My Tech Exec Interview Checklist

Published in

Nerd For Tech

3 min readMay 17, 2022

While the vast majority of my work nowadays is advisory work for CTOs and CEOs, I sometimes help companies bring in a new tech executive. This week, I thought it might be interesting to share what are the things that I look for when I participate in these interviews. Even if you’re not looking for another job right now, seeing which traits I believe set executives for success might help you spot personal areas for growth.

Before I start listing them, I want to note that you can see there are a lot of things here. That means more than one interview is needed, or I might ask others for their insight around this.

Tech Proficiency

Clearly, tech executives need some connection to technology. How hands-on they ought to be varies greatly from one company to the next. Getting the right hire to kick off a startup is not the same as finding a replacement VP of Engineering to take charge of a large existing team.

So, depending on the company’s needs, I might go deeper with technical questions or focus on higher-level thinking.

LEAP Responsibilities

In The Tech Executive Operating System, I listed four general responsibility areas for tech executives: leadership, evangelism, architecture and innovation, and people and processes. Depending on the intended role, I will look for specific areas of knowledge and experience. For example, for an innovation role (a more CTO role), I might brainstorm ideas whereas, for a People and Processes role (say, VP Engineering), I might want to hear their take about running teams, their hiring mechanisms, and similar.

Business Speak

This isn’t usually answered with a specific question, but something I try to observe when the candidate speaks to the CEO or other non-technical people. For an executive to move upstream effectively, he or she will have to be able to converse with peers openly. The skill of explaining decisions and tradeoffs in a way that allows others to understand and collaborate is vital. Too many tech executives abuse this language barrier, even if unknowingly, by pushing for certain decisions where others cannot object.

Growth Mindsets

I’ve written about the importance of hiring for growth mindsets, and with executives, that’s all that more important. How do they describe past obstacles? How do they react to moonshots that the company might be considering?

Positivity and the Executive Mindset

The above also connects to their ability to drive others with positivity and inject energy into day-to-day efforts. The executive mindset is a prerequisite for anyone leading teams. That means that they default to the “it’s possible” camp and help their team turn the impossible into reality.

Passion and Agency

A big part of starting a new role is having jitters about what’s possible. I love it when candidates mention possible ideas and changes. That’s an essential part of an executive’s role. I want to see that they have the agency to suggest these ideas or ask the right questions. Someone that expects to start a position and be told what to do is more of a glorified manager. It’s a good sign when they realize that they have permission to take the lead from the get-go.

Candor

Lastly, no one wants a yes-person (or, at least, I never agree to help look for one). I see it as a great sign when candidates ask prodding questions or even say they disagree with something. Coupled with business-speak, it is a force multiplier for tech executives. Nevertheless, I understand that this is very hard for some candidates, and if I don’t see it in interviews, I will explicitly give them permission to speak up.