I have previously worked for CEB and then Gartner, two firms which sold Challenger methodology as a form of consultancy to sales teams. Challenger theory has had a huge effect on my own sales career, and I knew that I needed to interview someone highly familiar with the subject matter for enhanced credibility. Who better to approach than the Head of Sales, from the organization that now exclusively sells Challenger consultancy?

In addition to having a phenomenal sales name, Brett was very generous with his time, his network, and his insights in this seminal interview.

You can read Brett’s full biography here

Jamie: What have you found most fulfilling in your sales career thus far?

Brett: Well, I suppose it’s more professional these days. I am at the upper end of the age scale, and sales have probably moved from financial motivation and the ability to get overcompensated in the early days as a young individual contributor, to now seeing the sales role professionalized considerably.

It’s become a profession rather than a way to make a quick buck.

Seeing younger sellers come into the profession and seeing it become professionalized is quite rewarding because you realize that there’s a lot of science behind it now, which I think was always undervalued. It’s nice to see that it’s starting to become recognized that it’s actually an art and a science.

It’s not all about the guys wanting to run around earning as much commission as possible. There are people who genuinely believe in sales as a career and are becoming sales leaders.

It’s refreshing being able to encourage that and being able to develop and coach that. I think that’s probably where the most fulfilment comes for me now, is seeing people coming into a career they’ve chosen, not one they’ve fallen into, which is what you did back in the day when I ended up in sales. 

Jamie: How early on your life and career can you choose sales?

Brett:  I think anybody can end up in sales and choose sales as a profession within, let’s say, the first 10 years of their career. It doesn’t have to be the first thing you do out of university. It doesn’t have to be your first or second job.

I think you probably need to get into it in your first 10 years because I think if you don’t, there’s a risk that people have expectations that are not fair to someone who hasn’t accumulated that experience, and people expect that if you’ve done more than 10 years in the industry. I’d say that during the first 10 years of your career, anybody can step into sales at any point. I don’t think there’s a barrier to entry.

There’s definitely an expectation around qualification. I don’t think you have to be degree qualified but I think it helps to be degree qualified in a business degree because – depending on what end of type of sales you enter – the bit that people underestimate about sales is the amount of knowledge you have to have around customer understanding. Customer understanding is understanding their business and understanding business at a fundamental level. It doesn’t mean that you have to be financially trained. It doesn’t mean that you have to be technically trained in whatever it is that you’re selling, but you have to understand how businesses function.

Jamie: What are those key skills or bits of knowledge that people need to develop in the first 10 years?

Brett: Let’s say you’ve been in marketing or you’ve been in commercial contracting or some other business management function such as finance, I think if you’ve got a good breadth of understanding of how a business operates, and then you have an industry specialism – could be software, could be an engineering field, could be research, whatever, then you can probably combine those two elements to come in at the later stage because actually, that will compensate to a degree. But people will say, “Where’s your historical sales experience? Show me the last three years of attainment vs. goal.” That’s the thing you’re going to be missing, for someone who is 10 years in is going to have a certain salary expectation but doesn’t, unfortunately, have the “runs on the board” to point to.

Jamie:  You talked about the professionalism of sales and how you’re seeing more people come in with a college degree. What does that mean for those sales roles that were traditionally less educated? Does that mean that those roles aren’t going to be as valued or are going to disappear entirely?

Brett: Not completely, no. If you take transactional selling, the “less mature” sales if you want to describe it that way, the less sophisticated end of selling – transactional salespeople, or technical sales, or sales engineers, or people who are in technical industries who have often been apprenticed engineers and technicians that move into a commercial space. Often, they’re part of a field selling service. They come from service roles into sales, or you get people that are very good at transactional selling because it’s a commodity sale and therefore it’s a pure productivity game. They have to worry less about the professional element because if you’re a technical seller, you’re probably doing some of your sales support and it’s an individual rather than a team sport.

If you’ve got a field sales background, you can sort of gravitate into account management and I think that the problem is maintaining energy and productivity. If you’re let’s say someone who sells a low-value commodity that’s very transactional; I think you can learn a process and I think it becomes a more scientific approach to sales, which is, “How can I drive enough productivity to get the output that I need?”

I think where those role struggle now, if I take a Challenger lens, is all around how the customer environment’s changing.

It doesn’t matter how good you are at technical sales. It doesn’t matter how good you are at driving your own productivity and driving the volume if you lack some of the other skills that are needed now in a professional seller – the IQ-EQ mix, customer understanding, the ability to understand different communication styles, figuring out how a business ticks, finding moments to persuade, and moments to rely on process.

I think all these skills are trainable though. They’re the skills you have to eventually build in your armoury to start to become successful with longevity because you can’t just rely on, “Oh, well, I’m a technical expert in this particular widget, so I can go to someone who’s buying these widgets.”

Frankly, the reality is that businesses don’t buy from technical sellers anymore. They buy through procurement and procurement will just buy the way they want to. They don’t need technical sellers. If you are someone who’s a commodity seller, you are trying to drive long-term value; you’re trying to build contract value. Therefore, in reality, if you’re executing a bad message or you’re executing a bad sales pitch, then all you’re doing is just multiplying bad practice. There’s a professionalizing element; selling is getting tougher because buying is getting tougher. Buyers are getting tougher with us, but they are also finding it harder themselves to buy in an effective non-dysfunctional way. So we’ve got to, unfortunately, help them to buy now as well. Organizations like CEB, Gartner, and now Challenger Inc all talk about these trends.

Jamie: So when you start to talk about buying dysfunctionality, are you talking about the number of decision-makers, or the procurement process, or both?

Brett: It’s the increase in the number of stakeholders, more decisions going to a non-decision, more procurement people coming into the mix, more request to customize offerings but not necessarily recognizing the value of those customised offerings, and more price-based decisions. I would say pre-COVID, more status quo decisions were the issue – “I’ll just take what I’ve got now. I’ll do what I’m doing now with my incumbent, because you can try and drive as much value as you want, but the cost for me and the personal risk of making a change is far greater than the value that you’re offering me. I’ve got to go and convince these other 10 people, many of whom probably don’t even sit in the same department as me or even  the same country or the same part of the business, in order to buy something new.”

Jamie: What can an aspiring salesperson do at an early stage to prepare themselves for this rapidly changing world of selling?

Brett: There’s an element of humility and curiosity that is important early on, which is knowing that you don’t have the answers but also knowing that’s okay because if you show enough curiosity towards the segment, client, and business that you’re trying to target, you will overcome some of those initial fears that you have around, “I have to sell” and think more around it in terms of, “I have to understand this business and I probably have one call to do it in. As long as I offer something in return, then it’s how can I actually use that information to come up with a very strong response.” People call it a discovery call. That in itself is an art form. How do you discover the information you want when you don’t know what it is that you don’t know?

I think that’s why young aspiring sellers have to learn that failure is a part of the game. It’s a little bit like the start-up principal, right? You need to fail many times because you’ve got to have that humility and curiosity constantly in harmony. Because the moment you give up on the curiosity, you’re not going to learn about clients’ businesses enough to realize, “Ah okay, hang on, this business works like this. I know five other companies that are just like that, and I think I know some of their problems, and they’re quite similar. I think I can probably go in and solve some of those.”

If you don’t keep that humility going, then you’re going to constantly just bash your head against a brick wall trying to do the same thing over and over again thinking, “Well, it worked the last time, why didn’t it work this time?”

You’ve got to have that humility to say, “You know what? Maybe there’s something different here which I need to figure out. Maybe, it’s the stakeholder. Maybe, it’s the message I’m using or maybe, it’s the preparation I put in.” It’s that constant ability to self-diagnose what the problem might be.

I think if you have those two things coming in as a very inexperienced seller and then you have a good coach, a good manager above you, a good sales process, and a good structure, you’ll improve – no two ways about it.

Jamie: Are there certain personality types who are predisposed towards sales?

Brett: No, I don’t think so. I think Challenger Inc would probably say the same, and I’ve seen introverts become some of the best salespeople, some of the most sublime and successful salespeople you’ll ever encounter. I’ve seen extroverts crash and burn because they’re way too expressive and they don’t know when to shut up and when to listen. I think there is one thing that’s pretty consistent. There’s a certain resilience that you have to have. If you suffer knock backs quickly and easily and think that the world’s ended because you’ve had three people telling you to go away on a cold call or you’ve had a deal that’s crashed and burned, or you’ve “closed-lost” four out of the last five deals in the last week. There is a certain resilience that comes from confidence and experience.

It’s a little bit like saying what’s the right personality to be a buyer? Well, they come in all shapes and sizes, because they do. What personality type do you need to be a leader? Well, you can say there are some that are more successful than others, maybe “drivers.” Well, people become drivers. I’ve seen introverted people, quite analytical people, become drivers in terms of their communication style once they’re a leader, because that’s the responsibility they assume. I think you can learn communication styles that can help you overcome any less a personality limitation you may feel you have if you’re an analytic or an amiable.

That’s a lot of what we teach in Challenger actually – how do you use your communication style? How do you flex it within limitations to appeal to someone who has a different communication style to you on the buying side of the fence? Coming from Challenger, we’ve got a view on that which is; actually it’s not a relationship that you build, it’s the value that you build, and therefore, the relationship comes after building value. Even then the relationship is based on value; based on getting customers to think differently.

People used to say, “You’ve got to be gregarious. You’ve got to like people.” In reality, well, that’s true but don’t like people too much. Sometimes, they’re going to say no, a lot of times they’re going to say no and also sometimes you’ve got to be tough with them if you’re in a negotiation. That’s where Challenger would say – relationship builders or what we unofficially term “people-pleasers” actually struggle the most in sales.

If you’re a “people-pleaser,” you’re in the wrong game because sales is not about pleasing people. It’s about driving value and getting people to make tough choices.

Jamie: Does that mean all the Challenger skills can be taught?

Brett: I believe so. I’m a little bit of an outlier on this one in my own Challenger business, but I actually genuinely think Challenger skills were probably quite limited back in the 70s, 80s, and 90s because it was easier to sell back then. If you had a good product and there was a demand, you could sell it. Right price, right time, use a basic framework, budget, authority, need, and timing, you can sell anything. The high performance in the 80s was from people who did solution selling. They were the highest performers because if you work for IBM or Xerox and you’re coming in with these big complex tech solutions for companies that needed help, they do these great discovery runs using SPIN-type or needs-based diagnosis. That worked with you because that’s what you needed, so they were the high-performers. I genuinely think when the recession happened in 2008-2009, Challengers were born out of the recession – not only because the research found them back then but also because people had to do something quite dramatically different because budgets dried-up, and customers weren’t buying. You have to do something differently.

Before I joined CEB, I was running a small business and there were just two of us at the time. I was working for an Australian entrepreneur and we’d set up this new business in the UK right bang in the middle of a recession. We had this amazing technology in the green building technology space but no one cared. We were selling to fund managers, and no one cared, because they cared about the value of their assets that were plummeting and they cared about their jobs.

We ended up creating a Challenger approach without even realizing what Challenger was – we heightened the risk of inaction and made them realize what they were missing out, and how that was actually playing back into some of their own concerns, like occupancy of buildings, and whether the buildings are being managed environmentally correctly or not.

Then I read “The Challenger Sale” – that was already what we did. We did it because we had to do it. I’ve seen people in leadership positions say, “There is no way these people are going to learn these skills,” and actually learn them very effectively.

I’ll give you one very quick example. We went with a Swedish big rock and mining tool manufacturer from in Sweden, and they decided to run their pilot program in Zambia and South Africa. Their sellers were basically engineers, most of whom had been in sales less than a couple of years. They were ex-technicians. I remember thinking back then when I was working with our consulting team that this was a challenge, “Can we get these guys to be Challengers?” They were very immature sellers, very limited sales experience to actually learn Challenger skills, and we’ve had so many organizations say to us, “It’s too advanced for us. We need to get our basics right.”

Sure enough, we taught them, and they closed deals. They learned the skills because they used their technical knowledge and converted it into a business problem. We helped them build a message, that they were then able to go and scale across multiple customers. They preferred it because; “Hang on. What you’re telling is that I’ve got to tell a story that’s about a technical problem that can cost thousands or millions and it’s something that I can do 20 times, over and over again? Yes, absolutely. Fantastic.” It’s a teachable skill.

Jamie: Does that speak to the importance of the marketing function in creating great salespeople?

Brett: Yes, and no. It is important. There’s a lot that has been written around how marketing and sales have to be in parallel, like a team game, right through the sales funnel. Customers are going to go and learn themselves, remotely, more than ever and they don’t want to talk to salespeople, and their first place of learning about something is usually a customer or vendor’s website or somebody who’s an expert in that field; that is a great place to spark people onto a journey of discovery around and where you can place a Challenger-style message.

I think one of the problems you find in a lot of companies is marketing is quite separate from the frontline sales or from the business unit, so you don’t always have that luxury of getting them to help. What you’re really after is the individual sellers not having to do the hard work developing insights for themselves every time.

The sellers who fail are the ones who don’t have the EQ or the customer’s understanding and ability to build their own insights easily. The way that you make Challenger easier to learn as that you build the insights for them and that requires across-functional capability and effort.

Jamie: What trends in exceptional salespeople have you observed over the last 12 years since the original Challenger study? Is it still Challengers who are winning the game today?

Brett: If you look at the sales industry and tech companies that have gone from small middle-market companies to large enterprise, companies like Salesforce, their investment in sales professionals, sales tools, sales technologies, and sales processes is at an all-time high; and there’s massive growth of sales enablement.

CSO Insights, which is a research business, shed some data last year or this year that showed that something like 50% of companies with over $500 million turnover have a sales enablement function after 2016. Before 2016, it was something like 10-15%. That’s a massive growth in sales enablement, which is helping to professionalize the frontline, the sales processes, and all the tools that people have. But there’s also a lot of people entering into sales teams that are given the tools and the support mechanisms and everything they need to go and sell but they haven’t figured out yet how to put it all together.

People are saying, “Is Challenger even relevant anymore? Does there need to be new methodologies?” If I were going to put a bet down, I’d say, “I’d rather trust a methodology that was an anti-recession methodology last time around because it probably has some of the answers for the current state situation.”

The challenge we have now is that the status quo is not the problem. Status quo has just been blown up. People have to do something. They’re at a risk of going under. They can do nothing if they dare, but they can’t do that for long or they have to do something, they have to do it very quickly. We’re using Challenger methodology to say, “You need to make sure that you make some good choices.” We highlight the risk of making false choices or bad choices. I think the premium on sellers now using their customer understanding piece is at all-time high. Not only having customer empathy and understanding, but also the ability to switch it to being assertive, when required, but in a good way. You need to use whatever skills you want to drive value, urgency, and drive momentum, and overcome what are going to be even bigger purchasing hurdles.

People are still spending money, but they’re spending it on projects that need to happen right now. They’re stopping long-term projects, the supply chain shock and impact is all over the place. I just think a seller now, tenure, or untenured is going to have to really lean on those empathy skills and then the ability to actually have the confidence to drive forward with a solution.

Table stakes have just risen because I think previously you had to go and find demand. Now, we need to start driving demand again and driving demand is tough. This is what separates the best performers from the rest of the pack. That’s where you have to go and put your skills to the test.

Jamie: What elements of a sales culture in that more difficult environment will make a sales organization successful?

Brett: If we’re talking culture versus environment, culture takes years to build, environment is the one you can create relatively quicker. It goes back to the CEB research on culture which I really believe in. You need to have structure. You need to enable sales skills. You need to provide the tools and allowing some autonomy and freedom of expression if you want to call it that. It goes back to what I said at the beginning – be prepared to fail. Well, the environment you should create as a leader and as a company is, “It’s okay to fail. Go and try some stuff.”

Maybe not your strategic account managers who have the biggest crown jewels of the accounts, because you hire different people for that, but in terms of traditional frontline business development sales, you’ve got to be prepared to try stuff and you’ve got to be prepared to fail and you need to encourage that, but you can’t allow that to go on forever because you need to see incremental improvement.

I think that’s where you’ve got to create a balancing act, between the structure, a good sales process, some good enablement tools, resources, and a good set of frontline managers who are comfortable coaching to that level of sellers expressing their freedom. Because you’ve got to try things, otherwise, if you tell people how to sell, they are never going to learn themselves. You’ve got to encourage that creativity because that’s how people build their instincts, that’s how people build their experience. But they’ve got to have that ability to feel that they can do it safely, but eventually have some structure, and some guardrails.

Otherwise, it’s the worst thing. I’ve seen this happen in medical devices. I’ve seen it happening even at our business actually. You let people go on for too long, sort of get lost in the wilderness and then all of a sudden, the carrot disappears in the stick comes out, and you’re nine months into a long sales cycle, and you realize they’ve been spending nine months going in the wrong direction. Well, you’ve got another nine months in that long sales cycle before they’re going to get it right. It’s on the company to make sure they stop that individual from getting lost for nine months. You’re going to have freedom but it can’t be unlimited. 

Jamie: How do you look for those traits of an organization from the outside?

Brett:

I suppose if you go on LinkedIn you can see how their leaders talk. I think when you see sales leaders on LinkedIn celebrating their people and celebrating good ideas, that’s the level of leader you’re looking for.

Glassdoor is a tricky one because it’s such a mixed bag of stuff on there and you can’t filter it for sales culture or sales environment.

I think when you’re going to the interview process, there’s definitely questions you can ask around – “What sales process do you run and what tools do you provide?” That’s a double-edged question because you want to hear something, but if they tell you they’re on their fifth system or fifth application by the time they get to the end of the sales tools list – “We’ve got an eight-stage sales process and we’ve got really strong checkpoints at the end” – then you know probably that they’re quite an autocratic sales organization that’s going to be really rigid around the sales process.

But if you hear someone has no sales process, “Oh, that’s fine. You’re your own boss.” Great, that’s very liberating. But what is the sales process? “Oh, no, we don’t have one. It’s like, go and sell. We give you a number. We give you a car and some keys. Off you go.” That’s the other end of the extreme where that should also send some alarm bells going because I think no matter how good you are as a seller, you need sales enablement. You need tools. You need a sales process because anybody who says they don’t have one has probably not done the job for a while, or if they have, they haven’t been very successful at it.

Jamie: Going back to a point you made earlier, why is it so difficult to come into sales as an older aspiring salesperson? Is it a young person’s game?

Brett: If you are relatively younger, and if you turn to come in on a much lower base and you buy yourself some breathing room, compared to someone who’s usually been working for 10 years; they have to come in at a higher base. Those roles become harder to find; true sales roles. I think that tends to be a bit of a barrier to entry sometimes for people who have been in their careers for longer than 10 years. But I think we need to be open to people switching.

Jamie: What’s the biggest piece of advice you’d give to aspirational salespeople?

Brett: I’ll give you a great example. We’ve had to make some redundancies recently sadly because of COVID and I had a guy who was on my team. He was literally coming into the role as we made the redundancies, but this guy ended up getting three other offers in the space of a month. One fell through and then ended up taking another job again. He was smashing it with offers because he approached the job application process the same way that he approached a sale; he didn’t just send his CV out. He cold-called sales leaders to pitch them his CV. He treated the job-hunting process like a job, and he used his understanding of sales.

If I think back to when I was a hiring manager and was most impressed with people, it’s the ones who have had the courage to  ever-so-slightly bypass the traditional recruitment process once they know that you’re the hiring manager, and make a direct outreach that’s delicately done, like well-worded, shows intelligence, shows eagerness, doesn’t pressure, doesn’t keep pressuring you or pestering you, but shows that they are definitely interested.

There’s real intent. There’s a desire to show that they’re proactive and assertive because that’s exactly the skills that you want to share with a client. I even had HR managers come to me and say, “Hey, this guy, he leapfrogged the process!” I’m sorry. I want this guy or this girl in the process because that’s exactly the skills that I’m after. Now after me ignoring them for a day or two, if they pestered me with four phone calls and three emails and they’re not taking no for an answer – which by the way has happened before – then it swings the other way. Then it’s like, “Get rid of them. I don’t want them doing that with my clients.”

I think the best salespeople I see now, if I think back to the people I’ve hired and really enjoyed working with, are the ones who are completely open to coaching. They go back to that humility and curiosity thing again. They find a good coach and a good manager. They take good coaching and use it and be prepared to fall over and make mistakes. For me, an aspiring seller needs to enjoy the ride but accept that there’s going to be some awkward moments along the way.

Jamie: If you had your sales career again what would you do differently?

Brett: I wish I was using Challenger back in the 90s. If I think back to all the clients that I got stuck with and got stuck in RFP processes and sold to at a ridiculously low margin, I think I would have been a lot more intelligent about how I thought about my clients’ businesses, learn what I needed to learn and then scaled it because I think that stuff is what gives me fulfillment. I see others getting fulfillment when they close a deal that comes from their hard work where they’ve created interest with a customer who had no interest in what they were doing.

They didn’t even know you existed, but because you started that process and persuaded them that this is something that they need, because they had a challenge in their business that they hadn’t figured out how to overcome, or that they didn’t even know about or hadn’t thought about fully. That’s the most rewarding thing for me in sales. It doesn’t matter what the dollar value is. It doesn’t matter what the commission check attached to it is. That’s the fulfilment part, that I’ve used my craft to improve someone’s business.

I think that is what I try and inject into young sellers now, I say, “Don’t worry about the deal value. Don’t worry about the dollar size. Don’t worry about the commission check. That will come.”

You need some of those Challenger deals early on and you’re going to be hooked. You’re going to want to get better, rather than seeing it as a job of, “How well can I forecast and how long can I keep the manager off my back, or when am I going to get this deal landed?” That stuff will just go, that stuff melts away if you can get your approach right and your real enjoyment comes from engaging a customer at their level.

Jamie: Would you choose to create those own insights rather than have a company that supported you by creating them for you?

Brett: Well, obviously, I suggest you use your company to help. But no, I think it’s all transferable.

I think an aspiring seller who comes into any sales role has to sit back and understand what is it that we’re selling, what problem are we fundamentally trying to fix here, what does my client think about that, do they care and does it matter? You’ve got to get all of those things, line them up and if you can’t line then up, then something has to change.

You either have to change jobs. You have to change the product, which you don’t control. You have to change the message, which you do control, or you have to change the way the customer thinks about their own business, which you can influence – you can’t control, but you can influence. That’s what it’s all about.

I think if you do those things, you realize that if you scale and repeat that process enough times, you can be highly effective. You can earn a lot of money. You can be a true professional. Then, I think the thing that you have much more in sales organizations now than ever before is that there is a true career path now.

Whether we like it or not, whether it’s the right answer but the high performers get awarded with manager roles once they’re ready to do management jobs. They have got to learn not only to do the imparting of wisdom, but also do the coaching bit as well, which is helping sellers to actually benefit from their own skills, not just what you know and can teach them.

Then, I think if you get into sales later roles, if you look at CEO roles, more and more of these guys are coming from sales now. 10-20 years ago, they were coming from marketing. If we go back to 30-40 years ago, they came from finance or accounting or maybe engineering. I think the most aggressive new companies, these guys are salespeople.

[End]

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