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Bob Moesta on unleashing your sales superpower

In our latest episode we chat to the founder, maker, innovator, and professor who helped pioneer the Jobs-to-be-Done framework and has now turned his attention to demand-side sales and making it an empowering experience for all.

This week’s guest is no stranger to this podcast in fact, today’s episode will be his third time appearing as a profiled guest with us. Bob is the President & CEO of The Re-Wired Group and serves as a Fellow at the Clayton Christensen Institute. As a visual thinker, teacher, and creator, Moesta has worked on and helped launch more than 3,500 new products, services, and businesses across nearly every industry. Our previous conversations with Bob have covered how to unpack customer motivations and the Jobs-To-Be-Done framework (of which he was one of the principal architects).

In this episode, Bob and I chat about his new book Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress. We talk about his reasons for writing a book on this topic, his friendship with the late Clay Christensen, and get some further insight on his career so far. If you’re short on time, here’s some quick takeaways:

If you enjoy our discussion, check out more episodes of our podcast. You can subscribe on iTunes, stream on Spotify or grab the RSS feed in your player of choice. What follows is a lightly edited transcript of the episode.


From patriot to Pokemon

Des Traynor: Today, I’m thrilled to be joined for a record third time by Mr. Bob Moesta, who our regular listeners will be well familiar with, Bob is one of the grand creators of the Jobs-To-Be-Done framework that we’ve talked about so many times on this show. Intercom has also worked with Bob’s agency, The Re-Wired Group. We’ve all followed his writing since the start and he is a true business framework guru, and he’s also an inspiring character personally to me and has taught me so much.

He’s also the author of a very, very, very recently released book, which is Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress. We’ll be talking a little bit about how Jobs-To-Be-Done and sales go together. We think this will be a lot of interest to our listeners, because we don’t talk about sales enough. I think Bob has got some of the sharpest and crispest thinking for folks who might be sales curious, but not necessarily a sales rep just yet. Welcome to the show, Bob. It’s a pleasure to have you back.

Bob Moesta: Thanks man. Just happy to be back and love to chat about all this stuff.

Des: Awesome. Let’s just start with a very brief background. I know plenty about you, but you’ve had quite a varied career. Where did it start and where are you today?

“The way I’ve been explaining to people is that I’ve been breaking things for probably 50 years. I’ve been fixing things for 45 years, and I’ve been building things for 30 years”

Bob: The way I’ve been explaining to people is that I’ve been breaking things for probably 50 years. I’ve been fixing things for 45 years, and I’ve been building things for 30 years. For me, I’ve always wanted to build and have been building. To be honest, when I was very young, I was a little too creative if you will, and I had a few closed head brain injuries that prevented me from reading and writing. Out of that,I was forced to actually talk to people and learn through very different methods and tools. From that I’ve not only worked on over 3,500 different products, but I’ve been building methods and tools and things to help bring products and services to markets.

To answer your question about where I am today? Right now, I teach mostly. I teach at Northwestern and then I guest lecture at Harvard, MIT and I was Emory and Columbia and some others. At the same time, I also have a small agency where we actually work on products with people

Des: 3,500 products! I have to drill in here. That feels like a different product every day. I’m sure you’re guessing of all the things I’m curious about now.  How the hell do you keep track? Are these all software? Hardware? What are all these other products?

Bob: It’s a great question and not many people have ever probed into it. But I actually started at Ford Motor Company. For me a product was any one of the components that could go into building a system. Part of it might be bearings, and then we’d work on rear view mirrors and then I’d go work on pistons and then cooling systems and then suspension. To me, I consider all those to be different products.

Des: They’re a product in the sense that they have an actual job to do, right? You need your indicator to do a certain thing, so it has its own success criteria. Okay, that makes sense.

“I’ve worked on the guidance system for the Patriot Missile and radar absorbing material for the stealth bomber. Then I worked on “Pokemon: Mac and Cheese” for Kraft”

Bob: When I was part of the new product team, we would not only design things we also worked with suppliers and would fly all over the world to actually get those lines up and running and do that kind of stuff. At any one week I might work on four or five products and it would be one of those things, where I was taught some methods by Dr. Genichi Taguchi about design of experiments and how to prototype. A lot of my work was that the team would get the basics down and then we’d come in and do this set of tests, or set of prototypes that would then actually help us improve performance, and cut costs simultaneously. So really a lot of the products of that 3,500 that I worked on – were during the seven years when I was at Ford.

Des: The thing that might surprise most of our listeners is how generalizable some of your methods or approaches, or principles are. Am I right saying, you’ve worked on everything from the Patriot Missile, all the way true to an email client, right?

Bob: That’s right. I’ve worked on the guidance system for the Patriot Missile and radar absorbing material for the stealth bomber. I’ve worked on the space shuttle – main engine and the solid rocket boosters. Then I worked on “Pokemon: Mac and Cheese” for Kraft. I’ve worked on email clients. Part of it is this notion of thinking that because I can’t read, I have to put everything back to first principles. So for example when thinking about a conversation and the way that we listen to the words. So if someone were to say, “Well, we need trust to make this happen.”

I’ll think, “Okay, is trust an input to this system or is it really an output of the system? They’re like, “What are you talking about?” I’m like, “Well, as we’re doing this event, having trust come in becomes something you have to screen for. But if I have to build trust, then I have to actually have mechanisms in there to build trust.” This whole aspect of seeing things so generally but then basically seeing how they work over time is the secret sauce, if you will.

Where are the sales professors?

Des: That makes a lot of sense. One question – to get us closer to today’s topic – is that a large part of product design is seeing opportunities, or seeing the unmet needs of the customer or where that white space where people aren’t talking is? I think when I heard you were working on a book that was about sales, it really resonated with me straight away. Because I think it’s an area that’s lacking in literature. There’s so much inside knowledge on sales, and when I go and talk to our sales team, I learn so much about how to navigate accounts, how they make deals happen, et cetera, how they set traps, set up  and manage expectations, how to defend, how do you go on the offensive There’s so much there, but they’re often not the type of people who are going to publish heaps of blog posts about how they do it.

So when you told me that you were working on this book, I was like, “This is what’s needed. Someone needs to actually unpack this a little bit and explain some things here.” But I’m curious as to what happened to inspire that journey since we last spoke, I think it was like four years ago. How did you end up coming to the decision to co-author a book with Greg?

“What was it about sales that made it so unique that we weren’t even willing to teach at business school? While at the same time, the fact this is that every startup and every, almost every company struggles with sales in one way or another?”

Bob: This is one of those things where to be honest, I go back to Clay’s office. I was lucky enough to have four hours a quarter with Clay for almost 27 years. One of the things we always came back to (especially me having done seven startups) was that the hardest thing about starting a business is sales. It’s just one of those things. Then I turned to Clay and looked at him and said, “Why aren’t there sales professors?” He just looked at me like, “That’s a really good question.” I’m like, “Wait a second.” You start to dig into, you pull that thread and you start to realize there’s very, very few sales professors, especially like 10 years ago, there were virtually none.

What was it about sales that made it so unique that we weren’t even willing to teach at business school? While at the same time, the fact this is that every startup and every, almost every company struggles with sales in one way or another? Part of it was to dig into that realm. I think the other part was, if I reflect on my experience, sales was always the hardest thing for me. At some point, it didn’t become sales anymore. I had to go back and almost, sit on the couch and think back to like, when did it stop hurting? When did it stop feeling so icky? That’s where we come back to Clay, who I think said it best, that one of the reasons why they don’t teach it is because there’s no theory behind. It’s all practice.

It’s all techniques. It’s all specific to your product and to your world. A lot of times people would say, “It’s a trade. Sales is a trade. There’s no theory behind it,” and so I said, “Well, what if we actually took the JTBD theory and flipped it and said, well, let’s understand how people buy, and then basically used that as the foundation and then come back and say, “All right, how do we set up our sales approach to help people buy as opposed to sell our product?” Once you started to get into that pool of knowledge, you started to realize, there was a lot more art than science for sure.

“This idea of sales as a trade, I think that resonates with I hear people speaking about sales. However, obviously buying isn’t. Your customers don’t go on courses on how to buy”

Des: An interesting point you had there was idea of sales as a trade, I think that resonates with I hear people speaking about sales. However, obviously buying isn’t. Your customers don’t go on courses on how to buy. The approach for customers is almost always the same. They have some idea of what they want out of a purchase, and in a sense sales is a bridge between them and the value that they hope to get.

Bob: Right.

Des: Early in the book you propose this idea of “demand side sales” and “supply side sales.” Could you talk about what the differences are there?

Shifting your focus

Bob: I would say that I grew up and I was trained on the supply side, right? Supply side is this whole notion of, build a product and they will come. I can’t have demand without the product, and that everything I would define would be from the product side or from the supply side of the world. If I’m building mattresses, it’d be like, “Well, who needs a mattress?” Then we’d look over the wall and we’d see people in market segments and we’d see personas, and we’d see all this stuff. But at some point in time, we’d never go granularly enough to understand, what causes somebody to say, “Today’s the date to buy a mattress?”

What happens is that even though we want to be customer focused, we still actually have the lens or the reference points that we use to define everything and it’s through the product”

What happens is that even though we want to be customer focused, we still actually have the lens or the reference points, or the kernel that we use to define everything and it’s through the product. What you start to realize is that, when we do that, we actually have a bias, and that bias then forces us to think about how to be more efficient. But when you flip to the demand side and you just say, “What causes somebody to say, today’s the day they buy a mattress?” You start to realize, “Well, first of all, it’s not just a mattress. It’s about sleep.” They don’t worry about the mattress.

They say, “How do I sleep better?” The things that they use to sleep better are everything from a noise machine to ZZZQuil, to scotch, to working out, to a new mattress. You start to see that the competitive set is completely different. The industries that I compete with are actually completely different. You start to realize things like, “How do I actually help people make progress?” You start to realize that being in the mattress business, I might have to be at some other businesses as well. There’s almost two different worlds colliding. 

People keep talking about product market fit. When you go deep into that world, you start to realize there’s actually very little fit in a lot of cases. Despite that, we always are making trade-offs. To me it felt very product-ish and as if we’re saying, “How do we actually help customers make those trade-offs, as opposed to design the ideal product experience, which to be honest doesn’t exist?”

“I wonder, is there an element to what you’re describing that is about building a brand that bypasses the complexity of the sale?”

Des: I’m going to skip to later in the book, because there’s a question I want to ask that touches on this. You talk about the three energies in a purchase, right? Social, emotional and functional. When you mentioned mattresses just there, it reminded me of Casper. What I noticed about my friends who have Casper is that their purchase looks very different than it would if they went into an actual mattress store. If they go into a mattress store, it’s a combination of price plus brand and maybe salesperson. All the weird shit that people do; spring count, how many layers? Is it memory foam? All that sort of stuff. And they consume all of this information.

A lot of it might be psychosomatic or pseudobabble. They drink it all in and then, I’m convinced at least, half of it is there to let them think that they made a considered purchase regardless of whether or not they did. What Casper has done I think, is bypass that and said, “We are a brand that’s all about better sleep.” That’s all they try and do. That’s why they’ve gone from mattresses to pillowcases to nightlights. I’m sure they’ll probably do air purifiers and all sorts of stuff like that down the line.

But what’s interesting is what happens then on the demand side, with the customers. It’s like, in the same way people make one choice about Apple and next thing you know they just buy Apple. If that’s you then don’t have to think about what headphones you buy, you just buy Apple or whatever your brand is. I wonder, is there an element to what you’re describing that is building a brand that bypasses the complexity of the sale? Basically you’re saying, ‘Don’t worry. We got you. We’re the only people who think about this?” 

Ask the right questions

Bob: Yes. I think that’s what Apple does in a lot of cases. They understand the struggling moments that people have throughout the process. Think about walking in, there’s 40 mattresses, there’s one or two other people in the store. You actually haven’t bought a mattress in 10 or 15 years. You don’t even know any of the language behind it. There’s so much anxiety wrapped around it and you’re like, “Okay, I don’t know how to make this decision and I don’t know how to make it without feeling, touching, whatever.” Then you start to realize like, “Okay, I still don’t know what I’m doing.

What Casper did is they actually asked you very meaningful questions. For example, they didn’t ask if you were hot? They’d posed the question as, “Do you stick your leg out at night?” It’s a very different question and it makes people think, “Wait, how do you know that’s what I do?” That makes people realize that you were paying attention and it’s something very subtle.

To me, it’s these things that actually help people realize you understand their problem, and then if you do that and you can start to use language to talk about the outcome that they want, now you actually build their trust. Before this approach we tended to explain  instead of building trust. We ended up trying to explain what a mattress is, what are springs? What is an inter-coil spring? How does a hybrid mattress with foam and springs fit? 

“The reality is, the company is trying to educate us about their world and their product and I really don’t want to know. I don’t. I just want to sleep”

Des: No one cares. 

Bob: It’s trying to be the reason. It’s the old “feature and benefit” language. But the reality is, the company is trying to educate us about their world and their product and I really don’t want to know. I don’t. I just want to sleep. The other half of the problem is, being able to buy a new mattress when your partner doesn’t think there’s anything wrong with the bed. You’re like, “Wait a second. I can’t sleep at night.” You start to realize the true competitor is the BarcaLounger. It’s in the lounge. It’s someone saying, “Well, I’m going to sleep on the couch.” Like, “Wait, what?” You start to realize there’s certain things that go on, so being able to understand what are the things that lead up to saying, “Today’s the day I need a new mattress,” and then what are those things you’re hoping for as a result?

Not ideally, but what does progress look like? What most people don’t realize is, the new mattress just has to be better than the old mattress. The notion of having it shipped and literally being able to help people get rid of the old one and then putting a new mattress sounds amazing compared to the old mattress, and also they need 40 to choose from. They need to know that you’ve listened and that here’s your recommendation. To be honest, you sleep better.

Des: I like the point you made about, like a classic approach, maybe not classic, but a bad approach to selling a mattress would be to ask the buyer, “Hey, what do you want out of a mattress?” They’d say, “Oh, I don’t know.” The whole conversation gets derailed because once the salesperson does that, the buyer feels that they’re now set in a trap where no matter what, it just so happens that the product has it. Whereas a much more domain specific question like, do you stick your leg out or whatever, is so much more insightful and incisive. It cuts right to, “Oh, so you actually are an expert. I got it.” But it’s a question that is also, it’s not an expert in the sense of, “Do you want 75 or 80 springs per square inch?” Or whatever, because most people don’t know the answer. It’s a real, relatable and simple way to say, “We’re speaking your language.”

Bob: The crazy part is, there’s only really three different jobs A mattress gets hired for. One is, “I’m getting a new bedroom set” another might be “Oh I used to have a queen size and now I need a king, so of course I need a new mattress.” But the mattress is like the mayonnaise on the sandwich. It’s not the main thing. The other one is, “Look I’ve got to buy a mattress for somebody else. My mother-in-law’s coming to visit.” Or, “My kid finally needs a mattress.” It’s for somebody else and it’s like, “Okay, it’s got to be just good enough that they don’t complain.” Then there’s the one for me, and the one for me is very different from those other two. What happens is they merge all that crap together, and so you end up not being able to understand it. So if I can’t sleep and I need a new mattress, I’m willing to actually learn about it because it’s a big deal for me.

Understanding the struggling moments

Des: Right, you’ll invest the time. Talk to me about this idea of the “struggling moment” on your framework?

Bob: The interesting part to me is that to me, all innovations have to revolve around a struggling moment, and that a struggling moment actually exists irrelevant of supply. The way that we’ve been taught in academia, is that supply and demand are connected in price as a function of supply and demand. But the fact is Paul LeBlanc who started Southern New Hampshire, he’s the President of Southern Hampshire University, has grown it from basically about a 25, 2,800 students to 200, almost 200,000 students by literally understanding how people want to go back to school or back to college and get a degree, but can’t, and what he can actually do to make it easier for them?

This whole notion of the demand is that it’s been there for years, but nobody’s been able to tap into it because they wanted to serve it in a different way”

This whole notion of the demand is that it’s been there for years, but nobody’s been able to tap into it, because they wanted to serve it in a different way. My thing is there’s way more than 200,000 students wanting to do that, but the reality is, being able to see where the demand is, is where the struggling moment is? Most people don’t talk about it. Think about how many people want to take a picture, but couldn’t? They didn’t talk about the camera side, they didn’t say, “Well, what’s the shutter speed? What’s focal length? What’s the…

Des: …Aperture, all that.”

Bob: They’re like, “No, I just want to get a clear picture of my kid playing soccer.” It’s all of those things, where they’re struggling moments that are out there and people aren’t paying attention to them, because they’re looking at the world through their product.

Des: That is like in the case of a typical university, trying to reach this market, they’re like, “Well, they need to come here on campus for 40 hours a week.” It’s almost like every product has baked into it a set of assumptions. That’s what makes it a good fit for the people who currently use it. But it’s also the things that make it a good fit for some people, make it a bad fit for other people, and as a result it’s really tricky. It would be hard for MIT to pivot, to serve all these new customers, because they’ve probably built a brand, a campus, everything centered around a set of assumptions that might not be true.

“How many people want to make progress with something, but can’t because of access or knowledge or just inability to be able to do it? You start to realize, there’s moments that you struggle with a lot of things and just accept it”

Similarly for Canon or whoever else makes high-quality cameras; they’re probably making a few different assumptions. One of which is you’re willing to spend a couple of grand. Another one is, you’re going to carry around more than one lens and all this sort of stuff. When something like, say iPhone portrait mode comes out, it’s a hard one for them to accept, because the purists will say, “That’s nowhere near as good quality as what we do,” but the users of the iPhone portrait mode will be like, “Of all the things available to me, this is the best.”

Bob: That’s right. You have a little girl, you know when you’re running around crazy, you’re not going to stop everything and say, “Okay, hold on a sec. Let me get the camera out.”

Des: It just wouldn’t happen.

Bob: The thing is, you’ve got to look for something called “non-consumption.” How many people want to make progress with something, but can’t because of access or knowledge or just inability to be able to do it? You start to realize, there’s moments that you struggle with a lot of things and we just accept it. It would’ve been great to have a picture of that, but the fact is paying attention to where those struggling moments are, they’re the seed for all innovation. They’re actually the seed for why people buy something new. If I’m happy with something and it works and I run out of it, I’m just going to buy more. But if it’s not working, that’s when I decided to say something like, “Okay, I got to do something about it.” Real growth comes from addressing these struggling moments.

Shifting focus to the competitor

Des: What is a good way for an individual to harness this? Let’s say you’re listening to this podcast and you want to start a startup, how would you scan your own life for struggling moments?

Bob: Right. Part of this is, is being able to not only identify and to articulate your struggling moment but also being able to realize, who else struggles with it and what else do people do to try to solve it? A lot of times when we’re talking about new technology or we’re talking about new business, it’s like, “Okay, what are people going to hire once your product is there, and let’s go interview why people hired that product because that’s the place in which it starts.”

Can we actually identify and frame the struggling moments around my competition? What is your competition doing? Then from there as people actually start buying your product, to stay very current on what are those underlying causal mechanisms that make today the day they’re buying the product. The other thing to me is that interest doesn’t actually articulate progress. Just because they’re interested, they have to actually put energy, the social, emotional, and functional energy in to do it. When you give away things for free, it doesn’t actually help because you think people are using it, but they’re not.

Basecamp did that a great thing where they basically said, “We’re going to create Basecamp Personal. You get one project and you can use it as long as you want.” The whole aspect here is like, now people invest to plan their wedding or plan out buying a house or planning a trip. But the reality is, as they start to use it, they realize how it would be useful in their business.

“How do you tap into that functional energy there? Because clearly no one sits down in front of Microsoft Excel to do up a wedding plan, thinking they’re using the right tool for the job”

Des: When you mentioned looking at competitors, in the case of them hiring Basecamp for a wedding, the things that got fired might have been shared Google docs, shared Excel sheets or some junk like that. Some non purpose-built tools that happen to be hackable to make work for this. How do you tap into that functional energy there? Because clearly no one sits down in front of Microsoft Excel to do up a wedding plan, thinking they’re using the right tool for the job. But I think what they are thinking is whatever it is I need to do, I know how to hack this product into doing it for me.

Bob: That’s right. One of the areas I’m working on right now is vacations. How do you do vacations? The first thing you start to realize is, more than 70% of the people literally just bolt a vacation on to somebody else’s planned vacation. There’s only 30% of the people who really plan a vacation, and everyone else just goes along for the ride. But the real thing is those planners, the thing is how do they decide where to go and why are they going? You start to realize that most sites start with, “Where do you want to go?” The real question is, “Why do you want to go? What are you trying to accomplish?” And most people say, “Well, that’s obvious.” I can guarantee from digging in deep, it’s not obvious.

Sometimes it’s about reconnecting. Sometimes it’s about talking about the future. Sometimes it’s about relaxing, but your definition of relaxing and my definition of relaxing are completely different. You start to realize by understanding that. People can hack parts of it and it’s for coordination, right? You’re coming, I’m coming, here we’ll buy the tickets. It’s part of the information, but the real stuff gets down to when you start to actually figure out how you’re going to sequence things in the trade-offs that are there. At some point in time, you either end up doing things for other people, or doing things because you want to do it and just other people come along. Part of this is people can hack it for a period, but I believe that most people don’t go on vacations because they have a hard time figuring out how to actually figure out and align everybody on why they’re going.

Des: I 100% agree. I actually have a lot of energy in this place, because I’m probably the one idiot of my friends, who actually tries to corral everyone onto the same plan. It’s because I work in software. If ever I’m not working at Intercom, my next project is definitely going to be a group holiday planning app where multiple people log in, it’s got calendars, it’s got a Google Maps where you can add location, suggest locations. It’s like, everyone’s flight itineraries are there. We can have a shareable map on our phones, where you can see where everyone else is staying. The solution is so clear in my head. But what’s interesting to me is, I don’t know if I could get anyone else to use that, because they seem to be happy enough just to check their messenger or WhatsApp or whatever and see what’s going on.

My thing is, what people say, and what they mean are completely different”

Bob: Here’s the thing, it’s a very small group, but that small group has huge influence, right? Because you’re doing it, everybody else is happy not to have to. My belief is, this is where you take the Loop-In feature like in Basecamp and you just loop people into it, but you still have complete control. The anxiety moments are like, “Okay, I bought my tickets. Did you buy your tickets? But there’s very clear moments where people will basically say they’re in or out, and it’s the last thing you want to do to somebody who said they’re in all the way along, and you divide everything by 12 and now they’re out. But maybe they really didn’t want to come, but they didn’t know how to say no. 

It’s like all that anxiety, how do you actually help make that more acceptable as opposed to the peer pressure, that social pressure? There’s a lot of struggling moments around it that are just wonderful to dive into. I would love to be part of that and I have many, many vacation interviews, because that’s the training case study we’re doing as we start to build out our training stuff is around vacations, because it’s just so horrible.

Unpacking the language

Des: We’re going to get more grounded in software now. Let’s say sticking with this hypothetical desert island group holiday travel app, so as not to break any NDAs you’re under. The thing you taught me for the longest time through all the interviews we did together to talking Intercom customers was, I would accept an answer like, “Yeah, that sounds pretty cool.” You would immediately say, “Stop.” I’m like, “what’s wrong.” The dude said, “It sounded cool, Bob, why are you angry?” What is your thing where it’s cool and easy and smooth enough?

Bob: My thing is, what people say, and what they mean are completely different. And so, you start to realize that people add things in there, or they add words like, “Oh, that’s cool.” It’s like, “Well, what does that mean?” Like cool in the context of, “I want to follow,” or cool in the context of, “I want to be the first adopter.” Cool has at least 20 different definitions. And so, you start to realize we talk in this way that it seems very specific, but it’s actually still very abstract.

So I’m doing an interview around vacations a couple of weeks ago and somebody goes like, “Well, we went to Thailand.” “And when did you go?” “We went in October  because it was the cheapest time to go.” I’m like, “Oh,” and to let it lie a little bit and I come back with, “You said it was the cheapest time to go. How did you know?” “Well, somebody said,” I’m like, “Well, how much did you pay for it?” Because they didn’t know and it turned out they didn’t have a budget.

“You start to realize as much as people say they budget, that it’s back of napkin budgeting, as opposed to spreadsheet budgeting”

And so, they gave the impression that they were frugal about this decision. And that’s almost like the lie they told themselves to say, “We’re going to go here because it’s this,” but at some point in time, they had actually no idea whether it was cheaper or not. They had no idea of how much they even spent. And so you start to realize as much as people say they budget, that it’s back of napkin budgeting, as opposed to spreadsheet budgeting.

So you can build the spreadsheet, but at some point in time now what happens? You actually start to suck the life out of it, because now you’re worried about every dollar of where we’re going and what we’re doing. And it’s like, no, let’s just go have fun. And so, there’s a difference between pooling the money and what you just realize is people pool money more than they actually make decisions about exactly where to spend the money.

Des: And more generally, there’s a difference between words like “cheap”, because they don’t articulate what that actually means to them. Is it “cheap” just under a certain threshold or is like the lowest available thing or did they factor in quality at all? I know the thing we used to get caught with six or seven years ago was, we’d ask questions like, “Would you use this feature?” And we should have been suspicious of the answer because 100% of the features, 100% of the time the answer was, yes. And it was almost always followed with, “Yeah, it seems cool.”

You have a whole chapter in the appendix on this, but you talk about unpacking words like; easy, fast, convenient, healthy, smooth, quick, handy. All of which we see a lot, “Oh, yeah. That’d be handy.” And I think it’s probably when you’re trying to identify the root of someone’s frustration or they’re struggling and you’re trying to validate your own idea by showing it to them. Even if they’re way deep in their own struggling moment, you still need to look for a much more specific declaration of intent than, “Sure, it sounds fun or whatever.”

“When you think about marketing research, the fact is they just need to know that it’s handy, or they need to know that it’s fun or that it’s easy, that those words resonate. But as a product person and, or a sales person, I actually need to think how do I make it handy? What does handy mean?”

Bob: The key is intent. What’s the intent behind it? And so, for example, and it’s not only listening to what people say, but how they say it because in the transcript, I can say like, “Erm, it was good?” Versus, “It was good.” And then it almost says the same thing in the transcript, but the first one you have to go like, “All right, what was wrong?” You can see by the pause and the going down.

And so, this whole aspect of being able to understand and see the human side of this is really, really important because their intent is actually easier to see than their words. We were focusing on their words and it’s not the words it’s their intent. And so, I think that’s part of it. I think the other part is marketing. Most of this comes from what we would call marketing research, right And when you think about marketing research, the fact is just, they need to know that it’s handy, or they need to know that it’s fun or that it’s easy, that those words resonate. But as a product person and, or a sales person, I actually need to think how do I make it handy? What does handy mean? What has to be there for them to say handy? That’s different information.

“You start to realize – trying to take market research and put it into the gas engine is different than trying to take and put it into a rocket engine and it doesn’t work”

And so you start to realize, trying to take market research and put it into the gas engine is different than trying to take and put it into a rocket engine and it doesn’t work. And so, this is where I use this word unpacking. Alot of the research techniques we talked about are more centered in criminal and intelligence interrogation to get back to what the intent was and what the timeline is, what the causality is, as opposed to trying to get to the phrases that resonate with everybody.

Embracing the sales organization

Des: Here’s a question I’d love your take on, why are startups, for lack of a better word, allergic to bringing a sales motion into their business? I’ll give you the straw-man cases, something like this, people look up to and admire businesses that have no salespeople at all. For example, let’s say Basecamp, right? Basecamp do not have a single accounts development representative or account executive. And as a result, people might infer, Basecamp don’t do sales, therefore, we don’t need sales, therefore, let’s not do sales. You’re not making that argument in your book.

Bob: No.

Des: I’d love to hear, where do you net out? At Intercom, we probably have over 100 people employed whose job is to sell and we follow the idea espoused in your book of, dare not to convince, but to enable and aid and inform a purchase is really what we think of it as. But when you think about this spectrum of, “We don’t have anything to do with sales, it’s not a part of the day at all.” to “You can’t even see the software until you’ve signed a contract.” How do you think about that framework? What’s going on there?

Bob: I think there’s a couple of things. One is, when people refer to sales as the necessary evil, it’s like, then you don’t really actually understand sales.

Des: Correct.

Bob: Right? And Jason actually wrote the foreword to the book, right? And in the forward, he talks about how he sold shoes when he was 15. And he knew everything about how tennis shoes were made, because he was a sneaker head and he realized nobody cares. They’re in there because they’re a waitress and they want to be able to wait or they want to make sure their feet don’t hurt at the end of the day. They didn’t care about any of the materials or any of that kind of stuff. And he realized, “I run a software company where we have no sales or do we?” And then we talk about like, why do people buy? And by understanding how people buy, he’s able to be in the right place. He’s able to say the right things at the right time. The marketing is way more efficient that he doesn’t actually have to do it. He knows the dominoes that have to fall on people’s lives to say, “Today is the day that I need to be in Basecamp, right?

“They realize that there are people there who just aren’t technologically competent to put the system in or use the system. And so, they’re looking for the easiest thing, the easiest, smallest step that puts it in”

So one of them is classic of – we have a business we’re starting to grow. We have a few things start falling through the cracks and now we get more business. And now we don’t know, actually, we’ve got to get tighter if we’re really going to grow. And so, the way that the consumer we’re talking about is like, the wheels are coming off the wagon and it’s that panic point of, “We’ve got to get a system”And as they start to look, the thing is, is that they realize that there are people there who just aren’t competent, aren’t technologically competent to put the system in or use the system. And so, they’re looking for the easiest thing, the easiest, smallest step that puts it in. And so, that’s what they talked about and that’s how there are landing pages. So they’ve been able to help the customer discover their way to them, as opposed to having somebody who has to be on the phone dialling up.

At the same time though, the way you guys sell is very similar. Like at Autobooks and they sell to banks. And the whole thing is, when they first started, it was like, “Well, we got to get people to the demo. And once it gets to the demo, we’re going to close, right? And it’s demo and close.” And the thing that we actually helped them try to unpack was, where are they in their buying timeline And they’d say, “Well, that’s where they are in our sales pipeline.” I’m like, “No, no, no. Where are they? Are they in passive looking? Are they learning about it? Are they actually in the design part of it and like, what’s the difference?” And we start to realize one of their problems is that they have one demo that does three different zones with the timeline.

And when we look at a card, we were able to actually almost double the number of conversions and at the same time, have the time to close, because we were able to help people move down the timeline as opposed to be in our sales process. And so, one of those things where, by focusing on our process, we try to make the demo efficient, but we actually never realized that we probably needed three different demos.

That’s a very common thing where people come at sales from a marketing perspective and they don’t actually think about buying, they just think about attracting – getting people in the door as opposed to helping people make progress”

Des: Got you. We wrestle with this a bit internally and certainly the startups that I have either advised, or even just had Skype calls with were so much of the thinking of a startup that began without sales and then tried to add sales missed so many things along the way in doing so. I don’t mean to be dismissive of them, we were probably the same, but for sure, during the entire thinking on internal metrics and systems of the company, assumes that the end user is somehow both the head of the security, they’re the VP of marketing, they’re the person who logs in every day. They’re also the legal team.

And they’re at a certain point in a funnel, and they know that they’re at that point in that funnel and that that’s the only funnel that they’re in, and that they have no other job other than getting to the end of your funnel for you. And when you see all this and you play it back to them, you’re like, “Well, you do realize on their side, they have to go through procurement and they’re going to be asked to demonstrate competitors who at least have sufficient similarity on different price point or like different value points.”

So they can legitimize the purchase because you’re asking them for like 100 grand and it turns out like most businesses aren’t that badly run, that they’ll actually sign like a multi-year annual contract for like a couple of hundred grand and pay for it upfront. But all of this, from adopting your thinking from a go-to-market point of view, to getting into the shoes of your customer, it seems to be a thing a lot of businesses really struggle with.

Bob: I remember we had met a couple of times, but by the time that you’d finally said, “All right,” the sales had plateaued around 2012, ’13, somewhere around there, and it was one of the things like … and the tagline was “We can manage your customer data from cradle to the grave.”

Most people when you ask them, “Tell me about the best sales experience you’ve had? Who was your salesperson?” They’ll say, “Well, they weren’t my salesperson, they were my concierge. They were my help.” Sales is almost like too bad of a word to say that they were, because they were so much more than that, right?”

And it was one of those things and like, “Well, this is the job we do.” And we’re like, “Let’s just go talk to people.” And I did remember Paul was there and you and Eoghan and a bunch of people. And the first thing  you started here is you realize like, “Oh my gosh, we’re literally calling out all these features and benefits and they don’t even know how to talk about the problem.” Like, “Oh my gosh, how do we handle support?”

Or like, we get people to the door, but we can’t get out. And you’re talking about all the things they could do, and they can’t even search for that yet. And so, the whole notion of getting them from what we call first thought to passive looking, and then you guys kind of changing, not only the marketing, but then the product side of it was kind of like, “Ugh, these are the things that people want.” And so, to be honest, that’s a very common thing where people come at sales from a marketing perspective and they don’t actually think about buying, they just think about attracting, like getting people in the door as opposed to helping people make progress. And to be honest, that’s the bigger difference is that marketing is about maybe getting attention.

But ultimately,  most people when you ask them, “Tell me about the best sales experience you’ve had? Who was your salesperson?” They’ll say, “Well, they weren’t my salesperson, they were my concierge. They were my help.” Sales is almost like too bad of a word to say that they were, because they were so much more than that, right? 

Selling to the right person at the right time

Des: Yeah, which I think it’s still a hangover from the days of, everyone hates this feeling of being sold to or just like, it’s like this idea of haggling in a market versus it being like two people trying to share a problem, and they share a solution and both of them are incentivized to do. The interesting thing I remember from the period of time you were describing when we worked together was that, we were saying like, one of the reality checks for us was like, we were just saying too much to customers. We were actually making it hard for them to solve their exact problem, because we were telling them all this sort of shit that they didn’t care about at the same time too.

And I remember, seeing interviews with someone from support being like, “Well, I really wanted to buy your tool for support, but it sounds like I’d have to talk to the head of marketing too and I’m like, “Why would they need to do that?” And they’re like, “Well, because that’s the way this looks like it got set up.” And I was like, “Wow.” And then, what’s funny is that if we fast forward maybe five years, last year I was talking to our head of sales. I was basically asking a question of like, “Hey, why is it on our enterprise deals? We don’t see them installed. We don’t see Intercom get installed on their mobile software as part of that deal initially.”

And I was expecting to hear an answer like, “Oh, the lazy reps aren’t pushing it, or, it doesn’t come up in the conversations or whatever.” The answer I got was far more insightful. It was like, “Because the customers didn’t have a problem that that solved.”

“The customer doesn’t buy it when you’re ready to sell, the customer buys only when they’re ready to buy”

And for me, all this would be doing is making the conversation and the discussion more complicated by trying to add stuff in there that’s got nothing to do with the desire of the customer. But she was like, “Hey, I get from your point of view, this is a free thing that we’re just throwing in and it’s the extra like, “Because if you use Intercom, you got it on your mobile too.” But she’s like, “But money is far from the main concern here. The actual concern is time.”

And for us to be like, “Hey, we’re also going to sell it in the app, it would destroy the deal because you have to get a mobile app team in, we would probably have to get more developers in, next thing it’ll be a discussion about file sizes of the STK that we embed.” She’s like, “Why would we do that? Why not land, demonstrate their value and then over time trust in ourselves that the problems we solve in mobile will also appear and they’ll talk to us, because we’re going to have a good relationship with them.”

And what came back to me was you saying to me before that the customer doesn’t buy it when you’re ready to sell, the customer buys only when they’re ready to buy. And when you realize that, you realize, you have to just trust that the right things will happen as long as you’re running a good product, that they will upgrade when it makes sense. They will buy more products when it makes sense. But all that you can do is influence and nudge and get a bit of awareness, but what you can’t do is create demand when it doesn’t already exist, or maybe put it a different way, you can’t create the struggling moments when they don’t happen.

Sales is your superpower

Bob: That’s right. You can make them aware of a struggling moment they might not be aware of. But the reality is, if the struggling moment doesn’t exist, it’s very hard to create it. The interesting thing is, you start with that and take a step back and look at the bigger things around. So it’s the end of the quarter, and we’re going to offer a 20% discount to whoever signs by the end of the quarter, so we can meet our number. Okay? How stupid is that? Really think about this. I made a guess probably 12 months ago at the church of finance where we should be at, and I’m willing to actually devalue the product when they’re willing to actually pay full price within a couple of weeks after the first. But the real issue is that we’re willing to discount our value and make them feel like they got a deal when the deal doesn’t matter. When you really hear people, they don’t necessarily want a deal, especially when it’s a problem they care about because at some point, who wants to save money on a problem that’s causing them a lot of pain?

And so, they start to realize there’s these bigger other problems that, like the aspect of treating sales, it’s like a math equation. Well, I get 100 calls. If I get 25 call backs, I’m going to get 12 appointments and those 12 appointments are going to get me to three proposals and I’ll get one of them. So for every 100, I get one. And it’s just like, crank the numbers. It’s like, yeah, but don’t you want to know how they do that? Or don’t you want to know why they want to do that?

And so, what we realize is we’ve turned people into just order takers, as opposed to sales professionals. And you start to realize that in any real business, salespeople are actually the most important, whether I’m selling you to join as an employee, whether I’m selling the banks to go or the investors to get money or investment, sales is at the cornerstone of any startup. And the reality is like, it is a profession. It’s not something that’s just like order taking.

“Sales is  the superpower you offer your customers to ensure that they can realize the value that you offer them”

Des: Right. And which kind of comes back to the same thing. I think people reluctantly layer in sales. And then what happens is they say, “Okay, well, I guess our customers could talk to sales if they have to.” And then they’re like, “Well, why are we employing these people? People are buying it just fine off the website.”

And I’d always be the one saying, “They were just buying it off the website, but they were also just constantly leaving having not really tried it, and you were wasting a load of time running around high-fiving because IBM signed up, only for IBM to quit 11 days later.” And I’m like, “You’re reprioritizing everything because you’ve got IBM in the door and all you’re actually doing in those circumstances is you’re producing a load of people who are out in the market and they’re saying, oh, that product? I tried that but it didn’t work.” And that’s not good for your brand. So what sales is, is as we said earlier, it’s the superpower you offer your customers to ensure that they can realize the value that you offer them. 

But I do think that there’s something generational in this last decade or the software, where people seem to think that all business should be conducted with 100% self-serve online with no humans talking to humans, but they don’t realize that, like when you’re in a larger company, you have larger problems and you’ve got a complicated deal shape, and it’s too multifaceted for it to be a linear funnel signup. If it was, it’d be great, but it’s just not how that works. 

A lasting legacy

Des: One sad thing that has happened since we last spoke Bob was the passing of your friend Professor Clay Christensen. You’ve described Clay to me before as your teacher, your mentor, your advisor and a friend. Look, I can tell you, if it weren’t for Clay – you and  would not be speaking. I saw Clay speak at the Business of Software in 2012, where he gave what was a near-on two-hour lecture. And it was enthralling. It was probably like one of the best lectures I’ve ever seen. It’s still online. I went from there to obviously reading all of his books, following every interview he ever gave, you name it. But I’m not the subject of this interview, you are. You’ve had like a front row seat to perhaps some of the most important work by perhaps one of the most important people in business strategy. What words would you use to describe his lasting legacy?

Bob: I’ve got a whole podcast on that.

Des: Of course.

“The best way to think about your life is not how much money you have in the bank, but the number of people that you’ve helped and how you’ve made the world a better place”

Bob: First of all, he was humble. He would almost always start from the premise of not knowing and wanting to learn –  it was at his core. I had the luxury of being able to meet with him once a quarter for four hours with no agenda for almost 27 years. And what I would say is every time I’d come to the office, it would be fun. People would want to come in and sit with us and talk and he’d be like, “No, no, no, no, I get it.” And he’d literally sit on the desk and he’d swing his legs and he’s like a five-year-old kid, just like, “Okay, what are we going to talk about today?” Just so interested in everything. And I would bring things like, “Why are there no sales professors?” He’s like, “Oh my God, yeah, that’s a great one.”  And then we just drift and we’d end up having these pictures on his whiteboard that were demonstrative of whatever we were thinking about at the latest moment.

To be honest, it was that childlike curiosity and the humbleness to realize that he didn’t know, and that it was about learning and figuring it out. And his constant wanting to help people. How Will You Measure Your Life is a book which I’ve basically adapted my life around. Which is, the best way to think about your life is not how much money you have in the bank, but the number of people that you’ve helped and how you’ve made the world a better place. And so, to be honest, those are the three things that as a mentor, he passed on to me.

I think one of the reasons why Clay and I got so close is, all I worried about was how could I help Clay? And all he worried about was, how could he help Bob? And the crux of it is that we always wanted to help each other more than we wanted to help ourselves”

My next book is actually called Learning to Build and it’s about Clay and Deming and Taguchi and Dr. Will Moore and these people who took a dyslexic illiterate kid from Detroit and gave me the gifts of theory to help me become a creator of product and services and a teacher, which, by my high school career tests, that I should be a baggage handler or a mail carrier and I was a football player so that kind of made sense for me, but my mom was like, “No, you can do better than that.” And so, the notion of finding these people and being mentored by them and being peers with them at some point, it was just kind of amazing. So I think Clay, I think these people come into your life all the time. I think you have to invest as much time into them.

I think one of the reasons why Clay and I got so close is, all I worried about was how could I help Clay? And all he worried about was, how could he help Bob? And the crux of it is that we always wanted to help each other more than we wanted to help ourselves.

Des: Beautiful. Yeah, I totally agree with you on How Will You Measure Your Life? It’s an incredible book. Bob, thank you so much for joining us. We’ll include all of your relevant links. You’re on Twitter as BMSA, your company’s rewired group. Obviously, your most recent book is Demands-Side Sales. Thank you again for the conversation. It’s always a pleasure to chat and I hope to do it again about your next book.

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