Why AI Will NEVER Replace Real Sales with Jeff Kirchick

Speaker A: 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 guess who I truly respect and I think make a positive impact on the world around us? I guess this week had a high school wrestling coach who told him that anytime he was about to go get crushed in a match, that he should bring a bag of sticks with him. Which sounds a little odd, but the logic behind that was when a snake is suffocating you, if you break a few sticks, sticks, the snake thinks it broke your bones and loosens its grip. That coach taught Jeff Kirchik that none of this matters as much as we think it does. And he has built his whole approach to selling on it ever since. Jeff wrote a book called Authentic Selling six years ago that called the Rise of AI and Go to Market, and he is now the VP of sales over at Zoro. We got into why he ripped gong out of his stack and built everything in house, why he does not believe AI is killing the SDR and has only raised the bar on what spam looks like. And the question behind his next book, which is simply, why haven't you done that yet? So I hope you enjoyed this conversation as much as I did. Let's make it happen. Jeff Kirkchick. Welcome to the Make It Happen Monday podcast, my friend. How you doing?

Speaker B: I'm doing well. How about yourself?

Speaker A: Doing all right, man. I'm looking forward to this conversation, first and foremost, for some of the stuff that you're working on these days in the world of AI and how you're doing your own internal stuff and building some cool shit, ripping out some of the software, but also just because you're a Boston kid and I, we can have just a real conversation. And I always love having conversations, uh, with Boston kids, so.

Speaker B: Yeah, well, maybe we'll get. Maybe we'll get to the Red Sox at some point.

Speaker A: During this conversation, I saw the intern. I saw that coming out of school, too. Right? You were on a field. What were you on the field there

Speaker B: for the grounds crew? I worked. Uh, yeah, it was a pretty unglorious job, but it was, uh, it taught me a lot of things, so it was fun.

Speaker A: Awesome. Well, let's, uh, let's do this. So before we get into all the cool shit that you're working on right now and kind of what your. What your thought process is for, where things are going, um, from an AI standpoint and how you, you know, you called it about. I think you said you called it about six years ago in your book. And then, you know, today you think it's pretty overhyped in a lot of ways, specifically as it relates to sales. But before we get into that, uh, let's go back to the career arc, or not even the career arc, the kind of what made you you. Right? So growing up in Boston, parents, influences, that type of stuff. I saw you had a really cool high school coach that was pretty direct and no bullshit with you, uh, from a wrestling standpoint. So talk us through a little bit about growing up here and uh, then we'll get into the career stuff.

Speaker B: Yeah, well, first and foremost, I was a very fortunate person. I grew up in a, you know, relatively wealthy town and went to a, uh, very, you know, highly regarded private school and um, you know, Princeton for my education, you know, for college. So I acknowledge that I kind of had a lot of advantages growing up, but I m think that really set the stage for a lot of things. Uh, and in my high school, the motto of the, one of the mottos that was on the walls in the school was like, from those to whom much has been given, much will be expected. Um, I think it's a verse from the Bible or uh, somewhere in the Bible. And uh, I'm Jewish so I haven't, I haven't read it, but it's what I hear. Uh, but uh, but um, that's something that stuck, that stuck with me my entire life. I mean I've always felt like a need to try to give back and help other people. And um, it's always been like my long term goal, whether it's through like some of the mentor, mentorship stuff I do on the side or coaching and um, or just like in my personal life, like a big brother, big sister, things like that. But um, I think the reason I've gotten into entrepreneurship is because like I want to be a founder that, and maybe build a company that somehow gives back to people. And I think, you know, writing books is another way that I've tried to um, to do that as well. Um, but yeah, I mean I grew up, I think, I guess you could say, maybe with a little bit of a chip on my shoulder. I've got like an overachieving older brother who, who's written like best, uh, selling books and stuff like that and kind of grew up in his shadow. Um, and I've been very competitive. I played sports my entire life and uh, wrestled in high school and parts of college. As you pointed out, one of the main influences in my life was my high school wrestling Coach, his name was Steve Ward. Um, he was a very, let's face it, authentic person. And my high school was very much like, all these kids that were jockeying to get into, like, Harvard and Princeton and Yale jail and, like, competing with each other to get into these schools was a little bit, like, cutthroat. And, um, the thing that I think was the most important lesson I learned from him was that, like, none of this really mattered. Like, he.

Speaker A: He.

Speaker B: And he would tell it to you straight, like, you were taking yourself a little bit too seriously. And I think the best example of this was, um, he told this story. If you were gonna get crushed in a match, like, if you, um. If you were going out against an opponent that was just like a really, really, like, just, you know, amazing person who's going to kill you, he would tell you to bring a bag of sticks with you. He would call it a bag of sticks match. Because apparently when snakes are, like, killing people and they're, like, suffocating them to death, if you, like, break sticks, the. The. The snake will think that it, like, broke your bones and it will, like, loosen its grip. And so he would. He would literally say, like, hey, it's a bag of stick. Bring your bag of sticks with you, because you're about to get, like, suffocated like a snake, right? But, like, that was kind of the. You know, I contrast that experience with when I went to college. I walked on to a Division 1 wrestling program. And I remember, you know, I had to wrestle against this kid named Frank Molinaro. Um, and Frank Molinaro ended up being a national champion and a bronze Olympic medalist.

Speaker A: Oh, shit.

Speaker B: And my coach didn't tell me any of this. He was just like, hey, like, you know, go out there and do your best.

Speaker A: Good luck.

Speaker B: And by the way, this is a great coach. Like, you turn the program around. But I just wasn't cut out for it. Right? But just that, uh. Now just the approach in the mindset, just like, hey, you're going to lose. So, like, just go out there and, like, go for broke, right? That was another expression that he had. So that's been kind of the way that I. I try to. I try to. That's the ethos that I try to bring into the world, um, is authenticity. And, um, as you pointed out, with all the stuff about AI that's been coming out, you know, six years ago, I kind of. I felt like I saw this trend coming. And, um, I also had my own personal experience and, like, going out into selling and building these relationships I had been fortunate to close, like, very large multimillion dollar contracts with, you know, big, big companies. Um, but I hadn't never really been given any formal sales training. You know, I wasn't following, like, these robotic processes. I was kind of just like, using intuition and empathy and, um, you know, I've kind of worn my heart on my sleeve, you know, in my, in my entire life. And not always a good thing, but in selling, I actually think it can be a very good thing in terms of building trust that people will, like, grow to trust you. And I wanted to write about that. So that was my first book and it was about how you will never be able to replace that and how, if anything, I will actually augment, um, the importance of that skill for sellers. Because there, there is going to be some displacement and it's already happening, right? And I'm not, I'm not saying I'm not one of these, like, AI truthers that thinks that like, AI sucks or I actually think it's wonderful. Y. Um, there will be displacement and it's already happening. And so for human beings, we need to start leaning into what makes us unique. Um, and that is shared experiences and a soul, you know, and all that. So that's a little bit about me and like, what I'm all about and, you know, where it all, where it all came from.

Speaker A: And do you think that there is something about where, you know, growing up in Boston that kind of gives a, um, makes it a little bit easier to be authentic in the sense that I feel like Bostonians or East Coasters, but specifically Bostonians are kind of like the no bullshit, go yourself. If I don't like you, I don't like you. If I do like you, I do like you. Because I remember growing up in, in Boston. Well, not, you know, Bedford, right? So a little suburb. But, you know, when I went down to Maryland University, I went down to University of Maryland and I remember, like, I'd be having conversations with people and I thought they were genuine, good conversations. And then later on I'd heard that person talking my back or something like that, and I'd be like, what the. Like, if you don't like me, just tell me you don't like me. I don't give a right. And I remember coming back to Boston and I didn't. I ran away from Bedford. I didn't run away from Boston. I ran away from Bedford because it was a small town. And, um. But when I came back, I had the opportunity to work for Dewalt and It was either Jersey or Boston. I'm like, can I live in the city? And they're like, yeah. Because I'd never lived in the city. I'm driving around in my Dodge Ram pickup truck, right, looking for a place to live. And I obviously was kind of distracted or something like that. And I cut somebody off. And all I hear out the windows, get off the road, you dick bag. And I was like. And it like, felt like, very, like, not. I'm like, you know what? I'm home. I'm like, that. That was my fault. I deserve that now. I had to roll down my window and give the obligatory go, fuck it, you know, that type of thing. But I just felt like this feels a lot more like, natural to me as far as, like, being upfront and direct with people and that fine line between being direct and being rude. But do you feel like that's a regional thing here, that. That you've experienced here compared to other places?

Speaker B: I do actually have a couple of things to say about that. So number one is, yes, I agree with you. I mean, I grew up in the suburbs of Boston, and so people that are really from Boston would technically say, I'm not from Boston, I'm not from

Speaker A: Boston, I'm from Bedford, but nobody knows where Bedford's from.

Speaker B: But I've certainly been around. I mean, and I'm a die hard Boston Bruins fan. And I think for a lot of people that are not from Boston, they don't understand. I mean, if you go to a Bruins game versus any other team in Boston, the authenticity of the fan base, I mean, it's really unlike any of the other fan bases. They are really into it in a way that's unparalleled even for, like, Red Sox fans. And, um. And I think that, you know, people don't even realize that the biggest rivalry in Boston sports, they think it's Red Sox, Yankees, it's really Bruins, Canadiens. That's been the case for a very long time. But I think, you know, being exposed to that and being exposed to these, like, truly authentic people that come in from the North Shore to go to a Bruins game, seeing. I mean, I've been going to Bruins games for a long time. I love that, you know, and I think that what I've always loved and appreciated about it is that these are really. This is who these folks are, and they love it. And um. And so, yes, and I think, you know, when I came from this, like, small boys high school and. And then I went to Princeton and I think honestly, the Dichotomy between the two was. Was pretty stark. I mean, you know, some of these kids, a lot of these kids I went to school with, were really just doing whatever they could to climb the social ladder, um, at the expense of being, you know, intellectually honest or good people or nice people. And I think I had a lot of resentment about that. I wasn't really prepared for that. And it made. It made college actually a pretty experience for me. So I think seeing that was tough. Um, but, you know, to your point about the guy who called you, uh, you know, a dick bag or whatever he said. So I'm about to say something that's a little controversial, but I actually think that that makes that person a little more endearing on a sales level. Right. And, like. And so when I talk about authenticity, what's really important is that you don't need to be liked. You need to be trusted. You trust people that are being an honest version of themselves. And so one of the examples that I've always really liked giving is someone like Dennis Rodman, who is a weird guy, but unlike a lot of other weird people, he's not acting. That's actually just who he is. And if you watch the documentary about him and he had a weird upbringing and a tough, you know, tough life growing up. And I'm not advocating for this, but if there's North Korean dictators, the only person that he wants to be friends with is Dennis Rodman here. I, um, don't know. We shouldn't be friends. Just be clear. I'm not advocating we should be friends with, like. But there's something to be said for the fact that, that, that is the one person that's been hand selected. And it's because this is someone who is an honest version of who he is. Right. And so. But he's a perfect example because he's also not, you know, he's done a lot of, like, things in his life that are not great. I mean, that being one of them. But like, um, you know, he's kind of estranged from his daughter. You know, he wasn't really a great parent. Um, so I'm not saying like, oh, he's a good person. But what I'm saying is that on a level of sales that, like, if. If someone, if someone was saying something to you, would you believe it or not, authentic people are the ones that you end up trusting.

Speaker A: Absolutely.

Speaker B: Um, so that. So that's, you know, to your point about the guy who said something to you, that. Yeah, that is authentic.

Speaker A: Exactly. I mean, I think that. And it's funny, like, the Bruins, you don't realize that it's a Bruins town. I didn't. I knew because I didn't grow up a Bruins fan. I grew up a Celtics fan. Sure. Um, my wife grew up a Bruins fan. And, uh, I didn't really realize how much Boston was a Bruins town until they won the championship. And their, um, parade was bigger than anybody else's. Like. Like, even the Red Sox, the first time they won the World Series, the Celtics, the first time they'd won in however many years. And the Patriots and all that stuff. The. When the Bruins won the city. Shut the fuck down. And everybody went to that. And it was just one of those, okay, yep, this is a hockey.

Speaker B: Yeah.

Speaker A: Um, but to your point, like, just growing up around that, that's why I still think Good Will Hunting is still the best Boston movie. Because that first. You remember that opening scene where he's like, oh, I remember you from kindergarten and just fucking Wales on the kid. I'm like, I've been a part of, like, that two or three. I haven't been the asshole, like, throwing the punch, but I've been part of the friend group that's better. I'm like, God damn it. Like, do we have to do this? And then just getting into it. But I think there is something about the scrappiness. Uh, and also, you said chip on your shoulder. Right. I think there is a chip on our shoulder here in Boston compared to New York, because everybody thinks East Coast New York. And, you know, we're like, he, yeah, go for it. So let's pull on that thread with authenticity, though, because I think that's arguably, uh, going to be an even bigger superpower moving forward when everything is fake. But how do you. It's such a balance because you said you didn't really fit in in Princeton. Right. And that climbing the corporate ladder. I never really fit in in corporate America, quite frankly, because I could never figure out how to play the game. You know what I mean? Like, the kissing ass and, you know, doing the thing, and, like, I just can't. I got fired from, like, when my little company, Thrive Networks, got bought by Staples, I got fired from Staples because I couldn't keep my mouth shut. Like, I literally called everybody. I'm like, what are you talking about? Like, this is ridiculous. Right. And that didn't go well. So there's that line of authenticity. Right. Which I think has helped me a lot in my career, but also I think it's hurt me a lot in my career because I. I don't have a filter in a lot of ways, and I can't play that course. So I have. That's why I work for myself.

Speaker B: So.

Speaker A: So if you're, you know, with kids who didn't grow up with kind of authenticity around them, if you will, um, and now in this AI world, and how are you coaching your teams to. To. To be authentic and leverage AI the right way so the authenticity comes out versus regurgitating whatever that AI is telling them, whether it's an email, whether it's a question to ask, whether it's a meeting prep or whatever. How are you coaching that team to figure out what that balance is?

Speaker B: Yeah, it's a great question, but I think I've got a little bit of a cheat code because the industry that I'm in happens to be intensely competitive. And so in a way, like when we meet, so we sell through all through channel, we sell through benefits brokers. In a way, we're benefiting, no pun intended, from the fact that we're not the only vendor that they're speaking to. There's a frame of reference for them. And the thing that we sell is not simple or easy, and it comes with a lot of challenges. And so I think when we're honest about that and we really lead off with, um. And actually someone, I don't know if you know, Todd Capone, who wrote. Oh, yeah, of course, you know, he. He talks about this all the time. He wrote that book called the Transparency Sale. And like, you know, he talked about going into the meeting and telling them all the things that they couldn't do and how it made that client, you know, really want to work with him because they believed him on everything he could, you know, and everything he could do. Right. Because no one ever does that. No one starts the meeting by saying, oh, yeah, all these things you want to do, we don't do them. You know, that's not normal. But in a way, it actually works quite well for us because our competitors are. And I'm not knocking anyone specifically, but I think what we're hearing in the market is that our competitors are probably saying that, oh, it's not too hard to do this, it's not so bad. And we're kind of like, no, it is pretty hard and it is. It is going to be pretty challenging for you, but, like, this is the expertise that we'll give you to help you. And, you know, eventually it'll get easier and whatever. And so, I mean, I literally posted on LinkedIn last week I found a. You know, one of my sales reps tagged me in a trans, probably because he wanted to brag about it. But, um, the broker, literally, she said to him something like, um, you know, I had only blocked 15 minutes for this because I don't like talking to you guys. And, uh, you know, I didn't know if I was going to give you another 15, but I'm going to do that. And he said, oh, okay, well, like, why are you giving me the extra 15 minutes? And she said, because you, because you're not trying to push me. And you, you're, you're being honest with me and you're trying to meet me where I'm at. And, um, that, to me, like, if I can make every customer feel that way as a leader, like, if my team can do that, then, like, I could just sit here and do nothing, right? Like, that's like, that's really, that's really what I want. That's the best compliment that I can get is actually them getting that compliment. Um, and so that's what I'm trying to do is like, hey, just. It sounds really simple, but it's. Just go be. Just go be honest, please. And like, um. And, uh, and. And don't try to. I, I talk to them about Buddhism. Okay? So, like, I know it's a little weird. I don't want to sound like a weirdo here, but I talk about Buddhism and let's say, like, the deal doesn't matter. Like, whether you close the deal or not, your life is going to go on. There was life before it, there's going to be life after it. Think of yourself zooming out from yourself, like off the planet Earth. Like, you are literally a speck of dust. And so if they can det. And they all make fun of me, they're like, oh, Jeff just thinks we're specs of dirt. He doesn't love us, or whatever. But I'm trying to get them to place less importance on these interactions because by doing that, they free themselves of their agenda and they can just be honest. And when they're honest, even if the customer doesn't like everything they're hearing they're doing. The thing that I talked about before is they're building trust. People want to work with people they trust. Um, so that's. That's what it is.

Speaker A: I love it. Have you ever seen, uh, Men in Black?

Speaker B: Yeah, of course.

Speaker A: The end scene where they zoom out, right? And it's the marbles. And then all of a sudden it's the aliens. I used to kind of bring that up, too. It's like, look, we're really at the end of the day. It's also why when I go on holiday, um, or whatever, I'll put on my out of office. Uh, thanks for your email. Uh, since I'm not an emergency room doctor, I'm pretty sure your email can wait until I get back. Don't forget to smell the roses. And it's basically like, I do sales. Sales training here. Like, nothing that you need from me right now is an emergency. I prom. So, yeah, no, it's.

Speaker B: It's a. It's a good thing to remember. And I'll be honest, I'm the victim of my own, you know, thoughts. Sometimes. I. I forget that. And I, you know, I think my wife had to tell me at Disney World, you know, it was in the middle of our busy season. We were there last year. She's like, you know, you're replaceable at work, but you're not replaceable here. You know, I was like, okay, well, that's, you know, pointed comment, but it's also true. And, um, so it is. It is. Even for the people like me who are teaching it. You know, sometimes it gets very easy to lose sight of the fact that what we're doing in the grand scheme of things usually doesn't matter that much. And the things that do matter, uh, are, like, spending time with your kids. Right?

Speaker A: So, yeah. Yeah. So are you. So when you hire right reps, are you. Do you have a certain hiring profile, or did you find yourself having to almost deconstruct, uh, somebody from not being authentic? Because a lot of sales reps come from a person. Like, I got to say all the right stuff. I got to be the perfect thing. Right? And even in interviews, I got to be the perfect interview. I got to say the right thing. So do you find that you have to kind of break people down to. To stop that. That facade, if you will? Or, uh, do you have a very specific hiring profile that you look for so you don't have to break them down and kind of reverse engineer the authenticity?

Speaker B: Yeah, so it really depends. I don't know if you can hear my screaming toddler in the background, so she's, like, in a different floor of the house, just so you understand how loud she's being right now. Um, but, uh. But, yeah. So, um, the answer is, yes, I do it. Every role is different for junior roles and more senior roles. There's different things I care about. So, like, for SDRs, I literally look for two things. It's work ethic and coachability. I literally the only two things that matter. Um, and the coachability piece just comes from me, like ripping apart everything that they do throughout the interview process and just seeing a, whether they handle it well. But the most important thing, because a lot of people are trained to like, handle feedback well. They know they're being coached that like, you need to handle feedback well. But there's a difference between just handling the feedback well and actually then incorporating the feedback and coming back with a new draft that use the feedback. There's a real difference between the two. Uh, so, so that is like how I can really understand coachability. It's not just you told me thank you for the feedback. It's that you understood it and you used it and then you came back to me showing me that you understood and then if you didn't understand it, that you asked me follow up questions so that you could get it right. So that's how I know coachability.

Speaker A: So do you run scenarios on that? Like, because I used to, with a cold call, like, I would give a kid basic, you know, what'd you sell? Okay, I'm going in the other room. Your goal is to get the meeting with me. That's it. And then I would come back and I, uh, would give them feedback and then I would say, okay, now you have to sell what we're selling. Same scenario here, but now you don't know enough. But you still go. And all I cared about, I don't care how good they did on that first call. They could have aced it or bombed it and they could have aced or bombed the second one as well. But as long as they showed the incorporation of my feedback into it, I was like, okay, at least this person listens and they're coachable. What are some of the scenarios you run people through to see to understand coachability?

Speaker B: Yeah, so there's, uh, there's two for, for SD. I mean, for SDRs, it's. I do, I have them do cold email. Um, and, um, and then I'll have them like rework the email. Um, the challenge with that is that with like all the chat GPT stuff that now it's easy for them to just like ask it to like fix it. But I'm actually usually pretty good at, um, identifying that because what I really try to get them to do, I talk a lot about shared values and cold email, which is like something about you that likens to the buyer, um, and how it makes you similar. And actually that's really hard for AI to replicate.

Speaker A: Yes.

Speaker B: Um, and so that's something that I'll like be like, hey, what is something about you that you can like talk about with the buyer? And like, that's an easy filter for that. The other thing I have them do is like a sales, um, I have them do a presentation on uh, leads that they found, um, and like, who they would research and then like, um, a cold pitch, like a five minute pitch. I get feedback and have them redo those as well. For AES, it's more of, uh, discovery calls. Um, I think that's just like the normal thing to do. But to go back to your question from earlier, which is like, well, how do I, how do I like sniff out, you know, if they're going to be authentic with me? I actually make it part of their, like their 30, 60, 90 presentation. I explicitly call out, tell me something that is a professional development, like, weakness of yours, how you identified it and like, what you're doing about it. Um, and that's very telling as well because sometimes people will say like, oh, you know, I work on the weekends and like, I need to learn how to guard my time better. And, and I've worked with like a leadership coach to like, whatever. And it's like, all right, you're out. You know, like, you can't even tell me the truth about.

Speaker A: Yeah, I work too hard. Like, yeah, if you, if you, if

Speaker B: John, you said, Jeff, tell me 10 things that you're not good at. I could list you 10 things right now that I'm not good at.

Speaker A: I could list a lot more than that.

Speaker B: Yeah, I'm happy. Like, I, there's, there's. I have no problem doing it. Right. Like, so I want, I want to know. And like, so sometimes people will say, like, you know, something I've identified is that I am not doing a good job of getting to implicating pain and discovery. I found this out because in my last company I was losing a lot of deals at the demo stage. And when I spoke with my manager, we realized that the stakes just weren't high enough and that I wasn't quantifying the pain. And so what I've done to solve that problem is I've built my own discovery scorecard. And so after every call, I ask myself if I've answered these questions about implication. That's a perfect answer because that's like a really specific thing. It's something that, you know, I don't want them to have that problem. Right. So I want them to admit a problem that I don't want them to have and they've been intelligent about, hey, this is how I'm going to go and solve the problem. That's like, that's like the model answer that I want. Um, but it first requires them to be honest, which is to say that there is a problem. Right. So that's the way that I try to do it.

Speaker A: So let's go to SDRs. Um, right now it's a, ah, you know, there's all sorts of talk about this AI stuff taking over SDRs and um, the need for them. And there is a, there's, I can, I think for, for leadership right now looking at SDR teams as, as it's kind of become a challenge because the predictable revenue model I think was, was at a time when money was free grow at all costs. So it made sense and these kids were actually stay roles to become the ae. So it kind of made sense that you might not have made a ton of money on the SDR specifically itself, but as the feeder system it did. But now, you know, SDR stay in their company for a year and a half and half of them don't even go into AES. So you know, there's a real focal point right now with, with AI specifically saying it's going to take over the SDR role. First of all, give me your thoughts on that. Um, and, and the kind of the state of outbound as you see it right now. And then let's talk about what you are doing with your team to make sure that they're kind of keeping that authenticity and also balancing the scale. Right. Of the quality versus quantity debate that we all have to have as far as our investors coming and knocking on our doors and pushing us to get to the next level.

Speaker B: Sure. I don't believe it's going to happen. And there's a very practical and logical reason why it won't happen. And I'll, I'll explain that the, the buyer has a finite amount of time to give to taking vendor and sales calls. Uh, that is never going to change. Well, I mean, unless someone invents a way to like increase the amount of hours in a day or something like that, like, as far as I can tell, that's never going to change. Okay. And so what, what's happening is that if you think there's this concept of personalization, let's call it 10 years ago, where you say, hey John, I noticed that you went to um, University of Maryland and this was Like a novel concept back then. Okay? Now what AI has done is, is that it's made what I would call personalization easier to do at scale. It used to be that if you were going to do personalization, you would have to research people. And the reason people responded was because it was not easy to do.

Speaker A: Put in the work.

Speaker B: Yeah, because you had to put in the work. But now that you don't have to put in the work, all that has happened is that what the bar has risen on what spam looks like. Okay? Because if everybody starts doing the same thing, which is, hey, John, I noticed that you're a terrapin. Hey, John, I noticed you went to University of Maryland, you know, whatever. And by the way, I know that a lot of them are smarter than this and whatever. But all that happens is that you have risen the bar. Like, I don't have time. Just because 50 vendors are doing this now doesn't mean I can meet with 50 vendors. And so if it all starts to look the same to me or look similar to me, um, there's a finite amount of time. And therefore, by virtue of that alone, it just means that it can't change. Right? And so what that means. And I've really been harping on this for a very long time, um, because I really believe it. The one thing that AI cannot do, that does still require hard work is linking shared values between you and the buyer. And the reason AI will never do it is because AI doesn't have a soul. AI doesn't have experiences. AI didn't go to the University of Maryland as well, okay? And so I'm not saying that these need to be cheap things where it's like, hey, you're a Princeton alum, I'm a Princeton alum. Like, there's only so many of those. But it could be like, you know, I volunteered for Big Brother, Big Sister. Sometimes I find people who did the same, and sometimes that is a meaningful connection for someone to meet with another mentor. Um, but it could also be like, you know, I've had people, I've had AI outreach, say, hey, Jeff, I read your book Authentic Selling, and I say, what's your favorite chapter? And it gives me, like, gobbledygook crap, right? Whereas, like, if I were, you know, you just wrote a children's book that you showed me before the meeting. And if I said, you know, hey, John, I saw your children's book, I really loved this page. And it's because I've got a daughter, Josie. She's two and a half and she's negotiating with me about like, you know, whether or not she can watch more TV or whatever. Like, you would absolutely resonate with that message, right? Because you get that. And you'd be like, this guy clearly took the time out of his day. He found my book, he read it, he understands what it's like having a young daughter like that. AI first of all, it's not even close to being able to do that. So that will always land. It lands really well. Now there's one exception to this. I really do believe there is this concept of relevance which is like, well, there's all these signals out there where it's like, hey, this person literally just made this comment on LinkedIn and then they raised money. And you know, raising money is actually a stupid one. But, um, you know, they, they um, they're hiring this role and all these different signals can be leveraged to say, hey, I did a ton of like, whatever I did, whether I actually did research or not, I'm seeing all these things about your company. That signal that this might be of interest to you and um, maybe we should connect. I still believe there's a space for that. And I do believe that actually the like the signal based and then the intent based selling is actually elevating the sales game if it's used properly. Because the problem is that there's a lot of people who are still going to do the spray and pray. Yes. But if actually more people were to go down that world and not sell to the people who are not showing the signals, it would be a lot more fit. We would actually, it would actually elevate the way that outbound is perceived.

Speaker A: I agree.

Speaker B: Um, because we bought a AI orchestration product, we got rid of Gong and we like built everything in house. I had someone reached out to me at the right time with the right signal, they could tell that I was doing this research somehow. And we spent a lot of money on it and I was receptive to it. M. And that's why that work had nothing to do with, you know, Jeff, I saw you wrote a book or you went to the school. There was no cheap, like stuff there. It was just like they found Jeff at the right time at the right place. So I do believe that there is a. There is room for that, um, if executed well.

Speaker A: Well, I think what I've been preaching is the combination of right, because you hear trigger events, okay, great. But then you hear signals and then you hear relevance and you hear personalization and the best orgs that I've Come across. They get super tight on their icp. They track the shit out of them with everything they're doing with ABM and all that other stuff. They elevate signals to prioritize who the rep should then research for the trigger event to make the connection to.

Speaker B: To.

Speaker A: Because the signal itself a lot of times isn't something you could even reference, you know what I mean, without freaking somebody out. Hey, Jeff, I saw you were searching for this. I saw you were on, um, my. You know what I mean? That kind of is a little bit of like, dude, like, wait a minute, you're stalking the. Out of me. But if I can see you did this and went here and went that. And I'm like, hm, obviously something's going on in that business now let me go look on their website. Well, use AI to scrape and look for whatever trigger events or their recent earnings report or something like that. Then to come after you with the relevant and personalized. Yeah, because I think that's the key here is like personalization without, um. I actually think the fine line of personalization is personal. Like real personalization, legit, genuine personalization elevates you over almost. I call it the give a shit factor. It's the one thing I say that AI can't do. I can't give a shit. Like, it just can't. Right. So your. Your connected values thing, same thing. Right. Um, but the, you know, but being able to. To then personalize and make it relevant, because if it's not relevant, I don't give a shit. It could be the most personalized email you ever sent about my book and all. And I'll send you an email back maybe saying, thank you for referencing that. But if what you're selling me or what your value proposition is isn't relevant to what I need right now, it doesn't matter. So that's why timeliness matters. With that personalization, with that relevance. And the combination of those two is tricky. And that's why, for instance, one of the things I used to tell my team was, I want your list of top 25. Give me a tier one top 25 list. But before you can actually go prospect into that list, um, I need you to come back to me and tell me why you personally want to work with that company. So going back to your shared values thing, it's like, tell me why you as, uh, like as a person want to work with that company. Is it because they got great values? Is it their leadership's awesome? Is it because their product is badass? Or whatever. Because once you make that connection of like, wow, I personally actually want this as a. Want them as a customer, not just because they fit. Well, now your messaging comes through way more authentic. Way more like, now you're right. Whatever your email is written, whatever your voicemails are, because you had genuine interest in working with that client. And it's so hard to. But how do you balance that? I mean, I didn't look and I apologize. You got fun. Like, you're funded, right? Like you're. Is it.

Speaker B: Yeah.

Speaker A: So how do you balance that with the push?

Speaker B: Well, I can give you a real example. Is actually one that happened last week. It's like one of the biggest deals in our pipeline. The rep. She did this on her own. I didn't. I didn't. This is, like, not my idea. I didn't tell her to go do it. But this is how it's being adopted within our organization. And the way I'm encouraging them to think so we sell through brokers, we don't go directly to employers, and we very purposefully don't. Won't approach them because we don't want to piss off the broker community. Like, we're going through brokers now. Um, this is tough from a targeting perspective because all the data that's useful on, like, who we should target is on the employer level. If they're getting a bad renewal from their existing carrier, like, that's actually publicly available. And I can find that, and I can. But I don't target them directly. Now, what she did, which I thought was brilliant, and actually she picked up two huge leads from this. She looked up all in, like, her state, which I think is Texas. She looked up like any government organization with, like, a budget deficit. And then she looked up the decision makers and what brokers were engaging with their content on LinkedIn.

Speaker A: No shit.

Speaker B: And then she. And then she ran campaigns to them that said, like, hey, shot in the dark. But I saw you might be like, maybe you work with this company, maybe you don't. But they're having this huge financial crisis. Um, like, we would save them, like, $5 million. Do you think you might be a hero if, like, we got connected? I was on the call with one of these brokers yesterday with her.

Speaker A: This.

Speaker B: It, uh, like, literally is like a $5 million savings for this. Like, they were thrilled that we contacted them. Right. That's like a needle in a haystack where we got to the right person with the right message at the right time. But it's because someone on my team is being smart about how they're doing the research. Right. And she's saying, like, well, we know that people are going to be motivated if they're facing this problem. We know that they might be working with a broker if they're engaging on this platform. Now, of course, it doesn't work all the time. Sometimes a broker might be commenting on their LinkedIn page because they want to try to get. Get the business right. But it, you know, this is, I mean, these deals that she's brought into our pipeline are actually pretty significant opportunities. Uh, close them, I don't know. But that is the, um, that is kind of like the way that we want to be, um, trying to execute.

Speaker A: So do you have, like, metrics from a measurement standpoint, from an SDR team? Because you hear, you know, 50 dials, 100 activities, whatever the fuck it is, like, where do you fall on the activity level? So you track what they're doing versus the quality of what's going out?

Speaker B: Yeah, the SDRs, I would say, mostly pick up the phones, um, more than anything. So I think something that gets lost in this whole email thing is that picking up the phone is still like a tried and true method to, uh, that works really well, especially when you're getting hit with a bunch of crap all day over email. Like, sometimes someone who just like, picks up the phone and sounds genuine can be a really good thing. The metrics that, um. So a lot of the stuff we're doing with AI are more around call coaching. Like automated call coaching, deal score. We're automating, like, deal scoring by like, looking at all deal context from calls and emails and things like that. Um, what I can say is that our close rate year, uh, over year, has doubled since last year. Um, I don't know. The problem is I don't know where to attribute that. I don't know if that's like, my industry is getting warmer. I don't know if my reps are getting better. I don't know if it's like the tools I've built are making them stronger. My guess is it's a little bit of everything. But that's what makes a lot of this tricky is like, it's hard to attribute, uh, like a single source to any, you know, improvement. Um, so that's maybe, maybe one of the challenges that I have right now.

Speaker A: But do you do the. But is there the metric on them, like 50 dials or something like that, or. Because. Because I've always wondered, like, there's two levers you can Pull. Right. Like the quality and the quantity levers. As far as coaching is concerned, one of them, the easier one, is the quantity, which is like, I got to see that you can put in the effort, but then once I know you can put in the effort, I'm going to peel back and look at the quality is so kind of what's your. What's your approach as a, you know, from a leadership standpoint on. On that quality, quantity, balance?

Speaker B: Yeah, I mean, I would say, I'll be honest, nothing out of the ordinary. I think we look at, like, the number of connects and the number of, um, you know, booked meetings and things like that, um, to try to understand if somebody's being efficient and if they need coaching on the pH. Same thing with email campaigns, like open rates, reply rates. We look at sentiment and then we look at booked, you know, booked rates and so on. Um, I've done a little bit of, like, fractional work on the side. And, you know, one of the companies that I've been kind of helping out, I, you know, just yesterday we noticed that we had, like, a 1% reply rate on a, um, campaign for a conference, which is, like, really out of the ordinary. Like, we usually do really, like, really well. There's, um. And so, you know, that. That just triggered a very quick pivot, which is like. Just pick up the phones.

Speaker A: Yeah.

Speaker B: You know, like, something's not working here. Um, maybe this Persona in this geography is just not, you know, as friendly. I don't know. I mean, it's Kansas, so I actually would have expected otherwise. Um, but, um. But yeah, so I'd say it's. It's all of those typical metrics.

Speaker A: All right. You talked about the next book that you want to write, which is why? Based on a question that you love to ask, which is, why haven't you done this yet?

Speaker B: Yeah.

Speaker A: What's. Why do you love that question so much when you're. When in a discovery call? Uh, because now, you know, after SDRs, we get the conversation and now, you know, especially with AI and how fast things are moving and the builder buy conversation a lot of people are having, why is that the question that you think you, you know, has enough to even unpack an entire book around?

Speaker B: Yeah. Well, two things. I mean, first and foremost, as someone who wrote a book about, like, authenticity and AI and is now seeing that, you know, this is all anyone wants to talk about right now, maybe it'll be a little refreshing to people to go back to the reality that there's a lot of, uh, about Sales that is more about the art than the science. And that at the end of the day, that you're dealing with people who are emotionally driven, um, when they make decisions. And so that's number one. But number two is that I personally believe that there is a spectrum that people fall on in their willingness to buy a product. Um, and that when you ask the question, why haven't you done that yet? It unlocks for you where they fit on the spectrum. Um, and so I'll give you an example. Um, one part of the spectrum might be that they actually have the pain, but they don't have the awareness that, uh, a solution exists and therefore no awareness of a problem. Um, so an example of that would be like, John, if I told you that you could teleport right now, like we invented teleportation technology, and that if you wanted, you could just teleport anywhere you wanted, guess what just became your number one problem? So you don't have that. I mean, let's face it. I mean, if I could now solve that for you. But you're not thinking about that problem every day because you don't even think that a solution exists, right? So that's one place where you might fall on the spectrum. Another part. Um, and I think I can say this based on some words that were said at the beginning of the podcast, but there's a part of the book where I talk about urgency versus top urgency. And, um, you know, imagine if you are walking through Times Square and suddenly you have to take a. And, um, and it's going to happen in the next 30 seconds unless you find a bathroom. Okay? You may feel that taking a shit is the thing that you absolutely need to do right then. But what if I also told you that you were playing hooky from work that day and your boss told you, I need you to get on a zoom meeting right now with the CEO of our Biggest Cost or Prospect.

Speaker A: Right?

Speaker B: Dial in on your phone or whatever, or you're fired.

Speaker A: Yeah.

Speaker B: Well, guess what? You may feel that taking a is the thing that you have to do, but you're probably going to your pants and take that call. Um, because it became. Because there's a difference between having urgency to solve a problem doesn't mean that it's the thing that you're going to solve. You're going to drop everything you're doing and do right this second. And so there's a nuance to, like, in sales, we, like, oh, well, did they have urgency? Did they have pain? Did we implicate Pain, it goes deeper than that. You can have pain, you can implicate the pain. The pain can be massive and there can be massive urgency. And it might still not be the thing that they're going to do right now. Right. Like, it might be that they're, you know, it may feel like they need to take a. But there might be something that's actually more pressing than doing that in that moment. Right. And so when you ask the question, why haven't you done that yet? You actually unlock where someone is within this. And then by the way, there's a lot of parts of the spectrum that we didn't touch on, but you unlock, where are they in the spectrum? And I do believe that it's sequential, that you start from like a base level which is that they have no pain, no awareness, no urgency, um, whatsoever, and that you can move them um, further along. And um, the best part, and you know it's what you really want, is that they have all these things and that it's really just a matter of competition, you know, and it's a matter of determining who. Like that's what you want, you want to be competing. Um, but that's, that's why I think that question is important. It's a little bit of med pick and it's a little bit of some established subjects, but I think it's taking them a step further to layer them in a sequence.

Speaker A: Last piece on this. What are your thoughts? Because I just wrote this recently, um, on kind of disqualify. Because the reason I'm bringing this up is because I think it threads through your authenticity approach, which is disqualifying versus qualifying in the sense that so many reps are hyper focused on qualifying. An opportunity, with Bant, with medic, whatever it is, it's qualified. But because of that, I think they lose sight on the fact that this might not be a good customer in the first place and you don't want to sell it to everybody. So what's your philosophy on throughout the sales process doing things like, uh, like that. That question's a little bit of a disqualifier, right? In the sense like, well, why haven't you done this? Like, why are you talking to me at this point? Like, right, why haven't you dealt with it? So where's your head on disqualification?

Speaker B: I'm a big fan of disqualification. I tell everybody no is better than maybe. Uh, in my objection handling sequence that I teach people about, I talk about trying, trying to get to a no, I want to try to get Or I want to get to the objection. If I don't hear the objection, I can't overcome it. It. And um, so I'm trying to teach the sales team to hear bad things that they don't want to hear and that. And actually treating that as a good thing and that if they're hearing too much good things, that it's actually bad because they're not hearing. They need to hear the bad in order to get to the good. Um, so I'm a big fan of that. Um, I try to get them out in front of it. Um, uh, we have this deal scoring thing that we build using AI. That's a great way for us to qualify because I can look at a deal score and the rep can say, oh, I like, I think this deal looks good. And I can say, well, it's a 3 out of 25. So clearly there's some disconnect between what you think and reality. Right. Um, so I'm a big fan of like getting. Getting deals out of the way. And uh, you're right. We talk about it only through the positive lens, but we do need to think about it through the negative or the disqualification lens as well.

Speaker A: I mean, that's what we.

Speaker B: So the.

Speaker A: My favorite when I took this training that I deliver now from Basho, uh, Jeff Hoffman, you know, he's got this give, get scorecard. And it's like all, you know, negotiations about give and gets and the equality of those gives and gets. Right. And so we do all the gives and then point score them or like easy to give away, hard to give away. And uh, the gets early and late match it up. Because the problem is most qualification medic, all that stuff is just about the gets what we're trying to get from the client, but it doesn't marry up what we're giving away to get that stuff.

Speaker B: Sure.

Speaker A: Uh, and a client will tell you everything you want to hear. And that's where the happy years comes in. And a rep will lose a deal or get ghosted. Not have any idea why. It's like, well, you weren't paying any attention to what they were or were not asking from you.

Speaker B: Right.

Speaker A: And if they're not asking for shit, if they're not giving objections, this ain't a real deal.

Speaker B: 100%. Um, yeah. And it's great. I mean like, I have one rep who the. There's like a call where this person spent, I'm not kidding 10 minutes talking about why she hated the concept of what we sold. But I was really proud of Him. Because he tried to egg her on to keep going.

Speaker A: Yeah, he did.

Speaker B: He wasn't like, oh, I need to stop the bleeding. I want to, like, stop her rant here. He was like, tell me more. Tell me more about what you don't like. And then he overcame them one by one, and it was amazing to watch. And so it's, uh. Yeah, we're 100% aligned there.

Speaker A: Love it. Awesome. Well, when's it. When are you going to be writing that book? Because I know books are labor.

Speaker B: Like, why haven't you done that yet, Chris? Um, it's not my top pain right now. Um, I'm hoping to write it before the end of the year. Year. And so maybe it'll come out sometime next year if things go to plan.

Speaker A: Love it. Awesome, Jeff. Well, I think, uh, we can get back on talking about that in more detail next time, uh, when you release that one. So, uh, where can people find out more about you, what you're working on these days, Company, uh, hiring, all that fun stuff?

Speaker B: Yeah, I've got a website, jeffkirchik.com I maintain my blog there. It's a nice mixture of sales and personal tidings, I guess. And my book. Book links are on there as well, so. Yeah, you can find me on there.

Speaker A: Love it. Yeah. And like I said, send me over the, uh, address. And, uh, Is it Josie, right? Is that what you're saying?

Speaker B: Josie? Yeah, she'll be a big fan of the book.

Speaker A: And then, uh, I know you got another one. A little bit young to read to, but some, uh, of their names I'll have my daughter autograph, and I'll send you over one.

Speaker B: You're amazing. Thanks, John. I appreciate that. Yeah. Josie and Juliet.

Speaker A: All right, perfect. Josie and Juliet. Perfect. All right, well, look, thanks again for coming on M. Man, this has been fun.

Speaker B: Yeah, likewise. It was a good conversation.

Speaker A: Absolutely. And everybody hopefully 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 today, 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@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.