How to prepare for a CIO job interview, with these 50 questions for CIOs

Hiring any senior executive is an expensive investment. The quality of interview questions is critical to ensuring reliable and valid interview results. It is also important to ensure all interviewers follow a consistent process, and use the interview guide in the same manner for each interview. Thus, individual assessments can be evaluated fairly and accurately to form an agreement among the interviewers afterward.

This article provides a series of questions that help members of the executive hiring team (CEO, CFO, COO, HR leaders and other senior executives) to develop a comprehensive interview guide for assessing the qualifications of CIO candidates. The questions are grouped into the following categories:

General background about the candidate

Strategic planning, operations and financial management

Industry and business knowledge

Use these questions as a starting point to develop the interview guide for the CIO role in your organisation. Identify the ones that are most relevant to your enterprise mission and strategic goals. Modify the questions to fit your business context as needed. Develop new questions to assess areas not covered in this document, by following the format and structure of sample questions presented in this document.

Interview Questions

General Background About the Candidate

The questions below help interviewers get to know the candidate by gathering the candidate’s views on the CIO role and the needed qualifications to succeed in your organisation. Interviewers can also use these questions to understand the candidate’s career aspirations and interest in the role. The questions will clarify what is drawing them to the industry, your organisation and this position – and how these values and motivators will support the advancement or attainment of your business goals and objectives:

What specific background and experience do you bring that will help our business to achieve its goals?

For any gaps you may have in terms of qualifications, capabilities or experience, how would you bridge them? For example, if you lack infrastructure and operations (I&O) experience, how would you address that, and why do you think you are a viable candidate?

The role of the CIO is evolving. What are the key capabilities and experience that a strong CIO needs today, and how do you foresee that evolving over the next five to 10 years? What areas need to evolve to stay relevant?

If there are no restrictions on where “digital initiatives” should be led in the enterprise, where should they be led and why? If the digital initiative is outside of IT, what should your role be?

What do you attribute your success in the IT field to? How has your success in IT impacted or moved forward enterprise digital goals in the past?

How do you balance the necessity of being technically current and still being business-focused? How do you see the allocation of your time spent?

What do you consider your core values? What type of culture do you thrive in?

When you leave your current employer, what do you suppose will be your legacy?

How do you participate in industry leadership (for example, industry and trade organisations, presentations, social media, and blogs), and how does that help you in your role? What value has it brought to your success?

Strategic Planning, Operations and Financial Management

A core challenge for any executive is balancing long-term versus short-term planning and execution. Many executives are strong in strategic vision, but have difficulty gaining support in accomplishing that vision. The following questions focus on the candidate’s experience and ability to set long-term goals, while managing the complex task of gaining cooperation to actually accomplish those goals.

This question set also assesses the candidate’s ability to adjust and course-correct as needed to ensure success. Interviewers should look for strong examples of success, where the candidate has delivered clear business outcomes, and evidence of the candidate’s adaptability. The set also includes questions to assess the candidate’s ability to view the IT budget as a portfolio of assets, and to manage it in a manner consistent with the risk profile and strategic approach of the interviewing organisation:

How do you engage and gain agreement and cooperation from a diverse set of stakeholders? Provide an example of when you did this successfully.

Tell me about a time that you restructured the organisation. Why did you think it was necessary to change the organisational structure? How did you go about doing it? What was the outcome? What did you think were the important factors to the success or failure of this effort? What did you learn from this experience?

How do you approach strategic workforce planning (for example, determining future skills needs, and creating a balanced staffing model)? Give us an example of how you applied strategic workforce planning to address business needs.

Provide an example of what you did when there was more demand for IT services than available resources to fulfill the requests (for example, limited staff or budget). How did you handle the situation? What worked, and what did not work?

Give an example of when you helped reduce costs for the rest of the enterprise by using IT. How did you go about it, and how much did you save?

How do you determine whether an enterprise is investing too little on IT, an appropriate level or too much?

What is the largest IT-related initiative for which you were responsible (for example, cost, elapsed time, scope or team size)? How did you evaluate the success of the initiative, in terms of performance for cost, schedule and quality? What percentage of business case benefits was actually achieved?

What is the largest non-IT-related initiative for which you were responsible (for example, cost, elapsed time, scope or team size)? How did you evaluate the success of the initiative, in terms of performance for cost, schedule and quality? What impact did the initiative have on business performance metrics?

Leadership Skills

The questions below focus on aiding the interviewer to assess a candidate’s leadership views, accomplishments and likelihood of leadership success in the role that the candidate is interviewing for. The most effective CIOs view themselves as business leaders first and IT leaders second. Interviewers should focus on the candidate’s ability to communicate in business terms, articulate measurable business outcomes, motivate people and handle leadership challenges:

Can you share a time where you identified a business problem and applied technology to solve it? What specific actions did you take? What was the outcome or measurable results?

How do you measure and communicate the ROI of information and technology investments?

Can you articulate your understanding of risk and how it applies to IT? Provide an example of how you applied this knowledge to mitigate risk.

What is the most difficult decision you had to make as a leader? Why was it difficult? How did you address it, and what was the ultimate outcome?

Describe a situation in which you exhibited exceptional leadership capabilities. What did you do to make it successful? Describe specific actions and behaviors.

How do you lead your team of direct reports? Give an example of when you resolved a conflict among team members or improved their performance as a team. What approach did you take?

CIOs are often asked to be visionaries and to lead innovation and value delivery through the creative use of technology. Give us an example of where you were a visionary or thought leader. How did you influence the organisation to pursue new ideas? What was the outcome of your efforts? What lessons did you learn? What would you have done differently?

What has been the largest challenge to scale digital business? How have you addressed that challenge? Give specific examples of actions you took and results achieved.

Provide an example of what you did to assess and improve employee engagement. What was the issue? How did you approach it? What was the outcome?

Describe a recognition program or technique you use to motivate and reward high-performing individuals or teams. How did you design and implement it? What tangible outcomes did the program or technique have on your organisation?

Tell us about a time when you led a change initiative that impacted the organisational culture. What were the issues that you were trying to resolve? What challenges did you face? How did you address them? What were the outcomes?

Provide an example of when you built a business case for making a significant technology investment that could potentially lead to business model transformation. How did you build the case? What responses did you receive from senior business executives or the board? How did you respond? What next steps did you take? What were the outcomes or lessons learned?

Tell me about a time when you didn’t get along with your boss. What were the issues? What did you do to improve the situation? What was the outcome? What did you learn to do differently the next time?

Industry and Business Knowledge

The questions below help interviewers assess a candidate’s views on industry trends, the competitive market dynamics, how technology can advance the industry and its members, and the candidate’s knowledge of your business and its competitive position in the industry:

What are the key opportunities, challenges and problems facing this industry? What’s your view of their impact on our business?

What are other industries doing in scaling their digital business that could be leveraged in our industry?

What are some trends you see in technology that have the potential to impact our business or industry, and how and where could we benefit from them?

How might you leverage your knowledge, skills and experience to enable this organisation to play a bigger role in the industry transformation? Where would you focus?

Technical Expertise

These questions focus on determining how the CIO candidate thinks about technology from a value perspective and applies it to solve business problems. The questions can help an interviewer determine how a candidate stays current on technology issues and opportunities in the ever-changing technology marketplace. The questions also can help the interviewer assess a candidate’s ability to communicate about IT in business terms, and in a business context:

What is the most difficult technology-related investment decision you had to make? Why was it difficult? How did you approach making the decision, and what was the outcome?

Give an example of when you implemented a new or emerging technology. How did you manage the risks, and what was the outcome?

Do you set the technical direction in your current role, or does someone else? What process do you use to set the technical direction?

How reliant are you on technical advisors internally and externally, and how do you manage exposure?

How do you stay current on the industry, technology and business trends to fulfill your role effectively?

What’s your view on the most important technical skills to have in the IT department in three to five years (or 5-10 years)? How do you go about determining future skills needs?

Behavioral Competencies

Successful executives demonstrate behavioral competencies that enable them to think and act differently. This set of questions is based on Gartner’s key CIO behavioral competencies. Modify the questions to match your organisation’s context and its expectations for desired behaviors in the CIO role.

Building Relationships

Tell me about a time you were able to successfully work with another person even when that individual may not have personally liked you (or vice versa). What was your approach? What was the outcome? How has your relationship changed with that person?

Business Enterprise Knowledge

Recall a time when the business executives had trouble articulating and prioritising their needs. What were the pressing issues? How did you approach getting the information you needed? How did you validate that you really understood what was required by the business? What was the outcome? How did you know when you were successful in meeting the needs of your customer?

Change Leadership

Describe a situation in which you came up with an innovative idea to solve a business problem. What was the business problem to be solved? What factors drove the need for an innovative solution? How did you determine the best solution? How did you work with both the business and IT to make trade-offs as needed? What tangible benefits were achieved from implementing your solution?

Influencing Others

Tell me about a time when you persuaded senior management to make a significant capital investment. How did you build the business case? What obstacles did you have to address? How did you overcome them?

Innovation

Think about a time when you were a key member of an innovative, high-profile project that failed. What key factors led to that failure? What role did you play, and what actions did you take in that situation? What were the lessons learned from that experience? What would you do differently to improve the success rate of innovative projects in the future?

Results Orientation

Give an example of a situation where a goal stretched you beyond what you were confident of achieving. What was the situation and key challenge? How did you set that goal? What did you do to improve your chances of success? What was the outcome? What did you learn about yourself through that experience?

Risk Taking

Give examples of the types of risks you have taken in the past. What factors did you take into consideration when deciding how much risk you would assume? Were you successful? Why? What would you have done differently?

Strategic Technology Planning

Provide an example of when you dealt with stakeholders who wanted to break away from a shared service, a standardised process or a centralised process. How did you develop your strategy in response to the request (whether you were for or against it)? What was the outcome? What would you do differently if you faced a similar challenge again?

Strategic Thinking

Tell me about an occasion when you were a significant contributor to a strategic plan. What role did you have? What was your thinking process in the development of the plan? What was the intended business impact of your plan after it was executed?

Team Leadership

Describe a time when you led a culturally diverse team. How was that diversity demonstrated, and what challenges did you face? How did you foster a collaborative and inclusive team culture? What was the outcome? What did you learn from that experience?

Ultimately these questions are designed to help enterprises find CIOs who are the best fit for their culture and business objectives. At the same time, CIOs can use these questions to prepare for their next job interview and help them find an enterprise that provides them with challenges that excite them and a culture that fits their values and leadership style.

Tina Nunno is a Vice President and Gartner Fellow in Gartner’s CIO Research group. Lily Mok is a Gartner Research Vice President on Leadership, Culture and People Dynamics within the CIO Research group. 49 CIO interview questions any technology leader should be prepared to answer was the subject of a 2010 article by Tina Nunno. Despite having revisited and updated this above in August 2019, we wanted to keep Nunno’s original for context and because so many of the questions still resonate almost a decade on. [See also: How to become a CIO – Career path to a Chief Information Officer job]

Executives who are hiring a CIO have limited opportunities to assess candidates to find the best fit for their organisation. The interview is a critical step in understanding the capabilities of each CIO candidate and in assessing their individual strengths.

The following sets include questions intended to help hiring executives assess the capabilities of CIO candidates in the critical categories of leadership, strategy and planning, technical expertise, financial management, and operational excellence. Use them as a starting point to plan your interview process.

CIO interview questions – Leadership

Leadership is about understanding how to move people and the business forward. The most effective CIOs view themselves as business leaders first and IT leaders second. These questions focus on helping the interviewer assess a candidate’s leadership views, accomplishments, and likelihood of leadership success from then onward. Interviewers should focus on the candidate’s ability to communicate in business terms, articulate measurable business outcomes, motivate people and handle leadership challenges.

Can you explain how you saw a business problem and applied technology to solve it? What was the outcome?

What significant contribution did you make at your last company? How did you achieve it?

What is your understanding of return on investment and how it applies to IT?

Can you articulate your understanding of risk and how it applies to IT? Provide an example of how you applied this knowledge to mitigate risk.

Can you give an example of when you improved a business process? What was the outcome? What role did you play?

What is your view of your leadership style? Give an example that illustrates it.

What is the most difficult decision you had to make as a leader? Why was it difficult? What was the outcome?

How would you define the role of CIO?

What determines whether a CIO succeeds or fails?

Describe a situation in which you succeeded. What did you do specifically to make it successful?

Describe a situation in which you failed. What did you do specifically that had an impact on failure, and what did you learn or do as a result?

How do you lead your direct reports? Give an example of when you resolved a conflict among team members or improved their performance as a team.

CIO interview questions – Strategy and planning

A core challenge for any executive is balancing long-term versus short-term planning and execution. Many executives are strong in strategic vision but have difficulty gaining support in accomplishing that vision. These questions focus on the CIO candidate’s experience and ability to set long-term goals, while managing the complex task of gaining cooperation to actually accomplish those goals.

What would you do in the first 90 days?

Describe your own approach to governance and how you would determine the best framework for our organisation.

Provide an example of when you explained and sold the concept of IT architecture and standards to business leaders.

How do you gain agreement and cooperation from a diverse set of stakeholders? Provide an example of when you did this successfully.

How do you deal with stakeholders who want to break away from a shared service or a standardised or centralised process?

How do you decide what to outsource and what to keep in house?

Provide an example of when you identified an opportunity to be innovative. How did you find the opportunity and what was the outcome?

Provide an example of when you drove top-line growth or delivered competitive advantage to the enterprise. How did you do it?

Provide an example of what you did when there was more demand for IT than resources to fulfil the requests.

CIO interview questions – Technical expertise

These questions focus on determining how the candidate thinks about technology from a value perspective and applies it to solve business problems. The questions can help an interviewer determine how a candidate stays current on technology issues and opportunities in the ever-changing technology marketplace. They also can help interviewers assess a candidate’s ability to communicate about IT in business terms, and in a business context.

Provide an example of when you convinced senior leadership to make a major technology investment.

What is the most difficult technology-related investment decision you had to make? Why was it difficult and what was the outcome?

How do you stay current on technology trends and innovations?

Give an example of when you implemented a new or emerging technology. How did you manage the risks?

What are the top two or three ways that you and we can measure the value of the IT function? How do you influence each of these in the short term and longer term?

Do you set the technical direction, or does someone else? What process do you use to set the technical direction?

How reliant are you on technical advisors and how do you manage exposure?

What are the most important skills to have in the IT department? How did you go about hiring IT workers or developing those skills in your team?

CIO interview questions – Financial management

All executives must display sound financial management and invest limited resources strategically. This question set focuses on the CIO candidate’s ability to view the IT budget as a portfolio of assets, and to manage it in a manner consistent with the risk profile and strategic approach of the interviewing organisation.

Give an example of when you had to cut the IT budget. How did you go about it, and how much did you save?

Give an example of when you helped reduce costs for the rest of the enterprise by using IT. How did you go about it and how much did you save?

What percentage of enterprise revenue is your current IT budget? How does this compare with your industry peers?

How do you determine whether an enterprise is spending enough on IT, an appropriate level or too much?

What percentage of your current IT spending is for maintenance versus growth and transformation activities? Is that the appropriate mix and why?

What percentage of your IT budget is for outsourced activities? How do you determine what to outsource?

By what percentage did you overrun or under-run your IT budget last year? Why?

CIO interview questions – Operational excellence

Leadership without execution is a formula for failure. This question set focuses on the candidate’s ability to adjust and course-correct as needed to ensure success. Interviewers should look for strong examples of success, where the candidate has delivered clear business outcomes, and evidence of his or her adaptability.

What is the largest IT-related initiative for which you were responsible, in terms of cost, elapsed time, scope or team size? How did you evaluate its success?

What is the largest non-IT-related initiative for which you were responsible? How did you evaluate its success?

How did this initiative deliver in terms of cost, schedule and quality?

What percentage of the business case benefits were actually achieved?

What impact did the initiative have on business performance metrics?

How have you prioritised when there was not enough budget to meet demand?

Provide an example of when the execution of an initiative did not go as planned and what you did.

Provide an example of how you led, motivated and organised a team to achieve during a difficult situation.

While no candidate will display each of the above qualities and capabilities in equal measure, hiring executives can use this interview list to decide which are most important to their enterprises now. While all candidates should have some strength in each of these focus areas, the enterprise’s situation will determine whether leadership, execution or other capabilities are most important to acquire in a new CIO. Use this list as a starting point for your interviews, and then customise it to find a CIO who will not only be able to succeed in contributing to the enterprise’s goals, but also be a strong executive team member and fit for the enterprise’s culture.

CIO interview questions – Key findings

When interviewing for a CIO, the hiring executives will focus on determining the candidate’s ability to deliver business value to the enterprise.

During the interview, focus on the key CIO capability areas of leadership, strategy and planning, technical expertise, financial management, and operational excellence.

The most effective interview responses require candidates to provide specific examples of their past accomplishments and explain how they achieved them, not describe their own personal qualities without putting them in context.

CIO candidates can use these question sets to prepare for job interviews. This preparation will help ensure that they are focused and well-prepared for even the most challenging interviews.

Tina Nunno is a vice president in Gartner’s CIO Research group