Rob Bowley

Written By Richard Harding

Rob Bowley explains how a Fractional Chief Product & Technology Officer makes great sense for any startup looking to tap into a wealth of experience, at a fraction of the cost. Rob shares his top tips, the way to earn more money (clue: it involves reading), and why there is no such thing as a stupid question.

Full Transcript*

Richard: I am delighted to welcome Rob Bowley to the technology chiefs podcast. Rob is a hands-on technology leader, a Fractional CTO, and someone who coaches and mentors, entrepreneurs, and startups, helping them bring their visions to life. Rob spans both the Chief Technology and Chief Product Officer roles. Having started as a developer and worked across a variety of businesses, including the LTA.

The co-op and Money SuperMarket Group. Rob, welcome to the TechnologyChiefs podcast.

Rob: Thank you very much Richard, and thank you for inviting me.

Richard: Oh, not at all. So Rob tell us a little bit about what you do and your current roles.

Rob: So I think, I think you described it quite well at the beginning, but, basically I'm been following my passion this year, which is moving back into startups, and particularly where they could not afford a full-time experienced chief product and technology officer. I'm able to come in on a part-time basis where they get all of the value from all of that experience, but without having the cost.

So really interesting. Really, it's, it's being called Fractional roles and it's getting quite popular now. I can't say I'm much of a fan of the phrase fractional though, because I think they're getting just as much value, quite frankly. As they would from, someone full-time. It's just that they don't need someone full-time.

Richard:  absolutely. And you, you get to bring in that wider experience, don't you as well? So yeah. It's like a multiplier, isn't it, for them as well.

Rob: Yeah, I mean, I've got all these years of experience leadership roles and it's, it's very much the case that, that there's a lot of just common problems that, I've been through before. And I've got lots of templates and artefacts that, that I've reused in previous roles that I'm able to just bring in with them.

Richard: Brilliant. So if we wind it back there, what made you pursue a career in technology?

Rob: I kind of fell into it really. I was not hugely academic. I was probably just curious about things. At an early age, I played around making games in basic on the Atari I had as a child. I. But, you know, really didn't have this plan that, that's where I want to go or anything.

I went to university and did a Business Management degree, came out of it, like a lot of people, not really sure, but it was about the time of the first.com boom. So I think fortunately for me, I got caught up in that wave.

There was actually someone in my village where I just happened to be for a few months who wanted to start an online community for villages. And I went and helped him with that.  That was really interesting and started playing around with code again From then went and joined another startup in Southampton and it kind of really went from there.  I’m self-taught basically. So, I taught myself how to code. then my first proper developer role was when I moved to London and joined Lycos. People might remember Lycos, who were one of the search engines before Google come and ate everybody's lunch.

That was my first developer role, and then it just really went from there.

Richard: Oh yeah, that is an old name. I remember obviously AltaVista and yeah, absolutely around at the same time there was Yahoo as well wasn't there, but Google absolutely decimated that market. It's really interesting what you say there, Rob about not really having that master plan and just falling into it.

But having a, I guess an interest from a really early age in programming and tinkering and that kind of is a common theme that we hear quite a lot on TechnologyChiefs.

Rob: Yeah, well, I mean, I've got a heritage of engineers in, in my family, so my, my granddad was a civil engineer. My father was an electrical engineer, so there's probably something to that.

Richard: So, okay, that’s cool. So in your current role, what are your top priorities, that you face?

Rob: I think the interesting thing I'm, I'm finding is, is with early-stage startups, they're making a lot of avoidable mistakes.

They're building things too soon or building too much or building it wrong and quite often as well, especially if they've got non-technical founders, which is where I can add the value.

They've become very beholden to the tech partners that they brought in. They just dunno what they don't know is half the problem here.  It was interesting when I started on this journey, I was expecting to be adding the most value around the kind of scale-up phase or, or sort of seed to scale up. I could really be adding the most value is going and speaking to people before they start building things. And that's the thing, I've been around the houses.

I've done this all before. I've worked in multiple startups, and I've led in multiple startups. These are largely solved problems. There aren't unique things to them. I think that the difference is with the experience that you build over that time, there isn't just one cookie-cutter approach. It's really about how you're able to apply that experience to any particular context and environment.

Richard: if we just pick up on, one of those, which is the, the desire of founders, entrepreneurs to, to actually build too much you know, how, how do you, how do you manage that bit, Rob?

Rob: I think that, you know, there was a good really deliberate approaches to, to do this, and I actually did a presentation. I've done it a couple of times over the last few weeks, but it, but it really does come down to the concept of a minimum viable product.

I mean, look, there's a really great book that's been around it for years called The Lean Startup, which I think is really helpful on this.

And it's just, you know, be very, very clear on your unique value proposition, the problem statement you're solving for your users. Just get to the heart of the problem that you want to solve then, you know, design your metrics around that. Also then for your core feature lists to be absolutely that and, and know more.

I think the other thing is, is building too much, is there's just loads of common platforms out there that you can use. I am running across organizations that have built their own CMS when Contentful has been around for years and really good. Plenty of options for e-commerce and identity as well.

 I just, you know, maybe ironically as a technologist, I spend most of my time telling people not to build stuff either because it's too early and they haven't spent enough time on the market research and the, you know, building quick paper prototypes Or, things that you just don't need to build anyway.

Richard: I totally agree. I, I think the most common problem I find is getting people to stay with the problem and not jump straight to the solution. I definitely identify with that problem, and they just move straight onto the solution. You know, the longer you can stay with the problem and really understand that, and really fix on that the better chances you'll have of, of coming up with a product or service or whatever it is that'll meet that demand.

Rob: Yeah, and, look, this is not just a problem with startups. It's. I've been working in places like the co-op, it was absolutely the same. It was, you know, just massively over-engineered solutions upfront  You really aren't focusing on what's the smallest, quickest thing that you can do to prove whether their assumptions are valid or not.  We're all vulnerable to confirmation bias.

 Part of the challenge here is what are you doing to actually prove it, and following the scientific method. Basically, it is the kind of plan, do check, act cycle or as in startup worlds. In lean MVP world, it's the build, measure, learn cycle, and that doesn't just apply to early-stage startups.

It applies to every single organization I've ever worked in. And, and, as much of it is, is about having the engine of delivery that allows you to do that. So making sure that your applications and systems are really highly automated. They're easy to deploy. There's loads of automated testing around them, and there's loads of tele telemetry, application logging, product, behavioural logging, that that's giving you that fast feedback.

Richard: Brilliant. What technology trends are you most excited by and why?

Rob: It is an interesting question. I've had to think about it a lot. Having worked in tech now for over 20 years, there's not much I genuinely get excited about. Most stuff badged as new is, is really just rebadging of the same things that have been around for a long time.

You think around the world of platform engineering, well, that's what it's now called, but you know, 10 years ago it was called DevOps.

Then SRE came along, and the meaning just gets completely lost.  

I am excited about the recent developments, with General Purpose Transformers like ChatGPT. You know that that has been around for 40 years as well. you know, I was watching the film War Games over Easter with my children, and it was like, it's exactly the same.

It is a great film with Matthew Broderick, I highly recommend everybody watches it. Talking about hallucinations.  

The difference now is just that there's more compute power available to actually power these things. I think there's gonna be a real impact around it, and I think there are real opportunities, but I think we're also going through an enormous hype cycle. And again, I've seen these many times throughout my career. You know, I'd expect, you know, there's lots of money that's gonna be wasted

Every CEO is speaking to each other about what you doing around AI. And if your CTO is then not. Telling you what you're doing about AI.

There's just this massive FOMO, which is very similar to the time when mobile apps came along. But where the genuine application is going to come out of it? Is, you know, still remains to be seen. There definitely will be something, but I don't think it's anything like you hear people talk about on Twitter.

Richard: Yeah, it's, it's quite incredible the amount of noise you're hearing out there at the moment. ., what skills would you say a technology leader should look to develop if they're trying to get on in their career?

Rob: First one for me is always delegation. The most common trap I see people fall, fall into, particularly if they go from say, a developer to a lead developer. They think that their job is just to get everything out of everybody's else's way. They are not comfortable with telling people what to do, and Just get lost in the weeds and they're not looking for long-term strategy.

Positive power and influence, I think is an interesting one. I went on a great course a few years ago about this, which is, that was actually the name of the course, but it was, it's about being able to, Have the different tools in your toolbox around the different influencing styles.

You may be the kind of person that's really good at bridging and bringing people together Influencing kind of more what might be considered more warm skills. But you also really need to be quite good at being assertive as well. An assertive communication to me is really important, so people have clarity.

About expectations and people have clarity about accountability and I used to be uncomfortable with this. I always felt for myself, oh, just a servant in leadership and I'm a nice person.

But the problem with that is just people aren't clear on expectations, and actually they can get annoyed when that's the case.

Then my last one is empathy. I think it's something that I've always relied on heavily in my career. Some of my worst moments were where in the, you were in these real them and us situations with different departments in your organization.  And it really is about in any situation, being able to consider things from someone else's point of view.  Then getting into these kinds of binary positions of conflict.

That's probably my top three.

Richard: Brilliant. I think they're brilliant, Rob. I have to say, and, and broadly speaking, I would totally agree with those. A hundred percent.

Okay. there's lots of information out there and we're always trying to keep up to date with, with stuff. Who, do you follow or which sites do you look to for sources of trusted information?

Rob: Oh, it's a difficult one these days, isn't it?

There's so, so many and I've really had to think quite hard of this, and I, and there's, there's not really one area. I mean, I'm always kind of trying to follow people on LinkedIn and, and Twitter as well, but Twitter seems to have died. I don't know if half of the developers have gone off to BlueSky or, or somewhere else, like Mastodon, but sadly that's not quite the same.

I think the approach I generally tend to take is I try to just follow a wide variety of sources, including many of which I don't agree with. And what's important for me is I'm always trying to challenge my thinking and preconceptions with those kind of things as well.

All of that. I think if there's one person that I've really enjoyed following over the last few years, it's Charity Majors, She Goes by MissTipsy on Twitter and is one of the founders of Honeycomb.io. It's an observability platform and I think she's really good in being saying kind of good, provocative sort of things in a constructive way recently around, you know, what matters around, you know, a lot around that kind of build, measure, learn cycle. I had the pleasure of meeting her in person a few months ago and getting a selfie with her, Which was great.

Richard: Excellent. Do you have a book or series of books that you'd recommend to someone who's trying to get on in their technology career? Some seminal books that you, you, you feel that you can lean back on?

Rob Yeah, more interestingly than your previous question, I've got loads. I really love books and probably, I, wrote a blog post I think, sort of 15 years ago, which was, it said something like, read books and earn more money. I found reading to be the thing that's kind of really unlocked the most opportunity in my career.

Most of my favourites these days and probably where I focus on with such a big list is more around leadership and I think these are some of the ones that I just seem to recommend the most. So we've got Seven Habits of Highly Effective People

I really enjoy that one. It's, it's just, it sounds like a corny title, but actually when you read it, it's, it really is quite fundamental and quite profound.

Richard is showing his copy. The goal by Eli Goldratt, dunno if you've come across that one, but it's around this concept called Theory of Constraints. It's also quite fun because it's written as a novel. It's bit corny cuz it's a bit American. But massive on systems thinking and theory of constraints is a key component of that.

I think it's one of the books that that's often said that Jeff Bezos least used to say is, is the three books he gives to any leader in his organization. Couple of books by a guy called Patrick Lencioni. Five Dysfunctions of a Team, which I just think is fantastic. It's a quick, easy read, it's practical.

There's another one he's written though, which is probably my even more enjoyable, which is one called The Advantage, which is all about organizational health. I think there's all these exciting, you know, sort of challenging, innovative methodologies out there. But I think a lot of what gets missed in organizations is just fundamental organizational hygiene.

Again, it's a really quick book to read. It just focus on, you know, have a very clear strategy as your organization. Make sure you communicate it really well over communicate it. And then his last bit is having a functioning leadership team, which comes back to the five dysfunctions of a team.

 Probably the last one is one called Getting to Yes, which is about negotiating and negotiating agreement without getting in or giving in. I really like it. It's probably only about sort of 80 pages long got loads of really good approaches and techniques for how you can. But you will be.

You will be as a leader negotiating loads.

Richard: Fantastic, some brilliant recommendations there. I will definitely add them to the show notes. I, I've, I've read the Five Dysfunctions of a, a Leadership team, but I haven't read the other one, so I'm, I'm really intrigued now cause I did find that really, really impressive. So. Excellent.

Thank you so much for those Rob. The way we like to wrap up here is , to ask you, look, you know, if you went back and, and you had to, you could tell your 20 year old self one bit of information that would enable you to get on your career, what would it be and why?

Rob: Yeah, another tough question. The fact that you're speaking to me is, you know, I've been quite successful, right? So, All things being considered. Must have done some things right. Look, I just didn't expect to end up where I am and I just feel hugely privileged that, that I am what's worked for me isn't necessarily what's worked for other people.

But, but I think probably the one thing I would say is, Don't be afraid to ask the stupid questions. I think the sort of biggest inflection points in my career were, were where I was just, I think it was probably when I was working at the BBC actually, and I joined a, a team. Just come back from traveling actually.

 I realized quite quickly that everybody in the team was way better than me and sort of looking around and just really crapping myself. And there was two choices there. Either you just try and fake it or you face into it, and I did. So thankfully there was some really. Nice people in the team that were really patient with me.

There were some fundamental concepts around some, some things we were doing. I just didn't understand and I asked the stupid question and I was like, I'm So, I asked them again if I didn't understand it. And I think within the kind of six months that that I took approach probably just changed everything for me and accelerated my learning and is probably the thing that kickstarted the rest of my career.

Richard: I think that's a brilliant way to end and, and a great piece of advice there. Yeah, absolutely. There is no problem with asking. Well, they say there's no such thing as a stupid question and there isn't, but you certainly shouldn't fear asking anything. percent agree. Look, Rob, thank you so much for your time today.

Some, some great learning and in insights there. I just would like to say thanks so much for taking the time to speak with us today.

Rob: that's great. Thanks, Richard. It's been a real pleasure and I enjoyed speaking to you. Thank you.


*Please note that this transcript is produced by AI and will likely contain some errors

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