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​Kulvinder: Welcome to Tech Exec in the tech industry to discuss their experiences, perspectives, and vision for the future of technology. This episode is all about leveling up your skills through coaching, networking, and learning from others. I'm Kulvinder, your host, and in this episode I'm thrilled to be talking to Andy Skipper. Andy is the chief CTO Coach of CTO Craft a Learning and Coaching Network for technology leaders. He's held CTO roles since 2006, including roles with made.com and Comic Relief, one of the UK's largest charities. With his extensive experience in technology leadership, Andy's been instrumental in helping CTOs and other technology leaders build professional and leadership skills through CTO Craft. Andy, welcome to the show and thanks for joining me today. How are you?

Andy: 0:48

Yeah, I'm fine. Thanks. Yeah, it's a busy time, but, uh, busy in a good way.

Kulvinder: 0:52

Great to hear. Let's dive into the world of CTO Craft. Andy, you've got lots of experience, both as a technology leader, as, as well as helping other technology leaders. So I have to ask, what inspired you to start CTO Craft and what were some of the biggest challenges you faced in getting the organization up and running?

Andy: 1:08

So I suppose the story goes back to my, my first CTO role back in 2006. Um, and I, I made my way into that role really through being a, a developer. And I, I was a reasonably good developer, but I was better at coordinating people.. Um, and in that particular case, I was better at shielding them from all the stuff that was going on around them. So it was quite dysfunctional when I came in. Um, and I, I kind of stood up and I got in the way of people around interference, as they say, but I'll say took a bit more of a, um, uh, a, a deeper look into. How they were, you know, their actual wellbeing and how, how the work was affecting them. It was typical early stage startup, very frantic, lots of pressures, um, et cetera, et cetera. And I became CTO because by helping those people, I was actually making them more productive. So we got more done, we hit more deadlines, et cetera, et cetera. And that, that kind of stayed with me throughout my CTO journey, I guess. So from from there through made.com through Comic Relief, and then I eventually became a freelance CTO, so actually left comic relief to, to go freelance and consulting. Um, and I found that a lot of the work that I was doing in those consulting CTO roles was actually. Supporting leaders who were in that position and they, they didn't have a lot of support. They didn't have a lot of guidance. There was a lot of burnout. There was a lot of, uh, kind of, um, fear that they weren't fulfilling the role they needed to. There was a lot of pressure on them. There was a, a lot of, um,, isolation, et cetera, et cetera. And so I, I discovered that in those consulting roles, the best bang for the buck was actually coaching those people and actually supporting them, helping them build skills, mentoring them. And that became very successful. Um, and I eventually joined forces with a number of other people who were CTOs, but also coaches. Um, either through their actual CTO roles where they, you know, similar to me in my first role, they were getting the, the biggest bang for the buck by actually coaching and looking at the whole person, not just the backlog and what needs to be done. Um, and CTO Craft originally was a, a platform for our coaching. Um, and it's, it's grown beyond that into a, you know, a, a whatever it is, nine and a half thousand people worldwide, community of people, all of whom are, have some kind of experience with, um, with leadership and are all leading teams of developers. There's, there, there are no individual contributors there who are not also CTO, if that makes sense. So they're, they're typically CTOs of five to 300 person teams. And so that, um, that really is now what we do. We support people by putting them with other people.. Um, and they get the benefit of the, the hive mind as they say. But we also do one-to-one coaching still, but we also do mentoring groups or circles as we call them, which are, um, like a community of practice. Um, and those have been very successful. We've got about, I think about 180 people in those, those groups. Um, and then we also do a bunch of other stuff like events. We've got a, a conference coming up in May. Uh, we do in-person meet ups and socials and that sort of stuff. And we have a newsletter that goes out every week, Tech Manager Weekly. Um, and yeah, it's got a life of its own.

Kulvinder: 5:01

Fantastic. And do you find. People leading teams of five to 300 plus that the demands are different i.e., what might qualify as success.

Andy: 5:11

Yeah, absolutely. I mean, CTO is a very far-reaching title from my experience. You know, you can be the CTO of a a two person startup, in which case you are. You are the tech team, , you are the entirety of the tech team.. Um, and the, the needs of a person in that kind of position are very different from the needs of a person leading a, a team of directors who lead a team of managers who lead a team of developers. Um, so yeah, very much so. It's, it's very different.

Kulvinder: 5:43

And you mentioned, um, obviously CTO can mean a range of things, or it's, it's quite a broad church, I guess. Is, is there anything you would say is, is common across all CTOs?

Andy: 5:53

Yeah, and I, I'd say it's also potentially the, the, um, the criteria that most commonly gets missed by people who are coming up into the role and moving into their, you know, maybe their second or third roles. And that's, um, commercial awareness . So you know I, I see the CTO role being a commercial role as much as a technology role. So, you know, there, um, there are a lot of individual contributors who move up into senior leadership who are, are very kind of focused on the, the building of stuff, which is obviously important. Um, but, but leaving aside the understanding of why they're actually building that stuff and the effect it has on the business and aligning with other teams and understanding the business objectives and cash flow and all that sort of stuff. Um, and that, that's the same whether you are leading a thousand people or two people.

Kulvinder: 6:52

That makes sense. I, I think that resonates with my own experience as well, that that commercial expertise might not be there at the start of your journey needs to be developed, essentially. So what are some of the, uh, significant challenges and trends you're seeing today in technology industry and how is CTO Craft responding to them?

Andy: 7:09

Yeah. Well, I mean, the, the biggest things that we're seeing at the moment are redundancies still, and that that's really been the, the biggest, uh, Negative thing that we've seen in the ecosystem since this time last year. Realistically, you know, we had the effects of the, the pandemic and, um, and, um, furloughs and working from home and all that sort of stuff, immediately followed by a bunch of redundancies. You know, the, the, the large technical organizations obviously made a, a whole bunch of redundancies and still are making redundancies. You know, Amazon is making a, a whole load more this week. Um, and that's kind of trickled down. And then you've had other kind of straws that have broke the camel's back, like the, like the, the SVB situation. And, um, even though that was resolved fairly quickly, at least in the UK, it still trickled down to a lot of, a lot of the, um, the engineering teams and, and engineering leaders as well. Um, that, that's the biggest thing. And, you know, really all we can do as CTO Craft for those people is provide them, um, provide them a channel for support, but also, um, potential roles. So we do, we do have partnerships with good CTO specific boutique placement firms. And um, and we have a CTO roles channel in the community, so we can help 'em that way. But, but really it's been moral support, you know, lot of the people in the circles specifically, they get a lot of, um, very personal support from the other people. Cause they're, they have these strong relationships with, um, with the rest of the group. So they know they can, they can get confidential kind of feedback and so on and so forth. But yeah, that, that's it really.

Kulvinder: 9:06

I mean, on that point, given the amount of redundancies around at the moment, are you seeing technology leaders looking to make that move into fractional or interim positions more?

Andy: 9:16

Yeah, very much so. Yeah, there's been a deluge. I think it's, it's been a, a real inflection point for that and that transition to, to fractional stuff. Um, I know one, one of our partners has set up a, a fractional cTO placement division of their, of their hiring company. Right. Um, and at the moment, as I understand it, the supply is outstripping the demand, uh, pretty massively, but no, certainly when, when I took my first fractional roles back in whatever it was, 2014, um, there were, you know, there were a handle, handful of people in London that I'd be competing with, but now I think, You know, in, in the hundreds. Um, and it's, it's understandable as well, you know, the, the, the pressures of the CTO role. Um, are still there, even though you're working potentially on a shorter term basis or for fewer than five days a week. But, uh, um, you do get a lot of flexibility. Um, you know, uh, it's more lucrative obviously, as with any consulting contracting type role. Um, so yeah, I, I can completely understand why more and more people are, are headed that.

Kulvinder: 10:33

I mean, speaking to a few people who have entered the fractional world, what was interesting to me was that they quite enjoyed that startup phase of getting into a new role, understanding and adding value pretty quickly, but perhaps not so much later on down the line, down the line. In terms of BAU, which is still important, but potentially less interesting, uh, would you say that's something that resonates with you as well from the people you've spoken to?

Andy: 10:56

I think it's horses for courses. You know, some, some people like those very early stages and they, they don't like the, uh, the kind of scaling stage. Some people don't like the startup stage, and some people, um, will only do turnarounds for, for larger scale companies that are, are distressed for whatever reason. They, they work with PE firms and so on. But, um, no, it's, it's pretty pretty broad.

Kulvinder: 11:23

Excellent. So look, look, looking at the other end of scale, um, what advice would you give to aspiring technology leaders who are just starting their careers, looking to make a name for themselves in the industry?

Andy: 11:32

Many things, many things, but, but certainly I think when you reach some kind of senior level leadership, you need to start thinking about your mental health and your wellbeing. You know, there, there are a lot of burdens that suddenly land on your back, some of which you are expected to just understand. Um, you know, as if you are, as if you are born with a certain set of leadership skills, which as you know is not really true for anyone. Um, and it's, it's very common to see new CTOs getting into difficulty with stress and, and burnout and, um, and wellbeing in general. So that, that would be the first thing I would suggest that, the other thing I would suggest to a new CTO is to get out the tech team. And understand that the, the tech team is not your, your first team as, as Patrick Lencioni would call it your, your first team who you have the responsibilities to is really the other senior leaders in your company and the other departments. Um, and then, you know, the standard stuff. Learn to delegate more, hire people, develop people into leaders and managers underneath you so that you can, you are not burdened. Forever with all of the, the leadership and all the decision making and all that sort of stuff. Um, but certainly get out of, get out of the, the tech cave. If you have a tech cave. Understand what else is going on in the business. Build some commercial awareness.

Kulvinder: 13:01

And that brings me onto my next question quite nicely, really, and, and you touched on it earlier around commercial awareness and managing up being a skill that folks have to develop. Are there any ways that you could recommend or suggest that people could start to develop those skills? I mean, I take a look at myself and, um, to add value on the financial side of things, at the start of my career, I had to take the time to learn it for myself. So are there any resources or recommendations for folks who may be new to that?

Andy: 13:27

I think as, as you say, the number one place you can learn about that sort of thing is in your, you know, in your own environment, in your own company. Um, but certainly there are a bunch of courses, there's a bunch of books that we always recommend to people about specific areas of, of technology leadership. Um, CTO craft is a great place for validation. So if you already have an approach, you can run it by however many thousand people and get feedback and you know that that's really what the community side of CTO Craft is for. You know, we're not a a training company. We don't train people in the skills, but um, but we do mentor people. We share our experiences and the skills we've learned. We give feedback on approaches. We, um, we support people when those approaches don't work et cetera, et cetera.

Kulvinder: 14:18

I mean, I can attest to the community side of things. It does seem to be a very active community who seem minded to help each other, which is really nice. And, and to be honest, I wish I'd been around at the start of my career. Um, coming on to partners, you, you mentioned collaborating with partners. Are there any that you would particularly highlight that CTO Craft collaborate with?

Andy: 14:39

Uh, partners that CTO Crafts work with? You mean as opposed to the individuals? Yeah, so, um, we, we partner with companies that have some kind of service or product to, to offer, um, who want to get a better understanding of how CTOs work. But we also, um, partner with charities, um, such as Mind. Beam, which is a great London charity for homeless people. Um, and then we also partner with other networks. So we partner with, um, Mind The Product who, um, is basically CTO Craft for product managers and CPOs and heads of product. Um, we, we partner with diversity and underrepresented minority focused, um, groups like, um, Women CTO Dinners and um, SheTO and she can code and, um, black women in tech. you know, uh, all sorts of places like that. And we do that by giving them a platform basically. So we, um, we bring them in, we expose them, um, to the community, we expose, or rather we expose the community to them. Um, yeah, that's, that's the kind of thing we do. We, um, we typically don't have formal partnerships with big kind of hiring companies and that kind of thing. Um, and it, the community itself is, is very much a, a non-salesy place. You know, we don't allow people to come in and, um, and pester and, uh, and approach people about services they're offering and that kind of thing. Um, yeah, that's, that's it.

Kulvinder: 16:22

On that diversity and inclusion point, um, what role do those aspects play in the success of a technology organization in your experience?

Andy: 16:31

So in terms of technology organizations, I, I, I believe, well, no. In my, in my experience, the kind of the, the teams that have at least had one eye on how diverse their teams are, tend to be happier and more productive than the ones that are much more focused on just hiring the best developers. You know, that's, that's, that's the common response you get. We just wanna hire the best. But the pro, the problem is obviously there are a bunch of unconscious biases and um, and they'll blame pipeline problems and all sorts. And, um, but those teams, from my experience, they get very productive. and then they slowly stop being very productive. And, um, that, that doesn't seem to happen with teams that have a better, uh, a better spread of types of people. Um, in terms of the industry as a whole, you know, tech as a whole, I, I think it has to become more diverse for the future because I, I see the needs of technology in the industry moving forward. becoming greater and greater. Um, but at the same time, I see it becoming more and more insular, which I don't think happens when it is more diverse. You know, that's my, my personal opinion, and from what I've seen in those teams that I mentioned, I can see technology as an industry becoming less productive and becoming more insular moving on into the future. And I, I, I don't wanna see that happen. I don't think anybody wants to see that happen. Um, but it, it needs to be more diverse. And also why, why shouldn't it be more diverse? You know, still what, 90% male , probably a high percentage of that white male. Um, why should that be the case? You know? Is there anything biologically that makes us better at leading technologists or being more innovative? No, not really. It's, it's a societal, cultural phenomenon and I don't think it should be allowed to, to just stay that way. Um, yeah, fundamentally.

Kulvinder: 18:49

And do you see that changing over the coming years? Obviously you're shining a light on it via CTO Craft, which is fantastic. Um, and you've provided the platform to highlight diversity and inclusion as something we all need to focus on. Do you think that's evolving?

Andy: 19:03

Um, I dunno about an evolution. I mean, , I suppose in Darwinian terms, an evolution could take hundreds of thousands of years, right? But, but certainly it's not a revolution. Um, it, it is starting to change slowly, you know, but there's, there's still a lot of, um, old-fashioned views on how to hire the best people and what, what the ideal developer looks like and what the ideal technology leader looks like as well. So there's, there's a, there's a lot of work left to do.

Kulvinder: 19:36

What's quite interesting is I, I posted a LinkedIn poll a little while ago asking if photos on cvs and resumes were a good idea. I think if something like 56 or 57% said they thought it was a bad idea because of that unconscious and unconscious bias in some cases. So it's clear we've all got some way to go to break down those barriers, but, uh, hopefully the coming years we'll see will mean that we'll see some changes there.

Andy: 19:58

Yeah, I, I think it has to change. I think it has to change.

Kulvinder: 20:01

Um, look, let's talk broader environment for technology leaders. What do you think might change in the next five years or so.

Andy: 20:08

Hmm. That's a very good question. Uh, I, I see there being a big funding crunch coming our way. You know, though, we're already seeing the, the first examples of that where teams have had to downsize or at least freeze, um, and that that means we're gonna have to adapt to better ways of prioritizing work, better ways of dealing with other departments who want more out of tech, um, et cetera, et cetera. And, and, and obviously it means potentially there'll be a lot more, um, a lot more talent on the market, but maybe not enough budget to, to hire them . So that may mean we'll see salaries dropping a little bit. Um, this is all fairly crystal ball stuff, though. I'm not seeing, I'm not seeing the beginnings of that at all. Um, Yeah. Apart from that, I see, you know, the, the, the hybrid working, working from home versus returning to the office. Uh, I can see that coming to our head in the next few years. Um, either positively or or negatively or apathetically. We'll see. But I, I see there being a firm approach that is more universal in the next few years. Um, Yeah, I, I can see a lot of that leading to more stress, um, rather than less, you know, you, you'd expect that the stress levels would be reduced by people working from home. Um, and I'm not sure I, I see that. I'm not sure I see that at all. So we'll see. Hope, hopefully I'm wrong about that, but, uh, yeah, that's what I worry.

Kulvinder: 21:42

And just coming back to CTO Craft for a minute, I mean, what, what's going on there that's most exciting? You at the moment? What can we expect?

Andy: 21:50

Well, yeah, so our, our first in-person conference, which is on May the 23rd and 24th, and that'll be in, in London at the Tobacco Dock, in, uh, in Wapping. Um, that, that is pretty much taking all our time at the moment. Um, so we're coordinating that The lineup is now full. I think we've sold something like 60 or 70% of the tickets. Um, but we'll be, we'll be up up against it right up to the day.. Um, and then there's, there's another top secret project, which is going on, uh, behind the scenes, which I can't say too much about, but it's. It is gonna change the way CTO Craft works, put it that way. Um, and we'll, uh, yeah, will be a great thing to, to bring it to the community when it's ready.

Kulvinder: 22:38

Fantastic. Wow, that, that all sounds really exciting and I appreciate you carving out the time. Um, I'm sure setting up a conference is not a trivial affair by any stretch, so, uh, so thank you for that. Um, Andy. Thanks so much for your time. It's been enlightening hearing about CTO Craft and everything you do. Um, I hope the conference in May goes well. You've got quite the panel of speakers, so it should be really rewarding for all the attendees.

Andy: 23:02

Thank you. Yeah, it's looking good. Looking good.

Kulvinder: 23:05

Great. Look. Well, that's all there is for this episode of Tech Exec Talks. I hope you joined our conversation with Andy. You can find out more about him and CTO Craft in the show description. If you liked this episode, be sure to follow the show and leave us a review. Your support helps us reach more listeners and viewers. We'll be back soon with another episode, and until then, stay curious.