Paul M. Caffrey: Unpacking Elite Sales Habits for Superior Performance

Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now, today's guest is Paul Caffrey. He's the leading author of the book, The Work Before the Work, which explores the hidden habits that elite sales professionals use to outperform the competition. Paul's also a keynote speaker and works with early stage founders, helping them build sales processes to hit their first 1 million in ARR. Now, Paul and I go back a little ways. He actually was one of the reps in a class that I was teaching at Salesforce a while back.

So I always love it when things come back around and the student becomes a teacher now. So Paul wrote this book, The Work Before the Work, and we dove into it. And what I really loved about this, first of all, this whole conversation, sales, sales, sales. So if you're ready for that, let's go. But this was a lot about some of the stuff that the top reps do that everybody else doesn't. But it's not like a secret, right? I mean, these are very obvious things to do. It's just most people don't do them. And so we talked about some of these non-negotiable habits that the top reps have. We talked about six hidden habits that most people don't see. And then we got into stuff like longevity in the career.

I mean, it's funny. I get a lot of reps asking me right now, John, I'm feeling burnt out, right? I've been in sales for three, four, five years, and I'm feeling burnt out. You've been doing it for 28 years, man. How are you not burnt out? So we dove into that. And then we talked about how success leaves clues and how we're getting, we have to get back to some of these fundamentals or else we're going to lose ourselves here. And really dove into, again, exactly what the best reps do. So if you're looking for a sales conversation, you found it. Hope you enjoy the conversation as much as I did. Let's make it happen. Paul Caffrey, how are you? Welcome to the Make It Happen Monday podcast, my friend.

How are you doing today? I'm really good, John. Delighted to be here. Thanks for having me. Yeah, it's good to see you again, man. It's been a while. I think the last time we talked was when you were releasing the book, which was probably what, five, six years ago, something like that? No, it's only a couple of years ago. So as we met up, five, six years ago, I would have met. I'm in a time warp with COVID, so I have no idea what time it is. Two years or 10 years. I don't know. Yeah, yeah. No, time is going so fast at the moment. So it feels like with all the change we've seen over the last year or two, that's for sure. Yeah. And you know, now that you have, you said you have a couple of kids now, right?

Yeah. How old are they again? Two and three. So two little girls. Best thing in the world. Yeah, that's great. I love girls. I love being a girl dad. But one of the things that struck me when I had my daughter was like, you now watch time. So that's what freaked me out. Like before I had my daughter, I didn't really have any true concept of time. I just kind of kept going and all right. Yeah, I guess it was a couple of years ago, whatever. And then when I had my daughter, like you literally watch time happen. Because when I was traveling, we were talking about this before we got on, you know, I'd leave for a week at a certain stage or life or whatever. And when I would come back, she would almost look like it, like be a totally, it felt like she was a different person because she might have grown an inch or she, you know, was doing something different that I hadn't seen before.

I was like, holy shit. Like that really sad. Have you started to notice that you can notice time a lot more effectively now with kids? Yeah. And you just notice how fast it's going. I even, I dropped them off at a crash this morning. My wife turned around and said to me, ah, our oldest is going to be four in October. I'm like, oh, oh yeah. Wow. That's quick. She's not a baby anymore. But even like, like we were, we happened to be away for a few months and just coming back, you could just see, yeah, the growth is there. We talk a little bit more. They're joking a bit more. Like it is great. The wishing for the end of quarter, that's kind of the perspective shifts a bit, right? I don't want those quarters to go quite as fast anymore.

Yeah, exactly. Exactly. Awesome, Paul. We're going to get into a bunch of stuff about, so there's going to be a full-blown sales conversation today, but let's do the, let's do the background story here. And, you know, you can kind of connect along the way of how we connected. But, you know, let's start with your origin. Like where'd you grow up? Parents, how'd you kind of get that entrepreneurial itch? And then how'd you evolve towards where you are now, writing the book and doing some consulting? So I'll give the audience a little bit of context here and then we'll dive into it. Yeah, we'll do. So I grew up in Ireland, in Dublin. So some people might be familiar with it. Some may have been lucky enough to visit at some point.

It's a great place to visit, man. Yeah, it's fun. You know, it is a fun spot. As a Bostonian, it's near and dear to my heart. Because I had like, actually, when the first time I went to Dublin, quick story, I, the Philip Cleary, a good friend of mine, brought me around to all the pubs, right? Oh, excellent. And I had this big shit-eating grin on my face. And he's like, what's so funny? I go, that pub's in Boston. That pub's in Boston. That pub's in Boston. And I don't mean just the name. I mean the name, the decor, Sully around the corner who's sitting on the side, like, you know, Patti over there who's drinking, you know, Guinness. Like, it literally, it's almost like the Irish came over here and were like, yeah, we're just going to replicate what's going on here in Boston.

Yeah. It's, yeah, it's so cool. And you see that all over. And one thing I can't get over anytime I go to other cities is that, you know, there are days of the week when it is good to go out. Whereas Dublin, it's Annie Day. So I was like, oh, what, it's quiet, like, why is there nobody out on a Monday? And now you're like, oh, okay, Mondays you're not supposed to be out. Right, I got it. So growing up in that culture was great crack. As if you spoke to me as a teenager, I was like, yeah, I'm going to be a professional footballer. I'm going to play soccer in England. I was on that track. So very competitive, very focused on that. And then it'd be like, oh, well, if that doesn't work out, what's going to happen?

And I was like, no, it's okay. I'm going to work in research science. I'm going to cure some disease that nobody's cured before. So long story short, football career didn't pan out. Injuries probably just wasn't good enough, but injuries definitely prevented me from being able to continue. And then I decided, right, I went into science. So my father was a scientist and it was a kind of natural thing that was always around conversations, the dinner table or whatever. That was fantastic. Four years got qualified. And just as I qualified, it turned out that research science was, I guess the options had changed. So instead of actually being paid to do four or five years of research and the way it works, you research something, you discover something amazing.

Your career is made. You don't. That's okay. You go on an industry. So it's still a good thing, but you are paid for that work. It then became free work because the economy collapsed 2008. So I was like, no, come on in and work for free in your 20s. So for me, I was like, oh, it doesn't sound like too much of a good deal. I'm not sure about it. And so I left Ireland, went to London and just looking around and decided, okay, let's try sales. I really liked the idea of it. And there was a company, Sun Microsystems, I guess they were acquired by Oracle at that point. I went in and I suppose cut my teeth there, spent a couple of years of that. And then I realized it's cloud computing thing. Only 1% of companies are using it.

This is going to be pretty big. And so then fortunately got the opportunity to move back to Ireland and was involved in the Microsoft launch of 365, which was Microsoft's cloud services that nobody heard of or trusted or wanted back then. So that was a fun time. So nobody wanted to buy anything. And then they really didn't want to buy new technology. So that was a tough period, but really helped me learn what it needed to be successful in sales. And then got the opportunity to actually work, do that in the Irish market. It was then launched with a telco in the UK. So I went over to the UK and was over there for four or five years again. So kind of back and forth. At that point helping, this telco went from zero to 100,000 users of the subscription over a four or five year window.

And I played a pretty big role in that, which was really great. I still speak to a lot of people today. During that time, I was always thinking about the future and what I'd like to do in the future. So running companies, leading companies was always on my mind. So I went, got a master's in business, really fortunate, got to meet some of the leadership team who were studying on it at Salesforce. And this was 2010 to 2012. And I was over in the UK and like every year they're like, we're going to grow 30% this year. Yeah. Come over here. You know, forget about that Microsoft stuff. It's boring. I was like, no, no, it's okay. 30%, you keep that going. And again and again. And every year Salesforce kept making it happen.

I was looking, I'm going, whoa, okay. So then I decided, let's give it a go. I went over, you know, was in Salesforce for a good number of years. That's where I met yourself. John, I remember I was 10 years into my career. I was like, okay, you've got sales training today. I was like, you know, you're going, I like to learn, but like, I want to do training. I want to have this meeting and I got to enjoy your, it was fill the funnel and drive it close. I think you were doing the two at the same day. I think it was like a morning and afternoon sort of thing. Really, really great. So actually anybody who wants to get their sales teams trained, that is definitely something to check out. And that still stuck with me even to this day.

I was really, really enjoying it. But from there, had the successful time in Salesforce, but I was at the stage where I'd always wanted to drive high performance. So in 2013, 2014, I was lucky enough to come across a guy called Todd Herman. He coached the Olympic team, Fortune 500 companies, even, you know, Real Madrid to achieve high performance. It was his first foray online. So I got the opportunity to join an early cohort at a price which would be way cheaper than what it probably is today. And that made me realize that if I took a step back and thought, what is it that is making people perform at an elite level? It's that they're actually ready. It's that they're prepared. It's that they don't leave anything to chance and they don't rely on hope.

And I remember at Salesforce seeing, you know, tenured reps who were, you know, like they were excellent at selling. They had a great product, did a great supporting team. And you're looking at it going, that meeting, you know, that demo, that solution presentation, that onside meeting, that's a slam dunk. You can see these guys, they're really going to go ahead with it, but they would still practice the demo, the dry run, two, three, four, five times. There'd be solution engineers and they'd be driven, demented, going, we've been through this already. He knows, we nearly know exactly what we're going to say. And it was true knowing exactly what we're going to say and knowing those moments where things could go a little bit awry, that the best kept going.

But then I realized when you ask the best, what do you do? They could not tell you. So you go to the top reps, what are you doing? That's so good. It's like, well, I'm doing my job. Like, you know, I sell. I got to see how I hit my target. But what are you doing? And that's when I realized, oh, okay, there is something here which needs to be broken down and needs to be shared. And that was really the emphasis for me to go, you know what? I want to try, get that out there. And I want to try to help more people achieve their potential because fairness is an inherent core value for me. And I thought it was so unfair that you had these people who wants to be successful, these people who were successful, but then we couldn't actually communicate what was working and what wasn't.

And so then people were left struggling. People were doing really, really well. And that's what really got me into this space. I love that, man. And so I think that, you know, that the book, the work before the work, right? That's the title. Yeah. So we're going to dive into some of those principles. I want to go back though to something you said, you know, you were sitting there and you saw this cloud computing thing, right? And it was 1% and you figured like, hey, there's something going on there. And so how do you look at opportunities? And let me give a little bit of context on this. I've always said that for me, one of my, I don't want to say superpowers, but one of my gifts is I usually am able to look at a situation without much data and be able to put one or two pieces together and say, you know what?

But that makes sense and not overanalyze it and just say, fuck it. I'm doing it. Right. Because, all right, let's go. Whereas other people overanalyze the hell out of everything. And look, don't get me wrong. I have made some massive mistakes, especially recently, quite frankly, and spent a ton of money, wasted a ton of money because I didn't look through the details. But that's just not my style. Like I'd rather just go waste the money and then go try to make more money to make up for that type of scenario. How do you look at opportunities? Are you more calculated or are you more gut instinct? Because this is going to translate to the conversation of science over art. You just mentioned what the art, like what those best sales reps are, like they're artists in a lot of ways.

They don't know how to tell you what they're doing because it's just come so natural for them, but there is a science to it. So I'm curious in your personal decision-making approach, are you more art or science and how do you look at things? So for me, I guess I would say a little bit of a blend and that's not to sit on the fence, but you don't need to drill into a huge amount of data to see if something is going to take off or not. So I guess, you know, what do I mean by that? And I remember running a side hustle, when was it? Maybe 2011, 2012. So there was this thing called fantasy football where you get points if people actually, you know, score goals or do well in the games that are on the weekend in the English soccer and others, American fantasy football now as well.

It's very successful. But I remember just looking at that and going, okay, hang on a second. There was a million players last year. There's 1.2 million this year. Okay, there's going to be 1.4 million projected. I'm like, okay, that's just growing. And that's something that I'd love to get involved in football again. So at that point, I could say, okay, that's an opportunity where something is getting bigger. So jump on it. So I did set up a podcast and we worked on national radio, writing for a national newspaper. And, you know, all of a sudden your side hustle becomes another business and that's fantastic and it was great. But it comes down to just being able to look at something and try to extrapolate what you think is going to happen.

And then using technology a little bit to your advantage. You don't have to be like an expert, but you have to understand, well, what tech could you use that would actually help you versus others? So back then, you know, SEO was a thing, but a lot of people didn't actually, you know, SEO optimize their website. So essentially my website, France Europe, I spent a bit of time optimizing it. And then the reach was getting 250,000 people a month on it. And again, you're looking at this going, not too much, but it's looking into that. So it's, for me, it's seeing a few data points and then it's going at it and seeing if it actually, you know, comes to fruition or if it doesn't. And John, yeah, I've had those things where I've put money into getting apps built and done a few things, didn't work out.

You know, that's just a lesson to learn and move on. Yeah. I mean, I think that's for me, one of my things is, you know, that I've learned in startups specifically is timing is everything, right? I mean, you could have the best idea on the planet, but if the market's not ready for it, then it doesn't matter. And so, you know, and I actually, my thing is, I think I look a little bit too far out to say, this is absolutely long-term going to be massively successful. But when then it fails in the short term, like shit, like Bitcoin or NFTs or those type of things. Like I fundamentally believe that Bitcoin eventually will be the currency of the world, right? Well, Bitcoin, whatever, crypto. But the market's just not ready for it.

I mean, obviously it's a huge comeback recently, but I think until it's regulated, until somebody's there saying, hey, when you lose your money, you can call somebody and say, where's my money? Go get it back type of thing. Until that happens, I don't think it's going to get mass adoption. So it was like, that's why I'm psyched. I left my Bitcoin in there because I was like, oh man, I took a dive on this shit. And then all of a sudden I'm like, yeah, back in business. So I think it's one of those like short-term, long-term and that's why, have you ever read Simon Sinek's book, Infinite Game? No, I haven't actually. Yeah, man, I'd highly recommend putting that one on your list. Yeah, he's got his why, you know, which is what it put him on the map.

But his book, Infinite Game to me is a brilliant one because it talks about, there's two types of games. There's the finite game and the infinite game. The finite game is there's a winner and a loser. It's like a football match, right? There's two teams, there's a winner and a loser. I'm trying to beat you. Whereas the infinite game is I'm just trying to stay in the game. And that's kind of where I think I want to transition our conversation to, you know, sales reps and the ones who stay in the game. Because there's something different about the ones and it's consistency, it's showing up every day, it's doing the right things. And I want to peel back on that because, you know, when we were prepping for this, before we jumped on here, I told you, I've been doing a lot of sales kickoffs recently.

And, you know, I usually get the questions about this, whatever, but there was more than a few that came up recently that were just like, man, how do you still do it? Like you've been in sales, like in the, forget about like what I did before school, but you've been in the profession of sales for 28 years and I still sell every day. I still prospect every day. I still negotiate all my own contracts. I still work with my clients. And I still do the work and people are like, dude, dude, like how the, like I'm 25 years old and I'm feeling like I'm 80 at this point and I'm burnt the fuck out from this profession. How do you stay with it? So let's talk about some of the characteristics that you see in some of the best reps that you work with and peel back some of these layers here.

Cause you have like six hidden habits. You got some non-negotiable habits here too. What do you see in not just great sales reps, but long-term great sales reps to stay in this profession and what do you think it takes to, to, to stay here as opposed to like coming in and out, you know, and, and, and after, you know, flashing the pants and then be like, all right, I got to go to marketing or I got to go do something else here because it's way too stressful. Like what are some of those key ones that you're looking at right now? Well, I guess what it comes down to is if you want to achieve longevity, you're, you're looking at doing something that's sustainable and like the burnout is, is a real interesting thing because it is a real thing, but it's also something that people can hide behind.

Look, I've been there where, you know, you're going to the airport at four o'clock in the morning, half six, jumping in a rental car, going, doing a series of meetings. And then at 12 o'clock that night, sitting in the bar and actually doing quotes on the laptop and then getting ready to go again, you know, get up with say five the next day. And I guess the difference is at that point, yeah, things were going really, really well, but at the same time, it comes down to, I think for me is people, they sometimes will work really, really hard and do a huge amount of work, but they're being lazy in that. And what I mean by that is they're not looking to qualify stuff. They're not looking to make sure that they're using their time effectively.

They're just speaking to anybody and everybody who they can speak with, particularly today when, you know, pipelines are a bit thin and it is more comfortable to have a bigger pipeline. But, you know, you know, if you're listening to this, that there's probably a few deals that shouldn't be in your pipeline. And what I think the people who go on and achieve that longevity, they're really able to understand, right, well, what should I be working? What shouldn't I be working? And they then make space to actually get rid of the junk so that they can find more better deals to go for. And that can be pain in the short term, but long term works out a lot better for you as opposed to the opposite, which is where you're working loads of deals, half the mark qualified, shouldn't be there.

At the end of the month, end of quarter, you're really stressed. And then the number just turns out to be okay, where sometimes it can still be bad because you've worked bad stuff and you're into that cycle. So it really means taking a step back and go, are you doing this right? Are you doing this well? It's a little bit like golfers. A lot of golfers will actually get to the top of the game. I remember Corey Harrington doing this. He got to the top of the game, won a couple of majors. And then all of a sudden he changes the swing. And the reason he changes the swing is because the way he was playing, he couldn't continue with that. So he needed to get something which meant that he could actually go longer.

And I think salespeople, we kind of need to do that as well and to make sure that we're not just being lazy by working really, really hard. That's interesting, right? Because I think there's the, I mean, that's the old work smart, not hard, right? Type of thing. And I, and I think that, that a lot of people, especially right now have taken that to the extreme in these hacks, you know, and I think one of the things I love about your book is that there is no silver bullet. There is no hack to success. Um, but I think everybody's trying to work so smart so they don't have to work hard. And I'm personally calling bullshit on that because you have to do both. Like you have to work your ass off and you have to work smart, right?

There is something about genuine, like just activity. And I, and I like the way you put it as far as you're being lazy by working hard. So I never actually thought of it that way. Cause I, cause you're, you're keeping busy by feeling like you're doing a lot of things. And I definitely feel like I do that quite a bit, you know, I, cause I'm a, I'm a task management animal, you know, I'm a zero inbox guy. So I get satisfaction personally by checking off things on my list, right? Like I get anxiety when I look at my inbox, I was up until two o'clock in the morning last night because my, I needed to get my inbox done. I need to get my activities. I don't like seeing those overdue activities, but it is quite frankly, a lot of busy, like busy work.

And I do, I've gotten better at kind of looking at like, do I really need to follow up with this client that I followed up with four times at this point over the course of the three years. But then in the back of my head, I'm like, yeah, but every, you know, because I do that and I'm staying top of mind, eventually I get those people to call me back. Right. So there's an inbound component to this. So I'm always balancing this time management of busy versus reality. And for you, I guess, especially when things are, are like almost like panic zone, you said pipelines are pretty light right now. And that's the fact, like what happened in the early last year, especially in the tech space, things fell apart.

Doubt money isn't free anymore. It's not a grow at all cost environment. There's real ROI. Clients are scared to make decisions because there's too many options here. So, you know, my thing is yes, smart, but if you are not hammering it right now to try to just get as many conversations going so you can at least understand what's happening in the marketplace, because there's one thing about finding the sale. There's other thing about finding the gaps of what's actually happening in the marketplace. And I genuinely believe you have to have as many conversations as you can with as many people when times are tough to just do some market intelligence, if nothing else. So how do you balance that quality quantity approach when you're like at, well, how do you see top performers balancing that quality quantity approach?

Yeah. And it's, you know, it comes into something actually, I'm a co-author, Phil M. Jones. And, you know, he's exactly what to say. And one of the things he says is that, you know, success leaves clues. And what it comes down to is, you know, you can, you know, pull in your list from Zoom Info Sales, whatever it is, and then just start hammering it. And yeah, you'll, you know, your metrics will be good if you're still being driven to, you know, send so many emails, make so many calls, whatever. You can hit those vanity metrics very, very easy. But if you take a step back, what the best they're doing is they really ask themselves, well, what am I looking to achieve and how am I going to achieve that, right?

And if I'm looking to have conversations, meaningful conversations with people that actually matter in businesses that I could potentially look to do business with, well, I need a good list. So that might mean that I spend a little bit more time getting that list together, but we're not talking like, you know, if it takes you 30 minutes or 45 minutes to pull your list together, maybe that stretches to an hour. You're putting a little bit more thought into it, but maybe you're saying, no, it's a little bit shorter, but then you're going to go after the people on that list with a little bit more intent and they're going to get more activity because, you know, these are the people I want to have the conversation with, as opposed to just any list, any junk.

And you're chatting to, you know, an admin and you're chatting to whoever, or you're chatting to CS, but you really sell to marketing. And again, I agree with you, John, you need to have those conversations. These understand, you know, is the status quo, is there, are you afraid of making the wrong decision? Is it actually that sales have fallen off a cliff for the business? Or, you know, is there, there can be so many reasons why people are doing that and looking to really understand where is their head at? And again, it's going to be different for different industries, but broadly speaking, we are in a bit of a shift now and people are, I guess, afraid of making the wrong decision. That's something I'm kind of saying.

Oh, that's absolute. You know? Yeah. Have you read, actually, people listening to the podcast would probably sick of me saying it, but have you read the book, Jolt Effect? I haven't. No, it's another one. Put it on your list. Put it on your list. It's the crew that wrote corporate executive, it's corporate executive board, the ones who wrote Challenger, Challenger Sale, Challenger Customer, and Jolt Effect. Jolt Effect's the third in the series. And that's exactly what it talks about. It talks about how we've crossed the chasm. Whereas before everybody expect, you know, thought that, you know, by the time somebody comes to us, they're already 60 to 70% through the sales process, whatever. Well, now the assumption there is, well, the client has all the information, right?

So we got to play catch up. But now it's actually crossed the chasm in the sense that now there's too much information. There's two, things are moving too fast. And so people are literally scared to make a decision because of the risk. And so our job is to de-risk the situation for them or make them realize that their current situation is actually more risky than making the switch to what we have here. And it's a really interesting, it talks about how everybody's like, no decision is our biggest competition. It's like, actually, no, it's indecision is our biggest competition. So it's a really interesting take on kind of open my eyes to say, because we're all taught to like paint the beautiful picture of what we can do for you, right?

Like, oh, look at once you implement this, your life is going to be perfect and all this other stuff. But nobody believes that anymore. So I'm actually talking, my questions revolve around, hey, like, what happens if you don't, if you make the wrong, like, not even what happens if you don't make a decision, right? And it's no decision. But what happens if you make the wrong decision here? Like, what happens if you go with the wrong vendor? What does that look like? And then it's like, oh, you start to hear people, man, if this, if I fuck this thing up, man, I'm screwed. And, you know, sailor paint funnel, third level here, like, oh, man, I'm going to get fired type of stuff. So it's a really interesting take that I think would be that I've started to apply quite a bit in the conversations.

Yeah, I mean, and that's it. And I think, like, we've, we're looking to evolve beyond just asking, you know, what's the negative impact? I'm not going ahead with this. I mean, yeah, okay. I mean, sort of still important, but it's getting to that real conversation. And it's making that real connection with someone. And one thing that I find, which actually helps you get to that level, and you can do this really at the start of conversations. I also think you do quite naturally, John, as well, is if you share something with the person that you meet that they don't expect you to know, you all of a sudden get them to lean in. And the conversation starts, as opposed to looking to us, let's just build rapport by chance.

You know, I'll mention, oh, did you see the game last night? And it turns out you don't like that sport. Great. We're off to the other way. And then the rest of the meeting can be exactly the same. But if you actually frame it that way, then you're in a position of getting people to lean. Actually, this person's done their homework. They've thought about the company, they've thought about this role, and they're bringing a perspective or a point of view. And if you're super young in sales, you know, lucky you, you know, it's great. Yeah, good for you. I'd trade places with you any time. Yeah, exactly. Yeah. But you can flip that around and do a little bit of an eight-mile M&M. Some people might not remember that movie, but essentially, it's like, well, you can call out that.

Look, I'm only a year in the industry, and, you know, what I'm seeing is this, and I think it means that. But you're obviously, you know, much more experienced. What's your take on this? And then just flipping around, and all of a sudden, you know, having some deference there, it just gets people to actually open up and have real conversations. And that, I think, is what we're kind of going back to. So we're kind of leading these templated questions and, you know, going through stuff. Because people have, they're hearing the same questions all the time, different variations. So it's basically, you know, an experienced executive. They know, oh, you're taking me through this. You're taking me through that.

Yeah, blah, blah, blah. But it's then into connecting. And that takes a little bit more preparation and understanding what you're looking to try to achieve out of those meetings. Yeah, I think that's, I actually, to your point, I really, I even start the car. I don't let the client guess whether I prepared or not. I'll straight up say, hey, Paul, you know, as I was preparing for our meeting today, I noticed on your website, I noticed you just posted something. I noticed whatever that is. Literally just doing that, you'd be amazed at how that wakes people up a little. Because to your point, they're so used to going through the drone, like, bant questions, dumbass shit, and then droning through a demo and whatever.

So if you just literally start with, hey, I was kind of curious, you know, like, as I was prepping for this, I noticed that it was really interesting. And how'd you get to wear this, you know, point in your career? Or what impact is that having on you? You see them sit down and be like, oh, damn, like, this is actually a conversation. This isn't an interrogation. And then a pitch, like, wow, all right, let's open to this. And it immediately loosens up the conversation. So you talk a lot about prep, right? And what the best reps do to prepare to win versus just kind of act in the moment. And I think a lot of this comes down to practice. You said earlier, you know, Tiger Woods is another perfect example of that.

Like, he rebuilt his swing probably 15 times in his career, right? Even when he was at the top of his game, literally when he was the number one golfer in the world, he went and redid his swing 100% and practice, practice, practice, practice. And there's this beautiful Michael Jordan video, who's my personal favorite basketball player. And he's like, you know, maybe I made it look too easy. Maybe it's my fault. He's like, maybe I made it look too easy on the court. Because, I mean, seeing Michael on the court, it was like a ballet, man. It was like, oh, my God. Like, look at what. He's different. But the amount of work he put in to get there behind the scenes. Same thing with Kobe Bryant. Like, there's a great story I read recently.

Alan Iverson, who, when he was 19 years old, went to L.A. And Kobe picked him up. And Kobe was 18. And he had just gotten into the NBA, right? And rookie Kobe. And Friday night in L.A. And Alan Iverson's like, yo, where do you want to go? You want to hit the clubs? Like, let's go to the clubs and have some fun. And he's like, no. And Kobe was like, all right, which club do you want to go to? I was like, oh, just tell me, right? He's like, cool. And he's like, I'll drop you off. And AI's like, wait, what? Like, aren't you coming out, man? He's like, it's Friday night, man. Let's go get it. And Kobe's like, no, man. I go back to the gym. And AI was like, what, what? Like, it's 10 o'clock at night on a Friday in L.A.

And you're an 18-year-old millionaire. And you ain't going to go out balling at the clubs? And nope, man. I'm going to the gym. And then he'd be up at 3 o'clock in the morning at the gym, like beating everybody there. So what's the right preparation, I guess? What's the right practice? Because going back to busy versus quality, right? We can all practice bad free throws, but that's not going to make us much better if we don't have the right technique. So what is, what do the best reps do that are, how do they prepare and how do they practice? Well, it's so interesting. Like, that story is great. And I heard Al-Syne Jr., he speaks about, you know, going to see Kobe Bryant train. And the 3 o'clock in the morning is not an exaggeration.

He was actually in the gym at that time, which is incredible. You know, I was like, oh yeah, I must be 6. No, no, 3. So from that, you know, people who managed to achieve that level of greatness first time around have so much respect for that because there are so many distractions out there. And in your sales career, as you progress and as you get more successful, I mean, you're going to have, especially now that face-to-face is pretty much back, you know, not as much as it was, but we're still at the business dinners coming along. We still have, you know, events that are coming back. And there is that point of, you know, you can make that decision. If I'm going to look, let's make the most of this and turn it into a bit of a jolly versus let's actually get the most out of it from a business perspective.

What I see top reps do is they, in every single moment, they are essentially ready for that moment. So good example is if, you know, if somebody's at a conference and they, you know, maybe they bump into somebody who, you know, could be their ideal persona, maybe they work at the companies they'd love to try and get into. Rather than just have a conversation, oh, what took you here today? Oh yeah, the weather, it's this, it's that. They're asking, so what's this person looking to achieve? What do I reckon they're actually here for? What do we think they want to get out of that? And what you'll notice is when they're chatting, they'll take genuine interest in the person they're speaking with.

It's like there's a sign pointing at them saying the most important person in the world. And then they're trying to serve them values. So they might say, oh yeah, there's a talk on that you could look, you should look to check out. Or actually, have you seen that such and such is over here? Yeah, I must introduce you to them. So they're doing things which are not necessarily going to get them paid or get them business in the short term, but it's giving value to the other person. And then the other people, you know, you're always looking at these elite reps going, well, how did this person get introduced to that person? Well, actually, it turned out that they've done something else for this person here.

Now, when I look at reps who are, you know, if you look at your calendar, I mean, that's a really good indication of what's important. So let's say this week, you might have a few discovery calls, you might have a couple of demos to deliver, you know, maybe you've got an on-site meeting, whatever it could be. You know, the top reps, they look at that and they actually, they set preparation time aside so that they can make the most out of that, right? So sometimes it can be when they're traveling there, you know, they might be thinking about it. Sometimes it can be actually, oh, I want to go down, do the work, go through the deck, whatever else. And what they do is like, they review their calendar, you know, they establish what preparation needs to be done.

They typically add it to their diary at some place and pull in the people who they need to support them on it. Crucially, they do it. And that means that they are like, you're ready at that point. And like that acronym, that's something I share with you, it's ready. And that's what, that's what they're doing. How much preparation should you do is another thing. And this is something we've got to be so careful of. This is not an excuse for procrastination. This is not an excuse to fill your diary full of, you know, preparation for all these different tasks. It is getting us down to doing the level of preparation that's appropriate versus, I suppose, the percentage of quota that is going to be knocked off, that you're going to actually retire from being successful in that.

So if you're an enterprise seller, you can spend two or three days preparing for a meeting. You can spend a week preparing for a meeting because you might sell one or two deals a year or even just that one. But if you work in an SMD, you know, you probably look at maybe 20 minutes because you might have to sell 10 deals, 20 deals a month, depending on what you're providing. So from that perspective, it's been really focused on not letting this become a big time waste for you. Brilliant. Yeah, I think that's the key. It's like there is a level of prep before a meeting that is kind of too much is too much, right? Where you're overprepared for it. It's just like a presentation. There's been times where I've overprepared for a presentation where you were saying earlier, where like, you know, the SE is like, dude, like we can almost recite this word for word at this point.

This is the fifth time we've done this. And with those, there is a fine line, right? Because if you are so prepared and you think through every scenario, then you're almost on a script and you're not allowing the subjectivity. You're not allowing the flow of the meeting. You're dictating the conversation, which is what you shouldn't do. And so I kind of ebb and flow on this sometimes because, you know, Gary Vaynerchuk, I saw him one time do an interview with LinkedIn and he actually said, you know, and I agree with Gary on most stuff, okay? This is one I don't, where he said, I don't prepare for any meetings because I go in as a blank slate because I just want to listen. I just want to listen.

I want to hear what their problems are and I want to figure out what the best solution is because if I go into like prepared, well, now I'm kind of angling the conversation. I'm asking leading questions. I'm, you know, making assumptions about certain things. And I'm like, Gary, you know, I appreciate your, I like the concept that you're talking about there, but you're Gary Vaynerchuk. Like people are going to want to talk to you. People are going to want to tell you their problems and they, they enjoy the, just having Gary Vaynerchuk in the room with them. So it's the normal everyday sales rep doesn't get the audience that you get, doesn't get the, the, the transparency that you get from the client.

So they have to prepare. So I guess from your standpoint, like, when do you know you to your point that you've prepared too much? Cause I've seen people, by the way, freeze up on stage because they forgot their, the next line they'd like, they forgot, like, oh my God, you could tell they were just hammering down this track, talk track with their presentation and they just blanked and now they're screwed and they have no ability to adapt. So where's that fine line between preparing too much and not enough? I think the fine line is not going into a robotic. And what I mean by that is the worst time to think about what you're going to say is in the moment that you're saying it. So you've done so many meetings and you've had so much sales experience that yeah, you can go into every sales meeting.

I probably do pretty well thinking on the spot. However, if you're going into discovery, if, you know, if it's demo, whatever the situation may be, you know, I think there are certain pieces of value that you should want to hit upon. There should be certain phrases and certain messages that we want to hammer, we want to make sure what they're underlined and maintained so that you know what you're going to say for those. They're not just left the chance to see what you come up with on the spot. So knowing that sort of thing. And if you're going to be asking questions in discovery, you broadly know where you want to go with it. Knowing where those questions and where those talk tracks can go, I think is quite important.

Having some questions ready that you can ask a version of that. But again, it's a real conversation. So we have to be prepared. Some of the things that you're, if you're going into it, like what are you looking to achieve? Right? So let's say if we're into a demo, well, I want to show the three or four things that's going to drive value that delivers that outcome that they're actually after. So they can confidently make that yes, no decision. Okay. Yeah. That'd be, that'd be great. And then we can look to move on to the next stage and, you know, again, to the nuance of it. But then we have to look at what are the other possible outcomes that we could explore? You know, are we missing stakeholders in the room?

Is there a possibility that they're going to turn around and say, no, something's changed from the last meeting and being aware of what that could be and then being able to tackle it. So don't mistake preparation for delivering a script or going in with a message. Use it as something where you've got information and you broadly speak and know questions and areas you want to speak about. And you do have some turns of phrase that you can lean upon, but don't feel you have to use everything. Use it appropriately because it is real conversations with real people. And that's the difference because like, if you just go in, scripted questions, same demo everybody else gets, that used to work a lot.

It's working a lot less now. A lot less. And you know, one area that I always talk about when it comes to preparation and I think to your point of being able to speak on the fly is objection handling. You know, it always cracks me up where reps look at object, like it's almost like every time they get an objection, it's like the first time they've ever gotten it. It's like, oh my God, like, and they stutter through it. It's like, you could summarize, there's probably about seven to 10 objections we all get all the time. Like literally, we don't have budget for this. This isn't the right time. It's not a priority for us. Call me back in six months. Like, you know, this is, you're too expensive.

The vendors are the other vendors bad, whatever it is. Like, like, so my whole thing with objection handling, yeah, there's techniques, right? And I think it's important to understand those techniques, but it's more about just being proactive versus reactive. Like, you should have a, a flow, not a, not a perfect script every time somebody gives you objection, but you should have a mental kind of flow of how you want to handle it. Like, do you want to ask a clarifying question? Do you want to justify it? Do you want to reprioritize it? Like whatever it is so that when it happens, you can be in the moment and kind of choose which one is, is the most appropriate for it. But every rep feels like it's like, it's the same thing with closing.

Reps go, don't know when to close. It's like, you, you should kind of map that out. Like, what are you closing for? And I don't mean just the contract, right? I mean, the next steps, uh, you know, close for a meeting with power or close for all these other things. And it's like, it's always such this awkward thing when a rep tries to do it on the fly, unless they're that artist, unless they're that tier one rep, right? That is just the one that knows how to do it innately. Most other people, like you could feel the, the awkwardness around the close. And I'm like, you, you should walk into a meeting knowing what you're closing for, at least closing, you know, three, four, five different potential things here.

And then you should kind of workflow this out or practice and role play. So with that, how do you, how do you look at role playing? Cause I have some very strong opinions about role playing. I think they're garbage in most areas, but I think they're very good to prep for about to execute. So how do you implement role playing into the practice component of sales? Yeah. Role playing is, it's so interesting because nobody likes to do it, right? Let's just call that out. You know, you really don't, especially then when there's other people listening. Um, I think role playing, it can really expose weaknesses that you don't know where they are. I remember being with a business, you know, a couple of months ago and they put their, their top rep up to do a role play, uh, Whitney and, you know, whole team is listening.

I'm going to go, ah, well, okay, like it's their best rep. So, well, hopefully people learn from it. Um, person froze, didn't really know how to answer. And it became really obvious that that person was, you know, first in and just happened to get the best opportunities because they built up status in the company, but they haven't actually got the skills to deliver upon it, which is a big shock for me and him and everyone else. And it felt a bit bad for the guy, to be honest. The key thing though, is with role play, there's probably two things I'd, I'd, I'd pull in onto it. One is, if you think about those objections that you get, those seven, eight or 10 objections, right? You should have answers to those questions and they can be, you know, every quarter, have a look at what the objections that you're getting are because they are changing.

You know, as we see, we're speaking, going towards indecision and not no decision. So again, there is a subtle change that's happening out there and speak to people on your team, speak to leadership, you know, the founding team, whoever you've got access to and get their answers to it and collect the best answers there and have them ready. And if you're going into a role play situation, that is a chance for you to look to actually use some of those great answers and go through that. And then the other side of it as well is role play can sometimes open up your eyes. You know, you could call somebody, hey, I'm looking to speak with such and such and blah, blah, blah. And then somebody, yeah, no problem.

You can speak to them straight away. And then, oh, okay. And I think that's very important when you're doing role plays as well, particularly if you're leaders, because sometimes you will get that easy yes and you will get true to that person. You will get that mean. You won't always get beaten up over it. And I think mixing that into role play makes sense. But again, I would limit the amount of role play that is actually done because I don't think people enjoy it enough for it to matter. Well, it's embarrassing. It's also manufactured, you know, and so I don't, you're never at your best. You're always thinking more about what people are judging you on versus the actual ability. But where I actually think role playing does make a difference is like right before you're about to do the thing.

So it's right, it's like a football, right, right before you're about to go on the pitch, you don't, you don't, you sit there and, you know, just jump out there and start playing. You, you kick it around a little bit, you stretch out a little bit, right? So I think like right before you're doing a call blitz, that's a great time to do a role play. All right, everybody, get on a call right here. Here, I'm going to run a couple of scenarios by you. Let's hit some gatekeepers. Let's get through to a couple of people. Cool. We good. Or like right before you're about to go to a meeting, hey boss, here's the scenario. I'm about to go in. Here's my goal for this. I got to get to the, you know, I got to get the power.

I want you to object to me and let's pull this out. So I can just kind of loosen up a little bit here. So that's where it's almost like practical application role play, as opposed to a trainer role play with some dipshit like me, who's going to stand up there and embarrass you because I've done this a million times before. And I, you know, and I know how to guide this conversation like that. That to me is like, all right, you know, especially pulling people up on stage in front of 300 people or something like that. Like that's just asinine to do, I think. Yeah. So, so, so cruel. Yeah. And I guess I probably, in my world, that role play that you're speaking about, I'd kind of nearly, you know, push that into the dry run category and goes through it.

And even if you find just, you've got a bit of time, you're sitting there before you're going into that meeting, whether it's travel or you're, you're there, even trying to write this objection comes along, what's going to happen? That objection, what's going to happen? And then there are, there are strategic things that you can look to do. You know, sometimes if you, if you're at an on-site meeting and you know, you're going to be leaving and, you know, if there is, let's say there's a chairman or, you know, CXO in the meeting and you brought your RVP or somebody along with you, you know, can you actually strategically make sure that they get a little bit of time to chat together as well. So there's a bit of executive alignment there.

Are you looking to match people on the deal side with your, when you're on your side as well? So that when it comes to it is there's multiple different voices speaking to customers. And that doesn't just have to be a mid market or a beyond thing. You can even be looking to do that in SMB as well. I'm looking to utilize that wider team. Now these days, like these little things, they do put on, they do help you get that deal a little bit more. And we have to go that step further to actually figure out and look to de-risk things. And one thing that I always think is super important that we tend to overlook when thinking about de-risking is, you know, even like, let's say a CEO wants to buy something.

You know, they want to bring in this software and they're like, yeah, look, we want to bring in John Barrows. We know this is what we need. This is really, really healthy. We've got this gap here. If the team don't want it, like let's say a sales manager or the team don't want it, that's going to make it uncomfortable and difficult for that CEO to actually get it in and then to make sure the training's attended and it's used or whatever else. So if we take a step back, really part of us is to, yeah, we want to get the decision makers on board. We want to show the value, but we also want to have the users and people who could be involved at a lower level going, yeah, we want it as well. Actually, when are you, when, when Sean coming in, as opposed to, when is that?

I'm going to take annual leave. And these are the things that we have to think about. And that is, that can even just be as much as 50 minute phone call to get their perspective ahead of a meeting that's happening. So then you can figure out, well, here's the five or six people and these three or four, this one's against, these two don't care. And you can actually work on that then. Yeah. I do that a lot with trainings, like, cause the days of, you're right, the days of an executive making a decision and stuffing it down everybody's throat, whether they want it or not, are, are, are few and far between because it is, you know, you might get a short term engagement, but you'll never get a longterm engagement.

Um, so that's why when I get, you know, a potential opportunity, I ask them like, who are your top two or three reps? Um, because the top two or three reps usually don't like training because so much training sucks so bad. They want training, they want coaching, but they want good training. They want good coaching. And they've been through so much crap that they kind of come in with this, Oh God, you know, another waste of my, like you talked about like, Oh, you know, you're a top performer at Salesforce. And I showed up and you're like, Jesus Christ, man, a full day of training, like what the shit. Right. So I usually grab two or three of those reps and talk to them beforehand and be like, Hey man, you know, what, what's, what's your day in the life look like?

What are some of the things you want to get out of this? And that type of, so then even just that alone, then they're attentive in the session. They're actually, I'm referencing some of that conversation. So then the other reps are like, Oh shit, you know, you already prepped with some of the best reps in here to prep for this and they're paying attention. I should be paying attention. So I think there's little nuanced things that we can do right now, you know, obviously multi-threading throughout the organization, everything else. But look, I know there's a ton more in your book that we could get into, but we're coming up on the hour here. So Paul, where, um, where can people find out more information about you, about the book, about what you're doing?

I know you're doing some coaching right now for some AEs, uh, which is always something that, uh, my audience is looking for because, um, I don't do one-on-one coaching. Uh, you know, I do training and I got AMAs and everything else, but I don't do that one-on-one coaching. So where can people find out more information about what you're working on? Yeah. If you go to paulcaffrey.com and you'll find everything there. Uh, if you go to paulcaffrey.com forward slash assessment, there is an assessment that you can take, which will help you score your ability against the lead performer. So you can see where you rank and that generates a customized report, which will then give you areas that you can take away and improve on your own.

So very, very fast to do and very, very useful. And then I guess the other thing is the book, uh, the work before the work that hidden obviously sales professionals used to perform the competition. That's on amazon.com, Barnes and Noble, pretty much anywhere you can get books, you'll find it. So, you know, there's great resources. Awesome. Well, Paul, appreciate you coming on the show. It's good to see you again, man. Thanks for, uh, thanks for the conversation. I hope everybody enjoyed as much as I did. All right, everybody. Look, uh, as I always say at the end of these, go out there and make somebody smile today. Cause no matter how bad your day's going or you think it went, you make somebody smile and you know you had a good day and the world needs a lot more of that right now.

So, uh, thank you all very much for listening. I will see you on the other side. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough now to keep the momentum going. It would mean the world to me. If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network. Also check out my new website, jbarrows.com where you'll find even more ways to engage. There's a ton of free content and you can also get trained from me directly as an individual or for your team. Look, I'm out there selling every day, just like you are.

And I'm doing my best to stay on top of all the latest trends in sales and technology. So if you're looking to level up and you give a shit about this profession of sales, let's connect and make it happen together. I'll see you next time.