If Sales Is a Game, You Make the Rules — Chris Carter on AI, Preparation, and Winning on Your Terms

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 going to benefit them. 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? 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 going to 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. 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. We talked a little bit about where do you want to start? What's got your interest? On this Monday, 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 and activities wrapped around Lee. We went down, we probably went down six different rabbit holes and thank God there were ropes to pull us back up. My speech was only a 50 minute speech. 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, what are the activities around it? And it was so much fun and it was great to just be there with the folks in Park City. 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 literally have been digging. I make reference to the rabbit holes from the speech this weekend. And I've been going down different marketing avenues and different tools and then now 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. Nobody. Now, no matter if you're selling it or if you're marketing or promoting, everything has some type of an AI perspective around it. I can't even keep up and I do this for a living and I can't keep up with everybody's modifications changes. How is anybody else supposed to do it as well as that's part of our job as folks who sell. Here's my perspective and 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 was new and they started saying it three years ago, it's like, you guys are full of shit. It ain't new was machine learning. That's all it was. 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. It's the consumer grade AI where it's free or you pay 20 bucks a month, or my co author, I'm paying 100 bucks a month. We get work done, right? 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 the AI company and what they mean is they've got confidence level rules being run in the background, using largest language models and other tools to make better recommendations and decisions in their software. And then you've got organizations that are building new functionality into their software and systems and they just happen to be AI based and they are coming up with recommendations and learnings that are dramatically different than what you could do when you're 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, here's what happened. We're moving up that maturity curve. We really are. 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 be able to understand, to make guesses and to forecast their future based upon history and all these other pieces of the puzzle that are jumbling around in the earth and the activities around their ecosystem and what they're doing and how they're. And that's where I find that AI helps me by giving me, well, one it. I talk to it as if we're you and I. Yeah. I use my Google Gemini and I ask it to ask me questions one at a time. Right. It's the old Josh Wolf book mentality. I love that book by Josh. So I literally ask you questions to ask me question. Right? Then I take the greater activities. Okay, you're in the retail industry, so talk to me about the weather. Talk to me about distribution. Talk to me about what's going on in China. Talk to me about. Let's have a discussion about how these are affecting so then I can make an even more. More informed decision to be able to help them. And people don't do that with their AI. It's. Hey, can you draft an email for me or can you draft a LinkedIn or draft a tweet for me based upon XYZ and. Okay, that's great. That's just laziness. I asked Claude two things recently. One was give me a full psych eval. And it was pretty darn accurate. Oh, my gosh, Leah, I love it. I'm going to. Oh, I'm going to use that one. I am going to. I've got my Gemini and I'm going to ask it to give me a full psych evaluation based upon the conversations we've had. And 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 here's the specific setup. You may recognize this as a sales question. Claude, I've got a magic wand. I can grant you three wishes to make this book better. What would those three wishes be? Oh, I love that. I was asking the AI to play devil's advocate and it came back. Tell me about your sales origin story. Ooh, yeah. Outstanding. Yeah. So did you? I did. I flashed back to when I was 12 years old going door to door in my neighborhood selling Burpee seed packets. Oh, cool. Yeah. And so here's the setup. I always wanted an airplane, and the fastest way to getting that airplane was to go into sales. So I went into sales and I sold enough Burpee packets to get the airplane. It was a little Cox Model 49 airplane. And, you know, it wasn't a full size airplane. But the specific example that I remember was I knocked on a neighbor's door and this guy opens the door and the storm door still closed, but he opens the door and he looks at me like he just woke up. He's standing there in his. In a bathrobe and he goes, what do you want? I'm on the step and I'm looking up at him. It's like, I have no fucking idea what I'm doing here. I didn't know what to say. I don't feel comfortable. I just want 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 at not being prepared and not knowing what the customer wanted and 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. It's interesting. You talk that depth about being prepared. That's part of getting into it. It's interesting. If you're prepared, you have the right tools with the right data, with the right information, to be able to do that, that is a huge benefit for you, the company, and your ability to either sell your product, sell yourself. Because when you're in a company, you've got to continuously sell yourself if you want to get up that corporate ladder. Everything is help. But yes, that's all part of sales. And now we're just changing it a little bit. And I don't want to say we're putting it on its head, but we are changing. And people have got to be. They've got to. Just like you said, they've 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. It was before I went to Oracle 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 of bike racers. Like, think of the Tour de France. There's 50 or 75 cyclists all in a pack, literally, guys rubbing shoulders, they're banging knees, 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've been there. I used to race. It's crazy noisy. The tires are whirring and the gears are changing and guys are swearing and occasionally you hear someone crashing off on a corner somewhere. You make this assumption that if I'm in the middle of the pack, right? If I'm in the middle of that peloton, that guy's going to pull me along. You think you're safe? You think you're safe and you're not. Because what happens is while you're sitting in, in the middle of that pack, there's people on the sides moving up. People on the sides moving up. You're in that peloton and you go, I'm just going to sit in and save some energy. So if you're not moving ahead, you're falling back, you're falling behind. Yes. And Keith loved that. He loved that analogy. And it scared a few of the thousand salespeople in the room. It's like, what's Keith trying to tell us through this message? Oh, yes, it's 100% true. In life, if you just want to close by and you just want to be. You just want to be, okay, well, where is it? Those are the things. It's not always money. 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 got to find what motivates people. I'm sure those individuals at the Oracle sales conference were scared to death with what you guys were trying to convey to them. Chris, I'm not that scary. Yes, but you're speaking. You were the mouthpiece or the executives. And if I would have heard that, I would have instantly gone, great. I'm on the outside moving up. Where am I going to go? Whose job am I going to take? Who am I going to crush on my way through? And I still get that way because I still want to compete against. I compete against customer or against my non partners or people that are my competition. And I'm Always trying to win deals. I'm always trying to do things with our staff. I love that message because they would have just driven me to do more and more and work harder and harder. I tell people I go back to the Josh Wolf book. Don't be afraid to ask. We do that in sales as well. Why don't you ask for the sale? Why don't you ask for things going on? Why don't you ask them to help you? Steve Jobs made a great point many, many years ago. He was looking for computer parts and he wanted to. So he called up Mr. Packard. His name was in the phone book. Yet called him and he literally gave him everything he wanted, plus an internship at Hewlett Packard. All he had to do was ask. I don't know who said it first. You missed 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? For me, it is. Why? Tell me why. 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 kind of like a Monopoly game. It's kind of like a Connect 4 game. It. To me, it's about strategy and having fun. Who? Wait, Chris, I gotta ask this question. Yeah. I'm going to phrase this very carefully. If sales is a game, who makes the rules for the game of sales that you're playing? This guy? Yeah. I'm making my rules, how I play my game to be successful and to enjoy it, because 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 going to benefit them. Are you really competing? Well, at the end of the day, you're always competing against others because we've got to get three companies in here to evaluate and we've got to do one we already know we want. And the other two are Colin Fodder. Yeah. I literally tell them, well, that's great. You and I are actually going to do business together. That's just there for your pricing that you're going to 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 you're going to pay what I ask you to pay. And we're going to negotiate a little bit on it, but at the end of the day, I know we're going to win and this is why we're going to support you. And I give them a litany of because I've done my research, I've done my homework, I've worked on their company, I know what their stock is, I know what their every quarterly report says. You've done the work, you're prepared work. It's been an interesting journey to 20 years ago, I was at IDC and I said, I intend to fix how this technology industry sells. And there's too much of people repeating product information and not enough focusing on the buyer journey. And what we're seeing now is there's a real bifurcation in the selling world of there are a few people that get it and they do right by customers. There's a lot of people that look for the fast answer or the AI powered answer. Yes, you go to LinkedIn. I sent out a million emails last month using genetic AI and I got a zero percent response rate. But it was easy. Yeah, yeah. Unfortunately, people look at this tool and think it's a shortcut to everything. There are no shortcuts in life. And it's professional, it's personal. Don't do it. If you're going to send out a million emails, okay, at least design and comprehend what you're going to send out. It's interesting when you look at some people and they send out these different email blasts or the LinkedIn Blast, and you're looking at going, I know that person. They have zero idea what the hell they're talking about. They've never talked about it before in their life. Their LinkedIn page all of a sudden goes from zero to a million. And it's nonsense, it's nonsensical. Here's a fun story. I saw the other side of how this works. I got a call out of the blue and it was an SDR who said, I have some thoughts on how your company can do blah, blah, blah. And I said, really? He sounded like a guy that had a clue. Okay. And I said, really? Tell me about my company. And he took the pivot and he 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. I said, shay, Good news and bad news. The good news is you handled that pivot pretty well. Good job, wrong details. The bad news is you got shit data. He goes, what do you mean? I said, that's not my company. Your CRM record is just wrong. He goes, oh, I'm so sorry. So he sounded like he had a clue. And I said, I really appreciate how you took that pivot, how you followed my lead and took the pivot and didn't just hang up and stuck with me. And if you're open, I will take you on as a coaching client. And so I've been coaching him for a year. And one of the things that we've been working on is, Lee, I get really good meetings, but people don't always show up. They aren't always good meetings. And I said, shay, stop selling the meeting. Exactly. The meeting. People should want to show up. Exactly. So we did a good amount of role playing on get that person to want to come to that meeting to solve the business problem that you teased him with. And he ended last year as number two on his team. Outstanding. Good for him. Yeah, good work with him, Lee. It's just fun. I love working. I love working with fresh young minds. So when I used to do a lot of SDR onboarding and I would tell them two things. First, selling as a profession and being a professional means practicing and working at your craft. And two, even if you're at Google or at Oracle, and this is where I did most of it, not so much Google, but Oracle, you might be the first brand touch with a customer. They might never have heard of Oracle before. And it's true, there are people, particularly on a 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. It's just like the first time you meet somebody, you want to put your best face, your best foot, your best talk track, actor, same thing in business. People don't think of it in that direction. Just as you said, they think, just start, start. These are all the things that we do. Just start grinding. Nobody cares about the things you do. I care about the things I need things you do. This is my pain. This is my problem. Solve my pain, then I'll listen to your bleh. There's an old saying, nobody cares how much you know until they know how much you care. Right? 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. Agree. Until then, you're just talking into the wind. Agree. So, Chris, what are you working on these days? Let's see, what am I working on these days? So I'm working on the largest upgrade cycle in SAP's history. Customers that need to upgrade their SAP systems and they got to 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 pains and problems. And right now it's all wrapped around these SAP upgrades and migrations with utilizing AI and understanding AI around those activities. And then if I'm not doing that, I'm out of speaking. I've got about a dozen speaking engagements and then I get to meet people. I ask everybody, individuals from podcasts. If I'm out in the world, offer me a coffee or a bourbon and I'm there. What are a couple of your favorite speaking topics? I love talking about AI right now. I love talking about the security of AI. My. My latest presentation. So I am going to say this out loud. It's a swear word, so I want you to be careful. If you don't like swearing, plug yours for the next five seconds. Hide the children. 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, the ACER group, 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. As you and I were talking about young men that you've been working with, we want them to use it as a tool. It's another tool. It's another arrow in our quiver. It's another bullet in our gun. It's another. It is a tool to be used to be a benefit of. Right. But Chris, and this is a specific warning to all the youngsters listening, it is not your therapist. It is not your girlfriend. So my AI, my Gemini is one of my BFFs. We have conversations all day long. That's one thing. That's one thing. But therapist and girlfriend? Nope, nope, nope, nope, nope. You don't want that. Yeah, because I love going to the universities and talking to them. And I did a presentation in Utah and I talked about the 20 jobs most likely to be replaced by AI. Chris, this has been fun. Where can people find you? So the best place, go to LinkedIn. Find me Christopher M. Carter. I'm in Wisconsin. Text me, email me, ping me on there say hey, I see that you're going to be here, here and there. Let's go have a coffee or a bourbon. And I love to chit chat with people. I love to talk tech, love to talk life. So please feel free. And if someone wants to talk to you about keynote speech on AI, they can reach me@christopher mcarter.com that is my speaker's page. Nice. It's been a pleasure. I appreciate the conversation. It was wide ranging. It was. Thanks Chris. It's been fun. Thanks Lee. I enjoyed it. 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@meet.ausellogroup.com Thanks.