The "Hot Nerd" of Sales: Neuroscience, Improv, and the "Buyer First" Mindset with Carole Mahoney

The "Hot Nerd" of Sales: Neuroscience, Improv, and the "Buyer First" Mindset with Carole Mahoney

Lee: Welcome back to the Thoughts on Selling podcast. Today it is my pleasure to have Carole Mahoney joining as a special guest. Carole and I share some mutual friends. We share some mutual history. We both recently supported Stephanie Boyer at her National Intercollegiate Sales Competition.

We both have a love of selling, and let's start with the question that stumps other guests. Who is Carole Mahoney? Carole, I know you can handle this question.

Carole: I can handle this question. Carole Mahoney is a nerd — in terms of, I love reading neuroscience studies and psychology studies in my spare time. Also a nerd in the sense that I love theater, I love music. Even at my high school reunion, everyone told me I was a "hot nerd," and this was before the hot nerd was a thing back in the nineties. So I'm definitely a nerd first. I'm also a pretty big environmentalist. I was brought up in a family where we spent all of our time in the woods. We went camping, hiking, fishing, and hunting, and I was raised to believe that you leave no trace behind — you leave things in a better place than you found them. That has been my driving force — whether it's relationships or places or people, I love to see things grow and I love to leave things in a better state than I found them. So I am a nerd who likes to see constant growth and improvement. People are important to me. Experiences are important to me. If you want to find a really good gift for me, give me tickets to a concert or go hiking with me. I don't need more stuff.

Lee: Where's your favorite place to go hiking?

Carole: Oh gosh. Muir Woods, California, is probably my favorite place.

Lee: The trees are big there, huh?

Carole: They're huge. Last year in September, I was speaking at Inbound in San Francisco. The last time I had been in San Francisco for a conference, I went hiking in Muir Woods and I was so enthralled by it. I spent the entire day — I did 30,000 steps. I bought all of my family's Christmas presents in the gift shop. So when I went back this year, I said, I'm going again. I went by myself, did another 30,000 steps. I wasn't walking much the next day because I just sat there and listened to nothing. This sense of calm and wonder that you can't find in a lot of other places.

Sales Is Like Hiking — You Can't Be Prepared for Everything

Lee: So here's the cool thing about hiking, or mountain biking, or gravel riding, which I do. You can't be prepared for everything.

Carole: Nope.

Lee: And you—

Carole: Kind of like in sales too, isn't it?

Lee: Well, that was the bridge I was going to take.

Carole: Oh, I stole your bridge.

Lee: It's just like in sales. You can prep, but when the customer takes a pivot, you can either say, "Sorry, I can't help you," or you go with the pivot. You go where the customer needs to go. Carole, have you ever done improv?

Carole: Yes. Yes, and — when I did public speaking training, one of the parts... Now, I am a musician, and whenever I would play, I would always need my sheet music in front of me. It didn't matter how much I had memorized it — I needed the sheet music. It was like a security blanket. So when someone told me I needed to do improv and there was no security blanket, I thought, this is not going to go well. And what was funny is I had so much fun that I was laughing and crying. Now I love doing it. Sometimes I'll improv with my husband and he doesn't even realize that's what I'm doing.

Lee: A year ago, I took a deep dive into improv. I read Dan Pink's book To Sell Is Human, and he talks about improv as a great training platform for selling. I took that deep dive and I read a book he recommended called Improv — it was mostly about theatrical improv as opposed to comedic improv. So I joined a local troupe. Then over the holidays last year, my family was around and they said, "What's improv?" My wife had just enough experience of seeing and hearing what I was doing. We wrote a letter of complaint where each one of us said one word after the next. It was absolutely fabulous sharing that with the family, and they got a real sense of what improv is. I love it. It pushes me up against my limits and beyond.

Carole: We did something similar one year for Christmas. I host a big Christmas Eve dinner and we usually have games. One year, Drunk History was really popular. So we decided to do our own version of Drunk History and improv — some of the funniest things that came out of my family. We have a lot of fun with it sometimes.

Changing the Negative Perception of Sales

Lee: So you and I are on similar missions with regard to sales. They're different and related. What's your mission with regard to selling?

Carole: My mission is to change the negative perception that people have of salespeople — the pushy, manipulative, used car salesman stereotype. Like you mentioned, Dan Pink's book To Sell Is Human inspired me to write my book, and he wrote the endorsement for my book because I was so inspired by his.

It's because of this negative perception of sales that so many people don't go into sales, or if they do, they think that's how they have to behave, and they perpetuate that negative perception.

My mission was also to help small businesses grow because I grew up in a family of small business owners. When I first started my business, it was actually a lead generation agency. We did inbound marketing for people. What I found was that no matter how many good leads we developed for people, their sales teams couldn't actually close them.

You can't take marketing leads to the bank. You need to learn how to sell to today's internet-educated buyer, not the Glengarry Glen Ross techniques of old. In order to do that, I had to figure out how to sell myself — except I hated sales.

I got into marketing because I hated sales. I wanted to make salespeople obsolete. But what it really was is I wanted to make the pushy, manipulative con artist obsolete. It was because of my perception of sales that I was horrible at it and I avoided it and didn't want to do it, which was crippling in my business.

When I realized that in order to help small businesses grow, I needed to learn how to sell, what I didn't realize was that I would need to change how I thought about sales in order to be good at it. That was a real transformation for me. I hired a sales coach and worked with them for years. Not only did it change how I behaved in sales and how I thought about sales, it also changed how I showed up in everyday life.

I remember one day my kid said to me, "You know what, Mom? You yell a lot less than you used to." Which was a bit of a gut punch, but at the same time made me realize that to be a better salesperson, to change the perception of sales, we have to be better people. And it starts with listening. It starts with being curious. It starts by putting other people first — hence "Buyer First."

When I started going down this path and realized that my real mission is to change the perception of sales, it was because my ex-husband was not a good person. When I decided I was going to leave him, he said, "You will never amount to anything more than flipping burgers at McDonald's." And it almost came true — until I learned how to sell.

Changing the perception of sales from negative to positive is so that other people will embrace sales, and more women will get into sales so they can create security and financial independence for themselves and their families — so they never have to settle for a relationship they shouldn't be in.

Lee: That's so powerful. I can see that in your work with Stephanie Boyer at Bryant University in the collegiate sales competition. Just as a shout-out, I had one of the five finalists from the recent competition on — Nina Iannuzzi, a 19-year-old sophomore at UMass Amherst, Isenberg School. Her quote was that she'd been selling slime to her fellow students since she was five years old. This is the next generation. Some of the people who want to be salespeople are young and eager and motivated, and they don't know that old persona.

Carole: Yeah, and I think you're right. That is the real opportunity. Sometimes I feel like I'm beating my head against the wall trying to get established salespeople who've already learned the bad habits to unlearn them and shift their perspective — it's a big lift. Working with Harvard Business School MBA students, working with Stephanie at the NISC competition, and now teaching students at the Emlyon Business School in France on the Masters of Sales, I've realized the real opportunity is in teaching the next generation how to be good salespeople. And the next generation after that, and after that — we will change that negative perception of sales without having to convince everyone that we need to.

It's Not About You — It's About the Customer

Lee: You know, it's funny you described the experience you had with your own business. I've worked with a handful of principals of small professional services firms, and every one had that same chip on their shoulder, that same voice in their ear saying to sell, you have to have that plaid jacket, you have to be an asshole, you have to be an idiot. And I would say to them, you can let go of that image and be yourself. Share the passion for what you do, and that's okay.

Carole: Yeah, it's interesting. I have a lot of small business owners that I work with as well, and startup founders, as well as larger established teams. But with the small business owners and startup founders, if I had a dime for every time they said, "I need to get more customers, but I don't want to be salesy." I'd ask, "Well, what do you think salesy is?" And then I'd say, "Okay, good. That's exactly what we're not going to do. So you're good."

Lee: So that's an awesome mission. I mentioned that your mission and mine are in alignment and different. When I started the sales productivity practice at IDC in 2006, my stated mission was to fix how the technology industry sells. My perspective — and I'd been in technology sales for a long time at that point — was that it's all about the product. "Here's the latest widget. It's 3.2. Version 3.1 is old and obsolete. You need to buy 3.2." And nobody gives a shit.

Carole: Nobody. Does this solve my problem?

Lee: Right. Does this help me save money on cloud expenses? Does this improve my security? Does this allow me to serve my customers better? Years ago, my cousin ran a bike shop. He was computer savvy, and I said, "BJ, what technology do you use to manage your inventory?" He said, "I manage my inventory by walking around. I have a three-by-five card, and if I see that I'm low on something, I write it down and order it." He said, "I don't need anything more than that. I don't need a fancy $10,000 or $100,000 computer inventory system." We are so enthralled with technology in the technology world — and it makes sense, right? The high priests of technology get together, they build the latest whiz-bang product, and then they want to talk about it.

Carole: Yeah. It's their baby.

Lee: Exactly.

Carole: Don't call my baby ugly either.

Lee: Once you get past the early adopters — once you cross that chasm, thank you Geoffrey Moore — once you get to the early mainstream, they don't give a shit. It's like, "Will this help me drive that nail? No? Okay. Next."

Carole: My first corporate job was as a sales coordinator — I didn't want them to call me a salesperson — in a startup company. The majority of the clients that I work with are technology companies. And I kept having to say to them, "It is not about you. It is not about your product or your features or any of that. It has to be all about them."

That became the inspiration for the book. In fact, one of the companies that I did a lot of work with was HubSpot. They would say, "I keep making it about me." And I would say, "It's not about you." They're like, "I need to get that tattooed on my forehead." I said, "No, you need a t-shirt." So I created these t-shirts that say "Not About Me" — but it's printed upside down so the person wearing the shirt can look down and be reminded, because we need the constant reminder. Even in my own business, sometimes I fall into the trap and I have to remind myself, "You're doing it again." Because we're so excited about what we know and what we can do and how we can help, it just comes off as us pitching. And that's not good.

Lee: Yeah. I was very fortunate to join a group at Oracle that focused on the value selling mindset. For six years we instilled that focus on the customer — value selling mindset with curiosity, a point of view, business value hypotheses, the relationship as a bank account, understanding where we stand with people. It was a glorious time in an organization that invented the database, helping salespeople sell databases without talking about databases.

Carole: Because value is in the eye of the beholder, not in the person talking.

Lee: That's right. Now, of course, on the downside, we also talked about communication styles at Oracle, and I shouldn't say this, but we always said Oracle salespeople had two ways of communicating: talking and waiting to talk.

Carole: "Is it my turn yet?"

Lee: Yeah, "Is it my turn yet?" Apologies to my fellow former coworkers.

What Carole Is Working On Now

Lee: So you're on this mission. You've written a book. You donate your time and energy to good initiatives. What else are you doing?

Carole: Gosh, there's a lot. We're talking about technology — I'm developing some generative AI to put into a platform to really help people ramp up their learning, and to do that in a way that is focused on the buyer and not on the technology or on ourselves. I'm developing that technology so I can help more people because there's just me and I need to be able to expand.

And then I'm also working on my next book. The next book is going to be Seller First and is going to be written for managers. Buyer First was for the salesperson, for the small business owner on the front line — how do you actually engage with people in ways that they're going to value today? How do you adopt those behaviors?

Seller First is about: now that you're a small business owner or startup founder who wants to scale your sales, and you need to hire someone and figure out how to manage and coach them — how do you create the environment as that middle manager or startup founder that will allow your salespeople to be buyer first?

What a lot of people don't realize — and I've seen this happen in my own practice — is that salespeople will come to me for individual coaching and then go back into their companies and revert to their old behaviors. It's almost like trying to lose weight while being surrounded by pepperoni pizza and hot fudge brownie sundaes. You're eventually going to slip back into your old ways. So it's not enough just to change the salespeople. We also need to train and coach the managers on how to train and coach their people, and on hiring the right people to begin with.

Then the next book after that will be Manager First for leaders — how do you create the systems, processes, and culture that all of this can live within?

So I'm working on the next book, creating the generative AI platform, and next year I'll be starting to teach at the Emlyon Business School in their Master of Sales Excellence program, which I'm super excited for. So I'm learning French. I'm also working on renovating our home — adding an addition and a garage so I can get a bigger office and studio, and host some executive retreats here because I live in the Maine woods with a lake and trails. Really doing some deep-dive retreats with people.

Lee: Have you hired Maine Cabin Masters to do that addition?

Carole: They are on my list, actually. I want to hire Maine Cabin Masters because once I have the garage and the addition done, I want to put little cabins that people can go and stay in or maybe rent out. So yeah, there's a whole empire in my mind right now.

Learning to Slow Down

Lee: You've got a lot going on.

Carole: I always have a lot going on. I am not someone who sits still very well, which is something I'm working on.

Lee: What do you mean?

Carole: Literally — when we're watching a movie with the family, for me to sit through a whole movie and not get up to go get something or do something is a miracle. I am in constant movement.

Lee: I got that part. But you said you're working on it.

Carole: I'm working on it. I'm trying to get comfortable in stillness and quiet where I don't have to feel like I'm moving forward or doing something.

Lee: Good luck with that.

Carole: Yeah, exactly. I've started a morning routine where I get up and do yoga, meditation, journaling, and practice my French lessons before I dive into the day. I've started with that and now I'm taking weekends off — I'm not working through the weekends anymore. Like any behavior, we're stacking the habits. Started with the mornings, now we've extended into weekends. I actually took a vacation this year. So we're getting there.

Lee: I ask you the question as someone who also can't sit still. I describe it as — I'm like a shark in the water. If I stop swimming, I die.

Carole: Well, and if you go to my website, Unbound Growth, and you see the logo, the logo is actually a Triskelion Celtic symbol, modified. The reason I chose that is because it's a symbol of constant motion, constant improvement — always trying to get better and be progressive. Which also can burn you out. So there's a balance between that constant wanting to improve and being able to not burn out.

I have to give a shout-out to my friend Katie McDonald because she's been one of the key people close enough to me that she can tell me to slow the hell down. For her, she talks about how self-care is not a guilty pleasure — it's our duty. We have to be able to take care of ourselves in order to show up for other people. That's something I'm working on in small daily habits and taking those moments to just be present with my family, taking the holidays off, and not thinking about the next thing I need to do. It's a work in progress.

Lee: I have a good friend, Alan Cantor, who 25 years ago called me up one day. We were in constant communication. He called me up and said, "How you doing?" I said, "Alan, I'm running around like a chicken with my head cut off." He said, "Call me when you're not." And he hung up. I remember it like it happened this morning. His message was the same: chill out.

Carole: Yeah. When I left my ex-husband, I actually moved in with my grandmother because she needed help going through knee surgeries and recovering. I had two kids, I was a single mom, going to school full-time, working full-time, taking care of my grandmother, trying to build a house. And I remember my mother saying, "You're burning the candle at both ends and you're gonna burn out." I said, "No, no, no, Mom. I've taken that candle, broken it in half, and I'm holding both of those ends on fire." But I also said, "What would you have me stop doing? Stop going to school so I can make a better life for my kids? Stop working so I can pay my bills? Stop taking care of my grandmother through two knee surgeries?" There was nothing I could let go of at that point. Whether that's unfortunate or not, it has carried over into my adult life. But I am proud of myself for taking my mornings and my weekends back and not working until eight or nine at night anymore. I'm getting there. I still have a million projects though.

Lee: Yes, you do.

Carole: I'm always pushing the edge in some way because I get bored easily, I guess. I always find ways that something can be improved. My husband is a very good balance for me in saying, "Good enough can be good enough." It's not a letting go. It's not quitting — it's letting things be as they are.

Lee: I like to improve things too. My daughter in middle school explained to her teacher and the special ed teacher, "It's a circus in my head." They got it — she was working at 200 miles an hour and doing well and needed some support. When she said it that way, we all went, "Now we get it." She was the second of three diagnosed with ADHD in my family. First my son, then her. My wife looked around and said, "Where'd they get it from?" Me.

Carole: Yeah, both of my sons also have ADHD. I was never diagnosed with it, but I'm pretty sure I would meet the threshold. But the interesting thing is that all of the strategies I've had to learn to calm down and be present are also the strategies I now teach my clients. Because it shows up in sales, right? When you're constantly on the go and your mind is constantly worrying and you're listening to all of these thoughts in your head, you can't listen to the other person. You're not even in the same place with them. You're somewhere else — in the past or in the future — and they're right there.

When you're not in the present moment, that's what makes you slip up and miss the cues where you should be asking deeper questions, or the cues that something isn't really landing with them and you need to stop and pause. That's the magic in a sales conversation that most people don't see and skip over. But if you're listening to that call and watching the recording as an outside person, it's easy to spot.

Listening, Curiosity, and the Intent Behind Sales

Lee: Absolutely. I have a coaching client who did a personal interest event. He and a friend have a podcast on watches. They did an event where a major high-end watch vendor sponsored and they got 40 people into a room. The vendor talked about the product and shared some stuff, and one of the people at the event said, "I'm really interested in that watch." And the vendor salesperson said, "Oh, well, let me show you the other watches," and totally missed it.

Carole: Put the $5,000 watch on her wrist and just stop talking.

Lee: Stop talking. No sale. There was probably a pretty good likelihood that was going to be a sale. They went right past it. They didn't hear what the customer said.

Carole: I've seen it happen where they've actually talked the customer out of purchasing. Last year I bought a new car. I went to a couple of dealerships. I found the car I wanted online and went directly to the dealership. They had it ready for me and I was driving it around. But previously I had gone to another dealership and I thought I was going to buy that car. The salesperson said, "Well, I'm sure you want to go home and think about this." And I said, "No, I'm pretty sure this is what I want to do." They said, "No, no, no. I understand this is a big purchase and you want to go home and think about it." They literally talked me out of it to the point that I went to another dealership to find the car I wanted and bought it from them.

Lee: In my practice, we call that "how you buy is how you sell."

Carole: I was thinking exactly that. If someone needs to go over every piece of evidence everywhere else and compare it to everything and get the best price and get a discount — if you buy that way as a salesperson, you will sell that way as a salesperson. Unless you're aware that you shouldn't.

Lee: Unless you change your own way of making purchasing decisions, you'll always be susceptible to people who are going to do the same. I have coached many salespeople to uncouple how they buy from how they sell — the expectation of what their customers are going to want to do. Listen for what they say. Listen for how they want to buy. Ask them how they want to buy. Don't assume.

Carole: Oh God. Assumptions — you know what they say about assumptions. It goes back to not making it about you. You are projecting your beliefs onto someone else. You're projecting how much money you think is a lot of money because you're not used to that, whereas for them, that's nothing. I encounter that time and time again. It's like a bad form of empathy. The good news is that it's also the easiest one to fix. When you start changing how you make your own decisions, then it's a lot easier to help people make decisions they're comfortable and confident in.

Intent Is Everything — The Difference Between Sales and Manipulation

Lee: We've talked about so much good stuff, Carole. For me, curiosity and authenticity are two of the key attributes. I coach salespeople to be conscious of their context. And the context — or your intent — is written right on your forehead. Or upside down on your shirt, as we talked about earlier. If you walk in saying, "I need to sell something today" — no sale. If you walk in and your context is curiosity...

I had a coaching client who started a meeting with senior VPs at a mutual insurance company, and the first question she asked was, "I noticed that each of you has been with this company for more than 20 years. What keeps you here?" Twenty minutes later, they finished that conversation. And oh boy, did they love her. She said one thing and they talked for 20 minutes.

Carole: There's some science behind that, which I can nerd out on later. But the thing I find interesting is — I just commented on LinkedIn. Bek Khol was talking about how we use tactics to get what we want, to manipulate people into doing something. I can't tell you how many times I've had a coaching client or student say to me, "How do I get them to blah, blah, blah?" And I said, "First you have to stop thinking about how you're going to get them to do anything because that's manipulation."

You can take any tactic, good or bad, and depending on your intent, that's how it's going to come across. You can use the exact same tactic to help someone, or you can use the exact same tactic to try to manipulate someone. And the only difference between a good salesperson and a con man is intent. That's why I'm so emphatic — you have to make it not about you. You have to be willing to put what you want aside for the better of someone else. And until you're willing to do that, you shouldn't be in sales.

If you're not willing to say no to someone because it's not the right fit for them, no matter what they say — contrary to what we were saying before about projecting — if you know that it's not the right time, it's not the right fit, or they're not going to be successful with it, it is your ethical responsibility to tell them no. I wish we had an oath like doctors have — that we will never sell something to someone that they don't need.

Lee: I coach a handful of salespeople who work for a couple of very large companies, and for the past month we've been doing role plays on how to say no — and not to customers, but to sales management. "No, I'm not going to try to jam it down their throat before the end of the year." "No, they don't want the extra discount." "No, they're not going to say yes right now."

Because the individual salespeople know — they have the perspective of the customer. If they try to jam something into Q4, they will lose. They will hurt their relationship with a customer. The customer's going to go, "Okay, thank you for that extra 20% discount. I'll collect that in March when we're actually going to buy."

Carole: Exactly. It's interesting because I was just talking with one of my clients earlier today. We do an assessment with every client we work with. We use a sales-specific assessment that not only looks at their skills, but at what we call the "sales DNA" or the mindsets they have — things like the need for approval, managing our emotions in the moment, handling rejection, being comfortable talking about money, how we buy is how we sell.

The need for approval shows up when you're not willing to say no. So a lot of times what I have my clients and students do is: if you're not comfortable saying no, then you need to start practicing saying no to people in your everyday life. Start setting boundaries. When we have a need for approval, we want people to like us. We're more likely to say yes to things we wouldn't normally because we don't want to upset them, or we tell them what we think they want to hear. And what happens is they not only don't trust us — they don't believe anything we say because we're just telling them what they want to hear.

When I have said no to people that weren't good fits as a client... I talk about the story in my book when my business was at a super low point and I thought I had to go get that four-letter word we call a "job" in entrepreneurship. I was doing interviews and my sister introduced me to her boss for a marketing position. I had the interview. I was desperate to get some money in. He said, "I'm having a hard time making this decision between you and this other person."

Now I knew who the other person was. My first instinct was to try to convince him why he needed to hire me. Then I thought, this is my sister's boss. If this doesn't work out, not only is it going to damage my relationship with her, it's going to damage her relationship with the boss. So I asked the only question I could think of: "What is the most important aspect to be successful in this role?" When he told me I was going to have to dress up in a mascot suit and go to events around town, I said, "That is definitely not me. You should hire the other person because I know that is their thing."

His response was, "Thank you so much for making this decision easier for me. I'm going to go find who I can refer to you so that you can get some business in." And that's exactly what happened. Saying no builds instant trust. It gets clear on what's going to be the best situation for you. But so often salespeople won't do that — with their manager, with their buyers, or even in their everyday lives.

That's one of the things I love teaching. If you can practice this in your everyday life, it will be easier to do when you get into a sales conversation, which has more pressure. There's that whole thing about money and value. People would rather talk about religion, sex, or politics before they talk about money. Money is the biggest contributor to divorce as well, because people won't talk about money with their spouse.

Teaching the Next Generation of Sales Professionals

Lee: How do we get the younger generation of salespeople — for whom maturity and self-awareness hasn't come yet — to be able to say no, to be present, to have the best intent? What's the magic wand, Carole?

Carole: Wish there was a magic wand. I call it a cognitive behavioral approach to sales, and I don't think it matters whether you're young and inexperienced or older. I think the older you are, the harder it's going to be because these habits have been ingrained inside of you and it's harder to unlearn them.

This is what I love about teaching the next generation — I can teach them techniques they can use in their everyday lives that make it easier. The emotional stuff — I talk in my book about meditation over a dozen times because of the neuroscience and psychology behind it. Even just taking a minute to do a breathing exercise will lower your heart rate. It will lower the mechanisms happening in your head so you can actually make better decisions. Physical reminders to bring you back to the present moment — I used to always have an elastic on my wrist, so whenever I found myself checking out, I would snap myself literally back to the present.

The things you do in your everyday life — like we were talking about trying to slow down — that's what I teach the next generation. I understand they have all this energy and ambition and all these things they want to do. We're also seeing an epidemic in the younger generation burning out because of the pressure and frustrations they face. They need to learn how to do self-care routines and have healthy relationships and boundaries, because that's what's going to serve them in handling the complexity, uncertainty, and constant rejection of sales.

Lee: I love onboarding new salespeople. Monday morning they're sitting in a conference room wearing the red "class of" t-shirt or whatever. Three weeks ago they were at senior week. And I tell them two things. One: selling is a profession, and professionals practice their craft. They don't just show up on game day and wing it.

Carole: Exactly. They watch their game tape. They get coaches. They have multiple coaches usually.

Lee: And the other thing I tell them is — even if you're working at a very large company, you might be the first brand touch that your customer ever experiences. They may never have heard of Big Company Incorporated dot com. You're their first touch. Be a professional. Be polished. Be prepared. Be a human being. Be a listener.

Carole: Yeah. I actually have one of my clients right now — it's a startup that just hired a gentleman who came out of college, and he's literally a sponge. If I could have every client just do exactly what I tell them to do, my life would be so much easier. But for the most part, that's what I find in new college graduates — they're so grateful for it and so eager to apply it. "How do I constantly learn? How do I constantly improve?"

To your point about practice, I get this question a lot from my Harvard Business School students: "How can I get more practice reps in? We only have six weeks." And I say, "You know what the beauty of sales is? You can practice it on anyone around you at any time." I've had sales conversations with Uber drivers who then went on to become salespeople and still message me every once in a while about their sales success. Grocery store clerks. Waiters and waitresses. People you're standing in line with. We are all salespeople. We've been selling our entire lives — which means we shouldn't be afraid of it, and we shouldn't be afraid to just have conversations with everyday people where we're asking and being curious about them.

Like you said about asking that one question that gets them talking for 20 minutes — the science shows that when you get other people to talk about what they think, it lights up the dopamine in their brain, which comes from the area where we build trust and relationships. So many salespeople go into a conversation and do all the talking and think it was a great conversation because they were doing all the talking. They were hogging all the dopamine from their buyers. But when you get your buyers to share, that's when you start to build trust and relationships. You need to do more than that, of course, but that's the start.

Lee: The less you talk, the better it goes.

Carole: Generally speaking.

The Art of Great Service — A Lesson in Sales

Lee: I had a dinner last night with a coaching client at Atlantic Fish Company in Boston on Boylston. Shout-out to Kristen, our server. I asked Kristen, "What's your favorite fish dish here?" And she went through three or four — maybe five. She didn't answer the question directly. She was energetic and enthusiastic and passionate about multiple dishes. We thought about it for a bit, and then I said, "So, salmon or tuna?" And before I finished the sentence — "Tuna."

Carole: I grew up working in restaurants — front of house, back of house, I've worked every job in a restaurant. I loved waiting tables, which seems crazy to some people. I would actually just do it for fun for friends that had restaurants. It was like having a great big dinner party with new friends. I would have regulars who would come in and say, "So what am I eating today? You pick for me. You know what I like, you know what I don't like. I don't want to decide — can you decide for me?"

Lee: I love asking that question. Walking in and saying, "Here are the boundaries. I won't eat scallops, I won't eat blah, blah, blah. Aside from that, just surprise me." And some waiters won't take that on.

Carole: The good ones do. I was in France with Lauren Bailey and Anna Bard from our Legacy Group Club — shout-out to them — and some of the best dining experiences I've ever had. Because I didn't understand everything on the menu and Google Translate can only go so far, the best waiters and waitresses were the ones who asked questions about what I liked and then said, "Here's what I would recommend." I didn't have a single bad meal the entire time.

Lee: I would hire Kristen in a minute for any enterprise team. Passion, energy, enthusiasm, and product knowledge.

Carole: Part of my work with clients isn't just coaching salespeople — it's coaching and training leaders on how to hire salespeople. Where do you find your best recruits? A lot of times my go-to is, "Do you have a favorite waiter or waitress? Go hire them for sales. That's what they're doing."

Lee: I ran sales for By Appointment Only. Henry was the recruiter for the people who made 250 calls a day setting appointments. I would frequently onboard some of those folks — landscapers, hairstylists, real estate people. There was no rhyme or reason to the titles. And wouldn't you know it? Seven out of ten, eight out of ten were successful. Henry had a format, a template that he matched no matter where they came from. He was looking for a series of skills and attitudes that would make someone successful in that high-pressure environment.

Carole: And that is exactly what I teach when I'm training leaders on how to hire. First we go through a detailed list of criteria for someone to be successful in the role. When I say "successful in this role," it's not just what they're selling and how much — it's the level of competition they'll face, how they're going to be managed, who they're used to selling to, who they'll need to sell to, what kind of sale this is. Will they sell and move on, or sell and service? It's very specific.

Then when we hire, we use an assessment to match against aptitude, attitude, and skillset for that role — because hiring from your competition is not a guarantee of success. Their company is not your company. Their buyer might not be exactly your buyer, even if you think they're a competitor.

That's part of my passion — helping companies stop churning through salespeople and hire the right people for the role. It's why I often say, and this is the premise for the next book, that companies often create the problems they try to solve for later on. And they don't even realize it.

The Manager's Impact on Sales Teams

Lee: I worked with Dave Kurlan at Objective Management Group years ago.

Carole: Yep, that's the one I use.

Lee: He profiled my team at By Appointment Only. Then he profiled the managers, of which I was one. Oh my God.

Carole: So interesting thing about the data — because I'm a partner with them as well, they let me do some analysis of my own. A couple of years ago I did an analysis because we've all heard the phrase "as goes the manager, so goes the team." We can observe that, but how true is that really in sales?

I took 500,000 managers and the teams that reported directly to those managers. What I found is that when managers had certain non-supportive beliefs or mindsets about sales, their teams were 355% more likely to hold the same negative beliefs, which impacted their skills. However, managers who had supportive mindsets and beliefs were 1,000% more likely to pass them on to their teams, and those teams performed better. The bad news is that only 7% of the managers out of the 500,000 we evaluated had the positive mindsets.

It's a huge impact that managers have. As I was saying before, you train a salesperson, they go back into their company and they're surrounded by cake and pizza — they're going to regress. We have to make sure that the managers are the ones influencing their teams in positive ways and not creating more problems.

Lee: The confounding variable there, Carole, is that many managers — perhaps most managers — come from the sales team. They're the lone wolves that were successful in spite of everything. "Oh, you were 150% of quota for five years? You should be a manager."

Carole: And then the manager doesn't understand why everyone doesn't just do it the way they did it. It's the other side of the Dunning-Kruger Effect. You know Dunning-Kruger — the less experience you have, the more likely you are to be overconfident in your skills. But the other side that most people don't talk about is that when you are at that expert level, you can't understand why someone else doesn't get it. It's the unconsciously incompetent to the unconsciously competent, but there's a whole bunch of stuff in the middle you have to go through.

And the other thing is that being a top salesperson is a completely different mindset and skillset than being a top manager. At Objective Management Group, we talk about the need for approval. In salespeople, it causes them to not get to decision makers, to not ask tough questions — they think people need to like them. But in management, it prevents them from having tough conversations with their salespeople. Same mindset, different application, different context, different result.

Why Sales Coaching Matters — Quality Over Quantity

Lee: When I was running the Sales Advisory Practice at IDC, people would ask me about leading indicators for sales results. And I said, in literally any size company, any industry, the percentage of time spent coaching by sales managers is probably the single biggest leading indicator. And if you were to survey every single sales manager in the industry and average out the amount of time spent coaching, the average would approximate zero.

Carole: I'm going to give you just a little bit of pushback on that. Because I'm a nerd.

Lee: Yeah, please.

Carole: Same thing — in that analysis I did about managers, what I then found in another analysis is this: we've all heard that if managers spend at least 30% of their time coaching, their sales teams are going to improve. I wanted to know — is that really true for all managers? I did an analysis and found that the variable difference was managers who had been trained on how to coach and did it consistently were the ones that saw results. So it's not just a matter of how much time they spend, but what is the quality and context of the time? Do they have the tools? The training? The aptitude? The interest and desire? Or are they just getting through coaching so they can get back to inspecting?

Lee: Right. Or does coaching sound like — they're not actually coaching. They're telling them what they did wrong and what they should have done. They're not helping them develop skills through role play, through asking questions, through helping them dive into, "What was going on in your head when you did this? How are we going to change that going forward? Where does that come from for you?" That's what coaching is about — asking questions that help people realize something, not telling them what they should be doing.

Carole: "You suck at this, get better" — that's not coaching.

Lee: That's not helpful. "You need to make a hundred more calls a day" — not helpful.

One of my favorite coaching moments: a 13-year-old soccer player comes running off the field saying, "Mr. Levitt, Mr. Levitt, it worked! We scored! It worked just like we practiced!"

Carole: Imagine that.

Lee: Imagine that.

Carole: What's interesting — and this is another reason I'm starting to leverage AI — even Stephanie Boyer has talked about how many times we need to repeat a practice before it becomes a skill. Managers only have so much time. They're being pulled in multiple directions. Not only have they not been trained on how to coach, they're not afforded the time because leadership is pulling them in all these other directions.

But what I've also found is that you can practice something, and even when it doesn't go the way you practiced, because you know you practiced it, you know where to pivot. And that's the thing — too much practice or too much preparation can put some salespeople in a rut. Like me with my sheet music, it has to go this way. We don't want to burn a track too deep.

Lee: Right. Exactly. We want to know enough to be able to improv in the moment — but not so much that we're in a rut and can't deviate.

Carole: I love being in the moment with customers. I've said some things to customers in the moment that — oh my God, I would never have planned to say that.

Lee: I've done that as well. I've blown up deals that way, but for a good reason.

Well, the couple I'm thinking of — they were the right things to say at the time. I was on a call with a decent-sized prospect for the Oracle Autonomous Data Warehouse. I was the overlay, not the salesperson. The customer said, "We're too far along with our plans to change." The salesperson was saying, "Well, go back and change" — there goes all the internal relationship capital. Then the customer said, "Well, maybe we'll bring you in for phase two." And the sales rep got all happy. I said, "Here's the truth. You're going to get 80% of your value from phase one, and that's enough. Let's agree to part as friends."

The salesperson looks at me and says, "What are you doing?" I said, "I'm telling the truth."

Carole: I'm saying no because it's not the right thing.

Lee: And you know — "all happy" — I've seen this movie play out a hundred times. Nobody ever goes to phase two. I mean, a few do, but the reality is very few.

Here's selling 101 in the tech world: "Whatever you have right now was a bad decision. You probably didn't spend any time thinking about it when you made that decision. Now we want you to not spend any time thinking about it and choose us because we're better."

Carole: "You were stupid before. Take my word for it."

Lee: You were stupid before. Now you found us. Literally, I've heard that a thousand times. And again, we come back to the intent, right? Is the intent to be curious and helpful? Or is the intent to get your stuff bought, to get what you want out of them? That is what is wrong with sales.

Onboarding Should Start with the Buyer, Not the Product

Lee: In large organizations, I've been involved in global sales enablement planning and delivery. And much of it is, "Here's our product." Almost none of it is, "Here's how you should think about the customer."

Carole: Oh my gosh, this is my biggest pet peeve with onboarding programs. It's another reason I wrote Buyer First. So many onboarding programs start with the product, our process, our systems, and "Oh yeah, by the way, this is who our buyer is." It should be 80% on the buyer — immersion into their world and understanding them — and then everything else should flow from that. I have yet to see an onboarding program designed that way. Until I help them do it.

Lee: I reworked global enablement at Google. The product managers would come to me and go, "Here's our 90-slide deck about our latest thing." And I would say, "Okay. You have 15 slides. The first five are about the market — and I don't want to see TAM because no salesperson ever cared about TAM. Pick a couple of ICPs and describe their environment. Then a couple of slides about what we do and how it's relevant. And then the rest is: how do I get help? What are the right words? Who are the right people? How do I get help?" That was a huge revelation for product management at Google. "But it's just about us." It's like, well, yeah. Maybe. Or not.

Carole: Yeah. And it also doesn't stick. It's not applied to the context of the person they're going to be talking to. Ideally, if you don't have an onboarding program that equips your sellers to have initial conversations with your ideal customer by the end of the week, you're doing something wrong.

The Purpose of Selling Is Not Selling — It's Buying

Lee: Carole, you've got some passion for this.

Carole: A little bit. I go back to this: we're all salespeople. We've been selling our entire lives. Yet when you ask a kid today what they want to be when they grow up, none of them are going to say, "I want to be a salesperson." And that's what I want to change. Because sales is a noble profession. If you think about it, sales is all about connecting problems and solutions. Isn't that how we make the world a better place? By fixing things, by making them better?

Sales is all about behavior change. We're trying to help our buyers change a behavior, and we also need to change our own behaviors. Understanding the psychology and neuroscience behind behavior change has been key for me because that is what we're trying to do every day in sales. And change is hard. Change is scary and it's personal. We have to be comfortable getting to that level with people because otherwise it's just surface-level noise.

Lee: Jeff Lipsius says the purpose of selling is not selling. It's buying. It's helping people buy.

Carole: Yeah, and buying is about solving problems. If you're not solving a problem, then we're just filling a landfill with crap.

Lee: And the original definition of "to sell" is to give — to give value.

Carole: It's an exchange. It's not to take. It's to give. And what's ironic is that's what sales started as. But when the Depression happened and warehouses were full of inventory and companies were desperate for sales, they said, "We're going to pay you on commission and do whatever you have to do to sell it." Now we have the pushy, slimy salesperson as a result. We need to realize it needs to come full circle.

Lee: Some will. Some won't. Move on to the next one.

Where to Find Carole Mahoney

Lee: Carole, this has been a fabulous conversation. Where can people find you?

Carole: You can definitely find me on LinkedIn, which is where I spend most of my social media time. And then also — Carole with an E, and Mahoney with an E. Don't forget both of the E's. You can also find me on my corporate training website at UnboundGrowth.com or my speaker website, CaroleMahoney.com.

Lee: Thank you for the time. This has been a fabulous conversation. We need to spend some more time working on our combined focus of fixing and improving how salespeople think and feel.

Carole: Yes. I'm building my tribe.

Lee: Exactly. Thanks, Carole. It's been a pleasure.

Carole: Thank you, Lee. It was also a pleasure. Cheers.