mean it’s always this kind of thing I hear. I mean, of course it’s very difficult to measure this. I mean, what was the value of the strategic narrative for Gong and its growth? Was it 3X versus 1X, 2X? Or I don’t, who knows, right? But the things I hear from CEOs, a few things. One is that when they’re pitching, they’re not pitching features out of context, they’re pitching now a movement which is a lot better place to be, I think. In a way you’re not pitching product. Product is like a prop for making the story come true. Very important prop, but there’s this higher level overlay that becomes the focus of the conversation, at first, and of course we’re going to get into product and that helps sell. Once we have this story then everything in marketing can be all about this story.

With Zuora, if you look at their website, well when they first started doing this, maybe 80% of the content is not, “Hey, let me tell you about how Zuora is so great,” or, “Here’s our new release,” or whatever. It’s, “Here’s how music companies are embracing subscriptions. Here’s how luxury goods companies are embracing subscriptions.” It’s all these kind of almost trend pieces that become unlimited fodder. And again, you’re not touting your … it’s less salesy, right?

Another thing I just hear always, I just interviewed a CEO this morning for my podcast and this is the first thing he actually said was, “It becomes the strategic north star for the product.” So what he was telling me, and this was actually a little unusual, I asked him, “Why did you come to me at first?” And of course I’d asked him that before, but he said something this time that was a little different from what I’d heard before. He said, “We are constantly getting feature requests through sales, through customer success. And we had sort of no way, bar to decide well what do we take on, what don’t we take on? And this clearly has become our bar.”

If you think about it for 360Learning, does it help us upskill from within? It’s in. Does it not? Or it’s prioritized. Does it not? Less prioritized. Amit Bendov told me this directly, he said we exactly the same thing. He said, “We get a lot of requests for features and a lot of them are basically about opinions, some way to record opinions.”

Lenny: And this is Gong.

Andy Raskin: “We’re not going to do those.” In Gong, yeah. “We’re not going to do those.”

Lenny: Are there any companies out there that maybe aren’t clients that you see as like, wow, these guys are nailing it and they’re doing a great job of this strategic narrative?

Andy Raskin: Well, one that really comes to mind is, I mean it’s been out there for a while, but Drift. Drift comes out with essentially like a chatbot for your website, which might be the 30th chatbot for your website. And they don’t say, “Hey, here’s why our chatbot is the best one.” They start from a completely different place, which is, “Hey, used to be people would sort of wait around for you to get back to them. It was a world of later. They called it the world of forms. You put up a web form and you expect someone’s going to fill it out and maybe wait a few days while you take your sweet time deciding if you’re going to get back to them.”

And David Cancel and David Gerhardt started from right the beginning saying, “Now we’re in a world of now, where buyers are …” I think they showed this woman, I remember it was this woman sleeping with her phone. That’s your prospect. They’re always on and they’re going to expect you to be engaging with them right away. And they called this conversational marketing, and they really went with that and created I think a whole movement and they broke away from all of the other chatbots.

Lenny: Awesome example. So earlier you threw out this word category, and I’ve noticed you haven’t talked about category and category creation too much, and I think that you’re kind of not a fan of this idea of creating a category and focusing on category. I’d love to hear your perspective on how that all relates to the stuff you recommend.

Andy Raskin: Lenny, are you trying to get me in trouble? Like that guy who guy on your podcast who attacked jobs to be done?

Lenny: Apparently, let’s do it. Let’s see what kind of trouble we can get into.

Andy Raskin: I would soften it a little bit and not just … because I don’t want the ire of the category design folks, but I really would soften and say, I wouldn’t say I’m not a fan of creating category. Look, I think if you look at Play Bigger, which has become The Bible of that category creation thing, if you look behind that going to, what do they say the category is? They say it’s a narrative. It’s a story about how the world was to how it is. And so what I find though is that when people think about category creation, they tend to just focus on, okay, well, what is this category name going to be that we got? What are these three words or two words, whatever, that are going to magically make us seem like we’re totally different from everybody else?

And A, I think that’s not really possible. These three words aren’t going to do it. Take Gong, I mean already other companies were using this term revenue intelligence. With Gong, it suddenly becomes a thing because I think they have this opinions-to-reality story behind it. At one point, again, I asked Amit, he said, “Yeah,” because I remember he really struggled, “What should we call it? What should we call it?”

He came up with that one. But then when I asked him later, he is like, “Yeah, you know what? In hindsight we probably could have called it strawberry intelligence. It didn’t matter. It was really the story that sort of mattered.” I think he was exaggerating a little bit. And I think the category people would actually agree with this, I think they would agree with, hey, these three words are, it’s sort of a shorthand for this movement of old game narrative.

But I guess I feel like still by calling it category and category name, we’re just focusing on those three words so much. And what happens often is CEOs will, they’ll kind of come up with this little category, like what happened with Nick at the 360Learning with collaborative learning. We have this name, but we don’t know how to tell the story around it. So my feeling is like, well, let’s focus on the story. So that’s why I talk about strategic narrative and movement creation versus category creation. If someone decides that your movement is a category, great. Bonus.

Lenny: I see. So essentially your approach is category can play a part of this, but there’s a bigger question you have of what’s the story, what’s the movement, what are the obstacles and categories and element of that potentially?

Andy Raskin: I mean, I almost see them as orthogonal, like with HubSpot. HubSpot had this narrative around inbound. It used to be just outbound stuff, now we’re going to have inbound. And that wasn’t really a category. Back then they were probably known as marketing automation. Now they’re probably known as CRM because they’ve broadened. But this movement is the thing that’s sort of the constant and in some ways orthogonal to whatever category they’re in.

Lenny: Is the strategic narrative framework right for essentially any company or is there a sweet spot? And I’ve noticed most of the companies you’ve been talking about are B2B SaaS. So I don’t know, maybe if there’s a spectrum of perfect fit for strategic narrative framework and then not a fit at all. What’s along that spectrum?

Andy Raskin: Yeah, well you can see, I mean it takes a little time to tell this story and you were kind of framing it a little bit and we’re telling it in lots of different channels. So I think it does really play well in this enterprise sales context because also we have a group buyer there. So it’s not just one person who’s doing some research. This whole group has to have a uniting story. So I think you’re right that in noticing that the companies that this tends to resonate with tend to be B2B, enterprise sales, technology I think because often the product is very complicated. That arrogant doctor stuff comes from an age when the things people were selling were products on shelves that didn’t change much, cans of soup at the supermarket or a car in a dealership. Even software back then, shrink-wrapped in a box, doesn’t change.

B2B software, this stuff is changing by the minute. And does it even make sense to make a claim to say, “Oh, we have these features and they have those features, therefore we’re better,” does that make any sense? That said, hey, I was looking for a sports watch, a Fitbit and I’m comparing specs and I’m doing all that stuff. And so that mode of buying is still happening, but I think, so yeah, when consumer products companies contact me, I usually say, “No.” Occasionally they still say, “Okay, yeah, we’ll build this, we still want to have this narrative.” But yeah, I think it has the most value, most impactful right away for B2B enterprise technology companies.

Lenny: Just a few more questions. One is just what’s a sign that you should spend time in this area, that something is broken in your strategic narrative story pitch?

Andy Raskin: Well, I can tell you what I hear from CEOs when they contact me. I always ask, what’s happening? Because that idea I had, no CEO’s going to budget a line item for this. I’m basically asking, why was I wrong? So a few things they tell me, one is that the company is maturing from a point a stage where they’ve been successful, but that success is … one CEO put it this way, was brute force of the founders. So the founders are in every meeting, they’re in every product discussion, every sales call, and that’s shifting, the company’s getting bigger.

Usually I’m seeing this around series B where the company is getting … so they can’t be in every sales call, every market call and they’re looking to transmit all the good stuff and some direction in a way that people are going to remember and all that. Everything from how we pitch to what the product should be and all that, and they see this as that.

Andy Raskin: There’s another point that I see people contacting me at, which is where they’re growing. It’s usually a bit later where they’ve scaled tremendously successfully. Now we’re either acquiring or building out whole new product units. And that old story we told is just, it’s just not big enough and we got to expand it to something bigger. This is the example of OneTrust, which the CEO I had on my podcast recently. Starts out with just, I think it’s data privacy around the regulations that people have to be able to say, “Don’t track me,” things like that. And then they buy these other company and now we have this much bigger offering. So how do we tell the story? And then I guess the third one is some form of pivot where hey, we were telling an old story but whatever, the market changed or whatever and we want to go in a different direction.

Lenny: Say a founders listening to this and they’re like, “Okay, I realize I need to do this. I haven’t spent enough time on this. Something’s not working. This could be a huge unlock for us.” What are the first couple steps they could take to start to figure this out? And I imagine at some point it’s like, go talk to Andy. He’ll help you through this. Is there stuff you can do on your own? How do you go about figuring this out?

Andy Raskin: Well, a lot of folks have emailed me over the years like, well I told you before, there were some who emailed me like, “Hey, tried it, didn’t work.” But many more have emailed me, “Hey, I tried it, it did work. Thank you.” And so yeah, just try to lay out that structure and try it mean even when I work with teams, I adapt what people might call sort of lean approach. I want to get that thing out there into sales calls. We’re not rolling it out to the whole sales team right away, but getting it out into some sales calls and get a sense, “Hey, is this resonating? Are people given the nods?”

Ideally by the way, one way I look to test it, is it working, is when we talk about this shift and the stakes and do they stick. Do they kind of say, “Yeah, let me tell you how that’s playing out for us,”? Or, “Am I? Yes, I’m seeing that.” Sometimes I’ll literally, I’ll train salespeople to ask them that question, like, “Am I crazy or are you seeing this?” And what do they say? And you can usually tell if they’re in and it’s qualitative. But I really like that kind of testing to see if it’s working. And I think anybody can do that.

Lenny: Is there a template or guide you have online for folks to follow other than maybe just listening to this podcast and reading? Is there a post that’s like, “Here’s the framework defined, and go follow these steps,”?

Andy Raskin: I mean, I guess the closest is that The Greatest Sales Deck I’ve Ever Seen post, which is the Zuora deck. But even there, people have asked me for a framework and presentation companies say, “Can we have your template so we could make it available to people? We’ll revenue share with you or something.” And I am so against this template. Every team I work with, it’s different. It’s not the same number of slides. Sometimes we can lay out this shift in one slide, sometimes it just feels better or the team likes it better, whatever, if it’s a few and we’re sort of getting people into it. Sometimes there’s no slides. So I am really hesitant to recommend any template. And what I’d say is these are principles for building it, not any prescribed formula.

Lenny: If they do want to reach out to you while we’re on this topic, what’s the best way to contact you?

Andy Raskin: Connect with me on LinkedIn. That’s usually a good one. And I’m usually posting things on LinkedIn that I’ve learned from working with other teams.

Lenny: Awesome. Last question before we get to a very exciting lightning round. Speaking of LinkedIn, you posted how in a working session with companies that the second session is always this low point they all go through and that everyone’s starting to get discouraged and pained. And first of all, I love the expectation setting. You’re like, “This is going to suck initially and it’ll get better.” Why is that the low point and what is it that they focus on in that second session?

Andy Raskin: Well, apparently I’m not doing enough of an expectation setting, because what that post was about was this woman. So when I work with a CEO I always ask them to create what I call a strategic narrative team of up to four people. And usually those are leads of marketing, sales, whatever. In this case, the CFO was a really important person in this company. And so the CEO wanted her as part of this team. And she said to me at the end, she’s like, “I love where we got to.” I always ask, “What worked? What didn’t work?” And she’s like, “I love where we got to. That worked great. What didn’t work was like, you told us that this second session was going to be bad, but I think you could have drilled home more like exactly how bad.”

And then I asked her, “Actually, could I have that quote with your face on a slide that I now present to future teams?” She said, “Yeah, you could do that.” So the way I work it is I have a kickoff session where essentially I’m asking people on the team, what are these pieces? What is this old game, new game shift? How do we talk about when to set the stakes and everything I just took you through? And we have like five people in the room. There’s going to be … we’re going to come out of this with notes and notes, boards and boards of ideas of this stuff.

And so then two things happen. One is I ask the team to start interviewing customers about how they see this shift and sometimes the customers will literally give us the words and that can be helpful in sort of aligning if we have differences. But I also start working with the CEO one-on-one and we build a first version of this thing, and it’s the second session where we present this first version to the team and think about what’s happening.

The team has just given us millions of gold ideas, truly they’re all … and in order to make something sort of clean and powerful, the CO and I have had to pretty much throw out all of them, save one or two. And there’s going to be feelings about that, first of all. Second of all, if this were easy to just get all … interview everybody, come up with it, they would’ve done it. So it’s going to be wrong.

But the good news is this is where the team gets to weigh in. I also ask, what’s working, not working in this thing? And when we learn how it’s not working, that gives us the juice to then me and the CEO go back to the drawing board. We plan on this in advance, we’re going to go back to the drawing board and then bring up something good. So having a shit draft is a million times more valuable than having all these great ideas. But it’s also really painful. It’s painful not only for them, but for me. No matter how many times I say this, I expect they’re going to love it in that first one too. And I’m really pissed off when they don’t. But luckily now I’ve done enough times I know that’s going to happen.

Lenny: I was just watching a documentary about Annie Lamont who came up with the first draft concept for writers that I stick to.

Andy Raskin: I’m a firm believer in that. Yeah.

Lenny: As you’re talking, one last thought that I had is, so you’d work with because and founders. I feel like this could be just as useful to product leaders, product managers working on a product that they’re launching, just like what is the movement, where it’s happening, here’s why this product’s important. Do you find that too?

Andy Raskin: Absolutely. And very frequently, the product leader, chief product officer is part of this group. What I’d say though is that the reason … so after I did this work for a few years, I looked back and I was like, which were the engagements I did where I can see it, and the narrative is really this true north star for everything?

It was always the ones where the CEO was leading it, not just in name, but literally the person who called me who was working on the drafts with me and going through. And so initially I didn’t insist that it would be the CEO doing that, but eventually I started to, and I think even for a product leader, you’re going to want the support. You don’t want to be just telling that story in product. You’re going to want that supported from this Zuora person who gave me the initial deck, he said it, “It was like I had air cover and I was just going down and knocking down deals on the ground.” You’re going to want that air cover in marketing, sales, recruiting, everything. And how much better is it if it’s really driven by the CEO and you have that?

Lenny: Amazing. Is there anything else you wanted to touch on or you want to share before we get to our very exciting lighting round?

Andy Raskin: No, except I love category design people and it’s really just sort of terms that I like that are … you know what? Forget it. Scratch that part.

Lenny: I thought that was funny.

Andy Raskin: Oh yeah. Okay. Yeah, we could leave it in. We could leave it in. You could even leave this in where I’m telling you to scratch it.

Lenny: Sounds good. I was actually going to joke that I was going to cut this out and leave you hanging, but okay.

Andy Raskin: No, you can do that. Yeah. Category design people. Love you. Don’t hate me. Thank you.

Lenny: Great. I love it. We’re going to be okay, I think. Well, with that, we’ve reached our very exciting lightning round. I’ve got five questions for you. Are you ready?

Andy Raskin: I’m ready. I saw like what you sent them, but I didn’t really look at them, so I’m just going to tell you what I said. I’ll go off that.

Lenny: Perfect. Excellent. The best version of this. What are two or three books that you’ve recommended most to other people?

Andy Raskin: One of the books that I read initially from that Barnes & Noble, it was Story by Robert McKee. I think a lot of people know about it who are sort of interested in story stuff, but it’s kind of a Bible of people who are doing screenwriting and stuff. If anyone who’s in Hollywood who thought about going to Hollywood, they know about this book. I love a book called Out of Sheer Rage. It’s really not about what I do or anything, but the author is Geoff Dyer. Geoff, he’s written a lot of books that are kind of essay memoir, and this is a book about him trying to write a book about DH Lawrence. So it’s all about procrastinating and like, “Oh, I’m supposed to write this book. I’m about to go on a trip somewhere. Should I bring the collected works of DH Lawrence with me on the trip because that’ll help me start the book, but maybe I shouldn’t because it’s not going to … Then I could come back refreshed without having …” Basically, it’s all that. It’s this sort of in the head. I just really enjoy that book.

Lenny: What’s a favorite recent movie or TV show that you really enjoyed?

Andy Raskin: Station 11. Station 11. That was just so beautiful to me.

Lenny: Trippy. That was a trippy movie. Did not expect to go where it went. I usually ask what’s a favorite interview question you like to ask, and I don’t know how often you’re interviewing people, but does anything come to mind when I ask that?

Andy Raskin: Well, I can tell you one thing I ask when I speak with CEOs is I like to ask, what role has this narrative played in your leadership? How does it work in your leadership? And it’s always really interesting for me to hear that, ‘cause I often hear things that I don’t expect.

Lenny: What’s a favorite product you’ve recently discovered that you just really like?

Andy Raskin: I recently got a Fitbit. I think I may have mentioned it earlier. I was looking for a product like that, and so far I’m really loving it.

Lenny: Amazing. Have you tried other versions of Fitbits or that’s the one that’s working?

Andy Raskin: I also ordered a Polar at the same time and wound up returning the Polar. Basically, it was just a little clunkier on my wrist, so I went with a Fitbit. Well, do you have one that you recommend instead?

Lenny: I just have the Apple Watch and I’ve never tried a Fitbit and it gives me all this stuff that seems cool, but I’ve never gone further.

Andy Raskin: I got the Fitbit like a week ago and I actually still am on the fence whether I bring it back to return it for the Apple Watch, so I’m enjoying it, but we’ll see.

Lenny: Okay. Final question. You’re expert on presentations and I imagine you spend a lot of time in decks, and so just what’s like one small change people can make to how they put together a deck or a presentation that will make their presentation a lot better?

Andy Raskin: This is the one thing, make the title the takeaway of the slide so that the person looking at it has to do zero work to take away. So example, you’ll sometimes see, “The problem,” or, “The team.” Replace, “The team,” with, “Our team is veterans of whatever industry,” or every single slide it’s a takeaway, not a label. It’ll make everything flow a lot better.

Lenny: You did a killer job answering the lightning round questions without having a peek at what they were going to be. Andy, this was incredibly insightful. I’m going to go start working on my strategic narrative for my podcast and newsletter. Two final questions. Where can folks find you online if they want to reach out, learn more, maybe consider working with you? And then how can listeners be useful to you?

Andy Raskin: So I mentioned LinkedIn as a way to connect with me. That’s fine. My website is AndyRaskin.com. I also have a podcast where I talk with CEOs, so if you’re interested in hearing more details about actual use of this, it’s called The Bigger Narrative. My mom introduces every episode. I sent her the interviews in advance. I call her and interview about what she thinks people will get out of it, and that conversation becomes the intro to the podcast episode. And what was the last question?

Lenny: How can listeners be useful to you?

Andy Raskin: Useful to me. Just if you try any of this stuff, let me know. Like, “Hey, worked. Didn’t work. Have this question.” I would love to hear that stuff.

Lenny: Amazing. Andy, thank you again for being here.

Andy Raskin: Thanks so much for having me, Lenny. This is really fun.

Lenny: Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at LennysPodcast.com. See you in the next episode.

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