Demand-Side Sales: The Forces Behind Every Yes

Drew: Hello, Renegade Marketers! If this is your first time listening, welcome, and if you're a regular listener, welcome back. Before I present today's episode, I am beyond thrilled to announce that our second in-person CMO Super Huddle is happening November 6th and 7th, 2025. In Palo Alto last year, we brought together 101 marketing leaders for a day of sharing, caring, and daring each other to greatness, and we're doing it again! Same venue, same energy, same ambition to challenge convention, with an added half-day strategy lab exclusively for marketing leaders. We're also excited to have TrustRadius and Boomerang as founding sponsors for this event. Early Bird tickets are now available at cmohuddles.com. You can even see a video there of what we did last year. Grab yours before they're gone. I promise you we will sell out, and it's going to be flocking awesomer!

You're about to listen to a Career Huddle where our flocking awesome community, CMO Huddles, gets exclusive access to the authors of some of the world's best-selling business books. At this huddle, we were joined by Bob Moesta, co-founder of The ReWired Group and author of Demand-Side Sales 101. Bob shares how understanding why customers buy, not just why you sell, can change how you build products, market them, and create demand. If you like what you hear, please subscribe to the podcast and leave a review. You'll be supporting our quest to be the number one B2B marketing podcast. All right, let's dive in.

Narrator: Welcome to Renegade Marketers Unite, possibly the best weekly podcast for CMOs and everyone else looking for innovative ways to transform their brand, drive demand, and just plain cut through, proving that B2B does not mean boring to business. Here's your host and Chief Marketing Renegade, Drew Neisser.

Drew: Hello Huddlers! I'm thrilled to welcome Bob Moesta to our session today. Bob is an adjunct lecturer at Northwestern Kellogg School of Management and a guest lecturer at Harvard Business School. When you read his book, you'll get this – what's interesting here is there used to be no people who were professors of sales, and one of Bob's sort of life missions has been to elevate sales as a profession, and he's done it. He's helped launch 3,500 new products and services across nearly every industry imaginable, from defense and automotive to software, financial services, and education. Grew up as a kid with dyslexia. That sort of drove a lot of the things that he did. And he is the author of this book, Demand-Side Sales, which offers, I think, a fresh perspective on how to understand and connect with customers. Now, Bob, first of all, how are you and where are you?

Bob: I'm in my hometown. I'm in Detroit, Michigan, born and raised. I've lived here my entire life, and I plan to live here the rest of my life. So this is my home, this is my home base. I've done seven startups. I've started companies in other cities because it's easier to work 20 hours a day when you're somewhere else. When you have a family, and then you come home to the family. And so I've always basically had this home base, but I travel quite a bit.

Drew: I love it. All right, okay, so we've established where you are. Awesome. Let's do one thing I like to do, just in case the audience needs to leave early, or we need to convince them to stay. Provide sort of three very short, bulleted insights about sales that you'd love B2B CMOs to understand, and we'll go through them one at a time after your list.

Bob: Number one, people buy differently than how we sell. Most people don't understand that. And to realize like understanding the buyer journey and understanding what causes people to say today's the day they want your product or service, that's what you need to figure out. The second part is that context and outcome – context creates value, and contrast creates meaning. So it's this aspect of knowing the situation your customer is in, or what has to happen to your customer to make them ready for you, right? And so a lot of times, we keep marketing to people when they're not ready for us. And so we just waste our money, right?

Drew: Interesting, okay, is there a third?

Bob: Yeah, the third is that the fact is, there is no ideal customer, right? There's a whole bunch of different customers, and you have to realize that ultimately we have to learn to make trade-offs. And so ultimately people keep trying to build the ideal thing, the ideal customer, the ideal product, the ideal whatever. But the reality is, what we have to actually really understand is what trade-offs do customers make, and how do we actually understand how to mimic their trade-offs into our product and services.

Drew: Okay, all right, that's a lot to unpack, and I'm excited to do it. I almost want to start with the third bit, but let's go back to the first one. So people buy differently, and again, this is how we're in B2B land. And I know there are a lot of folks who see B2B and B2C as similar, but I think you and I talked about it, there are a lot of differences. One is buying committees and so forth. So let's talk about in the context of B2B, what you see in terms of the difference between how people buy and how people sell?

Bob: Yeah, so the first thing is, I'll tell you that in my first B2B, we literally set up a way in which to sell the way we wanted to sell, and then we tried to get people to buy from us that way, right? And that's kind of the first mistake I made to really say, like, okay, I need to understand how they want to buy, because ultimately, they don't want to hear all my features and benefits, because in certain situations, there's only three or four that are relevant to them. And the moment I tell them too many, they think I'm too expensive.

Drew: Right? If you get your laundry list, "Well, we do this and this and this."

Bob: They're like, "I don't need all that. I only need this. Can I get a 20% discount?" So part of this is being able to tune the pitch to the context that people are in, right? And so understanding that is really, really important. And so I start by – so for example, one of the things I did is I built houses, right? And I didn't go interview people who wanted to buy a house. I interviewed people who bought my houses. What caused them to say today's the day that they need a new house? It's not random. Nobody buys any product randomly, ever. And so this is the thing is, the sales process is set up – if I have 100 people, 100 leads, I can get, you know, 25 conversations that give me 14 proposals that can get me to, you know, 25 or 10 meetings, it gets me to three closes, like they treat it as probability theory. But that's just not right. Sales is not about probability. Sales is about causality. What causes somebody to buy? And so we need to study the people who have actually come to us, and we actually need to study the people who left us, because the people who leave us are just as important, because we learn there's a lot of people who I'll say, the phrase I use is people bitch, but they don't switch. So these are the people who go like, "Oh, it'd be great if you had this feature. Oh, my God, that'd be great if you had that feature." But one, you can't charge anymore for it. And two is the fact is, ultimately, the fact is, they'll probably never use it. The thing is, to actually study the people who have churned from you. You'll actually see what causes people to literally say that this is important enough to go build it. So I never build features or products on things that people just tell me about. I need to actually see them try and have an effort to solve that problem before I actually build that feature.

Drew: It's so funny. There's a famous story. I don't know if I mentioned this in a pre-call, but I've done it on this with this group before. Famously, Dell surveyed all its customers and said, "Hey, what kind of things would you like us to buy?" And they said, "A Linux laptop." So they said, "Great, okay, we'll build a Linux laptop." And it was like their worst selling in the history.

Bob: So this is the other part of this is people don't really know what they want. Somehow we think they do, and we literally listen to their words with a level of precision that is 10 times more precise than they're sending it to us. So they'll say, "Oh, I want it to be convenient." And like, oh, 1,000 people said they wanted to be more convenient. And then we go in and try to interpret what convenient means, and there's 40 different definitions of it, and all these different things we can do. But nobody asks, like, "What do you mean by convenient? Give me an example of convenient. Give me an example of what's too hard." Because most people can't tell you what convenient is. They can tell you what too hard is.

Drew: Interesting. So yeah, and your book spends a lot of time talking about getting deeper in these conversations, and I want, but I want to make sure that we keep going through it so because we're going to come back to this getting deeper, but so let's go make sure we cover the second point, which was context creates value and?

Bob: Context creates meaning. If so, here's the thing: if you give somebody one proposal, there's not enough context for them to know what to do. Sixty-two percent of all proposals in B2B go unanswered because they have no contrast. And so what happens is, what I do is, for example, I give them three different ways in which we can implement—I give them three different approaches. But people need threes. This is what most people don't understand. If you really study how buyers buy, they use three as the first thing they do. They actually look at all three, and the first thing they do is eliminate one of the three, right? And so now they have confidence about the one they eliminated. And then they compare the last two not to each other, but to the one they actually made a decision about. And so they eliminate the second. And so ultimately they'll say, "Oh, I bought A." But the reality is they don't want A. They just eliminated B and C. And so we have to actually sit in the shoes of the customers. We have to be empathetic to how they think. And so ultimately, without actually sitting in their shoes, we end up feeling like we have to tell them everything—show up and throw up. And it doesn't work.

Drew: I love that "show up and throw up." You know, knowing a number of the folks that are present with us today and others that will be listening later on, yeah, they know they need to study the customer journey. There's no doubt that they would say, "I already knew this. I know I've got to know my customer better." But nonetheless, it feels like there's another layer to this, which you're saying is you don't know the customer as well as you think you do, because you're not asking the right questions in the right way. Is that a fair interpretation of that?

Bob: That's a little more confident or arrogant than I would state it. What I would say is, the fact is, we are more obsessed with our product than them, right? And the reality is the more we can become obsessed with them. So for example, in home building, what I realized is one of the biggest struggling moments for people who were buying my downsizer condos—basically people who are retiring—is that they'd never moved in twenty years. And so the whole thought of moving was so daunting that the fact is, I included moving and two years of storage so they could actually sort through this thing and actually do it. I grew sales almost twenty-eight percent by offering something that was really nothing that I did as a builder, but it's something that's part of the moving process that is actually really essential for basically having people buy my condos.

Drew: And that's so interesting. And I love that story. And I was just thinking about it. It's like my wife and I lived in this—and I lived in this apartment for more than twenty years, and we keep talking about Swedish death cleaning because, God forbid, our kids had to deal with this. And it is a—it's a great insight. But the thing that I like more about the insight is that you created a solution that was more than what you were selling. And I think oftentimes, and I talk to a lot of folks that sell SaaS products, and there's a high multiple for a SaaS product without actually providing the service. The service you get a low multiple. Yet often it is the combination of the product and the service you provide that creates this sort of stickiest bond with a customer. But they don't want to talk about service.

Bob: We're not in the service business. What I learned is, for example, as a builder, I might be a builder on the supply side—like my business and my processes are set up to build homes, so from a supply side perspective, that's what I do. But ultimately, on the demand side, I'm a mover. My job is to help somebody move from their old house to a new house. And what I learned is that I could actually help sell their old house as well. And so their old house needed fixing. And so as much as I did one thousand new homes in Detroit, I actually fixed up five hundred used homes. Because if I'm a mover, my thing is all I've got to do is figure out how to get people to move from one house to another, from an apartment to somewhere else, from a manufactured home into a house. I mean, there's all these things we found. And so you start to look at the market completely differently if you actually reframe it from the demand side of the world.

Drew: And that is so—the context creates value is exactly that notion right there.

Bob: The context they're in actually helps us understand what value means to them.

Drew: So I'm hoping that this is inspiring folks to think about their customers a little bit differently and how they go about getting to know them. Now, which gets us to the third point that you brought up, which is, there is no ideal customer. We ought to unpack that, because everybody talks about their ICP. I mean, it's like, it's hard to have a call. "Well, our ICP is this, then we see the intent data on this ICP, and we're going to—just now we know that person, because they're on our target list, is a prime customer. We better get a rep on the phone with them right away."

Bob: That's right, but we don't know anything about their context. We know nothing about their struggling moments. We know nothing about what they're really struggling with. And so part of it is, we describe ideal customers by the demographics and psychographics of the company they might be with, but that doesn't mean they're ready to buy. Doesn't mean they have any problems. And so you start to realize that ultimately it's about the trade-offs that we have to make. And so understanding the trade-offs the consumer—so for example, when I surveyed people in the home building industry, which, to be honest, I was forced to do by the previous system that I inherited, and it would be like, "Oh, I want an Energy Star compliant"—was the number one requested feature, was an Energy Star compliant home. And ultimately, the fact is, it cost us forty-two thousand dollars to make the home Energy Star compliant. And as much as I put it in, everybody was excited for it. We sold zero of them. And what happened is, what I realized is the trade-off was, "Do I actually make it Energy Star compliant, which means I've got to stay in this home for over twelve years to break even, or do I finish my basement," which was also forty thousand dollars? Turns out, everybody finished the basement. And so this is where, all of a sudden, you start to realize what they say they want and what they want is very different. And so one of the things that I learned, and to be honest, again, remember, I'm an engineer. I've been building things my whole life. I've been actually—so this is almost like an engineer's view of sales, right? Take that for what it's worth, but there's an emotional, social, and functional component. And ultimately, I had to go learn, not marketing research techniques. I went and learned criminal and intelligence interrogation methods, because ultimately, consumers lie. They lie to themselves, let alone lie to you. And so part of this is being able to understand what they mean and why they're saying what they're saying, so you can sit in their shoes. So I treat these interviews as if I'm trying to be an understudy to basically play them in a play in another situation. So I have to know how they're going to say that the patterns are going to speak. Who's in charge—all of that, right?

Drew: I also, when you—the minute you went to "criminals," of course, and I saw you referenced Chris Voss. He comes to—we had him.

Bob: Chris Voss is amazing. I started a book on that, and then I read his book. I'm like, "Yeah, I don't need to do this. This is perfect." He's very good at what he does.

Drew: But what's so funny on that one is, so we had Chris on a career huddle, and ultimately a podcast, and I had listened to his book actually twice, and it's a professional announcer. So when you actually meet him, it's like he doesn't sound anything like—you know, it's funny because he has this wonderful voice, and the narrator is amazing.

Bob: Let me just hit the one point that's really important in that one is like, when I'm doing these interviews, for example, I'll play back what they told me incorrectly, because I want to get them to know. Getting to "no" is the—like the moment they say, "Yes," there's no other question you can ask. And so ultimately, when I'm trying to talk to customers, I want them to say, "No, no, no, that's not it." And then fix it for me, because now you get more details. And so one of the hardest parts of this skill is actually playing dumb. I might know the answer, and I know that what they're saying is wrong, but I need to hear their words for it, not my words.

Drew: The famously Columbo technique, exactly. It's funny. I know a market researcher, an interviewer, who does that all the time and uses it to great effect where he'll ask an innocently stupid question. You did say, Joe—before we wrap up on this third point. And I think there's a lot—you talked about the fact that there's no ideal customer. There's a lot of difference, and we have to think about them differently. Let's talk about that a little bit more. You mentioned something like ninety-four percent or—I wasn't sure what that...

Bob: Sixty-two percent of most B2B proposals go unanswered because they don't have any contrast.

Drew: Okay, so that was one, but there was another point just about this not being there, not being an ideal customer. And this is what I'm going to state what I hear, which is: we do have an ideal customer profile because we can look at our last 10 wins, and they were all companies that were 500 million to a billion. They were all this kind of structure. The first areas started from a marketing ops person who was trying to solve this particular problem, and, oh, by the way, we also had a lot of intent signals because they were at review sites. They were at all these other places. So we kind of know that they're in the market for it too. That's what they would say.

Bob: That's right. That's how—so what I call that is that's aggregating or averaging all the things around the last 10 clients, and when you average it out, they don't exist. So when you go to find them, they don't—they're not there. And so part of this is to realize that at some point in time, just because they're 500 million, that doesn't cause them to say, "Today's the day I want your product." And so this is what I'm saying: we end up building personas. We end up building all these different kinds of aggregated views of customers. But that's actually just—they're all just made up. I would tell you, just go talk to 10 customers. You'll learn more talking to 10 customers and seeing the patterns across 10 customers than you would by actually trying to aggregate all that information.

Drew: Interesting. So you mean that when the survey says they're 2.3 kids, there isn't a 0.3 kid that we can find.

Bob: That's exactly right. So what you want to do is interview: Why do people have kids?

Drew: Hell of a good question, one that we are not going to be able to answer.

Bob: I was going to say we don't want to. But this is the point: we're asking the wrong question.

Drew: So fascinating. And let's go deeper on that, because that's a big part of your book, and I think it will help folks understand what you're talking about, because you actually do a lot of Q&As and so forth, and role playing in the book. Let's—if we can do that in the context of a B2B interview, and I think it's tricky because you have in B2B, you might have a user who's using the product. You'll have a buyer, you'll have an approver, you'll have a tech person, you'll have a security person, you'll have the CFO, maybe even it'll get as high as the executive because it's a big purchase. So there's a lot of different people along the way. And you know, are we going to have 10 interviews with each one? Because—

Bob: I only interview one person. I actually probably need two. But the one person I talk to is: who is the person taking the political risk to change the system? That's the only person who was actually creating the energy to make it happen. Everybody else is there to say no, and all I have to do is not get them to say no, but I don't need them to say yes. I just need to make sure they don't say no. And so you start to realize that if I try to aggregate everybody's point of view, it's almost like we have to be a family therapist, right? Because so-and-so wants this, and somebody else wants that, and somebody else wants that. It's really about what's the business problem we're trying to solve, and what are the trade-offs you're willing to make in order to make that happen? This is where people would go, like, "Oh, well, we're worried about speed of this thing," and blah, and they're going on and on. And next thing, it's like, "Well, it's got to pass our security protocol." It's like, okay. And all of a sudden, it turns out it doesn't meet their security protocol, but it's such a good thing they're saying, "We're going to put it outside the firewall. We're going to treat it this way. Do it this way." Next thing you know, they're using it. So the objections don't become objections. The objections are really trade-offs you have to learn how to manage.

Drew: So I think the person that takes the political risk often—CMOs will call this the champion.

Bob: Yes, yes. Sponsor, the champion, that kind of—but ultimately, these are the people, if you think about it, that this purchase is caused. I only talk to people who actually were responsible for causing it. The other thing is, again, as an engineer, one of the reasons why I got so deep into sales is because as I build product, I had to realize I have to build the product for two people. I have to build it for the user, and I have to build it for the buyer. But it turns out that the user usually has very little voice in any of this—very little voice. And so I can build the most user-friendly thing in the world, but the buyer is not willing to pay an extra dime for it, right?

Drew: Yeah, I mean, unless you're sort of in the PLG world, where you get a bunch of people to buy it.

Bob: There's some exceptions, but what I'm saying though is that what'll happen is the reason why you'll get fired is because the users can't use it. The reason why you get hired is because the buyer can buy it. And so you have to actually learn how to manage the trade-offs between the buyer and the user. So think of like Salesforce, right? The reason why people buy Salesforce is, "I want to see the sales process. I want the data for all of everything that's going on. I want to be able to see the entire process." The problem is that the user, who's the salesperson, literally hates it, right? And so what we said is we've got to—and everybody had their own sales in the early days. Everybody has their own sales approach. And so you're trying to unify the sales approach, and then when you actually do that, everybody's running two systems, and your sales will go down if you actually burden the salespeople too much. So don't actually try implementing all the stuff that the buyer wants up front. But say, "Here's how we're going to get there, and here's early things we're going to do to help the users, which are the salespeople, use this so we can get that data you really want to see." Negotiate the buyer against the user because they don't have the same needs.

Drew: So interesting. There is a target audience here in your theory, right?

Bob: Yeah, it's a target who, when, where, and why. It's situations people find themselves in. This is where you look across wide demographics, and it turns out that the same underlying mechanisms are there that cause them to buy your product. And so what you want to do is understand those mechanisms of what has to happen to somebody for them to even see you. You have to realize there's a process of how people buy. The first thing is called first thought. The reality is the first thought is a question that you put in somebody's brain to basically say, like, "Could this be better? Is this really efficient enough?" And the moment that they have the space—so my mentor, Clay Christensen, would say, "Questions create spaces in the brain for solutions to fall into." So we shouldn't start by leading with our product. We should be starting with "What's the one thing you struggle with that you would love to actually fix that would move the needle next year?"

Drew: And I wonder, as folks are listening to this, if they know the answer to that right now, right? And I wonder if they went to their—and did some interviews, they would pretty quickly find what that one thing is. And it might surprise them.

Bob: Exactly. And it turns out there's not one thing. There's usually three or four things. And so you have to understand that people—and so I call the framework "jobs to be done"—and that people don't buy products. They hire products and services to make progress in their life. And so what progress is the sponsor trying to make? And how is it trying to help the business? And ultimately, what are they struggling with? If there's no struggling moment, there is no demand. You can't convince somebody to buy something they don't need.

Drew: "Struggling moment" is such a great phrase. I think it's a powerful framework for folks to think about.

Bob: And I want to contrast it to two things. This is not a pain point. A pain point is basically kind of one of many struggles that they have. And so you have to actually realize that it's kind of like their knee finally hurts, but they've got a lot of other problems going on that you've got to be able to see the whole thing, because otherwise they're just going to think it's the knee. And the reality is, the problem is bigger than that.

The second part is, the reason why it's called a struggling moment is because that's the very first moment where people realize they have to do something different. They have to do something new. Buying something is about changing something that's broken, and it could be broken because we're not reaching the opportunity we have. It's like there's a dark side and there's an upside. We call it the context and the outcome. What's the outcome they're seeking, which is not necessarily the same as solving the problem? So people assume symmetry between problem and solution, or problem and outcome, but the reality is, they're not necessarily symmetrical.

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Drew: So I wanted to go back because you've said a couple of things, and I just want to repeat it. They're changing. They're looking at change. There's the struggling moment. Something's broken, and they've figured that out. Now, there are times where people don't know that they're having a struggling moment. And sometimes, you know, in the world of category creation, people try to sort of dangle out, "Hey, there is this problem you may not have even thought about before."

Bob: But it has to have some consequences. It has to have some upside. It has to be just saying that it's a problem doesn't actually make it worth solving. And so part of this is you have to actually understand their world. And most of the time, we're trying to convince them of what's going on in their world, when we don't really know what's going on in their world. You know, as you know, the best salespeople don't talk, they listen. My belief is all the people who are here already know that, but that's the big thing is that the most junior salesperson just walks in and talks.

Drew: This is an interesting dynamic, and I'm just going to throw this out there right now and see how so there has always been, and probably always will be, tension between marketing and sales. Some of that tension is going away in the sense that it used to be there was a handoff where marketing would get this qualified opportunity and then pass it over. There's less of that, and more of this is an opportunity for the company, not marketing or sales. We're going to manage and work with this opportunity all the way to the close. Doesn't matter who's in which department doing it.

Bob: I would include customer success in that as well. So it's marketing, sales, and customer success should actually be one organization. So I need customer success early in marketing, and I need marketing when I'm implementing. So for example, I've sold something to somebody, and now it's being rolled out to the entire organization. I need marketing to help me talk about what it is. Marketing usually only helps me convince the buyer, but I have to convince all the users too. We put that on customer success, but customer success aren't marketers. They're functional people to basically tell you how everything works, but I've got to still create some marketing message around why we're doing this. Interesting. And so I would much rather have a team of marketing, sales, and customer success in one team, and have them work together than trying to actually have the handoff. The handoff is a broken model to me.

Drew: I don't think anybody would argue with you, and I think it's increasingly so. I mean, given the new generation of buyers who aren't one, experienced as buyers and two, are self-serve oriented. Self-serve first, it's really, they're, you know, if they could, they would buy everything the way Amazon sells everything.

Bob: But so let me give you an example. So in the home building that I did, right, we were getting 1,000 leads a month, right? 1,000 leads, and ultimately we would sell about 20 houses a month off those 1,000 leads. And what I realized is the leads we got were so bad that the fact is, I said, we need to put some like a set of questions up front so we understand why are they serious about moving and what is it about? And so we went from, and I put this thing in front, up front, and to be honest, our leads went from 1,000 a month to 200 a month, but my sales went from 20 a month to 80 a month because I was only getting the right ones. To be honest, I could actually cut my sales staff in half because I didn't have to have them look at all those people who were not even really interested at all anyways. And so this is where you start to realize, when you click them together, they actually have similar alignment, but when you break them apart, marketing is about getting leads. It doesn't matter how many leads, the more leads, the better. All leads are good.

Drew: Yeah, there's this notion of coverage. Well, we have 10 BDRs and they need to have five or six leads per month to work. And so therefore we need to bring those in and you back it up. And so the irony is increasingly seeing a lot of folks getting rid of that function and really trying to qualify better, as you described it. And that's great. You cut your leads by 80% essentially, from 1,000 to 200, and you have quadrupled your close rate. I mean, that's math that I think any marketer would love. The thing is, they have to be comfortable saying, "You're not ready for us." Yeah. And, you know, it's funny, I went to a trade show just a couple weeks ago, and it was a really great conference, and I visited a lot of booths, because there was a lot of technology there. And I talked to a bunch of them. Not one, and about 10 of them scanned my badge. All of them followed up with an email, "Hey Drew, great to meet you," and other things, and I'm not a buyer in any of those circumstances. I'm an influencer, but I am not a buyer, and yet I got a, "Hey, let's set up a meeting so I can do a demo" email. And I had to, I created a standard response: "Take me off your list. I don't want to waste your time or mine. Do a better job qualifying your leads."

Bob: One of the things we're doing in qualifying, so part of the framework is this notion of what we call Forces of Progress. There are things that have to happen to you that enable you to be ready. And so we start to talk about push forces, which are usually contextual things wrapped around you. There are pull forces, which are outcomes that you're seeking, and those are the fuel of the change. But then there's what we call the friction of the change, which is basically the anxiety of the new. What questions do they have? What worries do they have about the new? And the other is, what are the habits they have to give up in the past that will actually hinder them from doing so? If they don't give up this, they're not going to be able to implement that. And so you start to realize that this becomes the salesperson's guide. And what we did is we actually in Salesforce, we created: What's pushing them? What's pulling them? What anxieties do they have? What trade-offs do they have to make? What habits do they have to give up? So we can, and if the salesperson couldn't answer those questions, they were nowhere near ready to close.

Drew: Let's talk about those in detail. Because again, really good pearls. They come right off your mouth. I want to make sure that everybody gets it. So let's just go into the push. What more detail on that?

Bob: Yeah, a push. So, for example, what causes somebody to buy a new house? Right? So first of all, these are not one thing. They're sets of things that have to happen to somebody that says, "Today's the day." Part of it is, so think about people downsizing houses. What has to happen for them to say it's time? Well, their kids have to move out of the house. Literally, the house is too big. The neighbors start to move away. Like there's all these different things that are pushing them to say, "I've got to change." In the B2B world, this is the tariffs are coming. The fact is, we have inefficiencies. This machine broke. We have this opportunity to basically go into this new market. What's pushing them to start to look to do something new? And so ultimately, that's a push. If there is no push, there is no struggling moment, there is no opportunity, there is nothing to sell. They can't see it. They just keep doing, we're creatures of habit. We'll keep doing what we're doing. So we need a push, but the moment we have a push, then we have an opposite on the other side, what I call the pull forces, which are the things, the outcomes you're seeking by doing this change. Am I seeking to grow the business? Am I seeking to be more efficient with my sales? Am I seeking to basically downsize my sales force? What are the outcomes I want from this? And those two things that, like, you could call them pain and gain, but pain and gain is very limited, because sometimes there's no pain from it, but it's part of the context that actually creates the pain, right? You want to be able to have that.

All the second half of this is the friction, the anxiety, objections, the things that they're worried about, that would keep them from buying this. Like, so what's going to happen to all our data? How long is it going to take to port it over? What's the implementation time on this thing? Like, all those anxieties? And what you start to realize is, you can have a lot of push and a lot of pull, but if you have a lot of anxiety and a lot of habit, there's a lot of energy in the system, but it's not going anywhere. And so what I realized, for example, in the home building side is, if I added moving and storage, I reduced the anxieties so much that I actually had to sell. It was easier to sell. Nobody wanted moving and storage, because they know me as a builder, right? Nobody said, "Oh, I wish you could do that." Like I just literally saw that that was one of the biggest struggling moments that they had so much anxiety about that. So that my builder down the road was giving free granite and hardwood, and I was giving moving and storage, and I outsold them 10 to 1.

Drew: It's so interesting that the, I think, the data that I saw recently was that in B2B land, 60% of deals that are prospective deals, don't, they end up buying nothing. Yep. Which means all of those pitches, nobody figured out how to resolve the friction points.

Bob: That's correct, or have enough push and pull—enough fuel to make the change. So sometimes it's a fuel change. Not enough fuel will do it, but also too much friction will do it. And so part of it is thinking about it as a system. That's me as the engineer, thinking about the buyer as a system and saying, "What's operating on them?" And it's social, emotional, and functional. This is where there's a big misunderstanding that they say that B2B is very, very transactional. And the reality is, B2B is extremely emotional and extremely social. If I don't buy this, I will get fired. If I buy this and it screws up, I will get fired. That's very emotional. There's a risk of not doing it, and there's a risk of doing it.

Drew: Right.

Bob: Both have emotion.

Drew: One could argue that fear is a lot of this, but it's so interesting because if you look at software that's going easily and getting purchased, it's generative AI. A lot of tools are getting bought and tested and so forth, and there's very little friction, but there is an emotional part. It's a fear of being left behind.

Bob: That's right. To be honest, this is where I would quote another one of my mentors who would say, "Don't ever confuse activity with productivity." My belief is everybody's trying to figure out AI, but there are very few people doing it, and most consumers don't want it. They just want the answer. "Give me the answer. You used AI? That's great. I don't care."

Drew: Yeah. Although, yeah, I won't go there because I do think there's a lot of interesting implementations going on right now.

Bob: There are, and I want to be clear about that case, but you have to realize that I work in everything from consumer packaged goods to software, to banks, and everything in between. And everybody's saying they need AI, but what they don't realize is, how does the AI add value to the customer?

Drew: Right? Well, there's a lot potentially, but it's disruptive because if people are going to AI search engines and they are stopping there, and they're not doing their own homework, and suddenly they're telling you, "Here are the top three brands in this category," and you don't show up.

Bob: You know, the other thing is, are they really ready to buy because the AI did all the work? Are they actually understanding why they really need this thing? And so they're reading it as opposed to feeling it—very different. Let me talk about that in a little more detail. So a salesperson sitting across from you and talking you through the problem is very different than having an AI and you chatting, giving it information. And so you start to realize that at some point in time, the AI might be able to gather more information and summarize it, but it's still the AI's summary of it. It's not your summary of it. The salesperson's job is to actually get them to articulate their problem and say it's their problem. That's an emotional process.

Drew: Yeah, and I do wonder if that is being replaced by someone going into ChatGPT and saying, "Here's my problem. What would you suggest I do? What's the path forward?" And I feel like enlightened users of these tools are doing that in B2B in their purchase cycle. Yes, in fact, we know they are. Trust Radius just did a buying study, and it was 17% before—it's up to 30% of buyers are now using generative AI to help them narrow the field and do their homework.

Bob: And so here's what I would tell you: it's helping them get ready to buy. This is their homework. We shouldn't think of this as a bad thing, right? You should actually think that they're going to be more ready for us. And so part of this is to actually help them with—if the AI is giving them the good information. "What did AI tell you? What do you believe it's going to—how did you think it's going to help? Why are we on the list?" "We're on the list because AI..." "Well, what did AI tell you? How? Why is that relevant to you right now?" Like, I really believe that the fact is, the thing that most people still don't believe is that sales is human, and that it's probably the most human of all the things we do in terms of actually transacting. And so we can go—when it's known, it's like, so for example, if I'm going to the grocery store and I've bought Lay's potato chips before, I'm not actually buying anything new. It's just a repurchase, right? And so the reality is, those are things we could actually get AI to help us with. But when we start to think about doing something new, we have to actually understand what is the cause of that, and there's fear and emotion around it. And they can study as much as they want, but the words aren't going to actually help them feel better.

Drew: Right. Okay, I want to make sure that we cover a couple of things that I really liked. Your tree visual, where the symptoms are the branches and the leaves, and the problem is the trunk, and the causes are the roots. Talk a little bit about that framework and how B2B marketers can use it to better understand their customers.

Bob: So think about it as features and benefits. We keep talking about features and benefits, but the thing we should be leading with is the underlying causes of why they value the features and benefits. So most people start with the end, which is, "Let me tell you what we can do for you," as opposed to, "Let me tell you who we help. They have these kinds of problems." And so part of the tree analogy is to say that the benefits are only possible if they have the problem. And you need to realize that at some point, if the problem is deep, the solution is actually a big tree. And if the problem isn't that deep, then the fact is, it's probably not a big tree.

Drew: There's some profundity in there, folks. I hope you're listening to that—that if they don't have that problem, it doesn't matter what you say. It's like if they don't perceive that, right?

Bob: But that's the 60%—we're talking at them as opposed to listening to them.

Drew: So I promised that we would go a little bit deeper on listening to them. Talk a little bit about the kinds of things that marketers could be doing, the questions in that process of questioning that you outlined so carefully in your book.

Bob: So I'm working on a new book called "The Anatomy of a Great Question"—like, what does it take to do? Like, when somebody goes, "Oh, that's a great question," how do you do that, right? And so part of this is to realize that you have to actually start to—this is, in some cases, it's a show for them, but it's also for you to learn. And so the questions have to be—one is they have to be empathetic. Two is you have to learn to mirror, right? If they speak fast, you speak fast. If they speak slow, you speak slow. Part of it is to basically make sure that they get comfortable. The other part is, typically, I try to get names. So if they say "their boss," I wonder who the boss is. "Oh, the boss is Tracy." "Okay, so what did Tracy think about that?" Tracy gives you a notion that you're now familiar with the situation. If you keep saying "your boss" all the time, then the reality is, you're just an outsider. The other is we unpack to causation. There are three layers of language, and I always say the first layer is what I call the pablum layer. This is where you would say, "Oh, how was your day?" "It was good." It really wasn't good, or maybe it was good, but "good" is to get you just to go away, right? But then the next layer—the question would be, "So what was so good about it?" And they go, "Oh, it really wasn't good." "Okay, well, what's so bad about it?" And then they go into what I call the fantasy nightmare layer. This is where they exaggerate beyond belief about that. They add the emotional aspect of how bad their day was or how good their day was. And then ultimately, the fact is, you've got to get down to, well, what caused it? And the causation—think of it as, what are the dominoes that had to fall for that to happen? And when we understand the causation of it, now we can actually figure out what to do with it. But if I'm at the pablum layer, I can't do anything. If I'm at the fantasy layer, I end up overestimating or underestimating, right? I've got to get down to the causal layer of what's causing them to even look today.

Drew: I seem to recall a sort of Japanese thing about the six whys—getting the why, the why, the why? Why?

Bob: Yeah. At 18 years old, I met a gentleman by the name of Dr. Deming, who was the father of quality, and he took me to Japan, and I learned all my methods and tools for engineering in Japan, and that's where a lot of this has come from. Yeah, so it's the five whys. But you can't ask why five times, because they just get annoyed. So you have to learn the art of asking five whys.

Drew: Right? Otherwise, you're the little kid: "Why? Dad? Why? Why is this?"

Bob: This is the thing—being dyslexic is the greatest gift I ever got, because it forces me to learn through questions. The only way I could learn anything is through questions. So I was an annoying kid asking 500 questions. But the reality is, that's how I got so good at this, because at some point, as a dyslexic, I only learn by asking people questions. And the reality is, we have all these weird statements around, like, "Don't ask a question you don't know the answer to." That's just idiotic.

Drew: I'm with you there.

Bob: I mean, I appreciate lawyers might not want to do that, because that's their business, but at the same time, we got to ask questions we don't know the answer to. That's the power of this, right? The other thing is, for me, around questions, is I always try to approach every conversation empty, like, as an empty vessel. I don't know their story, and my job is to actually help frame their story, as opposed to, "Oh, they're just like so-and-so," or "Oh my gosh, that's just like somebody else." And you start to realize you end up inferring somebody else's story onto somebody because you're not listening.

Drew: Yeah, I'm listening, by the way, and I'm processing. I know, I know, you know. And the challenge, of course, for some of us like myself is I have to be able to come up with the next question right away as I process what you're saying. The fact that folks aren't listening—I feel like as a young salesperson, I mean, I sold books door to door, and I sold books over the phone, and I actually wrote about this for a foreword for a friend's book recently, where it wasn't until I watched the person who was really, really good at it, who was just expressing empathy throughout every single call that I finally got it. I got off the script, I got into a rhythm, and actually was able to sell enough. And I just feel so much time and energy in marketing, sales, and planning this thing out is "Here's the messaging framework, here's what we're gonna say, and here's how it's structured, and here's how we..." and I wonder if that is kind of a disservice. I mean, yes, you do need to understand how your product is different from your competitors. You do need to understand that, but the way it gets—it gets to be so prescriptive that listening is impossible, because I got a script I got to get through.

Bob: That's why, like, I think a script works in some cases. But the reality is, like, I believe that you should have people who know how to have a conversation.

Drew: Again, my first takeaway on this is you all need to—with your salespeople and your current marketers—you all need improv training.

Bob: Yeah, yeah, that's right. That's one of the things I recommend to almost all the founders. Like, you need improv training because you need to get comfortable again. There's structure to improv. There's structure to how you have to think about it. It's not like handcuffs, where it's just limiting you to say one thing.

Drew: Yeah, we had Matt Abrahams last year on this show, and then he joined us at the Super Huddle. It was amazing, because he's just so gifted at this. He offers a number of frameworks, and once you understand any one of those frameworks, you are ready for whatever question comes your way. And that's right, and what that frees you up to do is to be a better listener. And that's the thing that—

Bob: That's the power of the framework. So I have, I have probably too many frameworks, but the reality is, like, what—so for example, I go into talking to a customer with no questions at all. I just go in with the framework and the forces: what pushed them, right, and ultimately, what outcomes are they seeking? And ultimately, I have to go in with the intent of "I have no idea what it is."

Drew: Right. And I just, I don't see that happening at all. I really think that there's the—we have a series of buckets that we think the answers are going to be, and we're trying to find this match so we can put the Lego, the red Lego, on the red box, and so forth. So that's so interesting—is just this listening with, you know, an open mind and an empty mind. So, all right, fascinating.

Bob: I know that might sound hard to do, but once you've done it, and what I'd say is, I always talk about 1-10-100—once you've done it 10 times, you start to realize that you actually have way better insights. And it's actually to your interest not to go in with all the information. So what was so interesting is like when I started to learn sales, they were trying to tell me everything about the person that I was gonna go meet. I'm like, "I wanna know nothing about them. Know nothing about them." And like, "No, no, you got to know everything about them." I'm like, "No, I don't want to. I'm going to let them tell me." And they're like, "They don't want to tell you." I'm like, "I get it. But the fact is, here's the thing—I'm going to ask them questions, and ultimately the questions will tell me everything I need to know. But if I take the information you gave me, I'm going to make so many assumptions about that information. And most of it is wrong."

Drew: Yeah, the assumptions ruin it all, right? Well, yeah, Bob, thank you for sharing your insights with us before we wrap up. Maybe you could leave the audience with one final thought about embracing demand-side thinking and how that can really transform their approach to both marketing and sales.

Bob: Yep, I think the reality is that people are seeking progress. They're not seeking perfection. And so ultimately, to help them define the progress they're seeking and how your product or service can help them make that progress is what this is all about. And so it's—and progress is that combination of problem and outcome. Progress to them is the combination of those things. And so ultimately, try to frame the progress people are trying to make.

Drew: Frame the progress that people are trying to make. We are not—it's progress, not perfection. I think those are some great places to end. So, and where can people find you?

Bob: Oh, LinkedIn is the best place. I've got a small boutique consulting firm. I do mostly startup product stuff and kind of sales and marketing stuff for startups. And then I teach at Northwestern in the venture creation or entrepreneur school—awesome. So LinkedIn is the best place to get a hold of me if you have any questions. Just LinkedIn, and I'm pretty good about it. You know, typically if you have something really long, I have to listen to it, and so sometimes it's just better to hop on the phone than it is to write me a long note.

Drew: Amazing. All right. Well, Bob, thank you so much for joining us. 

 

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Show Credits

Renegade Marketers Unite is written and directed by Drew Neisser. Hey, that's me! This show is produced by Melissa Caffrey, Laura Parkyn, and Ishar Cuevas. The music is by the amazing Burns Twins and the intro Voice Over is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about B2B branding, CMO Huddles, or my CMO coaching service, check out renegade.com. I'm your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!