Inside this episode

Today we are in conversation with Andy Skipper, Founder and Chief Coach of CTO Craft and we talk about what is a CTO Coach and what does it take to be a good CTO.

Host: Aaron Rackley

Guest: Andy Skipper

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Show Transcript

These transcripts where auto generated by Descript. If you see any issues, please do reach out and we can rectify the issues.

Aaron Rackley: [00:00:00] Hi, everyone, and welcome to this episode of the Tech Leadership Decoded podcast. The podcast where through conversations, we unraveled intricacies of leadership in the tech industry and provide insights on how to become a top performing leader. Today, we’re in conversation with Andy Skipper, founder and chief coach of CTO Craft.

And we talk about What is CTO craft and what does it take to be a great CTO? But before we start, can I just ask a quick favor? If you like this conversation and this podcast in general, please do remember to subscribe on your favorite player. And then if you have two minutes, can you just share the link of this episode to your social media sites so we can reach more amazing technical leaders like you?

And that’s it. Thank you. And with that, let’s get into today’s episode with Andy. Okay, and welcome Andy and thank you for joining me today on the podcast. You’re having a great day Um, so yeah, we are here today to talk about What a C T O coach is [00:01:00] and what C t O craft is. Um, but before we get into all of that super fun stuff, do you just wanna spend five minutes just explaining who you are, your experience and how you came to be part of C T O Craft and a C T O coach?

Andy Skipper: Yeah, of course. So I’m a, I’m a technologist by background, so I was mm-hmm. . A developer for many, many years, mostly in the startup world, various digital agencies, um, and then became a, a CTO kind of by accident in one of the startups I was working with, um, in that they didn’t have any kind of leadership within the technology side of the business.

Uh, so I, I kind of filled a bit of a void there. Um, and since then I’ve been CTO, uh, gosh, um, too many companies to, to remember. Um, at some point I, uh, I decided to, uh, to go the fractional route. So it was a fractional CTO, [00:02:00] um, for a while and, um, and actually had a consultancy, a group of. Fractional CTOs that I was helping find work.

Um, and I found that more and more of the, the fractional work that I was doing personally was actually either coming in to replace a, a CTO who had burnt out or hadn’t been able to scale with the business or just hasn’t worked out or coming in alongside someone like that and kind of supporting them in.

Growing into it and, um, and finding their way a little bit. And so I, I decided that was the part of the role that I was enjoying the most. So I’d kind of doubled down and, um, and that was all I did for, um, for a few years, um, as CTO craft kind of came about as a platform for the people that I was coaching one to one.

Um, and this was back in 2017, um, and it’s grown from there basically. So it started off with. Know a hundred people or so [00:03:00] in London. Um, and it’s now just over 12,000 people all around the world. Mm-hmm. . Um, and, uh, yeah, it’s great fun.

Aaron Rackley: Oh, awesome. Cool. So I think we should start at the beginning of like, what do you consider to be a C T O in, in your, in your definition of it?

Andy Skipper: Yeah. It’s, it’s a really interesting question because I think that, um, If you were to ask that question of an investor, they would probably have a pretty static answer to it. There’d be one specific profile that they think of, but in truth, it’s very different depending on the stage of the company, the kind of industry they’re in, um, the kind of person, you know, so there are some CTO archetypes.

Like you get CTOs who are very, very technical and they stay hands on. Um, well, there are CTOs who are more strategic, more visionary. There are CTOs who [00:04:00] are more operational and you get CTOs who are more people focused. And the truth is that companies kind of need different profiles of CTO at different times in their lifetime.

But the, the one thing that kind of glues them all together is that they’re all theoretically, they’re all the apex technologists within their company. They’re all top of the food chain. As far as the technology is concerned, so they, that they’re where the buck stops essentially for technology stuff.

Aaron Rackley: Okay. And you mentioned there in your little introduction about being a fractional CTO. Now, can you, what does that mean?

Andy Skipper: So fractional CTOs or fractional C anything Os, they’re basically, um, they, they work on a portfolio of clients and typically they’ll work more on an advisory and a guidance basis rather than operational.

But [00:05:00] where, um, where companies see the most benefit from having someone like a fractional CTO is where they want someone with a lot of experience, um, but don’t have the budget to pay for somebody full time at that kind of level. Um, or they have someone slightly more junior or a first time leader within the company who needs some kind of support to avoid the pitfalls and, um, and make the best choices.

Um, so yeah, as a, as a fractional CTO, you could be working for a company. Two days a month or you can be with them four days a week, you know, it’s very variable But the the point is that you’re working with many at the same time. So it’s having a Portfolio cto career.

Aaron Rackley: Okay. Um, what do you think? um, the biggest challenges are for Uh people becoming a cto like taking their first role into that c [00:06:00] cto suite Uh, seat, sorry, not suite, seat.

Andy Skipper: So, um, I would say typically it’s because when you first hit that kind of role, especially if it’s in a, a smallish startup, usually come up through being a very, very good developer. You know, you might come up through being a good developer, then an engineering manager, then et cetera, et cetera, until you get CTO, but typically.

You’re not too far removed from actually developing code. And the problem is that the skill set you need to be a very good developer is very different from what you need to be a very good leader of developers. And I think most people and most companies don’t recognize that when they’re putting people like that into a C level position.

And so there’s, there’s not a lot of support. You kind of have a whole new load of skills to, um, to build. You know, you’re, you’re on the critical path for the success [00:07:00] of the company at a C level. And so, um, that, that’s where problems start to happen. You see a lot of burnout in first time CTOs. Um, and yeah, obviously they have reasonable budgets.

They have reasonable ownership of, um, of, you know, large parts of the, the company’s outgoings in terms of development teams that they might not have experience with. Et cetera, et cetera, but it’s getting past that hurdle and recognizing that it is a new set of skills and it’s not an evolution of being a very good developer.

Aaron Rackley: And I guess that leads us to kind of like what CTO craft is and what you do as a role, right? So like that’s where a CTO coach would come in to help. I

Andy Skipper: imagine. Yeah, absolutely. And so, um, both coaching and, uh, peer validation or community validation, I’d say that’s, that’s the biggest. Benefit that I had when I was coming out through being a developer and a [00:08:00] CTO, or rather I should say it’s what I didn’t have because there wasn’t a community like this at the time, but it’s, it’s being around other people who are going through the same kind of struggles as the same kind of learning journey.

Um, and then also having access to much more experienced CTOs. Um, who, uh, who can kind of guide you down certain paths or help you set goals, et cetera, et cetera. Yeah, that’s it.

Aaron Rackley: So I, so for me, for example, I’m a technical leader at the moment for the company that I work for. So if we use me as an example and I career trajectory, I want to become a CTO.

Like what, what kind of things should I be focusing on? Cause obviously up until this point, the focus has been mainly, like you say. Being a very good individual contributor to the code based, you know, designing systems and stuff. So what, what’s the What’s the pathway now, like what kind of things should I be focusing on in that, in that field?

Andy Skipper: So the two biggest things I would [00:09:00] say you should be focusing on to kind of get to that C suite level, executive suite level, are commercial understanding, getting much more involved in the strategy and the objectives of the business, understanding what the different parts of the business are doing, how they will feed into the success of the business.

Because as a CTO, You kind of need to understand what shape cog you are to fit into that machine to help it keep turning and keep succeeding. Um, and that, again, that’s, that’s one of these skills or understandings that you don’t get when you’re taking a backlog and developing and putting, putting features out, essentially, you don’t get as much exposure to that.

Um, and the other thing is communication skills and people’s skills. So absolutely at that C level, even if you are still hands on, there’s going to be quite a lot of, um, people management stuff. There’s going to be negotiation. There’s going to be [00:10:00] HR related stuff. There’s going to be. stakeholder management, there’s going to be presentation of technical stuff or communication of technical stuff into a form that non technical people can understand.

Um, but it’s those two being more commercial and being more, more aware and proficient with your communication skills.

Aaron Rackley: So as. As a CTO coach, what kind of things, uh, do you see in people that make them successful in a CTO role over the ones that potentially go down that route and kind of, I don’t want to say fail, but move out, move away from it because they didn’t like it or whatever reason.


Andy Skipper: Yeah. There are a few things. I mean, one of the things definitely is, um, energy management. You know, one, one thing that is very prevalent in the tech industry, especially among the male side of the tech industry. Which is still by far the biggest side, [00:11:00] obviously, um, is this propensity to take on more work and, um, and not pay attention enough to the resources you have on a personal basis to get all that stuff done.

So then, as I said before, there’s a lot of burnout, um, not just in CTAs, but also the levels directly underneath them where you feel that you should be capable of. Figuring out every problem or making every decision correctly. The first time should be capable of being everything to everyone. Essentially

Aaron Rackley: is the different level of how removed a CTO has become from like the technology ecosystem.

I find it, it’s been so varied. So I, I think it’d be interesting to ask, like, do you think as a CTO being really on the pulse of everything is still important or. Is it the other side that’s more important? Like you said, the commercials, [00:12:00] like where, what do you think? Is there a balance?

Andy Skipper: Yeah, there’s a balance, but as I said before, it’s very different depending on what kind of company or what size company or what stage company you’re in.

You know, I think it’s fine to be very, um, hands on or at least being completely aware of all the different parts of the infrastructure or the architecture. Knowing who to talk to, to find out about the stuff that you don’t know is, is very important in those situations, but yeah, at, at later stages or as the team grows, um, you, you just can’t be on top of all the, the implementation stuff.

It’s just impossible. Um, you know, I, I don’t think there’s a specific kind of concrete inflection point that you hit, I think it’s different for every company. Um, but certainly a CTO should expect eventually to be quite abstracted away from the day to day coding stuff. At [00:13:00] some point,

Aaron Rackley: okay, just a minute ago, we were talking about what makes, um, a CTO successful, but what on the flip side of that, what do you think a biggest mistake someone as their first CEO makes?

Andy Skipper: So CTO, sorry. Yeah. Yeah. So, so, um, a big mistake that I’ve seen many times. is staying too embedded within the engineering team or the people underneath the CTO. You know, it’s there, the whole concept of the first team that from the, um, the Patrick Mencione book. Um, that talks about your first level of responsibility is actually being to the leaders in different functions who are alongside you rather than to the people underneath you.

And, you know, especially if you’ve been promoted up from being a developer, being part of that team, that can be quite difficult and you can stay very protective of those [00:14:00] people. You can be biased towards decisions that favor those people. Et cetera, et cetera, et cetera. Um, so that that’s a mistake I see quite commonly that they don’t pay enough attention to what the other parts of the business actually need from technology and focus on the needs of the technologists.

Aaron Rackley: Okay. Yeah. Interesting. So let’s talk about CTO craft. So can you give us an overview of what that is and how it breaks down and why even just someone as me, who’s. Technical, technical leadership wise, it’s important, but definitely for a CDO.

Andy Skipper: Yeah, sure. But it’s, it’s an ever expanding suite of stuff for technology leaders.

Um, the, the core of it is a Slack group, um, which is buzzing, you know, people use it for peer validation. They use it for getting feedback on approaches. They use it [00:15:00] for getting recommendations for penetration, testing companies, you know, all sorts of stuff. Um, and then alongside that we have a newsletter tech manager weekly.

We have weekly events and then we have a conference every year or two, two conferences this year for better or for worse. Um, then the, so the coaching, we do two, two types of coaching. So we’ve got a pool of one to one coaches who are all, have all been CTOs at some point, um, and it’s kind of a, uh, a halfway house between proper coaching and the executive coaching sense.

Where it’s non directional and it’s more about helping people define their path and then helping them hit their own goals and mentorship where the people actually have some context awareness of leading technology teams and building products and that sort of stuff. So it’s, we, we basically do a matchmaking service between [00:16:00] people who are looking for a one to one coach and.

And the CTOs who are coaching, um, and that’s, that’s one part. And then we do, um, something called circles, which are peer groups of 10 to 12 people who meet once a month for a guided discussion on topics that they suggest. Um, and again, that’s, that’s more about. Peer to peer validation, having a, you know, a fixed tribe of people that you form quite close relationships with and, um, and it’s all very confidential.

So they, they rant about their situations and they offer each other solutions and so on and so forth. And then apart from, apart from all that, we also have now launched Campus, which is our learning platform. So this is more education focused. Um, and that’s a, it’s a, a learning community. So it’s got lots of social aspects, but, [00:17:00] um, it’s also got a large directory of.

Videos and content, and we’re slowly, but surely adding courses. Um, so self paced things, Udemy style, uh, again with a social element. So you can discuss the topics with other people who are going through the course and that kind of thing. Um, and that’s, that’s been out for. Eight days and then it seems to be going well so far, but it’s very, very new.

Yeah, that’s it.

Aaron Rackley: Awesome. And you mentioned that you’ve got a couple of events coming this year. Uh, that there’s not much time left in this year. Um, so. What kind of, um, event is that? Is that a conference?

Andy Skipper: Yeah, so we’ve got a conference coming up on November the 7th, um, and 8th, which is focused on culture, engineering culture.

It’s [00:18:00] got lots of people talking about, um, Making sure the culture within their teams supports the development of the, the company, but also the development of the people. Um, we’ve got, uh, Michael Lopp doing a keynote. He runs the RANDS leadership Slack, um, and a bunch of other people, people from Facebook, et cetera, et cetera.

But yeah, I’d say. Two day conference in London, tickets available now.

Aaron Rackley: Well, I saw this morning. I don’t think there’s much left. Is there? Not many, not many. 10%, I think I saw this morning. So yeah, that’s, that’s good to hear. Um, cool. So I will make sure that in obviously the, the notes that we put a link to CTO craft and.

The campus and everything like that, because I’ve, I’ve had a quick look at the campus and it looks from what I’ve seen on it so far looks awesome. Um, I’m going to try and convince my job that part of my budget this year should be allowed to go towards it. We’ll see what they [00:19:00] say. Um, so as someone who deals with a lot of CTOs, um, in your coaching aspect, what do you, what’s your thoughts on the future of CTO leadership and Because I think the reason I’m asking that is because, like you say, with like startups, larger style companies and everything, I’ve, I’ve seen in some of the startups that I’ve looked at and talked to, it’s kind of blurred almost, like not there as a thing.

So I don’t know if that’s just because of the size difference and whatnot, but where do you think this CTO leadership in general is? Going in the future.

Andy Skipper: So, I’d say one pattern that I’ve definitely seen, uh, over the last 12 months is that… Um, companies are dealing with much less resource, you know, and they have much tighter purse strings than they did 12, 24 months ago, even [00:20:00] over the pandemic, which means, you know, there are redundancies.

There are, you know, uh, paused hiring processes, et cetera, et cetera. So people are having to do a bit more with a bit less. Um, but that doesn’t stop the amount of innovation doesn’t stop the amount of. Um, opportunity there is, so I think it’s, I think that’s the biggest thing that I’ve seen people preparing themselves to do more with less.

Um, I think in terms of actual innovation, in terms of technologies, we’ll be looking at, obviously there’s the whole gen AI wave that’s washing over everyone. I see a lot of, um, a lot of people. Jumping into that and finding ways of improving their business or improving their productivity, um, using Gen AI.

Uh, I don’t see a point where a CTO will never have a team of developers to, to, to lead. I think that’s, that’s [00:21:00] probably a long way off if ever coming, but, you know, fun, fundamentally, I don’t see that change to the implementation of Gen AI as being very different from. The implementation of developing for mobile devices or, you know, developing for the blockchain, et cetera, et cetera.

These are waves that come over us and leave us changed, but don’t completely append things.

Aaron Rackley: Yeah. They’re just coming a lot quicker and faster. Used to be decades now, then a few years now months. Yeah. Um, I’m interested in. You as a coach. So like what with CTOs, um, and what kind of, what are you looking for from someone that you want to coach?

Um, cause I’m, I’m, I imagine coaches don’t just go, I’ll pick it. I’ll pick everyone. I imagine you can be quite, quite selective. So what are you looking

Andy Skipper: for when [00:22:00] you’re… So I, I specialize. Okay. Not, not all of the coaches in the AT C T O craft do, but I, I specialize, I tend to focus on people who are struggling with stress and energy levels.

Mm-hmm. , um, you know, so I’ve, I’ve been through a burnout as a C T O a couple of times. Um, and come out the other end. So it is, it is a topic that I tend to gravitate towards, um, in terms of the people that I, I look to coach, I think it’s people who are open to making changes fundamentally, I think that would be true of most coaches.

Um, we do get inbound leads for coaching from founders or even investors in some cases where they’re kind of imposing it on their, on their CTOs. Yeah. Rather than it being an active process for the CTO to go out and try and find support for themselves. Um, and you know, we’ll, we, we do work in that way [00:23:00] successfully, but it is harder because that CTO doesn’t have a, a natural desire to go out looking for change.

Um, but yeah, uh, there, there are some in the, the, the coaching pool. Um, who will take people who are not even in, in some kind of challenging situation, you know, and they, they use them more like a conciliary feedback loop kind of person rather than actively coaching and changing their behaviors and all that sort of stuff.


Aaron Rackley: no, very interesting. So I don’t want you to give away all your secrets but um, you mentioned there that you specialize in, you know, burnout and stress and stuff. So is there one little bit of nugget we could give to everyone that’s like a tech a technique or something for how to deal with burnout?

Because I see it all the time. It’s… Everywhere I work there’s burnout every year, especially at this [00:24:00] time of year where you’re getting close to the end of Christmas and financial years and stuff

Andy Skipper: like that. Yeah. I mean, the biggest thing for me was learning that it is so widespread. You know, cause I think a lot of people, when they start to experience that kind of disengagement from work and dealing with kind of health problems or, you know, fatigue that comes with being burnt out, they, they kind of assume it’s specific to them and it’s because they’re not good enough where it’s, that’s not at all the case.

It is very, very widespread and it’s. Very, very common, especially among first time CTOs, as I said before, um, so understanding that, um, and then being a bit more brutal about setting time aside for recovery, you know, um, and talking to people, talking, talking to your manager, talking to. People who are in [00:25:00] your, your first team, Lencioni’s first team, or speaking to people in your family and just being open about it, being transparent about the fact that it is affecting you both at work and at home, because it likely is.

Um, getting support, going and talk to professionals if you need to, um, but not brushing it under the corner of a rug and, and assuming it’s just something that’s wrong with you, essentially, that never ends up well, if you do that. Yeah,

Aaron Rackley: no, a hundred percent agree with you there. So in, in that, in that kind of world of, like we say, time, what balance.

And just stepping aside, obviously with lockdown over and everyone now having years of this hybrid working full, full working, do you have like a kind of, [00:26:00] sorry, I’m just calling you out. Do you, do you have like a stance on that kind of aspect? Cause I’m, I’m reading a lot of articles at the moment where there’s a lot of companies reverting back to pulling everyone back into the office.

So do you think that’s a. I mean, a wise move or do you think that would change again in a few

Andy Skipper: years or I don’t think there’s a one size fits all, um, solution to that. I think what the pandemic did show us is that it is possible to, to operate a team successfully remotely. Um, I think a lot of the problems that I’ve seen or heard of from people who complained about it is, um.

Trying to make the hybrid style work where you have some people who are in the office all the time, and then some people come in a couple of days a week or whatever, I think that is very difficult to get right. Um, because people, employees have kind of come to expect a level of flexibility and a level of comfort [00:27:00] and not having to commute and all that sort of stuff.

And giving some of that up to come in part of the time means that sacrificing something without gaining something. I think this is, this is my armchair psychologist coming in. I think that’s the case, but I’ve, you know, I’ve seen companies do the hybrid thing very well. I’ve seen the whole RTO returns to the office thing happened seamlessly.

You know, a lot of it depends on the people, depends on the company, depends on the culture. Um, yeah.

Aaron Rackley: Yeah. So what do you, what do you think, um, CTOs can do, or is it even in their remit, right? To help structure that culture to, for whatever it means ends up being, whether it’s remote, hybrid, whatever, but what part do you think, how much of a part do you think a CTO should have in?

Andy Skipper: And that certainly they should be capable of fighting, uh, fighting for that [00:28:00] cause. If a team does want to stay completely remote, then they should be capable of articulating to the other people in the company. Why that’s not a problem or vice versa, if it is a problem and they can justifiably see it as a problem, having the, uh, having the, the guts to tell the team that and say that it’s just not possible.

Um, yeah, other than that, I think there are certain skills around asynchronous working and meeting management and, um. You know, working, working with people who are predominantly remote is not quite as tricky as working with people who are half remote, half not, or sometimes remote. Mm-hmm. , you know, so there, there are some specific skills to learn there.

Aaron Rackley: And I, and, and I, if, if anyone wants to learn all these skills, they can go to your campus.

Andy Skipper: They can, they can go to the campus. . [00:29:00] I’d also definitely recommend the, um, the, the GitLab. Book on remote working and that’s a great resource for, for how they do it. And obviously they, they are a hundred percent remote, I believe.

I think they’ve

Aaron Rackley: always been remote.

Andy Skipper: Haven’t they? I think so. I think so.

Aaron Rackley: Yeah. So probably nailed it right down.

Andy Skipper: You would hope so. You would

Aaron Rackley: hope so. Yeah. Um, cool. Now, obviously I could delve into all of the pillars that you guys mentioned on the website for what you learn. So I’ll just say the four that I think you’ve got on there, which is like leadership, strategy, culture, technology, operations, and then like, like you said, stress and wellbeing.

And what I’m going to do is I’m going to go away, make that list and find people to come on and talk about each of those different aspects. Um, but I’ll point everyone towards it. Um, So before, one thing I’d like to ask everyone that comes on to the podcast is I’ve got on the website, I’ve [00:30:00] got a bookshelf and I ask everyone to just recommend one book and caveat, it doesn’t have to be related to the subject of tech or anything at all.

It can be your favorite childhood book, but the idea is to just put something new on there for people to read and hopefully learn something new. Um, do you have a rap, uh, a book recommendation? Outside of the GitLab one, because I’ll put that one on anyway.

Andy Skipper: Honestly, the hard part here is only recommending one.

Aaron Rackley: You can, you can recommend a couple. I think someone listed off like five the other week and I was like, okay, finding them all.

Andy Skipper: So I definitely recommend Patrick Linceoni, who I mentioned before, two books of his. Um, the five dysfunctions of a team and the advantage, um, they’re both about interpersonal relationships within leadership teams and culture and the, um, you know, the business benefits of having a good, a good culture within your team, et cetera, [00:31:00] et cetera.

Um, punished by rewards is very good by Alfie Cohn. Um, and that talks about motivation and how to actually get stuff out of people without. It being, uh, a carrot being dangled or a stick being brandished, you know?

Aaron Rackley: Hmm, I’ll definitely have to pick that one up. I’ve read the Five Dysfunctions of a Successful Teammate.

That’s a very good, that’s the one that’s written in a novel style, isn’t it? That’s right, yeah. Yeah, it’s very good. I really enjoyed that one. Um, so I’ll definitely… Pick up the other one. Well, I’d say, I say it to everyone every week, but since starting this, I now have, my bookshelf’s getting too big because I have to buy every book just to, and then, yeah.

Um. So before you go, I think if you can just share everyone where they can find everything online, where they can find you, CTO Craft, and we’ll make sure those links also go into the, um, to

Andy Skipper: the show notes. Yeah. Um, so almost everything [00:32:00] is on ctocraft. com. That’s the first place to go. You can sign up for the community there.

You can find out more about the conference and buy tickets. Uh, you can find out about campus, et cetera, et cetera. They’re all linked to from there. Um, so that that’s the place to go and you can find us on LinkedIn as well and on YouTube, a bunch of stuff on YouTube. Um, yeah, those are the main ones not Twitter.

I’m not doing Twitter anymore.

Aaron Rackley: Oh, no controversial

Cool well, no, I I appreciate you coming and taking the time. Um, obviously We met through the Slack channel, um, on CTO craft. So I am there for anyone that decides to join on there is also, you can say hi. Um, so appreciate you coming on to talk about it and. Yeah, hopefully I will be able to come to one of these events very soon.

I just need to find the time. Indeed. Indeed. Yeah. Well, thank you very much, [00:33:00] Andy. I appreciate it. No

Andy Skipper: worries. Good to talk to you. Thanks for having me on. Thank you, mate.

Aaron Rackley: Hey, thank you for making it all the way to the end of today’s episode. It means the world to me that you have made it this far. I really love making these episodes. I would like to make even more. So please, if you have two minutes to spare, can you just quickly share this podcast on your social media sites?

Or even point it to a guest you think would be great for the show. I’d really appreciate that. Thank you. And until next time, have a great day, and I’ll see you soon. Bye.