Paul M. Caffrey (00:02.926)
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 the 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. I hope you enjoy the conversation as much as I did. Let's make it happen.
Paul M. Caffrey (01:46.606)
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 is probably, what, five, six years ago, something like that? Not suddenly, a couple of years ago. Although you guys must have been met up. I'm in a time warp with Covid. I have no idea what time it is. It's two years or 10 years. I don't know. Yeah, yeah. Now, time is going so fast at the moment. So...
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. And besting 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 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, like, be a totally, it felt like she was a different person because she might grow an inch or she, you know, was doing something different that I hadn't seen before. I was like, holy shit, like that really set, have you started to notice?
Oh, yeah. You can notice time a lot more effectively now with kids. Yeah. And you just notice how fast it's going. I even dropped them off at a crash this morning. My wife turned around and said to me, our oldest has gone to be four in October. I'm like, oh, oh, yeah. Wow. That's quick. She's not a baby anymore. But even with like, like we were we happened to be away for a few months and just coming back, you could just say, yeah, the growth is there. They 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?
Paul M. Caffrey (04:04.302)
And then how did 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. Great place to visit. Yeah, it's fun. You know, it is a fun spot. I was a Bostonian. It's near and dear to my heart. Because actually, when the first time I went to Dublin, quick story, I...
Philip Cleary, a good friend of mine brought me around to all the pubs, right? And I had this big shitty 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, Patty 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 gonna replicate what's going on here in Boston. 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 any day. So I was like, oh, well, it's quiet. Like, why is there nobody out on a Monday? And now you're like, oh, OK, Mondays you're not supposed to be out. Right. I got it. So growing up in that culture was great crack. I as a 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's be like, well, if that doesn't work out, what's going to happen? I was like, no, it's OK. I'm going to work in research science. I'm going to cure some disease that nobody has 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.
Paul M. Caffrey (06:26.414)
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, OK, let me let's try sales. I really like 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 realised it's cloud computing thing. Only one percent 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 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 through the 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 is always on my mind. So I went, got a Masters 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. Come over here. 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 at it going, whoa, okay. So then I decided, let's give it a go. I went over, 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. You're going, I like to learn, but like.
Paul M. Caffrey (08:49.966)
I want to do a train, 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 really, really enjoyed it. Well, 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 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 should 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 tenured reps who were excellent at selling. They had a great product, did a great support and team. And you're looking at it going, that meeting, that demo, that solution presentation, that onsite 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 that 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,
I do 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, OK, there is 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 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.
Paul M. Caffrey (11:15.534)
these people who were successful, but then we couldn't actually communicate what was working and what wasn't. So then people were left struggling. People were doing really, really well. And that's what really got me into this space. Wow, 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, like a little bit of context on this. I've always said that for me, one of my, how I 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, 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 gonna 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 the 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? I remember running a side hustle, maybe 2011, 2012.
Paul M. Caffrey (13:19.79)
So there's this thing called fantasy football where you get points if people actually score goals or do well in the games that are on the weekend and English soccer and others American fantasy football now as well. It's very successful. I remember just looking at that and going, OK, hang on a second. There was a million players last year. There's one point seven million this year. OK, there's going to be one point four million projected. OK, 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, OK, that's an opportunity where something is getting bigger. So jump on it. So we did set up a podcast and we worked on national radio. It's writing for a national newspaper. And, you know, all of a sudden, your site 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 in it, but you have to understand, well, what
heck could you use that would actually help you versus others? So back then, SEO was a thing, but a lot of people didn't actually, you know, SEO optimized their website. So essentially my website, fancy who bought, 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 seen a few data points and then it's going at it and seeing if it actually 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 and those type of things. Like I fundamentally believe that Bitcoin eventually will be the currency of the world, right? Well, back or 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.
Paul M. Caffrey (15:41.87)
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 into this. 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, then I'd highly recommend putting that one on your list. 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 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? What do you think it takes to stay here as opposed to like coming in and out, you know, and after, you know, flashing the pants and then be like, I got to go to marketing or I got to go do something else here. It's way too stressful. What are some of those key ones that you're looking at right now? Well, I guess what it comes down to is.
Paul M. Caffrey (18:04.59)
If you want to achieve longevity, you're looking at doing something that's sustainable. And the burnout is a really 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 twelve 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 as 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, so 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 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 of them are qualified, shouldn't be there, the end of the month, end of quarter, you're really stressing. And then the number just turns out to be OK, or 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 Pory 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 changed his 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. I think salespeople, you know, 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. There's the I mean, that's the old work smart, not hard, right? It's like the thing. And I and I think that a lot of people, especially right now, have taken that to the extreme.
Paul M. Caffrey (20:27.598)
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. 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 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 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. Cause I'm a task management animal. I'm a zero inbox guy. So I get satisfaction personally by checking off things on my list. I get anxiety when I look at my inbox. I was up until two o 'clock in the morning last night.
because I need 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 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 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, now 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,
hammer in 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?
Paul M. Caffrey (22:44.654)
balancing that quality quantity approach. Yeah. And it's, you know, it comes into something actually, my co -author, Phil Ann Jones, 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 pull in your list from ZoomInfo, Sales, whatever it is, and then just start hammering it. And yeah, you'll, your metrics will be good if you're still being driven to...
you know, send so many emails, make so many calls, you can hit those vanity metrics very, very easy. But if you take a step back, what the best are doing is they're really asking themselves, well, what am I looking to achieve? And how am I going to achieve that? 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...
Yeah, 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. Well, 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 an admin and you're chatting to whoever, you're chatting to CS but you resell to marketing.
And again, I agree with you, John, you need to have those conversations. You need to understand, you know, is the status quo, is there 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 a wrong decision. That's something that I'm kind of seeing. Oh, that's absolute.
You know, yeah, have you read actually people listen to the podcast and probably sick of me saying it, but have you read the book Jolt Effect? Haven't seen it's a little one. I'm with the check. I'm honest. Put it on your list is the crew that wrote corporate executive corporate executive board, the ones who wrote Challenger, Challenger sale, Challenger customer and Jolt Effect. Jolt Effect is 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.
Paul M. Caffrey (24:58.446)
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 opened 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 pain 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. I think like we've we're looking to evolve beyond just asking what's the negative impact? I'm not going ahead with this. I mean, yeah, OK. 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 it's really the start of conversations. I also think you do quite naturally, John, as well as.
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 me can be exactly the same. But if you actually frame it that way, then you're in the position of getting people to lean in. This person's done their homework. They saw that this about the company. They saw that I did this role and...
Paul M. Caffrey (27:16.526)
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, to that's great. A trade place anytime. Yeah, exactly. Yeah. But you can you can flip that around and do a little bit of a bit of an eight mile M &M. Some people might not remember that movie, but essentially, it's like we can call out that. I'm only a year in the industry and you know what I'm seeing is this. I think it means that. But you're obviously much more experienced.
What's your take on this? And then just flipping around and all of a sudden, you're having some daffrence 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 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 you're taking me through this, you're taking me through that. Yeah, 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 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, bank 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 where 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 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, Tiger Woods is another perfect example of that. He rebuilt his swing probably 15 times in his career, right?
Paul M. Caffrey (29:31.95)
Even when he was at the top of his game literally when he was the number one golfer in the world He went Rory did his swing a hundred percent and practice practice practice practice and that 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 it was it was like a ballet man. It was like, oh my god, like look at what it that 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, Allen Iverson, who when he was 19 years old, went to LA. 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 LA, and Allen Iverson's like, yo, where you wanna go? You wanna hit the clubs? Like, let's go to the clubs and have some fun. And he's like, and Kobe was like, all right, which club do you wanna go to?
I was like, oh, just tell me you're right. He's like, cool. He's like, I'll drop you off. And AI is 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, nah, man, I go back to the gym. And AI was like, what? Like, it's 10 o 'clock at night on a Friday in LA, 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 you'd be up at 3 o 'clock in the morning at the gym.
like beating everybody there. So what do you, what's the right preparation, I guess? What's the right practice? Cause 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 are the best reps do that are, how do they prepare and how do they practice? Well, I, I, I was so interested in like that story is great. And, um,
I heard Alisdine Jr. He speaks about going to see Kobe Bryant train and the three o 'clock in the morning is not an exaggeration. He was actually in the gym at that time, which is incredible. You know, I must be six. No, no, three. 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
Paul M. Caffrey (31:45.486)
in your sales career as you progress, 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 events, StarCard coming back. And there is that point of, you know, you can make that decision and find, well, 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 a good example is if somebody's at a conference and they maybe they bump into somebody who could be their ideal persona or maybe they work at the companies they'd love to try and get into. Rather than just have a conversation, 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. They might say, oh yeah, there's a talk on that you should look to check out. Or actually have you seen that such and such is over here? 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 the other people. 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'd 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. In the top rest, 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, I want to go down, do the work, go through the deck or 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.
Paul M. Caffrey (34:04.11)
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 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 one. But if you work in an SMD, 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 I think that's the key. It's like there's there is a level of prep before a meeting that is
kind of too much is too much, right? Where you're over prepared for it. It's just like a presentation. There's been times where I've over prepared for a presentation where you were saying earlier where like, you know, the SE is like, dude, like, 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, 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 wanna listen, I wanna hear what their problems are, and I wanna figure out what the best solution is. Because if I go into like prepared, well now I'm kinda angling the conversation, I'm asking leading questions, I'm making assumptions about certain things. I'm like, Gary, I appreciate your, I like the concept that you're talking about there, but you're Gary Vaynerchuk. Like people are gonna want to talk to you, people are gonna want to tell you their problems, and they enjoy the, just having Gary Vaynerchuk in the room with them. So.
Paul M. Caffrey (36:24.462)
It's the normal everyday sales rep doesn't get the audience that you get, doesn't get the transparency that you get from the client. So they have to prepare. So I guess from your standpoint, like when do you know your point that you've prepared too much? Because I've seen people, by the way, freeze up on stage because they forgot 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 it 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 it's demo, whatever the situation may be, 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 that 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...
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. OK, yeah, that would be that would be great. And then we can look to move on to the next stage and, you know,
Again, it's a nuance of it. But then we have to look at what are the other possible outcomes that we could explore? Are we missing stakeholders in the room? Is there a possibility that they're going to turn around and say, you know, 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.
Paul M. Caffrey (38:40.974)
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 there's real conversations with real people. And that's the difference because 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 objecti... 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, uh, uh, uh, and they stutter through it. It's like, you could summarize, there's probably about seven to ten objections we all get all the time. Like, literally, we don't have a 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, and 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 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 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 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, you know, close for a meeting with Power, 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 awkwardness around the clothes. And I'm like, 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 roleplay. So with that, how do you look at roleplay? Because I have some very strong opinions about roleplaying.
Paul M. Caffrey (40:56.782)
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. Let's just call that out. You know, you really don't, especially when there's other people listening. I think role playing, it can really expose weaknesses that you don't know where they are. I remember me with a business, you know, a couple of months ago.
and they put their top rep up to do a role play with me and the whole team is listening. I was like, OK, it's their best rep. So hopefully people learn from it. First and froze. Didn't really know how to answer. It became really obvious that that person was 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 pull in onto it. One is if you think about those objections that you get, those seven, eight or ten objections, right? You should have answers to those questions and they can be 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, 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 could call somebody and say, 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.
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 through 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.
Paul M. Caffrey (43:11.79)
for what it's made of. It's embarrassing. It's also manufactured, you know, and so 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 before you're about to go on the pitch, you don't, you sit there and just jump out there and start playing. 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. I'm gonna 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 gotta get to 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 know how to guide this conversation. That to me is like, alright, especially pulling people up on stage in front of 300 people or something like that. That's just asinine to do, I think. Yeah, so, so cruel. Yeah, and I guess I probably... In my world, that role play that you're speaking about, I kind of nearly pushed that into the dry room 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 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 strategic things that you can look to do. You know, sometimes 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, the CXO in the meeting and you brought your ORVP 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 on your side as well? So that when it comes to it is there's multiple different voices speaking with each other. 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. These days, like these little things, they do put on...
Paul M. Caffrey (45:29.006)
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, like let's say CEO wants to buy something. They want to bring in this software and they're like, yeah, we want to bring in John Barrow's. We know this is what we need. This is really, really helpful. 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 kind of make it unculturable and difficult for that for that CEO to actually get it in and to make sure trains attend and it's used or whatever else. So if we take a step back, we're really part of us is to, yeah, we want to get the decision makers on board. Want to show the value. We also want to have the users and people who could be involved at a lower level. Yeah, we want it as well. Actually, when you break, when when Sean coming in as opposed to when I 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 meet in the top. And then so they 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, because 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 few and far between. Because it is, you know, you might get a short term engagement, but you'll never get a long term engagement.
So that's why when I get a potential opportunity, I ask like who your top two or three reps and can I talk to them? 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, another waste of my, like you talked about like, oh, you were 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, be like, hey man, you know, what's your day in the life look like? What are some of the things you want to get out of this? And that's, 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 nuance things that we can do right now, you know, obviously multi -threading throughout the organization, everything else, but.
Paul M. Caffrey (47:50.094)
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 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, which is always something that my audience is looking for because I don't do one -on -one coaching. 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, you'll find everything there.
If you go to pawlcaffey .com for a 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're ranked 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 and the work before the work, the hidden habits, lead sales professionals used to perform the competition.
That's on Amazon .com, Barnes & 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 the conversation. I hope everybody enjoyed as much as I did. All right, everybody, look, as I always say at the end of these, go out there and make somebody smile today, because 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...
Thank you all very much for listening, and I will see you on the other side.
Paul M. Caffrey (49:18.894)
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.
