Andy has over four decades of experience in sales and is one of the leading voices in the industry. His podcast, Sales Enablement with Andy Paul is one of the most popular sales podcasts. He’s written two bestselling sales books and his third, Sell Without Selling Out: A Guide to Success on Your Own Terms, was released earlier this year and we’ll be discussing it today.
In this episode, we’ll be exploring with Andy some of the themes from his latest book.
Linkedin: https://www.linkedin.com/in/realandypaul
Website: https://www.andypaul.com/
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Steve: This is Outside Sales Talk, the best podcast for outside salespeople. I'm your host, Steve Benson, and we're here to chat with the world's top sales experts so that you can get their best sales tactics to level up your game.
Steve: Welcome back to Outside Sales Talk. Today, we have Andy Paul with us, and he's here to talk about his new book. It's called Sell Without Selling Out. It's super popular. I've got it on my shelf myself. Welcome to the show, Andy.
Andy: Steve, thanks for having me. Thanks for buying my book.
Steve: I didn’t buy it. You sent it to me.
Andy: Did I? Okay. Well, there you go.
Steve: Which I appreciate.
Steve: We chatted last time. I think we were chatting maybe six months ago, and it was just coming out. So, you still had boxes of the books then. Now it’s been super popular. I've actually run into it in several places.
Andy: So, you can buy one for all of your team. How about that?
Steve: There you go. Maybe I will. You know, things like this are so valuable. And this has a really unique message.
Steve: So, just some background on Andy. He's been on the show probably two or three times already. Over the last four decades in sales, Andy has become one of the leading voices in the industry in terms of thought leadership around sales. His podcast, Sales Enablement with Andy Paul, is one of the most popular sales podcasts out there. I think I've been on it three times. It's definitely one to listen to. He's written two best-selling books, and we’re talking about his third here: Sell Without Selling Out: A Guide to Success on Your Own Terms. And it was released earlier this year, right?
Andy: Yes. Yeah, about six months ago.
Steve: Cool. Let’s jump into the book. There's a quote that you open your book with that I wanted to ask you about. It says, “Insist on yourself, never imitate.” For salespeople who are just starting and looking to impress people, how can they get the balance right between listening to their superiors and trusting their own intuition while being authentic to themselves?
Andy: Well, it’s harder when you first get started, right? Because you're in this brand new environment, and you walk into the job with this idea in mind of how salespeople act. Whether it's popular culture, movies, TV shows, books, whatever, everybody carries around this image in their mind of what a seller is.
Andy: Yeah, part of what your journey is in your first year on the job is to understand that that's not necessarily who you are as a human being. And that rather than trying to assume that you're playing a character like a stage actor or actor in a movie, you're really trying to be yourself and be the authentic you. Because by doing that, you’re going to come across better to the prospects as a human being, not somebody that's out there just to push your product or service on them. And this initial connection is so important because it opens the door to building credibility and trust with the buyer. So, if your first impression that you make on a buyer is one of being sort of pushy, playing a role, you know, "Hey, great to meet you" type thing, people see right through that.
Steve: Yeah, authenticity is so important. People can tell when they’re being sold to inauthentically, or when people are full of crap. They just know. I think it’s one reason it’s hard to sell things that aren’t great. It’s hard to be a part of a company that’s not really creating value. And it’s tough when sales management pushes people to be a certain way that isn’t right for them.
Andy: Well, and this is, unfortunately, one of the ills of our time in sales, that the embrace of certain sales technologies has encouraged this type of behavior on the part of managers. This idea that we can have a cookie-cutter approach to developing our salespeople. They just need to be a certain way, do a certain amount of activity, and everything’s going to work out fine.
Andy: And that’s not how the world works. You can't clone salespeople to be exact duplicates of someone else. I mean, you can listen to top performers’ calls, use the conversational intelligence system, and say, “Okay, they do certain things well.” But unfortunately, many managers use this very heavy-handed approach: “This is how Mike sells. Do what Mike does.” Instead, they should be saying, “This is what Mike does well. What can you take from that to integrate into your own selling? How would you put your spin on it? Let's experiment and see if it works. If it doesn’t, we’ll try something different.”
Steve: Yeah, that makes a lot of sense. I think often, especially with technology, managers push certain behaviors or characteristics on salespeople that aren’t authentic to them. What would you recommend a salesperson do if their manager is pushing them to act, be, or sell in a way that doesn’t feel right?
Andy: You always run into examples like, “Hey, this is the script that we sell with, so you read this paragraph. If they ask this, you read this paragraph.” They’re trying to, I think, mimic certain processes you run into in companies, especially companies run by engineers. I worked for a company like that early in my career, and it was a big thing. They saw sales as, if you do this many lead generation activities, it will yield this many first meetings, which will yield this percentage of second meetings, which will yield this percentage of revenue. And that’s not exactly how it works.
Andy: Over time, everybody has their own ratios, their conversion ratios, right? Looking back on my own selling, I certainly had my own. So I knew at one level what I needed to do, but I started from a different perspective, which was: My goal from the beginning was to win more than I lost. Now, that’s completely foreign to most people in the software world because win rates for SaaS companies tend to hover around 20%.
Steve: We can get into the reasons for that, but it shouldn’t be that way. You should be able to set a bar, both individually and as an organization, and say, “This is my benchmark, and this is what I want to achieve.” Once I find the recipe for making that happen, then, yeah, I can scale it. But everybody sort of works backward these days. And so, if you're an individual seller, getting back to your question, it’s like, hey, if you feel like you're being forced to sell in a way that's just not aligned with who you are, you have two choices.
Andy: You can do what I often did early in my career and say, “I don’t think that’s going to work for me. I have a different way to do it, and I think it will be better for me, and it will enable me to hit my numbers.” And if you can’t get the space to do it your way, then you go find a situation that will enable you to do that. There are plenty of great sales managers out there who understand that their job is to help you become the best version of yourself. And if they can do that, you’ll perform at higher levels, be more fulfilled, and maybe even stay longer than most salespeople do.
Steve: But if you're in a situation where it's, “Hey, just execute our process. The process is paramount,” people are going to leave because they're not bringing any of themselves to the work. And this is what buyers want. Buyers make their decisions in large part based on their experience with the individual seller. In so many industries, especially software, but it's not just software, there's so much competition, and in the buyer’s mind, all the products and services are alike.
Andy: So when the products are perceived to be alike, what are the difference-makers that enable one competitor to nudge out another? It's the buyer's experience during the buying process with the seller.
Steve: Yeah, so your sales process, your buyer's process is so important to customize. And I think that maybe that's the logic a sales rep can use when they're being pressured to conform to a process. They could say, “Hey, I know this is the talk path we use in this situation, but I was customizing what I was doing because of XYZ. This customer has this personality type, works in this industry, at this size, and so on.”
Andy: Right. And to your point, no two of those people are going to be alike. There’s always going to be something unique about what they want, and if you don't recognize that, then you're just trying to shove them into a box. You can’t just say, “I think you fit in this box.” Buyers resist that because, in their mind, they’re not the same as every other company. They’re different. They have different people, different concerns, and if you treat them like everyone else, that’s hugely problematic for them.
Steve: And I guess a lot of this gets back to how you titled the book and why you started it the way you did: the concept of selling out that you’re trying to get people to avoid. If you feel like you're being pressured as a sales rep to sell out, how can you rid yourself of that pressure without losing performance and still being a winning sales rep?
Andy: Right, but there are two dimensions to it. One is, are you in the right environment? If you're not in the right environment, ultimately, maybe the answer is that you have to change environments. There’s a lot of people out there writing about how to earn seven figures. Well, sure, some of it is what you know and who you are. But those two things have to be applied in a situation that enables you to win the type of deals that allow you to earn that kind of money.
Steve: So, yeah, it’s a great aspiration to earn seven figures, but there are going to be relatively few places where you can do that. If that’s your goal, you need to make sure you’re in the right situation.
Andy: In the rap songs now, they’re talking about eight figures.
Steve: I've got bad news for us here.
Andy: Eight figures. We gotta push eight figures. We’re doing it!
Steve: Yeah. I’d be happy if more than just a few handfuls of sellers made seven figures. But yeah, you have to find the right situation, and if that’s not your thing—maybe the income isn’t the top priority, but you want to be fulfilled, work with smart people, have control over what you're doing—then you have to find the right situation. Those opportunities exist, but there are also lazy sales leaders out there who think the process is driving success. No, it’s individuals that drive success. As a leader, your job is to develop those individuals and give them the freedom and flexibility to succeed.
Andy: I wrote about this in the book: I worked for a senior VP once who got frustrated with me because I never said yes automatically to almost anything a sales leader or boss said to me. I knew that if I just blindly followed their advice and didn’t win the deal—and if I did that multiple times and didn’t hit my numbers—who gets fired? Me or the person who gave me the advice? It was me. So I decided early in my career that if I was going to get fired, it was going to be on my own terms.
Steve: I can’t always say that was easy as an employee, but I delivered. I performed, I made a club. And it wasn’t like I was a loner or outside the boundaries of what the company was trying to do—not at all. It was just that I had my own take on it, my own spin on it. I knew I was unique in the way that I looked at the world, in my curiosity, and in the way I asked questions.
Andy: As you grow throughout your career, you’re going to have multiple people that influence you. I was influenced heavily by two particular bosses early in my career, and they, not coincidentally, gave me a lot of room to operate but also had incredibly great advice and guidance. So as a seller, you have to be open to lots of different sources of input and information. Take the things that align with who you are, your values, and your character, and experiment. Constantly experiment.
Steve: There’s another quote from Ralph Waldo Emerson in the book, besides the one you mentioned at the beginning, which says, “All life is an experiment. The more experiments you make, the better.” I’m a huge believer in that. That’s the way I’ve built my career—just keep trying new things.
Steve: Yeah, I had a similar experience to what you described, and it produced one of my philosophies on sales. My philosophy is: never hire a strategy consulting firm to come in and do your sales strategy and sales process. I was at a company—who will not be named, but it’s pretty obvious if you go over my LinkedIn—that hired McKinsey, I think it was. It was one of the big three strategy consulting firms. They do great strategy work, but they brought them in to build the sales process and the go-to-market process for our suite of products.
Steve: It was this huge, like, six-month thing. I don’t know how many millions of dollars it cost, but it was a lot. At that time, we had maybe 250 sellers. Not a huge team, but a decent size. And the stuff they came out with was comically bad. It was busy work. It wasn’t helpful. It was very formulaic—about as cookie-cutter as you can imagine. And it wasn’t done by people who knew sales. They didn’t know the craft of sales, they didn’t know the customer, and they didn’t know how this product was sold. It was like they read four books about sales and shoehorned it all into one Frankenstein monster.
Steve: And I just proceeded to ignore it. I was a cocky little bastard at the time because the year before, I had been the top seller in the organization, so I was able to be a cocky little bastard. But I was like, “No, I’m not doing any of this. This is all a waste of time. This is all wrong and all stupid.” And sure enough, by the end of the year, everyone had just started ignoring it. It got tossed in the round file under the desk.
Steve: That’s an important thing for sellers to realize: you have to learn to trust your gut. As you get more experience and exposure to different situations, who knows better what’s going to work for you than you? That doesn’t mean you’re closed off to input—far from it. The point is that you become a discerning consumer of advice, guidance, and input because it’s your career that’s at stake.
Andy: Yeah, I post things on LinkedIn all the time, and I think it’s all great—but it’s not all for you. Some of the things I write about will work for you, and some won’t, and that’s fine. You just have to become a discerning, discriminating consumer of sales information and advice from all sources.
Steve: And you’ve got to try things, right? If something strikes your fancy, try it. If it doesn’t work, fine. Give it two or three tries, see if you can tweak it, and then move on. But that’s the part we’ve lost in sales over the last 10 to 15 years—this idea that sales is fundamentally an apprenticeship. We’ve moved away from that. Sales is a craft.
Andy: Yeah, and when I joined my first sales role about 20 years ago, they thought it would take me a year to really understand enough to sell. They didn’t call it an apprenticeship, but that’s what it was. I was basically shadowing a senior sales rep for the first year. This was at IBM, which had a famous sales school—I think they still have it now. And that’s how they viewed it. They didn’t call me an apprentice, but that’s what I was.
Steve: Yeah, they were like, “You don’t know anything. We’re going to teach you how to do this. Follow this guy around—he knows how to do it. Watch closely.” Part of the reason they were willing to make that investment was that they viewed employment as a long-term thing. Back then, the idea was that employment was for life. I think that’s changed now, not just for IBM but for everyone. Now, a two-year stay at a company is considered a long time.
Andy: That change—where companies no longer view employees as long-term investments and employees don’t view companies as long-term employers—has been bad for everyone. It’s better to think carefully about who you bring onto your team. It’s better for employees to think carefully about where they want to work. What kind of company do you want to work for? And then, make it a long-term relationship. Both sides, the company and the employee, get more out of it when it’s a longer-term thing.
Steve: Well, I think it’s important for salespeople to have patience. There were two particular junctures in my career where I had the opportunity to jump ship, to make more money immediately. But I knew that staying would provide opportunities I wouldn’t get somewhere else. And it’s those opportunities to learn and grow that you miss if you jump too often.
Andy: So I think sellers—especially today—who have such short tenures are missing out. I think the average tenure in the Valley now for an AE (account executive) is less than a year, based on stats from last year.
Steve: That’s why I don’t hire AEs in the Valley. I mean, it’s a broad trend in the tech space, but it’s especially pronounced in the Valley. And what do you learn if you’re only in a place for a year? Not as much as you think. You learn the basics about that company and the product, but you don’t get the opportunity to really understand your customers or develop your craft.
Andy: I have people on my sales team who’ve been here for seven, eight years. They know so much more, and they’ve had so many leadership and growth opportunities. And they’re the ones first in line for promotions. Most of the time, it’s better to promote from within rather than hiring from outside. It’s about growing together.
Steve: But more importantly, Andy, it’s by staying a little bit longer that you truly understand the customer. You develop your business acumen and understand how your customers use your product to make money. You start understanding business more deeply, and that’s what helps you grow in your career.
Andy: Yeah, over time, you’re worth more to the company, and the company becomes worth more to you. It’s not just about skills—there’s understanding the customer, the product lines, and how the company works. And the more of those things you change in your career, the more you lose. The deeper you go within one company or industry, the more valuable you become.
Steve: Sure, you could switch to another laser company if you're in medical device sales, for instance, and you wouldn’t lose much. But if you switch from selling lasers to selling dental equipment, you’ve lost a lot of knowledge, because dentists are a different market from doctors. The more often you make those kinds of changes, the more you lose.
Andy: Yes, and you become worth more to your current company because of your domain knowledge. But to the shoulder joint company? You’re just another rep off the street. Whereas at the laser company, you’re worth a lot because of everything you know about the product, the market, and the customer.
Steve: Exactly. The longer you’re at a place, the more your value increases because of that domain expertise. And that value gets shared between you and the company. It’s why raises exist—you’re worth more to the company as time goes on, and the company should compensate you accordingly. At the end of the day, it’s a good company that’s willing to grow with you.
Steve: Yeah, and when I started at Allstate Insurance and IBM, they wanted you to spend your entire career there. I knew people who retired with a gold watch and a pension plan. That was the ideal back then, but that’s all changed now.
Andy: Yes, it has. The 401(k) became the norm in my career. I never worked for a company with a pension plan.
Steve: Exactly. And that’s why I don’t blame people for changing jobs, especially in tech or the startup world, where it’s a way to build wealth. But the key is, if you’re jumping jobs every 12 to 18 months, you're not investing in a ton of equity, but you're also not investing in yourself.
Andy: Right. And at some point, people are going to look at your resume and say, “Okay, you’ve worked at five different companies, but what have you learned? What can you really bring to the table?”
Steve: Exactly. You may have been at five companies, but you’re still at a junior level. You never progressed beyond that because you didn’t stay long enough to move up. You might have made lateral moves, but you’ve never experienced growth, and now you’re stuck at the same level.
Andy: Yep. And so there’s no blanket statement here like, “Don’t change jobs.” The key is to make sure that when you do change jobs, you’ve gotten everything you can from that position. Did you get mentorship? Did you gain experience managing larger or more complex accounts? If so, great—now you’re ready to move on. If not, maybe consider staying a little longer to get those things before you leave.
Steve: Yeah, absolutely. I’ve had one instance in my career where I joined a company, and within 24 hours, I knew it was a mistake. It took me about six months to leave, but I probably should have done it sooner. So if you’re in a bad situation, get out, but if you're in a good one, make sure you’ve gained everything you can before you move on.
Andy: Exactly. It’s your career. No one else cares about it as much as you do. No one else cares about your success as much as you do. So you have to take responsibility for it and make thoughtful decisions.
Steve: Right, and the good news is, there’s a lot more information available now. You can backdoor reference-check companies through sites like Glassdoor or by talking to people who’ve worked there. So do your homework before you make a move.
Andy: Absolutely. And you have to take a hard look at your own situation. Sometimes people bounce around for the wrong reasons, and sometimes they don’t leave soon enough when they should.
Steve: Yeah, totally. It’s like the saying about hiring and firing—hire slow, fire fast.
Andy: Yeah, although I’m not always sold on the “fire fast” part. I think you should give people a chance to succeed. But if it’s clear that it’s a mistake, then yes, make the move quickly. Same goes for joining a company. If you realize early on that it’s not right for you, it’s often better to go back on the market sooner rather than later.
Steve: Exactly. Well, let’s refocus on your book because I want to keep digging into the wisdom in there. One of the chapters in your book is called, “There’s One Question Every Buyer Will Ask You.” Can you talk about that? How does trust play into the sales process?
Andy: Sure. In that chapter, I tell a story from my own experience, but the gist is this: every customer is making a decision about you. They’re asking themselves, “Why you? Why should I trust you? Why should I work with you? Why should I buy from you?”
Steve: They’re not usually asking, “Why your company?” but “Why you, personally?” And they don’t usually verbalize this question, but they’re thinking it. And you can’t answer it with words. They have to experience you—how prepared you are, the first impression you make, whether you’re more interested in them than in yourself, whether you lead with questions. All these little things help you build that trust.
Andy: Right. So, the question, “Why you?” is something every buyer asks themselves about the seller. And the only way to answer it is through your actions. Are you showing up prepared? Are you genuinely interested in helping them? Are you building a real connection with them as a person? This is where trust starts to build.
Steve: Yeah, that makes a ton of sense. And for a salesperson who’s looking at their territory and thinking, “I get it, trust is important, but how do I build more of it?” What are some tactical steps they can take to improve?
Andy: Sure. The first thing is to be more interested in the buyer than in yourself. That’s the essence of what I call “selling out”—when a salesperson puts their own interests before the buyer’s. So, you need to shift that and show genuine interest in the buyer. Have you done your homework on them? Have you looked at their LinkedIn? Have you done a Google search? Maybe found them on social media? Spend a few minutes gathering information, because you might find some common ground that helps you connect.
Steve: Right. It’s about building that human connection. It’s not just small talk; it’s about showing them you’re invested.
Andy: Exactly. And I recommend something I call the “ask five” rule. When you meet someone for the first time, challenge yourself to ask five questions about them before you say anything about yourself. You can even practice this in a social setting. Next time you’re at a party, try asking someone five questions about themselves before you talk about yourself.
Andy: It’s an exercise in being genuinely curious and training yourself to focus on the other person. This helps build that connection because we, as humans, are wired to respond to people who show interest in us.
Steve: That makes sense. And it’s not just a sales skill—it’s a people skill.
Andy: Exactly. I joke that it’s like learning how to make a friend. When you meet someone at a social event, like a kid’s birthday party, you ask them about themselves, their work, their family. You don’t just start talking about yourself, right? That’s the same motion in sales. You’re building a rapport by being curious and asking questions.
Andy: It’s basic human interaction. And I think this often gets lost in sales training, where we’re told that buyers don’t have time for small talk. But the truth is, small talk plays a huge role in building connections.
Steve: Yeah, absolutely. People want to feel like you’re interested in them. So, the first impression really matters. Be prepared, ask thoughtful questions, and show that you care.
Andy: Yes, and then follow that up with deeper discovery. I talk about this in the book—the importance of going beyond surface-level questions and really understanding the buyer’s challenges. Discovery is too often treated like a checklist, where salespeople just go through the motions. But the goal should be to find out what I call “the one thing,” which is the most important challenge the buyer is trying to solve.
Steve: Right. Every buyer has a top priority.
Andy: Exactly. And it’s the seller’s job to uncover that. The way to do this is through trust. You have to earn the right to dig deeper into their challenges. That’s when you can start asking what I call “impact questions.” These are questions that force the buyer to quantify the impact of their current situation or the potential impact of making a change.
Andy: For example, you could ask, “What would it mean for your team if you were able to increase revenue by 5%?” When you get them to start thinking in those terms, it becomes more real for them. They begin to visualize what success would look like.
Steve: That’s great advice. And I love that you emphasize follow-up questions, too. It’s easy to just move on after getting an answer, but asking, “What else can you tell me about that?” can really open things up.
Andy: Yes, exactly. Follow-up questions are crucial. If you ask a surface-level question and get a surface-level answer, don’t just move on. Push a little deeper. The buyer will appreciate it because it shows you really care about understanding their situation. Simple questions like, “What else can you tell me about that?” or, “How would that impact your team?” can lead to much richer conversations.
Steve: Right. And at the end of the discovery, you suggest asking, “What are we missing?” I love that. It forces the buyer to take a step back and make sure nothing important has been overlooked.
Andy: Exactly. When you think you’ve wrapped up the discovery process and identified the key issue, that’s the time to ask, “What are we missing?” It often prompts the buyer to think more deeply and bring up something they hadn’t considered before. It’s a powerful way to make sure you’re not leaving anything on the table.
Steve: Yeah, that’s a great approach. It’s about digging deeper, creating a vision of success for the buyer, and co-creating that vision with them. When they buy into that vision, you’re much more likely to win the deal.
Andy: That’s exactly right. In fact, there’s research from Forrester that shows if you’re the first seller to get the buyer to buy into your vision of success, you’re 65% more likely to win the deal. It’s all about helping the buyer see what success looks like with your solution.
Steve: And that shortens the decision cycle, too, right?
Andy: Yes, it can. By being the first to build trust, to understand the buyer’s key issue, and to co-create that vision of success, you not only increase your win rate, but you can also shorten the decision-making process. The buyer is more likely to make a “good enough” decision rather than spending extra time looking for alternatives.
Steve: Fantastic. Well, Andy, this has been an amazing conversation. You’ve shared so much wisdom. Before we wrap up, let’s jump into our quickfire segment—Sales in 60 Seconds.
Andy: Sure, let's do it.
Steve: What’s the best way for salespeople to quickly establish rapport with their prospects?
Andy: Lead with questions. Do your homework, and find common ground right away.
Steve: What’s the most common mistake salespeople are making today?
Andy: Pitching too early before they truly understand the buyer’s needs.
Steve: With all the new sales tools on the market, do you think salespeople are better off today, or are we over-processing things?
Andy: Unfortunately, I think we’ve gotten worse. We’re not using the tools the right way.
Steve: What’s one daily habit that you think makes salespeople more successful?
Andy: Read for 10 to 15 minutes every day.
Steve: What’s the best sales advice you’ve ever received?
Andy: Well, after 1,100 podcast episodes, it’s hard to pick just one piece of advice, but I’d say the importance of being genuinely curious about your buyers.
Steve: Love that. And finally, how can salespeople avoid selling out and build better connections with their buyers?
Andy: Put the buyer first. Make it about them, not you. Build trust by showing up prepared, asking good questions, and genuinely caring about helping them succeed.
Steve: Amazing advice. Well, Andy, thank you so much for being on the Outside Sales Talk podcast. Where can people find you if they want to learn more or get in touch?
Andy: You can find me on LinkedIn—just search for Andy Paul. You can also visit my website, andypaul.com, or send me an email at andy@andypaul.com.
Steve: Fantastic. And for everyone out there, if you’re in field sales, don’t forget to check out Badger Maps. It’s the number one route planner and will help you sell more and drive less. Get a free trial at badgermapping.com. And if you know any other sales reps who would benefit from Andy’s insights, share this episode with them. Andy, thanks again for being on the show!
Andy: Thanks, Steve. It’s been great. Take care, everyone.
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