Interview Questions and Simulations for CTO Candidates

Note: This sample assumes that the CTO is responsible for all six areas listed in our Finding a Chief Talent Officer article. You should tailor them based on your how you have scoped the CTO role.

Sample Interview Questions

  1. Thinking about all of the different roles you’ve led searches for, can you tell us about one that was particularly tricky to fill? Why? What did you do?
  2. We have recently made several senior-level hires. We had good outcomes, but the process took a lot out of several of our senior people—especially our ED. What are some ideas you have or might have seen that can help streamline the amount of senior time spent on hiring while not compromising on quality of hires?
  3. Can you tell us about a time that you disagreed with another interviewer coming out of an interview—either where you hired someone despite another interviewer disagreeing, or where you felt strongly that you shouldn’t hire someone that another person thought should be hired? What was the situation? What did you see in the interview that they didn’t see? How did it work out?
  4. Can you tell us about your experience managing staff? What size teams have you managed?
  5. Tell us about a time when you had to get buy-in on a decision from a large group of stakeholders. How did you go about it? What worked and what didn’t?
  6. Have you had experience crafting a plan of action to make a vision come alive? It could be for a team, a client, a campaign, etc. We are interested in hearing about your experience of how you went from a broad vision to strategy.
  7. What have you seen organizations do (either places you’ve worked at or had a chance to observe closely) to improve diversity, equity, and inclusion? We are eager to hear what worked and what didn’t.
  8. What do you see as your own areas of personal growth in terms of equity and inclusion? What’s something you’re working on learning?
  9. Can you tell us about a time you realized that something you were doing as a manager had unintended negative consequences from an equity lens?
  10. Can you tell us about your experience managing a project? Tell us what the project was about and your role. What went well, what would you do differently?

Sample Exercises and Simulations

  1. Here’s our job description for X role. Could you take a look and give us some recommendations on how to improve it?
  2. Here’s an open position we have. Could you give us some suggestions on how to build the pool for this position? What are some typical and not-so-typical places to source candidates from?
  3. A manager has come to you with a problem—they have an underperforming employee. The manager is concerned about how to talk to the staff member given they have different racial identities. What questions would you ask the manager? How would you advise them?
  4. A high-performing employee has announced their intention to quit. Their manager has sought your help in trying to retain them. How would you go through the process with the manager to decide what we can do to retain the employee?
  5. Here are three resumes of people who have applied for x position (with names and other identifying details blocked out). Here’s the job description for the position. How would you rank order the applicants and why? We are interested in your thought process.
  6. We have a candidate coming in for a second-round interview next week. Could you join us for the interview? This means, we will prep together and debrief after the interview is over.
  7. Here’s a sample performance evaluation a relatively new manager has written for a staff member (with all identifying information redacted). What pointers could you offer the manager on how they could improve the written evaluation? How would you coach them on how to deliver the review?
  8. Let’s say we recently did a survey of all our staff asking about their satisfaction with their jobs. The data showed a 20% decrease in overall satisfaction rates. The executive team has asked you to come up with next steps—can you outline a process you will go through to get to the bottom of this? What questions would you ask?