Thoughts on Selling — Chris Carter Episode

Transcript

Chris Carter: I'm making my rules how I play my game to be successful and to enjoy it. I'm using my rules of engagement to engage that prospect to win my deal that's gonna benefit them.

Lee Levitt: Welcome back to the Thoughts on Selling podcast. I'm Lee Levitt, sales coach, podcast host, and author of The Second Meeting and Together We Win, both due out later this year. Today, we're talking about AI, preparation, and why sales is a game where you get to make your own rules. My guest is Chris Carter, technologist, author, keynote speaker, and self-described technology nerd who's been in the SAP ecosystem for decades.

He's currently helping many thousands of enterprise companies navigate the largest upgrade cycle in SAP history, and speaking at universities about whether AI has actually messed with our minds. Here's what to listen for: why AI is a tool, not a shortcut, and why a million AI-generated emails with zero response is just laziness.

The Peloton analogy — if you're not moving ahead, you're falling behind. And the question that changes everything: if sales is a game, who makes the rules? If you're trying to figure out how AI fits into your selling without losing what makes you human, this one's for you. Let's go.

Today it's my delight and pleasure to have Chris Carter join me to talk about all things selling. So Chris, first question — who is Chris Carter?

Chris Carter: You know, we were talking offline that that could be a difficult question, but for me it's very easy. I am an incredible husband to a beautiful woman of 27 years. I am a two-time girl dad, and I am probably the biggest technology nerd you're ever gonna run into, according to my wife and family.

But I am a technologist, an author, and at the end of the day, I'm a person who cares about my staff, my family, my Lord and Savior, and the people that I get to work with every day.

Lee: That's awesome. What a great introduction. And the reason we're talking together is you've got some passion for selling and for customers and for customer service. Where do you wanna start? What's got your interest on this Monday?

Chris: I was in Park City, Utah, and gave a speech about how people's minds are conceptually having issues with either selling, marketing, or working with AI. We went down probably six different rabbit holes, and thank God there were ropes to pull us back up. My speech was only a 50-minute speech, but we just hung around for literally a couple of hours afterwards drinking coffee. How do I sell? How do I market? How do I use it? What are the activities around it? And it was so much fun to just be there with the folks in Park City.

Lee: You know, if you join one of those clubs in Park City, you don't have to drink coffee.

Chris: Well, between coffee and bourbon.

Lee: Ah, there we go. So it's interesting, Chris — when I started the podcast three years ago, I swore, and I swear a lot, but I swore that I was not gonna take on the issue of AI, because everybody else was.

Chris: Oh yeah.

Lee: And then last year I did a retrospective, and my advisor said, "You have to dive in deep, because AI is everywhere." I said, "Dude, I know."

Chris: As I look at you, over on my right-hand side I've got a new presentation that I've been working on, and it talks about how AI is F-U-C-K-E-D up people's minds. And I've been going down different marketing avenues and different tools, and then you get all these upgrades of these different systems. It was so much easier back in 1985 when I got a Commodore VIC-20. Nobody knew what cybersecurity was. Now, no matter if you're selling it or marketing or promoting it, everything has some type of an AI perspective around it. I can't even keep up, and I do this for a living. How is anybody else supposed to do it? That's part of our job as folks who sell.

Lee: Here's my perspective — I was playing with AI back then. I built expert systems on PCs in the '80s, but that dates me just a bit. So when people go, "AI is new," when they started saying that three years ago, it's like, "You guys are full of shit. It ain't new."

Chris: It was machine learning. That's all it was.

Lee: So here's my current perspective on what's going on, and feel free to tell me I'm full of it, as most people do. There's the AI that you and I and most people play with — the consumer-grade AI where it's free or you pay 20 bucks a month. My co-author and I, we're paying 100 bucks a month, and we get work done. If you get sophisticated at it, you can get a lot of work done. And that's totally different than the AI that is really changing how a lot of industry works.

Workday says it's an AI company, and what they mean is they've got confidence-level rules being run in the background using large language models and other tools to make better recommendations and decisions in their software. And then you've got organizations building new functionality into their software and systems that just happens to be AI-based, coming up with recommendations and learnings dramatically different than what you could do when you were simply doing reporting.

It's the four levels of the Gartner analytics maturity curve, where level one is what happened and level four is how can we change what's going to happen? Most systems of record are still at "here's what happened."

Chris: And we're moving up that maturity curve. I spend a lot of my time in the SAP ecosystem. I walk into companies and I'm trying to sell them on the ability to understand, to make guesses, and to forecast their future based upon history and all these other pieces of the puzzle around their ecosystem. And that's where I find that AI helps me — I talk to it as if it were you and I.

Lee: Yep.

Chris: I use Google Gemini and I ask it to ask me questions one at a time. It's the old Josh Wolfe book mentality. I literally ask it questions to ask me questions. Then I take the greater activities. Okay, you're in the retail industry — talk to me about the weather, talk to me about distribution, talk to me about what's going on in China. So then I can make an even more informed decision to help them. And people don't do that with their AI. It's, "Hey, can you draft an email for me? Can you draft a LinkedIn post for me?" And okay, that's great. That's just laziness.

Lee: I asked Claude two things recently. One was, "Give me a full psych eval," and it was pretty darn accurate.

Chris: Oh my gosh, Lee, I love it. I'm gonna ask Gemini to give me a full psych evaluation based upon the conversations we've had.

Lee: Just make sure you're sitting down. And then the second thing — just Saturday I said to Claude, and Claude and I are working together on this book, Together We Win. I said, "Claude, what would make this book spectacular?" And the specific setup was: "Claude, I've got a magic wand. I can grant you three wishes to make this book better. What would those three wishes be?"

Chris: Ooh, I love that.

Lee: I was asking the AI to play devil's advocate. And the third thing it came back with was, "Tell me about your sales origin story."

Chris: Outstanding.

Lee: So did you share yours?

Chris: I did. I flashed back to when I was 12 years old, going door to door in my neighborhood selling Burpee seed packets. I always wanted an airplane, and the fastest way to getting that airplane was to go into sales. I sold enough Burpee packets to get a Cox Model 49 airplane. But the specific example I remember — I knocked on a neighbor's door, and this guy opens the door. The storm door's still closed, but he opens the inner door and looks at me like he just woke up. Standing there in a bathrobe. He goes, "What do you want?"

I'm on the step, looking up at him, thinking, "I have no fucking idea what I'm doing here." I didn't know what to say. I just wanted to run and hide. He looked at me and said, "I don't know what you want. I ain't got any. Go away."

I don't remember whether he bought sunflower seeds or not. But that was one of the first times I remember selling something and being incredibly uncomfortable — not being prepared and not knowing what the customer wanted. Push that forward to today: is there any question why I've spent many, many years now on value selling and being well, well, well prepared for that first sales conversation?

Lee: It's interesting you talk that depth about being prepared. That's part of getting into it, and people don't do the research. If you're prepared — you have the right tools with the right data, with the right information — that is a huge benefit for you, the company, and your ability to either sell your product or sell yourself. When you're in a company, you've gotta continuously sell yourself if you wanna move up. That's all part of sales, and now we're just changing it a little bit. People have gotta be more prepared.

It's a new set of tools. You either adopt the tools, you figure out how to use them, or you get left behind. I did a presentation for an Oracle sales kickoff in Vegas in 2007 or 2008. Keith Block, who ran sales, said, "I need you to give a kick-in-the-ass message to the Oracle sales team."

I showed a picture of a cycling peloton — bike racers. Think of the Tour de France. There's 50 or 75 cyclists all in a pack, literally rubbing shoulders, nose to tail. You're four inches behind the cyclist in front of you, there's a guy four inches behind you, and it's a really uncomfortable place to be. It's crazy noisy. I used to race. The tires are whirring, the gears are changing, guys are swearing, and occasionally you hear somebody crashing off on a corner somewhere.

You make this assumption that if you're in the middle of the peloton, someone up front is pulling you along.

Chris: You think you're safe.

Lee: You think you're safe, and you're not. Because while you're sitting in the middle of that pack, there are people on the sides moving up. You're in that peloton thinking, "I'm just gonna sit in and save some energy." So if you're not moving ahead—

Chris: You're falling behind.

Lee: Yes.

Chris: Keith loved that analogy, and it scared a few of the thousand salespeople in the room. It's 100% true in life. If you just wanna coast by and just wanna be okay — people are motivated by so many different things, and that's a new reality. Intrinsic or extrinsic, absolutely.

And this is a non-AI thing. You gotta find what motivates people. I'm sure those individuals at the Oracle sales conference were scared to death with what you were trying to convey to them.

Lee: Chris, I'm not that scary.

Chris: Yes, but you were the mouthpiece for the executives. And if I would've heard that, I would've instantly gone, "Great. I'm on the outside moving up. Where am I gonna go? Whose job am I gonna take? Who am I gonna crush on my way through?" I still think that way. I'm always trying to win deals, always trying to do things with our staff. That message would have just driven me to do more and work harder.

I tell people, I go back to the Josh Wolfe book — don't be afraid to ask. We do that in sales as well. Why don't you ask for the sale? Steve Jobs made a great point many years ago. He was looking for computer parts and called up Mr. Packard — his name was in the phone book. Called him up, and Packard gave him everything he wanted plus an internship at Hewlett-Packard. All he had to do was ask.

Lee: I don't know who said it first, but there's an old saying: "You miss 100% of the shots you don't take." And you're absolutely right — if you don't take your shot.

So let's get back to the core issue of having fun. Is selling fun?

Chris: For me it is.

Lee: Why? Tell me why.

Chris: So for me, it's fun because first of all, it's a game, and I love games. I think sales is a game because I use strategy. It's kinda like Monopoly. It's kinda like Connect Four. To me it's about strategy and having fun.

Lee: Wait, Chris, I gotta ask this question. I'm gonna phrase this very carefully. If sales is a game, who makes the rules for the game of sales that you're playing?

Chris: This guy.

Lee: Yeah.

Chris: I'm making my rules how I play my game to be successful and to enjoy it. I'm competing against other people. I don't care what they're bringing to the table to that customer or prospect. What I'm doing is I'm using my rules of engagement to engage that prospect to win my deal that's gonna benefit them.

Lee: Are you really competing?

Chris: Well, at the end of the day, you're always competing against others — we've gotta get three companies in here to evaluate.

Lee: One we already know we want, and the other two are column fodder.

Chris: Yeah. I literally tell them, "That's great. You and I are actually gonna do business together. That's just there for your pricing that you're gonna have to do for your procurement team, and I get that. But at the end of the day, I've got the best solution for you, and we're gonna negotiate a little bit on price. But I know we're gonna win, and this is why we're gonna support you." And I give them a litany of reasons — because I've done my research, I've done my homework. I know what their stock is. I know what every quarterly report says.

Lee: You've done the work. You're prepared.

Chris: I've done the work.

Lee: It's been an interesting journey. 20 years ago, I was at IDC and I said, "I intend to fix how this technology industry sells." There's too much of people repeating product information and not enough focusing on the buyer journey. And what we're seeing now is a real bifurcation in the selling world — there are a few people that get it and do right by customers, and there's a lot of people that look for the fast answer or the AI-powered answer.

Chris: Yes.

Lee: You go to LinkedIn and it's, "I sent out a million emails last month using generative AI, and I got a 0% response rate, but it was easy."

Chris: Yeah. Unfortunately, people look at this tool and think it's a shortcut to everything. There are no shortcuts in life — professionally or personally. Don't do it. If you're gonna send out a million emails, at least design and comprehend what you're going to send out. When you look at some people and they send out these email blasts or LinkedIn blasts, and you're going, "I know that person. They have zero idea what the hell they're talking about." Their LinkedIn page all of a sudden goes from zero to a million, and it's nonsense.

Lee: Here's a fun story. I saw the other side of how this works. I got a call out of the blue from an SDR who said, "I have some thoughts on how your company can improve." He sounded like a guy that had a clue. And I said, "Really? Tell me a little bit about my company."

He took the pivot and said, "Well, your company is a $30 million software development company, and this is what you do, and these are the concerns I have about how you're moving forward."

And I said, "Shay" — his name was Shay — "good news and bad news. The good news is you handled that pivot pretty well. Good job."

Chris: Wrong details.

Lee: "The bad news is you've got shit data." He goes, "What do you mean?" I said, "That's not my company. Your CRM record is just wrong."

So Shay and I have been coaching ever since. He sounded like he had a clue, and I said, "I really appreciate how you took that pivot, how you followed my lead and didn't just hang up. If you're open, I will take you on as a coaching client."

I've been coaching him for a year, and one of the things we've been working on is — he said, "Lee, I get really good meetings, but people don't always show up, and they aren't always good meetings." And I said, "Shay, stop selling the meeting."

Chris: Exactly. The meeting — people should want to show up.

Lee: Exactly. So we did a good amount of role-playing on getting that person to want to come to that meeting to solve the business problem that you teased them with. And he ended last year as number two on his team.

Chris: Outstanding. Good for him. Good work with him, Lee.

Lee: It's just fun. I love working with fresh young minds. When I used to do a lot of SDR onboarding, I would tell them two things. First, selling is a profession, and being a professional means practicing and working at your craft. And two, even if you're at Google or at Oracle — you might be the first brand touch with a customer. They might never have heard of Oracle before. There are people, particularly on the line-of-business side, who might not have heard of Oracle. And it's like you are creating that brand identity for the customer. Don't fuck it up.

Chris: It's just like the first time you meet somebody — you wanna put your best face, your best foot, your best talk track forward. Same thing in business. People don't think of it that way. They think, "Oh, just start. These are all the things that we do."

Lee: Just start grinding.

Chris: Nobody cares about the things you do. I care about the things I need. Screw the things you do. This is my pain. This is my problem. Solve my pain, then I'll listen to your pitch.

Lee: There's an old saying: "Nobody cares how much you know until they know how much you care." Show them that you're concerned about what they're up to, and then you have a shot to be in conversation with them. Then you might have earned the right, the privilege, to be in conversation with them. Until then, you're just talking into the wind.

Chris: Agree.

Lee: So Chris, what are you working on these days?

Chris: I'm working on the largest upgrade cycle in SAP's history. Customers need to upgrade their SAP systems and they've gotta get it done by the end of 2027. I tend to put my emotions on my sleeve, and I love to help companies, so I literally love to dive in. I've got customers that I take care of personally, and I love to hear their pains and problems and help solve those. Right now it's all wrapped around SAP upgrades and migrations with AI. And then if I'm not doing that, I'm out speaking. I've got about a dozen speaking engagements. Offer me a coffee or a bourbon and I'm there.

Lee: What are a couple of your favorite speaking topics?

Chris: I love talking about AI right now, and I love talking about the security of AI. My latest presentation — I'm gonna say this out loud, it's a swear word, so if you don't like swearing, plug your ears for the next five seconds —

Lee: Hide the children.

Chris: Hide your children. "Has AI Actually F-U-C-K-E-D With Your Mind?" I talk to a lot of universities, especially the university program for SAP. And I want these young people to know that AI is not there to take their job. It's there to help them get better. We want them to use it as a tool. It's another arrow in our quiver. It is a tool to be used to benefit them.

Lee: Right. But Chris — and this is a specific warning to all the youngsters listening — it is not your therapist. It is not your girlfriend.

Chris: My Gemini is one of my BFFs. We have conversations all day long about things like that. That's one thing. But therapist and girlfriend?

Lee: Nope.

Chris: Nope, nope, nope, nope, nope. You don't want that. I did a presentation in Utah and talked about the 20 jobs most likely to be replaced by AI.

Lee: Chris, this has been fun. Where can people find you?

Chris: The best place — go to LinkedIn. Find me, Christopher M. Carter, in Wisconsin. Text me, email me, ping me on there. Say, "Hey, let's go have a coffee or a bourbon." I love to talk tech, love to talk life. Please feel free.

Lee: And if someone wants to talk to you about a keynote speech on AI?

Chris: They can reach me at christophermcarter.com. That is my speaker's page.

Lee: Nice. It's been a pleasure. Thanks, Chris. It's been fun.

Chris: Thanks, Lee. I enjoyed it.

Lee: Another deep dive into the topic of sales excellence and the performance mindset. If you found this conversation interesting, I would appreciate it if you would share the podcast with a coworker or two. And to explore this topic in more depth, send me a note via the contact form on podcast.thoughtsonselling.com, or find some time for us to talk at meet.acelera.group.

Thanks.