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

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1 – How would you describe the state of their technology when you joined your organization compared to today?

The purpose of this question is to get a snapshot 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 they discuss the roadmap developed, the challenges faced, and the results 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 to complete it, and track the progress against objectives. Does the candidate understand 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 digestibly. The capacity to focus more on the process, not solely on the outcome, is vital in a leader and a sign of a growth mindset. Did the candidate embrace challenges and feedback, or were they 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 growth opportunities.

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 your plan effectively?
    • What was the end result?

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

    • Engineering teams—size, structure, how were they organized?
    • Culture
    • Roles and responsibilities of team members
    • 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 can 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 required for quick decision-making when things didn’t go as planned. Analytical thinking skills, problem-solving skills, and the ability to communicate how to address challenges are all signs of creativity. Listen for examples of their 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 be able 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 understanding new opportunities available to the business and assessing 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, problem solves, and what they learned in the process.

5 – What were the significant business challenges you faced, and what was your role in solving them?

Sometimes, things do not go as planned. It’s important to assess how the candidate deals with setbacks. This question helps determine work ethic, analytical thinking skills, and the candidate’s drive to produce results. A skilled CTO can articulate a collaborative strategy to achieve the organization’s goals. Listen for the actions taken, 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 who views failure as an opportunity instead of a setback and a person who 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 they use intuition to resolve it quickly and effectively? This question will help you assess the interviewee’s management style and how they’ll engage with others in your organization.

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

The current talent shortage is affecting businesses nationwide, and Gartner predicts the demand for tech talent will outpace supply until at least 2026. If the candidate has successfully hired and retained great talent, it’s a sign that their 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 focused on upskilling current employees and utilizing technological innovation to automate manual processes.

Related blog from Aleron Group partner Acara Solutions: The Tech Talent War of 2023


The role of CTO has evolved into a multifaceted, forward-thinking, and dynamic position. During the interview, it’s essential to ask questions that help you assess the candidate’s ability to take your organization to the next level. The decisions made by the 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 successful CTO knows how to use technology to impact the business meaningfully and is always searching for the next advancement to create greater value and increase profit.

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