AI Is Changing Sales Leadership: The New Skills Every Sales Rep Needs with Kristie Jones

Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. And I guess this week remembers when coaching meant a manager rolled up a chair, sat knee to knee with you, and plugged in their headset into your phone and listened to your call live while you were making it. She calls it torture, and it absolutely was, because I went through it as well. But she also points out that the people got a whole lot better a whole lot faster back then. Chrissy Jones is back for round two. Last time she was on, we talked about reps taking control of their own careers.

This one is about the people leading them. She went to six conferences last fall and sat on every session she could get into, waiting for somebody to talk about how AI changes the way you have to lead a team, and nobody did. So she went home and wrote the book herself, and it is called The Sales Leadership Gap. We got into why she believes marketing is about to own the first two stages of the sales cycle, why the post-mortem needs to die and get replaced by a pre-call meeting, and how she is testing candidates now by making them show her their prompts live during the interview, which I thought was really interesting. So I hope you enjoy this conversation as much as I did. Let's make it happen.

Chrissy Jones, welcome back to the Make It Happen Monday podcast, my friend. How are you doing today? I'm good, John. I'm excited for our conversation today. We always never seem to have a shortage of things to talk about. No, we don't. Like, we should have hit record before we got on here, just because we're trying to solve all our own world problems when it comes to sales consulting out there. But I think we're trying to solve some other people's problems during this conversation, because last time we talked, it was more about kind of the, you know, the individual rep taking control of their careers, right? Like treating it as a sales process with your ICP and finding out, you know, understanding that lens and everything else.

And I forget, what was the book called? That book was... Selling Your Way In. Selling Your Way In. Thank you. And now you've got a new one coming out, The Sales Leadership Gap. Yes. Why? So let's start with the why. Why do you think this book now, like, we'll talk about the details of it, but what drove you to write this at this moment? I went to about six conferences in the fall last year, and I sat in on everything, right? Like, I was trying to make the decision. You and I sort of talked offline about this, but I was trying to decide, like, is it get out time or is it dig in time, right? And I think I felt like the only way... This was like June or July, and I was just like, I don't know what's happening here, but I either...

So I thought the best thing for me is I'm a consumer report girl, so I'm like, get educated, right? Yeah, there you go. I'm like, get educated. And the fastest way, because the fall was coming, the fastest way I thought to do that was to attend every conference I could get my hands on. Some I spoke at, some I didn't, everything from startup weeks to pavilion to the business of software. I attended everything I could get my hands on. I was traveling a lot. I sat in on room after room after room, and I heard every version of AI, about AI, except the how is it going to have to change how I lead my team. No one was talking about, you know, they were all talking about making a decision and what tool to use and this, that, and the other.

And it was all very practical advice, tactical advice. But I kept sitting there waiting for somebody to talk about how it was going to change, and not just sales leadership, but leadership in general, but I was at sales conferences for the most part. But nobody was talking about how we were going to have to change how we hire and who we hire, how we're going to have to change how we lead. None of that conversation was happening. And so I came back and, you know, synthesized everything into my AI and said, like, what are the big themes here? And it just didn't pop up anywhere. Yeah. Then you're probably one of the best people I can ask this question to, because this is the one that I am fundamentally struggling with.

And it's about the fundamentals. So my position on this is, you know, we've over-operationalized sales, a predictable revenue model kind of turned it into way more of a science than an art, blah, blah, blah, blah, blah. But, and we need to get back to the art. But the problem is this, is you and I, the grind that you and I went through early in our careers, like the shit work, right? Like they're writing stuff down, knocking on doors, literally taking photographs of just directories. And you know what I mean? Like all that shit, right? And literally, I don't know about you, but getting physically thrown out of offices, right? Never happened to me, John. Ever, right? Well, all that stuff turned us into the business professionals that we are today with context, with grit, with, with understanding.

So this is why we don't have to have a script when having a conversation with somebody. This is why it feels much more natural for us, right? Than it would. But now AI is, is, and pick out, I'm going to pick on sales, but any profession, the entry level, any profession, arguably can be done better with AI right now. I mean, you put me up against a first year law student without AI. I bet you I could be pretty damn good lawyer, okay? Based on how I know how to use this. So the questions, there's two questions I have. One is, um, where do the fundamentals come from? Okay. And I think we can get back to those and whatever, but the one that I'm struggling with the most and it, and it hits on what you just said there is what are the fundamentals anymore?

And are they changing? Like, I think now in the flux that we're in with the unknown of, I think it's easy to say, well, let's go back to the fundamentals that we know. So it teaches the kids, the, the, the, the leadership and everybody else, the, the why behind the output that AI gives us, right? So that they can use it critically thinking and everything else. But I think in a very short period of time, maybe even right now that we have to fundamentally shift the way we think of how we teach and what we teach, because this is now, because now that, that knowledge is a commodity. So where are you on that? Like, because it sounds like you're diving into it right now with the way that we change leadership and that type of thing.

But on that fundamental issue, like, are we, where, where are we going? Yeah. I'm going to throw another, um, wrench into the, uh, toolbox. The buyer is also forcing the change. So I've been like overly vocal and a little bit out there on a limb and saying, going forward, I think marketing will own stages one and two of the sales cycle. Yeah. Not sales reps because, because the buyer's journey, I mean, even, you know, if you and I go back two years, what were we saying? The buyer wanted to be 55 or 60% or 65% away through the journey before they wanted to interact with the human. Well, now that numbers starts with an eight or a nine, right? Which means, you know, if you talk about AEO and GEO.

So if your website, if your company's website does not have answers, they, you know, answers to all the discovery questions, uh, the demos of products, feature functionality benefits, then they're going to move on, right? They're going to get frustrated. They're not gonna be able to find what they want. They're trying to qualify themselves in. And so what, so A, if you're a sales leader and you haven't figured that piece out and you haven't started to retrain your team on what it looks like to come in at stage three and build trust, credibility, and education in half the amount of time that you had, well, you're behind. And then, you know, so, so the buyer's using AI and it may or may not be accurate.

I was using AI and it may or may not be accurate. And so, you know, what, what I've been, what I've been writing in the book is the activity numbers may look the same or better, but that doesn't mean that things have not changed. And so if you go in Monday morning and you look at your dashboard from the prior week and you're like, you know, call volumes up 10% and whatever, and, you know, three more things were added to the pipeline or whatever. And then you go and pull a rep in and say, Hey, tell me about this deal. And they grab their computer and their AI note taker, right? And then they start just reading what the AI note taker told them, like, this is a big problem. And so the AI on our side, on the seller's side is impacting us, but almost as, as strongly as the buyer's use of AI is impacting us.

And so I, I just like, I don't think, you know, I, you know, I talked beforehand, like process, right? Like the process has to change because the buyer behavior is changing now, again, for how long? And will it be 80% or like, we can, we can, you know, we can argue that over a beer, but, but the bottom line is like, you have to be teaching, like who's like, we've never had to come in. We've always come in and built the trust and the education from, you know, from step one and built that trust over time. Well, first off now there's less trust period, trust the board. Yeah. So, um, and somebody, and somebody said earlier today to me, like, and more victim syndrome, um, um, what was me, um, but, but when you have half the amount of time to educate, develop the relationship, build the trust.

And how do you like, and so like, you're just sort of jumping in, in the middle of something who's teaching, like, who's teaching that I'm not seeing anybody teach that. And then how, you know, in asking the right questions, it's not discovery anymore is realignment questions. It's making sure like, did AI give the buyer the right information? Do they have the right information or are they coming in misinformed? And it's our job again, like to me, you mentioned challenger sale, um, before we, before we hit the record button, I think challenger sale, unfortunately was ahead of its time. I think they should re-release challenger sale with the new 2026, 2027 version. I think we need challenger sale more than we've ever needed it.

Those skills, like you said, the art of sales are more necessary than ever before. Totally. Yeah. I think it's that, I mean, you're, I'm same page, like all these AI tools for sales don't really worry me all that much. It's, it's when the buyer wakes up and realizes they don't need us. And the, the one that gives me a little hope though, is there's, you know, everybody's statistics, whatever, but, um, you know, I think you're right. 80% don't even want to talk to a sales rep, but there was one that caught my eye that like 69%, it was another Gardner one about how they use it to go all the way down. But then 69% of them want to talk to a sales rep because they need to, they, because they don't trust AI.

So they, they want to talk to a human to validate some of the stuff that they've learned. And to your point, that's where we need to jump in and figure out how to drive trust immediately. And, and the way I've been angling this is, is by actually disqualifying in some ways, like it's being like, hold on a second. Like you, we not, we might not be a good fit for you. Let's, let's try to figure that out because it might've over-promised or whatever it might be. And it's also why I, and I got slaughtered for this. A couple of people ripped me apart on LinkedIn for it when I said, I think one of the first questions we should ask is, okay, so, so why didn't, why are you talking to me? Why aren't you talking to AI and, and how far have you come down the AI path here?

Because I, that question to me, not necessarily, why aren't you talking to like, but, but more along, what'd you, let's, let's, let's elephant in the room here. You use AI before our conversation. Of course. What did it tell you? How far did you get with it? What, you know, what are your questions about it? And I'm going to meet you there as opposed to bringing you through my stupid sales process here, because that tells me a lot, right? Cause it tells me if you, if you're like, Hey, I, I, I didn't use AI at all. And you, you know, I believe you well shit. Okay. Well, that's a, you're a unique, so, so, so now, okay, now I can maybe walk you through my sales process here because you've never bought this before and whatever.

But if you're like, oh yeah, yeah, no, we've done this, I've done that and done this. It's like, okay, cool. Like now let's meet you there and figure out how I can validate. Or, or question, or give you different perspectives. Cause I'm betting it's, it told you this, right? And then it's, so how are you? You got pushed back on LinkedIn because nobody wanted to heat that scares people because they have not been prepared for that. And that's what I would be asking too. So I'm going to make some assumptions that you have done some research. You've used AI to get to where, the place we're at today. So what questions couldn't answer for you? What are you not sure it was accurate about that you want to validate?

You know, where do we go from here? And I think those are perfectly reasonable questions. You know, because it would be no different than if somebody came to you as a referral, right? Oh, Susan referred, Susan said, you're great. Oh, well tell me what else Susan said about you, me, right? I mean, how is that even, how would that be different than if somebody, if you came, oh, so you know, Susan, oh, tell me how, you know, Susan, what did Susan tell you? I don't want to repeat anything, right? That you are, that Susan already told you, but I do want to know what Susan told you. So, so with that, are the fundamentals, like, I mean, we could go curiosity, critical thinking, product knowledge, you know, like where, if you're, if you're a rep right now that was either born into this traditional model that, that, you know, you're just going through the process or you're getting into it, like, where are you focusing your time?

And then we'll talk about leadership too, but I want to, I want to get your thoughts on like as a sales rep right now, you're hearing all sorts of shit from all sorts of different things. Where are you saying, I need to get better at this in order for me to be more effective right now? I think you need to get better at critical thinking, discernment, and having a point of view that is different than what you've been fed, right? Because the AI note taker's going to pull out what it thinks is important and put that in the summary and the recommendations they're going to make as a result of that. But what I say is like, they weren't in the room. Right. People don't understand. It's the nuances, right?

It's the side glance that you didn't, that AI never saw. Now, again, maybe at some point, right? No, I mean, at some point it probably can. It reads body language. Yeah. It will be able to read the body language, you know, or it's the, you know, we, we left the meeting and walked out to the parking lot together and something transpired, but that didn't get in the CRM system. Right. Like he's like, you know, Hey, between you and me, like we're going to go through a little restructuring coming up and, you know, I think I'm fine, but you know, Jim might not be. And like, that's the stuff that makes or breaks those kinds of deals. But AI is not in the room in the way that you're in the room. If you can get in the, if you can get in the room.

If you can get in the room. Right. But I think like, I'm so concerned that, you know, again, efficiency tool, all the things, but I mean, I'm constantly like, I used AI to help me with the book and I was constantly saying like, that doesn't make sense. Like, like that's not true. Right. Like, and, or that is not what I would recommend. Right. Like that is not, that, that is not, I mean, like, you know, that is not in my voice. Right. That is not what I would recommend. I don't believe in that. I just said the opposite two chapters ago. You can't tell me to say this now. And so like, if you check your brain at the door, I mean, that's what, that's what the hiring change is going to have to be.

You know, it's when, you know, we go back to the SDR world. That is like, you know, I was like, I was the girl who was basically like, just check your brain at the door and follow the process. Right. Yeah. Early on SDRs. Right. Totally. Like just ask these three qualification questions, ask Bant, ask whatever. And then as soon as you get, you know, I would say, if you get three of the four answered right, then pass them on, you know, well, you know, now, like you said, if we can teach someone else to ask those three questions and call us as something else to do that. But I think, you know, as a leader, the other thing I'm saying is stop driving the plane. Like, so you have to get out of the cockpit.

You are no longer the pilot of the plane and get your ass in the control tower because now you're managing, like you were, you know, you were again, enablements, you know, you were doing some of that. But now if you think you're, you know, if you're driving the plane, think what you can't see, you know, all everything from like this point back, right. From 45 degree angle back, you've got to be in the control tower because things are like moving parts. You're now like the conductor. You're making sure the planes don't crash. And so the leader has to, you know, like you can't rely on your sales enablement person. You can't rely on your sales ops person. They may, I'm sure they're great. Right.

But things are happening at such a pace that, and they're not, you know, again, like those people don't have the years of experience that you probably do. Like you said, they haven't been through the battle. And, you know, there's, you know, as a leader, your strategic thinking skills should be, you should be the smartest person on the team from that standpoint. Um, but I'm so afraid that they're just, that they're, that everything on the dashboard on the Salesforce or HubSpot dashboard looks fine. And so they think it's fine until they miss the quarter big time. Yeah. So let's, let's define leadership here. So I, cause I want to ask like when you're mean leadership, you know, the C level, the VP level, and, and when they're in the control tower, what are they looking at today versus what they had to look at last year, two years, whatever it is.

So like, are you talking to C-suite, like CROs? I mean, anybody who's managing people underneath them and is doing coaching, because what I'm saying, uh, one of the big statements I'm making now is the post-mortem needs to stop and pre-call meeting needs to happen because on the post-mortem, we're figuring out what already happened. But by the time we figure that out and we figure out that our rep took the advice that AI gave them, didn't overlay any judgment and didn't go well. And again, I think the only way this is, this is an interesting thing because I've never talked about teaching objective judgment or discernment before ever. But, and then, so as I was writing the book, I'm like, well, they're going to want to know how to do that.

Like, how do we do, like, how do we teach that? And the way I came up with is, you know, there were kind of two, two things, but one was the pre-call meeting. So you're going into a call, you've used AI to prep, right? But, but what, where's your point of view? Where was it right? Where was it wrong? Where did you tell it it was wrong? Where did you decide to go a different direction? And that's how we're going to know if they're building any objective judgment or they're just copy pasting. And the terrifying part is the copy paste part. That, that's the irrelevance of the sales rep. I mean, there was a frightening thing where like a teacher in college did a pop quiz, right? And took away all the AI and all the tech and like all their, all his A students, like 65% of them failed.

And it was, so it's blatantly obvious that these kids are using it just for the answer, right? We've gone from the search engine to the answer engine and, you know, and it's a great thing for people who are curious, but it's brutal for people who are just not and looking for, right? Because those people are replaceable and, and, you know, teaching critical thinking to a kid who has not been indoctrinated into critical thinking into our society, right? Because, you know, and I'm my 15 year old daughter, thankfully we, you know, I put her in Montessori. So that's experiential, right? All the way up to ninth grade. Now she's in a private school and I'm thankfully I'm, I'm fortunate enough to be able to afford it, but they have a much different learning style.

It's going to sit here, memorize MCAS. They don't even like the SATs are kind of like, yeah, you can take them if you want, but that's not what our priority is here. We're teaching you how to be a well-rounded student, right? So thankfully I'm in a very fortunate position where I can afford to allow my daughter to be exposed to that. But the vast majority of kids right now are into, are implemented into a process, you know, and they have to pass the test and that's the, and every moment of their life is structured and then it's the MCAS and it's this. And so we've ripped critical thinking away from them. So is there a way to, to, to teach that and, and reverse engineer somebody who has been indoctrinated into this process oriented approach to life?

Yeah. I mean, you have, again, it's, it's, I say leading through questioning, right? Sort of like we've always done with the prospect. So asking, you know, asking the right questions until we get, you know, till we hit the wall. So they don't have an answer and then they have to work through it. And I'm like, and close your computer, right? Like close your computer. Like I need, you know, I need to see the synapses firing off. And the only way to do that is to say, okay, so tell me what, you know, here's the deal. Tell them to close your computer. What do you know? What do you know about the, you know, what do you know about the, you know, DM? What do you know about the influencer and the champions?

What do you know about the committee? Where, like, if it's going to go South, where's it going to go South? Right. And then, okay, so you know where it's going to go South. What are you going to do about what's the plan? Right. And they have to be able to come up with all of that. And before, like, you know, uh, on the job training, hot things, right? Like the bad experiences that you had, but when you're like, to your point, when you're coming in as a newer rep and you've not been through, you've not been through battle, you know, you don't have the battle scars, you know, cause I said, you know, I always say to people, I go, you know, you can hear it. You know, you and I know intuitively, right.

You, we hear a question and my next question out of my mouth is, so it sounds like you had a bad experience. What happened? Right. Because they're asking some things too, like something crazy. You were like, we're like, well, we don't want, you know, it was a, it's a reduced risk question. Right. Of course. In order to reduce our risk, they don't say that they just go, well, what if we did this instead? And I'm like, so it sounds like you had a bad experience. Yeah. And if you don't have, if you didn't, if you haven't been, you know, if you don't have scars, you're not going to know it. But I also think the other thing that's important that the leader, the other change the leaders have to make is I'm calling them role briefs in the book.

What's AI is like, as opposed to a job description, right? Write AI, write a role brief. And so what is, if you don't tell your reps what they can and can't use AI for and where it is appropriate to use it and where it is, where objective judgment needs to come into play or who's supposed to check it. Right. If that was the, you know, that was the quiz you just talked about with this professor, right? Like you checked it, but I mean, so AI told you X, but who over, but who checked it? Like, it wasn't right. Do those people still work there? You know, I mean, you know, did that merger go through or did it fall through? Right. I mean, like how accurate is that information? And so that that's where, that's where that control tower piece comes in.

There are so many things that I don't think you can hand off to other, to other individuals. I don't think you can hand it off to your sales ops necessarily, or you have to set up the new, like, so I get to, I'm tired of hearing the playbooks are dead. The playbook, that playbook is dead. The playbook that we grew up on, right? The SAS B2B playbook is dead, but playbooks aren't dead. Formal and documented processes are not dead. Nope. Well, and you get into that with your book, right? Like, cause you talk about, it's always funny. You always hear people say people process and technology, right? But you're like, no, no, no, no, no, stop it. Process. People. Technology. That's right. Walk me through that because I think this addresses the garbage in, garbage out problem, right?

Like AI does, you know, just, I thought AI was going to solve the garbage in, garbage out problem. Holy shit. Was I wrong? It has made it exponentially worse, right? Cause it just amplifies the shit that you have as far as your house is concerned. So how do you, let's, let's put this in context from a, from a standpoint of we're, we're all still riding the bike here. Right. And so let's Sandler's, you can't, you know, ride a bike and whatever the hell it is in a training thing, building, whatever that book is. But, um, how do you slow down enough to, to, to lay that foundation in a, in such a flux world that we're in right now. And so that, you know, that you do have the right processes while this thing is still running a million miles an hour.

MCs are still telling you that you have to hit your numbers and all that other stuff. What's your approach to building that? Like reassessing your process and starting to build. Yeah. I mean, you can, you can start with what you have, but it is the difference. And you and I know of the difference of working in the business and on the business. And I think, I think right now everybody's working in the business, but not on the business. So you're going to have to carve out time. I mean, I'm not like, there's no, there's no cheat here. Right. I mean, you can try to use AI to help you, but the bottom line is like, if you have a playbook, great feed it in and say, and say, oh, by the way, this was built for a time when the buyer started at zero with us.

But that's not the case. So like, what's changed, right? Feed it in, look at your process. What's changed? The buyer and how the buyer is educating themselves and gaining information has changed. Some of the, some of the people that are working for us have been brought up in a different world than we were brought up as, you know, older individuals. Tools don't look like they looked before. And every day a new tool pops out. And so first off, like, is the process even make sense for today's world? Which probably doesn't, by the way. So, so how do I need to update the process to make it adapt to what's the reality of today's world is? Then people, who do I need to do what? Like, what can't be outsourced, so to speak?

Like, what has to stay in-house can't be outsourced? What does that look like? What are those boundaries? What, what tools are they going to be able to use? And then, okay, what's left over can be managed with tools process or tools, AI, you know, on top of that. But the boundaries that have to be set, like, it's so funny, like, for those of us who've been through therapy for years, you know, I've been talking about boundaries for a long time, but not in the way that we're talking about them today. And I was like, I was like, finally, people are speaking my language. It's the same, right? Yeah. Like, what are we not going to allow AI to do? Yeah. You know, when are we going to, when are we going to gut check something?

But I just, I'm so concerned that, and then this, you know, again, like the postmortem to pre-call meeting, right? That seems like a really easy shift, but it is, but it does up, upside down how we've always done things. We've, sure, we've had, you know, deal review meetings and pipeline review and deal strategy meetings or whatever, but you have to ask different questions now. You know, it's not what's the agenda for the next meeting. You know, it's, you know, where could this go, where could, you know, where could this go south? They're doing, and again, like the other, the thing you, the thing you have to figure out is, like you said, starting with the, like, so what have they done? What have they used AI for?

Because everybody's using it. And then it, that could be like a, that could be, it could be on a collision course. Yeah. I guess for you now, what are those questions? You know, it's like, where could it go south? Like, I want to, I want to. What did AI tell you? Yeah. And what information, what are you taking? What, what pieces are you going to take into the meeting? What pieces did you reject? And I think that's how we're going to teach objective judgment, which is it gave you all this and gave you, it gave you the executive brief, right? It gave you the agenda, it gave you the goals, it gave you the outcomes, it gave you all the things, but where did you disagree with it? Where, what are you not going to do?

Where did you push back on it and say, yeah, I don't think we're ready for that. Like, I don't think I can ask that question in this meeting. I don't think I've built enough street cred yet, or I don't think Judy's really the person I should be talking to about that. I think I should have a private conversation with Jim instead of doing that in a group setting. And so like, you're going to get the exec brief. You're going to get the advice, but my question as a leader is like, what aren't you going to take? What pieces don't you think make sense at this point in time? Because if we just start following the script, then we are checking our brain at the door. And so, you know, and I think those are the questions like I'm running, I'm running candidates through an assessment right now.

So, so first off, I'm like, forget about the role play and the shit that you used to do with the final interview or whatever, because they're going to use AI to do all that. So I'm doing it live and I'm giving them a scenario and I'm saying, you know, mute yourself, go off camera, run it through AI and then pop back on. And they do. And I go, great. Show me your prompt. Right. What did they write? And then I go, okay. And I go now go change whatever you want to change off camera, come back, you know? Okay. Here's what I pushed back. You know, I want to see, are they doing that? And I can do that live. I can test for that. I can check for that. Especially now. Yeah. Again, no longer am I giving.

The first couple of times I did it, I like gave them the thing and then had them come back to me. And I was like, no, no, no, no, no, no, no. How many times do you think they redid that prompt? Exactly. Yeah. I mean, and again, like it's, it's a time test. Like you can't take an hour. Right. I'm like, you know, how, how quick can you give it instruction to get the things that you need to get and come back? And so those are kind of like, no one's like, I don't know anybody doing that yet. You know, a lot, like a lot, right. I don't know anybody who's testing in that way, but I like, and I'm not testing for AI skills. I don't care what tool you use. I want to know, you know, can you give it clear instruction?

Cause like, like I go back to my, you know, my kids out of college, my zillennial friends and I'm like, it's text talk. Right. And so like, can you write a real comprehensive, because again, the information you're going to get back is only as good as what you've asked it to tell you. And so like, and so like, if you're half baking a prompt and you're not giving it enough information for it to come back with a reasonable agenda outcomes, whatever, like, and then that's, so it has to start there. So I've got to see, like, can you even write, if I give you, this is the case study, like this is your, like, either you're in the middle of this deal and here's what you, here's what I, you already know, copy pasted into AI, I don't care.

Or, you know, here's your target account and you're, you know, you're getting in their first, you know, first meeting. Like, I need to know what they can do. And so we're just doing it in real time. That's cool. Yeah, I think, and that's, again, it kind of goes back to the concern though. It's like, I think that's, that's fair that it'd be, it's interesting to see, you know, who adapts, who, who adapts to that. Because mid to senior reps should be able to apply critical thinking, call bullshit on it, right, with all their context, the junior ones, you know, who don't know that context should be able to use AI to figure it out the right way, right? And ask it, like, just be curious with it. But I'd be, I'd be interesting if you could do like a full big study of that, of that test to see how many people basically just took a very generic prompt and put it in there and came out with AI slot versus ones who sat there and really kind of beat it up and thought about it, didn't even know what you were really asking, but asked enough questions to figure it out, you know?

Because I bet, I mean, I'll go back to Pareto's rule, right? Like probably 80, 20, and I'm going to be generous with that because that's, because that's where I'm at right now. Like I am insanely optimistic for people who are curious and creators and, you know, you don't even have to have business argument in context as long as you're fucking curious. I am insanely optimistic for you because that you have, we now have a tool. That when used right, can literally answer or do anything you need it to do and give you any insights that you need. But if you don't, and if you're one of those B players, that's just standard, like, I just want to do my job, punch in, punch out. And I don't want to cause any waves here, man.

You are fucked. Like hard. Yeah. I want to make sure that I, um, I have four, uh, core skills that I think sales leaders are going to need going forward. I want to share that with your audience. Yeah. I was going to get into the rest of this, like, cause leadership I think is, is more important now than ever in this world of AI and guiding the rest of the team through it. So what are those, what are those pillars? First thing is systems thinking. Okay. So the ability to, this is the control tower thing, right? So the ability to see how the parts of the sales motion are all connected and then when it, how it's going to, what would break, right? What breaks when one, when one thing changes. Um, number two is workflow design.

So again, the ability to map and build and then monitor how the work gets done. Remember when we had humans, it was one throat to choke, right? So, I mean, that's the other thing that, that I haven't shared with you yet is that really got me thinking is when, when a deal falls South, if a deal goes South or, you know, like just completely gets a close lost and AI was involved. How soon, how soon before you think we hear the rep say, well, but I was just following the instruction or the advice, right? So where does AI, so workflow design, where does AI fit into the motion and where does it have no business being decision leadership, which is the word I kind of came, I didn't know how to describe it, but you know, how to make clear and timely calls that model the behavior for your team where data, as you mentioned, the science of sales is everywhere where data is abundant, but clarity is murky.

So like, you know, as, as the leader, if you're using AI to make decisions, are you overlaying judgment? So like, you know, how do we make decisions? Like you're going to have to have conversations about how we make decisions at this organization or on our team. How do decisions about how to move forward and what next steps look like get made? Do they get made because AI told you or they get made because you took information that AI gave you and then made your own decision. And then we've talked about it ad nauseum today, coaching objective judgment, you know, and it needs to happen. Like we've never talked about it. It's something that has to happen. And then the boundaries, the boundary setting, which I'm calling accountability clarity.

So, so when something doesn't go well, whose throat are we choking? Right. I mean, when, when, when you got bad advice because you wrote a bad prompt or you didn't get whatever, and then you took that bad advice and the deal fell through, it's still like, it's still your fault. It's still your fault. Right. The accountability still at the end of the day lies with the human. Yeah. It's funny. It's, it's funny you bring that up because I, you know, I use AI to prep for my podcast, you know, give you the insights and all that other stuff. And there's, there's been a couple, uh, which is why I've had to redo my prompts quite a bit because there's been a couple that have like phantom pulled like history shit as far as like school and different things that people have done that is like, so like, it's almost like, oh yeah, okay, cool.

Like, thanks for, thanks for finding that. That's interesting. Right. So it wasn't something I would even consider spot checking because it seemed like, oh, that's it. And then like midway through the fucking interview, I've done it a couple of times where I was like, oh yeah, I remember where, you know, I read something about how you did this and there's like crickets and they're like, uh, that, that's not me. I never worked there. I never did that. And it's like, oh fuck. I'm like, my bad. That's not, Hey everybody. There's an example of AI fucking up. Not working in design, not working in design. Yeah. And me not. It's just the simple things we've always done, right? Like, uh, again, like, uh, I do a ton of hiring.

We talked about that before you hit the, uh, play button. We do not use AI to resume review. Really? Like my, yeah, I've, I've just started a new client. It's a, uh, it's a strategic enterprise account executive role. She's coming up. She actually lives here in St. Louis. She's coming to the house tomorrow and we're going through resumes together. She doesn't normally does resume review, but this is a higher, uh, target, uh, candidate and client. And so we're going to go through them together and I'm going to teach her why, like, nope. And here's why. Yes. And here's why like old school coaching, sitting next to someone that's actually sitting next to a human. But, but even like, you know, one of the first things I taught her was like, the first thing you do is go compare it to LinkedIn.

And then like, and note all the discrepancies, right? Because, because if there's too many of them, then I'm just going to red flag that we're going to put that in the no pile. And if not, if there's some little things like, Hey, there's a, you know, year and a half job gap on one, but not on the other, like just going to come up on the phone screen. And, you know, so I mean, it's like, it's just like, again, you and I've been, you and I just, you know, we, we were analog. Yes, we were. But I mean, they're just, but they're just not, but I'm like all of those things there, there's just some things that are so simple. That, but like, I wrote a post last week that, you know, how many people are using, and I won't, you know, we won't name names, but how many people are, how many leaders are using AI to coach calls?

And just sending over in this, the summary report gets sent over, you know, not, I mean, you know, and then after, after three or four of those, the rep is like, yeah, same feedback. No, like that doesn't tell him that's not coaching. Right. That's just an administrative. That's, you know, so it's like, I'm worried about us abdicating the, the art of sales. I mean, like the science of sales has already become the 80. But, you know, think about all the things like, again, you know, we used to sidejack. I mean, literally, right. I plugged into the phone. I'm so old. I, we, I like rolled my chair over to the person. How awkward was that? That was like, like reps have no idea how, how like horrible that was back in the day.

Your manager literally rolled their chair, sat next to you, like knee to knee, plugged into your phone and went, put their headset on and literally listened to you live, like torture. Right. But, but I mean, like, but how much faster and better do people get when we did that? That's the osmosis. Well, I don't, so this is the thing where I'm, I'm a little conflicted on the coaching piece of it because yes. And right. Good coaching. I think a good human coach is better than any AI could ever be just because of the nuances, because of the connective tissue that you have just human to human, right. But we all know that managers, you know, the number one thing they should do is coach, but that's the last thing that they actually do because they're never given the time to the resources.

And look, we can all look at, you know, and I want to pick on Gong, but you know, and I know they've updated. That was the, that was the company I wasn't going to name. So, but that, that's the one where like, you know, their original value proposition. Oh, well you can just skip to minute 22 because when they talk to it, no, no, no, no, you really can't because what they said at minute five is probably what dictated what came out at 22. Oh, well you can listen to it at 1.5 extra. No, you can't because tonality, inflection, all that stuff matters. Right. So, so that's why I like to really do coaching, right. You have to listen to that 30 minute call. You then have to put at least 15 minutes into thinking through and whatever it is, and then you have to deliver it to the rep.

So, and by the way, coaching is subjective, right? Oh, so now in the world where, look, you and I grew up in the sense that I wanted the harsh feedback. If somebody told me I was a fucking asshole, it was like, okay, thanks. I need like, okay, that sucked, but appreciate it. I learned better. This generation is not like that. They are almost like they have an allergic reaction to feedback. And if I don't think you like me, it doesn't matter how good your feedback is to me. I'm always going to put up a wall and say, well, that's just because Christy doesn't like me. Like, like I'm, then I'm going to go to HR and then you're going to be like, okay, I'm never going to coach anybody again in my life.

It's just, yeah, John, you're doing great. You know? So there, I do have some hope that, that the AI coaching tools have a place because it's in a safe environment, you know, role play scenario, given that type of stuff. But there still needs to be that human to oversee it, just to make sure that that is being used even in the right way. Right? So it's not just, you've got a coach now as a sales coach, as your AI thing, it's, it's going to coach you on these super tactical little things to prep you for a meeting or whatever it might be. And give me insights as a leader of what your actual issues are so that I can step in and have that real conversation with you. So that's like the best case scenario, in my opinion, because I don't think it's all one or the other these days.

I think there is a place for it. It's just not too out to your point, like checking out your brain is the same thing with checking out your coaching. Like if you sign up for an AI coaching tool, it doesn't mean it's like, okay, check the box. My reps are now coached. Well, that's the problem is, I guess my concern will be, it's the same thing as writing a bad prompt. Right? Because if you can't customize that to the point where, you know, again, how you've been, you know, you were taught MedPIC or like, you know, you were taught MedPIC or you've learned these things from past, like, I don't know. I would say jury's still out for me. I'm, I'm, I'm, I'm encouraged by your encouragement, but I would say jury's still out for me because I think, I think we need human coaching more than ever before because we're going to need, and I'm like smarter reps.

Like, I don't know how else to say that. Like the people we hire are going to have to be smarter than the last generation because like the process is so different. Like you could really teach the process and like, chances are like, again, with the 80, 20 rule, things will happen at each stage. Like this is probably where you're going to get this objection. But now, like depending on what tool the buyer uses, where the buyer got educated, all the things like you could be, I just think the surprise factor is going to pop up more and more. And if you can't think on your feet, I mean, think how many, I mean, we were taught, we were like, we were taught to think on our feet. Like I, I used to coach, it was funny that you say, when you use the gong example, I literally like, and I've still, and I still do this occasionally is I will take the recording and I do, I call it the stop, the start, stop coaching methodology.

I just start playing the call and I stop and I go, do you remember the question you asked or what you said at this point? And they go, yeah. And I go, say something different. That wasn't that what the way, what you did wasn't right. I'm not going to tell you the why it wasn't right yet, but like, if you had to do it differently, what would you do today? And I, that's how I taught reps. You know, I would say like, like they answered that question, but there were three more questions just like off their answer. I call it the question on the question technique and I go, so they answer the question. Now ask the next question. What's the next question? And then I would answer. And then I would say, great.

Now what's the next question? I mean, and that's how I coached. I mean, I got real down and dirty. I don't think Gong's going to do that. And I, and I think to your point, I think the, the human component, I think human coaching is going to be extremely critical for one reason. And one reason only, well, not only, but it's because we're dealing with humans. And, and I think until, you know, until it, look, when AI starts buying shit, fuck, I, you know, I'll see you in Costa Rica. Okay. Cause then I don't know what to tell you. Right. But as long as there's a human on the other end of that, like no AI is going to be able to replicate the human connection in the, in the sense of how do you relate to somebody?

How do you, the nuances and those types of things, it can tell you, but until you experience it and, and, and sit with it, you're not, you're not going to really ever make that connection to a AI avatar that's telling you what to say. And so that's, that's where my hope is, is I actually think the, the only thing that's going to slow down the replacement, like the legacy seller being replaced is actually the legacy buyer, because there are a whole bunch of people in the buyer side of the house that their job is to evaluate three vendors, to do this, to do that. So they're going to push back just as much as the sales reps are going to push back because this is my job. Like my job is to evaluate three vendors.

Now you have a button that can push it and get, you know, send out RFPs and evaluate them and make a decision like, no, no, no, no, no, no, no, no. So I think that that's going to be the balance here is the legacy human factor is going to hold on for a while. My only fear is like when like my daughter, for instance, who is like AI native at this point grows up into this world. Like, what does that, what does that look like? And I can't think about that or else I can't think about that right now. I have to go smoke a huge joint and not panic about that one. But she'll be in good company. She'll be in good company. Yeah, right. She won't be the only one out there. Nope. And like me, she might even be just down with me in Costa Rica doing the thing.

So that's where it's at, John. Yeah. These days. So Chrissy, when's the book coming out? Hopefully by October, I just got the first cover design and the proofreaders got their hands on it. So I'm going to get this out in October. All right. Fantastic. So for people who are looking to find out more information on coaching and all the wonderful things that you're doing, where do you want to send them? Please reach out to me on LinkedIn. One of the things I love is if you're going to connect with me, drop me a note and tell me what your one takeaway was from our conversation today. I always like to hear what resonated. Love that. And for people who are listening, we will put this in the show notes, but it's Christy with an I-E, K-R-I-S-T-I-E with an I-E.

So go look her up on LinkedIn. She's all over the place, putting out awesome content. So Christy, thank you so much for joining. It's always a pleasure talking to you. Thank you. This is my own therapy session, by the way. So we talked about therapy beforehand. I use my podcast as therapy because I just talk about it out loud. So thanks for sticking with me on this one. My pleasure. No invoice in the mail. Don't worry about it. This one's on me. We both, we both needed a, we know if you needed a conversation. Love it. All right. Well, everybody, I hope you enjoyed the conversation as much as I did. And like I say at the end of all these podcasts, go out there and make somebody smile today. Because no matter how bad your day is going or how bad you think it went, if you make somebody smile, you know you had a good day and the world needs a lot more of that right now.

So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2 if you've already gone through my training or sign up for my newsletter. Any of those will help ensure I can continue to bring you free content and great conversations like the ones you just heard without having to annoy you with sponsors. Again, let's make it happen in 2026 together.