Bridging Tech and Business: Lessons from a CTO's Craig Mellon’s Transformative Career

Hello everyone, welcome back to Mastering Tech Growth. Today we have a treat. We have Craig, who's a CTO for a law firm. I'm not going to mention the name just yet. So we'll be talking about Craig's journey from, from an individual contributor, AKA developer, to actually a CTO, and we'll touch on his views on what is the role of CTO within enterprises. So welcome, Craig.

Hi, Mike.

So do you want to let us know who Craig is?

Yeah, sure. So I've, I've been a developer most of my life, uh, probably 25 years experience. I started very, very young. My, uh, my father was really into tech, uh, so I got introduced at a very young age, probably probably around 10 years old. We had Commodore 64s and then PCs, and I remember the world before the internet. Again, my father was really into tech. He, if you remember the old bulletin board systems where you used to have to dial up for the internet, he used to run a bulletin board system. So I got into it all really early. I think I wrote my first program on a on a Commodore 64, which was basically reading a 300-page book and typing it out character for character. And it was just a dancing mouse across the screen. But I kind of got obsessed with computers and programming then, which really drove my career in that direction. And then I started my professional career quite early. I left school in sixth form I started as an apprentice at a small company, working in a small team, and then kind of just progressed from there into a professional software development company, then as a junior. And again, through, through my father, he was working at a larger company, and I got offered a more mid-level role, developer role, I guess that would, I guess, quite quite a turning point. Then I thought I kind of made it a bit as a professional developer then, and then just kind of progressed through companies. Originally, as well as development work, it wasn't a cloud or anything like that, so we did a lot of infrastructure as well, building SQL servers, networking. So I had quite a vast range of, uh, using multiple different technologies. And then just kind of progressed. And then a real big turning point in my career was when I was working at a company, we was showing, demoing a solution to some companies. And one of the guys there said, do you want to have a quick quiet word? And he offered me a role of starting a company as a founder, delivering technology solutions. And again, very young, I got offered some shares in that company, didn't really know what I was signing up for. In the end, turned out pretty well. And I was there for 20 years. And we built a small company for myself and him into a company of 200 people. There's about 50 developers, 5 teams, DevOps teams, QA, product, And then we sold it to a big American firm. So worked out quite successful. And I think I learned a lot during that, during that area. And then that's what, that's when I first came into the CTO role. So obviously started off as a developer building a team. And as the team got bigger, I kind of naturally moved into more leadership side of it, managing the teams, managing the direction. And then a couple of years before we got purchased by the corporate company, the, the CEO there did a revamp of the senior leadership team and changed a few titles. And that's where I got me— got my CTO title. Uh, like I said, I've been there 20 years, and after we got bought out, I stayed for a few more years, and then I thought I'm 40, 42 years old, it's probably about time to try some different companies. And so I left that company to again do another CTO role to get some more experience. And that was a telecoms company. And that was, that was quite a shock compared to what I've worked at because I'd worked at this company, I built it up and saw it grow over 20 years. And I kind of, like I said, naturally kind of built into that CTO role where I was. And then as I moved to this other company, there were lots of stuff I didn't know. And I learned a lot from that. It was because I guess the startup company I was at, the CEO, we had a great relationship. He'd got, he had a degree in computer science. But he was great at the business side and I was better on the technology side. But we, we worked really well together. And although I was involved a little bit on the business side, it, it wasn't as much as was expected when I moved to these telecoms company.

Um, so I guess, yeah, where you're now, Greg?

Sorry, where you now?

What, what the company you're working now for?

So now I'm working for a modern law firm. They class themselves as a modern law firm because the way we approach pricing is different to your traditional law firms. And I think the CEO of this company describes traditional law firms as very toxic places, and his driver for this business is to make it a better place to work. So it's a fully remote company as well, and it's all about the— all about giving everyone flexibility, work flexibility, and it's working really well.

I love it. I love to hear that. It's just that new style of leadership which is slowly seems to be getting a much bigger share of, you know, inside of the market. So you mentioned a couple of things, and, you know, I was taking notes. It seems that Along your career, your father was a, a big influential figure for you, starting from 10 years and, you know, up to giving you that mid-level role or helping you to find that role. What, uh, is he still around? Is he still, you know, helping you to think about the career?

Yeah, so he's— he works. So I— he helped me get that mid-level role, and then as I moved and founded this company, he eventually came and joined the company as well. And he's still there now. So he kind of moved, I'd probably say about 15 years ago, he kind of moved away from the technology side and went more into the management side and business side. So, and yeah, and he's still there. So he still dabbles with a bit of programming now and again, but I guess I kind of see it as though I've overtook him now.

I mean, When you've been in the market for so long, you've seen these technological changes and innovation and growth. And you mentioned that pre-internet, you know, technology space is just so different. And I remember myself just, you know, sitting in a balcony, and my dad is, you know, he's a math professor back in Lithuania, you know, which is my home country. So I was sitting, it was like a spring, almost summer, it was very sunny and warm, and I was just, you know, in the balcony drinking tea. And I was, you know, I'm gonna grab a book. And I just grabbed like a random book from, from his shelf, and it was HTML4 book. And I was, you know, just going through the pages, and I was like, I could build a website, like, that seems just easy. And that, that was it, you know. I was like 16, and from that point on, it's, it's all just coding, computers, and tech, which is So what, how life, uh, you know, have these pivotal moments where just send you to that direction. And the question I have, Greg, do you remember that moment where you went like, you know what, I'm gonna leave that hands-on part of my career, which is the coding and the cloud and the servers, and I'm gonna go work with people, you know, I'm gonna become a leader, I'm gonna take that management. Was that a conscious decision from your part, or was it just that because it was your company, you were just doing what needs to be done?

Yeah, I think so. I was thinking about this, and I think it's— I kind of had no choice because the company was growing, the development teams were growing, and they just— I just didn't have enough time to be involved in everything. So I kind of was forced into that. I've got to take a step back ensure everything's on track and provide that direction for all teams. So I kind of, I feel I kind of just naturally went into that role. It weren't necessarily a conscious decision, but I've always found that most companies I've worked at, I kind of always fall into that leadership role. I tend to always end up leading a project or leading a team. And so I think it just naturally grew into that.

That's good. I had struggles with this. So I was, I felt like I hit the ceiling as a, you know, as a coder, as a senior developer. And I've been in that space for a couple of years. And, you know, I was like, what is you know, that next step. How do I go to that next step? And once you develop a certain amount of knowledge within the business and the team, you're getting all the questions and you are able to, you know, provide all the answers. So you sort of naturally become a go-to guy, aka, you know, the leader for the team, and you just lead the team, you lead the projects. And at that point, you know, you're getting that choice to make, you know, do I go and commit fully on leading people, or do I still want to do the coding? And I was struggling for a couple of years on making that call. And one of the big mistakes when I actually made that call was that when I went into that leadership position, I didn't really realize that I need to delegate and just trust the team doing things. So I would tend to gravitate back into doing things myself, which is a very common mistake, you know, a fresh leader is due. So In your position, do you feel like that was something you did, or you were just absolutely fine? You know, you stepped into leadership role and you were like, you know what, I'm just done with doing hands-on work.

No, I feel like I was exactly the same. It's really hard to let go sometimes. And like I said, I kind of got forced into it just because of the amount of work. But I really, I learned a lot. We took on a lot of graduates as the company were growing, so I learned a lot about how to help them and seeing them grow, and I kind of realized I can utilize my skills to help them grow and seeing them, them grow, and when you can see passion in people as well, it's really easy to give them that, just that little bit of direction and let them go off and grow that way. We had a lot of graduates that within 3 or 4 years within the company, they were leading a team and senior developers. They really excelled, and I think that really helped because you've got to let them have that bit of freedom and innovation, otherwise they won't grow. If you're just telling them exactly what to do or getting involved and taking over, they never get that opportunity to grow. So, but yeah, during, during that transition, it is really hard to let go because you always think, I'll just jump in and I'll do that and I'll fix that. And you've got to, you've got to, you've got to realize to step back as well to see bigger picture. And as I said, because the company was growing so quick, like I said, we quickly expanded to 50 developers, there was no choice really. Otherwise, it would have been bring someone else in.

Would you say it was a blessing in the sense that you actually got these graduates to teach, so you almost got like this blank canvas? And as well, you being, you know, fairly young in the leadership role, you had someone who has no expectations of a leader, so you were able to learn, you know, better ways from the get-go versus, you know, inheriting a senior team who have notions of what the leader should be.

Yeah, no, I thought I also, I learned a lot from them as well because they've come from, come straight out of university, they've got all these great ideas and they're, can we try this, can we try that? So I learned a lot about helping them work on different ideas and again, having that, getting past that bit of resistance and letting them go down that route. And there was a— had a great guy who joined us who, he was very passionate about training. And he drove an innovation within our team of running tech talks within company and helped push the newer junior people to, to get up and stand up in front of all the developers and show a bit of new technology and I learned a lot about that because he was so passionate of doing that. And then I learned how that can help people grow and help with their training and progression. So I also learned a lot from them as well. Nice.

Would you think that you being a developer made, maybe made you a different leader, made you a different CTO? So I'm effectively what I'm asking is, is there a difference between a person who finishes an education of being CTO but never was a hands-on developer and goes straight into this management role versus a person like you who went through all of these stages of knowing nothing to junior to mid to senior coder and then becoming a leader?

Yeah, I think it makes a lot of difference as well because it's that experience You've been through a lot of things, you know what works, you've worked in lots of different companies, so having that experience of what's worked, what hasn't worked, with training, with technical decisions, everything, I don't think you can beat that. There's such a vast range of technology out there, it's by having that experience over the years and seeing how different technology works in different companies and different size teams, etc. I think that really helps.

Would you say that it's possible to be a CTO just based on your technical knowledge? So let's say, I see that a lot in startups, and I think you, you exactly had the same. It's like, uh, you have all of these good coders, and, and then eventually, because you have all the knowledge about the systems and are about the product and the code bases, you, you are put in this position, but you never really led people before. You never led, you know, uh, maybe big projects. You never made these decisions almost at the business level, and you just go like, hey, you know, I'm very good with this technology, as a result I'm going to be CTO.

Yeah, no, I think it's— I think, I think you've got to have that business acumen I think because I've always been, I've always loved the thought of running a business. And I always think when I'm looking at technical solutions, how could we sell that? Or how could we turn that into a SaaS product? But one thing I've never been great at is all the other things, sales, HR, all that. And that's where I find, for me, the CTO role was a natural fit. So you was involved in driving the business, helping deliver the business goals. But also keeping your hand in tech, your passion in technology. And I think if you've, if you've just got that technical ability, you've— I think you're going to succeed better as a CTO with that business knowledge as well, because you've got to— it's not just about thinking of a technical solution, you've got to think about how it's going to affect the business. How is it going to scale? How are we going to scale team? I find that a lot with some technical people when they've chosen a technology and they said, we want to do this because it's the, it's the new cool kid, we've got to use this new technology, but they've not thought about what happens if the team grows and we need to bring another 4 developers in but nobody knows this technology, not thought about the consequences of investing to train them up.

I like that.

I think having that business a bit of business background knowledge is, is key because you are in effect helping the business drive forward and deliver their goals.

I love that, that strategic aspect of that role. Yeah, and the business acumen which you mentioned, it's— if you don't have it now and you're thinking about the CTO role, you will get forced basically to learn that. The decisions you're making is not going to be all about the developer experience and, and, you know, onboarding the technologies, that there will always will be a question: what is the return of investment on that decision, you know, or which trade-off are we, we making? And it's at the end of the day that business argument is about making more money as a business, and, uh, you have to weigh in that into all the decisions you're making as a CTO. So we're basically saying that just having the technical skills will probably not be enough to, to, you know, to sit in a CTO role, or at least do that role well. Is that, is that correct assumption? Another assumption? Is that correct conclusion? Right. Okay, cool.

So that's what I think. Yeah.

All right, so, um, do you encounter this, like, when you work with your own team? Let's say you have maybe your tech leads or maybe your head of engineering and you and, and you see the lack of that business acumen. It's like, how do you go— like, you're not thinking about all the things you should be thinking in this role. And if you want to advance, like, this is how you should be thinking. Like, how you even approach getting these skills into people so their career can progress?

I think that's, that's quite a difficult one because some, some technical people want to stay in that role. And I think to me, this is where the principal developer VPs come into place. There, you can still be at the higher end, but you're leading the technical decisions, but not necessarily get involved in business side. But what I found is, I think, from a, from a CTO point of view, if you, during your communication with your team, if you're telling them about how this is going to affect the business, how it's going to help grow the business, and we're going to choose this solution because it will help scale and it'll be cheaper to scale than this one. I think if you can start setting a few seeds like that, that helps as well. Like, if you get them involved as much as you can on why we're doing this, I think they start beginning to start to see that picture of, oh yeah, we need to think about this. It's not just about 'Choosing that technology,' or, 'Because this one's cool at the moment.' You've got to think about other things.

Okay, so it's just basically going and asking the questions. Once they come to you with this idea, they want to push forward with an initiative, you effectively just going like, 'Let's take our knee. What about this? What about that?' And you're giving those challenges back, which is a lot more strategic, a lot more business acumen driven, that forces them to go and answer those. And as a result, you start teaching them to think about these.

Yeah, definitely.

Okay, so you mentioned VPs. Did you mean, uh, as like a vice president of engineering type of roles?

Yeah, yeah.

Okay, so in your view, VPs effectively are less business leaning and a lot more technical decisions leaning. So they don't really need to think about, you know, that business argument we mentioned. They need to think more about longevity of a tech, maintenance of a tech, scaling of a tech. That, that's— is that, is that correct conclusion?

Yeah, I think, I think it's more, it's more 100% technical leadership focus and A VP probably works alongside a CTO, and that's their connection. The CTO's got enough confidence that they can lead the technical side.

Okay. I always thought about VPs as less technical and more like people and external factors facing. I don't know why, but I remember when I was thinking about myself and my own career, I looked at VPs and I was like, Okay, so they are, they are a lot more with clients, a lot more like people-facing, you know, a lot more presentations and internal and external influence. I always thought about like less technical. I don't know why I do. Okay, that was just my understanding, by the way. Uh, well, I misunderstood that role. All right, so you did a lot of coding, right? And, uh, From your perspective, you sort of were forced to make that choice, or not even make the choice, you, you were just, you know, brought into that coding. Uh, once you were in that picture, did you ever thought about, that is not my role?

So the, the CTO role?

Yeah, the CTO role. Yeah.

No, I don't think I ever thought that, because I think, like I mentioned at the start, I've always always had a desire to run a business, always had that entrepreneurial thinking behind myself. So, like I said, I found it as the perfect middle ground of being involved in the business side but still being able to have that passion for technology.

That's actually quite nice. A lot of people during interview process, when you have conversations about, you know, what what roles would they like, why they leaving previous business, you get a lot of these like, yeah, I was, you know, either wrong environment or bad role, just couldn't, you know, use the skills or utilize the skills I have. So it's, I think it's underestimated how, how good it feels to actually be in a role where you can feel good and excel in it. So that's, yeah, it's just good to hear. Do you have any like, uh, What, what— so we're concentrating on that business which affected you, Guru, because that's like a lot of your career. So potentially these questions apply to, you know, to any of the other businesses you, you tried in. But did you ever had these situations where you have your direct reports and you're having maybe your one-to-ones on casual chat and you just realize that the environment you have is probably not the best for the— for that person?

That's a very good question. So I think, I'm trying to think back, I think I have, I've had some situations where some people have kind of naturally grew and got to a point and they thought the only, the only way forward is to go into a managerial role or a leadership role. And then when they've made that jump, they've realized it's not for them. Like they're really struggling to do the one-to-ones or really struggling with that interpersonal communication between the team. And yeah, I think I have had on one occurrence that, and we kind of reversed that role back to just a senior developer. So I have come across that, yeah.

Which means, you know, the leaderships are not necessary for everybody. Because I think like this is misconception as well. When people reach a certain level, such as like senior developers, you know, they feel like, okay, well, the next step is to become a lead and, and take on people, which is not necessary. You can still continue being a domain expert with a certain tech, and, you know, salary-wise, challenges-wise, it's going to be as challenging and as rewarding as well. And to give you context, Greg, you know, that question is actually coming from my brother who works, you know, in an environment which I feel like he's not resonating well because of just the environment itself. And, you know, he's a person who just needs different leadership. And that's where, you know, my question was coming from, because that cultural fit is a real thing. And when you get that answer, it just feels nonsense. I myself got that answer in some interviews and I was like, what is this? What are you talking about? But once you start building teams yourselves, when you start hiring people, you know, it's a very real thing to be a cultural fit and to be not fit for whatever is the, you know, business culture. So talking about this, when you do interviews, Greg, what are you looking for? Do you look for, like, to have your own style of going like, this is a good candidate?

Yeah, I think over the years, because I've worked with so many different people, quite a lot of experience. And sometimes you can just tell, like, if you're having great conversation and you're talking about technology and solutions, you can, you can kind of just pick up sometimes that that's a great person. They're going to fit in really well with the team. They've got the technical knowledge, the passion. And I always find recruiting for juniors as well and graduates I always feel pretty confident with that because I've had a lot of experience working with them. And it's not— one thing I never really look for is the experience with juniors because I'm not expecting them to have any experience. It's always look for that passion and the ability to learn. You can just usually tell when people are talking to you that they really love it, they really want to learn about something, and I think that really helps with recruitment on that side. So we have just been through a recruitment phase where I am, we hiring some junior developers. We had over 1,000 applicants for the role. I think I interviewed, we did 30-minute interviews with about 30 or 40 of them and then progressed through to an assessment and then a face-to-face. And the variety of people there was unbelievable. There were some people that were self-starters, done a boot camp. There were some graduates in there, and you can really tell the difference between the different types of learning and where they've got to.

I love that, that hunger element of like, I want to learn, you know, I want to experience things. That's, that's something I look for as well. And I, you know, I'm a strong believer for, for looking at the soft skills, or I mean, they call soft skills, but it's just like communication, understanding, you know, what is the team, how team works, how to be a good team player, you know, teaching others and, and all of that first, and then looking at the hard skills second. Because the hard skills are quite easily teachable. Like, if you have someone who's a domain expert, you're just gonna, you know, pair them up for like 3 months, and, and, you know, if you are a coder, you will pick up any tech quite, quite quickly. But it's very hard to teach character traits.

Yep. Yeah, there was a great example during the interview as well. There was one person was really struggling with the assessment but, but they reached out and asked for help. And they were saying they were so scared to reach out, they didn't want to look like they'd not got the knowledge. But I said, no, that's, that's fantastic. That's what we look for. Don't be afraid to ask. You're a junior, you're going to be learning. I'd rather you come out and ask rather than sit there worrying, trying to sort something out.

Yeah, I don't know why people tend to cage out on this one. We actually had a quick chat with Rob Vaid, who's one of other episodes, you know, where he as a CTO, he's like, I'm always acknowledging what I don't know. And I just go like, I have no idea about this, so I'll need everyone's help to make the right decision. But on opposite, a lot of people somehow are afraid to say that they don't know, and they try to, you know, navigate the conversation or even the situation by not showing that they actually don't know. Which often comes back and just doesn't work out.

I think I've seen a few quotes along those lines, where he's, "The smartest people are the ones that admit the bits they don't know." And I think that helps with technology teams as well. It's like, I'll have no problem saying to the team, "I don't know about this." And I think that helps them as well to say, "Yeah, I don't know about this." Yeah, leading by example, isn't it?

It's like if you acknowledge that you don't know something, they're probably getting this, um, freedom to acknowledge they don't know something as well.

Yeah.

All right, so usually talking about asking questions, so when you stepped into that CTO role, uh, and that was your first CTO role, so you transitioned from the developer to CTO, did you encounter any like resistance or skepticism, maybe from your peers, maybe from colleagues, maybe from, from people you are managing, like any doubt in your abilities to lead?

No, but I think I was quite lucky because obviously I've been at that company, I was a founder of the company, and it was, it was only probably 15 or 16 years that I kind of took the CTO role. So I'd already been there and they'd seen me build teams up and I guess I kind of built that respect up with people, so I never had any resistance or anything like that from anyone.

I think it's probably your skills, Greg. It's like, even if you've been in the business there, I think people would have came out and went like, you know what, Greg, there's some situations around you where you need to upskill. You know, it's usually that what happens. So I think it was calm waters is probably because you did great in that role. So, okay, so no resistance, no challenges. Um, did you ever feel overwhelmed or under a lot of pressure in a CTO role? Maybe, you know, when the business, uh, scaled up very quickly and you guys— maybe when we were selling, you know, maybe in some other roles, but there's often these high-stakes situations which we're getting put in, you know, uh, to make a decision or make a, you know, big plan or whatnot. Like, emotionally speaking, did you ever feel overwhelmed in the CTO role?

I had quite an overwhelming experience when we got purchased by an American company. We flew over to America and found myself in this huge boardroom with these hugely important CEOs from this huge corporate company and that was very overwhelming. I kind of thinking in the back of my mind, am I in the right place here? I'm nervous. And so that was an experience, and that was one time where I did feel very overwhelmed.

And was that a presentation or just like a casual roundtable conversation?

Yeah, because it was, because we'd just been purchased, they wanted our senior team to go over there and meet everyone. And we was, we was planning to roll out our product in America, so obviously their, their leaders wanted to know about the product and know about the leadership team behind it. So, but yeah, it just felt really overwhelming.

How did you deal, how did you deal with that? Is that just like breathe, breathe, Greg, in your mind? I was like, did you do anything specific?

No, I guess just try not be nervous. And I, like I said, I had a great, great partner, the CEO of the company. We'd worked a long time together and he was fantastic at managing situations like that. And he really helped, like, he'd drive a lot of the conversation and then bring you in, into the conversation. I would say he was really good at protecting you from that.

That's good leadership.

Yeah.

Okay, so if we, if we reflect on, on your journey of going from effectively zero to hero, do you think there's, um, a, you know, like a, a crucial skill to your success which you would, you know, cherry-pick out and go like, because of this I was able to do these things?

I think it's the the passion and always wanting to learn. I live and breathe technology. I can't help myself. When I finish work, I'm sliding through Twitter, reading the latest trends. And I think a big thing I always do as well, I always reason about things and I'll spend a lot of time thinking about it. And I won't just jump into a, jump into a fad or a trend. I'll really think about it and consider it, even trial it, play around with it before making decisions. So almost like a— I don't know how to describe it— almost quite reserved in decisions.

You need an extra— how it's called? I think from psychology perspective, it's called a reflector, where you sort of like need to take a lot of information and then just sort of reflect on the data points you're getting before you make a call. Is that like a correct assumption? Yeah, I remember I did a couple of tests as part of some interviews where they go like, oh, this is, this is how you think. And I remember that reflector being part of my answers because I do the same things. Like, I mean, decision velocity is quite important in, in all, you know, our roles. But at the same time, like, I want to cast a huge net, get a lot of inputs, and then sort of reflect on those inputs before, you know, I make a call. Does that sound like, like you, Greg, as well?

Yeah, definitely.

And, uh, so you mentioned that, you know, after work you're doing more work, and that's me as well. And I, I remember I got these questions in like one interview, and they were like, what do you do on, on your free time? And I'm like, I do the same. Like, it's like, you know, I just love tech. I love what I'm doing. Maybe you will like it like that. Maybe you will like it like that, right?

I'm still very, very excited about it. When I see an article on LinkedIn or Twitter, I can, I can sit there and read, read for hours and start getting excited. I start thinking, you know, could we use this in one of our products?

And Okay, do you think the market is not paying enough attention on leadership and soft skills? So because you mentioned, you know, the articles, and, and, you know, I get— I have my own sort of feeds as well. So it's always some type of tech, some type of, uh, you know, problem solution, uh, placements and whatnot. But very rarely do I see a real takes on like people management, leaderships, and soft skills like communication. You do see them, but Percentage-wise, I feel like it's just like maybe 1 to 5.

Yeah, no, I agree. And growing the startup company I had, there was no formal training or discussion about management training, communications, or anything like that. One thing I did find when the corporate company bought us, they obviously had a lot of training in place and a lot of the team, it was the first time they'd ever been introduced to a management training, and you don't— you still don't see it a lot in companies, and I think it's really, really important, especially for helping what we discussed about before, someone transitioning into a management role. You've got no experience with it, sometimes you need that little bit of help and and training.

I think you need—

yeah, everything's so, so much tech and tech focus, you don't see it as often.

That's a very good shout, and I, I fully agree. Like, that, that especially that transition, if you, if you, if you make that, you know, lateral jump where you have a, you know, you have a one career path which is all tech, which is all hands-on, and then you make that lateral jump, you go like, I'm going to manage people, like Once you make that jump and you make that decision, it might be a wrong decision. Maybe you'll come back, as you mentioned, with some, you know, some situations you had. But if you stick with it and you made that jump that first year, any help you can get where people actually teach you, you know, you how to do one-to-ones, how to communicate, how to delegate, all of these skills you likely don't have when you were doing hands-on coding. And these skills are very important for you to actually do good leadership. And now you're responsible indirectly, uh, for, you know, for work which is coming from like a lot of people. Maybe you got a team of 8 or 6, or maybe it's more. So doing these things correctly is actually a very valuable skill. And, and you're right, the training for that— I personally never seen in any organization where that is a module you get when you make that jump. But maybe it exists.

But, but yeah, I've, I've noticed I've recently probably about 6 months ago, I enrolled on an academy called CTO Academy. And they have a lot of their sections about people management, leadership, how to manage your team, and which I wasn't expecting, because it's a CTO Academy certificate. And so that was quite surprising to see. But great, I think it's a great skill to have and you need to learn it. So really pleasing to see that in that CTO course.

I think I know them. They literally CTO Academy, isn't it? Like if you put it in Google, it would be CTO Academy. Yeah, yeah.

I think it's a really good, really good course for CTOs. I never had a university degree. I was self-taught. I left school early. I always wanted to do a university degree. I can't get my words out. I always wanted to, but I was so passionate about developing, I just wanted to put all my efforts into that and get working. So when I came across CTO Academy, I was really excited about it, and I've been loving it. The best thing is the community. I've been able to talk to other CTOs and realize you're not on your own. There is other people facing same issues as you are. And, and I've recently started attending some CTO roundtables as well, which again, fantastic. It's just really helpful to just chat to other people in your position and learn from their experiences as well.

Good. I love that. I remember when I started doing that, same feelings. It's just, um, maybe it's just a power of network, or which is underestimated by a lot of people. Just having other people who are in your roles, or maybe a little bit higher, where you can just go in and have chats like roundtables, which is community in general, and go like, here's, here's what I'm dealing with, what you guys thinking, and you know, you get these ideas coming in. It's just so, so helpful, and it's such a simple thing to, to really do, right? So, um, so if you're getting these external— maybe not validations, but you're getting these external opinions coming towards you— did you ever— we're in a situation where people think about you as a CTO in certain way, and you go like, that's not even my role, like, that's not what CTOs do. Especially from non-tech people?

Trying to think. So I have come across that. So because I think that the title Chief Technology Officer, because technology, I've had people in companies come and ask me to help them with this calculation in Excel. I did think to myself, I'm thinking of the wider picture here, not that low level, but they think because you— because of your title, you're the person to go and ask. Um, and which, I mean, to be fair, I did help. I can't not help. But yeah, sometimes I think them kind of misconceptions about what you are, they don't really see you as part of that senior leadership management role, kind of.

I got this problem with my virus, like something doesn't load. Can you check this, Greg? It's like, no, that's IT, man.

Just—

I get what he's saying. Yeah, okay. Um, so you mentioned the CTO Academy, and you know, I, I know another group called CTO Craft. So there's a, there's a couple of big CTO-level groups which, you know, give that non-formal education, let's say. But, you know, I'm sure the courses are as good as, as going through a formal education. And I know that Cambridge, who I actually live quite close to, has a CTO, um, like Cambridge level, which is like $25K or something like that.

Yeah.

So in your opinion, do you think the formal education is practical in our field, or self-taught is is just as applicable and is just as enough.

Yeah. So funnily enough, I did see that Cambridge one. I did consider that one. I think what attracted me more to like CTO Academy was it was more relevant to the role because I've been doing a CTO role for a while. I knew what was involved and their curriculum looked more relevant for today's CTO role. Whereas a lot of the Cambridge University one was kind of a lot of theory and probably not up with the times of what a CTO role is today. So that's what kind of attracted me.

I actually love that very much. And, you know, my take on mentorship is very similar to this. It's like, you know, here's a huge head in the cloud setup, which is, you know, let's say Cambridge CTO, you know, course, which is very expensive, you're going to get pretty much the whole picture there is to get. But then outside of all of that picture, there's applicability to your current role where you are. It's probably a lot smaller. And you can, you can find a more tailored approaches like, you know, CTO Academy or CTO Craft. And then you can even go deeper and find an actual mentor who you know, does that professionally and, and mentors people. And then you can go like, okay, well, I'm gonna pay you for, for your hour, or, you know, a package of 10 hours, but you're gonna teach me on, on like these things which I need, which is like communication, or, you know, how to run one-to-ones, or whatever. Then you can cherry-pick exactly where you can apply, as in take it and just bring back to your role. Where these big professional educations, you know, like, you don't have that ability. You're just gonna get this bucket of knowledge, which a lot will be likely not applicable at this point in time, right? Okay, I see that, right? So looking back, when you started, any advice you give to yourself? So if you have time machine, you just jump back, hey, younger Greg, don't do this, before you actually started CTO role?

I think it's just don't try and get into it too early. I think you've got to have, you've got to build that experience. You've got to go through that experience of failing, being successful, and don't try and jump into it too early.

So even if you weren't, you would say, take your time, go through these levels naturally, be a junior dev, be a mid-level dev. You know, be a senior there, be a team lead, and then maybe head of engineering, and then effectively take all of these levels. Don't try to just go, hey, you know, I know how to go, I'm gonna launch my startup and call myself CTO. Yeah, okay, I, I can see that. Yeah, I can see that. And I actually had a very, uh, a very go-to— what's the character trait I'm trying to describe? Basically, you know, a person who just so willing to do everything, and, you know, as a result gets a lot of opportunities created for himself. And he was, uh, just maybe like a strong mid to senior type of coder. And because he was so influential with the business, you know, he just came to me, he's like, I want to be a head of engineering. And I'm like, he's just gonna jump over like 4 roles, you know, where I, I can absolutely you know, see you doing well eventually in that role. Let's maybe take a couple of years. And that was, uh, you know, that was interesting one-to-one where you, you don't want to kill the willingness and, you know, kill that momentum, but at the same time you want to explain it well that, you know, it's just too soon.

And he would have had a very similar situation with— there was somebody who was working in a technical documentation role and he wanted to be a developer. And we gave him that opportunity and he was really good, but within 6 months he said, "I want to be a senior developer now. I know I'm good enough." And I had to explain to him, "Yeah, but you haven't got that experience. You need to build up. You need to— you've just seen the best of it so far. You need to experience other parts of it." And that was again like a difficult one-to-one. And like I say, he was very good, very technical. He picked stuff up really quick, but couldn't have expected him to jump into a senior after 6 months. It was his first ever developer role. He'd only seen the good parts of it.

Yeah, that is a very challenging conversation to have because you need to navigate a very thin line of of not, you know, causing that outcome where people just go, yeah, I don't want to do this anymore. Like, you know, you just take them back. You still want to have that momentum and then willingness of them to perform. If I explain it very well that it's going to take some time, there's a lot of, you know, stones to unturn to actually learn and reach that level. Okay, so before we jump into the next topic. We have this question which is in the spirit of the show, and it goes like this: what is one most important thing for tech growth in any venture? But only one, you can only choose one.

I would say it's around making a good decision, not just jumping into something. I feel like, so when I've looked at technology, it's easy to think, oh, this looks fantastic. So getting through the sales blurb and really considering that choice, I think that could easily make or break you as a company.

Don't rush into committing to things without really thinking them through and the implications they might have in the mid to long run. Yeah, I can— when you were saying this, I was like, oh, I remember this role where I came in as a director of technology to, to effectively just fix underperforming, you know, the whole technological part of that business. And it was literally the remains of what you just said. It was, uh, for no reason, uh, there was monolith and microservices there was a little bit of Go, PHP, and Python. There was like Mongo database in one service, then MySQL everywhere else. And I'm like, who was making these calls? It just feels so random. It's just people were, you know, exactly what you mentioned. It's just like, oh, someone come back from like, uh, some, some type of like CTO-level event or maybe a technological event, they get very hyped up on these like new things. And exactly what happened with microservices, it was like a huge buzzword. And yeah, Let's build it, it's going to fix all our problems. And then people start going in towards their journey, and somewhere along the way, you know, people leave who started their journey, or something else comes up, and you know, you're getting pivoted to some different business priorities. And now you have this uncompleted decision who never was fully rolled out to manage, because you cannot just, you know, roll back. And that's actually— yeah, the whole shebang has huge implications. Yeah, and you're absolutely right, you can make or break business. I love that. Don't rush, think, think things through. So simple.

Yeah.

Okay, so, so you have a view of what CTO role is. Can you give us that view?

So I think the, the CTO always the knowledge and experience of technology to help the business make decisions. And it's the, the person that sits in between the, the business and the technology side. So knowing, being involved with the business goals, the vision, direction, and then having that knowledge and experience to make the right technical decisions and direction for technology and being a company.

Should I expect you as a CTO to innovate, uh, or would I expect that for product people to do? Let me define innovation. So it's not only about the tech, maybe it's about the product as well. And when I say innovation is, you know, it's just trying new things, seeing what works, maybe coming out with the ideas which then can be, you know, later monetized. This Would you, would you say that that sits with CTO, or is it more like a, like a CPTO, like a Chief Product and Technology?

It depends what type of CPO you're working with. So I've worked with a couple. I've worked with one who was very technical and similar to myself, always looking at the latest things that are out, always looking at what options are there. And then I've worked with CPOs that have not really got any interest in technology side. They're more about delivering a product for customers. And, but I feel like the CTO has to be a massive part of that because you're bringing your knowledge, you know what's out there, you can read through a lot of the blurb, see what's going to work, what's not. And yeah, I think this, the CTO is very important to driving innovation.

Okay. Would you say that then CPO is a peer to CTO, like it's the same level, or would you actually want CPO to report to CTO?

I'd think they're on the same level. It's just, there's different types. I feel like there's different types of CTOs and there's different types of CPOs as well. And the one you mentioned, the CTPO. Is quite an interesting role because I've always loved product side as well. I always love designing solutions, but the technical side as well. And I guess where I am, I probably am more of a CPTO where I am because there's no product department as yet, and I'm driving product as well. Oh yeah, but I also think, like I say, we— there's different types of CPOs as well.

I would say you definitely are. If there's no product setup, you know, who's driving the product? You probably, you know, it's probably you. And it's, it's almost like, um, I want to say it's a poor man's solution in a way, because, uh, you, you're taking a couple of roles and you just put it in one. And that's usually what happens in a smaller organization, so startup. You just— there's no other choice, you're gonna wear multiple hats. Which are very close, you know, around that responsibility zone. And the product and technology are, you know, it's, it's, it's, it's, it's just so close, especially if you have these, you know, SaaS services or anything what's online. You, you pick on, you pick on that, you know, maybe you're not the best product person there might be, but you can definitely drive that for quite some time before you get like a dedicated CPO.

Definitely.

What if we flip this or look at it from different angles, Craig, and ask a question: can a business go without a tech person such as CTO and be successful if it's a technological business? So let's say you're just outsourcing everything to, like, you know, Ukraine or whatever.

I don't believe so, though. I mean, technology is a massive part of any business. And I've experienced it in a couple of companies where exactly like, say, they've paid another company to do it, but you've not got anyone there with that experience or knowledge to know what they've delivered is any good. So it's— and I've seen it where the product's there, you can use it, but it was a complete mess underneath. And as it started growing and getting bigger, it basically wasted a lot of money on something that's just not going to scale and needed to be redone. And a perfect example, a telecoms company I worked at, they got a really huge legacy system. And they had a person there before I joined as a CTO, so they didn't have a CTO. They started a project, oh, we'll modernize it, we'll create this project and similar to what you mentioned. There's lots of different technologies and services, some Go services, and the solution was quite good. But what they were missing was communication to business leaders. So they ended up ditching that project 6 months after spending a quarter of a million pounds on it. And that was just because communication-wise, the business had got sold this modern platform that we can build, but wasn't told or communicated to the effort that's needed to do it. And if they'd have had that and a bit more direction, another 6 months and that product would be out there instead of just shelved, money wasted on it. So I think you need, you need that person with experience to provide that bridge between technology teams and the business side.

I love that, and I can absolutely see that. Um, and I got hired to one of the startups way back which was literally that, you know, they used offshore company, uh, they got product built, they started to get the product out of the market, and, uh, you know, quite successful, they started adding some real load on the system and it just broke and they were like, well, no one can validate the solutions we're receiving. Are they scalable? And that really opened up that role. Can this be done by a fractional CTO? So if I'm a startup and maybe the startup came to be because, you know, two people came together, one is sales, one is marketing, like they don't even have technical decision. They build something again, maybe with offshore, they have something, it's running. Can they put a fractional CTO to do what you just described?

I believe so, yeah, because especially when you're thinking about choosing a company to build a product for you, businesses tend to go for the cheaper ones but not realizing what consequences. So if you've got a fractional CTO in there or some technical experience in there, they can help you make that right decision and get you going in the right direction.

I love that. Yeah, and I do agree, it's probably better than nothing, right? So if you're saving, you can't have a full role, get someone on a fractional level to still validate what you are receiving. Because at the end of the day, you might get a partner which is very, very good, and you know, they care about longevity with you, but in reality it is a very transactional agreement. You know, you get a task, you get the task done, you deliver the task, you get paid, and, and they sort of move on to another client or another project. So you shouldn't set expectations that I would care for the longevity. You need someone internal to do that. Um, did you ever have challenges as a CTO, you know, when you're driving these decisions which are quite influential in the sense of what tech you're gonna use, or maybe how you're gonna innovate with the, with the product, or just maybe even innovate with technologies. Maybe you want to change like a cloud provider and there's a baked-in cost of making that move, but you know, long run, uh, it still pays out. And you get this almost like a pushback, you know, maybe CEO, maybe other peers on the business. How do you sort of deal with that?

I think it's all about communication, presenting what you're proposing with the right amount of information, not going too technical but showing the business benefits. And again, that's probably where the— I feel a CTO role comes in with a bit of business knowledge, a bit of business acumen, and the technology side. You've got to give, you've got to give the business confidence in your decisions and what you're proposing. And so I think that really helps with them kind of decisions.

What if they still go like, no, like, it's just, just trying to think of a situation where there's no budget, Greg, like, we're not gonna do that. Like, like, internally go like, but this is such a, you know, right decision. Did you ever been in that misalignment where you just want to get something done but the apex of the business is just not listening, or maybe they are listening but they're just not buying into it.

I guess I've been quite lucky because I don't think I've been in that situation. And, and there's— you can always explain what the alternative, alternative is. So it might— okay, if we can't invest in that, then it's going to take another 2 years. We can still do it, but it's going to take 2 years of having them alternative approaches. And like I said, I guess I'm probably one of the lucky ones. I've not really had much turned down, but I think again that comes from having confidence and trust in your senior team as well.

Yeah, I do agree. It is a good perk if you're running your own business that, you know, you're likely not gonna say, you know, you're not gonna get said no because, you know, it's your business at the end. In big organizations, I would assume, because you have so many different levels to climb through, eventually, you know, people go like, yeah, that doesn't serve my needs, and then you get into this, uh, you know, bigger challenges. Let's say you get something done. Do you have, um, something to share, you know, maybe from the business you grew and sold, or some others where you have this idea, a big initiative, you know, you got the buy-in, you execute it, and it had a major impact towards like efficiency or growth or any other, you know, positive metrics?

Yeah, so the startup company was has got a great example in particular. It started a long time ago, probably 20 years ago. I was there for 20 years and technology was just rising, so this was just before the iPhone got released, and we developed a product using the old Windows CE devices with a pen, and we revolutionized the surveying market. So we changed paper surveys onto a mobile device and then quickly progressed onto iPhone as well because of usability. But, but we basically had really good success because we went into an industry of large banks and large surveying companies who were fixed and attached to a system they'd been using it for 20 years. And it took us a long time, but we eventually broke through and just showed them the benefits of how technology can help you, how it can help with mistakes. It's more reliable and faster, and a surveyor can do an extra 2 surveys a day. And we just eventually broke through, and it was a great success. And I believe now in the UK, 95% of all house valuation surveys are done on that platform. That we, we developed.

That's a nice one. That's a good badge of honor to have, to, to change the whole market or to advance the whole market into a better, faster way of doing things. Okay, how did, um, like, do you remember how the decision was made about this? Like, who, you know, what was that, your call? Were you just, again, you know, maybe going through Twitter? I actually Probably there was no Twitter at that point in time, I guess. But how did that decision from product level came to be like, we should be doing this?

Well, it came about because just before I started this company, as I say, I met the owner through demoing some software we developed for a big alarm company. And it was like a piece of software, the first he'd ever seen of that kind, which again was to do with paper forms. We were collecting paper forms and we created an application that got installed on their network and submitted them electronically. So removing all this posting the paper forms, waiting a few days, and he really saw where technology could help. And so we kind of took that idea and just 4 or more ideas, and that's where it came from in a way. It's— we looked at places where we could use that and provide similar solutions and build on that.

Very, very organic process coming from effectively what you were doing anyways and just sort of iterating. Do you have any, uh, conversations with the market, or that just came naturally because you were already doing something in that area? And when I say conversation with the market, like, you know, product discovery type of conversations.

Yeah, so the owner who I met, he was running a company selling mortgages, and his biggest pain point was these huge documents and forms they had to fill in for the mortgage companies. I think that's where— and he saw that solution I was demoing for this other company, and that's where it kind of clicked. And it was like, there's so much we could do, got so many ideas, and that's where the company came around from. People are not seeing vision or how technology can help.

Such a nice, such a nice story, Craig. It's, it's, uh, it's one of these almost like cliché, you know, when you think about the business, just think about fixing your own problems or creating a solution for yourself first. And I think that's in any like entrepreneurial book. It's like, if you have a pain point, think how you can fix it for yourself. So that's one of these where you just went like, I have a business, here's my pain point, let's, let's serve ourselves first. And that was just applicable to the whole market.

Yeah, I think, I think the advancement in technology really helped with that as well, because it was like really on the brink of mobile devices were becoming more important and more advanced. I mean, when we first started out, the— to be able to take a picture on, we had to attach a camera onto top of the device. And then the iPhones came out with a camera that was 10 times better, and that just kind of accelerated, and everything's just in one package. And just seeing Vision 2, we could really utilize this. Okay, and I think there was quite an advancement in technology over them few years that really kind of drove that.

I think talking about advancements, are you looking at utilizing AI or, you know, ChatGPT type of solutions in your current role?

Yeah, very much, much so. I don't think you can look at it really and The biggest thing I've found with what I really love about AI with ChatGPT, Google, Microsoft is just how accessible it is to everybody now. It's— you can quickly fire up a large model, press a button, you've got your own private model, and just start programming against it. If you think back 5 years or so, unless you had a couple of hundred thousand pounds, you weren't ever going to get started on it. You had to put a huge investment in, and Google and Microsoft and Meta have just opened it up to the world, in effect.

Yeah, you're absolutely right. The accessibility of tech is ridiculous right now. I mean, it's probably going to just improve, you know, at least we should hope it will improve, but you're absolutely right. It doesn't take much to have the fundamental tools everybody has to, yeah, to kick off with the ideas.

And the difficulty is just trying to piece it all together now, though. Utilize it for what? Picking out where it can be used efficiently and help out.

That's like an experimentation type of culture. Do you, do you look at, um, at the businesses you work for and you go like, okay, how can we get this, you know, culture of innovation, culture of playing with tools happen? So we effectively, you know, playing with the newest tools and we constantly trying to create something which doesn't exist by just, you know, experimenting and innovating.

So in a lot, a lot of companies we've always drove innovation. I mean, developers are always quite creative Anyway, and whenever there were new technology, we, we always provided time to experiment with them. And again, because we knew our business started from that, we started the business based on innovation, trying something that no one else had tried. So we always made time to enable people to try new technologies, play around with stuff. We did stuff yearly hackathons where over Christmas we had a week just, we just bought some technology and just played around. And I remember a few years ago we were playing with the VR headsets when they first came out. And I think you've got to, if you show people they can have that time and foster that innovation, I think that's a great way to progress with it.

Again, goes back to that lead by example situation. It's don't ask people to do it, you know, send a memo, here's the time, just go ahead, you know, be part of it, try to innovate yourself, you know, lead by example. I mean, it sounds like a very healthy environment though, Greg. It's like I've been in many companies and you sometimes have this where the space is given to innovate and it's really you can sense it's part of the culture, like everybody thinks like that. But then you have different cultures which are a lot more labor-y, and it's just like do, do, do, you know, projects and what brings revenue. And it's really no space to even breathe and take a distance from, you know, what I call business as usual operations and actually think about innovative ideas. So it's good, it's good you had that culture. It just sounds like a very good and healthy culture. So, uh, last one, Greg. I mean, I'm— we've been talking for about half an hour, 90 minutes. So last question, I promise. Um, do you have like last words of wisdom you would give to anybody who, who want to become a CTO, or like aspiring CTOs who are listening to this and go like, you know what, I would like to be where Greg is.

Yeah, I think going back to what I said is build your experience up, go and experience working in different companies, seeing how different businesses work, seeing how different technology teams work, and just get that experience and breadth of knowledge and then decide whether it's for you or not.

Okay, I think the misconceptions which you would like to debunk before we finish off, in a sense of how people think about CTO role? And, you know, maybe they have some belief that is, you know, a lot of money and they can just command everybody or something like that. Like any misconceptions that came along?

Yeah, I think the CTO, I don't think there's a one size that fits all. I think different types of businesses need different types of CTOs. If you're a small startup company or a medium size, you might want a CTO who's a little bit more hands-on and can help drive some of that business. But then on the other hand, if you've got a large company, a large corporate company, I think that takes a different type of CTO. That's, it's got to be someone who's looking over a larger team and probably more on the business side and decisions and budgets. So I think there's not a one-size-fits-all CTO role. I think you've got to find a good fit for your business.

Effectively what we're saying, there's levels to CTO as well. So there's a title of CTO, but then when you zoom into the title, there's levels to CTOs as well. Being a CTO for a startup of 20 people It's not the same as being a CTO for hundreds of people and enterprises, just different skills. Okay, I love that. All right, thank you, Craig, for coming, talking with us. That was lovely. You know, we went probably to like 20 questions, and I hope that didn't feel like an interview. At some point I was thinking like, I'm just asking too much, that might feel like an interview, but, uh, it was a lovely conversation. Thanks for joining, Craig.

Yeah, thank you. Really enjoyed it.

Thank you again.