5 Tips for Current and Aspiring CTOs

For many technologists, the career goal is CTO. This role is different from any other you may hold on your way up the hierarchy. This can seem daunting to some as it may not be obvious how you can acquire the skills you’ll need to succeed.

Below are some of my top tips on what it takes to become a CTO, as well as the lessons I have learned along the way.

#1. Stand Out Early in Your Career by Selecting an Area of Expertise

When you start a career, especially in technical roles such as software engineering, it can feel like there are no ways to differentiate yourself. Some people make the mistake of jumping between roles very quickly to try and "broaden" themselves or make quick salary jumps.

This can work for a while, but I’ve seen a lot of people whose careers have reached a plateau surprisingly quickly, and they wonder why. One reason is that a surprising number of careers do require a true depth of experience and expertise to progress past a certain point. 

An effective career tactic I’ve seen in technical roles is, instead, to go super-deep early on. Become the expert in the feature you work on. Learn everything about it, how it relates to other parts of the product, and why it works the way it does. Before long, people will realize you know more about it than anybody else in the firm, even though you might be ridiculously junior. You’ll invariably start getting invited to meetings where that component is discussed or where clients are briefed.

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#2. Nobody Is Impressed by Jargon

CTOs spend as much, if not more, time with non-engineers as they do with other engineers. This means you’re often the most technically deep person in most meetings you attend. You will not be invited back unless you can communicate complex information in a way that these audiences can understand!

If your audience is confused, you have failed, not them. The good news is that this is a fixable problem. This is because an inability to explain something is extremely often a sign that you don’t fully understand the topic yourself. So, take the opportunity to deepen your knowledge and practice explaining it to others. You’ll be amazed at how much you learn in the process of trying to teach something to somebody else.

#3. The Dunning-Kruger Effect Is Real

The more senior or experienced you get, the more failures and troubled projects you’ll have worked on, so you’ll almost certainly become more cautious with age. This is something you should remember when faced with ‘too good to be true’ internal proposals or external competitive threats. 

Is the ambitious claim plausible? Or does the person saying it simply not realize that they don’t know what they don’t know? Take time to help others on the management team, or your sponsor in a client, to understand this phenomenon.

Many bad decisions flow from mistakenly comparing a "flawed but realistic, presented cautiously" proposal with one that is "amazing but theoretical and presented with utmost confidence."

#4. Structured Thought Is Not as Common as You Might Think

Do you ever find yourself in a meeting laying out an argument in the style of a mathematical proof, where each step follows logically from the previous, and you don’t rely on a fact you haven’t first established? This is not normal!

Despite this, it is a superpower to be cultivated. And the good news is it often comes extremely naturally to many technologists, especially if your background is in mathematics or the mathematical sciences. You should look to encourage those you mentor to develop the same skills and be gentle with those who have not yet mastered them.

#5. ‘Technical’ Doesn’t Just Mean ‘Technology’

Throughout my career, I have dedicated hours upon hours to my independent research around the nature of banking, what money really is, as well as payment systems, and so forth. And it all began because I became fed up with feeling confused in meetings with people who worked for banks.

At first, I just assumed it was because they were all super-expert and experienced, and I was ‘just’ a techie. But I eventually realized that they didn’t understand it either! It was almost as if there was a conspiracy of silence, and everybody just used complicated-sounding words without truly understanding the topic themselves. Once I had figured some of this stuff out for myself, my confidence grew, and I found myself being called upon for more interesting engagements.

At R3, we work with a lot of complicated financial institutions – an insane career gift. I encourage our technical teams to take the time to learn what they do and, perhaps more importantly, why they exist. Especially the financial market infrastructure firms. What is the fundamental problem they exist to solve? What would the world look like without them? The core concepts of clearing, custody, payments, and so forth are surprisingly interesting and rest on a small number of very precise concepts. Technologists, in my experience, and if they take the time to do it, are unusually good at getting their heads around these things if they choose to.

Parting Thoughts

Being a CTO is not easy. You are fluent in technology, and now you must be as fluent in the business side of things as well as learning how to manage a larger team. Regardless, this position is incredibly rewarding. When done right, you have the power to bring great value to your company and nurture the technologists of the future.