HOW TO BUILD THE MINDSET OF A #1 REVENUE PRODUCER IN B2B SALES
2 Jan 2025 · 46 min
In this hour‑long interview, host Brian talks with veteran B2B salesperson Paul Hutchberg, the former #1 worldwide rep at Dell and a long‑time strategic seller at ConnectWise. Paul walks through his career trajectory—from early financial‑services work, to Dell’s high‑velocity transactional environment, to strategic, C‑level selling at Gartner and ConnectWise. He explains how a deep competitive drive, cultivated from childhood, fuels his daily performance and how that mindset translates into concrete sales habits: relentless preparation, anticipating objections, building rapport, and owning the entire sales process from discovery to close. Paul contrasts “grinder” tactics (long hours, high activity) with “working smarter” (anticipation, territory mastery, cross‑selling, and leveraging trust). He shares stories of territory swaps, the importance of being the trusted advisor rather than a product pusher, and how he maintains performance without burning out—using focused work, family time, and occasional vacations. The conversation also covers coaching BDRs, the limits of detachment in prospecting, and why mindset alone isn’t enough without skill, process, and emotional regulation. The episode ends with practical takeaways for salespeople seeking to become top revenue producers.
Chapters
Boy, do I got one for you today. Great guest, great topic, and something that I think we all can apply even though it might be not your driver, your motive. But for a lot of us it is. And it's okay if you have a different motive. You just have to tap into it. And today's motive, or at least for the guest, is competitiveness. Nothing new. We've heard it 100 times. But today's case is a little bit different. Let me explain. We have somebody who worked his way up to be the number 1 worldwide rep at Dell. Now imagine that. Out of 26,000 salespeople, he came out number 1. We'll get into that. Now, let's say competitiveness isn't your driver. Maybe it's money. Maybe it's success. Maybe it's People say, oh, I want to help people. Well, good. You can do that too. That's what sales is all about. But what happens if you really connect to it? You really understand it, not just at the end of the quarter or the end of the month or end of the year, but every day. And then you look at that mindset and think about what that mindset can do over a long period of time consistently. Year after year. That's where the magic happens. Because in today's case, you're going to see a mindset that is pretty much unstoppable. And all the excuses and the rationalizations and the victimhood that everyone feels, including you and me, he has plowed through. And we're going to get into it with a lot of cases today. So, even if you're not that competitive, listen to this because what you hear is what is possible because somebody did it. Many different territories over a long period of time and at the same company. He's not at Dell anymore. He's at another company that isn't well known. So, I know you're thinking to yourself, well, Dell's a brand name and everything. Yeah, yeah, yeah. Okay, okay. I hear you rationalizing already. Let's get into this interview. Now, if you really want to match mindset with skill set, that's where the magic happens. Because today the person clearly is a hard worker and has skill set, but anyone can work hard, but you need the skill set. Go to b2brevenue.com. check out how to develop your skill set and come on that hero's journey with me. Let's get into the interview. I'll sum it up at the end. Hey Paul, thanks for joining us today. As a way of getting started, give us a little background on yourself.
Yeah, so I'm Paul Hutchberg. Been in sales for about 23 years. Some of my background is I started in financial services in the Boston area. providing life insurance, things like that. I realized pretty quickly that wasn't for me. I wanted to sell more business to business. Ended up going to Dell in Austin, Texas. That really kind of transformed my sales career, started building my success, my confidence. I moved up the ranks there fairly quickly and ultimately ended up in the SMB acquisition space. And my claim to fame, and a long time ago, but in 2006, I was number one of all sales. And I always will remember the day my manager kind of showed me the stack rankings, which was pretty cool because there's like 20,000 sales reps at Dell. From Dell, I ended up working at Gartner, spent a few years at Gartner. Gartner, phenomenal training, gave me the opportunity to work in the midsize space and work with kind of CIOs and their direct reports. Since Gartner, last 13+ years, I've been at a company called ConnectWise. And been selling to managed service providers, technology companies. Really, I guess the claim to fame there is when I started, I was employee 107. We're now over 3,000 employees. We're a global company and, you know, we're nearing on $1 billion in sales. And so, you know, I was part of a sale of the company as well with the original owners and potentially maybe a second one. down the road with the new owners, you know, so it's been really exciting.
So you were number 1 in all of Dell?
All of Dell. Yep.
Wow. Percentage of quota, total revenue?
No, they had— at Dell, they had what— they had a stack ranking. So it wasn't just quota. It was like selling certain lines of business and close rate. And they had all these metrics. And I was number 1 in 2006. Excellent.
How'd that make you feel?
Amazing. Yep. And I remember too, the, the senior director emailed my dad, which was kind of cool. So he came over to me, he came over to me and he said, what's your dad's email address? And he sent an email to my dad. And so, you know, that feel even better? Yeah, yeah. I mean, I'm one of those people that, you know, I've always looked up to my dad. And it was something that, you know, I kind of stumbled at the beginning of my career. I didn't do very well in financial services, and then it took me a little bit of time to kind of land at Dell and get my footing and understand sales. And even when I started at Dell, it was very overwhelming for me. Most of the people that I was training with were senior, they were very technical, and what I realized very quickly is that wasn't my skill set. And so, you know, I realized I could build rapport very, very quickly, and I just kind of focused on understanding You know, what is they were looking for, and then just went for the kill. And so, you know, when I was at Dell, it was very transactional for me, and I was able to close deals much faster than any of the other reps, which attributed to my success, you know, opposed to geeking out on the technology, because honestly, at that point in my career, I didn't really understand it. And so I didn't spend too much time, you know, talking about it. It was more, you know, what's your budget? When are you looking to buy? All right, what's your credit card number? Let's move on.
You know, very transactional.
Very transactional. Yeah.
But what you're selling today isn't transactional, is it?
No, no. So I work with technology companies. We sell a suite of products from service automation to remote monitoring management to services like Help Desk Knock. It's a white-labeled service to technology companies. So if you think about any organization that you go to that has technology, they're probably using ConnectWise products behind the scenes. And I work— I'm a strategic, what we call strategic sales exec. So I work larger deals at ConnectWise, and they have longer sales cycles with them. And, you know, the average, I would say, annual contract value is probably, you know, $50,000 to maybe $75,000 in that range. And, you know, I think I carry about a $2.5 million quota.
And what drives you? What gets you up in the morning? What fires you up? Because clearly you're a competitive guy.
Yeah. I mean, I would honestly say at this point in my career, I would say the drive is just, just being number one. Like, I, you know, at least at the company that I'm at, right? You know, yeah. Everyone's goal is to beat me and they tell me that. And it's kind of fun, right? To have a goal that they're never going to achieve. Right. No, but, you know, You know, joking aside, it is that competitiveness. Candidly, I don't know how many people are going to watch this, but I mean, I could live off half of the money that I make and live comfortably. Like, one of the things that my wife and I, you know, have done over the years is that as I've made more money, you know, we've looked at it as like savings or other assets. We don't just spend and spend. And so, you know, I literally could live— so it's not about the money, even though obviously sales money is important. But it is about the competitive aspect of what I do. And it's beating what I did last year and certainly being number one and then destroying my competition, right? I often joke, I kind of feel bad for my competition because they have no chance in a head-to-head deal against me because I'm going to do whatever it takes to win. I'm going to build rapport. I'm going to do a great discovery. I give out my cell phone to these people because if they You know, they say, oh, I'm concerned about support. I'm supportive about that. Don't worry, here's my cell phone. You call me, I'll take care of it. I've been with the company forever. I'll go all the way up to the CEO if I have to do that for you, you know? And so it's building that trust with them that, that ultimately if they buy from me, that I'm going to take care of them. And that's really, I think, a big aspect of sales is they're not buying ConnectWise or fill in the blank company. They're buying from, from me. And ultimately I have to represent the company. You know, pre-sales and post-sales.
And where's this competitiveness come from?
You know, I've always had it. I was always, even growing up, I was a sore loser. And, you know, I actually wanted to play professional basketball. And then, you know, as my dad told me, you know, you know, white Jewish, I'm not going to be over 6 feet tall and I'm 5'9. I really didn't have a shot there. So as those dreams you know, went to the wayside as I hit high school, you know, sales is kind of the next, next best thing from— for someone who's super competitive, you know, and, and always wants to be at the top. And then I really got a taste for that in my Dell days where everything there was super, super competitive. They had stack rankings, you know, they had recognition on a monthly basis, you know, they really did things the right way. Um, and, and I've seen that throughout other organizations. ConnectWise does the same thing, you know, with trips and things like that. And you know, there's an element of you want to be recognized. You want to be the top, you know, and and you want to be you know the best month after month, quarter after quarter. Now with that, you know, there's a lot of work that goes into it. So I mean, you know, anyone anyone who wants to be, and that's what I talk to you know many reps. I do a lot of training with with with new reps, you know, around sales is that you know if you want to be the best, it's literally day in day out. It is a commitment. You're taking you know less vacation time. You know, you're working every end of month, every end of quarter. You're getting in early. You're doing things above. It's not just about working hard too, because you need to learn your technology. You need to have your value story, right? You need to go into these opportunities because a lot of times you only have one shot, and if you blow it, that prospect's moved on, right? So I make sure not to blow it. I make sure to go in. I'm prepared. I know, you know, just in a quick five or ten minutes with a prospect, what their issues are, even if they don't know what they are, because. I know the space, right? I know what I'm doing. And I truly have kind of no fear in the aspect of when I'm talking to a prospect to, you know, tell them how, you know, where they're wrong, where they're right, what they need to do and why. And a lot of times I get prospects who are thinking about things that they weren't thinking about was even a problem, or they had a problem that they thought they had, which isn't really a problem, you know, type of thing. And I think that's extremely valuable because I'm bringing value to the table to them. And then that helps throughout the rest of the sales cycle to then when we get to the demos, right? And we get to the close and we get to those aspects of it. You know, I think the biggest misconception out there is that, you know, the demo is what sells people and that, that's not accurate at all. You know, the demo just checks the box, right? We all assume every technology company out there is gonna give a great demo, right? That's what they do. That's why they have engineers. So they just check that box. It's really what you've done on the front end to position, you know, your organization, your product, your value story, you know, how you're different yourself as the sales professional, and to get them excited and keep them excited through the process, right? That's the way I view it.
And who's the point of contact at the customer side? Is it CIO? Is it chief architect? Is it operations?
Yeah, I mean, it could be the CEO, it could be someone at the C-level— CIO, CTO, CFO— or it could just be one of their direct reports, you know. And so it varies. And from what we sell at ConnectWise, you know, we have technical products which sometimes don't land necessarily with the CEO. So it could be like the IT team, right? So certainly winning them over and then helping champion that to the executives for price and budget. We also have a, you know, a service automation tool that touches the entire business. Certainly the CEO is going to be involved because that's something that runs their entire business. And so we typically do get access to those people, but it varies on which technology we're selling.
And what makes you good at this? I mean, because I'm sure you've been there forever. You've seen good, great, and okay. Probably pretty bad to compete against people.
Yep. Yeah. I mean, you know, I think it starts with, you know, I think I just check all the boxes when you look at salespeople, you know, from, you know, my aptitude to learn technology, to talk to people that are evaluating the technology as someone who's not an engineer myself, who's not super technical, but can have that conversation with someone Who understands sales and sales process, right? So that I can navigate the prospect through from a discovery all the way through close, you know, in a, in a, you know, in a process that makes sense, you know, that moves it along in a quick fashion, right? I'm not putting roadblocks in there to create steps. I'm accountable. I'm confident. You know, I have conviction what I'm doing. I truly believe in what I'm selling. And I think that's another big component. And I'm naturally curious, right? So like when I'm talking to a prospect, like I'm always kind of curious how they're doing things, why they're doing it, have they considered other options, you know, and having those conversations with them, it really helps. Where it's not— I work with a lot of reps where, you know, a lot of times their discovery is super short. They just can't wait to pitch stuff, right? And just kind of, you know, throw up all over the prospect type of thing. And that's You know, it's tough to listen to, right? And it's like, spend a little bit more time getting to know them to understand, because then when you transition into your sales pitch, then you got them. Then you can bring back things that they said, that they talked about, that they didn't even realize by telling me is an opening for something else that I sell, you know? And that's where a big success of mine has been, is that I'm very good at cross-selling and upselling and creating value.
And You know, Dell probably gave you some technical experience here, but was Gartner helpful and more of a strategic sale, an intangible?
Yeah, Gartner was super helpful from a training perspective. They gave a lot of insight into, you know, how to navigate that conversation from a, like a, you know, from a value standpoint with C-level executives, you know, how to build Yeah. Rapport. And because, you know, Gartner was, was, it was total opposite, right? If you look at Dell and Gartner, Dell is very transactional. Gartner, and I had a few different roles at Gartner, but for the most part, I was working with like pretty large organizations and C-levels that had pretty large budgets. And so, yeah, when you got into that, I, it couldn't be transact— I couldn't use the same way that I sold at Dell. It was vastly different, you know, when I went into Gartner and it was really about building that rapport and trust, you know, with these, you know, with the CIO, with the CTO, you know. And if you got access to a CFO, even better, you know, type of thing. Rarely were you working with a CEO, you know, type of thing. But they had phenomenal training there, um, and so I gained a lot. I've had a lot of different training throughout my career, and I, I wouldn't say that I've adopted anything specifically. I think it's more that Um, I've incorporated into kind of my personality, and ultimately I'm just comfortable, you know, in my own skin, if you will, in terms of when I'm selling, I'm just me, you know. And, you know, I, I, you know, I think I'm just, you know, I hate to say it because people say it, I'm just likable, I guess, you know. I remember my, um, you know, again, going back into high school, I didn't get cut from my baseball team even though it was horrible because the coach said he just liked me too much, so he kept me on the team, you know, type of thing. And so, but, you know, when you're selling, I think that's, that's a good thing if you're naturally likable and it's someone that they can, you know, trust and, you know, kind of work with that, hey, this isn't just a sleazy sales guy just trying to make a commission. You know, I walk around like I've got a million bucks in my pocket at all times. I don't need the sale as much as you need my solution, right? And that has always been, you know, kind of my philosophy, even when I've struggled in my career, even when, you know, early on and I had to, you know, sleep in my car and, you know, and had to do things that you're like, you look back and like, oh my God. And even today, You know, even though I don't have to do that, right? I've had a lot of success. I make a good living, but I still adhere to the same things, you know.
And when you hear other reps say, well, I'm not competitive, how does— what's your reaction to that?
They're in the wrong business. Like, I, I don't understand how you can't be in sales and not be competitive. Like, it is the most competitive, you know, business. And it's so difficult. It really is like the amount of Because here's the thing, right? And I don't want to knock anyone who's an engineer, who's in sport or consulting, but, you know, they get a salary, they come in at 9, they leave at 5. Like, there's plenty of times where— now there are engineers, I got, I have one on my team, phenomenal, who he'll go above and beyond, right? That's not the norm. Most of them check out. Sales, you can never do that, right? Like, I work all hours. I got people emailing me weekends. I got to get back to them. You know, sales managers, same thing. It is a job that is relentless, right? And it's constantly— you're getting rejected and you can't take it personally, right? If you're not competitive, competitive with yourself, with your peers, with your competition, I'll be honest, there's other careers out there that are better suited. Like, I just— I don't— I don't see it personally.
Yeah, because I've talked to a lot of people about this and how do you turn it on and turn it off?
I don't know either. Like, I'm just always competitive. Like, and it's funny too, is like when someone's beating me for a month or a quarter and then I get pinged by their manager or them or my manager and I'm like, okay, we'll see. Yeah, just give me another couple months, you know. You know, but I love that stuff. Like, I thrive on that competition. And, you know, the reps that are always— it's always the same reps. I've seen it every company. ConnectWise is no different. It's the same people that are at the top every year. And they have that same drive. And, you know, the people that are in the middle are always in the middle. The people at the bottom sit at the bottom. The other thing I'll share while I'm thinking of it too is because the people that are at the middle or the bottom, their always excuse is territory or their BDR or lack of leads or something of that nature. And so just to give you a little background at ConnectWise, because I thought it was kind of interesting, the, the, the former CRO, he used to joke with me that at some point he's just gonna give me like North Dakota because literally I had like a territory and I was crushing it. And then the rep who had Florida was the bottom rep. And I was like, I'll take it. Because the way I looked at it was he wasn't selling, so there's plenty of opportunity. So I went to Florida, crushed it, number one. And then the Northeast came available. And similarly, it was similarly— that's not a word. The rep there was the bottom rep and no one wanted that territory. And it was Massachusetts, which obviously I'm from originally, so I like that, and New Jersey. But New York came available. Everyone wanted New York. I was like, I'll take Massachusetts and New Jersey. So I took that territory. I was number 1 for 2 years. So what did they decide to do? It was unfair. So they broke my territory in half, but no one wanted it. And the rep who was in there was in last place. So maybe at some point it's not the territory, maybe it's the rep, right? And so, you know, I always kind of find that funny, you know, so, and it is what it is. And I think for every top performer out there, They know it. They know the work they put in, the knowledge that they have, and you can literally put them in any company, in any territory, and they're going to absolutely crush it. And that's the way I feel about myself and any of the other top reps that I work with. And I've seen it.
Yeah, because they have to make it something other than them. Otherwise they have to face themselves. And I—
that's actually a good point is, you know, that's something I've done over my career as well. Right. I'm in sales now 23 years. Is that things that I was not good at, right, like at Dell, you know, is a great example. I didn't understand the technology, but I realized that, okay, I could close, right, and I could close fairly quickly. So I had to start learning things and get uncomfortable to get better, right? You know, and even at Gartner, you know, it was more of like, okay, again, I had to get uncomfortable to then not push so hard, build better rapport. And so I've— as I've evolved my career into what it is now, you know, you gain other skills, right? And you have to be open to realizing, hey, I'm not good at this, or I'm not good at that. Now, as I sit here today, I do feel like, you know, it's not arrogance, but it is an element of confidence that I do check all of those boxes, which is why I'm at the top every year. So, you know, I help with interviewing. There's other reps that say, hey, I'm gonna come to ConnectWise, I'm gonna be number 1. And I ask them why. Oh, I work so hard, Paul. I work so hard. I'm like, that, okay, so do I. How else are you gonna beat me? Right? Like, you can't just work hard and beat me because I also work really hard, right? You need to be— you need a better sales process. You get to be more knowledgeable. You get to be better at upselling, right? Like, there's so many other components that go into it than just, I'm gonna work hard, you know? And so, you know, well, that's a given, right? I assume you're gonna work hard. Yeah.
If you, if you want a hard worker, go down to the local restaurant or retail store. You know, they work on Christmas Eve.
Right. Yeah.
Work until 10, 11 o'clock at night.
Absolutely. Absolutely. You know, it only gets you so far in sales, you know? Right.
Because you very rarely see the grinder as number one. The grinder being the, you know, the 18-hour-a-day person.
Yeah, exactly. Well, and that, that's actually a great point because I was the 18-hour guy at Dell. I truly was. I was— they called it bell to bell. I was the first one in, last one to leave. Do I do that at ConnectWise? No, I work hard, but I work really, really smart because I don't have to be the first guy in and the last one out because I'm just really good at my job. I have a much higher close rate. I do a great discovery. I do all those other components that I don't have to be the grinder. I still grind, you know, because sales in general is a grind, but I'm not getting up at 7 AM and I'm not working till, you know, 10 PM and whatever like I did at Dell, you know, early in my career. So if you're early in your career, you want to be that grinder. You know, to learn, right, to absorb. But as you, as you grow in your career, that starts to slow down a little bit because now you've adopted these other skills. So you don't have to, you know, be that bell-to-bell sales rep.
Let's dig into the work smarter. What do you think you do smarter than your competitors?
I think I do a good job of anticipation. So it's kind of like a a thing that I have where, um, you know, even in terms of this conversation here or calls that I have, I rehearse in my head a million times and every single question they're going to ask. And so I already know how I'm going to answer that. I already know, you know, my story. And my wife, it drives her nuts because she listens to my calls. She said, you say the same thing every time. I'm like, well, it works, you know, until it doesn't work, you know. And so she's like, I can't listen to your calls anymore. You know, it drives me crazy. But If you don't— if someone, if someone asks you a question, you're a sales rep and you don't have an answer, you haven't done, you haven't done your job yet, right? Because they're gonna ask the same things that everyone else asked, right? I read this on Reddit, right? You should know all the weaknesses of your company. You should know how to address that in a way where they go, okay, I didn't think about that way. Okay, let's move on, you know, type of thing. So I'm just super, super prepared. I know my stuff. And hopefully, as you can tell here, You know, I am, I am confident. I'll tell people, hey, listen, you know, if you partner with me, you partner with my company, it'll be the single best decision you make for your business, you know, hands down. And I'm not saying that to win a deal. I'm saying that because that's what people tell me, right? And I've been doing this for 13 years and that's what I've been hearing. And I can introduce you to hundreds of people lining up that would tell you the same thing. And then—
Have you ever been burnt out?
Yes. Yeah, of course.
Well, let's talk about how'd you get out of it?
Because, you know, there's not an easy way. I don't think a vacation, you know, cures a burnout, to be honest with you. You know, for me, it's getting back in the swing and all of a sudden it's that next deal that all of a sudden gets me excited, right? Or that next deal, what actually gets me the most— this is weird, but when I'm talking to a prospect and he goes, I'm highly leaning towards a competitor, My competitive juices go crazy at that point, and I'm just like, nope, I'm winning this one. No. And so I go in hyperdrive at that point, and and that's usually how I've gone through it. I I love what I do. I couldn't imagine doing anything else. I'm very passionate about it, and so it's really just getting into that next sale that gets me re-excited again, re-engaged. You know, but of course, I mean sales, and actually going back to my first ever job, which was financial services, one of the guys there said. every quarter you take a week off, right? I've never done that in my career, but that's what he recommended, you know, because you get that burnout and then you take a week off. I've kind of found when I've taken vacation, it's never enough time and it doesn't cure, you know, burnout. But that's just naturally in sales and what we do. It's just, you know.
But do you have a way of decompressing? Exercise, whatever? Do you still play basketball?
Nope, nope. Haven't played in a long time. I mean, I do work out, you know, other things. I invest in the stock market. I travel with my wife, you know, so we love to do stuff like that, you know. So there's other things. I'm, you know, big family person. I went remote before remote was a thing. I went remote in 2015 more because it was, you know, something my wife and I wanted to do. We actually went traveling, you know, through the country with our son when he was in middle school. And we went up the East Coast and the West Coast and, you know, I continued to crush my quota doing it and it didn't make a difference, but it was an opportunity to spend time, you know, because now he's in college, right? So I look back at that time and how valuable that was, you know. And so I didn't want to be through my career and say, hey, I missed all that stuff for my son. I think that's the other thing I love about sales is it gives you that opportunity, right? You know, where, hey, you can make as much as you want, you can achieve those goals, But then you can also spend that time with your family. And I, I certainly made sure to do that, you know, and I look back with no regrets, you know, now that my son's in college and saying I spent so much time with him. I didn't miss any games, you know, that he had. And I was always there for him. And, you know, we did, we did some amazing stuff. So.
And, you know, pre-COVID, was it on-prem where you would visit customers or was it always remote?
So it was majority remote, but because of some of the territories I had. Like when I mentioned before, I had Florida. I actually lived in Florida. So yeah, I would go on site. It wasn't a requirement, you know, to go on site, but—
Helpful.
You know, it tremendously helps because, you know, when I'm sitting there with a prospect and then building that rapport, you know, that lasts for years, right? Like I have a— we call them partner, but we'll just say customer that I sold to like a decade ago. And we still chat all the time and I see him at events and things like that. And, you know, I love kind of sharing his story when people were like, I can't sign because of X. This gentleman, he signed it. He was at the Rose Bowl on New Year's Eve. You know, I was trying to get an end-of-year deal in. It was a really big deal. And he was drinking and we're texting back and forth. And he literally signed the contract. It was like 11:55 as he's watching his Michigan Wolverines in the Rose Bowl. And so if he ever listens, he'll know who he is. But that— I share that story with a prospect or with salespeople that I work with where, you know, if someone's like, I'm on vacation, I can't sign. What do you mean you can't sign? How can you not sign? I had someone sign at a Rose Bowl. Like, that's no longer with technology an excuse of why I can't sign, right? Like, I have to be at home in front of my computer. Like, no, with DocuSign and other things like that, you just— here's a phone, here's an iPad, there's, you know. And so, you know, I, I don't, I don't, you know, I, I don't kind of let those excuses, you know, kind of Oh, okay. Hey, no problem. Back in 2 weeks. See you next year. See you next year. Hey, no.
And there's a lot of talk today about detaching, which is kind of, yeah, in certain senses it makes sense. Like you're prospecting, you can't be hypercompetitive in prospecting because you have no idea where they are and their timing and their need. How do you regulate that competitiveness?
You know, I would say, you know, and I see online a lot around AI and it's going to replace BDRs and things like that. I don't see that ever happening because there is an element of, you know, when you're talking to someone is, you know, again, building that relationship. And sometimes— so I started in financial services, which was all about cold calling. It was all about numbers. It was a numbers game, right? And so, you know, and Brian, you probably know as well, like most sales reps when they're prospecting, they give up the first time or the second time or the fifth time or whatever. But the reality is it's gotta be like that 10th time or 15th time, you know? And so as you're calling and you're getting no every single time, you're gaining information on that prospect, hopefully, right? You're asking a question as they're hanging up on you, or you're gaining something from the gatekeeper that the next time that you call, that now you're armed with more information.
Mm-hmm.
And now you can have more value. So I've trained, I don't even know how many BDRs in my, my career, giving them talk track, things like that. And we powwow all the time on what are they hearing. And then I give them, you know, things that they can go back to for the next time, or even that guy, right? Because they didn't think of it there. They're nervous, right? They're on the phone with a prospect, but you know, you still gotta be aggressive. I mean, prospecting, sales, You've got to, but you got to read the room, right? Like, that's a big one is being able to read the room. Is it, is it over the line, right, with, with your prospect or someone you're, you're cold calling? Because here's the thing, I, I remember plenty of times that I've made a cold call and I've called the guy back 3 months. He doesn't remember me because they get so many.
Yeah.
So I learned that early in my career. So it's like, if someone gets annoyed or hangs up, okay, you're on my list to call back in a couple more months. No big deal. You know, but you want to gain some information. So when you're calling back the next time, it's like, oh, this guy kind of knows what's going on over here. And he's not going to remember that Paul or James or whomever called him, you know, 6 months ago type of thing. But I do think there is an element of you got to push at least 3 times, try to overcome at least 3 objections. And again, this comes back to preparation with anything that you do in sales is, you know, what the objections are going to be. I'm not in the market. I mean, I'm not interested. I'm all set. I'm happy with what I have today. Right? Like, if you know all of those already and you have your script written next to you of what you're going to say, you know, and you just rattle it off and you're ready to go, you know, and then they're never going to say anything. You go, oh, I've never, never heard that before. No one's ever said that to me. You're not interested? Everyone's interested. What do you mean?
Crazy. One final question. Who's going to be number 1 at ConnectWise this year?
That's a tough one. Me? No. Yeah, of course. Me. Absolutely.
Thanks, Paul. I really enjoyed talking to you today. Where can people go to connect and follow you?
Um, you know what, I'm not a big social media person, but I am on LinkedIn. And that is— at this point, that's about it. But maybe if this goes viral, and maybe I do a little bit more out there. And I'm not a big social media person. I'm a little old school in that fashion, Brian. But, you know, I'm— I wanted to chat with you again. I'm a big fan. I love your content. And then maybe this is a platform for me kind of moving forward. I don't know. We'll see. So hit me up on LinkedIn.
Now, why is mindset so important? Because everything is dependent on it. And it's the one thing that we have total control over. What we think, how we react, our attitude, our perspective, it's all in our head. And although things may trigger us, we may have gut reactions, and we may say, I, I can't be positive in this environment. Well, is that the environment or is that you? Granted, the environment may be terrible. And in sales, this is a huge challenge. I faced it my whole career. You know, you started a company, you never get the great territory, you usually get the leftovers, and it's up to you to prove yourself and make something out of it. Now, a lot of people just jump from job to job trying to find the perfect situation, and I get it. Everything looks better out there than when you're currently in, and if you've got a Comp plan that's not very generous, or you got a manager who isn't very supportive, or even a tyrant, then, you know, it might make sense to leave. But ask yourself, is it really the territory? Is the new territory going to be better? Uh, it can't be. Life is not fair. It just isn't. And trying to find a new situation that is more fair There's one way to approach it. Another way to approach it is, hey, I can survive anywhere. And think about it. Now, you got to imagine, and I don't know about Paul's manager or owners of the company, but guess what their perspective on him must be going from this territory to that territory to every territory you can imagine. And somehow he still pops up to number 1. Okay, what is that? Is he Superman? No, you heard him. He's a mere mortal, flesh and bone. Uh, you know, nice guy, hard worker, skilled salesperson. Sound like you, doesn't it?
Hmm.
Now, does mindset alone do it? No, you can be a real hard worker. I worked with a guy who my manager told me, oh, he's a— I forgot, what did he call him? He's a bulldog. He just crashes through doors. Brian, look out. And I'm like, okay. And that's what my boss liked. He liked the impression of the salesperson, not the capability of the salesperson. And that guy came in and in one year, He did like one, you know, add-on deal that was pretty much order-taking at an account that I had closed a year before. And everything else was maintenance renewals, which order-taking again, existing customers have to buy it, no choice. No new customers, big pipeline.
Pipe fiction.
And he ended up leaving after that year. And I kind of anticipated it because what we were selling was very complex and selling it in a very competitive space. So getting the meeting was part of it, but not the whole thing. He didn't know how to close a complex sale. He was a transaction person and a grinder, but no talent. Now, if he had the talent, but he didn't see it as a talent obstacle. He saw it as a grinding obstacle. And let's face it, you have to grind in sales to a certain extent. But look around in your company. Is it the grinder that's at the top, or is it the person who's selling the smartest? Somebody who found a smarter way of closing big deals. And you can give it to the territory and as the manager's friend and everything, but then pick the other person, number 2, or the person in Montana or North Dakota or whatever territory in your country is barren of any prospects. Yet, they still did pretty good.
Then what?
I think we each have to own it. And I think here's my secret to not falling into the B-player trap. And this gets us all because you have to have this emotional regulation in sales. Because there's all this talk about detachment out on LinkedIn right now. And in certain cases, that is 100% correct. But in sales, When we're in front of the client, when we're giving a presentation, doing a call, negotiate, any customer interaction live, we have to be confident. We have to be centered, be present. Now, when we're not in front of the client, how should we look at a deal? The same way? That same level of confidence? Everyone does. And that's the mistake. That's the trap. Because they're not looking at their deals with fresh eyes, with a little bit of insecurity, a little bit of paranoia, a little bit of what's my competition doing? Who inside that company doesn't want this deal to happen? Who's it going to hurt? Has the CEO even heard about this problem? Not the product, not the change, but the problem. Do they have any awareness of that? See, you're not going to ask yourself those questions if you're comfortable with the deal. And here's another secret: our brains are pain avoidance machines, meaning that our brains will not show us things, not give us signals about things that are going to cause us pain. Why would it? Our brain is trying to keep us safe all the time. Survival is number one primal need. And that's what our subconscious is focused on. Thinking about what could go wrong with our deal is like number 35 on our brain's list. And it doesn't remind us of this. And if you've ever tried to change a bad habit or create a new one, try it for the first day or 2. If you don't have a lot of reminders and reasons and Post-its and alarms, you'll forget about it. You need that initial trigger to remind you because our brain doesn't want to think about it. I've got a morning routine and I try and add something to it every 2 weeks. Small, tiny little change. And if I don't have some kind of reminder blatant in front of me, can't miss, and move it every day so that it's a little different every day, I find out, oh, I go to bed that night and I go, oh, I forgot about this. And even sometimes, even if you have the checklist, you'll forget about it. Now, did my conscious mind forget about it?
Yeah.
Pretty much knew I should do that. I wanted to do that. I know I want the benefit of it, but my subconscious is saying, ah, you're fine. Don't worry about it. Last thing we need to do is more work. And it very quickly moves on to something it wants— food, rest, distraction, all of those things that give you comfort. Now, don't fall into this B-player trap. So if you're early in sales, yes, in front of the client, you need to be confident, Not cocky, confident, reassured, positive. But after you're in front of the client, you need to really scrutinize what was said, how you did it, how you think this deal is going to pan out in the future, and what are the traps that are naturally going to surface. Because the complex sale, like life, is just one trap right after another. And if it looks easy, it's probably a trap. Send me a proposal. One big trap. Give me a discount and I'll get it done. Huge trap. Oh, it's going to go right through. Don't worry, they do whatever I say. One big trap. And if you don't know how to avoid these, it's near impossible not to just fall into them. Why does everybody sound like a sales rep? I don't know. Because it's a trap. We think we should, so we do. Everyone else does, so we should sound like them. The complex sale is just probably 5 traps in a row. And if you don't avoid them— and when I say trap, I mean, once you're in it, you can chew your leg off, yes, but then you'd only have one leg. Getting out of it is not easy. Everyone thinks it's easy to get out of a trap. There must be a tip or a trick to do that. You know, yeah, some people sometimes under certain conditions maybe. But if you're not in the trap, you can focus on closing the deal. Closing the complex sale is hard. Go on this hero's journey with me. Imagine a year from now. Knowing this capability, understanding a deal, understanding and having your process, not mine, yours. I map it out for you, but you need to customize it to your style, your market, your customers, your timing, your style. And once you do that, then you have a system. And guess what? Mine is still written down. Is it because I'm stupid? Partly, but it's more because you can't memorize it and your brain is not helping you. Your brain just wants you to be safe. That's it. It, it can't comprehend— your subconscious can't comprehend money. It comprehends survival today, right now, not tomorrow, not 2 hours from now. Right now. So you have to be able to understand the game you're playing, or that trap will be so enticing. Because I hear it all the time, every office hours, every one-on-one, the same exact traps. They won't call me back. They said it was going to be easy. Now they don't want to do it, or it starts over, or They want a 50% discount or 90% discount. Learning how to close the complex sale is game-changing. And ask yourself, I know all kinds of rationalization and excuses are going through your head, but it's costing you, I'd say, 30 to at least 100 to 200% Of your income. Let's say you're making $200K. It's costing you a minimum of $40K a year not to know this, not to have a system. Might be $100K, might be $200K. How many years, months, decades are you going to go through missing that opportunity? And I'm talking about selling smarter. None of this is about grinding. There's not one thing in the course about numbers game, more activity, none of it. Less activity, less deals, bigger commission checks. Because I think people today are, you know, looking at their 100 deals and they know 3 to 5 are going to close that quarter. A lot of time is wasted on those other 97 now, isn't there? You want to work the other 97? That's up to you. But are you really working it? Are you servicing it? And who's doing the real selling with your client? Are you counting on your champion to do the selling? Hmm. They're overconfident. They don't have any context with the decision maker, economic. Oh yeah, scary, isn't it? Sign up today. Let's go on this journey. Let's Take that income, let's get it up to 100%, 200%. That's where the fun is. We'll see you next time.
