5 things to watch for when hiring a CTO

A CTO is one of the most important persons when it comes to induce innovation. The why is simple. This is a person that will be involved on a high level and is expected to get others engaged. It’s true that people don’t leave companies, they leave managers. In fact, a recent MBA Thesis that I wrote concludes exactly this. The manager is the single most important person for the employees.

A CTO is a form of “new development IT director” (for a further explanation, read about the difference between the CIO and the CTO here). It’s by all means crucial for the company, that decides to break new ground and invest in the digital future. Massive internal expectations, the future of a completely new product and many times the company – makes it even more important to get the right person on board.

  1. Check their managerial skills

    As the person is indeed very important when it comes to motivation and engagement, as explained above – it’s a good idea to check how well they manage others. There are several ways to do this. You can talk to members of the former team and ask. This can sometimes be a bit weird but could do it. But there is one thing that is very easy to do, and it will in most cases give you the answer right away:
    Simply ask them this question:
    – “If you were to describe the least performing colleague of your team, what would you say”?
    If the CTO candidate explains the person as “lazy, slow and stupid” – or somewhere in that direction, you know who you are dealing with. You are potentially dealing with a task driven and result-oriented person. Sounds great? Not so fast. Who do you want as a CTO? Do you want someone who just implements and gets stuff done, running like a train and “hits the ground running”? To be honest, this doesn’t work. Not if you want someone who you want to lead people. What you want is a relationship-oriented leader who involves others to get stuff done, and are able to engage teams.
    A person who is result-oriented would respond to the question more in the lines of: “it was a good person but they were not in the right place” or “the person weren’t able to catch up with others but we had a good contact”.
    Here is a Wikipedia link for more information on different leadership styles.

  2. Portfolio, portfolio

    What have the person done before? Sounds trivial, but it should go beyond the usual CV-list. What role did they have in the project they list? What were their challenges? How did they overcome them? Questions like this gives you a better understanding of how the person was able to perform in different situations in the past. Portfolio is number 2 on the list for a reason. Never hire a CTO without a  track-reckord. You want to be risk averse here. Why? Why not? Your future CTO should have been involved in many different projects, not only a certain type, and should have been able to draw conclusions from their experiences. This is what you get.

    Never hire a CTO without a track-reckord

  3. Communication

    A nice one. Of course the person should be able to communicate. It would be very hard for a person in a leading person to communicate if they didn’t. But are they able to communicate in a way that shows the participant of the conversation that they are listening, that they understand and that they have questions. Or concerns?

    I recommend the communication style to be active. This means that it’s not about listening to a monologue, it’s about creating an experience by engaging in a discussion in a dialogue. A CTO should be able to challenge and develop things out from conversations. You can look for behaviours like if they are just running away in the discussion without no goal (signs of stress caused by nervosity).

    One other misconception to look out for: “Technical persons”/developers sometimes have a rumour to be silent and introvert. There are even posts online about that “introvert is the new cool“. Don’t fool yourself to generalize. All people are different. It’s much more important to find a match for your company culture than to think that all “IT-people” should be introverts (or vice versa in marketing). Which leads us to number 4 on the list.

  4. Personality style and corporate fit

    Do you have a buzzing super cool startup environment with that mandatory ping pong table and table football? Free coffee handmade by a in-house barista? Maybe your CTO should be more of a creative one. Matching the personality style with the the corporate culture is crucial for a long-term success in recruitment. In the beginning, everyone is “drinking the kool-aid” and are easily persuaded by the nice coffee and the cool atmosphere. Focus on the months after that. In what environment are you dropping the CTO? Is it a “here you go, the keys to the kingdom – do what you want” or is it more of “well, this is how we do things around here”-kind of environment? Find out what environment is the best for the CTO candidate. Not everyone wants to create new things from scratch. Many wants to come to a pre-defined structure, but one that enables to implement new things, without so much “politics”. You see where this is going. Everyone is different. In order to secure your investment, make sure you hire a CTO that is the right fit. How? Test them. The Jung personality test can help you understand the person better. And they can fill it out themselves before the interview. And it’s not about to find out if the person is good or bad. It’s about finding out if they are a match for the position.

  5. Technical skills

    Why is this one last? Because technical skills can be learned. You should check the portfolio and understand if the person has experience leading technical projects. Then you already ticked this one off. It’s also a good thing if the CTO candidate is interested and wants to learn new things. In fact this covers all future employees, the will to learn new things and develop is a great skill to have around in organizations. But of course. The basics must be there. Number 1-4 of the 5 to watch for when hiring a CTO is about leadership and how your new leader is a match for your organization. Number 5 is, even though some personalities may be more eager to learn new things, still down to the basics. If your organization has a special technical environment based on .Net, Java, PHP, Python etc it’s of course a basic requirement that the CTO candidate knows them. I would like to stress that they don’t have to be experts, it could actually be beneficial if they aren’t, and instead can delegate that to a technical lead (depending on the organization size). However – if the person has 15 years experience with the Microsoft .Net platform, and your entire IT-application landscape is built in Java – expect the person to feel more comfortable in .Net. Which also means they may want to change your organizations technical direction. And hey, they are the future CTO, so they should be able to take that decision, right? Just be aware that the person you choose will have a huge impact on the technological (aka digital) development (aka transformation) of your organization. And a last one. Avoid asking for a “Full-stack CTO”. It’s not applicable. As “Full-stack” means they should be able to do everything from photoshop to database, is this really the person you want? It’s enough that they know it exists and what it’s used for.

Even though the 5 things to watch for are up now – I have a last one. See it as a bonus. Make sure that your CTO put the business first. Everything you want to develop must have, at least the possibility to, get new business. Forget all the technical terms and nice database structures. If you don’t have the customers – you don’t have the business. A CTO that understands this is golden.