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CTO Craft: Building a community for CTOs and digital leaders

In our latest Digital Lighthouse episode, Zoe Cunningham is joined by Andy Skipper, founder of CTO Craft. This organisation helps CTOs and Technology Managers in businesses across the world become better leaders through community membership, transformational coaching, mentoring, workshops and events. In our conversation, Andy discusses how a CTO can you create a community of peers that help them to thrive in their role and avoid burnout.

Digital Lighthouse is a mini-series of Techtalks brings you industry insights, opinions, features and interviews impacting the tech industry. Follow us to never miss an episode on SoundCloud now: See all the Digital Lighthouse interviews online for free on SoundCloud

If you’re interested in seeing more from CTO Craft, check out their upcoming events: CTO Craft Con Winter 2022 virtual conference and CTO Craft Bytes – Networks for Tech Leaders: Creating, Using and Nurturing, a London-based in-person event, this November.

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Transcript

Zoe: 

Hello and welcome to Digital Lighthouse. I’m Zoe Cunningham. On the Digital Lighthouse, we get inspiration from tech leaders to help us to shine a light through turbulent times so that we can learn, act and change as a result, for the benefit of our businesses. We believe that if you have a lighthouse, you can harness the power of the storm today.

Today I’m delighted to welcome Andy Skipper from CTO Craft. Hello Andy. Can I ask you please to introduce yourself? Tell us a bit about CTO Craft and also an interesting fact about yourself.

Andy: 

I’m Andy. I’m the founder and chief coach at CTO Craft, which is a mentoring community for CTOs and tech leaders. Interesting fact about myself: I have a dog called Molly Moo Floofy Pants, not named by me, who was a rough Collie, like a ‘Lassie’ dog. She unfortunately has a chest infection at the moment, so you might hear some hacking in the background, which is not me!

Zoe: 

What a fantastic name. That’s a great fact. Molly May Floofy Pants was it?

Andy: 

Molly Moo Floofy Pants

Zoe: 

Haha. Is there a story?

Andy: 

No, it’s just that my wife and my son are incredibly goofy!

Zoe: 

That is the best reason. I love it.

So today, we’re going to be talking about community. And in particular community for CTOs and digital leaders: the best kind of people to have in your community.

So, software building is a team sport, and we all know that teams that gel together make great software together (or something like that!)

If you’re in a great team, then you learn from the tech lead and you learn from your peers, and the tech lead learns from their leader and their peers, all the way up to the CTO. But what happens when you are in a CTO role? You might have some peers in the C-suite, but you’re going to be bringing technical knowledge and up-to-date information to them, not the other way around. So, what I want to chat about with Andy is how, as a CTO, can you create your own community of peers?

Let’s start by talking about what were your aims when you started CTO craft?

Andy: 

So essentially, as a CTO, I’d been leading teams from their very smallest size all the way up to sort of 100 or so. And what I’d commonly see was that there was a lot of burnout, a lot of anxiety, a lot of isolation, a lot of loneliness in CTOs.

And actually, when I started freelancing as a CTO, I found myself in a lot of situations where the technology teams and the businesses in general were struggling because there was this isolation, burnout and, quite often, a lack of experience with leadership and that kind of thing.

And so rather than joining companies to pick up the pieces, I thought it might be a better idea to build something that would give CTOs a bit more support, because there does tend to be, as you say, a lack of support structure for people when they get to that Apex technologist role.

And that’s really where CTO Craft comes from. It’s a resource for lonely CTOs.

Zoe: 

Yeah, we all have this kind of myth, don’t we, that people who are in senior roles are somehow superhuman and impervious to anything going wrong, or, you know. So, I think that it’s absolutely necessary from that point of view. What are the other reasons why CTOs need a community?

Andy: 

So, as I say, it can be very isolating, especially for first time CTOs or all leaders in general. Where they’ve come from a place of being very, kind of, self-sufficient and very autodidact. And they’re used to being able to find solutions to challenges that they face on the internet (you know, like Stack Overflow if you want to copy and paste stuff).

And when you get to that leadership level, you’re very often just expected to, kind of, learn how to do it on the hop. You don’t get a lot of support in that learning.

It can be even more isolating and even more frustrating for people who are in that role. And they, more often than not, take the responsibility for that onto their own shoulders. And then that can lead to burnout and, you know, fearing that you’re letting teams and companies down, and so on, so forth.

Zoe: 

It’s such a different type of role, isn’t it? Because you’re almost fighting for independence all the way up, aren’t you? You’re like, ‘let me do it my way. I know how to work this out’. It’s kind of how you prove that you know what you’re doing. And actually, that blessing becomes a curse when you get into a senior role.

And also, you need a different skill set. You have new responsibilities, and not just, kind of like, more. I think there’s a kind of technical career ladder where you get kind of more of the same and an expansion of what you were doing already. Whereas the CTO role can be really where that tips over into totally new skill sets new responsibilities, being responsible for all of the team and all of the output.

Andy: 

Absolutely, it’s a career change fundamentally.

Most people get to that C-level by being the best developer in the company. But it’s quite often that, if they do that in a startup environment, the other leaders within that company don’t know how much of a change that is. And so, they expect them just to make that that leap, unguided and expect them to succeed straightaway, but very, very commonly fails.

Zoe: 

Yeah, it’s perhaps something where people in other C-suite roles have perhaps used, you know, more of the leadership and management skill sets earlier in their career. And so, they don’t understand why it’s such a big jump and a big shift for a CTO.

Andy: 

Indeed, indeed. And obviously, in the startup environment, there’s a lot of pressure to make the company work, you know. Essentially, they want to be first to market, they want to please the investors that might be knocking on their door, they have all these external pressures. And if the CTO is not capable of dealing with that additional pressure or additional workload, then things can start to fall apart.

Zoe: 

Hence, having a community of peers who are going through the same challenges that you are, it seems such an obvious need. In fact, I’m surprised there aren’t more organisations like CTO Craft.

How’s the journey been for you personally? Has it been fulfilling? Have you got stuff out of having founded it?

Andy: 

Yeah, huge amounts. Not just from the increase in the technical skills of leadership and management that I’ve learned. You know, part of how you learn stuff best is by teaching and by coaching other people, and that’s what I’ve taken from it personally.

But it’s surprised me how much of a nerve it struck. I knew it was an issue and I knew there was burnout and stress and isolation, rampant in startups for CTOs and technologists in general. But it didn’t really occur to me how many people and how widespread it was, and also that there was a spectrum.

There were people who weren’t necessarily on the brink of burning out. But people who, you know, just wanted a sounding board or wanted to know, they could go somewhere safe to vent, or just to get input of any kind who weren’t necessarily too far down that road.

But yeah, it’s been hugely rewarding. It’s the best thing I’ve ever done.

Zoe: 

Ah, that’s amazing. That’s really amazing to hear.

And I really get what you’re saying about how, as organisations, when we adapt for the people who are at the extremes, because we have to, because those people can’t function without these adaptions, actually, it can have really great benefits for people who make maybe making do or plastering over stuff.

So that’s a great side effect, I guess, of the really critical bit that that does need to happen, but actually, it’s great for everyone.

Andy: 

Absolutely. And there are other side effects as well. So, in a lot of cases, I’ve heard of people taking their learnings about how to be a leader and how to be a new leader, more specifically, back into their companies, and that spreading among the other leaders within the company, the other functions. So, it’s actually improved the workability, the culture of the company, as a whole, not just them in isolation, their engineering teams, which is brilliant,

Zoe: 

Because they’re learning from other people who are learning within their organisations. And you’ve already got that knowledge share. I love it. I love community and support and knowledge share, and it’s fantastic.

So, have you got any kind of success stories of like members who, I don’t know, maybe like a typical success story, or particularly poignant (Like ‘Amy joined us and then four years later, this happened’ kind of thing)?

Andy: 

We’ve certainly seen people move up the food chain, you know. So, CTO craft has been around for about five years now. We’ve certainly seen people move from leading quite small teams in quite a stressful way, moving up to leading teams of 200 or so, and having a much better support structure and leadership underneath them, etc, etc.

But we’ve also seen a lot of people who were in that burnout transition come out of it the other side and make their companies very successful because of it. And also improve the exhaustion levels and the resilience of their teams, as well. There is an element of ‘monkey-see, monkey-do’ in a way.

So, they’ve been able to take back to their teams that there are ways of improving the way they work, and then they’re not stuck with it. They’ve been able to change things.

Then, we’ve also seen large number of the people who’ve come to us for mentoring and coaching become mentors and coaches themselves. They’ve gone to the next level where they’re actually so independent and so confident in what they’re doing now, and the imposter syndrome has died right back and they’re seeing success, that they feel comfortable helping other people up, and that’s massive success, I think.

Zoe: 

Exactly, because, like you were saying before, that’s how you learn most yourself as well, right? What’s the saying… ‘Learn one, do one. teach one’ or something like that. It’s only teaching that really cements your knowledge.

And also, it’s how life works, right? You know, there are generations that move up and new generations come along and have to learn everything again. I think particularly with CTOs. Perhaps because so much tech is so new, but I meet so many people who seem to think CTO spring fully-formed into the world, and you’re either a CTO and you know it all already, or you could never get there. Because if you were destined to be a CTO, you would know it already.

I don’t know why it’s particularly prevalent in tech other than other roles.

Andy: 

No, I’m not sure either. You know, as I said before, it’s quite common to see the best technologists in a company be offered a leadership role. And, you know, jump into it, maybe without knowing really what that means.

But I think there’s also a problem of non-technical people grouping functions and grouping responsibilities in a way they shouldn’t. So, for example, the CTO role can be many different things, depending on the company, right? There’s a million different permutations of responsibility and types of person and aptitude that are suitable for those.

But I think people outside of tech (sometimes, not always) they might see it all as one thing, so they’ll think, ‘Okay, this person’s an amazing quality-focus developer, ergo, they’re going to be an amazing culture builder, as we’re scaling, as we got our Series A’ or whatever it is. And that’s not at all usually the case.

Zoe: 

And why would it be. You don’t say this person is great at coding, therefore, they’re great at football, you know?

That’s fantastic. So, let’s have a think about something that is a massive challenge within the technology industry. Again, it’s a challenge all around the world and all kinds of ways, but specifically within technology it appears to be a very acute problem, is the lack of diversity. So how can a community…

And I know that there are lots of organisations and lots and lots of startups building tech teams going, ‘We want to be diverse, we want to be diverse, we just can’t make it happen’. So, I think it’s very easy to end up with self-reinforcing tech communities, where people have the best intentions, but they’re not able to kind of get beyond the industry talent that’s already there.

So, what kind of things do you do at CTO Craft? And how can an organisation like CTO craft help with diversity in tech, and in tech leadership?

Andy: 

Yeah. Well, it’s multifaceted, obviously. But how we look at it is that part of the reason people from diverse backgrounds don’t join teams is because they don’t see a diverse leadership. That’s kind of the point at which we try to make a difference. Diversity among technology leaders is actually much worse than diversity among technologists and, as a whole, engineers.

That’s something that we can have some effect on, because we are offering services to leaders and offering community to leaders. So, the kinds of things we do, when we run conferences, we make sure there’s a 50/50 gender split, for example, in the speakers, so that it’s more immediately visible that there are women doing the kind of tech leadership roles that you might not have considered them doing 10, 15 years ago.

And then we also have people from diverse backgrounds doing weekly events and blog posts, and in future, we’ll be doing things like AMAs on the community and that kind of thing.

And also, in those events, sometimes we focus specifically on certain parts of the world and technology there. So, for example, we had an event recently, which was all about African tech. Very cool. It isn’t something you come across very often when you’re talking about technologists, and certainly not when talking about technology leaders.

But we do want to highlight that those are successful companies and they’re doing very well. They have great working cultures, etc, etc. And so, I think, as a community and as a as a publisher, which is what CTO Craft is as well, you know, we publish events and blog posts. Where we can help is just by highlighting people from diverse backgrounds in leadership roles. If the hypothesis is correct, seeing more people in leadership roles will hopefully improve diversity in less senior roles. That’s the hope.

Zoe: 

Fantastic. Well, we’ll check in in 50 years’ time and see how it’s going.

I really like as well this not all important tech leaders are in Silicon Valley. Right? I feel like there’s so much focus on that and obviously amazing people are building amazing tech all around the world all the time. It’s not confined to one tiny part of America.

All right, well It has come up a few times already. Let’s dig into this topic of burnout and stress. Because like you say, startup environments are themselves stressful. And very often, in fact, one of the key outputs of the startup is the technology. So, delivering technology is in itself stressful in the best of circumstances.

So, then compounded with this business pressure of, you know, the whole business could not exist if this technology isn’t built, how can a community like CTO craft help with stress and burnout?

Andy: 

I think showing that it’s not isolated to them as individuals. First and foremost, we do more specific kind of coaching and educational stuff, and so on and so forth, for people who are burning out. But really, the biggest thing is that they’re able to see that it is widespread, and other people suffer from almost identical symptoms to them, and almost identical causes to them as well.

It’s incredible how common the flow from being an engineer or being an individual contributor, to being a leader, leads to burnout. And not just in technology, but you know, that’s our kind of sweet spot. It is just very common. And it’s very common that they won’t get support with it within their company as well. And certainly not from investors and so on, although that’s, that’s starting to change.

Seeing other people who are feeling the same stresses, they’re encountering the same blockages, and just being able to talk about it and being confidential, they know it’s not going to get back to people within their organisation or other CTOs within the portfolio or whatever.

Zoe: 

Yeah, so basically, like depersonalised it, like making it clear, it’s not a personal failure. That’s often the first thought, isn’t it?

When something changes, say something in your life, and you’re like, ‘Well, hold on, I didn’t feel like this before and I’m not doing all these magic things I’m supposed to just be magically able to do like, there must be something wrong with me’. It’s actually making people realise or helping people to realise it’s the situation, is super, super important.

Andy: 

I think also offering an avenue for people to distract themselves a little bit as well. So, I think it’s very easy when you’re in that spiral, to just kind of only give yourself energy and only give yourself resource to focus on the work in an attempt to sort of dig your way out of it. But I think having people who are doing similar things, talking about interesting stuff that, you know, might be of interest to you. I think it’s a good distraction as well.

Zoe: 

Well, that really neatly brings me on to my next question, which hardly ever happens. Like, for me, it’s just so clear the benefits and why this kind of external community of peers is so important. But we’re talking about people who are really busy and stressed out already. How much time can CTOs really justify spending on something that isn’t their day job or isn’t directly contributing to shipping some more code?

Andy: 

I think that’s the key, isn’t it? Is their day job just shipping code? I would say it’s not. If they’re responsible for a team of people than their day job includes, but it’s not limited to, getting better at that. In the same way, you would hope that developers within a team are spending some of their time building their skills and getting better at what they do. You know, leaders need to be capable of doing that as well.

Zoe:

Yeah, excellent answer. And actually, it’s the answer that goes right to the crux of the whole challenge, right? You need to build new skills. You need to spend time on building those skills and supporting yourself in building those skills. I feel like so much of life is just letting go of this idea that everything’s magic, and everything happens by magic, you know. Things take time, skills need to be learned. No one’s perfect. You know, all of that.

And that’s where exactly like you say, just having honest conversations with other people, and realising that, actually, they’re not… even your heroes aren’t magic. They’re just people, and often built up their skills over such a long period of time, you know, talking like 20, 30 years, they didn’t just magic it into being… when they got a new title, you know.

Andy: 

That’s it. And there’s also a good chance that they’re still struggling with the same things they did in their first CTO role.

Zoe: 

Well finally, what other ways can CTA start to build a network of peers?

Andy: 

The most common way of doing it that I’ve seen is through investors and through their portfolios, so it’s quite common for VCs to put together a message board or a WhatsApp group, quite often these days of CTAs within their portfolio, and that can be quite a good way of just kind of having other people to tap on the shoulder.

In some cases, I’ve even seen a portfolio CTO under investors who was kind of almost like a group CTO who doesn’t get operationally involved but is there to kind of support people and coach them and help them through challenges and that kind of thing that can work quite well.

Zoe: 

Wow. That’s like a private CTO craft. Just for their portfolio.

Andy: 

Yeah, with a group size of 15 to 20, as opposed to, you know, however many 1000 we’ve got. That’s the most common way.

Other than that, local groups, you know, there are still meetups, although they’re all running virtually at the moment. But there are still meetups in many cities around the UK and right across the states. And that can be a good way of finding people that you can just go and have a coffee with as well, you know, at the right time, obviously. There’s also open-source communities, you know. A lot of people who are building software using some kind of open-source framework, the leaders from those teams, I’ve seen have private groups that they compare notes on, and so on. But that’s it.

Zoe: 

Yeah, of course. And then finally, communities like CTO craft and events, you know, tech events where there are people speaking and then also other attendees – I think that’s such a valuable source of community. Or a way of meeting people who can then form part of your community.

Well, thank you so much, Andy Skipper for your insight on this podcast and also for the fantastic support that you put been given to CTOs now for is it five years?

Andy: 

Four years.

Zoe: 

Amazing. If you’re listening, and you’re looking to start building your own community of CTOs, you’re always welcome to hit us up at software or hit me up. I’m Zoe Cunningham. We have podcasts, blogs and videos that can support you on your journey. Or, of course, do think about joining CTO craft by heading over to CTOcraft.com and leaving your details. Thank you, Andy.

Andy: 

Thank you very much. It has been fun.