Anthony Charlton, Director, Gartner

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Anthony Charlton
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I was fortunate to be managed by Anthony at Gartner. Anthony’s team, the internally-famous RAT$ (short for Risk and Audit Team, not the animal), absolutely smashed their 2018 goal, which I was honoured to be a part of despite some severe discruption (scandal, even) in my own sales territory of South Africa.

At the center of all this was Anthony, who’s composure, professionalism, and commitment to great processes underscored the well-deserved success of the team. This interview has some fantastic insight into Anthony’s methods”

You can read Anthony’s full biography here.

Jamie: When you think about your career in sales to this point, what have you found most fulfilling? 

Anthony: I think what really drew me to this career was how it started off. I ended up in a sales role coming out of University totally by accident. What was fulfilling about it was getting exposure to senior executives at the world’s largest organizations from such a young age- at just twenty-one. I remember looking around and thinking about what my friends were doing and comparing it with my work. They had left University at the same time and had gone on to either work for law firms or gone into consulting organizations. Here, I was able to speak to the CFO of the largest oil company in the world. I think what was fulfilling about that was not only learning about those individuals and their organizations but also the fact that those people wanted to listen to what I had to say and engage in a conversation with me.

Jamie: I think a lot of aspiring salespeople can find it quite intimidating, talking to people at that level. What advice would you have for preparing for those conversations?

Anthony: I was extremely intimidated at the time having those conversations. When you start out, you always feel that you do not know enough or you are not the expert. Those you are talking to know far more than you in the field, but the key to overcoming that is being confident in the product you are selling, and the value it can bring.

The more confidence you have in your product, the more comfortable you will become, and the more confident you will come across.

In terms of preparation that is always key. There is a part of the preparation that you can do and you can control to help you navigate those conversations. Part of that is about understanding your product, the value proposition, and then understanding your customer. The more research you do, the better it is. 

But the research should focus not only on the company but also on the individual, and understanding that who you are selling to is as important as understanding their business. Anything you can glean about their experience, their personality type, and listening to how they have given speeches or how they write tells you a lot about the way they like to receive information. 

I think you can then flex your own communication to that, and that will go a long way to making it a more comfortable experience.  

Jamie: What is the best thing about being in sales?

Anthony: For me, it is the chase of the sale.

Ultimately, that is what we want to get to, but the bit that is the most exciting and perhaps the bit that I thrive off the most is the chase. Knowing that there is a contract out there, knowing that there is a deal out there to be had. The brainstorming and the creativity that you put into it to get it across the line is the most exciting part of the sale. When you get it in and show everyone, celebrate, and then you’re straight after the next one. I think it is the sort of build-up, and the chase element, that is most exciting. 

Jamie: What is the worst thing about sales?

Anthony: The worst thing is that there is no comfort zone in sales. It is never over, there is very rarely a point in sales where you sit back, and you think, “This is it. Now, I can relax. It is done.” You are always going after that next deal, and that can sometimes be tiring. That is where people become more stressed or feel the pressure.

The other bad thing is if you are not selling anything, that is an awful position to be in as a salesperson. It is when the deals are not coming through. Being able to get through those low points is a challenge, but that probably represents the worst part of the role.

Jamie: What is your advice for people to get through those times when the sales are not coming in?

Anthony: It is often about just stripping back to basics. When that happens to people, they become so overwhelmed by the big number or the big picture or the mountain that it feels like they have to climb. I think taking it right back to the beginning, back to the inputs that you need to get yourself up and running again, try to cut through the noise. Perhaps, relying on a couple of trusted individuals or a mentor whose advice you respect and listen to them can help pull you out of that.

The other is not to become too insular. That is also a trap that some salespeople might fall into, especially if they have been successful in the past. To think, “I have done this. I know what I am doing. I do not need advice from anyone. I am going to get through this.”

In sales, the environment you are selling into is always changing. You need to be adaptable, you need to be able to continually learn and improve, think about the economic environment, you think about macro factors that influence your consumers, you need to be open to learning and take note of feedback the whole time. That is crucial especially if you are going through a bad patch as a salesperson.  

Jamie: Why did you choose complex information-based sales? 

Anthony: Well, I guess this is what kept me in it. 

The complexity is interesting. It allows you to get to know the customer, the client, and the company that you are working with, at a greater level than it would otherwise. 

The kind of conversations you have with people who are at the top of their game, in very large organizations, is brilliant. You can ask them really interesting questions and hear fascinating answers about what they are doing and where they find their challenges. The satisfaction then comes in by being able to suggest how they could get better than that and them seeing the value in that conversation.

Jamie: What do you think about the guidance which Gartner or similar information companies sell? Is it recession-proof or at least recession-resistant? 

Anthony: What makes it different is the fact that it is not our organization writing about it. It is us listening to what peers, what practitioners are doing, how they are responding to the questions they are asking, and the solutions they are trying to formulate. In a time of crisis like this, it is very valuable to people where there is something like this on this scale that has never happened before. They are crying out to understand what people are doing and how they are reacting, which makes it very valuable. What is also valuable is how quickly we can turn that type of insight around, and then we can pull the network that we have in a matter of days to get that type of feedback and insight and get that all those real-time into the hands of our clients or out there into the market.

Jamie: If you were to find yourself job hunting, what attributes would you look for in the products that you would sell next? 

Anthony: It has to be something that you genuinely find interesting because you are going to have to talk about whatever product it is, day in day out. If it is something you don’t really care about or have very little interest in, then it will be a miserable role for you. I think it has to be something you have a genuine interest in that you can convincingly talk about. Why is it valuable? Why do you do that? What is your place in the organization and why you need to get better? Making sure you are driven to have that conversation with somebody and you believe in the solution is crucial whatever that product might be.

Jamie: What additional skills do you think are needed in the salesperson to sell something conceptual and intangible, compared to a physical product? 

Anthony: It is all in the questioning and being curious. 

It is all about how you connect a person with an intangible product. With an intangible product, you have to create or find a need, as it is never going to present itself – people think I don’t need that product because it is not a physical thing. 

It is intangible. You have to be very smart in questioning and discovery conversations. You have to understand where there might be a gap in the resources of that customer. You have to be smart in making the connection between that challenge or problem that they are experiencing and how that ties into the broader company setting, the broader corporate objectives of that organization, and then make the link from that to the product. It is potentially a deeper level of questioning you need, and you need that for them to be able to value-demo the products. With a physical product, you can value-demo it much more easily.

Jamie: You move from an individual to a role in a sales manager role. What additional skills do you think are needed to be a good manager compared to a salesperson? 

Anthony: You need all the skills that a salesperson has if you are going to be able to coach sales. What becomes more important is communication – that is probably the most important thing. It’s about making that shift to communicate. Communication is crucial, especially when you manage a relatively large team. The only way you can get your messaging, your coaching, and can motivate people is by connecting with them. It is important to understand the communication style of individuals on your team and then be able to flex that style to understand how you can get the best out of those individuals. That way, you create a good connection setting with the individuals, and you create a team culture as well. What is crucial is driving accountability within that individual, so they are accountable for what they need to achieve, but there should also be a sense of accountability to the broader team. You must build a culture. Once you have that, your job as a sales manager becomes a whole lot easier because there is a sense of drive and accountability that naturally happens without you necessarily having to manage it all the time. It is going to push it day-in, day-out.

Jamie: Can you give a specific example of accountability, which you have driven in your team?

Anthony: Not specifically. 

At the very base level, it is about sharing the number goal perhaps that the entire team is running for and getting people to strive to that. Lay that out clearly, be very transparent in what that number is and make it very visual. Whether you slap it on the walls or create some sort of visual representation, but it should be out there. 

Once we used the races and the number as a prize, getting people hyped up about it telling them that this is the one thing we need to win as a team. Having that sort of an incentive and the team buying into that as a prize can make the business spike across that period, and because of that, we really overachieved on the number. Whatever that milestone is – making it visual and also spreading the kind of messaging around it consistently creates the buy-in and excitement.

Jamie: What are the traits or behaviours that really successful people on your team display?

Anthony: We talk a lot about the will to win so wanting to succeed and wanting to do well and also acting upon that because you get people that want to win and they want to be number one. There are differences where you have people that will actually work hard for that and go ahead and execute what they need to do to be able to get there. To have that drive and that will is very important. The other trait is being competitive. That is something I always try to look for in people that are competitive and have that streak within them. Sometimes, some people listen to high-fiving or are loud and shout about themselves all the time. They just want to do well, and they want to win, and I think if they have that inside – that is probably the most important trait that sets apart those that succeed from those that do not.

Jamie: You have a fairly atypical personality type for a salesperson. What advice do you have for people who maybe have that same personality type of want to excel in a sales career?

Anthony: Do not be put off by it and look at other successful salespeople. There is no one selling personality type that succeeds, and it takes all sorts to build a successful team. It comes back more to the behaviours and the skills that you have. If you are curious, if you have good business initiative, if you do have that competitive streak, if you have that will to win, you can still be more. As long as you can use those skills and those traits, your default personality can be anything. 

Jamie: What skills do the first CEB and now Gartner emphasizes on? What do they teach that really makes a difference that maybe other organizations do not?


What CEB and now Gartner do well is instantly establishing a process in people. They teach a good methodology, a good process, and really hammer that home in the training and coaching that is given in the organization. A lot of people have left now; the feedback is often: “The training was excellent. I learned a lot from the organization on how to be good at sales.” It’s the process and ongoing coaching. 

What the training lends itself to is that the individuals are left wanting to learn more and wanting to improve, and that spirit of continuous learning and best practice sharing ultimately is our business. Individuals wanting to learn from the best in the company will apply what they hear, but ultimately it is underpinned by quite a stringent process that we teach and what we follow.

Jamie: If you want to get a job in a competitive organization like Gartner, what advice would you give for getting that role? 

Anthony: If it is an entry-level role, it is going to be about the business acumen skills, the curiosity, and then that comes across in how that individual would think about managing a conversation with a c-level executive. That is very important; it needs the different surety or a certain level of maturity, at least a sense of awareness and understanding of the type of environment that that individual works in, and how their function operates within the context of a large corporate organization, and the kinds of activities they are going to be engaged with. Being able to have a conversation at that level is really important. An entry-level applicant who comes from being aware of current affairs, understanding the business landscape, and being curious about business has an advantage. For a non-entry and senior role, it is definitely the same type of behaviours and skills, but trying to get as much experience of that as possible and being able to demonstrate that you have it, then it comes back to the idea of that “will to win,” the competitive edge where you have had experiences and where you have demonstrated that in your previous roles.

Jamie: Has anyone ever done anything in an interview that is really a wow-factor and said anything where you have to give that person a job?

Anthony: A lot of my interviews are conducted as a role play, and we get some fantastic candidates that come through and really nail the role play, and what is admirable in those role-plays is when someone just keeps ongoing. If someone can strike a balance between being not too pushy, but driving commercial outcome in that conversation, that is what really stands out. That sort of polite persistence. Someone who does that really well; that is impressive if someone can do that.

Jamie: Could you dive into a little bit deeper in terms of your advice, in terms of driving commercial outcomes?

Anthony: What you want to do is try to balance between a nice engaging conversation, and ultimately having an objective to drive the business. You are there to try and get a sale. 

If you can do that in a way that maintains that level of politeness, curiosity, interest, asking those questions, actively listening to the answers, and using that to drive to a commercial outcome, that is a real skill. Not losing sight of that end-objective is really important; whether you are trying to close in that conversation or not, it is about setting it up to get to that close at some point, and how you get to a stage by the end of which you are laying the foundations for that close. 

That is what is really important. In an interview, if you can demonstrate that in a half-hour role play, then that is really impressive and that is what we would look for.

Jamie: If you were looking for jobs, what elements of culture would you look for in an organization?

Anthony: It is all about the people, they recreate the culture. A company that has an environment where people have fun, and they enjoy themselves, and they want to learn and listen to each other, that is really important. You can see that quite clearly in organizations where people are happy to spend time with each other. If you spend so much time with these people, day in day out; you want to enjoy it. The other part is where you can see that high performance or good work is rewarded and there is a progression in the organization. There is a culture of meritocracy that those aspects are really important as well. 

Jamie: What advice generally would you give to aspiring salespeople?

Anthony: If you want to go into sales, you have got to be clear that is what you want. Sales can encapsulate so many different types of roles, and it comes down to the type of product and environment they are going to be selling in. One of the things that people often underestimate in sales is the pressure – it can be a lot of pressure. You have got to be quite strong-willed; you have got to be able to weather the lows that come with the highs. You have to be quite a strong individual to get through that because it is not plain sailing, it is not always the highs; you have got to be ready to take the ups and the downs. Along with that, often in sales, it is often a high-risk game, but there is a high reward too. If you excel at it, it can be a fantastic career.

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


I would have more confidence to ask questions to more senior people in the organization potentially, to reach out to them for advice, go to them for coaching, because looking back now, they would have been more than happy to have had those types of questions and being involved with helping with them.

Jamie: Could you tell me about a specific time that sticks out to you where you did not make a sale, or something went wrong, and it taught you something?

Anthony: There were definitely a few instances in the very early days being caught out through bad preparation mostly. 

At one point, we had a CFO resignation or a CEO movement which clearly has an impact on a C-level executive. 

I remember walking up to a live meeting and just not having read about this event taking place at the beginning of the week, which clearly rocked the organization, which meant that all the other prep was completely irrelevant to the conversation I was walking into. Not only is that incredibly embarrassing, but it puts you in the most awful position in that meeting. 

That is a hard way to learn to make sure you thorough preparation before walking into one of those situations.

Jamie: Then on the flip side, can you tell me about a time where you made a sale, it shows off the skills and knowledge you’ve developed throughout your career?

Anthony: One highlight was when I was an individual contributor, and one of the biggest deals that I closed was over half a million dollars, which for the product that we sell, this was huge. That, for me, was the kind of combination of what I learned as an individual contributor. It was a different kind of product that I was selling at the time where either you could have two strategies, you would go for the quick small sales and try and do that often, selling a few thousand dollars at a time, or you try and go further for a really big sale which would naturally take a lot longer and be a lot more complex, a lot of procurement negotiations, a lot of stakeholders to get buy-in from. I sort of went for that latter strategy that year. It was terrifying. It was probably one of the most stressful years I have ever had because it was all coming down to this one big deal which eventually closed. Once that had come through, then reflecting on, “Yes, that was the right strategy.” It was amazing being able to celebrate the elements that went into that. That was hugely rewarding and definitely a highlight for me in terms of the size of the deal, but also the strategy that got it there.

Jamie: What was the strategy to carry that deal through?

Anthony: There was a crucial conversation with the client where they were looking, and their feedback was, “Let us try out this. We will buy a couple of seats, a couple of licenses, which would have been a few thousand dollars, and then we will see.” At that point, making the decision, knowing the company that you are, the number of people you have, that we can grow this deal into something much bigger, would take months to close but making that decision then, and identifying the different stakeholders that would need to be engaged to grow that deal. We then map out what those conversations need to look like, to get stakeholders aligned, to understand what the budget conversations would look like, who were they be with, and finally the procurement, negotiations, and what that would look like. Mapping all of that out was the strategy, and knowing that it was going to be a long play, but being able to execute through those different stages, it was a remarkable experience.

Jamie: That was a risk versus reward calculation that you did?

Anthony: Exactly. It is high-risk, but if it comes through, I will be over my target for the year and done, or I have to keep chipping away at least a very small low reward, low-value deals, which will probably take as much work. Will it be as rewarding? Maybe not, so let’s try and go for the big deal. 

Jamie: Do you have a favourite story from your career at any point, the one you tell most often as an anecdote?

 Anthony: I have years that I look back on, and I think that particular year was an excellent year. My favourite year was the year when I had a team, the RAT$, with such an eclectic mix of people. We had age differences of ten years in some cases, different skill levels, but it all came together so well, it was a fun group and somehow it all worked out. It was a fun year with a great outcome.


Connect with Anthony on LINKEDIN

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