March 24, 2022

What B2B CMOs Need to Know About Sales Enablement

For many B2B companies, the sales process is broken yet the solution is remarkably simple. It’s time to treat buyers as collaboration partners instead of targets. Time to approach selling as something you do with a prospect rather than to them. Time to make selling more human and more effective in a world where more qualified leads is not resulting in higher win rates.

Simple, right? But not easy. As laid out in Sales expert Andy Paul’s new book Sell Without Selling Out, it takes true courage to transform the current playbook, but those bold enough to take the leap will see shorter decision cycles and higher win rates, any B2B organization’s dream.

In this episode, Andy shares how marketers are uniquely poised to enable sales teams through insights into buyer behavior—introducing a new way of selling that ditches “salesy” to make way for connection, curiosity, understanding, and generosity. Don’t miss it!

What You’ll Learn in This Episode

  • The problem with B2B selling today
  • How marketing can improve the buyer experience (and increase win rates)
  • How CMOs can build trust with their CRO

Renegade Marketers Unite, Episode 285 on YouTube

Resources Mentioned

Time-Stamped Highlights

  • [0:00] Cold Open: Airing the CMO Huddles Bonus Huddle
  • [1:35] The Problem with “Acceptable” Win Rates
  • [6:46] How Marketers Can Help Fix the Buying Process
  • [13:27] How to Increase the B2B Buyer’s ROI
  • [15:41] Will Self-Serve Replace Sales?
  • [19:09] The Marketing Insights Sales Need to Achieve Higher Close Rates
  • [22:07] How Marketers Can Help Put an End to “Salesy”
  • [26:49] The Four Pillars of Selling In and Building Trust with Your CRO
  • [33:24] Herbert Simon’s Theory of Bounded Rationality and “The Good Enough Decision”
  • [36:48] Final Thoughts: A New Approach to Sales

Transcript Highlights: Drew Neisser in conversation with Andy Paul

[0:00] Cold Open: Airing the CMO Huddles Bonus Huddle

Drew Neisser: Hello, Renegade Marketers! Today’s show comes from a Bonus Huddle, those are specially curated huddles that we run once a month with experts sharing their insights into the topics that are most important to our huddlers.

The expert at this particular huddle was Andy Paul, a great friend and one of the leading Sales Enablement authorities in the country who recently released this new book—Sell Without Selling Out—which I can’t recommend enough.

Even as a marketer, I think it’s just essential that you understand what may become a really new approach to selling. He joined to share his insights on how he sees the sales process being broken, and how marketers can play a role.

Here’s the secret: Selling isn’t about increasing lead volume, it’s about increasing win rate, and all the things that marketing can do with the insights they have into buyer behavior can make selling more human and more effective.

So many insights in this episode; I can’t wait for you to hear it. Let me know what you think.

[1:35] The Problem with “Acceptable” Win Rates

“Can you really say that you've achieved product-market fit if you can only win one out of five or one of the four of your most qualified opportunities?” —@RealAndyPaul Share on X

Drew Neisser: Hello, huddlers! And welcome to what we’re going to call “March Sweetness” as we focus an entire month of huddles on building sweet relationships with sales. Our special guest today is Andy Paul.

Andy is the host of a top-rated podcast called Sales Enablement with Andy Paul and the author of a terrific new book—and I know you know I use that word a lot, but I actually read this book, it’s called Sell Without Selling Out, on a beach on my phone because the hardcopy wasn’t available. I found myself highlighting it like almost every chapter, bunch of things on it.

Andy is, as I mentioned, an expert on sales, having been a salesperson himself. But I’ve had the pleasure of knowing him for several years now and I really appreciate his thoughtful interviewing style.

He actually reads every book of the people he interviews, and he’s recorded over 1,000 episodes. I’m delighted to turn the tables on Andy and throw questions his way. So, Andy Paul, welcome!

Andy Paul: Thank you, Drew. Thanks very much.

Drew Neisser: Excited. We’re going to get to your book which, as I already mentioned, I did read. And I highly recommend this book to humans of all kinds, not just the species that are known to have “sales” in their titles.

But I want to stay broad for a moment. We know that sales and marketing need to be connected at the hip, but a lot of times they’re not. I want to channel all of those sales leaders that you’ve interviewed, and it’s so many, who aren’t aligned with marketing.

You hear that and you could just tell there’s issues that they have. Maybe we could run down what you hear as the typical complaints that a CRO or head of sales might have with marketing. Run them down, and then we’ll go through them one at a time and take it from there.

Andy Paul: You know, I have—this might not surprise you, but I have sort of a contrarian view of that whole thing.

Drew Neisser: Okay!

Andy Paul: Which is that sellers are basically looking for marketers to save them from themselves.

Drew Neisser: Okay. What does that mean?

Andy Paul: Well, they want marketing to help them make up from the fact that on balance—and I think this is a trend that exists in many industries, not just in the software world—is save them from what I consider abnormally low win rates and their inability to win a sufficient percentage of the qualified opportunities they have.

And so, in the absence of being able to be more effective selling, they just want more volume of leads. And if they can’t get more volume of leads, then they’re going to b*tch.

Drew Neisser: This is something I know, and I heard you in the interview that you did on your podcast on your book, you talk about win rates being what is considered an acceptable win rate in many industries versus what you think an acceptable win rate is. Can you just talk about that? Because that’s what it comes down to, right?

Andy Paul: Right. So, I mean it varies, obviously, by industry. But even within industries, I mean, oftentimes in the SaaS world, and I know firsthand experience working with a number of SaaS companies, you know, they find an acceptable win rate of their most qualified opportunities at the start of a period that they might win 20% or 25% of those. That’s considered pretty typical.

Drew Neisser: 20%, so one out of five. So, that would be from a pipeline—and we talk about this and huddles a lot—so, what’s your remit? That might be 3x or 5x per sales rep. The premise right here is, if you deliver 5x we’ll be able to close one in five, and we’ll be able to…

Andy Paul: Yeah, here’s a rule of thumb to think about. Your win rate will be the reciprocal of your pipeline coverage requirement.

Drew Neisser: Okay, you’ve got to explain that to me.

Andy Paul: Well, if you have a 5x pipeline coverage requirement, your win rate is most likely going to be 20%. One of every five.

Drew Neisser: Because if they only had one lead, they’d have to close it.

Andy Paul: Yeah. So, if you find that if you’ve got a 9x coverage—as some companies do—or 7x, their win rates are going to drop below 20%… And I would ask the question of anybody who says, “Well, hey, we’ve achieved product-market fit…”

Can you really say that you’ve achieved product-market fit if you can only win one out of five or one of the four of your most qualified opportunities?

Drew Neisser: It’s interesting because this thing got switched really fast to sales not being able to do their jobs. And I know that a lot of CMOs would like to say, “Well, sales isn’t very good at what they do because they only close one in five.”

I think if we step back to your first statement: Sellers are looking for marketing to save themselves from themselves… So, in other words, if marketing was just better, then sales would be easier. Is that the framework for this?

Andy Paul: No, I think that if you’re in that situation where you have such low win rates, somewhere there’s a failure along the line, right? Could be a failure to appropriately qualify the prospect. You know, they just may not be a fit, right? Could be a failure to do appropriate discovery.

What I talk about in my book is to really understand what’s most important to the buyer. Or what is I think happening most frequently is that the experience the sellers are creating for the buyer in their buying journey is one that does not either inspire or activate the interest sufficiently of the buyer to make the decision to buy from them.

[6:46] How Marketers Can Help Fix the Buying Process

“The majority of the purchase decision is based on the buyer's assessment of their interaction with the seller more so than the product that they're buying or the company they're buying it from.” —@RealAndyPaul Share on X

Drew Neisser: So, the sales process—one in five or one and nine or whatever it is—is flawed or broken or something. Now, I’m thinking about the CMO for a moment. And I know that they can’t go to their sales guy and say…

Andy Paul: You suck.

Drew Neisser: “Dude, you suck.” That’s pretty certain. You can’t build a relationship this way. I’m wondering, as we think about this problem, which is inherent as you’re describing it, there are some failures in the sales process. And part of it, I guess, would be helping them to identify it.

But what would you have the marketers here do to… You know, they’re putting the leads into the pipeline in theory, and they’re even sales qualified leads or they’re opportunities. They’re real, they’re not just stopping it at marketing qualified leads.

What would you have them do or know or understand—those are a lot of different verbs, so let’s get into this from, again, this broad level, and then we’ll talk about how to fix sales.

Andy Paul: I think it starts from understanding why the buyers buy from the seller, right? We know from research from Challenger and Gartner and Forrester that the majority of the purchase decision is based on the buyer’s assessment of their interaction with the seller more so than the product that they’re buying or the company they’re buying it from.

You really need to understand and be able to quantify, to some degree, what is that experience buyers are having with your sellers? This is different than a win/loss analysis where you don’t have pricing and product and features. This has to do with that experience dealing with the sellers.

The fact is, most organizations are completely, you know, have no knowledge of what the buyer’s perception of that is. And it’s decisive, the decision they ultimately make, so I think one thing marketing can help with is say, “Yeah, let’s start looking at that.”

When I talk to sales leaders and they talk about, “Hey, we need to hire some people. Hire up some people. And these are the skills and attributes we need…” I’ll say, “Well, have you ever asked your buyer what they need from your sellers? What they need your sellers to be? Do they need to be an extrovert? Do they need to be a closer? Do they need to be all these attributes of sales leaders typically put on the job descriptions?”

The fact is, no, what buyers need is—what I summarize—they need curious, open-minded problem solvers. But I think marketing could help sales by saying, “Yeah, we’re going to go out and we’re going to talk to our buyers on a regular basis and create sort of like an NPS equivalent for how the buyers experience the sales process as their buying journey.”

And if we’re completely unmindful of them, how can we make decisions about how to improve our processes or sometimes even the opportunities we’re targeting?

Drew Neisser: I’m going to put a big punctuation point on that because this is a different way of thinking about—so buyer NPS, just focusing on that for a second. I don’t know too many companies, you know, if you do this at your company, put it in chat, but I don’t think there are that many who actually—in a sense, your kind of rating that salesperson and the experience that they’re delivering.

Andy Paul: Well, it’s… yeah! As I like to say, it is personal. It’s not personal as in you’re a bad person, but it’s personal as in the buyer is making a judgment about you and the value you brought to them to help them make their decision. So yeah, there are very few companies that do that.

There’s a company out of Austria, Vienna called Alinea Partners, like the famous restaurant Chicago, Alinea, run by a woman named Leahanne Hobson. Actually, if anyone wants to tune in to my podcast, Leahanne’s actually on my podcast where we talk about this. I read about the company, and I thought, this is fascinating. This is what they do. They work with companies like Microsoft and others to be able to assess and quantify what that buying experience is with sellers.

Drew Neisser: You know, it’s so interesting because it’s not like the CMOs here don’t talk to customers. They talk to customers all the time, but when they’re doing it, what they’re listening for is messaging and an insight that they can use to create campaigns or to get case histories and find ways of, if you will, using this customer to get another customer based on that. But they’re not generally trained to assess a sales experience.

Andy Paul: Yeah, or a buying experience is what I’d call it—

Drew Neisser: Or a buying experience, right.

Andy Paul: So, yeah, I think that’s a function marketing could take on. And it’s necessary.

Drew Neisser: And what are some of the questions and things—what do we include in this? Let’s write this thing right here.

Andy Paul: Why not? I should bring Leahanne Hobson on to talk about it.

Well, I think you can start with identifying… Start with this larger premise: What value did you get from the sellers? So, we know that from various surveys that 80% of—and I have this in my book—80% of C-Level decision-makers say they see no value in their interactions with sellers. That’s a pretty significant amount, right?

Start with that. We want to dig down on that, right? What was missing? Why wasn’t there value in this interaction? What were you expecting that you weren’t getting? What do you need from the sellers that, you know, at various points in time… because I think the other thing that goes along with this is that we’re completely misaligned from a selling standpoint with the buyer and their journey, right?

We still map out the sales journey as these linear stage-based processes that fit neatly into our CRM system, and they have no relevance whatsoever to what the buyer is going through.

Drew Neisser: Yeah, we’ve seen the Gartner spaghetti chart.

Andy Paul: Right! The spaghetti chart, right. So, at the heart, there are these four jobs that need to be accomplished.

Drew Neisser: Yeah.

Andy Paul: So, I would hope that we could do through assessing how the buyers experience this is we start getting data to start aligning this, right? When we have these various touchpoints and we understand the expectations the buyers have from sellers at those touchpoints, we can say, “Okay, we can do a better job.”

In the book, I’d simplify it for people to make it easier to understand that, to say, “What is value in the context of a buyer?”

What I argue and I believe is the value is, in the sales process, value is progress, right? So as a result of interacting with the seller, did I make progress toward making a decision? That becomes the benchmark for every interaction you have with the buyer, was I able to enable the buyer to make progress toward making a decision.

That’s another area I think as we identify with these touchpoints and the lack of value that they receive from them, then marketing can work with sales to say, “Yeah, how can we better enable the sellers at these points in time to be able to help the buyer make progress?”

Drew Neisser: I want to go back to that number of 80%—are these people who actually purchased? So, these are people at the end of the thing who purchase or this is in general of all buying experiences, B2B buying experiences…

Andy Paul: I believe it was a Gartner study that was done. I have the reference in my book, I forget the exact number or exact nature of the study, yeah.

Drew Neisser: And value is progress.

[13:27] How to Increase the B2B Buyer’s ROI

“Every time you interact with the buyer, they're investing time and attention. They have to earn a return on that investment.” —@RealAndyPaul Share on X

Drew Neisser: So, to me, that gets us to sales enablement language and thinking about the tools that you can do if it’s the ROI calculator or some of these other things. But you’re shaking your head, what are we talking about when we say, “helping them make progress?”

Andy Paul: Yeah. Think about the basic bargain that buyers strike with a seller: “I’m going to invest some of my time and attention in you. What am I going to earn in return for that investment?”

It’s that simple. So, every time you interact with the buyer, they’re investing time and attention. They have to earn a return on that investment. A lot of what they want, I believe, and my experience has shown that they want the help of a sales organization, a selling organization, to think more deeply and broadly about the problems they’re trying to solve and more deeply and broadly about the outcomes they potentially can achieve.

I think that, again, is another area where sales needs help. There’s a thin stratum of really good salespeople that can do those things independently. But then there’s the rest that are engaged in that.

So, let’s take aside the top 5% maybe that are capable of having those discussions, have the insight and experience, and have learned and brought it all together. But then we’ve got the rest of the 95% of sellers that need help.

I think that help comes in part from marketing that can help them really understand how their existing customers are getting value from the products that they bought from you—products and services.

And especially, I think a question that doesn’t get asked enough when we do case studies and so on is—my experience has shown over 40+ years at this point is that on almost every instance, when I sold something, the buyer is deriving some value from it that they didn’t anticipate when they made their purchase decision. Some feature or function or use case that’s developed through their use of it that they didn’t anticipate.

It’s understanding those things, those become the valuable insights for sellers as they start to engage with buyers. Because then, in my book I talk about six different types of questions, you ask one of those being an insight question.

The insight question is you’re going to ask a buyer something about their business that you could reasonably expect them to know, but possibly they don’t. So, it becomes this great conversation trigger for beginning to explore with the buyer what the problems are and what they possibly hoped to achieve.

[15:41] Will Self-Serve Replace Sales?

“They really need people with weak ties to the organization, as in salespeople, to come in and help provide a different perspective about the problems they're trying to solve.” —@RealAndyPaul Share on X

Drew Neisser: That’s a lot to unpack. I’m going to get through some of those, but I want to just go take a quick detour back. So, if 80% of the buying experiences suck and in sort of no value determined, and we already have this trend towards self-serve because we’re all pretty satisfied with the self-serve thing.

We go to Amazon, we buy, we hit the button, we do our research, and we’re done. Is part of this just doing a better job of trying to self-serve and anticipate this so that when you finally do have a sales conversation, you can really get to value add? Is that a concurrent solution?

Andy Paul: Yeah, I mean, I’m a little skeptical of the research that’s come out that says buyers don’t want to talk to sellers and so on. Because, you know, I think maybe over the course of commerce and human history, let’s say 6000 years, buyers never wanted to talk to a seller.

You know, I never had a buyer wake up in the morning say, “Gee, I wish Andy calls me today.” No, the same buyer still has the same imperative which is, they get to a certain point, they need to talk to salespeople if the salespeople can add value to them, right?

The salespeople are better than looking at a website or downloading a piece of content, which is a pretty low bar, right? Plus, there’s the element of risk associated with purchase decisions that carry risk. People want to validate decisions with talking to humans.

I believe that the way to think about it is that—and I think self-aware organizations know this—it’s, you know, this whole idea of strong ties and weak ties. The research on that is: People work together in an organization, they develop these strong ties, and what the research has shown is that basically they close themselves off to outside input.

So, the information they know is called redundant information. They really need people with weak ties to the organization, as in salespeople, to come in and help provide a different perspective about the problems they’re trying to solve.

I believe self-aware buying organizations know this intuitively, right? We need an outside perspective on what we’re trying to do, so that then becomes an opportunity for them to engage with sellers.

If we continue down the path I think we are on, yeah, we’re creating an impetus for buyers to say, “How much more of this can I do on my own because I’m getting no value from talking to these salespeople?”

So we, as sellers, can be better which is what I argue in the book and I think there’s a path to do it. But we’re not helping ourselves right now.

Take this case where we have 7x—even 5x or 7x pipeline coverage requirements. You can’t expect sellers to devote sufficient attention to all the deals in the appropriate way in order to bring them across the finish line, to help the buyer make a decision. What we’d end up with this scenario is where we’ve got so much deal flow in many cases coming through the funnel, that instead of selling, we’re basically playing the odds.

We know that if we just do a minimally good job, we’re going to close a certain percentage of those. And I’ve had this conversation with CROs of public companies where I talk to them about their growth strategy and there’s no focus at all improving sales effectiveness.

It’s all about, we’re pretty good at getting that demand gen and lead gen and getting opportunities into the top of the funnel. We’re going to invest heavily in that because we’re good at it, we think it can get better, and we know if we just close this low percentage of it, we’ll still be able to grow and hit our targets.

Someday the party ends though, with that. No one is selling in markets with infinite TAM that enable you to do that forever.

Drew Neisser: Again, I have many questions going through my mind here.

Andy Paul: Is this not going the way you wanted?

Drew Neisser: No, it’s going great. And it’s so fascinating.

[19:09] The Marketing Insights Sales Need to Achieve Higher Close Rates

“If you collaborate with the buyer to help them reach a decision, then that's much more effective and it results in shorter decision cycles and higher win rates.” —@RealAndyPaul Share on X

Drew Neisser: One question is: The training of the sales organization and the role that marketing plays in that. Because in theory, in many ways, marketing was the repository of all great insights into the customer.

Andy Paul: Right.

Drew Neisser: Whether or not that exists universally or not, that was always a core strength of the CMO. Here’s the other thing, if most of these companies have a 5x pipeline and you’re arguing that’s bad, most of the CMOs have come to live with that. Which means they’re not providing insights today that are helping the CROs close at a higher rate. Is that fair? Did I connect dots that are connectable here?

Andy Paul: Possibly. Yeah, in some cases, yeah, I believe that’s the case. Yes.

Drew Neisser: So, then we can then go to this question of, if CMOs aren’t delivering the insights the salespeople can use to close at a higher rate, what do they need to do to get those insights? What are the things they should be thinking about?

Maybe we need to go through the six different questions. You know, do they need to go on more sales calls? Are they listening into Gong? I mean, what is it that they need to do to make sure that they have this understanding so that they can deliver the insights that will get us to 3x? Which feels like one in three should be a reasonable thing because then you can put more energy into it, right? More time, deliver more value.

Andy Paul: Yeah. Yes. It starts with the—think about it that really starts with—and marketing doesn’t—maybe has some role in this, I don’t know… is how to give sellers what their job is. And I think marketing does help with this somewhat.

This gets into the topic you want to talk later about persuasion versus influence. If you ask most sellers, which I’ve done, public speaking, I ask people raise their hands and we do anecdotal surveys… But the vast majority of sellers think their job is to go out and persuade a buyer to buy their product.

I believe the job of a seller is to go out and listen to the buyer, to understand what’s the most important things to the buyer in terms of challenges they face and the outcomes they want achieve, and then help them get that.

Now these are two different ways of looking at the world. One is, you’re a target and my job is to make you buy what I’m selling. The other one is, let’s really understand what’s important to you and how can we help you achieve that?

Drew Neisser: You use the word influence instead of persuade.

Andy Paul: So yeah, I think marketing can help in that degree as well. We have to change this perspective—the operating perspective that most sellers have, most sales leaders have [where they] think that the buyer is a target.

Selling is something we do at someone and something we do to someone, not something we do with them. I speak from the experience of selling everything from $2,000 computer systems to $150 million communication systems.

It works the same in all instances. If you collaborate with the buyer to help them reach a decision, then that’s much more effective and it results in shorter decision cycles and higher win rates.

Drew Neisser: It sounds so easy.

Andy Paul: Well, it’s not. It’s simple, not easy.

Drew Neisser: Okay. It’s simple, not easy.

[22:07] How Marketers Can Help Put an End to “Salesy”

“As humans, we universally resist being persuaded.” —@RealAndyPaul Share on X

Drew Neisser: So, there are so many good chapters in just the titles alone in your book. Chapter Five is “Death to Salesy.” Why does salesy need to die and how can marketers help here?

Andy Paul: Yeah, so salesy is those legacy, obsolete sales behaviors that buyers hate that are legendary. The self-interested, pushy, persuasive, sleazy sales behaviors as they’re perceived by the buyers. I find it interesting that we know these things don’t work. They’ve never worked.

They don’t have any value for the buyer. They have no value for us as sellers, so why don’t we just stop? We could stop today. We can go cold turkey today with those salesy behaviors, and we’d be no worse off than we are today.

So, getting back to the persuasion thing—and I referenced in the book this book by Jonah Berger, The Catalyst, a professor from Wharton, who wrote a book about persuasion, and I had him on my show.

We didn’t agree about everything that we talked about, but he has this research he cites in the book that shows that, as humans, we universally resist being persuaded. It’s like, we know this, and yet we fashion so much of our sales training and sales theology if you will around this idea of persuading people to do something. It’s just sort of counterproductive in most instances.

Back to the idea about the sales, just to wrap that up is, we’re teaching people to be salesy. The story, it’s in the book, but it’s one I love to use: The one question a buyer will never ask you, which is, “Hey Drew, I love your product. But I just don’t think I can buy from you because you’re not salesy enough. Could you be more salesy?”

Drew Neisser: Yeah, I could. Yeah.

Andy Paul: Right. It just has no value for anybody in the equation. And yet, it really dominates over the sales culture these days.

Drew Neisser: Yeah, I mean, anytime we talk about this, I just immediately go to the movie “Used Cars,” and I think of the scene where the competition is who can sell it the fastest. The one, I think it’s Kurt Russell, goes up and says as someone has just touched the car, arrived in the lot, and says, “So can we write it up?”

That’s not what we’re doing here. But I feel like part of this interesting conversation is, the CRO will have to say, “Oh, 5x isn’t good enough. Oh, we should be going for 3x.” They’re going to have to identify these series and have to agree with the CMO.

Because the CMO can probably find that insight. They’re all trained. I mean, they’re really good at finding insights that will help and think about this a little bit more. But at some point, the CRO has to say, “You’re right, it’s a problem.”

Andy Paul: Right. That is the problem. In so many instances, it’s the playbook that’s become the institutionalized playbook certainly in the software world because this is how we do things.

So, if you’re a CRO coming into a new situation and you’re thinking about job longevity in any sense of the word, are you going to take a risk to try to change things up? Or are you just going to say, “Well, I’m just going to try to do better at the crap we’re doing as opposed to trying to really transform things.”

Because what leeway do they have? It takes somebody with some courage to go back to the board and CEO and say, “Yeah, I know, you just brought me on, but we’re going to change things up. We’re going to have a down quarter, maybe two, but then the future is going much brighter.”

I’ve seen and come across very few CROs that are willing to have those conversations.

Drew Neisser: Interesting. In some ways, let’s face it, if the CMO can get the salespeople to close at a higher rate…

Andy Paul: Can help them do that, yes.

Drew Neisser: If they can do that, that opens up a lot of other things, right? It creates all sorts of opportunities to put more money in retention activities, more money in upselling and cross-selling, more money in other ways of improving the experience or just, like, brand or other things that would, again, in theory, help close at a higher rate.

The interest is there to do that. I don’t see that happening as the request, I don’t think CMOs are being told that.

Andy Paul: No.

Drew Neisser: It’s, “You’ve got to deliver 5x. Just get 5x. We’ll close from there. We’ll take it from here.”

Andy Paul: “We’ll take from here.” Yeah.

Drew Neisser: But I will say in fairness, there’s a lot of Brent Adamson believers who are big on buyer enablement and are doing and thinking about it all the way through and also look at close rates and speed to close.

I mean, one of the CMOs on this call, we’ve had an in-depth conversation about how they’ve worked to speed up the sales cycle, which means if they’re speeding up the sales cycle, they must be doing some things that you’re describing.

[26:49] The Four Pillars of Selling In and Building Trust with Your CRO

“We are wired to want to connect other people. We are wired to be curious. It's our curiosity that enables us to navigate the world around us.” —@RealAndyPaul Share on X

Drew Neisser: I think we can step back and make this really interesting in the sense that all of us are doing sales one way or another.

Andy Paul: Right.

Drew Neisser: Right. And one of the sales jobs that—the assignment now for all the CMOs here will be to sell their CRO on or to influence their CRO on creating more value throughout the sales process. So, in your book, you talk about the four points—you have a four points framework, which you know I’m a fan of because…

Andy Paul: The four pillars of selling in.

Drew Neisser: The four pillars of selling in. Now the book is called Sell Without Selling Out and the goal is to be selling in, not selling out. So, let’s take these four pillars. We’ve got connection, curiosity, understanding, and generosity.

Andy Paul: Right.

Drew Neisser: And we’re all, in our role as salespeople, as influencers, are going to take these four characteristics. Let’s talk about connection first and what do you mean by that? What are we going to learn to do?

Andy Paul: Sure. Well, just as a sort of step back and framework, actually, when I was starting to write this book it was originally framed as a little bit bigger book talking about using these same frameworks in collaboration within the workplace, right?

I don’t know if anyone’s read Ann Latham’s book, The Power of Clarity. Great book talking about, yeah, collaboration and productivity within the workplace. But she takes what we have known as knowledge workers, and said, “Yeah, we need to reframe that. Actually, they’re all interaction workers because we get our job done by interacting with other people and through other people.”

So, I originally started thinking of it as a broader framework, but we decided to leave that for later, we’ll come back to that. But in the meantime, it’s about sales.

So, the four pillars of connections, first pillar is: In order to earn the right to influence the thinking of someone else is you have to earn a certain level of trust and credibility with that person. That is the first pillar. How do I demonstrate that I’m trustworthy, that I have credibility, that we just have this basic human connection, that I’m interested in you and what you’re interested in?

When you do that, then, you look at it from a sales perspective, also from a collaborative perspective, people start giving you permission to have an influence over them.

Drew Neisser: And these connections, I mean, the word is fairly straightforward. But do you have an example? Again, I’m now thinking of a CMO trying to build a stronger connection with their salesperson specifically to influence them to change the way they sell.

Andy Paul: Yeah, so it’s pretty well known that one of the keys to building trust is some level of vulnerability, making yourself vulnerable, not in the emotional, “Hey, I’m going to bare my soul to you” type vulnerability, but in the context of, “I’m going to take a little bit of a risk.”

When you’re dealing with someone—I created another four-point framework that you didn’t mention, a second one called MICE, and these are a four-point framework for building trust with someone. The M stands for Motivations. Are your motivations transparent when you’re dealing with someone? This is the key thing, right? Just on the surface, yeah, I’m completely transparent about why I’m talking to you, what my objective is, what I’m trying to achieve.

The I is Integrity, meaning: Having said this is what being transparent and my motivations are, do my actions align with my words? Or the famous Emerson statement, what you do speaks so loudly I cannot hear what you say. Actions speak louder than words.

The C stands for Credibility: Have you established a baseline of credibility around a topic you’re discussing or interacting on.

And the E is Execution: Do you live up to your commitments? So motivations, integrity, credibility, execution.

It’s a simple framework for dealing with someone and you’re trying to do that with your counterparts. We’ll broaden this a little bit into the other pillars, but this is just a baseline, right? If you can meet this, then they open themselves up to say, “Okay, I want to learn more.”

Drew Neisser: Okay. Curiosity…

Andy Paul: Curiosity. Well, just to draw a broader contrast with this whole selling out is, you know, selling out as talked about in the book, those are learned behaviors. No one pops out as an infant pushy, persuasive, sleazy, whatever, maybe a little demanding, but not pushy.

Whereas we talked about connection, curiosity, understanding, generosity—these are innate human behaviors. We are wired to want to connect other people. We are wired to be curious. It’s our curiosity that enables us to navigate the world around us.

In this instance, though, we’re going to using curiosity to begin the process of understanding what’s most important to someone else. And in the book, I talked about six different types of questions.

We talked about the Insight question before, you know, my favorites I talk about in the book is what I call an Impact question. And it’s just a way to get people to start thinking in real terms about what’s the impact of making a decision. In real terms. Start quantifying and not in dollars and cents because you’re dealing with a colleague, but what is what is the impact on you?

Everything that you’re asking them to do has an impact on them, and to merely understand what’s important to them, you need to understand what these impacts are. The other important thing about curiosity is that the way you make yourself interesting to another person is to be interested in them and to serve the basic law of human nature.

Drew Neisser: What you are talking about in your book is being a human being, and there’s this notion when you become sales, you become a salesperson, it’s like an alter ego. It’s this character that you’re playing. I just think it’s so interesting, and I’m wondering if, salespeople who’ve been doing this a long time, do you find they sort of say, “Are you serious?”

Andy Paul: Not so much. It’s actually, the questions we get more tend to be from management level people saying, “Well, we’ve got a number to hit. How can we be human if we’ve got a number to hit?”

And I’m like, “Well, actually, this is how you hit your number more reliably and predictably by being a human because you can actually help the customer come to a decision point more quickly than if you’re just push, push, pushing.”

I have a hard time getting them… because they think you have to—they’ve bought into the act that they think you have to be. And you don’t.

Drew Neisser: Well, it’s funny, because in many ways, marketing could benefit from being more human too in terms of the way it communicates out into the world in, you know, particularly when it gets into speeds and feeds and benefits and insights.

[33:24] Herbert Simon’s Theory of Bounded Rationality and “The Good Enough Decision”

“If you're the first to be able to connect with the buyer and build trust, then you'll be the first to earn the right to influence their decisions.” —@RealAndyPaul Share on X

Drew Neisser: There is an opportunity, equal opportunity, for increased humanity. But it goes back to a question earlier, a question of rational versus emotional and how sales are. Do you have a perspective on, is the buying decision ultimately more rational or emotional? And what role does sales play in that?

Andy Paul: Yeah, so I talk about that at the end of the book… Again, a little bit contrarian, I think, but it’s based on hard science—it’s that at the end of the day, buyers make a pretty rational decision.

The background of this is that people familiar with Herbert Simon, Nobel Prize-winning economist on a bunch of research on what he called The Theory of Bounded Rationality.

And he said that when people make decisions, everyone has three constraints: Limited-time, limited information, limited understanding. And therefore, when they’re out looking to make a decision about something, people typically will research their alternatives until they find a solution that satisfies the requirements and suffices to meet their goals.

He created this word, a new word, called “satisfice.” Now, that was on one end of the spectrum, the other end of the spectrum was what they called Maximizers. Maximizers are people that will evaluate every single alternative to ensure themselves that they made the absolute best choice.

What Simon found is that what Satisficers did is make what we call “The Good Enough Decision.” The first time this happened to me in my career, I was just confused. A big system, this telecom company in Europe, and like about two months before I thought I was gonna get the order, I got the order.

What happens is, buyers say, “Look, the differences between, especially these days, products are so slim that the marginal gain we’ll get from investing more of our time to keep investing in evaluating alternatives just isn’t there. This is good enough.” Boom.

And so, when you think about how you then structure your selling process, these pillars start becoming very important because if you’re the first to be able to connect with the buyer and build trust, then you’ll be the first to earn the right to influence their decisions.

You’ll be the first to reach a level of understanding about what’s most important to them. You’ll be the first to help shape this vision of success for them and what success will look like if they’ve invested in using your product and service, which Forrester found in a study about 10 years ago that if you are the vendor that’s first to be able to do that, your odds of winning a deal stand at 65%. There’s a study that they did on IT buyers, must have been roughly about 10 years ago.

So being focused on making connection, building trust, demonstrating trustworthiness, demonstrating and deploying your curiosity, reaching this level of understanding, doing these things—if you’re the first to get there, huge benefits from you from a sales perspective in terms of your odds of winning a deal.

This becomes much more powerful than even the product and service you’re selling. I relayed stories in the book—I worked for startups for a number of years selling large complex communication systems, competing against the biggest tech companies of the day, big defense systems integrators, and so on. And we want deal after deal because the buyer would say to us, “You’re the only ones that made us feel understood.”

Drew Neisser: The only ones that made us feel understood. There it is. It’s all you got to do. That’s all you got to do now.

[36:48] Final Thoughts: A New Approach to Sales

“If practice makes perfect and you're only closing one of every four or one of every five or your deals, what are we training our sellers to do? We're training them to lose.” —@RealAndyPaul Share on X

Drew Neisser: We’re running out of time here and I picked up a lot here, which is so interesting in all of this, which is, there’s a landmine out there, which is that sales is broken. Sales perspective is a little bit broken.

There is a way for you to defuse the landmine in a way that is good for you. Really good for you, the CMO. And part of it is helping them develop an approach to sales that will increase the close rate, which means either you need fewer people, which is part one of the thing.

You may need fewer people or you grow faster, but getting there is going to take some work and some mutual understanding and some influence. And a recognition. Somehow or other the CRO has to say, “The way I’ve been doing it is broken.” This is not an easy conversation, but hopefully a lot of food for thought.

As you think about CMOs leaving this call, is there anything else that you would like them to leave with to help them inspire a new approach to sales beyond some of the things that we’ve already talked about?

Andy Paul: I think it’s just a discussion that needs to be had. We’re just in a vicious circle, I think, at so many companies because they think that this is a playbook that we have to implement. And the playbook is fundamentally broken.

It works for companies who hit a moment in time that, yeah, they do have that magical moment of the right place at the right time. What people have done is attributed those companies’ success to their sales process as opposed to the fact is the right product for the right market at the right time.

This is a hard thing to break, but I think it starts with conversations at the executive level to say, “Look, we need to refashion what we’re doing. Our path to growth doesn’t have to come from just doing more of what we’ve been doing but doing better at what we’re doing.”

Because if companies could take win rates from 20s one year to 30 the next year, 35 the year after, and so on, trust me, it’s a faster, more profitable route to growth than what they’re currently doing.

Drew Neisser: And it’s much more fun. I mean, who wants to fail…

Andy Paul: And more fun. The thing is, that’s another point. I know it’s not the theme for here today, but yeah, I mean, there was a study that came out from toward the tail end of last year about the mental well-being of salespeople. And not good. The picture wasn’t pretty. But a lot of it is because they’re off in these environments where what’s considered acceptable is not good.

Drew Neisser: Yeah, it’s 80% failure rate—

Andy Paul: Right, and so if practice makes perfect and you’re only closing one of every four or one of every five or your deals, what are we training our sellers to do? We’re training them to lose.

Drew Neisser: It’s so interesting. And I imagine, because this would be a huge leap for folks. What I’m thinking about is, in theory, this is a testable proposition. You could create a skunkworks of salespeople with your CRO to say, “This group is going to try a different approach.”

And their goal is to get from whatever… If we’re one in five, we’re going to get to one and four, and here’s how we’re going to do it. You could actually create a test with a partner.

All right, well, we’re out of time. But, Andy Paul, thank you for joining us. Where can people find you?

Andy Paul: Can I flash my book?

Drew Neisser: Oh, look! Yes please! Mine hasn’t arrived by the way, and I pre-ordered it.

Andy Paul: So, Sell Without Selling Out. Number one new release in multiple categories. Best Seller on Amazon after a week. It’s the moment for the book. Clearly, there’s a willing audience of people who want to say, “Look, help us change what we’re doing.” Amazon, wherever you want to buy it.

People who want to follow me on LinkedIn, I’m pretty active on there. My podcast is “Sales Enablement with Andy Paul.” We’ve done 1,036 episodes. And yeah, go to We have a little assessment there—a little fun assessment you can determine how sales-y you are.

Drew Neisser: Okay, all right.

Andy Paul: Not hugely scientific, but it is fun.

Drew Neisser: All right, thank you, by the way.

Andy Paul: Thank you. It’s been a lot of fun.

Show Credits

Renegade Marketers Unite is written and directed by Drew Neisser. Audio production is by Sam Beck. The show notes are written by Melissa Caffrey. The music is by the amazing Burns Twins and the intro voiceover is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about quite possibly the best B2B marketing agency in New York City, visit And until next time, keep those Renegade Thinking Caps on and strong.