Should You Move Into Sales Management?

John Crowley is an Author, Speaker, Coach, and the Creator of the Knuckle Dragging Sales System.

In this episode of The Salesman Podcast, John shares when to and when not to take the leap up to sales management.

Win More Deals Or Your Money Back.

Selling Made Simple Academy: The proven way to improve sales results. Trusted by 2,000+ students.

Learn More

Featured on this episode:

Host - Will Barron

Founder of Salesman.org

Guest - John Crowley

Creator of the Knuckle Dragging Sales System

Resources:

• Previous episode: #585: SIMPLE 3-Step Sales Process (That Drives HUGE Results) With John Crowley
• Knuckledraggingsales.com
• John on Linkedin
• Book: Knuckle Dragging Sales: A Primitive Process To Make More Money
• Book: Never Split the Difference: Negotiating As If Your Life Depended On It
• Check out John’s Vacation Checklist 

Transcript 

Will Barron:

Coming up on today’s episode of the salesman podcast.

John Crowley:

People come in, they could be fantastic sales people. They flounder as a sales manager and before they know it, they’re back into sales because it just wasn’t the right fit for them. So I think there’s a lot of mental preparation that goes into this. And you need to talk to your boss, to your mentors to better understand, am I ready for this next step? Is this next step the right move for me? Or do I move into more of a senior sales role before I take the lead to people management.

Will Barron:

Hello sales nation, I’m Will Barrow and host of the Salesman Podcast, the world most listened to B2B sales show. If you haven’t already, make sure to click subscribe. And with that, let’s meet today’s guest.

John Crowley:

Hey Will, I’m John Crowley. I am the author of the Knuckle Dragging Sales book. I’m the host of the knuckle dragging sales podcast. And I help two types of people. One, is I help mid-size organisations restructure, reorganise broken sales systems and help them create a sales infrastructure that is capable of scaling revenue. And then two, I also help sales professionals develop an independent brand so that they make more money and take control back of their career.

When Should a Salesperson Consider Getting Into Management? · [01:40] 

Will Barron:

On this episode of the show with the legend that is John, and we’re diving into his story of how he went from potentially fired and getting sued, to a VP of sales at a really cool organisation. We’re also getting into whether you should make the leap into sales management and all the horizontal leap that salespeople can make. So if you’re bored of your sales role, even if you’re having success in it, this should give you some food for thought. If you’re loving sales, this might give you some career advice for the next five, 10 years moving forward. So, let’s jump right in. When should a salesperson be considering going into management, leadership, entrepreneurship, anywhere else other than selling? When should they be perhaps thinking or contemplating about making that change?

“You get paid handsomely by doing your job very well. It’s only until you start doing your boss’s job that then you’re ready to make that leap into that next step.” – John Crowley · [02:17] 

John Crowley:

I think the time to do it is when you’re at a point where you have mastered the sales process, the entire sales game, you’re looking for that next challenge and you’re looking to manage people. I think at that point in time, that’s when you should start thinking about it. The first step that I give, the first piece of advice I give everybody that’s in this position, well, is that you get paid handsomely by doing your job very well. It’s only until you start doing your boss’s job, that then you’re ready to make that leap into that next step. So always remember that you get paid well for selling well, you’ve got to prepare yourself for that next step by doing their job.

The Difference Between Managing Yourself and Managing a Sales Team · [02:58] 

Will Barron:

And the key thing I picked up on here, other than the challenge and other side of things, because we can just do bigger deals right, we can get a more prestigious sales role, we can go to a bigger company selling to enterprise. So we can deal with the challenge elements of this in a sales career, but managing people seems to be the big gap between a sales professional and management or sales leadership. How different is it to manage people than it is to manage yourself? Because that’s essentially what we’re doing as sales reps, right?

“Leading people can be completely exhausting. And I think that’s why you see a lot of times, people come in, they could be fantastic salespeople, they flounder as a sales manager and before they know it, they’re back into sales because it just wasn’t the right fit for them.” – John Crowley · [03:17] 

John Crowley:

It is night and day Will, there is no comparison. It’s a completely different set of skill sets that you have to bring to the table in order to be prepared to lead people. And that leading people can be completely exhausting. And I think that’s why you see a lot of times, people come in, they could be fantastic sales people, they flounder as a sales manager and before they know it, they’re back into sales because it just wasn’t the right fit for them. So I think there’s a lot of mental preparation that goes into this. And you need to talk to your boss, to your mentors to better understand, am I ready for this next step? Is this next step the right move for me? Or do I move into more of a senior sales role before I take the leap to people management?

Key Defining Attributes of Effective Salespeople Who Make Great Sales Leaders · [03:43]

Will Barron:

And how do we know if we are going to be, not necessarily good at managing people because you could have all the natural talents and you could still suck because you don’t put in the effort, but how do we know if we are perhaps aligned to manage people? I would like to consider myself as a half-decent leader. We’ve got a decent sized team now out here at the Sales School and the Salesman Podcast. And I don’t know if they’d tell me, but I don’t know if that’s a good thing, a good sign or a bad sign, but no one’s ever said that I suck at it, right? And I give people plenty of opportunity to give me feedback, and I feel I’m probably a better leader than I am even in sales. I consider myself reasonably good at selling at this point. So how do we know, and I’ll give my thoughts on this as well, but how do we know whether we are naturally inclined to be good at selling, which is one set of skills versus managing people, if that’s a completely different set of skills?

“I can promise you one thing, if you are looking to get into sales management because you’re going to make more money, you’re not. You’re absolutely not going to make more money.” – John Crowley · [05:02] 

John Crowley:

I think the question becomes where do you derive your energy from? If you’re somebody who drives energy from closing that big deal, making the big advance, getting that big commission check, then it may not be for you. If you’re the type of person that likes helping other people, that likes helping them accomplish their goals, whether it be in sales goals or whether it be career goals, that to me would be an indicator that, you know what? Sales management might be right for you because it really boils down to your why and why you’re getting into it. And I can promise you one thing, if you are looking to get into sales management because you’re going to make more money, you’re not. You’re absolutely not going to make more money.

Can Top-End Sales Professionals Make More Money Than Sales Management? · [05:10] 

Will Barron:

Is it possible to make more money or at the top-end of sales professionals, are they at the same level as sales management?

John Crowley:

I would say that the top-end sales professionals should be making more money than sales management. Where you could get to a point where you make more money, is if you get into senior executive leadership. So, that VP of sales level. Once you get to that level, that might be a place where between stock and equity, you could make more than you would as a salesperson.

Will Barron:

Sure. And just to add my spin on this, humbly. I know for myself, it’s one thing to do a deal and do it on your own, and that’s exciting and nothing better than closing a sale that puts money in your pocket. But it’s quite another thing, and I didn’t realise this until I started managing people and bringing people onto the team here at the Salesman Podcast and the Sales School, that managing other people so that they hit their goals, which allowed you to an even bigger goal, is even more exciting than just closing a deal. So I don’t know if you have the kind of similar thoughts and opinions on that, but that was a revelation for me. And that was my clarifying moment of, if all this was to go to complete shit and it was to fall apart and I needed to get a job, I’d probably look at sales management or sales consulting or something like that rather than just a straight sales role now.

John Crowley:

Yeah. I think though, there’s still a lot of lone wolfs that are out there and those people will always be lone wolfs. But if you have any inkling for… If your compassion for people is there, then I think sales management could be the perfect role for the right person.

How to Transition From Sales Into Sales Leadership · [06:50] 

Will Barron:

Okay. So, before we engineer out everyone who listens to the podcast of a salespeople, my audience goes to zero overnight because everyone is applying for sales management roles. What do we need to have in place before we start applying for a sales management job? And most of the sales managers that I know were sales people, internally there was a job opening and they got that job internally. And there wasn’t much preparation done, there wasn’t any training done, and they started to, like most sales people, they started learning sales management on the job, on us, as opposed to doing preparation beforehand. Is that the best way to go about it? Or are the resources, should we be reading books? Should we be doing prep before we proactively take that leap to sales management? 

John Crowley:

Yeah. I would say there’s three steps in the process. So one, is to note and to mention your intent. Two, would be to focus on investing in yourself. And then three, make it very clear to your boss, your manager, that this is something that you aspire to do, and that you’re willing to volunteer to take on more work. So those are the three steps that I would encourage people to do. Do you want me to expand on those or not?

Will Barron:

Yeah, for sure. Especially the volunteering element of it, because I’ve never really considered that before. But then there might be some weird team dynamics that might go on if one of your colleagues starts half managing you on a Friday afternoon. But I’d love to know more about the benefits of that.

John Crowley:

Yeah. So let me start with intent. Intent is simply saying to your boss, your managers, your leadership, your executive’s leadership that, “Hey, my intent is in the next six months, 12 months, 24 months to move into some sort of managerial role.” So at least they’re aware that this is your career aspiration. The second thing would be that when you’re talking about volunteering, the key to volunteering is you’re not going to volunteer to take on some of the managerial roles, it’s more of some of the support that you could offer to your manager. So, a good example would be facilitating a meeting at one of your district meetings, leading a course or leading some sort of training, doing a book club with your fellow teammates.

John Crowley:

Those are all examples that you could go to your boss, say I would like to volunteer to give my efforts. And I think what happens is then the boss knows that, okay, now I know their intent is to get into sales management. They’re taking some steps to get there. And then the last piece of that equation is investing in yourself. And yes, I do think that you should listen to podcasts just like this, you should be reading tonnes of books, and there’s plenty of great managerial sales books out there that you could read in no time whatsoever and be up to speed on how your first couple weeks, months, a year as a sales manager should look. And I could tell you nine times out of 10, it’s usually a lot different than what you think it could look like.

Making the Leap From Sales Into a Management Role · [09:35] 

Will Barron:

And does all this have to be done internally? And what I mean by that is as a VP of sales, an ex VP of sales, would you hire a salesperson from another company externally for a sales management position? Or would you only ever hire a sales manager or someone internally?

John Crowley:

No, I would absolutely hire someone from outside, especially if they have sales management experience. There’s no one that I’m going to say no to, whether it’s internal or external candidates, I’ll look at them all. But I do think that that leap from sales… I just think back to when I made the leap. When I went from sales rep to sales manager, my head exploded. Will, I had no clue what I was doing. I had no business in being in that position and I quickly got eaten up, and chewed up and spit out real quick.

John’s Intriguing Story of How He Made the Leap Into Sales Management · [10:23] 

Will Barron:

What does that mean? Tell us a little bit about that story, that journey, from day one of… I’m assuming to get the position you were doing great in sales, what happened from day zero to getting chewed up?

John Crowley:

So, there wasn’t a big time span between days zero and getting chewed up. So what happened was, at the time, I was very young, I was probably 26, 27 years old. I was working for a big, huge… One of the big pharma companies, and they moved me into this role of an assistant regional manager. So the assistant regional manager was somebody who really helped out the regional manager. And in the event of a maternity leave or FMLA or something else, I would step into one of those managerial roles for a short term. Well, one of those roles that I stepped into was a team that was full of ladies who were pregnant.

John Crowley:

And when I say they chewed me up and spit me out, I mean, they would miss meetings and I wouldn’t know how to react to it. They’d show up late, I wouldn’t know how to respond to it. They would come to me with complaints that were all valid complaints, but I wouldn’t know how to handle it. So, I was so far in over my head Will, that was the first time where I realised, whoa, I’ve actually gone too far. And I ended up leaving that company and going to a different company as a sales rep, because I was so ill-prepared to make that leap.

John’s First Stint as a Manager was a Total Disaster. How Did He Dust Himself Up and Rise From a Typical Sales Role and Become the VP of Sales? · [11:41] 

Will Barron:

I don’t know what it’s called. You might know what it’s called John. There’s a something law. It’s a business law where most people end up in a job where they’re slightly over their heads, and it would be better off for both them and the organisation if they were in the job below where they’re at. I can’t remember what it’s called. But it seems to be very common and stresses people out because the society, the way the businesses work, everyone’s trying to push themselves and you’re trying to be pushed up the ladder because obviously it’s far cheaper to hire someone internally than it is to hire an external candidate. So with all that said, how did you then go from back to salesperson back to, or get into the kind of VP level?

John Crowley:

Yeah. So this is an interesting story Will. So this is going back seven, eight years ago. I was working for a big fortune five company. So, one of the five biggest companies in the United States, which means big pockets, deep pockets, lots of lawyers. And at the time I was recruited to go to a startup in what I perceived to be an adjacent space. The company I was working for did not see it as adjacent, they saw it as directly competitive. And as a result, before I could even resign, they fired me for breach of my non-compete. They then subsequently sued me for only $10 million. That’s it Will. I mean, I got it sitting in the bank, I took care of it a long time ago. It’s all under the water, it’s under the bridge. I’m just kidding.

John Crowley:

So they sued me for $10 million and we ended up settling out of court. But what ended up happening was, I had this brutal two year non-compete where I couldn’t sell widgets in space. So not only had I gone from being a good, high-performing sales rep making a lot of money, to now all of a sudden, unemployed. I was unemployable because no one would touch me with a 10 foot pole. So I spent about three years just trying to find my way. And where I found a little bit of traction was, I live in Nashville, Tennessee. There’s a big startup community here. And I started consulting for some of the startups and helping them with their sales infrastructure, that whole sales structure process.

John Crowley:

And so, after a couple of successful consulting gigs at no fee, I did it at no cost, I then picked up a couple of midsize companies, which then led me into some of the larger companies. And the last company I consulted for was a big fortune 14 company. So the 14th largest company in the US. And eventually they brought me on as their VP of sales. So that’s how I made this transition from sales rep to VP of sales. It was largely due to me being in a very unfortunate circumstance, but I made the best out of it. In the long run it worked out great for me.

Will Barron:

There’s probably, not lessons, and I’m sure you’ve learned some lessons from that experience, John, but it’s interesting because I went from the biggest, flexible endoscopy company in the world, to the biggest and most successful rigid endoscopy company in the world. And then when I left that job, I did some consulting back, marketing consulting for the original company that I worked for. No one [inaudible [00:14:38], all that happened was my boss snatched my laptop away as soon as I handed in my verbal notice to him when we sat down and had a meeting at a nice hotel over at near Liverpool, because he didn’t know what he didn’t know what to do, what was going on. But it was interesting that it seems some of the scenario…

The Impact of Corporate Culture on Sales Management · [15:05]

Will Barron:

It seems even more egregious, outrageous scenario that I was in, and no one tried to sue me. So, where I’m going at with this is, how different are organisations culturally when you’re trying to make that leap from salesperson to management, when you’re making that leap from individual contributor to managing a team, whether it’s regards to legislation, laws, people trying to cover their own asses? Is what you’re sharing here only applicable to the US, perhaps Canada as well, or is this translate to elsewhere in the world?

John Crowley:

I will say in the industry that I was in and I won’t share which industry that was. In the industry I was in that was very commonplace. And I was one of the first ones to really kind of experience the wrath of what a big fortune five company can do to you. But yes, in that space, it’s very common, unfortunately, and it’s a situation where it leaves a lot of sales people in a predicament.

Will Barron:

Because we never covered this on the show before and I don’t want to derail the show, but I thought that was interesting to just hear and then dive into a little bit further because what I was doing, I was spending a lot of time in the NHS, I was selling to the government. There was lots of legislation involved. There was lots of opportunities for me to be sued. And I screwed up loads of times and probably could have been sued, but I think culture kind of plays into this and turns it into more of an adult conversation. So just for the audience to keep that in the back of the mind, depending on if you are selling, I don’t know, shoes, you’re probably fine, right. If you’re selling instruments that go inside patients, you’re probably paid more for it, but it’s interesting to hear different stories and backgrounds and the litigation that can go on with all that. Anyway, get all that out the other way unless if you’ve got something to add.

“When you join a company, take your non-compete and bring it to a lawyer. Have a lawyer take a look at it and tell you all the different nuances of that contract so that in the future, if you ever get yourself into a sticky predicament, at least you know what you’ve got going for you and what you’ve got going against you.” – John Crowley · [16:50] 

John Crowley:

Let me just add. Will yeah, let me add one more thing. I think the moral of the story here Will, is that when you join a company, take your non-compete and bring it to a lawyer. Have a lawyer take a look at it and tell you all the different nuances of that contract so that in the future, if you ever get yourself into a sticky predicament, at least you know what you’ve got going for you and what you’ve got going against you. 

Why Consulting an Excellent Avenue for Salespeople Looking to Gain Management Experience and Eventually Transition Into Sales Management · [17:12] 

Will Barron:

Got it. Smart. Well, that was the feedback I was searching for. That was the answer, the golden nugget. So I appreciate that John. Okay. So consulting is something that I… So I get asked to do consulting all the time. I will help companies and especially startups that I just want to spend time with, that I might want to invest in, in the future. And I’m no expert in any of this, but I’ve got some interesting anecdotes, both on the marketing side of things, with how I’ve grown the podcast and on the sales. So I get asked all the time to do consulting and I never typically charge for it. And when I do charge for it, it’s only with large organisations and I just kind of screw them with the fees because I don’t really want to do it for them.

Will Barron:

So, with all that said, is consulting as you’ve outlined here, is that a relevant avenue for sales people to get experience outside of just selling, that maybe is the difference on a CV or what people in the US call resume?

John Crowley:

Resume.

Will Barron:

Resume.

John Crowley:

Yeah.

Will Barron:

Could that be the difference? Just volunteering a bit of your time to help consult for a charity or a startup? Is that a differentiator if you were looking to hire a sales manager?

“I think there currently is not enough attention paid to the sales infrastructure. Leadership, non-sales leadership a lot of time thinks that salespeople should just be able to sell things and they should be able to do it often and they should make it repeatable. Which is all true, but you need a process and infrastructure there to support that sales process.” – John Crowley · [18:48] 

John Crowley:

Yeah, absolutely. I think that that is a great differentiator. And the reason I like it, isn’t so much about the work that you’re doing, it’s more about the exposure you’re getting. So you’re able to see the inner workings of all different sizes and types of companies. And going back to the question you asked earlier, does culture play into it? Every single company has their own unique culture. So I have found it fascinating. It’s one of the things that I’m really passionate about, is learning about the individual cultures and then seeing how that culture manifest itself in sales organisation. And a lot of times you see some similarities between these organisations. I think there currently is not enough attention paid to the sales infrastructure. Leadership, non-sales leadership a lot of time thinks that sales people should just be able to sell things and they should be able to do it often and they should make it repeatable. Which is all true, but you need a process and infrastructure there to support that sales process.

The Meaning of Organisational Culture and How it Affects an Individual Salesperson · [19:08] 

Will Barron:

And for the knuckle dragging salesperson listening to this, myself included, what culture perhaps is talked about and understood at a VP level, at a director and executive level? What does culture mean for the individual salesperson listening to this?

“I think that as a salesperson, a lot of times it’s harder to see the culture because you’re at the kind of the bottom level of the organisation. But if you can explain to senior leadership how their behaviours are negatively or positively impacting their salespeople, that’s the light bulb that goes off in their head.” – John Crowley · [19:57] 

John Crowley:

I think what it means to the individual salesperson is that there is an underlying current that flows within an organisation, and that current can be positive, it can also be negative just like any current that’s out there. I think that as a salesperson, a lot of times it’s harder to see the culture because you’re at the kind of the bottom level of the organisation. When you get into that senior leadership, you’re able to see the senior leadership’s examples that they set and then how it flows down to those salespeople. So, it’s a very interesting and unique perspective to try to understand somebody’s culture. And it takes a long time. And they’re always evolving too. So that’s what makes it also difficult. But if you can explain to senior leadership, how their behaviours are negatively or positively impacting their salespeople, that’s the light bulb that goes off in their head.

How Salespeople Can Pitch or Announce Their Intentions of One Day Getting Into Management · [20:17] 

Will Barron:

So, if we were going into a interview and we were pitching ourselves, or maybe this is pre-interview, we were generally throughout the year, the 12 months that we’ve kind of set aside this goal of get team into sales leadership, sales management, we’re pitching throughout that process, talking about culture and how we would perhaps take the vision of the CEO and translate that into a sales team below us, for want of a better phrasing, what else would we be wanting to talk about? What else would we want to pitch within the interview? What would we want to present that would make us stand out as not a salesperson who’s bored of selling, who’s pretty good at it and just wants something else to do because they’re sick of customers wining at them and they want salespeople wining at them instead? What else would a pro…? What else would make you go, holy shit this dude, or this girl is going to crush it in a leadership position?

“When you’re working in sales, generally speaking, you’re very tactical. You’re being told what to do and implement those tactics in your territory. I think when you get into sales leadership, sales management, you have to have more of a strategic focus.” – John Crowley · [21:25] 

John Crowley:

I would say two things. It comes down to planning and financial acumen. And so, what I mean by planning is you need to be more strategic. When you’re working in sales, generally speaking, you’re very tactical, right. You’re being told what to do. You go implement those tactics in your territory. I think when you get into sales leadership, sales management, you have to have more of a strategic focus. And so, the way I advise some of my folks that are trying to move into that position, is I tell them do a business review, a quarterly business review with your manager that just shows them the way you’re looking at your business. And I actually have a sample template pitch deck that I can send you Will, if your listeners want it.

“If you want to learn one thing, sit in on a budgeting meeting because it was one of the most brutal negotiations that I have ever sat through in my entire life.” – John Crowley · [22:15] 

John Crowley:

But it’s just a quick sample of how I set up my business review internally. So that’s the first thing, is planning and then financial acumen is the second one. I can tell you, probably the biggest shock that I had when I got into sales management, was the budgeting process. If you want to learn one thing, sit in on a budgeting meeting because it was one of the most brutal negotiations that I have ever sat through in my entire life. So those are two things that you as a salesperson need to figure out, need to invest in yourself in order to be prepared for that next step.

Will Barron:

The financial side of things is really interesting to me. We’ve just put a workshop together in the Sales School where I have sat and had my mind melted by a whole bunch of financial books, consulting books and consulting framework books. And the point of the content there is to help salespeople communicate better with a financial director, a CFO, individuals like this. The answer typically is to bring your CFO into, if you’re having conversations on that kind of high level. But for you to understand the bur bones, the basics of what’s going on, if you’re doing a huge deal, it could be really beneficial just to understand it, not necessarily to be able to go back and forth and debate it.

Salespeople Looking to Get Into Leadership Must Increase Their Financial Literacy and Train on People Management Skills · [23:54] 

Will Barron:

But it blew my mind how little I know, seeing as I’m both a salesperson, I’m doing multiple six-figure deals regularly with huge companies, I’m running an organisation. I know nothing about accounting. I know nothing about finance. And so, looking back at myself, selling to the government here in the NHS here in the UK, I’d sit down with CFOs all the time and I thought I was in control of the conversation. It turns out they’re probably just dumbing things down so that I could kind of plod along and fall along with them. So other than the sales goal is hopefully an obvious answer for some of the audience, there’s plenty of books on finances, accounting, that side of things, are there any books, resources, content, other than bringing you in as well, clearly you’re consultant in this space, what else can we do to increase our financial literacy other than profit and loss and things of this nature?

John Crowley:

Yeah. So let me give you a little story real quick and then I’ll answer your question. So, when I started consulting for one of these big, big fortune 20 companies, one of the things that I noticed was that they didn’t have any CRM. So this is a company doing billions, not millions, billions of dollars that had a very rudimentary CRM. And so, I brought them the idea of implementing Salesforce, which they quickly jumped on board and were excited about. But then I spent the next 18 months budgeting. And it was budgeting for how do I get all the people trained up and ready to go? How do we pay for the actual system? How do we pay for ongoing maintenance? And these are all questions that I had to come up with the answer to.

John Crowley:

And so, going back to your question of, what would I consume in terms of a book? For me, the best book that I’ve ever read is Never Split the Difference. It’s a negotiations book, but that’s literally what budgeting comes down to. You’re constantly negotiating, not externally. You’re negotiating with your boss, with your boss’s boss, to get every penny that you can to then implement that system, or bring in that consultant or whatever it is that you’re trying to do. But it requires the financial acumen. And I do believe that Never Split the Difference is a great book. Great resource.

Forecasting Skills and the Benefits of Accurately Predicting Sales Revenue · [25:40]  

Will Barron:

I’ll link that in the show notes. We’ve had Chris Voss on the show a bunch of times. In fact, I think the most viewed video of ours on YouTube is his, we’ve got 500,000 views or something like that. So he is clearly crushing it. He is, for the audience, an ex FBI lead hostage negotiation trainer. Something like that. It is interesting dude. Okay. So with all that said, let’s go back to the strategic elements of this for a second. What does it mean to strategically plan? What’s the difference between strategically planning my territory here in Leeds with 32 hospitals? How does that compare to strategically planning as the sales manager of the north of the UK with 300 hospitals? What skills do I need to develop that translate for me being able to know, well, Mr. X and Mrs. Y in this account versus 300 accounts where clearly I can’t know every individual within there?

“Over-forecasting, driving more sales can oftentimes be as detrimental as missing your number. So I think forecasting is the biggest skillset that salespeople need to develop in order to be ready for that next level as a sales manager.” – John Crowley · [26:42] 

John Crowley:

Yeah. So, I think the one word answer to that is forecasting. I think we sit down and we put in pipelines together. And a lot of times there’s some garbage pipelines and some people keep really nice and healthy pipelines. But ultimately all that data isn’t just sitting on your manager’s desk, he or she then has to take that data and present it to his bosses. And that’s where the forecasting is so important, especially if you’re talking about a publicly traded company, because being over-forecast, driving more sales can oftentimes be as detrimental as missing your number. So I think forecasting is the biggest skillset that salespeople need to develop in order to be ready for that next level as a sales manager.

The Percentage of Individual Salespeople’s Pipelines That is Remotely Accurate · [26:57]] 

Will Barron:

As someone with management experience and consulting experience, what percentage of individual salespeople’s pipelines are remotely accurate?

“18 to 20% of people are accurately predicting their business coming in. It’s the remaining 80% that are misses. And that’s precisely what I’m talking about, missing above can be just as detrimental as missing below.” – John Crowley · [27:13] 

John Crowley:

We have data around this and it sits right between 18 and 20%. So 18 to 20% of people are accurately predicting their business coming in. It’s the remaining 80% that are misses. And that’s precisely what I’m talking about, missing above can be just as detrimental as missing below.

How Can Salespeople Become Better at Forecasting Their Sales Pipelines? · [27:35] 

Will Barron:

Because I’ve never accurately predicted anything in this business, in any of my medical device sales roles, in the chemical sales before that. Other than it seems a waste of time for the salesperson because it’s not helping them make money, it’s helping the organisation. And as you alluded to the forecasting of the organisation to help with budgeting and cashflow and at the CEO level, kind of a publicly traded company, all kinds of important things are based on the back of that and the messages that they can say and whether they’re having a good quarter or a bad quarter or the share price is up. If it’s a sales based company, a lot of it will come from the individual sales reps forecasting. How can we get better at forecasting coming from someone who admittedly sucks at it and just guessed? In our CRMs there’d be, what’s your chance of hitting this? It’d be one to five. Well, three. Something [inaudible [00:28:20]. I don’t know.

“A lot of salespeople are very optimistic. And I think, unfortunately when you’re looking at a pipeline, you need to have a bit of pessimism. So, I think that’s where the sales manager’s job comes into play and that he or she needs to be really good at challenging those reps to say, well, how likely is this to close in the next 3, 6, 9 months, whatever it may be.” – John Crowley · [28:30] 

John Crowley:

Yeah. So that’s a tough question. I think… The reason it’s tough is because I think the personalities types that most salespeople are, a lot of salespeople are, is that they’re very optimistic. And I think unfortunately, when you’re looking at a pipeline, you need to have a bit of pessimism. So that character trait is not one that’s often found in salespeople. They’re more optimistic. So, I think that’s where the sales manager’s job comes into play and that he or she needs to be really good at challenging those reps to say, well, how likely is this to close in the next 3, 6, 9 months, whatever it may be.

How to Tidy Up Your Cluttered or Disorganised Sales Pipeline · [29:02]

Will Barron:

Because it’s a catch 22, right, of if you are pessimistic about your pipeline more, you lean on that side of the fence. Then your sales manager’s going to be hounding you of why you got the numbers that everyone else has. If you’re optimistic about it, then they’re going to kick your ass at the end of the year when perhaps you hit target, but it’s not the champagne popping celebration than what it should be. So, is there anything practical that we can do? And this is a legitimate question. This is nothing to do with sales management now. Is there anything practical we can do to tide you up your pipeline other than being slightly pessimistic?

“People that have been in this business for a long period of time, they don’t put anything into their pipeline until they’re highly confident that it’s going to close. And so they have found, unfortunately when you do that, you often will overachieve and that again will get you in trouble.” – John Crowley · [29:48] 

John Crowley:

I got to think about this. Is there anything we could do? I think… So, I will say Will, the one thing that I’ve noticed a lot of senior managers do, is that for a lack of better words, they sandbag it. So people that have been in this business for a long period of time, they don’t put anything into their pipeline until they’re highly confident that it’s going to close. And so they have found, unfortunately when you do that, you often will overachieve and that again will get you in trouble. But if your main focus is not underachieving or not stating that you were going to do more than you actually could, I think maybe there’s a little bit of playing it safe when you’re putting those customers into your pipeline.

The Benefits of Pragmatic Selfishness in Sales Leadership · [30:50] 

Will Barron:

That’s fair enough. And I think that’s a fair thing to say. We shouldn’t be punished for overachieving, but I would sandbag the shit out of my account so that I got a small target at the beginning of the year. If my target is 15 million quid and my sales manager knew that I was going to get four million from a big, massive theatre refurbishment at Leeds or Bradford or wherever it was, I would just lie about it and say it’s coming in a year later, which obviously doesn’t help anyone. So is there a way to put spin on this? If you want to get into sales management… Oh no, if you’re in sales management, do you have to be less selfish because that’s quite a selfish thing to do, right?

Will Barron:

If I sandbag my results like that, I don’t really care. The company’s going to me more money. I’m going to go over my sales target because my sales target is going to be small. I’m going to get a 10 million sales target rather than a 15 million sales target. And so percentage wise, I’m going to be far over. I’m going to be in the, say I get, 120% of my target. My commissions go up by double. It was something along those lines. To be a sales manager, do you have to take a step back from all that and be less selfish because you’ve got to get a team to win, for you to win, right?

John Crowley:

I think that’s a fair assessment. I’d say less selfish is a fair way to look at it. For sure.

Sales Leadership Should Not Be the Default Next Step For High-archiving Sales Professionals · [31:56] 

Will Barron:

Because I think that’ll put some people off. And if I’d have heard myself say that, well, I’d never wanted to go to sales management because I could see everyone going bald as they were kind of getting stressed and going through that process. But hopefully that’s put some people off because I feel, and tell me your thoughts on this if you agree with me, sales management seems like the default next step when there’s probably a lot more success that good salespeople could have by just sticking in the role.

“I think a lot of people move into sales management because they get bored. They stop challenging themselves, they stop being excited about the job.” – John Crowley · [32:05] 

John Crowley:

I think a lot of people move into sales management because they get bored. They stop challenging themselves, they stop being excited about the job. They become very pessimistic about the outlook on the job and they’re constantly… Because let’s be honest Will, this is one of the most devastatingly negative jobs that you can have. A good day is when you get one yes out of 10. That’s a good day, batting 10%? That’s terrible. Or a hundred. So, it’s a combination of things, but I think that you’re on the right track.

The Other Viable Alternatives to Going Into Sales Management for Salespeople Looking to Grow Their Careers · [32:40]

Will Barron:

Good. So with that said then John, we’ll wrap up the show with this mate. What are the alternatives to going into sales management? If someone’s listening to this and they’re like, ” It sounded like exactly what I needed.” And now we’ve just pulled the rock from underneath them. They go, “Oh no that’s sounds terrible. I don’t want to, I am a lone wolf. I am perhaps…” Like I am. I can be extroverted and introverted, but I tend to like spending a bit of time on my own. When I’m managing the team, it’s great to then get off the group chat on the phone, and then just work on my own in front of the computer. And that’s when I’m most productive.

Will Barron:

Whereas a true extrovert would probably be most productive running around, spending time out with the sales reps. If they had an office with people in there, mingling with people in the office and communicating with them. I get my best work done sat in front of a computer or on the phone with one person, and really gruelling down into the nitty gritty and the details of things. So for anyone like me, perhaps who’s more of a lone wolf from that perspective, what else can they do other than selling? Is there…? I guess there’s roles in sales enablement and things like that, but what other career paths do they have other than managing people?

John Crowley:

Will, I wouldn’t define a certain career path because I think as you talk to senior leaders and you ask them about their journey to getting to their current position, I think what you find is that very oftentimes they had a path that brought them through sales. So I think a lot of senior leaders can’t get to that next level, to this VP or the GM role, unless they’ve got that sales experience. So, there’s plenty of horizontals that you can go into, whether it be training, sales enablement, sales operations, whatever it may be, whatever that may be. But I don’t think that you narrow yourself down into one track or another. I’ve seen people from finance come into sales, from people from HR come into sales. And there’s no end to where people will come in from teachers, police officers. I mean, the people that you would have no idea would be good at selling, they find their way in sales oftentimes.

Will Barron:

So if someone comes in from HR to sales, what we’re saying is we can do the opposite as well. We can go from sales to marketing, we can go from sales to enablement, we can go from sales to training. Am I missing the point here in that, or as an industry, we’re too focused on going to management when there’s probably just as many opportunities horizontally across, especially a huge organisation?

“A lot of people look at a career ladder as if it’s just a ladder. I like to think of your career as more of lattice. And so, there’s times in your career where it makes sense to just go off to the right. It’s not a move up, it’s just off to the right. And that way you gain different experience, different perspectives that you just wouldn’t have had if you stayed just the sales role.” – John Crowley · [35:04] 

John Crowley:

Yeah. I think you hit the nail on the head because a lot of people look at a career ladder as if it’s just a ladder. I like to think of your career as more of lattice. And so, there’s times in your career where it makes sense to just go off to the right. It’s not a move up, it’s just off to the right. And that way you gain different experience, different perspectives that you just wouldn’t have had if you stayed just the sales role.

Will Barron:

And it’s a good way to wrap things up because that’s exactly what we’ve done, right?

John Crowley:

That’s exactly right.

Will Barron:

Good.

John Crowley:

Exactly right, buddy.

John’s Advise to His Younger Self on How to Become Better at Selling · [35:30]

Will Barron:

Well, I don’t know if anyone aspires to be you or I. Probably you more so than me, John, but that’s a good way to wrap up the show. And I’ve got one final question I’ve asked to you before. I’m going to ask you again. And that is, if you could go back in time and speak to your younger self, what would be the one piece of advice you’d give him to help him become better at selling?

John Crowley:

Believe in yourself.

Will Barron:

And do you believe in yourself?

John Crowley:

I do now. When I was young and new, I was petrified. I did not, then.

How to Train Yourself to Believe in Your Ability to Succeed · [35:53] 

Will Barron:

And how did you train that into yourself? Is this a habit? Was this a light bulb moment? How did it manifest itself for you, John?

John Crowley:

I think it was a little bit of both. It was habit and light bulb moment. But really, it was a point in my career where I said, you know what, you’re better than this. And you’re able to… Even though you’re talking to physicians who are much more educated than you are, you can talk to them at their level.

Will Barron:

That’s interesting. I always thought that. I’d never consider it perhaps the same level. But I always thought if there’s a piece of a pie of a surgeon’s, of a knowledged especially 56 year old surgeon, who’s killing it, and as I mentioned on other shows right local to me, there’s some of the best surgeons in the world, especially colorectal surgeons and low GI surgeons, I have the knowledge of 100th of a percent a sliver of that pie. And I could compete with them on all their endoscopy needs from the camera equipments, the lens systems, what they need for the procedure.

Parting Thoughts · [37:08]

Will Barron:

And I would often… And this is the teaching element of what we drive into the audience and hopefully they take on board that if you can teach someone just that tiny sliver of knowledge, people are going to pick up the phone to you. You’re not going to have to call, call and spam people and it changes the game. So with that John, I’ve really enjoyed the conversation mate. Tell us where we can find out more about you, everything that you’re up to and yeah, anything else you want to share with the audience?

John Crowley:

So you can always go to my website, which is knuckledraggingsales.com. But if you go to knuckledraggingsales.com/Will, I have a vacation checklist there that you can download for free. We’re coming into the holiday season where a bunch of people go on vacation, and I personally have been burnt by not properly preparing for my vacation. So, this is just a checklist that I put together for myself and I think it might be of value to your listeners.

Will Barron:

Good stuff. Well, I’ll link out in the show to this episode over at salesmen.org as well. And with that, John, we want thank you for your time again. As always mate, I really enjoyed this conversation, your insights, and I want to thank you for joining us on the Salesman Podcast.

John Crowley:

Will, it was a real pleasure. Thanks so much, buddy.