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The iGaming Leader Podcast with Leo Judkins uncovers the human side of the iGaming industry's most successful leaders. Join us as we explore the untold stories, challenges, and triumphs of the executives shaping one of the world's most dynamic sectors.
Each week, we dive deep into conversations with C-suite leaders, founders, and directors from global betting firms and innovative startups. Our guests share their authentic journey to the top, revealing pivotal career moments, leadership philosophies, and personal strategies for sustainable success in this high-pressure industry.
More than just another business podcast, we focus on the crucial intersection of wellbeing and high performance. Discover how industry leaders maintain peak performance while managing stress, work-life integration, and team dynamics in an industry that never sleeps.
Whether you're an aspiring leader, current executive, or passionate about the iGaming sector, each 30-minute episode delivers actionable insights to help you thrive in this fast-paced environment.
Subscribe now to join a community of high-achieving iGaming professionals committed to making this industry not just successful, but sustainable for its leaders.
What compliance is NOT
Alex Henderson: [00:00:00] They get the belief of my role here is so focused on everybody's a criminal or everybody's got a gambling problem. But that's just not the reality.
I think the message that it sends, just the word alone, is we are here to make you follow rules to comply. It's not what we do.
I mean, the whole role of working in compliance is protection.
Alex Henderson: I like to make quick decisions.
If you take time, especially in the iGaming world, you lose out.
If you are not the first mover, you are often then chasing. If you are not the first one to do things,
it can cost the business market share. And that means because I'm quite decisive, it could go one of two ways.
It was fantastic from a compliance perspective, but it cost the company money.
We were limiting accounts, closing accounts more than any other operator. And commercially it had a massive impact.
I cost the company a lot of money there
Alex Henderson: Something had gone really wrong in the business, and I did get the blame. I did get thrown under the bus. It was a case of this has gone really wrong. It's all your fault. You've got to fire people within your team. Your job's on the line. I felt it wasn't warranted
Leo Judkins: Welcome to the [00:01:00] iGaming Leader Podcast, where we uncover the human side of some of the most inspirational leaders in our industry. I'm your host, Leo Judkins, and as an ex iGaming director term performance coach, I've worked with over 200 leaders from companies like Entain 3, 6, 5, flutter, and many more to help them build the habits.
To achieve sustainable high performance.
In these episodes, we share exactly what it takes for you to achieve the same. So with that being said, let's dive in.
Leo Judkins: Hey everybody. Welcome to the iGaming Leader Podcast. I am here with Alex Henderson, VP of Compliance at Midnight, and he is the co-host of, one of my favourite podcasts, compliance Chronicles, really amazing, amazing show. His career spans from, UK National Crime Agency financial investigator to building compliance departments, from the
I think really [00:02:00] Alex, what makes your story so compelling is not just the trajectory that you've been on, but your willingness to kind of look at moments where leadership got messy, where good intentions really led to unintended consequences. And you being really open talking about all of those things on your own podcast.
I'm really excited to have you here and, and talk through some of those moments. So thank you for joining.
Alex Henderson: Thank you for having me. I've been looking forward to this for a while, so I'm excited.
Leo Judkins: what I wanted to, start with is, is something that is maybe a little bit controversial, I don't know, but you've mentioned that, compliance is possibly the worst possible name for what you do, and I'd like to start off with that.
Why, why do you, why do you believe that's the case?
Alex Henderson: I think the message that it sends, you know, just the word alone to people who don't know what you do, first message is we are here to make you follow rules to comply to it, it's not what we, do. I mean, the whole role of working in compliance is protection.
You are there to manage risks and protect [00:03:00] employees in the business, and I think. There's somebody who I really respect in the, in the compliance, realm, Christian Hunt. And you know, he was one of the first people that I heard say that and he, he put that message in my head and it, it got me thinking. And I try in every role that I work into, not reference that we are the compliance team or the compliance department or, or use the title offices. Try to reference us by our, by our names and what we are doing. So, you know, for example, I've got x joining the call today who's going to help us understand the risks around anti-money laundering as opposed to I've got this anti-money laundering compliance officer joining the call.
'Cause it just, yeah, it gives that perception that we are here to make you follow rules and I just, I, I don't like that.
Leo Judkins: it's one of the tricky parts in business, isn't it? Where you, on the one side you have the commercial side of the business that wants to generate revenue, but also of course needs to, you know, follow. Certain procedures and make sure that certain accounts are, that accounts are in a good state.
And then on the compliance side, there's so little [00:04:00] upside to people that are working there to keep an account open because if you keep the wrong account open, obviously that's a massive issue. Comes with fines, comes with all of that.
Whereas there's upside in actually closing account. And on the commercial side, you kind of have the opposite, right? You obviously wanna generate, revenue for the business and
Alex Henderson: well, I disagree with it. I think the job of compliance is to keep the account open. The job is to find a way of making that customer, have a good user experience and
fit within your rules. And especially with junior people within compliance They get the belief of my role here is so focused on protecting business, which it is that Everybody's a criminal or everybody's got a gambling problem. But that's just not the reality.
And flip that mindset with them, with, they need to look at every account like, this customer is a healthy human being and this person knows what they're doing with their money. They're not a criminal, we need to look at that account with that mindset. The mindset of, oh, I, I've gotta do more adverse media [00:05:00] because adverse media searches because, you know, I couldn't find a connection and almost, I, I've worked in place in forward, they almost keep digging until they find something, till they find something negative on the account when not the reality, especially with the UK public, it's not the way it is.
So, I, I, I disagree with it. And we try and challenge all of our, of our team members to look at accounts with that mindset of how do I make this account? Compliant without, you know, bending rules. For example, my process tells me that this customer has hit a, b, C trigger, and therefore the signs show that, they might be involved in some illicit activity, you look through their behaviour in a bit more detail.
You look at their profile on open source, and you can see, actually no, this, this is clearly a good person. Maybe it's the triggers that need adapting as opposed to you restricting that account. So we always challenge them to, before you take the strictest action on account, help us understand, is it our process that needs changing before we try and change the customer's journey?
Leo Judkins: Love it, mate. I, I [00:06:00] think, I mean, one of the things that you, I've heard you say a few times is that you really, you'd rather be, you know, full, flat being super innovative than follow mediocracy. And I kind of, you know, I. It kind of shows here as well. How, how does that, how does that show up for you in your, in your day-to-day job, in you managing the team, in your leadership style?
Alex Henderson: it's, it's going to sound like I'm lazy, but my, my leadership style is really, I just try and enable everyone around me and, and give them opportunities. I'm, when I'm hiring people and when I'm working with people and if they've been given a certain role in a company, they've already proven they can do the job. So. It would be disrespectful of me to then limit them, limit what they're allowed to do by saying, no, this is a process. Only go and do that. This is the policy. Only go and do that. I think that's almost arrogant on my part to say that that's where your boundaries are. So my mindset is if you can challenge the way we do something, if you can find a different way of doing things. Do it, take a risk and yeah, it [00:07:00] could go wrong, but take that decision and I'll back you. You know, as long as the risk isn't, I'm going to let somebody who's clearly financing terrorism, you know, with withdraw a chunk of money, it's, I want them to look at everything that they do. Everyone in my team, everyone that I work with, and always be asking, is it the best way we can do things?
And anyone that comes to me and says, I'm thinking we should change this process, I'm thinking that we should open this customer account because of this. I'll always back them. I'll always back
it goes wrong, you know, it's me that will get in trouble. That's fine. I accept that. But so far the rewards in my career have outweighed, the, the negative side of things.
Like there's been a few things where I've got it really, really wrong. You know, massively. And there's been impact, but it hasn't definitely, there's been a lot more benefits and I look at the people that have worked with me over the last, say, 10 years when their careers have gone. I don't think that I would've been able to help their careers as much.
Not that I, you know, I was you know, their careers are what they are, but I think it helped by [00:08:00] just me just saying, go, go and do your job. You know, I, I'm not going to, I'm not going to limit you.
Leo Judkins: Has it always been like that? Alex, have you always been like that? Because I, I can imagine in, in, in roles where it's more process driven, really the easiest way to do is to, to operate is just follow the process. Obviously that doesn't create any engagement from your team, but it also limits that risk.
Right. And you sticking your neck out and so, so tell me a little bit more about. If you've always led like that, and, and I also love to hear what you just said about where it has gone wrong, and it massively has affected you.
Alex Henderson: no, it definitely hasn't always been that way. I think, you know, when I was more junior in my career. I, I looked up to my managers and I followed everything that they said, and I stuck to policies and procedure. I think as I've got more senior in my career, and I've earned a fair amount of trust when whenever I'm in a, a role, like even now in my new role, a fair amount of trust there that okay, let's believe Alex, he, he must know what he's doing 'cause he is fairly senior in his career.
I've managed to convince them of that. So they put a lot of trust in me and I just [00:09:00] returned that trust to my, to my colleagues. I would never, I never worked this way When I was more junior in my career, I followed everything the way it was. Because I got burnt a lot. Whenever I try to push things, whenever I try to challenge the way things were in a business, I didn't have great leaders around me always, which I'm grateful for 'cause I learned a lot from them. So I've just tried to flip that a little bit and make sure that I don't follow in the footsteps of bad leaders that I've had. And, um. like I say, in, in terms of when it's gone, really, really wrong, I like to make quick decisions.
I think if you take time, especially in the iGaming world, you lose out if you are, if you are not the first mover, then you are often then chasing it, whether it's in a new market, whether you are changing the way that you approach safer gambling, marketing, etcetera If you are not the first one to do things, it can cost the business market share. So I'm always quite decisive. I'll make a decision on something and that means because I'm quite decisive. It could go one of [00:10:00] two ways. I'll, I'll obviously weigh everything up. I'll, I'll, I'll, I'll, I'll follow regulations, legislation, but I'll be decisive. And I suppose the best example I have is a previous role I was in, we were trying to be really innovative around safer gambling.
We wanted to do things. Differently, We wanted to do things good for our customers and, and, and push the limits in terms of how good are you, how good we could make safer gambling.
From a compliance perspective. I had a really great, great team around me. We worked together. They very much led on it and I just enabled them and said, cool, if you think this is great, you think this is going to be industry leading, and it's going to protect our customers, let's do it. I was quite rashed with my decision. 'Cause that's the way I work. And the, the outcome of it was, It was fantastic from a compliance perspective, but it cost the company money.
We were, we were limiting accounts, closing accounts more than probably any other operator. And commercially it had a massive impact for around, [00:11:00] three months until. We got the analysis where we looked back at it, and for me, it took longer than it should have. But again, another valuable lesson. But we, we cost the company, I cost the company a lot of money there because in hindsight it was fantastic for compliance. But I should have not taken that quick decision. Got a little bit more analysis on what the potential might impact might be, and then I would've, I would've taken a different approach.
But it was still a good lesson, just a costly one.
Leo Judkins: one of the things I found really interesting of what about what you just said is after two, three months you, you get the analysis, you see that it's wrong, you, you action it, you obviously reverse it or change it in a way that it's commercially better for the business.
How do you go about kind of reviewing the quick decisions that you're making? Because Yeah, I, I completely agree with you. Being fast is, you know, money loves speed, right? It can go wrong. So how do you go about that? Typically,
making sure that you've made the right decisions and then, you know, potentially actioning it based on, based on whatever you [00:12:00] found.
Alex Henderson: whenever there's a, a decision being made that has potential commercial impact, which is almost every decision in compliance. We have in place measures, we have in place metrics that on an if I want it hourly, I can get it hourly, if not daily, weekly. And now I just keep a much. Tighter sight on it. Or I have people with me keeping, you know, much, much higher levels of visibility on it. It can go either way. It's if it starts to show a sign if we've made a change and okay, all, all of a sudden customers are spending more, or we're getting more registrations.
Fantastic. But have, have we missed something here? It's really, really good, but is it too good? And then on the flip side, again, if maybe we've gone over compliant, if we've seen a decrease in registrations, a decrease in customer spend, has caused this? And we'll look at it that way. So now I'm just much more finger on the pulse and quicker to react because you know, day a week of poor registrations or poor registration journey, or first deposit experience. Is, is costly, right? 'Cause customer [00:13:00] expectations in the gambling industry are through the roof. They, the customers expect so much, there's so much competition. So that, that first experience is, is, fundamental to the long-term relationship with customers. So now, yeah, I'm just much, much more finger on the pulse.
Leo Judkins: that's so true, isn't it? It's, there's so much competition. There is no loyalty really from, from a customer perspective. So yeah, bad first experience will, will massively impact it. I often think about it like the nose of an airplane. You know, when in the beginning you make a bit of a difference at 1% difference in a customer's experience, that has a huge.
Outcome on the end result. Right. Whereas, if you do that at the end, you can only change a little bit.
Alex Henderson: I, I, I was having this discussion with someone the other week and, we were trying to think of examples like that. What, what is it like in terms of customers for gambling? That's, and my, my example, as I said, it's like, it's like speed dating that will make up their mind within seconds, whether you are the one.
Make up their mind first based on visual. And then it will be the experience in terms of how the, how the conversation [00:14:00] was. People will make up their mind so quickly. They'll make up their mind. They will judge a book by its cover.
First of all, they will do that. And then if you don't win them over or through what you are demonstrating throughout the user journey.
Leo Judkins: Yeah, Alex, you said one of your proudest moments, or experiences is really building a compliance department from, from one person to 30 plus what's the story behind that? Why is that? Why is that moment or that journey something that's made you so proud?
Alex Henderson: would say the reason it made me the proudest was because when I first started that job, I was. Inexperienced. I was, told something when I was young, which is, fake it till you become it. And I think I took that job when I probably wasn't ready for that job, in hindsight too, to be leading a compliance function. I would probably, I could have done with a few more years at a more junior level. But, you know, I, I've done my best and I think the reason I'm proudest of it was because throughout that whole experience of growing the team. Felt like [00:15:00] I just kept maturing. I kept learning. I kept making mistakes, but I just kept learning. And the two things for me were, I felt like I was always improving, but at the same time I.
Was really happy. I just kept making opportunities for people around me and. Their careers just kept getting better and better and better. So that for me was, the biggest thing was, was just, it, it enabled growth for, for me and, and, and so many others, which we wouldn't have been able to do had we not got gone on that rapid journey of, you know, starting off with one licence I, you know, or two licences, a, a UK licence and Mona, and then entering you know, four, five different markets over a few years having seven, eight compliance officers, big AML team, safer gambling team. You know, I, I wouldn't, when I started that job, I would never have imagined that it was going to spiral into something like that. But it was just, it was, it was a great experience and I think it, it allowed me an opportunity to make a ton of mistakes, and I keep referring to that, but I've [00:16:00] learned so much from all the mistakes I've made. But it allowed me an opportunity to make so many mistakes. And I think because I earned the trust of the company owner and, and, and senior people quite
Leo Judkins: Yep.
Alex Henderson: that they gave me quite a lot of freedom. It was a case of, okay, if, if Alex thinks this is the right thing to do, then okay, let, let, let's do it. Yeah, I don't think I would've experienced it anywhere else, but I'm, I'm grateful I had that opportunity because I definitely wasn't ready when I first started. Definitely.
Leo Judkins: I think it, it's certainly something that happens a lot in gaming, right? In many, not just, not just in compliance and in almost every single area of business where people kind of jump into a role that they're not quite ready for, and they make really fast progress through that career, almost having to.
Perhaps fake it until they make it because they don't feel ready. It's outside your comfort zone. And then yeah, either, you know, make it, or, or the break right. Often happens as well. So when you think back through that journey of yours, what are some of the, the, perhaps the leadership lessons that you've learned, the hard way that nobody [00:17:00] warned you about beforehand, that you hadn't heard about beforehand?
Alex Henderson: you referenced on the other day that I'd said before where something I believed early on in my leadership career was that. You have to work. You have to work nonstop. Everyone needs to know you are setting the example of you need to be first through the door.
You need to be the last one left in the office. They need to know that you're working till late at night and send that example to them because then they replicate it. I, I was a strong believer of that. I used, I used to be so proud of it, like, oh, I remember. We were working towards an audit, we'd got notified that we were having an audit with, with one of our regulators. And I had everybody in my team, across a number of jurisdictions, working ridiculous hours because we had to get ready for the audit. And, you know, I remember there was one guy, who had just become a dad. And he was working until three, 4:00 AM and I didn't have the experience and even the compassion to, to tell him, switch off.
Stop doing what you're doing. Remember going into [00:18:00] work the next day and telling my boss, yeah, we've got everything ready for the audit. I had everyone working until 3:00 AM amazing. We're good to go. And being really proud of that moment. I know, you know, that can happen right there. There will be times when people were forced to go above and beyond and work extra hours.
It, it, it's in every role. But as a leader, I, I didn't see the signs that, was impacting people's personal lives. That, what I've learned from that, and what I now practice a lot, is the moment I see somebody working. Hours that they shouldn't do.
I've got a guy doing it at the moment, and it really bugged me because he's such a great team member, works so hard, but he just doesn't listen. You know, when I say you've gotta switch off, you've got to have some personal time. It's so important because you're not going to know it's a problem till it becomes a problem then you're going to be trying to, recover all the energy that you've lost over weeks and months, which you just can't do. So the best is prevention, almost like a gambling problem. You know, you, you don't wanna spot the late and then somebody's got a gambling problem. It's almost like [00:19:00]workaholic should be in
But that's something now that I learned the hard way now with everyone that I manage, I, I, I keep an eye on them and I, I do my best to make sure that they're taken. For themselves, that they've got personal time, that they're not overworked. I look at their schedules. I look at, you know, the, the hours that they're working, the efficiency that they're putting out.
I'll talk to 'em about things going on in their personal lives. And I have never done that early on, I have never done that. I distanced myself from, from a lot of my colleagues because I was told by one of my managers, don't build relationships with your team because you're going to have to fire them at some point. And I, and, and that stuck with me. So I, I never used to build relationships, whereas now maybe I shouldn't, because yeah, there will be times when. Companies are forced to make redundancies, but not going to not build relationships with people that I spend so many hours within a day, and when I'm meant to be their leader, I'm not going to close the door just because some, at some point they might not be who the company wants.
That's, yeah. So I changed that, and I learned that the hard way.
Leo Judkins: It. I mean, I've had Mike on the [00:20:00] podcast, Mike on the podcast, right? So we've got some really extreme examples of what can happen when, when, that does go wrong.
Often think that it's not, it's not an all or nothing thing, right? it's like a scale, a gradient almost, where.
I think if you're constantly on, the problem is not just the fact that you might burn out or like might get a mini stroke or whatever it is actually that everything before that also means that you are very likely to be underperforming because you're never, your battery's never going to be operating from like a fully charged perspective.
Right? So. I think from that aspect, it's a really crucial piece. And, how do you, how do you go about that? How do you go about switching off and how have you, you know, you're talking about how you changed that over time with you, with the people in your team, but how's that shown up for you since having that experience?
Alex Henderson: I mean, my, my kids are a lot older now, so, I'm conscious of the fact that my, my, especially with my son, he's almost at that age where I know he's not going to wanna spend time with me any more. You know, he's, he's becoming a teenager [00:21:00] and every spare minute that I get, I, I just wanna spend it with them because
I am going to be a moment where I just don't Yeah, they don't, they don't wanna be around me. This is going to sound horrible, but there, there are times when my parents call me I look at the phone like, I can't do it right now. You know, and I'll ignore the phone call, and I have this period of, know, it, it lasts normally about an hour.
I just feel so guilty that I've chosen, and I know I've got a job to do, but I've chosen to sit in this meeting instead of answering the phone to my mum, who, you know, it is normally a five-minute call. She, she's just calling to gossip about something that she's heard and a little chitchat, but that means so much to her. I've disregarded it so I can join a work meeting. Whereas now, if a meeting isn't critical and my mum or, or my dad or family member's called me, I will not get into that meeting. I'll tell, make my excuses. I'm going to be 10 minutes late. I've just got to do something on of, of a personal nature, and I'll speak to my mum. So that's always been in my mindset. I want my son to have that same attitude as my daughters have that same attitude [00:22:00] towards me. So I think that's what really changes. I'm conscious of. My personal time is not my personal time any more. My personal time is my kids' time. It's, it's, it's, it's spent with them. So the way I manage it is the moment they get back from school and the moment, you know, usually it reaches around 6, 6 30 in the evening. They've either got activities that I have to take them to, or they just wanna play. You know, can you play football with me in the garden? And I'll never say no. I, it's, it's something I do no matter how tired I am, no matter how my day's been. That is how I manage things because. They just keep me quite grounded, and you know, I live with a realization that there's probably not many more years left where they wanna spend time with their dad. So I make the most of it.
Leo Judkins: Amazing. There's this amazing graph that shows how much time we spend, with our kids over. You know, as they get older and it's a really steep curve. So yeah. Anybody listening, and struggling to switch off. You might wanna look up that curve. It, it did the same thing for me as it did with you, Alex.
It's like puts this mirror in front of you [00:23:00] of going, Hmm, maybe I should change my priorities here.
Alex Henderson: Yeah, I just make the most of that. I mean. I exercise a lot. You know, I'm quite into, into my training. And I do different things for longevity as well. Again, coming back to my kids, I wanna make sure, you know,
I wanna be that 70-year-old that goes and runs marathons with my kids and
grandkids and
stuff. So, I think it's all just comes down to me just wanting to be around my family for longer and work is a low priority.
If I, if I could do a job that ended every day at one o'clock or two o'clock in the afternoon, yeah, I'd do it in a heartbeat.
Leo Judkins: Yeah.
Alex Henderson: work, I would, I would do it straight away.
Leo Judkins: Hey, one of the things you said in that example of the 3:00 AM email, right? And I heard you talk about that on, on one of your episodes where, you know, men mentioned people sending emails at 10:11 PM and your team work and all hours as a result.
In that episode, you said, how bad was I as a leader? Making, you know, making them think that all of that came first. Right? It's the same example. I've got the same question the other way around. So I often think we, we see things [00:24:00] looking backwards that me. At the time, we thought it was amazing. We were doing it really well, and it's because we just didn't have the knowledge, and we didn't have the experience.
If you look forward now, let's forward ourselves like five, 10 years. What are some things that you're currently doing that you might, in five or 10 years, you might be thinking, oh my God, Alex, why are we doing that?
Alex Henderson: I allow people too much freedom and I, I imagine there's going to be a situation where it backfires even more. Damn, why was I not keeping a tighter, you know, tighter reign or, or more oversight on people? Why was I trusting so much? I think that's going to be one that that comes back to, to haunt me at some stage.
But I can live with that because it is risky, and it is and it is a weird approach. I've got it wrong already before where, somebody who I respect a lot, who I used to manage came to me and said, you know, I wish you were a bit more present. I love the fact that you gave me freedom and I love the fact that you, just, let me run with things. But there were times when I wish you were present. But when he said that to me, remember thinking, [00:25:00] damn, you know, he's right. But I didn't change because, and what I said to him was, at the moment I feel like. I give PE people know that I'm present, so I don't need to be calling you every, you know, every few hours or every day to say, you know, how are things going? You know, or the team know they can pick up the phone to me. And I think the mistake I made with him was probably, I just didn't let him know that that was the case, whereas I didn't change my approach to being more present. I just made them realize, I know I just make people realize that I am more present. Because he was open up, open and honest with me, and I imagine there are probably a few other people that I've managed who feel the same as him,
Leo Judkins: Yeah, it's like a spectre, isn't it? On the one hand, like on the one side you've got the complete micromanagement and, you know, standing over someone and like checking every keystroke they make versus complete freedom and not being there. And I, it's, it's impossible to get that right in the middle because we all.
The way we like to be managed and the way that we like managing, they're different for everyone. Right? [00:26:00] So communication is such a big part of that.
Alex Henderson: I think you've hit the nail on the head, though. I think striking that balance, I, I don't think I'll ever be able to get that right. So all I try and do is. pick the one that I've, I believe is the best for the majority. And I believe that, you know, everyone says, oh, you know, you should treat all the team members different and, and adapt to their, their, you know, everyone has a different way of working.
Yeah, I get that. But when you've got a team of hundreds, you are not going to adapt the way that you work for a hundred different people. You can make subtle changes, but as a whole. You, you wanna embed a culture and ethos within your department that says, this is the way we are going to work As a team, you should know that you can call up any member of your team at any point and just chat.
Not necessarily about work, but just chat. You know, something's wrong. You should know that you can do that, but at the same time, you should also know that they're not, might go a day when nobody's checking on you because they trust you're doing their job. They trust that everything's okay. So I don't know how to get the balance right. I, I do my, try my hardest to embed that culture within my team that [00:27:00] we, we are working together, and you spend more time with each other than you do with your families, and therefore you need to know that you can count on everyone. I would like to think that. Most of the people I work with, if not everyone knows, they can pick up the phone to me and, and talk about whatever they want, you know whether it's work related or not. And I'll listen. I might not have the best solutions, the best ideas, but if nothing else, I'll listen, and I'll hear what they've got to say. And sometimes enough.
Leo Judkins: Love that. Hey, Alex, but you, your reputation and how you are seen is, is really important to you. I remember, when you told that story about a team member who lost respect for you, I, I could see how much. You know, that was really, that, how much that impacted you and what that meant for you. Not just because it happened, but because it happened in front, also in front of people who, whose respect you needed, for people not maybe not having heard that story.
I'd love for you to retell that and, and to talk a little bit more about why that, how it, how it occurred and why that impacted you so much.
Alex Henderson: yeah, you're right. It was, it was a painful one because up [00:28:00] until this point, I had a really good relationship with this individual.
We got on really well, not just as colleagues, but also, you know, we'd, we'd spent time together personally and um. It hit me hard because the feeling wasn't mutual. I had huge respect to him, both as a professional and as a person, it came out of nowhere that we were just on a group phone call in a discussion about nothing, and he just started raising his voice to me, started telling me that. I'm not fit for the role. He was just making a lot of statements. He'd obviously harboured, and some of them were justified. Some of them were spot on. But it just wasn't the platform for it, and it hit me really hard and I, I had again, you know, one of those things where I lost my temper and told him, get off the call.
We are going to test this one-to-one. But I said it in quite a harsh tone 'cause I, I'd lost my temper, and it takes a lot for me to lose my temper. Then I felt even worse because now I've just embarrassed myself in front of my colleagues, in front of people that I'm meant to be a leader for.
They've just seen me lose my temper over [00:29:00] something so silly. And then we went on to the, the one-to-one phone call and, you know, he carried on for a little bit, being, being a little bit disrespectful, but his, most of his points were justified. So I, so I heard him out and, it just ended the relationship.
It, But because he stayed in the business for a period of time, it then created a toxic environment for some of
Leo Judkins: Yeah.
Alex Henderson: because he was, his messages and the way he felt towards me, he was part trying to pass on to others and sometimes successfully. But it was, yeah, it was just a really tough experience because I hadn't had that before where, I mean, I imagine there are people that don't respect me fine, but I'd never had it where they just confront me in a group environment. And I didn't know how to handle it. I really didn't. Now. The thing I got wrong with him in that specific scenario was that he just wasn't being kept busy with work. So he, he didn't have enough tasks to lose. He had a lot of spare time on his hands and. My opinion of it was that he just built up these, this anger, these feelings towards me because [00:30:00] he could see that I was constantly, the constantly busy, and he could see that I had a certain reputation in the in the company. And I think there was a little bit of resentment there. And then on my part, what I'd done wrong was I didn't keep an eye on his workload and. I, there were earlier signs. I looked back on it, it's like, right. There were other times and other phone calls where he'd been a little bit blunt, but I hadn't, hadn't reacted, I hadn't picked up on it. There were other times when he'd sent a message in a an email group wide, you know, to me, and I'd taken it as well, there's not, you know, not taken any offence to it or taken it as disrespect.
But then when I read back through them, there were clear signs and I wish I'd have picked up on them sooner and had a chat with him and just said. Is everything okay? Have I, am I doing something that upset you?
Leo Judkins: Yeah, I can only imagine that. And, how did, how, I mean, especially when you tied into what you were saying earlier, that one of your earliest managers said to you, don't build a relationship with people. Right. And you then learning, actually, for me to be a good leader, I wanna be authentic.
I wanna build relationships. Like that's an [00:31:00] experience like that could wobble you in a way where you go, well actually, maybe the right thing to do is not have these relationships and not invest all this emotional, you know, baggage into people. So that also, it doesn't feel as, it doesn't hurt as much when situations like that happen.
So how did you, how did you deal with that emotionally afterwards?
Alex Henderson: So immediately after I had a chat with the rest of the team, I remember that I had a chat with the rest of the team that were on the call to apologize for losing my temper for acting out, and for the, for the situation in general.
So, so I remember having that. But emotionally, I think the main thing was I felt really, really embarrassed
Leo Judkins: Yeah.
Alex Henderson: Disappointed that somebody, who I had so much respect for, just didn't feel the same. You know, I was really, I remember being hurt by that because even after that phone call, my feelings didn't change.
I would, I'd
Leo Judkins: Yeah.
Alex Henderson: I, I've got nothing but love for this person. You know, he's a he's a really good guy. So I was, yeah, I was hurt, and I was embarrassed. It didn't change the way that I work in the sense that, you know, I'm quite a closed person anyway around, like with [00:32:00] people in the sense that I've got. Two people who I consider to be good friends in my, in my whole network. Two people who I con consider to be good friends. And the reason they're in that category is because I know that if anything where hap were to happen to me, they would look after my family and vice versa. And I think, and I put everyone else outside that category as friends because I don't think I could count on them to do that. Nothing wrong with that. You know, they're still good people, nice people, but I just know if I were gone tomorrow, they might check on my family for a few weeks, but then after that, that's it. So that's how I categorize it. It sounds really like basic,
Leo Judkins: I love that it is great.
Alex Henderson: but I've got these two guys who, who I know would do that, and I would do that for them.
And outside of that, yeah, I keep, you know, I've, I've got people that I like, people that I'm friends with. But you know, they don't know my innermost secrets, and I'm sure, I don't know, theirs. And I've got colleagues who I respect and who I'm, who I'm big fans of. So that hasn't changed. I still keep that same mindset, you know, I'm not, you'll see when it comes to things like Lisbon, for example, we're talking about that earlier in like the, the, you know, social events.
I hate them. I hate them with a [00:33:00] passion. I attend them because. Every now and then something good comes from it. But being in those forced social environments with people who, you know, in the, in the real world, I would not talk to you if I saw you in the street. The same as when I go to my kids' school and other dads try and talk to me.
I hate it. I, I, I don't wanna talk to you. I just wanna come and pick up my kids. And same with gambling events. You know, I've come here to listen to experts, the panels or, or to talk to people that I've selected. But yeah, I, I don't like those sorts of environments, but that whole, my approach to the way I am with people hasn't changed. I will look out for everyone. Like, about me is that if you are in, in my team, or you are in a business that I'm working in, my whole job is to protect you.
That is, that is the one thing I'm employed to do. I'm here to make sure that the business, The licences stay intact so that the employees have jobs so they can support their families, so that my team have everything that they need to enhance their career so they can earn more money for their families, et cetera.
And that's my one job is to protect people. And the way I do that is I just make sure that I'm, I try to make sure that I'm as approachable as possible.
Leo Judkins: Amazing. Hey, Alex, those two friends of yours, right? The two that you are in your inner circle that you can trust. What are the things about work that you discuss with them, what are the things that affect you so much that you feel you need to bring that to, to that friendship, if anything?
Alex Henderson: so one of them is Ray, who I have the podcast with. So he pretty much knows. Everything that goes on in work anyway. Ray and I have worked for many, many years together. You know, I think it's been over 16 years, give or take Now.
We've been working on and off together. We do our consultancy work together. We do the podcast together. So he knows everything about work because we, we speak on a daily basis, and same as I know everything with him. My other friend, he's my training partner in the gym, so I'll, I'll see him four, five times a week.
I'm godfather to his, his parents, he's godfather to mine, so We speak on a daily basis. And he's usually for me, like, I like to vent a lot. So when, when I had my previous job, I had a couple of people who I [00:35:00] selected where, you know, we would just have calls and I would vent. And they would vent. And he's, that for me, he's an outlet where I'll pick up the phone to him, you know, once or twice a week, in, in the evenings and tell him about my week and then. We flip over, and then he tells me about his week, what's going on.
At the moment, his work is far more stressful than mine, so it's usually him telling me and me just listening. But they know everything. There is nothing They don't know in terms of, conscious of not like breaching GDPR or non-disclosures. But in terms of my challenges and in terms of. What's keeping me up at night and, I'm struggling with, they know everything because they're, they're good sounding boards and usually nine times out of 10 me just speaking to them, with them saying nothing. End up going away with some solutions and some things that I wanna change, so,
Leo Judkins: Yeah. Amazing. Because it's so easy to sit in isolation, right? Especially once you're at the level that you're at, your VP level or executive, whatever it is. And again, especially in your [00:36:00] area where, you know, you've gotta have strong shoulders, right? You, you, get the blame for negative audits. Anything, you know, licence, review, whatever it might be.
Yeah, it's going to be really difficult to deal with because you are ultimately, you can be the person that's looked at when that happens. How, how's that gone for you when, whenever you've been in a tough situation like that and how, how did you deal with that personally?
Alex Henderson: you know, so I had a situation, where Something had gone really wrong in the business and I did get the blame. I did get thrown under the bus when I was of the belief that it wasn't my fault. And, that was really, really tough because it wasn't a case of. You know, let's have a chat about this. It didn't go, things didn't go well. What do you need to move forward? It was a case of this has gone really wrong. It's all your fault. You've got to fire people within your team, your job's on the line. And it came out of no, like, no, it came out of nowhere, but I felt it wasn't warranted
And [00:37:00] that was horrible.
You know, it, it takes a lot for me to get upset, but I, I'm, you know, I won't. Hide it. I was genuinely upset to the point where I was in, I remember being in tears one evening coming back from work, talking to my wife, just saying, you know.
I'm about to lose my job, and there is nothing more I could have done because I, I literally put every ounce of energy into the job, into my team, into protecting the business, and it hasn't gone well. But that's not it. But it isn't because of me. Like I've, I've done everything I can with, with the resources and tools that are available.
I've done everything I can. I'm, I'm getting a blame for it. My job is on the line. People that I care about are going to lose their jobs, and I was really, really upset by it and I didn't, I didn't know how to handle it. I remember having a call with Ray at the time and telling him about the situation and saying, you know, exactly. I, I think, I think I was crying. I'm, I'm not, I'm not proud of it. I think I was crying at the time, 'cause I was so upset. 'Cause I didn't wanna lose my job. You know? My job pays my mortgage and pays for stuff for the kids and. Even at a certain level, you know, people think that, oh, you know, [00:38:00] you've got all this experience. If you lose your job, you're going to find one. Don't worry about it.
That's not the case. You know, that are far more experienced and knowledgeable than me that have struggled for months to find jobs, sometimes longer. so it's a real fear that actually my livelihood is in this company's hands where I've put every ounce of energy for such a long period of time, you know, into this business. And it was really, really tough. And I had that chat with Ray and, um. And again, it comes back to that thing of why I said I count on Ray.
And Ray just said, look, if you feel that bad, leave the job. I'll, I'll, I'll make sure that I'm doing enough hours that I can support you and the family for, for however long you need, etcetera, and I was like, okay.
And it gave me a little bit of security to think, well, if it, if the worse comes to worst and for some reason I lose my job, going to be the end of the world, things will be okay. I was still scared, I was still upset, but that was, that was a horrible experience to, to go through that because. Even to this day, I don't think it was warranted.
I think that the company handled it the wrong way and that yeah, things weren't good, but if [00:39:00] anybody was going to fix it, it was me. Yeah. It was,
Nobody was going to do a better job. But that was, that was quite a tough one.
Leo Judkins: Alex, one of the one of the things that we, you briefly touched on is, redundancies.
You know, when we, when you were talking about not building relationships, and it's kind of an inevitable part of business, it's awful right? When it needs to, needs to happen because the business maybe, maybe it's grown in the wrong direction, or perhaps we have a structural change to the business on how we operate or whatever it is, right?
So. I think they're often the hardest part. Not, not just because of the, the actual conversations for me personally, and I don't know if it's the same for you, it's actually everything leading up to it because it's in your mind, you're already making the plans. You can't tell the people that you've worked with for so long because you can't give anything away.
Like, how has that been for you when you've, been in a situation like that? How, how did you go about it, and how has it affected you?
Alex Henderson: Probably the one of the worst experiences of, of, of being in a senior position, right, [00:40:00] is knowing that you are taking somebody's food off their table, especially if they've got families. When it's happened in the past. I'm always involved. I like to be involved in those meetings because I've got relationships with these people and I always get advised by, by very, like, in some jobs, I don't know if it's, it'll be the same, you know, in, in other, in all places.
But no, no, we'll take care of it. You don't need to be there. You know, it can be quite tough, but I like to be there because even though it's painful, and it's difficult, I, it's almost like I'm hiding if I'm not in, in that call. And I wouldn't want them to think that I was to blame as well. So, I mean, that I've worked with that's been through that position where they've been made redundant. I've, I've ended up having good relationships with some of them. I reemployed in, in various jobs, but I'll support them. Not like I'm sitting there supporting them financially, but I'll support them in the sense that I'll, I'll do everything I can to help them find new jobs. I'll, I'll vouch for them. I'll go to bat for them, you know.
To, if they're, if they're looking for a new role. But there's no great way of handling it. I mean, you kind of have to live with the fact that this [00:41:00]person's life is changed, hopefully for a short period of time. And I think the way I handle it's, I just stay in communication with them.
You know, after it happens, I just stay in comes with them to make sure, you know, as best as I can, that, that, that they're getting by. And that hopefully it doesn't take too long for them to find work. But. Yeah. I don't, I, I don't think I found a secret recipe to how to handle that. 'Cause it's still, I know, I imagine it's the same for everyone, but I still hate it when, when
Leo Judkins: Horrible. Yeah.
Alex Henderson: up. But yeah, I think staying in comes is important. I think they need to know that when they've left the business, they haven't lost you as a, as a peer, as a colleague, you know? 'Cause it's, it's a big change, right? You've gone from working with people every day to now, not only do I not have the salary, but I don't have those people that I depended on, depended on to speak with. So keeping those come is, is vital because. It's a mental health issue as well, right? Like it's a it's a big thing to go through. So, that, that's the main thing I do is I just try to stay communicative with them.
Leo Judkins: Yeah, I love it. It also shows that you care, right? That the, the relationship that you [00:42:00] built up wasn't something that was fake throughout your, the career span that you had together. So I think that, yeah, makes a lot of sense. I'm going to ask you a bit of a difficult question here, Alex. You, you had mentioned something on your podcast where you said, I still don't see, I still don't think of myself as a great leader right now.
And I found that really interesting. My difficult question is what needs to change, or what needs to happen for you to feel that you are that great leader?
Alex Henderson: I think what it is, is that. When I go to, you know, certain conferences or I, I watch a lot of podcasts and I, I hear from different leaders and, and what they do. I think that's what it's, I realize I'm so far off the mark in terms of there are, they seem to have got this magic recipe that everyone around them is succeeding and doing great and.
You know, I, I still make so many mistakes, and maybe that is part of being a great leader. I don't know. But I make so many mistakes that, nobody's ever going to hire me after this. They're going to think I'm just like, mistake [00:43:00] prone. I'm like the, the, the Frank Spencer of compliance, just like clumsy with everything.
But yeah, I think, I think because I still, I still am decisive. I still take risks and I, I still try to support. Commercially, where a, where a lot of compliance people, especially in, in leadership, take a risk-averse approach. Like, no, you've gotta do it this way because the laws and the regulations say it.
Whereas my mindset is always, let's find a way of navigating it. And I, I, so I think for me to be, to even think of myself as a great leader, I would like to have a room full of people that I've worked with, that I've managed, and I've overseen and get their opinion, and that might make me think that I'm a great leader, is if they all turn around and say, yeah, you know, you, you, you are good.
You are a great leader. Then that might make me feel that way, but I imagine if we've got a room full of everyone that we, that I've managed, it would be hopefully, you know, around 80, 90% of them that would say that. But there's still that 10% that would be like, nah, you got this wrong. You got that wrong. [00:44:00] and don't think of me as a great leader. So for, I think it would take that, it would be, you know, let's get a room, let's get everyone Alex's ever worked in and see what they say.
And that might change it or that might make me feel terrible depending on what they say.
Leo Judkins: Yeah, there's always going to be a percentage like that. Right. And it is just like, you are a humble person and, that's amazing that, that's exactly what I, I think that's what great leadership is. Also, I'm, I'm just going to push back on the mistakes, think that you mentioned. Don't you think that our biggest growth moments, the, the things that, like pivotal moments for us, right?
The things that really change the way we are, the way we think, the way we lead, don't you think every single one of them is born out of embarrassment or overcoming major challenges and actually making mistakes?
Alex Henderson: Oh, 100%. I will not, I'll never change that. I will keep making mistakes. I won't, I won't change that because. It's a message that I send to my kids. I'm a big, big sports fan. A lot of the things I do in my career have been influenced by people who I love in sports. I, I've mentioned it before, people [00:45:00] like Kobe Bryant, his, his mentality of how hard he trains, how hard he, how hard he pushes his teammates to get the best from everyone. And, and again, you know, I'm obviously, I'm five foot nothing. So it's weird that I'm a basketball fan, but even, even, even Michael Jordan, you know. I use that with my son and my daughter because the children are amazing athletes. Really, really good. My son, who is probably the most talented footballer at his age that I've seen in terms of, he has all the ingredients to be an amazing footballer.
He, he plays at a really high standard, but he won't back himself. Sometimes he won't take risks. There'll be like a one-on-one situation with another football player, and he'll do the safe option and play a really good pass. And I always say to 'em, no, take that risk. Look, get tackled. You know, lose the ball, miss the shot.
Do it because you are going to learn from it and it, and it'll help you. So I wouldn't wanna be a hypocrite if I'm telling him that. And then I get in a situation where I've gotta take a risk and I choose the very, very safe option.
Just because I'm afraid that that mistake might cost me [00:46:00] something. 100%. I think you've, you've gotta make mistakes. You absolutely have to. And I think the big part of my mentality of being that way. I had this amazing manager really on, in early on in my career, a lady named Elizabeth. And she was incredible. She was, a black female in a world of, of white males, and she was just so. Powerful and didn't take no for an answer. And I remember her just sitting down with me. We, we were at dinner, and it was the first time like a really senior person that had invited me to dinner in a form environment.
And we were having a chat and I asked, I asked her like, What do you think? You know, what separates you from everyone else? And she made a little bit of a joke at first, but then she said, no. The biggest thing is I will always take risks and I will always make mistakes and I live with it. And that was it. And that was the end of the conversation. And I went away from that thinking, okay, well if it's good enough for her, then, you know, and she's somebody who, to this day, I look up to. Yeah.
So I'll continue to make mistakes, just hopefully not bad
Leo Judkins: Isn't the thing that you said about being a great leader no longer making mistakes, and now you've kind of [00:47:00] turned it around into somebody that you've looked up to most? When I asked you, you said, Hey, maybe when I don't make mistakes any more, or I make so many mistakes and that's what doesn't make me a good leader.
Alex Henderson: Contradicting myself now it's this conversation. It's its, it's got me, it's got me thinking, you know, it's, it is one of those things like, it, again, it's why I like talking to people like Ray, et cetera, is because it, similar and like this conversation is. A conversation can easily change your perspective.
You know, you talk to 10 different people, you could leave with 10 different ideas and, yeah, I think you're, you're exactly right. Just, just from this one, one hour. Yeah. I think maybe I don't wanna stop making mistakes. I just maybe wanna make ones that a less, a less impactful.
Leo Judkins: Yeah. Love it. My very last question is, you've had an amazing journey. I always love talking to people who've just come from the ground, move their way up. They understand the operational part of it.
They also, they learnt leadership. The, the tough way, right, of making the making all the mistakes and, being hit in the face and coming out of it stronger for somebody, [00:48:00]maybe listening that, is in a kind of head off type of position, and wants to grow to where you are now.
VP. Type of level where, like what are some of the things that you, what's maybe one thing that you would say is going to help someone the most and perhaps look at this from the perspective of, if I would give myself one piece of advice three years ago and I'd be able to meet myself three years ago, what's something that I could have done differently that would've helped me accelerate in my career?
Alex Henderson: I, I think the biggest thing for me was when I started enabling people around me. My career changed when I started, going into meetings and talking less and listening more and just. Allowing the people around me to do their jobs as opposed to wanting to be involved in every minute detail, the trust and enablement in, in, in the people around me.
I think was my biggest lesson. It's changed the way I am as a leader. It's helped my career massively, and it's helped the people around me with their careers because they've been able to grow. So I would say that it just enable the people around [00:49:00] you and, and, and trust them.
Leo Judkins: Don't fear the mistakes. Love it. Alright, thanks a lot, mate. Really enjoyed talking to you. Great to have you on the podcast. Thanks for your time,
Alex Henderson: Loved it. Thank you very much, Leo.