Culture Over Tactics: Richard Cogswell’s Formula for Sales Success
3 Mar 2025 · 28 min
This podcast episode (March 2025) features host Kwame Christian interviewing Richard Coxwell, a Singapore-based sales leader with extensive Asia Pacific fintech/payments experience. Coxwell describes his shift from top-performing individual contributor to sales leader and argues for prioritizing culture and mission over short-term sales tactics. Key topics: building psychological safety and trust, managing difficult conversations (including letting toxic high-performers go), delegation and making leaders redundant, aligning cross-functional objectives, hiring for cultural fit, and planning a 3–5 year growth horizon. Coxwell also discusses his book, The Cultural Sales Leader: Sustaining People Attaining Results, and provides contact points (LinkedIn, richardcogswell.com). The episode contains promotional ad reads for the American Negotiation Institute and the podcast’s premium offering.
So you don't even have a basis to start with, apart from your competencies, where you perceive you might be good, how you might. You know, in my case, I've always considered myself a bit of a servant leader. So, you know, I was trying to convey to others some of those NINJA sales tactics that you mentioned at the beginning because that was all I could do. Right. So, yeah, absolutely. It's unfair in many ways that this is the way that it happens. And sales is not taught in school, it's not taught at university. It should be. Right. And equally sales leadership should be as well. So that's what I'm effectively, what I'm trying to do is write the book that I was looking for at these three stages of my sales career. Right. And couldn't find.
Incredible. Yeah, Rich, I'm, I'm following. I, I agree 100%. And it seems like if we're going to encapsulate these challenges, one way to think about it is when you are an individual contributor on a sales team, your primary function is to sell and negotiate externally. But now, as a sales leader, your primary function is selling and negotiating internally within your team and within the cross functional apparatus of the organization. Hey, I'm Kwame Christian and you are about to step into the world of Negotiate Anything, the number one negotiation podcast.
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Rich, thanks for joining us today.
It's a pleasure, Kwame. Thank you so much.
Yeah, it is our pleasure. So how would you get us started? By telling us a little bit about yourself and what you do.
Yeah, sure. So, Richard Coxwell. I live and work in Singapore. I've been working in the Asia Pacific region for the last 12 years. I spent 85% or so of my career in what I would describe the sort of nexus of payments data and technology. So the payments industry, essentially B2B solutions, typically around Accounts payable payments. Currently a card issuer working in a fintech firm. So I issue virtual credit cards that primarily solve for paying suppliers in the travel industry. So it's you know, multi billion trillion dollar business but you know, servicing var across Asia Pacific.
Amazing and rich. Little birdie told me you might have written a book recently. Is that true?
Yeah. Yes. So it's funny actually. I was talking to a friend of mine who I used to work with, salesperson who's in one of my teams back in the day and he said it was no surprise that I'd written something. I found it a surprise, but this book kind of had to come out of me. It was a bit like a chest burster alien style. But yeah. So I wrote this book called the Cultural Sales Leader Sustaining People Attaining Results. And really I guess it's the culmination of my learnings across my sales and then sales leadership career. And you know, I've had a very normal trajectory in that sense in that I was a single contributor. Firstly promoted with no training, then you get some experience and then you're typically asked to come and turn around a situation that might be dysfunctional or not performing. And I've also done that sort of ground up work where I've been the guy on the ground. You know, I've built a customer base and then I built a team around it. So I've. What I've tried to do is encapsulate my learnings and practices in what I hope is a very human and practical way. But to look at it through what I think is the greatest catalyst of all, which is putting fusing your people to a mission that is ambitious, that is aggressive in the marketplace. But it's culture, it's the paradigm of culture that can turn something that is good into something that is really transformational.
What I love about this is that we, with this approach that you captured in your book, you didn't focus on the ninja sales tactics that you use to close all these deals.
Right, Right. You started at maybe that'll be another book that'll be book number two.
Right. You started with the team, but not just the team, like the ethos behind it and the culture you're trying to create with the team. And a lot of people will start with the tactics. All right. This is the tactic that you use in this situation to overcome objections and make more money, drive revenue, those type of things.
Sure.
I want you to really sell this to us because there's the other approach where it's just focused on the Tactics, the strategies and closing as many sales as possible, which has its place. Why did you choose to start here with the culture of the sales team?
See, because. Okay, so where I come from on this is what you've described to me is what each individual contributor should be expert in or developing their expertise around. Right. But what annoys me, if I'm honest about it. Well, let's put it this way, what am I in opposition to? I'm in opposition to companies that don't have a go to market plan. And that's more of, you know, you'll find that more often than you realize. And you know, I was noodling around about this and a lot of this again comes from that typical trajectory because I remember when I was lifted up to sales management, I right from being the best salesperson in a particular group at the time. And there's this sort of conferred wisdom that you know, you're brilliant at that you're the ninja salesman, as you say, you're going to be an outstanding leader. And that's just not true because it's a very different discipline. Right. And I think what that tends to lead to is that kind of where you fall back on what you know. Right. So you're more likely getting busy, right. And driving those kind of individual contribution type of outcomes and behaviors, but you're probably less capable of A bringing a team together and B, sort of questioning what went before and creating a better pathway for better outcomes. So my point about this is that, and it was, it was true of me, if you're living financial year to financial year, which happens in a lot of sales organizations, right. You come to January 1st and you're given a mountain to climb again, right. Every time the chances are you're not going to change that because you don't know any different. Right. But with experience, I guess gained on the journey and obviously you learn from others and hopefully you meet some great leaders on the way. There is a better way. Right. And that's where I'm trying to really put across something that's very practical in the sense of, okay, how do you go about the job of being the detective to find out what you need to focus on in your company? How do you fuse that together into a mission? How do you articulate that across cross functional groups and bring everyone on a journey to some something that just aligns everyone because you bake it into the culture as compared to, oh my God, this financial year we either hit, we miss, oh, we gotta do it again, right. With no real structure do you know what I mean?
Oh, yes, I think. Tell me if this analogy lands. It's kind of like you're playing a sport and you're the best player on the team. And then the management says, you know what, now you're the coach and so.
You'Re coaching the team and then things don't go as well. You're like, you know, what team? Give me the ball. Yeah, give me the ball. I'm going back in. Yeah, right.
And so it's a completely different set.
Of competencies that you need to coach.
And lead a team versus being a star player on a team.
And no one equips you for this, right? Because in fact, all of your relationships have changed, right? Because from being a member of a team, suddenly your relationship with your colleagues has changed, right? Because they want to know what you're all about as a leader now. And there may be difficult dynamics within that. You suddenly have to manage your leadership, right? And I remember it took me well over a year in this first managerial position to even have the confidence to ask for investment in my leadership growth journey. Because, you know, day one I felt I had to prove something, right? They promoted me, right? So now I've got to go prove that I'm good enough. And it took me, as I say, a good year. And a bit before I was in a position where I was like, okay, listen, I've delivered X, Y, Z, but I can see weaknesses here and I need to develop in these areas. Here's a return on investment if you can put me through, you know, some training. It's not just that either. As you say, you've suddenly got cross functional areas who are all part of the mission to win and secure and keep and build business, right? But often not totally aligned because those leaders have their own objectives. And it's not again, typical for the sales leader to go and align. These are our objectives. This is how we can marry the two things for best advantage. Do you agree? Do you not agree? So absolutely. I think that analogy of suddenly becoming the coach and you suddenly have to deal with tactics and by the way, you'll probably go and try and find the previous coaches tactics and you probably won't find them because it hasn't been written down anymore, right? So you don't even have a basis to start with apart from your competencies where you perceive you might be good, how you might, you know, in my case, I've always considered myself a bit of a servant leader. So, you know, I was trying to convey to others some of Those NINJA sales tactics that you mentioned at the beginning. Because that was all I could do. Right. So yeah, absolutely. It's unfair in many ways that this is the way that it happens. And sales is not taught in school, it's not taught at university. It should be.
Right.
And equally sales leadership should be as well. So that's what I'm effectively, what I'm trying to do is write the book that I was looking for at these three stages of my sales career. Right. And couldn't find.
Incredible. Yeah, Rich, I'm, I'm following. I agree 100%. And it seems like if we're going to encapsulate these challenges, one way to think about it is when you are an individual contributor on a sales team, your primary function is to sell and negotiate externally. But now as a sales leader, your primary function is selling and negotiating internally within your team and within the cross functional apparatus of the organization.
Yeah, I'm so glad you said that because it's so true. And if you're not selling all the time, then you're not going to be totally successful. Right. Because at the end of the day, you've got to sell the vision to your people. And a lot of this is also about to my mind, as you gain experience, it's about narrowing the aperture, narrowing that lens of focus so you actually do more. Again, so many sales organizations, because of the pressure of numbers, you find you've got people shooting for everything, whether it's good, bad or ugly. Right. And the amount of times that you find salespeople who are celebrated just because they do deals, but the deals they do don't always turn into profitable customers is also extraordinary. But that also tells me that there isn't a sales plan or go to market plan underpinning that. And yeah, you've just got to find a way of getting out of that sort of in the trenches, day to day focus, which again is a danger. Right. Especially when you're newly promoted because people want you to fix their problems around specific deals and what have you. And you've got to find ways to free yourself of that as well. You know, you've got to say you've got to be able to change the dynamic. What I speak about is behaviors create culture that lead to results. And instead of getting down in the weeds and in the trenches all the time, which prevents you obviously of thinking, you know, what your new horizons might look like, you've got to kind of push things back on people, which is not, say, don't escalate, but it is to say, who have you spoken to before you've escalated it to me. What do you think the solutions are? Right. What do you think we should do now? Of course, there'll be times where you do have to solve for something pretty sharpish, but if you're throwing that back on people, you're conferring on them the requirement to think creatively about their business and therefore the business. Right. So that's also a lot of where I'm trying to come from on this.
Hello, my friends. Before we get back to today's episode.
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Yeah, I think it's interesting, I often think in terms of, you know, what a strange term a sales team is, because quite often it's a group of quite distinct and powerful individuals. Right. And within that as well, single contribution can have a very positive connotation, it can have a very negative one. Right. And you can certainly find people who are so focused on going and getting the kill that they don't care about the collateral damage. Right. And two things strike me in your question. One is becoming suddenly good, competent at having difficult conversations with people, which could be about performance, it could be about behavior. Right. And also how sometimes I reflect on the fact that, you know, on a couple of occasions, more than a couple of occasions, you sometimes have to let what you know, the person who on paper is perhaps the one that is celebrated but for the wrong reasons, and you sometimes have to let those people be happy somewhere else. And it's remarkable when you do how the whole water level rises around a team because quite often these individuals are sucking so much energy. Right. And attention that they effectively suppress the capability of others to perform. I've certainly had scary situations when I guess it was headhunted for the second time here in Singapore. I was brought into A US Company whose business unit here in Asia was isolated, not performing well, and really had some bad behavior and difficult people going, sort of weaponizing information and things like that, you know, that type of behavior. And I think, you know, one of the most difficult challenges I had in my career was someone who, from the very first time you met them, was giving you out and out hostility. And you're trying to figure out why and you're trying to figure out also how can I actually leverage your expertise and work with you because you are the most experienced person on the ground. Right. And I would like to work with you. But you're trying to also get to understand why are they acting that way and they're obviously projecting something onto you that they can't quite express. Right. And in this case, this individual was very angry at the fact that someone else had got that job instead of them. And also someone that they perceived to be non expert in the industry, which was fair comment, but that's not the reason why I was there. Right. So again, you've got to be very conscious and mature enough to know what you're good at and why you've been promoted when you might not be expert in the industry or the product or the minutiae that often companies obsess about. Right. That, you know, so again, having that. And that's where a lot of people, you know, sometimes get an imposter syndrome. Right. Because they're more worried that they don't know the details as opposed to the structures and the processes and the good things that they can do. So I think those are the three major challenges I would have faced over time. Right.
This is a great synopsis and just a little message for the listeners. Listeners, Our friend Rich here is not just a scholar, but also a gentleman. And I want to revisit something that he said. You said, let people be happy somewhere else. That is the nicest way I've ever.
Heard and described with letting somebody go. So let's, let's get into this because.
In the sales world especially, it's, it can become very competitive. The money that we put up seems almost like scores. And we can look at the scoreboard and say that the scoreboard justifies everything that we do. And a lot of times we have toxic high performers who can objectively say, look at me, I'm putting up numbers, I'm meeting quota, I'm excluding quota. So I'm going to be as toxic as ever. And I feel entitled to said toxicity. And so for you, as a sales leader, it puts you in a really tough position to advocate for your team and for your culture and potentially have to let somebody like that go. So walk us through that process, what conversations need to happen and what kind of resilience you need to have as a leader to make that happen.
Absolutely. So I think the first thing. So again, if I think back to this, you know, specific scenario where this individual was being hostile right from the very beginning, one of the first things I did was to try and identify in the rest of the group, which wasn't very large actually, who the pillars of my future culture might be. Because I also think the job of a leader, I have heard it said that the job of a leader is to make themselves redundant, which is very, very emotive language, right? It's not literal. You're not trying to make yourself redundant. But what you are actually trying to do is confer leadership and behaviors on others who will support what you're trying to build. And so it's vital that you find them. That's the first thing. People that you can work through, that you will confer some responsibility on, provided they're willing to take it, obviously to build what it is you're building. But then the other thing I think about, you know, I use the analogy of a sales team like a car engine, right? And I confer the responsibility on people in my sales teams to be expert in what they do. And they may be small components, they may be large, right? Because you could have key account relationship owners of the 20% of companies that provide 80% of your revenue, for example. So that's hugely important strategically and everything. But you could also have within your group those who are doing, let's say the SME market, perhaps smaller deals, what have you. But the key to an engine is that each of those components is expert in what they do and the problems happen when one of those components breaks or gets out of, out of kilter. And ultimately, if you then consider that the journey towards your target can either be smooth and exhilarating or it can be bunny hops, because you have people problems, right? This is what you're trying to do. You're trying to create that harmony, which is about creating a mission where everyone knows what the, the key focuses are, including mine, and they know how their focuses and targets and what I expect of them roll up into that, that is essentially a well oiled machine. And then obviously your pipeline is the fuel, right? And you need to be good on your data and all that good stuff and you know, have good reporting and all the good behaviors around that as well. Right. So that you have predictability on your journey as well. So I think it's a combination of those two. But don't get me wrong, it is frightening if you're conceiving of potentially letting someone go who has either been celebrated or lauded or in this last case, frankly, was the person who knew everything. Right. And I was not expert in this business I was coming into, but I also knew that I needed people who would pick up the responsibility and I would help them in this, in finding their internal network so that we could build procedures and capabilities. And this wasn't just sales, this was around customer support, this was around implementations. And I remember hiring people who I knew I could not really adequately support. They would have to go and have to find their own answers and they would have to almost create their own job description. So I needed that kind of initiative, self starting element and people who would have the courage to come to me and say, hey, I need help on X, Y, Z. Right. As opposed to me being able to direct them in a particular direction. But it's frightening, right, when you're conceiving of letting someone go. But as long as everyone is comfortable, there's a psychologically safe environment. People know what the mission is, they know where they're focusing for success. And you're supporting them in that. You can do it, you can get there, you can overcome pretty much anything. And that, honestly, I'll just finish on this is the most powerful thing because one of the things I also try to advocate is getting beyond that financial year to year thinking and starting to think about your three to five year horizons. What are the things that can absolutely provide rocket fuel to your business, whether it's a new product or opening a new country, whatever it might be. And this is why you've got to free yourself from the escalations part because you want to be able to think about these things that are going to underpin your journey. And then when you do come back to your group and you show them where it started, the challenges, and they know that you've got growth and you've come to a certain point here, you've got almost an unstoppable horse because they know and will have passion towards that next three to five year journey, whatever that entails. So that's, that's ultimately what you're trying to get to. But it is a fragile thing. You have to look after it.
Absolutely. And I love this response because we are focused on the future. We have this three to five year journey that we have in mind and then we have a very clear set of mission and vision and values that everybody's bought in on. You create that psychological safety and then charting that vision with the mission, vision and values and having psychological safety leads us to trust. So you're getting the trust of the team members and then you're taking the time to learn about the organization that you're in so you can understand the individual parts of the engine that drive the business and then you can say what fits, what doesn't. And if you have to make that hard decision, people might be initially concerned or hesitate, but since they trust you, they trust the mission, they see the journey. They can say, I can understand how you came to that decision. You're not coming in and saying, hey, day two, I'm offing your best person.
That would be terrifying.
As much as you would like to.
Exactly. So I just wanted to make sure that the audience realizes there is a.
Process that is need to be followed.
Yeah. And you know what, there's another component which is fun. Right. If you've got people who are seeing growth, seeing success, and they're part of it, right. And they feel they're growing and they're invested in and they're having fun, then that, that's a culture that's going to stick around for a while. As I say, though, you do have to maintain it. It is a fragile thing. You only have to look at your sports teams to know that. And you need to be jealously guarding your culture when you have it. But when you do have that point, another thing I would do is when hiring for people, you know, I'd make sure that the team is also having an input there and interviewing those people for the cultural fit as well. And I've certainly, on a few occasions, decisions over mine and it's worked. So as I say, you're only a headhunter, a merger or an acquisition away from having to start all over again and it being someone else's turnaround story. Right. So these, you know, culture is, is never there for all time. Is, is the other point to be aware of, I guess.
No, that's a great point. And it, it is something that keeps you sharp too. Right. Because I think sometimes feeling too comfortable can lead to stagnation and then we stop growing and developing. And the way that I think about culture is that it is a, it's a never ending negot with all members of the team. It's going to shift with time, the market's going to shift and Everything like that. But as an astute leader, you have to be that bellwether to understand which way the wind is blowing and what adjustments need to be made.
Yeah. And then you might have a different problem, which is, you know, instead of helping those to be happy somewhere else, you might have succession planning issues. Right. You know, what if you lose a top performer and it's not of your choice. Right. And they're going on to something bigger, better, perhaps, whatever it might be. So, again, you've got to. That's sort of getting into your leadership suite in the sense of having that program of understanding who your talent is, how you're going to keep them invested, how you're going to promote them, perhaps how you're going to give them other opportunity, but also having that sense of if someone chose to go somewhere else, what happens then?
Right, right. And I think when a sales leader finds themselves in a situation, there is one simple solution, and that is to buy your. Your book, my friend. So before you go.
Oh, man, I love that.
Thank you.
Could you remind the listeners again about.
Your book and how they can get in touch?
That's amazing. I love that. Thank you so much. It's called the Cultural Sales Leader Sustaining People Attaining Results. It's available wherever you. You get books. So it's on Amazon globally. It's on Barnes and Noble, I think Google and Apple and perhaps some other places as well. If you do get it, please find me on LinkedIn. I'd love to know what people make of it. I'd love to hear their feedback. I've had some amaz stories already, and it's really quite a joy for me to understand that it's resonating. So please do find me that way. Or richardcogswell.com as well is another way to have a conversation.
Amazing. Richard, thank you so much for joining us. Really appreciate it.
Kwame, it's been such a pleasure. Thank you. Really great talking to you.
Perfect. Wait, wait, wait, wait, wait.
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