Health Lyrics on Hiring
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The One-Question Interview for Your Next Chief Technology Officer (CTO)

There’s no doubt: the role of Chief Technology Officer (CTO) must be filled with the absolute best candidate available. The success of any IT organization is dependent on this position, and they must have the trust and backing of the Chief Information Officer (CIO). While ensuring you find the right person to hire can be incredibly tricky, there’s actually one interview question that can set all of your candidates apart.

Before we get there, though, let me set the background for our story.

My team had a really tough time finding the right Chief Technology Officer candidate. The primary reason for this struggle was because they were replacing me. When I came into the role of the CIO, I had been a consultant for the better part of 20 years and had many technical certifications. I had worked in and with some great companies on some really cool projects. (The benefit of being a consultant is the broad base of experience you are fortunate to receive; the downside is the travel.)

The problem, of course, was that I was hired to be the CIO… not the CTO. The more I operated as the CTO, the less I did the job of the CIO. So, we decided that it was time for a change and started the process of filling the actual CTO role.

The team went through the normal channels and lined up three potential candidates. We didn’t use retained search for this position, although I would highly recommend it. Great CTOs aren’t surfing Indeed. The best approach for finding the perfect candidate is to use your own, established network, if you are so inclined.

As a general guideline, we are always looking for five qualities: Competence, Cultural Fit, Customer-Focused, Character, and Chemistry. The five C’s.

My team had already done the preliminary interview and were all agreed that we had a candidate that could do the job. We scheduled a 90-minute final interview with each one, which I would attend and conduct with the team.

The CTO Interview

The best way to interview a candidate would be to go to their current place of employment and watch them do their job for a week. As my friend Eric Herrenkohl, author of How to Hire A-Players, is fond of saying, “Past performance is the best indicator of future results.”

Think about how powerful this would be. You could evaluate the five C’s very easily with this kind of access. Of course, since that isn’t an option, I wanted to devise a way to create the same environment in 90 minutes.

For our particular interview, we arranged to have a room with several very large whiteboards.  We asked several of our subject matter experts to join the meeting, since the CTO would have to work closely with each of these people in the future. We had five dry erase markers sitting in front of the spot where the CTO would sit down. Then, we brought each candidate into the room for their interview.

The Question

The minute a potential candidate enters the room, you begin to observe. Do they greet everyone? How do they engage? Do they develop a rapport?

Once everyone is situated, I give them a little background on the company and the role. Then, I finally ask the question.

I’d like for you to map out our journey to the cloud for our infrastructure from our existing environment. You can ask any questions you’d like from the subject matter experts you have here in the room.

A great CTO will get excited. He or she will see this as the easiest one-question test they’ve ever been given. To start, they will ask a few clarifying questions on the task and then they will get to work.

They will ask the subject matter experts to give them some basic background. They may start to draw on a piece of paper or they may just go to the whiteboard. Naturally, they will engage people and they should inspire greater thinking in the group.  You won’t get a plan to move to the cloud in 90 minutes, but you should be able to determine how this person fits with the team.

I’m always looking for a few specific things while the interview is going on. How do they engage with the team? Do they talk “at” the team or are they bringing them along? Do they talk down to the team at any point?

Is the session a discussion between colleagues, or is it a lecture from the superior intellect? Is the solution done from a consumer perspective? Do they ask qualifying questions around the needs of the users?

A non-CTO will not know where to start. The clarifying questions on the assignment will never end. They will easily remind you of the serious limitations of their perspective. They may never engage with the team because they are too busy trying to figure out how to get back to a more traditional interview, where they are comfortable walking you through their resume.

Much of their resume, of course, is the experience of a previous team. Not necessarily this person.

When the interview is complete, I ask my team to leave so I can get a few minutes alone with the candidate. I can be accused of playing gotcha here, but I know of no other way to get a glimpse into someone’s character.

Once we are alone, I get them comfortable and ask them what they think of my team. On more than one occasion, people have trashed one or more of my team members. This should tell you everything you need to know.

Beyond the CTO

This method works for other roles. For example, if I were hiring a support technician, I might put a series of exercises in front of them that require them to visit people’s offices and conduct one or two tasks.

For example, you would hand them five call sheets with two to three tasks they have to conduct on each computer. They then have to go to each cube or office and do the work. The five people would be a part of the interview, of course.

The candidate would walk down the hall, find the office, and have to gain access to the room and computer and complete these tasks. You would find out if they had manners, if they can perform some tasks on different computers, and if they interacted with the staff in a way that said we want them to be a part of our organization.

The process isn’t perfect. However, I have found that there is no better way to identify the best candidate than to watch someone actually do the job. This method hasn’t let me down yet.

Hope this helps. Please follow me on Twitter @ThePatientsCIO or connect with me on LinkedIn.  If you wish to discuss all of this further, please reach out. Thanks for reading.