CTO Craft, which was founded in 2017, is a professional development community for CTOs, vice-presidents and technical bosses, including events and mentoring groups.
The idea for CTO Craft came from founder Andy Skipper’s own experience of coming in as a trouble-shooter for companies that had a bad experience after overpromoting a colleague to a CTO role internally.
‘The first people you are responsible to are people on the same level as you across the organisation and not those developers underneath you’
A common pattern, says Skipper, who was previously CTO at Comic Relief and Made.com, is that a very good technical person – a developer, say -is promoted to CTO without any guidance or support. And predictably there is fallout when that all goes wrong, whether it’s in damaged relationships or project overspend.
Skipper saw an opportunity to prevent this situation from spiralling by getting in early and supporting the would-be CTO to develop their own skillset.
Today, CTO Craft has grown from about 150 people around London sharing their experiences to a worldwide group of 9,000 tech leaders supporting each other, whether that’s through one-on-one coaching or a mentoring circle.
Genius coders don’t necessarily make great managers. It’s a completely different skill-set, isn’t it?
Smaller start-ups especially will not have an evolved career progression framework or even an HR department. Most people don’t even make a conscious decision as to whether they want to become a CTO. It’s thrust upon them. People who are very good technologists, very scientifically minded, end up taking on management responsibilities which don’t fit. However, that doesn’t mean they cannot evolve into a CTO, which is where coaching and peer networking comes in.
A lot of our early work was almost like couples therapy where we had to talk through the relationship meltdown between the CTO and the founder. We were there almost as a mediator.
That said, if you’re lucky and if you’re in the right organisation, you get to the point where you can make a decision as to whether to go down the management route or the individual contribution route.
What does the perfect CTO look like?
It depends on the stage of the company. There’s a huge gulf between being CTO of a two-person start-up with an idea that’s pre- pre-market and the CTO of a 1,500-strong software company. It’s where you are in the company lifecycle. The trend though is away from technical expertise towards what’s called soft skills.
If you’re in the right kind of organisation, there is a natural point at which you can decide to be a manager over being an individual contributor. The route to becoming a technical CTO is fairly clear from joining as a junior developer, then a senior, then potentially even a principal or a staff engineer.
The tricky bit comes when you get assigned management and leadership responsibilities, without the support needed. In those cases, I think it’s about going out and self-educating. If you’re in a company that does have training, peer support and coaching, then it’s much easier. For those who don’t have that, that’s where places like CTO Craft come in, where you can get peer calibration and see what other people are doing in those situations.
Let’s talk about the self-educating part. What can you do to prepare yourself for a CTO management role?
The easiest way into a management and leadership role is to become an engineering manager before you become a CTO. Assuming you have that engineering manager role in your company, there are a whole bunch of great books on engineering management, such as The Pragmatic Programmer by David Thomas and Andrew Hunt. Another good one is Accelerate, which show you how to measure software delivery performance. A good general technical management book is The Manager’s Path by Camille Fournier, while The Five Dysfunctions of a Team by Patrick Lencioni is very good talking about psychological safety and intra relations within a team.
How early in your career should you specialise in say, DevOps or cybersecurity?
Some people will just know what they’re most naturally drawn to. Certainly, some people that I’ve worked with have been very suited to DevOps or want to get into cybersecurity. I think you should aim to try and get exposure to as many different parts of the tech world as possible in your early career. That said, if you feel natural affinity for, say, functional programming, then go and get a functional programming job in Scala.
Are there any tech sectors or skills that are really hot right now? That specialising in will help accelerate your career?
Basically, you can extrapolate it from the types of roles which are hardest to fill. There are things like front-end development stuff and there are a lot of companies looking for people front-end frameworks, such as React and Vue, at the moment.
Anything that demonstrates you have some problem solving and critical thinking ability will do you a lot of favours. Anything around data science and analysis or project definition can be incredibly helpful. Systems thinking, developing awareness of how your work fits into the bigger picture, is useful.
As you develop in your career as a tech leader, what part do soft skills play? Are they becoming more important?
Possibly soft skills have been neglected in the past. Nobody should be trying to take on a management or leadership position without any understanding of what it means to deal with people and motivate them.
Empathy, communication and creating an environment of psychological safety so that people can really push the boundaries of what they work on without fear of reprisal, are really important in a management role. Companies such as Google and Twitter have analysed what works best in their teams and they’ve been fairly unanimous that generative cultures, as opposed to dictatorships and bureaucratic cultures, are the way businesses work best. It’s as simple as that.
Another skill is knowing how to translate the technical speak to people outside of engineering. Actually, the first people you are responsible to are people on the same level as you across the organisation and not those developers underneath you. Part of that responsibility is translation, being able to translate the needs and plans and solutions which the engineering team has come up with to other departments.
Has the role of the CTO and the skills needed changed since the working from home revolution?
Absolutely. Working from home has introduced a whole bunch on new barriers. You don’t get to form the same interpersonal relationships as you used to have with team members, the same level of integration. And then you have to use new tools, new ways of working with your team, so that you have to write everything down. So, yes, it’s been a big, big change.
When people come to you, what’s the biggest problem they are grappling with? Is it keeping up with the tech side or feeling overwhelmed by the personnel management and soft skills part?
I would say that, coming out of the pandemic, there has been a lot of burn-out. Some people come to us because they want to measure themselves against other people’s approaches. Sometimes they want hands-on coaching and mentoring.
The final level in CTO career development surely has to be sitting on the board
It’s far less uncommon than you think, to use a double negative. If you’re a tech start-up and you’re one of the co-founders, then as CTO, you’re going to be on the board anyway. But if you are a tech-first, as opposed to a tech-enabled company, regardless of size, I think you should have someone technical on the board.
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