Felipe is one of the best people-focused, empathetic people managers I have met, making him a key former colleague to interview. As usual, Felipe was organized – having replied first via email with his answers to my question, which we reference throughout the interview – and enthusiastic; not to mention  generous with his time and insight.

We touch on how to measure culture, the characteristics of a great leader, and why career loyalty can pay off in this short but poignant interview.

You can read Felipe’s biography here

Jamie: We’ve previously talked about the transition previously from being an individual contributor salesperson to managing people. In terms of that transition, what preparation did you do to be ready to be a people manager?
Felipe: I managed people in relationship management before I did it in sales. In reality, you don’t get any training, it has to do with whoever gives you that role the first time, to think that you possess the kind of inherent qualities to be able to manage others. I think at that point, it’s not even so much about getting the best out of them, which is what is required as you move up as a manager. In the beginning, it is more about just not breaking anything too badly.
When I started managing people, I was 27. I think for someone who gets that job at 27, you’re probably best off at least being perceived as someone who can emotionally manage other people, who can manage the process, and who can manage administrative stuff. Being a safe pair of hands is the quality that’s first looked at for someone who is given the responsibility of managing others at a young age. The expectations obviously change over time. For example, now I’m going into a role where there are several explicit challenges and priorities. The idea is to get the best performance that you can out of every individual that you’re managing, but I think that comes with time and responsibility in those roles.

Jamie: What advice would you give to people making that transition?
Felipe: To be given that trust, I think it is important to always conduct yourself as someone where the buck would stop, meaning someone who will never let things fall apart. When you don’t have that responsibility, like in a single contributor role in sales, worst-case scenario, you don’t sell.
There are plenty of opportunities to display a sense of responsibility. I think that for someone who wants to go from single contributor to a manager of salespeople, you need to take advantage of those opportunities to showcase that. It’s also a bit of a frame of mind, right?

Jamie: What are the traits you really admire and look for in the person who’s going to manage you?
Felipe:

I don’t think you can work for very long for someone that you don’t, at some level, admire or that you recognise that they have better attributes in some ways than you do. That is professional but also personal, I don’t think you can hate someone personally but admire them professionally.

There has to be a good balance, and some of it can be covered by experience, and some of it can be covered by natural ability. Again, drawing from a most recent example, I’ve done a lot of interviews with the company that I’m joining. I like the company, I like the business, I like the opportunity, and I like the corporate stage they are at. But the reality is that the most important part of my decision was taken was when I first spoke to and later met the person that I will be reporting into. He’s got tons and tons of experience, but he also phrased the need for my role as being a partner in Europe for him. Someone that wants to work with you, and who was very open to the ideas that I was suggesting.

There’s an element of admiration, a feeling that you’re going to learn something from them, because otherwise…I mean, you can do it for a short period for the role itself, for the content, for the money. But once you’re done learning, you probably have the inclination to move on. If you don’t, then you will feel like; eventually, you will, and you will feel like you’ve wasted some time before you did.

Jamie: You mentioned that you would like the job to be good enough, and fun enough, that you wouldn’t want there to be a stereotypical “work-life balance?”
Felipe: I don’t mean that work needs to get into personal life. What I mean is that personal life needs to get into work. I don’t necessarily mean it as work occupies everything about who you are, but inevitably, it kind of spills over. If you are respected, confident, and smart at work that spills over into your personal life. I think it’s important to bring the personal into work as well. I don’t believe people are wired to be one person outside of work and one person at work.

I feel a good manager should be someone that creates an environment where everyone feels that they can say anything in any room, no matter how stupid or smart and that there’s no judgement. A lot of this self-confidence comes more from personal characteristics than professional ones. I think that it’s important to let people be themselves at work.

Jamie: As a manager, how do you go about helping people feel comfortable, being confident of speaking out without judgment?
Felipe: I don’t do it in a very strategic or conscious way, but I think that people take their manager’s example as the line of what’s acceptable or what’s appropriate in terms of behaviour at work. For example, my most recent manager chose to be very open about his mental health, which made it ok for everyone to talk about their own. I am always very open with my sales team about my shortcomings as a salesperson when I was a single contributor. Not because I want people to tell me how terrible they are at this or at that but because the idea is to have an environment where we can be open about our weaknesses or vulnerabilities. If we can do that, then we can do something about them.

Jamie: You mentioned that you have just gone through an interview process, and determined the specifics of a culture rather than generalities. What sort of questions would you ask?
Felipe: I think more important than the questions are the answers.

If you ask a question and you feel like people are holding back or just giving you generalisation, then you kind of have to probe into what they’re saying; what do they mean by “management are really approachable,” or “it’s a really flat structure,” or “ do people enjoy themselves together outside of work?”  I think if a company has a good culture, they will probably take the opportunity to answer the question with a lot of very specific stories or examples of their most recent shared experiences which define who they are. If they have nothing else to say, maybe it’s because there is nothing else.

Some people, especially younger people, it’s almost like their go-to question when you ask in an interview, it is always like, “What is the culture like?” I guess in sales, there will be some people who are looking for a specific, very competitive sort of culture, some other people would be into a collaborative team-based culture. I think it’s important to ask the question, but I think it’s more important to know what you want as an answer as well and probe further if you are not getting to hear what you want.

Jamie: You mentioned the term “landing zones” relating to negotiation. Is that from a course or training?
Felipe:

Actually, it’s from the Brexit negotiation. It means that in any deal there is a landing zone of what’s acceptable for the buyer and the seller. The objective is to try and define, through qualification, what the zone is. Then you try to land as close to the edge of the buyer’s zone as you can, rather than close to your own edge.

Jamie: That must involve a lot of preparation for the negotiation and the follow-up in terms of making sure you understand that and are making the right proposals?
Felipe: I think with enough experience, you can eventually identify with less information where that zone is and what you can aspire to achieve.

If you’re conducting qualification directly, whatever information you elicit from the buyer through the process is what will help you define what that looks like. Sales experience probably helps you achieve a slightly higher price at a slightly faster speed.

I haven’t done a lot of directly selling myself over the last few years, but I get involved in a lot of deals by supporting or advising my sales team. I feel that’s where experience shows more clearly, that you are perhaps able to anticipate how a deal is going to play out, what might be the objections or the limitations that might come in front of you, and how you overcome those. You should have the answers ready. Over the last few years, I think where I’ve added the most value has been in helping close deals, or in some cases where I’ve helped achieve slightly higher prices and slightly faster turnaround times – by understanding how these deals typically play out.

Jamie: What advice do you have in terms of as a manager for defining sales territories, and as a salesperson, for making sure you have a good one?
Felipe: Through interviewing salespeople over the years, I have seen a lot of candidates whose main reason for leaving roles that otherwise seemed perfectly acceptable, was that they had been let down somehow by an incentive scheme which had a moving goalpost, or their manager ruling over something against them when they felt it was unfair. It often has to do with the sales territories. Some companies deliberately set up incentives and competition so that, for example, if something has not been touched on Salesforce for a month, then anyone can go for it.

I have always learned to define the territories well and try and decrease the amount of friction. There are always going to be outliers, but the idea is to try and set it up as clear-cut as possible and never reward someone who goes after something wrongly. Now, the difficulty there is to get people to perform well since the competition is not necessarily against each other.

From a manager perspective, the idea is to try and set up territories which are as comparable as possible so that the KPIs can be the same and then you can compare people as if they were Formula One drivers in the same team. The reality is that that’s very difficult to affect, especially in Europe where you have language specialists looking after certain geographies and such. But as a principle, I think that’s appropriate to try and strive for.

In terms of getting a good territory, it’s difficult to say, if you’re talking about someone who is in an interview trying to get offered a role. It’s almost impossible to negotiate in that context because you have very little leverage, and your primary goal is to get the role. Once you are more established into an organisation in terms of improving the territory, then it can be done.

It can be persuasive if someone comes to their manager with numbers and information about why someone’s territory is more rewarding than someone else’s, but the reality is that most people don’t have the ability or the interest to go and run that data from the CRM. However, if someone comes with data on that sort of front, from a management perspective that’s the kind of case that I would react to – it would prompt me to do further analysis.

Obviously, as a manager, you always put a lot of effort into making sure to behave and to be perceived as being fair. I almost always decline to rule over something arbitrarily. If someone has a good case, I guess, it prompts you to look into something further, and if there are scientific reasons for something, then you can explain. At the end of the day, the territory is one big pie, and if you are to cut it from someone and give it to someone else, you need to have a good explanation. Otherwise, you’re pleasing one by displeasing the other, as a sales manager you do not want to spend any time doing that sort of thing.

Jamie: I think of you as someone who’s been exceptionally career loyal. Is that something you would recommend for an aspiring salesperson versus jumping around and trying other things?
Felipe: It depends what’s the goal. If it’s purely financial, I think there’s a statistic that says every two-to-three years, if you move companies, you get a higher base salary. Everyone has individual circumstances, but I don’t think the financial element alone cuts it, because you can get paid handsomely without having to compromise on things like culture. It’s just not worth it to do something that makes you unhappy.

I don’t regret at all my loyalty to Acuris, I found a way to move around a lot within the business and I had seven or eight roles over 12 years.

My earnings were obviously not maximised, but I was rewarded appropriately. I’m taking a larger pay rise by moving companies than if I moved internally again, and that probably shows that I was slightly underpaid. But it also gave me the ability to participate in something more like a journey; in something that gives you satisfaction on a multi-year basis. I was a small shareholder in that business, which felt like it was worth more than its monetary value or the monetary value of jumping around. I feel that if you find a good company, in my experience, it’s worth extending until it’s time rather than just moving for the sake of slightly better pay.

From the experience of seeing people in interviews, when you see someone who’s done five or six jobs in 10 years, there’s something not convincing from the start, right? I don’t want to say they are mercenaries, because sometimes people have to find their best way to make a living, but there’s something unattractive about those candidates.

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