The Journey to Becoming a CTO: Tips for Aspiring Technology Leaders

Hi, Andy.

How are you doing?

Hey, I'm good. Thanks, Mike. How are you?

I'm, I'm good as well. So one big question, Andy, do you have any big goals for this year?

Oh, well, um, we are rolling out more in terms of learning products and Events, we've got a bunch of local events that are rolling out in different cities around the world. Yeah, that's primarily it, creating more content, more value for CTOs.

So just growing CTO Craft, which leads to our very first question, who's Andy? Introduce yourself.

Yeah, for sure. So I'm Andy Skipper, I'm the founder of CTO Craft, which is a learning and mentoring community for senior technology leaders. And I was a CTO for a long time, then a fractional advisory CTO, and then fell into coaching CTOs by doing that. And CTO Craft originally was a platform for my coaching practice. And now it's grown way, way beyond that. And it's 16,000 people, it's conferences, it's Yeah, it's huge.

So you can be part of a free community, right, on Slack? Anybody can join?

Yep, exactly that. Yeah, so it's, it's a, a free community at the, at the heart, and then we have various subscription-based things like mentoring groups and coaching and e-learning, and then we, we have the conferences and events as well.

Yeah, and I myself, you know, I've been part of your coaching circles, and I've been, you know, to a couple of CTO Craft events. So from our perspective, you know, these are very great and very needed for UK industry. And happy to have you on the show, Andy, by the way. So let's—

yep, sorry, I was just saying thanks for having me. Sorry, maybe we do that bit again.

Of course, I will. I do hope we will do that again. All right, so we've got a couple of questions to dig in, Andy. So we'll start with the market, you know, You are so close to CTO communities, like 16,000 people on Slack. Everyone's talking about, you know, who's hiring, you know, which business looking for CTOs. What's your general take right now, how the market looks like, and maybe, you know, a year back, and how you feel this year will go?

Yeah, so the last year has been really tricky. You know, there's nothing complex around that really. I think the amount of funding and the amount of money available to founders and startups in general is just that much lower. And to begin with, it meant freezing some of the hiring strategies, some of the hiring plans that startups had in particular. And now I think it's evolved a little bit into CTOs actually finding themselves on the sharp end of those redundancies. And then finding it quite difficult to find new roles. And so, yeah, it's now a case of CTOs competing quite heavily for a much smaller number of available roles on the market. I'd say this is very much true in the UK and Europe, but from the sounds of it, it's also happening in the US. Yeah.

So generally, we just have less money in the whole market. Just liquidity dried up, less funding, less organic growth, just less capital, which leads to the, you know, big layoffs. And we've seen that, we've seen that big tech layoffs, which probably, if I remember correctly, that kicked off in the beginning of last year. Do you feel like it's still happening at like high scale where big companies are laying off like thousands of people or that layoff is sort of, you know, a lot more steadier and we just sort of looking for a bottom and we hope to recover in this year?

I'd say in those bigger companies, it's still pretty prevalent. You know, some big, big rounds of redundancies announced just this week. But in the startup world, I think it's just, there's just quite a lot of fear and uncertainty about what kind of growth they'll be able to manage without growing their teams, essentially. And obviously, for the CTOs themselves, concerns about whether there's a role for them.

Yep, that's true. What about salaries, Andy? Do you have a sense of— so we have layoffs, uh, a lot more competition for existing roles, which often pulls down the salaries because businesses can choose to pay less and there's still people taking those roles. Like, do we see the salary shrinking or the salaries are okay?

Yeah, I'd say at the very least they've stayed static. I wouldn't be surprised if they have come down a bit. I don't have the, the latest numbers in front of me. But I, I would say they've definitely not gone up.

Yeah, definitely not 100%. And it's usually how it happens, isn't it? It's like you get the layoffs and then just, just so, so much more people willing to take the roles at the, at the lower rebanding for these roles.

Absolutely.

Yeah. So outside of just no money, do you think there's any other economic factors driving the layoffs across the tech sector?

Not that I'm aware of. I mean, I think there has been some scrutiny over technology companies and the technology industry in general that there maybe wasn't from 2005 to 2020. There have been some big scandals. There's a renewed focus on privacy and data security and all that sort of stuff. Yeah, I think generally speaking, it's more to do with the the ripple effect that the pandemic had and the sense that the attitude to risk wasn't quite right for some of the institutional investors. But the flip side of that, because they haven't stopped raising money for those funds, is that there's now a lot of what they would call dry powder, some money they've got available to invest which they haven't invested. And I think, you know, you know, with my optimistic hat on, I'd say we're going to start seeing some of the, the general partners and the limited partners in those investors start to say, well, hey, we're not going to get any return if we're not investing this money. And so we might see an uptick, we might see an uptick at some point, um, because they can't sit on that money forever.

Yeah, so effectively the uncertainty forces into this defensive mode where where businesses and investors just hold in cash. But effectively, how long can you hold, hold on them, right? It's just a sitting duck. So you want to, you want to put and allocate somewhere. So potentially, that's why you're saying it's, you know, maybe that those funds gets allocated again and we see some uptick.

Yeah, indeed. Or another potential outcome is that, um, you know, family offices, high net worth individuals, people who would normally be limited partners in these investors look at different options for investing their money and the money available to the startup world drops. You know, if they see that VCs aren't investing the money that they're putting into those VCs, then chances are they will find other ways of growing their capital elsewhere, which is not good for startups.

Yeah, it's many questions. So So are we saying this is a, like, a sector-specific downturn, or is it more of a reflection of a larger macroeconomic trend? Effectively, is it tech only, or is it just the whole—

yeah, I think it's market-wide. I think it's market-wide. You know, we've seen the same things in real estate and, um, you know, retail, very much so. Um, I think tech comes under a lot more scrutiny because it's, it's still reasonably young and reasonably untested. There's still quite a lot of volatility in tech markets that we don't see elsewhere.

So we just go through these busts and booms a lot more in the tech industry.

Indeed, indeed.

Yeah.

And, you know, because we're innovating at a much higher pace than the retail or the real estate or the minerals markets. You know, maybe there are new opportunities showing up and then disappearing quite quickly. So yeah, it is just more volatile.

So effectively what we're saying, it's, um, these signs of layoffs isn't long-term, right? It's just sort of like a temporary readjustment to the, you know, global market conditions, and we expect things sort of pick up again. Um, how are these layoffs impacting talent pool and especially the The hiring practices, in your view?

Yeah, it's an interesting question. I mean, in theory, from looking at it, it should mean that there's more good talent on the market, right? And I think there is quite a lot of competition for that talent though. So good engineers, generally speaking, rarely find it that difficult to find a good role. I think coming back to the point you made earlier on, they might be taking lower salaries or setting their expectations a little lower, but they don't tend to be on the market for too long, even if they've been made redundant. Some of those companies that have made redundancies, they're obviously freezing their hiring or only hiring in, you know, multi, multi-skilled people or T-shaped people. Those people are even harder to find, right? So they may be dropping their expectations, they may be paying more for the fewer T-shaped people than the higher kind of very specific skilled people. Yeah, I'd say that in terms of hiring practices and kind of how people are going about looking for them, I think there's a lot more word of mouth at the moment. So what I do know is that the, the placement sector, the recruitment sector is having a really, really tough time at the moment, which implies to me that more people are finding good talent through their own networks or, um, or through VCs they're involved with or whatever, rather than using a headhunter or a recruiter. And yeah, that, that seems to be a trend right now.

Yep, that's— I, I can Second that very, very strongly. You go to third-party recruitment when you cannot fill the roles yourself. If you just go in and you post, you know, a job on LinkedIn or Indeed and you're getting, you know, a bunch of candidates sending— like a proper candidate sending you CVs, like there's no need to pay that fee. So, so, so people just get, you know, get, get enough talent coming in and And that's effectively, you know, tough days ahead and already been tough days for recruitment industry. So would you feel like in your experience, like when it comes to offshore, so we had a guest talking about the challenges finding a good quality to price ratio candidate in UK. As a result, companies looking, you know, offshore and looking to other countries. You know, going to Europe, Ukraine, Bulgaria, Romania, Poland, you know, Lithuania, these countries, and as well going South Africa, effectively looking offshore to get a similar value or a similar talent but cheaper.

Yeah, yeah, and still plenty of people looking for entire teams, in some cases just individuals, but through an umbrella company, for example. Yeah, still happening.

So when it comes to like CTO craft and, you know, potentially messages around, do you see that fractional CTOs doing work outside of their countries? As in, you know, say I'm a, I'm a CTO in UK, but I actually work for States or, you know, Europe or whatnot. Just when it comes to hiring CTOs, is that an often operational module to hire a remote CTO?

It depends on the culture of the existing team, I think. There are certainly fractional CTOs that I've spoken to who are working with companies in completely different continents, right? But there are some companies for whom having somebody who wasn't physically in the office in a top-level leadership role just wouldn't be possible. So yeah, it happens, I think. Depends on the person, depends on the company, depends on which continent they're in. You know, I don't know of any of the fractional CTOs that I'm talking to who are in the UK working with a company that's based in Australia, for example, for obvious reasons. But it certainly happens. Yeah, same with coaching.

I do see coaching because it's almost like consultancy, isn't it? You come in, you take some some outcomes, or with the fractional roles, it's not the whole role you're doing, you're doing like a fraction of that role. So potentially can be done, you know, remotely, but you do have a, a very big role as a CTO for any company, and being present, it's still a lot more of that than being remote, isn't it?

Yeah, as I say, it depends on the companies. So some companies have a, a completely remote-first culture in which case you don't need to be sat next to somebody.

You're right.

I think regardless of whether it's a permanent CTO or a fractional CTO, if that company works that way, then it'll work. If it doesn't, then it probably won't.

Let's define CTO as in, you know, CTO role description in a way, because I feel like from your perspective, an individual who you would call CTO outside of title? Because I feel like for startups, you know, you could be a second person for a startup and, you know, effectively you are hands-on and maybe senior coder and you can have a CTO flag, which in real terms or in a broader market terms, it's, you know, unlikely you would get a CTO in a much bigger company. How do you, in view of you, like what skills do you need to have to be a CTO?

But as you say, it depends on the stage of the company. In fact, it's very, very tied to the stage of the company. You know, in the earliest days when you're trying to reach product-market fit and where you're purely innovating, where you're only creating new value from scratch, you kind of have to be very hands-on, you have to be very experimental, very code-focused. And then I think as the company gets older and older and moves through the different stages in its life cycle, the person has to be more leadership-focused and more commercial-focused and then more strategic-focused gradually as it goes along. But I think the CTO title really doesn't mean anything other than the most senior technology person in the company, fundamentally. And so outside of that, the actual skills you need or the, the things you do change pretty dramatically based on where you are in the company's life cycle.

Yeah, I get it. I like the definition of fundamentally you are the person who will make the technical decisions and you will need to account for that because there's no one else above you to share that accountability. So effectively, if you're in that position, you are the Chief Technology Officer, isn't it? And it's just exactly the challenges, they, they all resonate with the size of a business and the size of a product. Is there a, is there a skill you see which is either ticking up in demand, or maybe already ticked up, but you know, it's still growing? And so if I'm thinking about, you know, maybe I want to be CTO in this year, what type of skills or new demands you, you think I should be looking at? Do you upskill myself?

Well, not specific to technology leaders, but certainly relationship building and creating a solid first team, understanding who your direct responsibilities are most aligned to. But I'd say, especially in the ecosystem we're in right now, commercial understanding, understanding of money, especially in startups where you've got to have a clear idea of not just where the money comes from, but also where the money goes right across the business. And so you know which parts of your day should be spent on reducing cloud costs or making a decision as to whether to hire someone or whether to build or buy, etc., etc. But without having that understanding of the commercial side of the business, you're kind of guessing or you're relying on a CFO or the CEO to make those decisions for you, which is quite limiting, can be quite dangerous. So I'd say those two things, commercial savvy and communication relationships, etc. Yeah.

But both of these will work in any role, isn't it? If you would go to a startup which has AI product, you know, by default, they would probably look for you to having some, you know, some skills in machine learning or understanding that market. But those two, relationship building and commercial understanding, they're applicable to any, any business you would go to work for, isn't it?

Yeah, absolutely. Yeah.

So let's take a little bit in that commercial understanding, you know, the buy versus build. I feel like this comes, comes very often, and I do see a core level coders or CTOs which come from, from that background of doing everything themselves, they, you know, writing and coding the products themselves, they often do that mistake. And when they look at the challenges there and they always think, how can I make this happen, instead of, you know, who can this make happen for me, you know, maybe you want to integrate with the service, maybe you want to buy a solution. Uh, from your view, Andy, How you train your mind or how you ask questions around the challenges you have to actually make a good decision, buy versus build?

It's really tricky. Again, it comes down to the stage of the company, you know, and where you should be investing your money and your time. You know, if you can invest in a whole team to build out an ERP system from scratch that you know is going to be completely unique and tailored to your business, if you can afford it, maybe that's the best way to go. But if not, and if you're getting off the ground and, you know, you have limited time to get something out there, whatever reason, then, you know, buying is probably the best option. So yeah, I don't think there's a one-size-fits-all answer to it, to be honest.

Okay, I like that. A lot of companies buy, like, if you look at bigger companies, the merchant acquisitions is fairly You know, it's very often because not only you need to build this in it, then you need to maintain it, then you need to actually push that out. So you got to be competing, you know, for the market share. Sometimes, you know, just going in and buying, it just becomes a lot easier than, than trying to climb the Everest. Um, from soft skills perspective, uh, for a CTO, you mentioned the relationship building. So if we take these, um verticals of leadership, communication, and vision. Um, any of these for you come on top, as in being more important?

No, I think it's pretty evenly spread. You know, none of those can exist without the others.

Okay, how do you showcase these soft skills and, you know, stand out in like purely technical crowd? And we're talking now about, you know, I want a security role, right? So how do I How do you show that I have this?

Sorry, ask the question again, Mike.

Yep. So you got leadership, communication, and vision, right? Um, you're saying they're all equally important as soft skills, and in interview process, or maybe CV, or maybe to general market, I just want to show that I have this as skills because, you know, I'm, I'm competing for a CTO role. Any tips how you can sort of come out and show that you got that?

So always in interviews, I'd give examples. I'd talk about actual situations or actual stories where I'd had to execute or exercise people skills, I would call them, rather than soft skills. I think soft skills is a bit of a negative connotation, but the ability to negotiate with people, the ability to compromise, the ability to coach people, if there are specific ways that I've had to call upon those skills. And, you know, exercise some emotional intelligence, for example, then I would talk about those in an interview. Yeah, there is a lot of jargon around that stuff, a lot of acronyms. I wouldn't use that. I'd use actual real-life situations that I've been in.

What if you don't have real-life situations but you feel like you could handle them? So effectively, you start talking, you know, conceptually 'You know, this is how I would do it, but you know, that's not something I dealt before, but I feel comfortable I could get it done.' Is there any suggestion or tip how you can spin it and still, you know, come out as, you know, 'Yeah, I know that.' Yeah, I think if you've been in any kind of leadership role, then you have exercised your people skills, whether you recognize it or not.

So maybe it's being a bit more creative about how you pull stuff that happens on a day-to-day basis. And you know, when those situations, those scenarios, they don't have to be big and mind-blowing and, you know, life-altering. They can be just day-to-day things. This person came to me, he feels like he's not growing in his role. So I had a chat with him about my experience. That's good enough, right?

Okay.

Yeah. So people skills. And soft skills, if you want to call them that, are not about big overarching kind of situations and big bang things. It's about how you build a culture around people and understanding people and talking to people.

So negotiation, that comes quite often, and I think everybody will deal with that eventually when they will have some sort of conflict or disagreement how you move forward. And at that point in time, you know, you want to get people on your side and you want to negotiate that, you know, your, your side of the equation is better, or at least, you know, um, you think it's better. Anything from this perspective of how you would— like, is there any— again, is there any tip or just, you know, communication of how we move about? I have an initiative, you know, I want to get it done, but I do have some pushback. Like, how do you overcome that?

Yeah, it can be really tough, especially if you don't already have a good relationship with the people, which is why that, that relationship building piece is so important. And then there are certain psychological tricks and approaches and, you know, concepts like reciprocity that you can call on. But really, if you get to a point where you're having to negotiate with someone who really doesn't want to get on board with the what you're saying. That's the only situation where I think you should use some of those techniques and psychological approaches and so on. There are some great books on this stuff, but I'd always go for having a good relationship in the first place.

That was my question. I wanted to sneak in any books you would recommend on that, any titles you remember.

Never Split the Difference is a good one. To Sell Is Human, that's a good one. What else? Switch is a good one. Influence by Robert Cialdini is a good one. Yeah, there are plenty of books. That's a good one.

Never Split the Difference is that Ross I forgot the name.

What?

Ah, I think I know. Yeah, I know that book, The Sell to Humans. That, that one's Switch and Influence. That, these are not known, so I'll, I'll check these. Thank you for recommendations, Andy. We'll put it in the show notes if anyone interested as well. So we've got negotiation, we got compromises, conflict resolutions, and in general people skills and building relationship as a very first one. So let's say you walk into a new role, you know, and effectively you inheriting a big team already. So you're not gonna build the team from scratch, you're not part of organic growth somewhere in the startup. You walk in a room, you have a bunch of people. Is there a go-to techniques you use to start building relationship?

Nothing more interesting than one-to-ones. Realistically, it's just spending time talking to each of the individuals within the teams, and especially your direct reports, just trying to get under their skin a little bit, find out what motivates them, what things are driving them nuts, et cetera, et cetera. But it's all just conversations.

So we have a head of engineering who effectively slots in the middle in the organizational tree. So, you know, he or she has direct reports, and as well, he or she reports, you know, upstairs. Do you feel there's a difference of how you should build a relationship? Like, should I go first with my peers, or should I look at the team, or no difference really?

I don't think there's a huge amount of difference, to be honest, but I would always talk to the people above me first and then to the people beside me. And then to the people below me. That, that would be my order of approach.

Okay.

But really, you, you'll find useful information in order to kind of get up to speed from all of those levels.

I do agree. I remember I read somewhere that you should, you should think, you know, that all of the managers you have is actually your, your first-degree peers, and you, you probably want to build a relationship with them first because they will help you to, to move things. If you get stuck and your team comes back and goes like, you know, here's a blocker and, you know, effectively your job will be to unblock them and you will need to go talk with your peers. So you, you want to have that relationship sorted to get things effectively unblocked and moving. That's just capturing small wins. So let's say you are part of a startup and, you know, you just did well and, you know, maybe you raise money or maybe organic growth and you got the board. Right, so, and you are CTO, but that's your first role. Any tips of how you can, you know, bridge the gap between tech geniuses and, and the, you know, boardroom brilliance coming in, you know, doing presentations, uh, and all that part?

Yeah, so I suppose from, from my experience, what a board wants to know is where the risks are. You know, it's different from a management meeting where they want to know what the strategies are and what how they're going to grow, how they're going to build. An investment team board, they kind of want to know where the potential risks are, what might stop you from growing or might stop you from making money or might be burning more cash than they're comfortable with. That's been my experience. It's not universally true, but to find a board who is interested in the actual kind of strategy and planning and tactics in terms of actually getting involved in creating them, um, is quite rare. But yeah, as I say, not universal, my experience.

So it comes back to that commercial brilliance you talked about before, as to two main skills: relationship building and understanding the commercial landscape as a CTO, because you'll need to take that back to the board and, and talk in their language effectively.

Yeah, that's it. And also being able to translate it back to the technology team. So, you know, if they do have concerns about certain areas or certain initiatives, or, you know, as we've seen lately, maybe there's a funding crisis coming up at some point, and, you know, it's being able to translate down the chain.

Yep, I get it. Okay, so you are CTO now. How do you convince the leadership, potentially the board, that you're not only coding for today but you're actually, you know, thinking and shaping the tech of tomorrow? So effectively, that vision piece, as in, how do you— like, any tips as well, or your own sort of ways of how you look at, okay, this quarter is this, but what's going to happen about, you know, after 12 months?

I suppose that comes down to alignment of strategies and understanding what the business objectives are. And then it's just a case of being able to, you know, going back to that translation, translator description, you know, being able to translate the business objectives into technology objectives and strategy. And if you can't draw a direct line between the two, then, you know, it's going to be much harder to sell to the board or to the management team. And that, that's why quite often management teams and boards will push back on, uh, you know, a, a large rewrite, for example, or a large over-engineered, in their mind, approach to an architecture or whatever. But, um, yeah, it's being able to, being able to communicate the, um, the value or the risks of doing everything quick and dirty as opposed to taking the right time and putting the right foundations in place.

And it is always quite challenging, isn't it, to come in and go, you know, we need to re-engineer everything because technical debt is out of control and, you know, any work we do takes 5 times more than it should be. Selling that will be quite difficult. So you always Wanna think about return of investment on time and on money and just try to translate that in some type of tangibles so the business understands. That was my sort of follow-up question, but I think you digged into that. It's like, but if you think that's the— a must, how you— how do you still go about making sure that you get the time and get resources to actually get that done?

Well, the question is, should you? You know, that's not always universally true. A CTO might come into a company and see there's a huge amount of technical debt, there's a huge amount of cultural debt, et cetera, et cetera. And they talk to the business, they find out that there is a, you know, there are challenges in terms of burn rate and in terms of market fit. And so on and so forth. Is the right thing to do rebuild the team from scratch or rewrite the system from scratch? Probably not. So, you know, it's part of the CTO's role to know what the right solution is rather than just pushing for, you know, what should be the cleanest solution.

So is it more about like the path of least resistance towards profitability or revenue increase? Versus—

No, not at all. No, it's about the business's objectives. And if the business's objectives are just make money, stop losing money, then that's, you know, I think that company's probably going to struggle. But it's understanding the timing, it's understanding the market conditions, it's understanding what order things should be approached in. And then most importantly, it's about knowing what it's going to cost to implement the different strategies and the different tactics that you might choose. That comes back to that commercial understanding and being able to budget and forecast and understand things like opportunity costs, etc., etc., etc.

So I like this market condition saying that's effectively If you think of around your decision matrix, that, that will sit very high at the top because it's just like, what's the economy, you know, what's the market, what's the industry you're competing in? Do you have your ways of how you source information about that, like blogs, some companies, research industries, or whatnot?

Yeah, I mean, ideally it would come from within your company, right? It would come from the rest of the leadership team. Would come from the board, who would come from other investors. But then, you know, there are plenty of publications around that talk about the state of funding, the state of AI, the state of et cetera, et cetera. So yeah, I think I would like there to be communication about that stuff internally from a CEO to a CTO, for example. But yeah, there's nothing stopping a CTO from going out and educating themselves on the, on the industry they're in.

I feel like there's some topics which you, you'll probably need to lead that education, like, you know, security, uh, cloud, you know, maybe there's new players, maybe some technology is getting, um, you know, going from early adopters to majority of, of, you know, adopters, and what that tech brings. Maybe there's a value, maybe there's a cost saving, maybe, you know, can accelerate development. That will probably will be your domain to know about. Anything else business-related, that's— yeah, that's a CTO, probably different departments. So I got difficult one, uh, I feel like it's difficult one. So women in CTOs, or just diversity at the levels of CTO. So I feel like this comes a lot, like there's a, you know, female numbers-wise, you know, male number-wise in CTO roles. Like it's not, um, it's not on par. If I'm a female and I want to be CTO, is there any specific, you know, hacks for navigating CTO scene, or it's just pure skill?

I don't think there are any hacks for becoming a CTO if you're a woman specifically, or any underrepresented minority, to be honest. I think it's more a case of getting people into high enough level technology roles so they then become leaders. You know, women are much more likely to drop out of technology before they get to C-level kind of roles. So I think it's, it's, it's more— it's, it's a trope, but it's more for men to, to make it easier for, for women to, to get into those top level roles than it is for women to have tricks and tips to get into them. I think it is tools.

Yeah, sorry to jump in, but there's no tricks and tips, isn't it? It's just, just the pure knowledge, experience, which then becomes a skill, and then you're competing, you know, for the role. It's, it's just, it's just that, isn't it?

Yeah, I think so. I think there's a bit more to it than that from a social point of view, socioeconomic point of view as well. But yeah, absolutely.

Do you think—

But it is about getting—

Yep.

It's about representation. It's about making it easier for women to get to the point where they could take C-level roles. Unfortunately, that is still very male-dominated. It has improved. And now I think we're starting to see a bit of a backtick. In terms of number of women going for those C-level roles. And it's about representation, it's about women seeing other women in those roles and succeeding in those roles, most importantly. So, you know, that's part of the ethos of CTO Craft, is that we give representation to underrepresented minorities. So our conference lineup's always 50/50 male and female, for example. But it is tough, it is tough, you know, there are fewer CTO roles in general, as we said before, and the competition for them is much fiercer. And in competition for those kinds of roles, men tend to come out on top, unfortunately. So it is just, it's just a hard ecosystem for women in those top-level leadership roles. And only men can do something about that, right?

I hear you. No tips and hacks, but just getting represented and potentially leveraging your network, which leads to my next question. So beyond LinkedIn likes and social media likes, any tips how you can leverage your network strategically to land the CTO role? Or just find the CTO role opportunities to compete for.

For women specifically or across all genders? Across. Yeah, I think building out a network, especially a local network, if you live in a specific city. So, you know, if you live in London, then finding groups of CTOs in London who share roles. Yeah, there's, there's a lot of personal brand building at the moment on LinkedIn. A lot of CTOs, especially those who've been made redundant, are all branding themselves on LinkedIn in fairly similar ways. Um, so I think that probably has a fairly short, um, a short, uh, shelf life. I don't think that's going to work forever. Um, I think it is just getting out there, getting to know people. When I became a fractional CTO, the way that I built up my pipeline of work was by networking, not just with CTAs, but with investors and coworking spaces and doing stuff for free, appearing at events, doing free mentoring, advisory work, et cetera, et cetera. And just building out my, you know, building out people's awareness of who I was and what I specialized in and the kind of work that I do. I think, um, personal branding by posting links and, you know, writing content is probably only going to get you so far. I think there probably needs, needs to be a bit more getting out there, shaking hands, doing some good, and you know, people will get a better picture of what you are and what you do and how you can bring value to their company.

Yeah, I very strongly agree with that. You know, actually going to events and, you know, pressing the skin, as they say, and talking face to face. One good event, which is probably not free, it's probably going to get, you know, be paid event, but where you have an actual industry leadership coming in an event and, you know, going there and having conversations with people, that will— that one, you know, hour or one day of that event will have a much, much bigger return of investment than you spending the same time writing, you know, a blog post and sharing on LinkedIn. That's, that's my personal opinion, and my— which comes from experience as well. So very strongly agree with that. Well, coming back to personal branding, and you know, I do see the same thing which you mentioned, and I see it in, in more social medias as well, where people, you know, are trying to build a brand around themselves. You mentioned that you think it has a short shelf. Do you feel that's just gonna stop when market recovers and people will go back to work, or do you have other opinion why you think it's just, you know, short lifetime?

It's a really good question. I think probably it's a question of the motivations. So, you know, a lot of people are doing it because they're looking for work right now. And some of them are looking to build a portfolio of work. So, you know, quite a few of them are moving from permanent CTO roles into fractional CTO roles or into coaching or whatever. I don't see that slowing down. There is definitely an imbalance between supply and demand for fractional and coaching-type roles. So, you know, does that mean people will stop when they realize they're not getting roles? You can say, right, it might suddenly start working, might be working now. You know, I'm not doing it myself, so I don't know fundamentally, but Yeah, we'll see. It seems like a short-lived thing. It's very zeitgeisty. There's lots of people who build a personal brand around personal branding, for example. So yeah, that's my opinion. I haven't seen it work very well.

I want to say that I agree, and I have an example which happened during COVID with with people getting stuck at home and they're going like, you know what, I have time, so I'm gonna launch a podcast or I'm gonna launch a YouTube channel. And the moment market recovered, people just went back to, you know, either jobs or startups, and all of that sort of just toned down. So if you look at the podcast industry, there's a huge spike of podcasts coming out, you know, during COVID as in just like number-wise. And then it just stops after like 10 episodes because people just went back to work. So I feel like that, that could be exactly the same thing where, where we have so many CTOs, you know, being made redundant, or technology leaders being made redundant, and they have time on their hands. And, you know, they go like, you know what, I'm gonna go in fractionals, I'm gonna go in coaching, and they start to build out that name. But the moment market recovers and they get a good job, good paying salary, interesting projects, you're gonna be like, well, I'm gonna pause that branding exercise, just go back to do something that pays. I feel like that could be a very similar situation. So you mentioned motivation and coaching. So I feel like if you're motivated now to do personal branding and go into coaching because you don't have work or you cannot find work, do you feel that that's a wrong motivation to start, you know, being a coach? Because for me, coach is like you either good at coaching, like, you know, you like, you have that personality of coaching, or you learn to be a coach. But that's for me, like, it feels like it's going to be two different personas, and they will probably going to have two different results as a coach. Um, just, just so the question effectively would be, do you feel anybody can become a coach, a good coach?

Um, anybody can become a coach, that is definitely true, I think. And anybody who has any kind of relevant experience can become a mentor and a, you know, and a coach as well, you know. Um, can anybody become a great coach that can have real kind of long-lasting impact? Probably with a bit of practice, but I think you have to have a certain type of personality as a coach. You have to have a certain type of openness. You have to know how to communicate with people in a certain way. And those things can be learned, and some of them can only be learned by doing for a certain period of time. I don't think you necessarily want to leave a well-paid permanent role to jump straight into it from day one. I think it would take you a little while to get up to speed and you're probably not going to make as much as you did in your previous role. You know, people don't enter coaching to supersede it. They generally do because they have something they want to pass on or they want the flexibility. I've seen a lot of people become coaches or fractional CTOs because of the flexibility it offers. So you're saying that's a perfectly valid reason.

So you're saying there is a very real cut on the salaries you take if you're gonna go, or eventually you build up to the level where you, you know, you are a fairly expensive coach and, you know, maybe you have— or mentor— you have good clients which you can still compete for the same salary, or, or it's just or it just comes with the territory where you expect, you know, 20%, 30% cut, where you're happy to take that cut because of the flexibility you get?

Yeah, I think it's a pretty broad spectrum, but generally speaking, you won't leave a permanent role and immediately be able to completely replace the salary you lost.

Okay.

That's very unlikely.

Very unlikely.

But yeah, you can totally work up to that though over a period of time.

That's quite nice. Um, let's say I want to be a coach, but I never was a coach, but I feel like, you know what, I'm doing this at work, I feel like I'm, you know, I'm good at it, I want to do this professionally. Can I read a book, How to Be a Better Coach, and would that actually work? Should I instead just offer free coaching sessions on LinkedIn and just you know, go into to see how that market, you know, works. Any tips of how one, if they're considering, would be able to transition from that perm role we just discussed to being a coach/mentor?

But you should certainly read the books. That's, that's not the answer. That's not the answer, but you should always be reading books and building your skills and, you know, gaining new models, learning from others' experience. But I think realistically what you should be doing is offering mentoring sessions as opposed to coaching sessions within your network to people that you trust and who trust you in the first instance. That's probably the safest way of doing it. And then outside of your network on LinkedIn or whatever, and then charging people.

Yeah, I do like things. Yep.

Yeah, that's the order I would approach it.

Just read books, get some conceptual knowledge, have no commitments, aka do it for free, and try these things out, you know, see how they work, develop some type of framework, how you approach the sessions, how you follow up sessions, and just work things out. And the books, if you remember title-wise, because you gave like 4 on the, you know, on the negotiation. I felt like that, that's a lot. I didn't expect even one.

Can I match 4? Um, the, the Coaching Habit is, is always the one that people start with. It's the most straightforward introduction to it. Um, The Coach's Coach book is actually very good. I was talking to the author earlier on today, actually, um, which is brilliant. It's a, uh, a list of certain coaching client types and different approaches and like real-life examples of conversations he has and, um, techniques he used and that kind of thing. Definitely recommend that. It's by Jeff Watts, The Coach's Casebook. Um, what else? Coactive Coaching is worth reading. Um, what else? Yeah. Let's keep it, keep it at 3 at the moment.

I'm so bad at remembering titles and authors. I mean, and my reading style when it comes to books, it's very 80/20 principle. So I feel like, you know, I'm going to get 80% of results from a book if I read 20% of the book. So I usually just like glance the table of contents. I go through the topics and I choose like one or two. I read that in like an hour, in a couple of mornings, and I just put the book back on the shelf until I find inspiration to check it again. So I never really go through the whole book, so I never remember title or author. So it's quite impressive you're just listing books for— to me as well. So let's say, you know, I'm a CTO ambition, you know, I want to do this, and, uh, you know, I'm working hard, I'm reading books, I'm spending my free time doing coaching and mentoring, you know, I'm going to events, you know, every week or every couple of weeks and maybe once a month. So I'm fully, fully booked, right? And I don't even have time to go to gym. That's, that's where I am. That's gonna lead to burnout, you know, uh, eventually, right? Any, any sort of tips how you personally, having a huge CTO business like CTO Craft, how you manage your own sanity and just keep your burnouts in check?

I think you mentioned the answer just now. It's the Pareto principle, isn't it? The 80/20. Do you find the stuff that makes the biggest impact on the objectives that you have or the reasons that you have for doing what it is you're doing and then being mercenary about the other stuff where you can? But it is hard. It is very hard. I think having a solid non-work life helps, you know, having a family life or having friends or, you know, stuff that happens outside the work sphere that can distract you for a little bit and reground you helps a lot. But radical prioritization, I think, is probably what it comes down to. Yeah.

Yep. What if I cannot shut down my brains? It's just, you know, maybe, you know, maybe I, you know, I got a startup or something like that and, you know, I, I I took a loan, you know, I invested a lot of money and whatnot. And, and I go like, okay, I'm gonna prioritize everything. And, you know, maybe I'm good at this, maybe I'm like, okay, every morning I do these things, but then I do this life thing, you know, I, I spend time with family, but I just, I'm just not present, you know. I'm like, my head is thinking about things and I'm trying to pull from this, but it's just, you you know, it sucks me in and, you know, you're thinking about it, you're still getting that fatigue happening, that mental fatigue. Any, any tips of how you just get that separation done?

It is really hard. It is really hard, you know, especially when you're building, building a business around yourself as an individual, you know, in those fractional and coaching type roles. Um, because essentially you are you're fighting against your ego. Your ego is what is telling you that if you work harder, wake up earlier, always be thinking about the business problems, then suddenly, magically, they'll get fixed. That's your ego telling you to do that stuff. And so you kind of have to have that balance of, right, how much of my ego do I listen to? How much do I let go of? Sometimes it takes therapy. Sometimes it might take mindfulness meditation. Sometimes it might just take having a holiday. But at some point, you have to drill it into yourself that productivity does not mean doing everything at high speed all the time. That's not what productivity is. To be productive means you're optimizing how you use your energy.

I love that. And I'll— for me, what works very well when it comes to this is the morning routine where you, before you kick off your day, you actually sit down and you don't look at the app, uh, you know, your to-do item list, but you actually sit down and you write things you want to achieve today and you think about that, those priorities. I don't know why, but writing things down with your hand It works for me so much better when it comes to connecting with these goals for, for, you know, for today or for that week, compared to, you know, putting things in like to-do app with the keyboard or like Jira or something like that and just looking visually at your prioritization. I don't know, maybe it's just me, but that, that morning routine has helped me a lot because you write things down, it sort of leaves your head, and, and it's just like, you know, just, just becomes easier on your mind.

There was a famous book in the, the 1980s called— I think it was called The Artist's Way, but they, um, they spoke about morning pages, as they put them, where essentially part of, part of their routine was handwriting at least 2 sides of A4 every morning, whether it was garbage or whether it was, you know, stuff about what you had to do that day or a dream you had, whatever it was. And the reason they suggested it, if I'm remembering this correctly, is because it associated the physical action of moving a pen around on paper with stuff like hope for the day and positivity and so on. So it's something about the physical, the muscular kind of movement and that kind of thing, and linking it to your emotions.

Yeah.

So yeah, I can totally believe that handwriting has a bigger effect than typing.

Yeah, I would definitely recommend, and I'm recommending to everybody, but no one listens. Everybody's like, I don't have time, and I type quicker than I write. It's like, so I'm like, okay, maybe it's just me, but it did work well for me to allow that separation of work life and just family time. And if I don't write things down, I, I do tend to keep it in my head and it just comes back, you know, during like dinner and I phase out and I'm thinking about this. But if I write it down, it's just, yeah, it just leaves my head. I don't know exactly what that is, but I would recommend definitely. So if we not able to do that and effectively, you know, we just always on, what would be the first warning signs of a burnout and how people could recognize that they're actually coming very, very close to getting burned out?

I mean, the, the two most common signs are physical exhaustion and like health problems starting to show, and starting to disbelieve in your ability to do the job well. So it's, it's called self-inefficacy. Those two things are usually the most obvious things right at the very beginning. If you can spot those starting to happen, the next stage beyond that is starting to become cynical and starting to believe that it's not worth doing. Those are the main things that I look out for when I'm coaching people who are close to burning out.

Okay, that's a very, very good shout. I can tell you the physical one. So I was doing 5 AM Club for about 9 months. So about like 4 years ago, we were launching a startup. It was like 6 people endeavor. And, you know, I read this 5 AM Club. Oh, that's a title I remember. That's a book, 5 AM Club. So I read this and it was, you know, the notion was you wake up at 5 AM, you know, you do a 60-minute routine. One is, you know, get your body going, it's like a sweat, then you sit down, journal, and then you sit down, read the book for 20 minutes, and then off you do your day. So I did that for about like 9 months, and I developed a heart condition called palpitations, where my heart would just lose a beat. And, you know, I had this one situation where it was quite stressful, and my heart just lost the beat, and I went into this like anxiety attack or something like that. I really got scared because it was just hard to breathe, you know, you're coughing and it's all, you know, around the place. I went to hospital and I started having conversations with the doctors, and they were like, you are— you just like 100% burnout. Just take a holiday for months, you know. And I did, like, I stopped everything, went on holiday, and had like 3 months very low, and it just disappeared. So, so that physical, you know, physical measure of being like very tired, like you should not ignore that. Yes, that was my story, so I definitely can relate to that one. Being cynical or just doubting yourself. So effectively, if we're doing something, it would come out in the form of, I don't believe I can do it, right? Or it doesn't matter what I'm doing, it's just, it's just not gonna go anywhere. You always become, you your own pessimistic voice in your head.

Yeah, that's it. For CTOs who are in companies as a permanent CTO, it's quite common that they'll start becoming cynical about the company and the mission and about the rest of the leadership team and so on, while at the same time just getting worse at their job because they assume they're terrible at their job. Or it starts to become that way. It's kind of a slippery slope.

Can we apply the same rule to others? So if I'm, you know, I have my own, let's say, direct reports and I'm in my one, you know, one-to-one and someone is being very, you know, very cynical in a sense, like, we should not be doing this, it's not gonna work, you know, it's all of this. Can we sort of start thinking maybe that person is just overloaded?

Yeah, 100%. Yeah, big red flag.

Okay, that's a good shout. Um, so we talked a little bit about, you know, strategies, but anything more tactical in the sense of how you, you know, um, manage stress and just, you know, try to prevent burnout? Um, you know, we said about separation, but maybe a routine such as, like, you know, before you go to bed, you know, you meditate, or maybe during lunch you meditate, or maybe you go for a walk, you know, maybe you running every second day, anything, you know, more tactical, how you do it?

I mean, for me, I play music, so I'm a musician and that's my outlet essentially. But I know people who, you know, they exercise, that is their primary way of relieving stress. They'll go for a run every day after lunch or whenever it is. Or they'll spend more time with their kids. Some of them have flexible working hours so they can spend more time with their families. Meditation works for me, doesn't work for everyone. I would recommend at least trying it once. Same with stuff like yoga and healthy eating, all these things. I think they're things you can experiment with, and they're, you know, non-lethal, which means you can try them without there being a, you know, a long-lasting damage if it doesn't work for you. So, you know, why not try it?

Yeah, I mean, I was skeptical about meditation quite strongly. I think I needed to do it like 10 or so times, and my motivation was that I I read enough papers to know that it actually works. So I just try to learn it to a point where it actually gives me benefit. But when you start, it feels like a moot point. It's just like, you know, you don't know how to breathe well. You know, you need to find your music as well. At least I do, you know, guided meditations and or just, you know, just some type of music. And it takes some time to really go to the level where you do it and you actually feel the benefits. So yeah, I like that. Just, just give it a go, see what happens, you know. But potentially it's not for you, but don't, don't give up. Like, it's proven, right? It, it does work. What do you play music-wise, Andy? It's like, uh, my guitar, drums, piano?

Yeah, yeah, I'm a guitarist, um, ukulele, etc., etc., whatever I can get my hands on, really.

Okay, so is that just like a hobby, or do you go for, you know, do gigs Just on weekends?

No, purely an at-home player, just for the, uh, just for the enjoyment of playing, performing.

I have a guitar, I never, I never went to learn it. And I have a piano as well, never learned it as well. I should try this. I will, I will put this in my list as, you know, as you said, give it a go, see what happens.

Exactly. So there you go.

So if we wanna— so we know how to do that, we know how to manage stress, we know how to care about burnouts. If we want to make a culture which cares for the well-being of all employees, any, again, any tips or any signs— not signs, you know, like tactical ways a manager could approach to make sure that that's being put in place for the teams?

Well, the first thing they can do is lead by example. If they are showing themselves to be workaholics and, you know, exhausting themselves and getting snappy with people and cynical, people, then that usually drives that culture down into the rest of the team. They can also make it a point of making it part of their one-to-ones that they focus on wellbeing while they're catching up with their direct reports, you know, and then that in theory cascades down to the people that they're managing as well. And it's about just being explicit about it being top of the agenda.

Okay. I get it. Lead by example. That came up a few, few times with other guests as well. It's always, if you want to be— if you want to see a change, be part of that change. It's a good shout. Anyone in your network, Andy, which you feel would be a good guest for the show?

I'd recommend Emma Hopkins from Spark.

What does Emma Hopkins do?

She is the chief of staff at 101 Ways, which is an agile development company. That she's also one of our coaches and leads some of our mentoring circles.

Okay.

And she also MCs the conferences. So yeah, she'd be great to talk to.

I think I know Emma. Now when you said that she MCs the conferences, I feel like I have a face. Okay. We'll see if we can get Emma. Hopefully we can. Thanks for doing this, Andy. It was great. We touched on some of the important topics. Thanks for sharing your knowledge and thanks for sharing your expertise. Hopefully that was good for you as well.

Absolutely. No, good to talk to you, Mike.

Cheers, Andy.