15 Essential Interview Questions for CTO Candidates

Chief Technology Officer

As an executive search firm, we help place CTO’s at nonprofit organizations and social enterprises. The recruiters here at Y Scouts try to understand a number of things when interviewing a chief technology officer candidate – their purpose, values, career history, the high-impact success outcomes and achievements a CTO has had in their career – and a lot more. (Note: if you’re looking to hire a CTO, contact us and we’d be happy to share our recruiting process with you)

But what other CTO interview questions do leaders ask their candidates? We asked the Y Scouts Leadership Community what their favorite CTO interview question was and why they like to ask it. Here’s what they had to say:

1. How do you measure your success?

Everyone has a different idea of what it means to be successful. If the candidate’s vision of success is similar to ours, we’ll all feel satisfied when a project is finished.

2. What brought you here?

Anyone can hand me a resume and let me read about their career history. I’m looking for someone who can explain how their past experience led them to their current career path.

3. Pitch what we do.

Every executive employee should be able to represent the business in public. If the candidate can create a sales pitch for your company during the interview, you’ll find out if they can handle speaking on your company’s behalf.

4. What is one thing you would want to change about the company right now?

This question shows me how much the candidate has thought about my business and how much research they did before the interview. I’m looking for a thoughtful answer, not just something they think I want to hear.

5. What are five words you would use to describe your personality?

I like this question because it lets me see who the candidate is. If they struggle to come up with enough words, or they come up with too many, it speaks volumes about who they are as a person. Likewise, the words they pick give me an idea of which personal qualities they look for in others.

6. What is was your production measurement in your last job?

This is a really easy question that tells me how critically they think about their work.

7. Tell us 3 thinks you like and 3 things you dislike about your current job.

This question tells me a lot about someone’s work persona. If they only have bad things to say about their current position, or if their dislikes seem trivial, it could be a problem. I need to be sure they’ll fit in with the company’s culture.

8. Tell me about a time where you identified a serious problem in the workplace and came up with a solution that benefitted your company.

Problem solving skills are essential for a CFO. I want to make sure the person I hire has proven their ability to diagnose and fix technical problems. I can use their answer to get a better idea of what they do in tough situations and if it will work in my office.

9. How have you used new technology to help your employer?

Technology is rapidly advancing. I need to make sure my chief technology officer follows new innovations and isn’t afraid to try them out. If they have been able to successful use new ideas in the past, it makes me confident that they will be able to do the same in my organization.

10. What books and blogs are you currently reading?

What someone reads can tell you a lot about what they enjoy and what they aspire to become.

11. Ask questions to determine cultural fit.

It’s not enough to hire someone talented; they have to fit in with the company’s culture, too. It’s important ask questions that reflect the company’s culture and purpose. That way, I can tell if a candidate shares the same goals as the company.

12. How do you use communication skills?

Someone in a leadership position needs to be able to communicate with employees on all levels of the organization. This is critical for a CTO.

13. What is the most complicated assignment you have done?

This question gives the candidate a chance to show me how they rise to meet challenges. I’m also looking to see how they solve problems: do they break them down or tackle them all at once?

14. Tell me what we do in your own words.

How easily a candidate can sum up the company’s purpose and impact shows me how much they already know about the organization. The best candidates we’ve hired have done research on our company, our goals, and our impact and gave this question a thoughtful answer during their interview.

15. Teach me something I don’t already know.

One of my friends says Google executives ask this question a lot during interviews. It makes the candidate think on their feet and give a unusual, creative answer.

You might be interested in these other posts about hiring a CTO:
When to Hire a CTO
What to Look For in a CTO
How to Hire a CTO
What to Pay a CTO

What CTO interview questions have you been asked? Let us know in the comments.

Y Scouts is an executive search firm that helps nonprofits and social enterprises find exceptional leaders. Contact us if you are looking to find an exceptional leader. To be considered for exceptional leadership opportunities with our clients, please take the first step by joining the Y Scouts Leadership Community.