A C-suite interview has a much different dynamic than a standard mid-level management interview. The stakes are higher because the candidate being interviewed will be a major decision-maker and this person must share the hiring organization’s goals and vision. A CTO should possess the business knowledge necessary to align technology-related decisions with the organization’s goals. Therefore, the interviewer will need to ask probing questions that require the executive candidate to reflect on the past, focus on the present, and envision the future to demonstrate his or her level of competency, skills, and passion. The interview is also the opportune time to assess leadership skills, communication style, and conflict resolution ability. To help find a good fit, we have compiled a list of interview questions targeted specifically to a CTO position. 

1. When you joined your current organization, how would you describe the state of their technology and the overall organization when you joined?

The purpose of this question is to get a snapshot of the state of the interviewee’s current organization and technology before the candidate implemented changes. This question provides a starting point for the candidate to build upon as he or she talks through the roadmap developed, the challenges faced, and the end result achieved.  

2. Did you develop a roadmap or visualization of a strategic plan?

This question will help you assess whether the candidate can visualize and communicate a strategic plan, create a timeline in which to complete it, and track the progress against objectives. Does the candidate display an understanding of the best practices for workplace planning— including the technology and the cost implications? Listen for signs of critical thinking, inductive reasoning, and the ability to communicate complex topics understandably. The capacity to focus more on the process rather than just the outcome is important in a leader and is a sign of a growth mindset. Did the candidate embrace challenges and feedback or was he or she focused only on the result? Did the candidate welcome new and innovative ideas to unlock change in developing a roadmap? Fixed-mindset leaders view challenges as failures and wasted effort instead of as opportunities for growth.  

Additional probing questions to ask on this topic:

  • How did you make your initial assessments?
  • What was your overall goal and how was that tied into scalability and revenue growth?
  • What challenges did you face and how did you overcome them or adapt your plan?
  • Did you execute it? What were some of those challenges and how did you overcome them?
  • What was the end result?

3. Tell me about your current organization as far as what you walked into, and the changes that you made, concerning:

  • Engineering teams – size, structure, how were they organized?
  • Culture
  • Methodology – agile?
  • Infrastructure
  • Digital transformation
  • Business functions – were they technology-driven?
  • Customer experience

Organizations rarely expect a new CTO to maintain the status quo. By asking this question, you’re trying to determine if the candidate has a solid technical background and the ability to translate strategies into tactical technological solutions. Transformation revolves around a fundamental culture change—of innovation and continuous improvement—at the organizational and process level. Did the candidate recognize opportunities and drive the changes necessary to achieve better results? Listen for signs of creativity which is required for quick decision-making when things don’t go exactly as planned. Analytical thinking skills, problem-solving skills, and the ability to communicate how to solve a problem are all signs of creativity. Listen for examples of his or her ability to inspire, keep employees engaged, and show empathy while still acting strategically.

4. What were some of your biggest technology challenges? 

Change is inevitable in business and a C-suite leader must have the ability to adjust and keep moving forward. With this question, you are listening for the candidate’s ability to adapt to the ever-changing technology landscape. A real differentiator for CTOs is the ability to understand new opportunities available to the business and assess whether the technology creates value for the organization. Can the candidate quickly solve problems with the proper application of technology? This question will also help you gain insight into how the candidate thinks and problem-solves and what he or she learned in the process.

5. What were the major business challenges and what was your role in solving them?

Sometimes things will not go as planned. It’s important to assess how the candidate deals with setbacks.This question helps assess work ethic, analytical thinking skills, and the candidate’s drive to produce results.A skilled CTO will be able to articulate a collaborative strategy to achieve the organization’s goals. Listen for the actions taken and the thought processes and reasoning behind each action. How did the candidate engage key stakeholders and get their support and buy-in? Look for a leader that views failure as an opportunity instead of a setback and a person that keeps going despite obstacles.

6. What was a major people management challenge?

Conflict is inevitable—it’s how it’s managed that matters. Did the candidate take a hands-off approach and let the problem resolve itself or did he or she use intuition to resolve it quickly and effectively? This question will help you assess the interviewee’s management style.

7. How were you able to hire and retain great talent in such a competitive environment?

The current talent shortage is affecting businesses across the country. If the candidate has successfully been able to hire and retain great talent, then it’s a sign that his or her organization has a good culture and employer brand. Does the interviewee place a strong value on retention? If the candidate does not see retention as an issue in today’s talent market, it’s a red flag. Listen for a response that’s focused on upskilling current employees and the utilization of technological innovation to automate manual processes.


During the interview, it’s important to ask questions that help you access the candidate’s ability to take your organization to the next level. The decisions made by Chief Technology Officer will shape the path and trajectory of the technical performance of your organization and drive it to higher levels of efficiency. A great CTO knows how to use technology to impact the business in a meaningful way and is always searching for the next advancement to create greater value and increase profit.

This blog was written by TalentRise Practice Leader, Executive Search Pete Petrella.