Jonathan Fletcher

My name is Jonathan Fletcher. Thanks for letting me come and talk to you today.

Excuse the hobbling around. I got out of hospital yesterday. Not an early excuse for poor-quality slides, but I just wanted to say that I'm really excited to be here. It was touch-and-go at the moment, and I think it's really amazing, this conference. It's the one conference that I get all year where I come and a lot of people tell me a lot of things, and I get a lot from it, so I appreciate being here.

So that's me. I'm the group chief technology officer of Hiscox. We are a specialist international insurer. We write about £3 billion in premiums across the world. About 3,000 employees, growing rapidly. It's not particularly interesting. The interesting thing is hopefully my talk today.

So it's called "The World Belongs to the Discontented," and it's an Oscar Wilde quote, which, to be honest, I'm not an intellectual. I'm not a cerebral powerhouse. I'm an Essex boy that watches Love Island, so I pick up other people's quotes and use them at will.

I first heard this, actually, when I joined Hiscox six years ago, and our CEO at the time said these words. I found it really interesting, and it really resonated with me that these guys that are on my exec often quote this. These are guys in their 50s. They probably shop at a different supermarket than I do, if you read between the lines.

What is the thing that's getting them out of bed still at 4:00 in the morning, flying across the world, working really hard when they probably could retire several years ago? And it's that discontent and agitation that really inspires me and that I find really interesting, and I think something that's helped with my own career path.

Now, today, this is my third year back at the DevOps Enterprise Summit, and I started in year one. I talked about the change, the development organization that we had. Year two was more focused on ops, so move to the cloud, Agile-ification of our infrastructure teams.

And I said to Gene that I don't want to come back and just spout more of the same. What can I come back and talk about? So he said, "Why not talk about your career path and the challenges and the opportunities you've had in your career and how you've got to the role that you're in?" Which I was a bit worried was going to become really a self-indulgent conversation where I talk about me for 30 minutes, and I come to about philosophies, and was a bit worried I end up talking like a certain individual.

So hopefully the next 20 minutes doesn't go a little bit like this.

"Right. Would you like to tell me about your individual outlook on management?"

"Sure."

"David Brent is refreshingly laid back for a man with such responsibility."

"Yeah."

"Can you just answer in your own words, and I'll work it out later."

"Yeah."

Brent mused.

There's a danger. I'm very worried, so just throw something at me if I get Brent-y at you.

Let's rewind the clock. I talked a bit about my upbringing and where I started. So when I started infant school, I was a bit naughty. I was a bit of a bully. I couldn't concentrate. I was a bit of a shit, to be honest.

So my parents did the right thing. They sent me to a very traditional private school. There were eight people in the class, which I was firmly at the bottom of that class, out the row behind. They were really just trying to sort that naughtiness and to whip me into shape.

And when I reached senior school, I got sent back to a normal state school. Unfortunately, when I arrived, I was just perceived as the posh kid, even though, again, I'm just an Essex boy, but I'd been to private school and everyone else knew each other, had their social groups formed, and I was kind of the odd one out.

I can remember very distinctly the first month of coming back into school. When the teacher would walk in the room, I'd stand up to attention, as we all did in private school, and the other kids are going, "What the hell are you doing?"

I was never in the cool gang. There were all those pre-formed groups. Again, I was never the cool kid. Bit of a geek. I'm sure I'm in the right audience to be talking about becoming a geek.

And my first crush, I can remember from seven, Sophie Miller. Seven years old to 16. She never even knew I existed, I don't think.

And I always felt like I was the wrong side of the velvet rope. So you know when you're in a club, or you get on a plane. In a club, you see people go to the VIP section, or you get on a plane, people turn left and you turn right, and you're like, "Well, why aren't I part of that lot?" That really pained me for a long time, which resulted in a couple of things.

So first of all, this desperate desire for acceptance and to be part of something, and also to show the world that I had some self-worth and I could contribute and I could do something meaningful.

And I think, for me, I became very self-analytical and self-critical, but I think probably in a good way. So I was always like, "What can I do? What can I improve in to help me get into that club? How can I join this elite that I'm always excluded from?" And always trying to push myself forward.

And that just general agitation and wanting to be ambitious and to move forward was actually set by a lot of those earlier things, and those earlier crushes, and earlier being excluded, and being on the outside.

I'm missing a slide. Never mind.

So stepping back through my career, I just wanted to talk about some other jobs. So this isn't it. Missing a slide. But my first job, I turned up at a media company, and it was an advertising agency. I was 21, out of university. It was in the dot-com boom days, so loads of money flying around.

I used to turn up at 10:00. About 11:00, 12:00, we used to go for beers that lasted three, four hours. I maybe did 30, 40 minutes coding in the afternoon, then I finished and went down the pub again. I thought, "Wow, this is what work's like." You party all the time. I was surrounded by models because it was an advertising agency. I thought, "This is amazing. This is what work's like."

Really wrong.

And then I left that and I joined this organization. So I went to work for a hedge fund. I became a webmaster. Can you remember that job, webmaster? I thought, "Wow, that sounds cool. Master. That's a cool job."

I did a lot of stuff around sysadmin, and my mood there, my emoticon, was like, "Oh, sugar, what have I done? People are actually making me do work. I have to wear a suit. I have to wear a tie. This is not good for me. This is not a good fit."

My learning really there was the cultural fit as an organization was really more important than money. I left for a massive £2,000 a year extra. So forget the models and the beer and all the lunch. I mean, for two grand extra. So that's a lesson. Don't do that again.

Job number three, I went to work for a media company, and my job, I was a technical project manager. Never done any project management in my life. I learned some project management, obviously, out the back of that.

My mood there was that of tears. So massively out of my depth, enormously out of my depth. Didn't have the technical skills. Didn't have the leadership skills. Didn't have anything. I was still a developer in my mind. Didn't know how to operate.

And two key attributes of things that I learned there: one was about micromanagement, one was about trust and vulnerability.

So micromanagement, I would do things like poke people on back every 20 minutes. "Is it done yet? Is it done yet? Is it done yet? Have you done it? Let me review your code." That's how I operated. That's the way I thought I would control teams and trying to get stuff out the door. The more I poke them, the more I crack the whip, that's more stuff that's going to get done.

Again, people get frustrated by that, and it's not the way to win people over.

And the other thing was about transparency and vulnerability. So the business used to come in, and they'd go, "Well, Jonathan, what's the latest status of the project?" Knowing that it's a complete and utter mess-up, I'd be like, "Yeah, everything's fine here. Nothing to see. Nothing to see." It's like that duck, calm above the water and legs flapping underneath.

And all that ever did was catch me out, rather than saying, "Look, we've got a load of problems. We've got stuff to sort out. Here's what I'm doing about it." I would effectively, well, lie, really.

So that transparency of the way I operation: you can never be caught out if you're transparent, and no one is ever going to give you a hard time for being brutally honest about where you are and what you're going to do, as long as you're moving the thing forward. But that's another key lesson of mine, transparency and vulnerability.

After that, I moved to another organization in financial services. I call this Shouty McShout Shout Corp. I was a technical architect there. I was there for five or six years and doing a lot of very enterprise-grade infrastructure and engineering work.

Strange place. It was staffed a lot by ex-policemen, ex-army guys. A real culture of he who shouts and swears loudest gets stuff done.

So if I wanted to create a new service, move something into the cloud, whatever those things were, you influence people by being harder and more aggressive than they are, and that's how you go through the ranks. And that is lined up all from the top. That message all applied from all the types of people that the big boss recruited. That message that went forward was that aggression and power and dominance, that's the way to win.

And what happens when you do that is that blame culture and aggression. No one would ever put their hand up and take a risk. No one would ever try and implement something new.

Well, first of all, a change request took an hour and a half to fill out the form. So I'm not going to do that for a start, and I'm definitely not going to do it if it means me getting chewed out in front of the entire office.

No one's going to take any risks. So the platform never moves forward, and then what happens after five or six years, you have to scrap everything and start again because nothing is incrementally ever done, moved forward.

But I did learn again. My role there was infrastructure. It was engineering, obviously a bit of development. And actually, I started to carve myself out into a bit of a niche. So being able to do lots of different things before the word T-shaped was developed, that sort of got me a good mood there. But my mood really was that fighting. Essex upbringing again. That's the way you move forward.

And then I landed in this job. So I've been at Hiscox for six years. I started as a rank-and-file solution architect. I was doing lots of upgrades of systems, fairly normal day-to-day stuff. But I got really agitated very quickly.

So after three months of being there, I was like, "Why are we manually installing stuff at cost, and we're paying a vendor to come and do it at £50,000, £100,000 every time? Why have we got different teams that do different things?"

So I'm a developer. I hand it to a build team that hands to the deployment team that hands it to a test team that then goes into production. I'm like, "That's just insane." The number of handoffs and the work required to do that. Everyone's finger-pointing because you did it, and there's all that blame culture and pointing at each other. Didn't work.

So I started very early on, sort of after three months, they're like, "Who's this idiot? Go back and do your day job." But trying to say to the head of architecture at the time and the CIO, "There's this thing. It's called DevOps, and here's what it looks like, and it's something we could do, and we need to restructure our organization."

And that was months and months and months of influencing and trying to get this thing moved forward. And out the back of that, I got a role as our DevOps lead, or head of platform services it was called, and we created a center of excellence that helped drive out some of those ideas, some of those processes, some of the concepts around the organization.

So what I've typically found is a lot of the teams are so close to doing day-to-day development or day-to-day infrastructure, there's not much time for them to put their head above the parapet and go, "Look, there's a better way of doing stuff."

So really, this team is to try and help enable others, not to do the work, not to do the deployments themselves, not to create the automation, but to teach, coach, and really help others to push the needle. And that worked out really nicely.

So that was a big success. Lots of business value that I've talked about in previous years, I won't repeat now.

But last year, I was made interim CTO. I did that for a year, and two months ago, I was the full-time CTO role. Go me.

Round of applause. Thank you.

And really, I think what I've learned is this leadership. All those thousands of mistakes I've made, and I have made a lot of mistakes over my career, have led to this point that lets me get to do this job.

So some other lessons I've learned at Hiscox. Again, back to my natural style, and I think something I really learnt at Shouty McShout Corp was trying to influence people. What I typically do is I go, "Right, okay. I've got an idea. We're going to move our servers to the cloud." Someone will go, "No, I don't think that's a good idea." "I think we should move our servers to the cloud," would be my response. I just repeat the same thing back in the same way, but louder, right?

And trying to find plan B or C or D or E is a skill that I'm developing or have improved on, but again, back to my natural style. It's about dominance, and it's about pushing and being more aggressive because that's what I had learnt at Shouty McShouty Corp, right? That's how you influence change. That's definitely not what happens at Hiscox. They're all different types of people.

There's something about employing brighter people than yourself. So back again, I talked about a media company, about transparency and trust. I would, early in my career, have thought of that as a risk to me personally, or they would show me up, or that I need to be the brightest person because that's going to help my career and that's going to help me move forward.

But actually, as you go up that tree, you need to deliver through others. So you need to have a lot of people brighter than yourselves, and really my role changes from telling them what to do to them telling me what to do, and I just become an enabler of the change. So again, that's another lesson, to take that ego and arrogance out of the conversation and deliver via others.

So really what I want to do with this, guys, is just set the boundaries and the context for the way they work. So what's the outcome that I want, the constraints and boundaries that they roughly have to live within, and then just let them get on with it. And it's really as simple as that.

And I think I've heard some other people talk about good leadership styles, and I think that's one thing that I do, is just let people get on with stuff. And it doesn't mean that I don't care, but you need to empower and support them. It's very different from micromanaging, finger-pointing, and being in all the action all the time.

So my role: I report to the group CIO, and I have a number of peers. So I have a group role. Hiscox is a fairly federated business, so there are a number of heads of IT for each of our business units across the world. And there's some roles that are at a group level, cover all of those. So I'm in that group CTO role covering the world.

This is a slide taken from a Gartner research piece that came out recently, and they didn't produce this slide, but it was textual-based, but I've just done it as a slide to be more easy to consume.

So there are lots of different types of CTO, and I think I'm a technical, technology innovator type. So things that I commonly do are help govern technology use. I've helped define the IT strategy, some thought leadership. And that's kind of where we are now, and that's what the role needs to look like.

In the future, I think that needs to shift left, so that'll be much more of a business-led innovation role. My ambition is to make that a board-level role and really help drive business strategy. And with digital, there's a chance there really to get a seat at the top table and to help move that forward.

The truth is, I think I may have reached my talent threshold, but I think I'm the right CTO for now. The right CTO for tomorrow may well be someone else, but let's see how I get on.

So really, my role is about three things. So monitoring external things that are happening in the marketplace, particularly in business and what's happening with fintech and insurance. It's the internally focused side, so how do we make IT deliver better? So Agile, DevOps, all that kind of good stuff.

And then the alignment of those two things to make sure that we're working the right things and we're doing it in the right way. So it really is a highly business-visible role, both internally and externally. It's mid- to long-term focus rather than short-term focus that some of the heads of IT are looking at.

And I want to switch that from being, at the moment, probably 75% internal IT focus and 25% business, to flip that on my head, so I'm doing more business than I am IT. Again, that's going to evolve. It's going to evolve. Every company seems to have a different CTO and work in a different kind of way.

So I often relate leadership style to becoming a parent, and a lot of the things I guess my parents did for me, until I became a parent, I didn't really understand what they did.

So the same when I became a CTO. The things that he protected me from and the shit that he had to put up with on a day-to-day basis, I'm like, once I got the role, this whole new world opened up, right? And that's a really interesting thing that I found from a development point of view, is not taking various assumptions around what your leadership are doing because they can be put on a pedestal and you, "What's that guy doing over there?" But actually, they're protecting you from a whole world of stuff.

So back to that parenting point. I don't think good leadership is terribly different from good parenting. So for me, a lot of it's about education, the way my parents educated me. So why is your transformation important? The most important question you can ask, I think, as a CTO is the why. The why is the really important thing.

I get the team funding. I set them up for success. Again, my parents went out to work. They got me money to be able to go and send me to school and feed me and all that kind of stuff. The same being a CTO.

And they gave me boundaries. My parents gave me boundaries. Said, "Look, we're pretty relaxed. We can do most things, but these are unacceptable behaviors. Here's the constraints of where we want you to operate."

And they were role models themselves. They exhibited the behaviors they wanted me to learn and exercise myself.

Things got tough, they were there to protect me. So scraping my knee, bad day at school, bad school report, whatever those things were, they were there to protect me from those things. Same goes for your team. It's filtering the noise down to your team.

But also then when they do succeed, is to push them to the front and celebrate their success when things go well. So how many parents have you seen that when their kids win at sports, they go, "Yes, I funded them. That's my win." You never see that, right?

So I always step back when the team do well. It's about stepping back and pushing them into the light and helping them get the exposure for their great work.

When I joined, I had a certain level of perceptions about what it would be like to be a CTO. First one is I'd have to wear very nice suits. I'd get wined and dined across London and travel the world. I'd be a blue-sky thinker. I'd be like, "We're going to do all these amazing things. I'm going to draw some pretty pictures and come up with some great words. Go execute." That's what being a CTO is, right? Nice suits, nice dinners, blue-sky thinking.

Most of it's great, but the reality is actually somewhat different. So herding cats. I operate in a federated business trying to pull nearly 1,000 people in an IT department in one way. Very difficult.

Trying to explain to the business why you need to change and transform. Very difficult.

When you're driving that change, again, having the team beneath me helps me go and execute that. But I think with anything, with transformation, again, people talk about the need to change, people being the hardest thing. I spend 99% of my time talking to people, trying to influence them, trying to explain to them why we're trying to do something.

I think that speaks for itself. It's very easy when you're in the day-to-day that I've got a business want me to go and change the website, want me to go and do something. Why do we need to go and do this new thing that's not going to happen for the next three or five years?

So coming up with a lot of new ideas, trying to push the needle on something that might not be fundamentally broken, but you're trying to make things better. There's a lot of pushback on that. And actually, when people go things like move to the cloud, or we come up with this thing called Agile, like, "What the hell is that?" You're a target, really, for people to throw stones at it and go, "That's never going to work."

You need to be quite resilient for that.

And the other thing is, sometimes you just need to ask and beg to do stuff. I have to get budget. So I have a group budget, but effectively that's paid for by each of the heads of IT. So if I have to go and demonstrate to them across a number of people where I'm going to spend the money, how it's going to deliver value, that's a really hard thing to do.

And trying to influence that and drive that change, sometimes I'm just like, "Please, just let me do my job and move forward."

I want to talk a little bit about my personality type. So you might have seen the DISC rating before. So there's four quadrants that determine what type of person you are. There's no one person's better than the other. These are the common characteristics that make up people.

So there's dominance. So I talked about this already, the direct, results-orientated person. The top right is very influencing, so outgoing, enthusiastic, lively. The S, which is steady, very easy, accommodating, patient. You're humble. You're probably quite a nice person if you sit down in that steady box. And the conscientious, who's very analytical, reserved. A lot of people probably sit in the C box if you work in IT, I would say typically.

So I sit as far as you can in the D box, and I don't say this out of a badge of honor, but I say this to show you how hard I find it personally to work in an organization where you've got four different types of people, and I'm the furthest one moved from all of the others.

So that's a massive development point for me, is being so far as a D that I find it very hard to relate to people that are maybe deep S's. And how can I develop the skills and the EQ to go and talk and influence those people?

And actually, people that are in that D box where I am, they're commonly associated with a certain type of people, which are psychopaths. Which, again, I say that out of shame. This isn't a brag. I say that out of shame.

So am I driven, or am I a psychopath? I would hope I'm driven. But again, it's about trying to understand where your weaknesses are and what I need to do to improve, to meet the needs and to be able to influence all those many types of people that operate in our organizations.

So what served me well? I think I understand my own limitations, but I'm actually prepared to do something about them. As I said, EQ is something I've had to develop over the years, and I surround myself with mentors. And basically, I just copy behaviors that I like. So I see things that work well, and I'm like, "Ah, that's going to work next time."

Discontent. People talk about discontent and agitation, and we can always do better. That's very different from moaning. So there are a lot of discontented people, and everyone's got an opinion about how things should be, but it's whether you can actually get up and do something about it. If you are in charge of your own destiny.

And you need to put your head above the parapet. You're never going to move forward in your career if you accept the status quo and can't really drive change through. And you need to put your head above. And it's going to get beaten sometimes, but you have to be prepared for those beatings.

My parents always said to me, "The world is your oyster." I never really understood what that meant. I think I do now, and that's if you don't like something, you're empowered to do something about it. And I don't know who said the quote, but don't be a prisoner of fate. Don't wait for things to happen.

I talked to a guy the other day on my team. He was like, "When am I going to get promoted?" You need to grab opportunities and make things happen for yourselves, not just wait for them to come to you.

And one thing I really like in the people I employ is that agitation. Prepared to push all the time. And if you can't find a natural job, especially in IT, because nowadays, from going to developer, to senior developer, to this, to that, that linear career path, I think is on the way out as we become more T-shaped. That's a harder career path. So you need to go and forge your own career and find your own opportunities and push. No one's going to open that door for you.

I should talk about technology very quickly, as we're at an IT conference.

The point of insurance is to help our customers get back on their feet when something really bad happens. So a lot of people judge insurance as a bit of a grudge purchase. "Oh, it's that thing I legally have to go and buy, and I don't really want to." But our job is to go and help people and help them get back on their feet.

The more that we can understand the risk and understand our customers better, the more that we can help people. I think that's really exciting.

So I've been in IT for 20-odd years. I'm largely bored by technology, which sounds weird for a CTO to say, but I love the outcomes. I love helping people, and I love the business impact of some of the processes and technology that we're implementing. That's the thing that excites me.

So last year, as an example, we had our chief underwriting officer come to us when all of the terrible floods in the US were happening, and he said, "Look, I want to reprocess all of our book to understand our exposure to the floods that are happening in Florida."

That's a billion records to go and work out all of this data. To do it on premise would've taken about eight months to process that. But with two data scientists in the business, a tiny little bit of help to get the data up into Azure, we managed to do that in 12 hours, and it cost £600.

So I just find, as just a little example, the power of Azure is amazing. And I think for those that are operating at more the management level, I didn't have to influence to get a project created. I didn't have to decommission it. I didn't have to invest multiple million pounds in capital. I didn't have to talk about depreciation runoffs. There's no business case, right? It's a totally different world we're operating in.

But that creates further problems, right? Success is the next iteration of that. They said, "Well, okay, Jonathan. That's really cool. What happens if we have 1.5 trillion data points that we can do in real time?" And I went, "Ugh." At one point, we worked out to be able to process that level of data, we'd actually have to take the entire of Azure for about two weeks, which was £361 million in Azure spend, which probably isn't going to happen.

Why is that cool? That's because it's really letting the business open their minds up about what is possible nowadays. I think the business was so constrained about what could be done before that the IT and technology of today is a very different place. The things we couldn't do yesterday, we can do today, and I find that really exciting.

So hopefully, I haven't been too Brent-y. I just want to leave you with a quick video of how Mr. Brent would've finished, and I hope it wasn't too much like this.

[Video clip plays]

"On today's Brent, you can say, yeah. Tear us apart now. Now, now, baby. Baby, I would wherever you please. Well, if your heart could start living now—"

"Yes. Our thanks to David Brent—"

It stopped it. All right. Thank you very much. Thank you.