Burn The Playbook - B2B GTM Strategies with Marc Crosby

Gap Prospecting 2026: Intrigue, Interest, and Outbound That Works With Keenan

• Digital Rebels Consulting - Marc Crosby

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Gap Prospecting that gets replies. Keenan breaks down problem-centric outbound, the Problem Identification Chart, and how to write messages that create intrigue and interest. If you’re stuck in activity theater, this flips the script. Keenan is the CEO of A Sales Growth Company, a Forbes Top 50 Social Seller, and one of the most cited sales experts in the world. He wrote Not Taught and the bestselling Gap Selling, with his new book Gap Prospecting dropping in 2026. His firm was also named a Representative Vendor in the 2025 Gartner® Market Guide for Sales Training Service Providers, Worldwide.

What you’ll learn

  • Who Gap Prospecting is for and why now
  • Problem-centric selling vs product-centric habits
  • The three-layer enablement model: skills, opportunity, forecast
  • How to run a great discovery without scripts
  • The Problem Identification Chart: problems, impacts, root causes
  • Symptoms vs catalysts and how to spot them
  • Intrigue→Interest: writing emails buyers answer
  • Where AI helps prospecting…and where it makes it worse
  • Burn it or build it: rapid takes on quotas, video, texting, gifting, breakup emails

Chapters
00:30 Welcome, guest intro
01:05 Who Gap Prospecting is for
02:39 Why a prospecting book now
04:31 Why coauthoring this time
05:25 The Problem-Centric Operating System
10:36 Where companies blow enablement
12:38 What makes discovery questions good
17:16 The Problem Identification Chart (PIC)
22:22 Has this changed since 2020?
23:22 AI and prospecting: help or harm
31:25 Unexpected lessons: symptoms & catalysts
32:42 Burn it or Build it: 10 hot takes
41:32 One contrarian move for Q1 win rate
42:48 Where to find Gap Prospecting info
43:06 Close

Who this helps

  • CROs, VPs Sales, and founders with an outbound motion
  • SDRs, BDRs, and AEs who prospect
  • RevOps and Enablement leaders building repeatable systems
  • Marketers supporting pipeline with outbound signals

Guest

Host

Keywords
gap prospecting, gap selling, problem centric selling, problem identification chart, discovery questions, sales enablement layers, skills layer, opportunity layer, forecasting layer, symptoms and catalysts, intrigue and interest emails, outbound strategy, SDR prospecting, BDR prospecting, AI in sales, breakup emails, video prospecting, multithreading, daily activity quotas, buyer intent

Hashtags
#GapProspecting #GapSelling #Sales #Prospecting #B2B #Outbound #SalesLeadership #BurnThePlaybook #DigitalRebels


gap prospecting; gap selling; keenan; problem centric selling; problem identification chart; PIC; discovery questions; ou

Views expressed are our own and do not represent any organizations

© 2025 Digital Rebels Consulting. All rights reserved.


Digital Rebels Consulting (00:30)
Welcome in I'm Marc Crosby. This is burn the playbook My guest today is Keenan the CEO of a sales growth company a Forbes top 50 social seller and one of the most cited sales experts in the world He's the author of not taught and the best-selling book gap selling with this new book gap prospecting on the way in 2026 today We'll talk about tearing down old sales habits replacing them with problem centric selling and rethinking prospecting So it actually connects with buyers. What's up Keenan?

Keenan (00:57)
How you doing, man? Thanks for having me.

Digital Rebels Consulting (00:59)
Doing well, glad to have you here. So who did you write Gap Prospecting for for 2026?

Keenan (01:05)
Anybody doing outbound. mean, anybody and everybody is responsible for outbound, SDRs, BDRs, full service AEs, in a lot of ways marketing. Anybody responsible for outbound and outbound messaging.

Digital Rebels Consulting (01:17)
Gotcha. Yeah. I was going to ask you if, it more for just salespeople marketing you mentioned? Should CEOs read the book? Should anybody in business read the book? I read a lot of sales books myself and I tend to think that not just salespeople should read some of these things because everybody should be connected in one way or another with that strategy. So would you think it would be good for executive leadership to read this as well?

Keenan (01:37)
Yes to the extent that they have an outbound motion. So gap prospecting is very specific to the outbound motion, very specific. ⁓ If you only got to read one, then read gap selling, because gap selling addresses selling in its entirety. So gap prospecting takes the problem-centric concept of gap selling and shows you how to be a problem-centric prospect or outbounder. ⁓

I guess the medium answer is if you're an executive and you have teams that have to do outbound, then absolutely you should read it. Because I believe that one of the disconnects in the world of senior management gets disconnected from the actual execution. Sorry, guys. I love you, Smart Spuck. But you get up on these little pedestals and you stop understanding how it works. And then you expect your ability to influence how it works is diminished.

because you rely on a person who has to rely on a person to rely on a person, then you guys wonder why you can't execute. for those execs who believe in the concept of, don't have to do it, but I better understand it, prospect is a great one, but gap selling is the one that'll lay the greatest foundation if you can only read one.

Digital Rebels Consulting (02:39)
Understood and so gap prospecting prospecting is obviously not a new concept. So why gap prospecting right now for you for this book?

Keenan (02:46)
Well, I think for a couple of reasons. One, so much has changed in prospecting. The whole idea of one more call and activity-based. I sit down and I say, well, I have these many. I have to make this much money. And my close rate's this. And my convert rate's this. So I'll make these calls and I'll make it. No, no, man.

People don't pick up the phone anymore. ⁓ One of the big observations we made is in an effort to scale, we start focusing on the quality of the messages. We stop focusing on upskilling the capabilities of the team. We just do a shit load of tools in their hands. Outreach, sales loft, like zoom info, like all this stuff. And they're just pounding buyers. You know, we start the book with when I started cold calling in the nineties, I mean,

I would say I probably got about a 60 % or 70 % Connect Rate.

Maybe it was lower than that, but it was a shit time. I could make calls all day and talk to a lot of people. You know what I'm saying? And so if I messed, I remember thinking this, if I messed up my introduction or I messed up my message, I could make seven, eight, nine calls and I'd get three or four more connections in that period of time. So I would just keep working on it. Now you could literally make a hundred calls in a day and maybe talk to two people. Maybe. So connect rates are different. People are not responding to emails.

It requires an entirely different approach and message to get their attention and get them to pay attention. we figured plus AIs come out so the whole AI component for us. So I wrote it. And the other one is everybody was always product centric. Everybody's my product, my product, my product, my product, my product, my product. And we recognize the same thing we did for gap selling, that problem centric selling is the best way to do it. So we taught people how to leverage their problems to prospect not their product.

Digital Rebels Consulting (04:31)
Makes sense. I noticed in the last couple of books, ⁓ you did it yourself. At least that's at least what was on the front of it. You brought in a coauthor for this particular one. Why did you bring in Will for this particular book?

Keenan (04:42)
Sometimes you get too close to things you don't see what you don't see and Will actually came to me and he said hey we should do a Gap Prospecting book and I was like I don't know and he was compelling he was very compelling and I think one of my concerns was I understood prospecting but I hadn't really had to do it myself in a while and he was very

was very compelling in helping understand that he had really done a lot of the tactical stuff. So between my framework of problem centricity and how to leverage that, and he could apply the tactical elements, it was a good partnership.

Digital Rebels Consulting (05:25)
So I believe that you developed a problem centric operating system. me a little bit more about that. And I think how you've applied that over many, many years of success.

Keenan (05:33)
Woo, that's a big question, bro.

Digital Rebels Consulting (05:35)
So I imagine that ties a little a lot of what you've already written before a lot of what it goes into prospecting so Take as long as you need

Keenan (05:43)
So that's a big one. OK, so the problem centric operating system came out of the recognition that's.

If in the old school everybody was product centric and gap selling recognized you needed to move to problem centric, we felt that in the world of sales enablement and actually making this stuff stick, that everybody was product centric in how they trained their salespeople, what they trained their salespeople on, how they built sales enablement models and how they built sales enablement environments that you needed a problem centric operating system as well.

So once we determined that problem centricity need to be at the center of your sales enablement, which should drive how you train salespeople, we then came to the conclusion. I was like, wait a minute, sales enablement.

Sales organizations made a mistake when they went to sales enablement because what they started to do and what they leaned very heavily on was learning and development. They hired learning and development experts, they hired people who were behavioral experts, they hired past ⁓ professors, people in the learning and development world who could build curriculums, build trainings, you see what saying? And I realized that that wasn't enough.

and then it became disconnected from sales operations, which then was disconnected from the sales team and sales leadership. And so they do all this training and the metrics they started to use, but the training was just atrocious. I will never forget this quick side note. And I won't even say the name of the company, but they're in serious trouble. And I'm not surprised, right? Because...

⁓ We were a finalist in a sales opportunity with them and I'm talking to the head of sales and they were a bunch of people on the phone but the head of sales and they were and we're breaking down all the business problems they have and we're showing how our product the service is going to address those business problems and fix things like poor discovery fix things like low win rates like we're really talking about the dirt right

And she goes, well, I have a question for you. And I said, what? This was her first question. Global head, global head of sales management. And her question was, does your online training platform integrate with RLMS?

I was like, okay, can you help me understand why? And she said, well, it's really important for us to have a single point of entry. I was like, these fucking people have no clue what they're doing.

If that is this high, single point of entry. And then, and then, and another point in the conversation, we were talking about metrics and it was clear they weren't measuring things like win rates. They weren't measuring added pipeline. They weren't able to connect all their efforts to the outcomes, right? And they weren't. And I said to her, said, do you guys do any metrics to measure anything? Cause I'm not hearing. Oh yeah, we totally do. And I said, what's the number one metrics you're managing now? And she's, oh, we've actually moved to a really proud. It's number of certifications and number of people who take the training.

Digital Rebels Consulting (08:28)
Mm-hmm.

Keenan (08:28)
That's what they were measuring. So why am I telling you all this? Once I understood this, we realized that there are actually three layers to a proper sales organization when it comes to enablement. The skills layer is only one piece. That's where you teach them everything. But enablement needs to then move into what we call the opportunity layer.

And that's where you have to start building processes and tools in which is also obviously a process, evaluation elements, et cetera, to evaluate what you taught them in the real world setting. So role play is still in the skills layer. However, ⁓ video review, deal review, ⁓ passive and active reinforcements or passive, it's just something we also just came up with, passive reinforcement is,

You can't do something in our process if you don't know what we taught you. Right? So I don't even have to do active reinforcement. It's, go do this. Well, if you can't do that, then I already know you didn't get through the training piece, right? You're not, you're not comprehending. So, um,

Digital Rebels Consulting (09:19)
Mm-hmm.

Keenan (09:29)
So then we built that that layer up to you. And then the last layer is the forecasting layer. And that is, do you take everything from the skills layer, reinforce it in the opportunity layer, and then can you see it flow through to the forecasting layer? Things like forecasting criteria. That forecasting criteria should connect all the way back to the shit you taught them in the skills layer. If it doesn't, then again, you don't have a really good sales name or platform. So we recognize we did all that. I told you.

long is sales organizations have a learning and development organization when it comes to element. They don't have a performance enhancement and development organization because performance enhancement and development relies equally if not more on assessing in real time and then measuring against outcomes.

We need all three layers and then in the middle of it going all the way through is problem centricity. That is like the foundational ribbon that goes through the entire thing. You start with problem centricity, go into skills layer, from skills layer to opportunity layer, from opportunity layer into forecasting layer and that spits out the outcomes.

Digital Rebels Consulting (10:36)
Is the problem just that companies, is it, is it the lack of structure? If it's the lack of processes or just the fact that they just get too big and then everything just gets siloed and just more complex and just screws everything up. So how do companies screw this up as far as the three layers, as you simply put it, but, ⁓ poor and execution.

Keenan (10:55)
Yeah, so it's actually three layers, right? Or three things. The first one is yes, they get too big. I mean, but I see this in small companies as well. So it's not a big company challenge. But like anything else, it gets too big, it's too unwieldy. And then once that flywheel gets going, it's hard to bring in. Secondly, which I think is the most important, is most companies are product-centric. When you're a product-centric selling organization, right? What evidence are you using to demonstrate or highlight

what the team knows or what they've been taught and how do you tie that to an outcome. So it's all behavioral based. I'd say to companies all the time, go through your onboarding. What percentage is about the product?

And then what percentage about sales competencies? And the sales competencies are stupid shit like how well can they pitch the product? How will they overcome objections? How do they do a discovery? But then you ask, how do you define a discovery? What do you teach them to look for? And then all of a sudden it falls apart. So when it's not problem centric, it's very difficult to pull product centricity all the way to the forecasting outcome. Why? A product centric

does a very bad job of uncovering the business case. A very bad job of uncovering the business case. So if you don't uncover the business case, what are you measuring somebody on in the opportunity layer? Like literally, what do you have to measure them on when they're actually doing it? And that's what happens, they'll go to Gong and they'll watch a rep, but because product centricity really doesn't have foundation, every manager is doing it different.

because they're trying to measure behaviors, but product centricity is not behavioral based. Problem centricity is, but not product centricity. So those are really the two big ones. There's a third one that escapes me and I'll get to in a second, but when it comes back to me, but those are the two main reasons they get too big and they're product centric.

Digital Rebels Consulting (12:38)
Um, you mentioned about the discovery questions, which I'm sure that's a question that you get time and time again. And I know that you teach a lot of this. So what makes a good discovery questions? Like if you're onboarding somebody and you're not telling them to be product centric, how are you teaching them to be problem centric and ask good discovery questions?

Keenan (12:57)
So one of the things we teach is it's not about the questions. mean, it's gonna sound counterintuitive, because yes, great, great questions produce the best discovery, but you cannot script the best questions. It's actually the business acumen and the understanding of the business that you're selling into. The more you understand the business you're selling into,

By default, the better your questions are.

And so sales organizations, in my opinion, need to flip the script. They need to spend the first, whatever time, onboarding time you have, let's say you have 90 days to onboard, 30 days to onboard, they need to make that 60, 40, 65, 35, 70, 30 business problems, business assessment, KPI awareness, executive role awareness and motivators. You need to know everything you can about their business. And then the question is, what the sales? Yeah.

Digital Rebels Consulting (13:50)
Well said.

Well, I typically have deployed that as well. And I think it just comes naturally. It actually helps you, think, become a better seller, whether you're on video or whether you're in person and more importantly, when you're in person, because you don't have any cheat sheets to go back to and say like, okay, what's the, what's the script that I need to, you know, answer that particular question with. So if you know the business inside and out and you know the business better than the people across the table from you or just as well, I think that makes you tremendously powerful. helps you craft better.

dialogue, better questions, better answers. And it also just shows that you're prepared. You came to the, the meeting, not just to go through the motions and bore the hell out of somebody with an hour long, you know, ⁓ diatribe of your product and your company. And it sounds like a script. that's really the way to win. And obviously you've taught that to a lot of people. And that's just something that I truly enjoy, but it's just something that think people just for some reason they miss like that. Even though we talk about this on a regular basis, we talk about, you know,

understanding the business. talk about understanding the products, understanding the problems, understanding the solutions and how they fit into the customer's problems. Everyone just still seems to miss that. But I also feel like it's a crutch because the company is telling you, need to sell the products. And so when you get to against that wall, you fall back on what's most comfortable for you. And it's just talking about the product and it's not talking about the business because you didn't do the research because you didn't prepare, which is always just frustrating for me to just to hear people who ask.

quote unquote dumb questions because they should be able to find them that answer out themselves before they even showed up. Would you agree with that? Please do.

Keenan (15:18)
Well, I'm going to push back a little here.

Yeah, so I agree with you. You should do some research and understand the context of the world you're in. But the type of great discovery questions, can't, generally speaking, 90 % of the time, you can't find that publicly. You can't, right? So great, great, great discovery questions. And the best discovery.

obviously leverages what you know about the problems, the impacts, the root cause that organization is having and where that organization plays, but then the best discoveries questions cause them to reflect. That's how I know someone is good at discovery. They're able to ask questions and get the buyer to reflect. So you want, you asked for a question. There's one question I always say every single discovery call should start with. Can you tell me what prompted you to take this call today?

That's it, I shut up. That's the question. Now, you get one of two answers, Marc. You get one of two answers. The one you usually get is, we wanted to learn more about your product, or we wanted to ⁓ learn more about ABC, or we wanted to talk about how we could do XYZ. So they're all future state oriented. So let's just go, say, we wanted to learn more about your product, or we wanted to... ⁓

Well, we want to grow our revenue and we want to do something like that, right? But the harder one is we want to learn more about your product. So what I do right on the heels of that is I say, okay, is there something going, because there's a deflection, they don't even know it. Is there something going on in the organization? Can you walk me through what's happening that has you even considering?

learning more about sales training and what we do. What's going on? Now sometimes I may feed them. Are you guys struggling with win rates? Are you not seeing the pipeline you want? Are you BDR struggling? You don't have to with the convert, like I might see them a couple, but see what I did? went right back to what the fuck is going on. I'm not gonna talk to you about my product.

Digital Rebels Consulting (17:02)
Mm-hmm.

Keenan (17:04)
because in the absence of what's going on, I'm wasting your time and I'm wasting my time. So let's get this on the table. What's going on?

Digital Rebels Consulting (17:16)
Tell me about the problem identification chart and how you deploy that in these particular calls.

Keenan (17:21)
So the problem identification chart is gold. Everybody tries to do it on their own and everyone's in a blue moon. Someone does a half-assed job and ooh, that's kind of impressive, but it's hard as hell. But the problem identification chart is basically, and that should be part of training in the skills layer very early in the beginning. Build one and then train everybody in it. It basically breaks down the problems that your product has solved. It breaks down the products ⁓ and services that you're, okay, one more time.

It breaks down the problems that your product or service solves for your prospects in advance. it's, think about three columns. You have the business problem. You have the impacts. You have the root causes.

And what, this is, have yet to see this change. Now, if you're a multinational and you have a thousand products and you can have multiple, potentially multiple pick. So if you're, what is that, P and G, Procter and Gamble, yeah, I'm gonna have a pick for my Unilever deodorant and I'm gonna have another one for my shaving cream, because they're entirely different products. But most companies, even if they have a lot of products, we have multiple products here, but they still almost always drive to the same set of problems.

Okay, so there are normally only between three and five problems your company or your key products solve. So the first thing we do is we uncover what are those business problems. Then from there we ask ourselves, if those business problems exist, what are the impacts to the organizations? And that could be infinite, but it's like 80-20.

80 % of everybody has the same 20 % of problems and then we can deal with the rest later. I mean impacts, but they're all very similar. And then the last thing we do is we ask you to write down what are the root causes? What causes those business problems to exist? Now here's where everybody messes up, here's a freebie to everybody. Root causes are broken processes and tools. My mic stopped working.

It takes too long to do something. I lack visibility into my reporting. I can't do the reporting. All of those are broken processes. have distributed systems, architecture is unwieldy. Everything there is a root cause. 99 to 10 nines. When people try to do this on their own, they list the root causes. They're so embedded in the root causes, they don't know how that funnels into a business problem.

When you look at those root cause and you say, well, ⁓ we lack visibility, our customers lack visibility in XYZ, they have distributed systems, et cetera, et cetera. Then I'm like, what business problem is that creating? And I make this up, unplanned downtime. That's a business problem. I can't fix that directly, right? So there's your other hand. You can fix root causes directly. Microphone's broken, I can buy a new microphone, okay?

unplanned downtime, can say, oh, no, fix unplanned downtime. No, I have to figure out why. Why is there unplanned downtime? See what I did there, Marc? Why? Unplanned downtime is I have poor reliance maintenance schedules. I don't keep the proper inventory in place. I don't have enough people on my team. So I have to fix each of those. And when I fix those, now I can address the unplanned downtime.

And so if I'm selling something that addresses the business problem of unplanned downtime, usually every root cause is what my product or service solves. I have extra people, I have a strategy, I have a software. Do you what saying? I have something that solves that. And the last piece of this is you measure it. Unplanned downtime. How long? What machines? How much money? See what I'm doing here? Then you measure that and you say, okay, because of this, ⁓ what's the impact? Lost two of our biggest clients recently.

or better yet, it be a health system. We got fined for being out of compliance. That's the impact. Now imagine having all of this written down before your very first salesperson makes a call and you tell that young salesperson or old salesperson, memorize the F out of this.

Digital Rebels Consulting (21:11)
Mm-hmm.

Keenan (21:11)
So now when they get on a discovery call, they're not all over the place. They're like, tell me what keeps you up at night. They literally do what I say. They say, hey, walk me through what prompted you to take this call today. And the buyer says, oh, we just wanted to learn what you do. And then you say, well, when you say just learn, was it something in particular that prompted you to want to learn about what we do? Are you struggling with unplanned downtime? Well, as a matter of fact, we are. See what I did right there? Dude, it's fucking laid out. You taught your team on it. They'd say it and the customer

Yes, we are. And then you say, could you help me understand a little bit about your current reliability maintenance strategy? In two minutes! In two minutes! I am neck deep in their business and I only had to three questions and I was guided by my pick.

It blows my mind that my dumb ass in 2020 figured this out before anybody else. Sandler, Rackham, anybody. No one figured out. You start with assessing your client's business before you teach your reps anything and you make them memorize that shit and then they build their entire discovery trying to find the problems on that pit. And if they're not there, you pack it up and say, thanks for the time, but we can't help you, but I'd give you a recommendation to someone who can.

Digital Rebels Consulting (22:22)
So since 2020, what's changed in that particular process? Is it the same just because humans haven't changed or has it changed because of AI or something else, or is it basically the same as it was?

Keenan (22:31)
Bye.

It's

never gonna, it will never change because that's how we buy. That's how we change. That's how people process change. So if anything, the AIs will just get better at helping you reflect on your environment. The AIs will be better at asking the questions or understanding the business. So then when the AIs take over, whether it's emails or calls or actually in person like this, they will do a far better job of being able to diagnose what's going on in your organization based on your answers. That's what salespeople fall down.

today, a buyer will say something and the rep won't understand the business ⁓ component of that and won't know what question to ask. But the AI will be like, ⁓ they just said that. And the AI will quickly jump to something deep in the business. And the buyer's like, ⁓ reflect. ⁓ yes, I didn't even think about that. Great point.

Digital Rebels Consulting (23:22)
So the new book is about prospecting. So how can artificial intelligence help with prospecting? Or I guess, how does it make it worse?

Keenan (23:28)
depends on how you apply it.

But to making it worse, I look at AI as people. mean, perhaps you don't want to hear that, but I look at AI as just an extension of people, right? So what I'm seeing right now is a lot of AI.

Software companies or whatever you want to call it who are building these things are building AI just like the same doing the same thing they did to salespeople

and they're making them do the wrong thing. So they're building AIs to overcome objections and teach it, overcome objections. They're teaching them to pitch the product, et cetera, but they're actually not teaching them an actual methodology to stop and assess the business element. they're not, look, I wouldn't care if it's us. If I was building AI anything for sales right now, I would pick one or multiple methodologies and train on those methodologies. Just like you should train salespeople when you hire them on methodology, but we don't.

They're building AIs just like the average idiot salesperson, overcome objections, address negotiation, but they're not giving the AI a foundation, foundational framework to actually do that work. Does that make any sense?

Digital Rebels Consulting (24:30)
I think so because I've always looked at AI as just another tool, kind of like Google, but it depends on like a hammer. It depends on how you use it. Depends on whose hands you put that in and how they're going to deploy it. Because if you use AI and I think the way that you're describing and you put some guy rails around it, you put a foundation to it, you put better information in there, you're going to get a better output. No different than how we used to Google things. I always always say like, I was a good Googler and there's always people that just know how to use it properly. And the same thing with the hammer.

The hammer in my hand is probably going be different than the hammer in your hands as far as just the output that you get out of it.

Keenan (25:00)
Well, here's a slight

difference. Google was flat. So yes, if you could write a better Google request, it was still flat. Google really wasn't thinking. And it gave you a bazillion options, and you had to scroll through them. Now, when you do this, the AI does a bunch of thinking on its own in the background. And so if you're going to build an AI SDR system, let's say, and you're telling everybody how great this SDR system is,

what framework did you give it to write the email? So as a perfect example, hit everybody, with AIS, with Gap Prospecting, one of the things to our framework is we recognize that there are two sales to get a buyer to open an email. The first sale is intrigue. Can you create intrigue to get the buyer to stop and say, ⁓

All right, I want to read this or if it's a cocoa, all right, I'll give you another 30 seconds. I'm intrigued, right? I'm intrigued. The next sale that, you can't get the next one without the first one. So once you get them intrigued and say, yes, all right, I'll buy, right? That's small sale, but it's a buy.

then you gotta get them interested to react to the call to action. So if it's an email, to click on something, download something, write back, whatever, or if it's in a code call, to say, all right, I'll have a meeting with you. That was interesting enough. You intrigued me, now I'm interested enough, I will give you half a bow, whatever, whatever. So if you don't teach the AI that, it won't know to do that.

That's my point. that model in itself is something we teach and then we describe what intrigue actually is because there was science behind intrigue. So in Gap Prospect, we don't just say build intrigue, we tell you what the hell it is. We tell you what the four ways to do it are. We tell you how to do it with what part of the brain it triggers. So if you don't teach an AI to do that, it's not going to do that.

Digital Rebels Consulting (26:43)
Yeah. And I guess that's kind of like a back to my other example. You kind of have to understand how something is supposed to work. ⁓ kind of what the inputs to put into it in order to make it work correctly. So I guess back to my hammer example, there's different ways you can hold a hammer in order to get that nail driven. So if I hold it upside down, I'm going to do a shitty job. Or if I put in a crappy, you know, Google request, top 10 restaurants near me, that's not going to give me a good result.

Keenan (26:58)
Yes. Yes.

Digital Rebels Consulting (27:08)
So in the same thing with AI, I you don't understand like in the backend of how it's going to work and put some parameters around it, or at least maybe do a little bit of research before you just put it in these blind requests and hopefully you get a right answer. That's the other problem is that a lot of people, think they probably get an output or an answer and they're just like, okay, they told me that's what it is. So instead of questioning it again, or asking a better question or understand, like, where did you get that answer from? Just asking more questions, asking better questions, understanding.

maybe it's not a linear approach, at least that's happened in the background. There is a dynamic aspect to AI and understanding that and putting in better questions in order to get better results, just like you would in a.

Keenan (27:45)
I'm sorry.

I'm sorry, I misinterpreted. You're talking about chat, GTP. my God, chat, GPT or Claw. You're talking about that. I was talking about the AI companies who are building the AI agents for us. So whether that's SDR, whether that's email writing, I was talking about that. And I'm saying those organizations are not building their agents, not building their tools on a, in my opinion, a sound foundation.

They're not going out and saying, to your point, what is the best way to swing a hammer? What type of hammer do I swing? Do I swing a finishing hammer when I'm finishing? ⁓ A mason hammer when I'm mason, see what I'm saying? And they don't know and they're just saying a hammer is a hammer and they're building these whole agents, a company of buying in their organization to do some of the work. And they're just putting more dumb salespeople in front of the customer. Your point.

Digital Rebels Consulting (28:36)
I'm surprised that

you could actually label or you know the names of hammers. I don't. But so that impresses me and surprised me. I believe that.

Keenan (28:42)
Yes, there are framing hammers, are finishing hammers, yes

there are multiple, ⁓

Digital Rebels Consulting (28:48)
But I think we're both saying the same thing, but there is a convergence

of where you get garbage out because I've used a lot of AI tools, AI software platforms, and sure, they're building AI solutions, but it's the same thing. I've used a lot where I put in a prompt or whatever it is, and it's not chat GPT, it's an AI driven solution, let's just call it. But the output is still garbage and you still don't know me and you still don't know really the questions and the problems that I'm trying to solve. So I think it's, it's still a human built.

And especially if we're talking about young SDRs that are in there they're just kind of going through the motions, it's garbage in garbage out for lack of a better phrase.

Keenan (29:32)
Yes, to solve that problem, actually wrote a prompt. So people could buy Gap Prospecting. We wrote a prompt for reps that can do almost everything for them, taking in the kids' situation, intrigue, problem centricity, interest, problem centric, all of it. It's all built in, targeting around the problem, driving intrigue, et cetera. So they just have to basically put in their business. They have to fill out their own problem identification chart. We forced them to do that at beginning of the book, but we leverage the problem identification chart. Then we, yeah, it doesn't matter. We give them the whole prompt.

to your point. And we tested it over and over and over and it's fucking impressive.

Digital Rebels Consulting (30:03)
Is it just one prompt or they have like options?

Keenan (30:06)
it's one prompt. Now, the options are to customize for your business. So option one, watch this. That's an interesting question. It goes back to why Gap Signing is so good and Gap Prospect. Once you do your own problem identification chart, that narrows it down. Do you see what saying? So you do your problem identification chart. In other words, what are the business problems we solve?

what it impacts an organization if those problems exist, what are the root causes? You put that into your chat or your cloud or whatever the hell it is. Then we give you the prompt and then we do things like we call symptoms and catalysts. So we force you to figure out what your symptoms and catalysts are. So then you put in the problem and indication chart, you put in the symptoms, you put in the catalysts, and then we give you the prompt that tells it to trigger the AFC and the OCC. Don't worry about that. It means the psychological elements of the brain. For entry, you have to put in who your body

So you're going after so if it's a CRO or it's a CSO or whatever so now you you tell it to find the problems that you take your pick you tell it to attach it to this type of personality then you use the things you found from a symptom of catalyst in a search we saw this or you saw that and then you and then it does it all for you. It's powerful. It's powerful.

Digital Rebels Consulting (31:13)
Nice, looking forward to that.

For gap prospecting, what are some other, what's something that I probably would learn that I guess I wouldn't expect to learn from gap prospecting?

Keenan (31:25)
Catalysts symptoms?

Digital Rebels Consulting (31:26)
catalyst and symptoms. Tell me more about that.

Keenan (31:28)
A catalyst is something that could happen that would suggest it would create a problem. What could be a catalyst to a problem? Something in the marketplace. So let's just say you sell cybersecurity to banks and let's just say a mandate comes to the government that says, if you don't...

If you get breached and customers lose their money, the fines are XYZ or you have to, get a ding in some sort of, I'm making this up, some sort of, you know,

Ranking and if you get that ranking you can't do certain things so we know that's a catalyst that You're probably gonna be now in the market for ensuring that your cyber security is up to par because you can't afford it you can't afford to You know saying to have a breach. That's a catalyst a symptom is something that suggests that you might actually be Experiencing something that could mean the problem exists. You know I'm saying so a Symptom could be somebody hiring

a shit ton more cyber security analyst or something. Hmm, what's going on? That's a symptom that something could be going on. So you use that to go back to the problem identification chart and write emails and say, see you're hiring people. Normally when we see this, this is what's going on. Is that what's happening with you? Are you open to a conversation? Blah, So symptoms and catalysts.

Digital Rebels Consulting (32:42)
Nice. I love that. Looking forward to that. Let's pivot over to our most popular segment of the Burn the Playbook podcast, is Burn it or Build it, a rapid fire segment where I'm going to give you a topic. You tell me a Burn it or Build it in a brief reason. Why? Are you ready? Well, you can be brief. You can be long. We have as long as you need. Number one, daily activity quotas as the main goal for sales teams. Burn it or Build it.

Keenan (32:55)
Reach is the hard part.

as

the main goal. Burn it.

The main goal should be the outcome. So the main goal is if you want people to do two meetings a day or two a week or whatever, that should be the goal, right? I don't mind you watching or assessing what does it take to hit that goal, but...

is I interpreted the question, if my activity is what I'm measured on, and let's say you tell me to make 100 calls a day and I make 100 calls a day and I get six meetings and I'm only supposed to do one, and the next day I only do 40 calls, don't you fucking dare get in my face that I didn't make 100. Don't you dare. Don't you dare. And I don't wanna hear this, you could do 12. Yeah, I could, but know what? I didn't today. So, no, that was me too. I always said managers, I would always make my number, but didn't always do it the way they wanted me to.

and then they would get in my grill and I was like, I don't have time for you. I don't have time for you. No, I'm getting the outcome, so get off my back.

Digital Rebels Consulting (33:59)
get off your back, burn that. Number two, buyer intent metrics.

Keenan (34:02)
If they're good, leverage them. that buyer intent, I mean, if my world buyer intent is symptoms and catalysts, right? So if it's a symptom or catalyst that I've identified, like again, we do a lot about front work with prospecting. We know what those symptoms are. We know what the catalysts are. So to us, that's buyer intent. But a traditional buyer intent, it's too correlating. I want real problem-centric buyer intent.

Digital Rebels Consulting (34:07)
How do you know they're good?

We could just use a Brent Adamson's ⁓ third ⁓ option, which is rebuild it since he created a new category for this particular segment. number three, phone first prospecting versus email, social, phone first.

Keenan (34:36)
I like that. Rebuild it. Yeah, I love them.

Burn it. Every industry is different.

There are some industries you could probably live entirely on LinkedIn. So why don't you just live on LinkedIn? There's others like construction. You'll never get anything on LinkedIn. So why would you do that? I think phone first for things like dentists and doctors offices is brilliant. That you can call them at 7.40 in the morning and get the lead dentist. But then that shit's not gonna work for a CRO. You're never gonna get through the CRO on the phone, ever, ever. So you miles a row with email. So now, I believe in multimodal.

and then you determine what works best for your clientele and the product you sell.

Digital Rebels Consulting (35:21)
with that 100%. Number four, multi-threading on day one.

Keenan (35:25)
⁓ burn it to the ground. Come on, man. Come on. I mean, okay, okay. So I heard day one as my first discovery call.

I'm okay with multi-threading from an account management or what's what I'm looking for, account-based selling. If you're gonna account-based sell, I am absolutely okay with multi-threading because what I'm gonna try to do is I'm hit them all, whoever responds first, I'm gonna go for. But if you're talking, I hit someone up and I'm talking, I'm not gonna start telling them who else do need to talk to and all that, no, no, no, no, no,

You just stay with them, get to the problem, and the problem will guide you to where you need to go from there.

Digital Rebels Consulting (36:05)
Some people hear multi-threading, they read about it and they're like I should do that all the time. So that's the reason for the

Keenan (36:11)
But okay, so to your point, my God, I know you want this fast, but this is perfect example of why sale is all screwed up. Multi-threading is not selling. That's transactional. That's a transactional element. The difference between gap selling and every other selling is gap selling is problem-centric and that's change management. ⁓

who the decision maker is, the buying process, and we build that in there, but it comes later. All of that stuff is transaction management. And if you're managing the transaction before you've quantified the problem and the cost of an action, you are wasting everybody's time.

Digital Rebels Consulting (36:50)
Makes sense. Well said. Number five personalized openings pulled from a buyer's public post.

Keenan (36:56)
Say that again.

Digital Rebels Consulting (36:58)
Personalized openings pulled from a buyer's public post. Hey, I saw that you went skiing. I love skiing too. How about you come listen to my demo watch

Keenan (37:08)
Yeah.

No, I don't, what is it? I'd say build it, but build it correctly. So rebuild it like what's his name say? I love how you did that. I saw you posted about, not skiing. love skiing. No, I saw you posted about skiing and your last trip to Vail over here at, when a park.

We do these things and more. So I'd love to talk about maybe considering your next skiing thing at Winter Park. That's okay. So if what you're pulling is germane to what you're selling all day long, if it's to try to just make a connection, I like skiing too. So, hey, what do you think about robust cybersecurity? No, no, no, no, no, no, no, no.

Digital Rebels Consulting (37:51)
Number six. So what was that about? That was a rebuild it.

Keenan (37:53)
As long as it's connected to what they're talking about, you people talking all the time about, I saw your post and trying to find a fantastic selling methodology. Would you mind me asking what prompted you to that post? Are you considering one internally? the one you're at work? That's all day long, bro. That's a catalyst or a symptom. Sorry, that's a symptom.

Digital Rebels Consulting (38:10)
Number six, long form sales emails. I've seen some recent hot takes on this that longer is better. Burn that. Okay. No one has time.

Keenan (38:14)
No, burn them. Burn them. Burn them. No one has time. No one has time.

Nope.

Digital Rebels Consulting (38:21)
Number seven, video messages.

Keenan (38:23)
Build it all day long. I don't know why more people don't do it. Love it. Love it, love it, love it. If you want to do it long form, do it that way. You can start talking to personality, ask questions like, you know, you're good. Keep for a minute, minute and a half. Ideally, no. Yes, right. It doesn't seem like it. If you're really good and engaging, you know, 30 seconds.

Digital Rebels Consulting (38:27)
Number eight.

⁓ How long should a video message be? 10 seconds? 3 minutes?

elevator pitch.

Keenan (38:43)
You can go a

minute, you can go a minute if you can really drive home and get some good stuff to talk to. Like, hey John, I saw that trip to Vail you took where you hated the lift lines. Right over here at Park we're having a big, big...

I don't know, fucking whatever, sale on our condominiums. The lift lines are only one third of the period of time. We have just as much skiing. I saw you said you really like this and this. Let me show you how we, you the bumps we have, the runs we have, the type of whatever. And I just go to it, right? Love to talk to you about how we might be able to plan your next ski trip based on what I heard at Vail and why I think you'll like it. So yeah, that's great.

Digital Rebels Consulting (39:13)
sounds good. Number eight, text message outreach messages.

Keenan (39:17)
Burn it. Burn it, burn it, burn it. Once you establish a relationship, I'm chill. And I'm sure some millennials and Gen Zs are like, what are you crazy? But no. If I don't know you and you come across my phone, that's probably where I'm going go. It's over. It's now.

Digital Rebels Consulting (39:32)
That's over. That's over.

Number nine, gifting to open doors.

Keenan (39:38)
No, burn it. Okay. The way, yes, so that's I was going to. it. I love, I leave it to Brent, rebuild it. So do not send me $100 Amazon. My time is a fuck ton worth more than $100. I'm insulted out of time for you. But if the gift isn't about the value, but it's about the creativity.

Digital Rebels Consulting (39:40)
No? Not a fruit basket? What about gloves for the skiing trip?

Keenan (40:01)
Or it's, it's, it's so remember I talked to you about there are elements that create intrigue or interest and there's very real ⁓ psychology behind that. One of the elements of psychology is called surprise. So if you are a skier and I send you a pair of customized ski gloves and I'm with Winter Park and I'm trying to get you to consider having your event here all day long, all day long.

Right, now the message behind it has to be problem centric. So that was a surprising way to, see what I did there, a surprising way to intrigue you through surprise. You are now surprised that created intrigue. Now I brought you into the interest section. Now it's up to me for my message to create enough interest to create a meeting. We call this the often to ask ratio. Read the book, right? So yes, in that regard, I'm a huge fan, but it takes creativity. It has to be relevant.

and has to not be gimmicky.

Digital Rebels Consulting (40:55)
Number 10, my favorite is breakup emails.

Sent you three emails and the fourth ones at the. Yeah. Okay.

Keenan (41:00)
Yeah, I'm good with that. Yeah, build it. I'm good with that.

It's not anything respectful. Yeah, 100%.

Digital Rebels Consulting (41:07)
What if it's an AI generated breakup email because the first three were as well.

Keenan (41:11)
Yeah, okay, well, go

back to AI. If that AI was built on gap selling, still build it. If that AI is built on traditional selling methods and with no real framework, no real methodology, then burn it to the ground.

Digital Rebels Consulting (41:23)
Sounds good. Love it. You get the final word. What's one contrarian move a sales leader can make in the next 30 days to lift win rate for 2026 Q1.

Keenan (41:32)
Let's start with knowing. Let's start with that. Let's start with actually knowing your win rates over at least a three to five year period, if not for the last 10 years, but at least a three to five year period. Know your win rates, know your win rates by rep.

Digital Rebels Consulting (41:36)
Mm-hmm.

Keenan (41:44)
and then have them ranked or at least evaluated. What is my highest win rate? What is my lowest win rate? What can I do to go in and see what's going on there? And from that, begin to start running your organization as a performance-based sales organization. And performance-based does not mean on quota. Put quota aside. I wanna see things like win rate, average contract value, average time to close, pipeline being added by rep. And I want to see

what skill sets are behind those who are doing well and those who aren't. If I have a methodology that I want to see the correlation between who is executing that methodology and who isn't and does it actually correlate to the better outcomes. If it doesn't correlate at all, then you're not even using the methodology. So it's time to retrain them or get rid of it. But that's what I want to do. Make your organization a performance-based organization by looking at the behaviors behind the numbers.

not just the numbers.

Digital Rebels Consulting (42:42)
Well said. Where can people find more information about Gap Prospecting for 2026?

Keenan (42:48)
You can run gap prospecting in the search and that will come up. Yeah, it's pretty easy.

Digital Rebels Consulting (43:06)
all over the place. Love it. I appreciate you joining the podcast and ⁓ looking forward to chatting with you again.

Keenan (43:12)
Thank you, Marc. I appreciate it. Good work.

Digital Rebels Consulting (43:14)
Thanks.


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Marc Crosby - Digital Rebels

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