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5 CIO Interview Questions You Should Always Ask

Kristin Bachman
5 min read

To stay competitive, it’s essential for companies to develop their business and technology strategies in conjunction - it’s no longer effective to keep the two siloed. In 2022, to stay relevant in the technology industry, The 2022 State of IT reported a record 53% of companies that plan to expand their IT spending contrasting the humble increase they experienced in 2021. Technology is advancing, fast. In order to meet demand, companies are in need of dynamic teams led by a deliberate Chief Information Officer. 

Occupying an even more pivotal role in the current business environment where rapid adaptation is necessary for success, CIOs that drive technological integration and methods within their company are in high demand. It has become extremely apparent how crucial it is for hyper-growth companies to bring on a CIO in order to be in the vanguard of technology startups and companies. 

In 2021, IBM reported on the ‘CIO Revolution’ that is taking over and is shaking up how the industry values company growth and evolution. As a result, the role of technology leaders has expanded beyond a company’s core IT services. Businesses are looking for CIOs who can not only meet fast-changing demands, but are also strategic leaders who understand and execute on business objectives and outcomes. 

In addition to a strategic mindset, organizations need to recruit CIOs who possess the following skills and expertise: 

  • The ability to integrate current IT systems with new ones, while cost-effectively managing a secure data infrastructure.
  • The knowledge to leverage technical infrastructures to achieve positive business outcomes (revenue growth, business margins, and strategy).
  • Leadership skills to direct and manage teams through technological advancements and shifts.

Here are five helpful CIO interview questions and answers. Learn why these questions matter and the types of responses you should look for to find the most qualified talent.

1. How have you leveraged technology to help your organization?

Why ask: A CIO plays an essential role in keeping their organization nimble - promoting and driving digital transformation when needed. It’s essential to hire a CIO who can see the big picture goals of the company, and understands how to leverage technology strategically to impact business outcomes that can generate a significant competitive advantage.

Elements of a good answer:

A thoughtful candidate should include:

  • How they automated important business processes and increased efficiencies in previous roles. 
  • How they adopted key technologies, including AI, low-code/no-code, gamification, and data harvesting, and integrated them into their team and company.
  • How they implemented technological changes to increase company agility.   

Candidates with ample experience and drive will answer by explaining their approach to the role and how it impacts the business from a strategic perspective. Look for examples that point to how they utilized technology resources, such as low-code/no-code and automation technologies to connect business functions or improve operation results. 

2. How have you developed a digital transformation solution in the past? And how would you start a digital transformation at our organization? 

Why ask: A CIO is responsible for the digital transformation of their organization. Therefore, this question’s intent is to identify whether the candidate can proactively address evolving digital trends, while supporting and addressing the company’s needs. It will also help the interviewer understand if the candidate possesses the right collaborative skills to launch and manage digital transformation projects with fellow executives and staff members 

Elements of a good answer:

The ideal candidate will discuss how they will get their digital talent on board. Specifically, how they plan on: 

  • Filling the gap between talent supply and demand
  • Aligning talent with long-term organizational objectives
  • Future-proofing the talents of their team (e.g. reskilling and upskilling individuals so they are equipped to adapt to change) while staying within their departmental budget.

The ideal candidate understands that digital transformation is about your talent—not your technology. Having cutting-edge technology is only beneficial if you have trained talent ready to unlock its full potential. 

3. Which IT metrics would you monitor on a daily, weekly, and monthly basis? 

Why ask: Data is central to a CIO’s role, so you want to ensure the candidate has a data-driven mindset. This question will also demonstrate their experience level in managing IT systems. It will spotlight what quality means to them in the tech field and how they measure quality. You will also be able to identify how they leverage technical infrastructures to help drive bottom-line results.

Elements of a good answer:

A deliberate candidate will share insights on their previous companies to help them identify possible metrics. They will follow up by discussing what metrics they used in their current or previous roles.

Metrics vary across industries, but an adequate answer will be a holistic one that hits four main areas: 

  • Operational metrics: Operational metrics aim to measure the performance of a given software or application. The ideal candidate will also align these performance metrics to the organization’s overarching goals. 

  • Delivery metrics: Whether it’s the time it takes to achieve business goals or the level of project satisfaction, delivery metrics focus on assessing the quality of a given task.

  • Organizational metrics: These metrics should focus on employees’ performance and progress on project tasks.  

  • Financial metrics: Your candidate should bring up cost and revenue indicators that can help you assess how well they can manage budgets.

Candidates may explain they need a better understanding of your internal processes before they can establish key metrics to share. By asking for further internal context, their answer is a strong one, as metrics should align with an organization’s workflow and goals. 

Consider adding follow-up questions that allow a candidate to elaborate on why they chose each metric to further demonstrate their experience in IT management.

4. What kinds of resources do you plan to rely on to stay updated on the most current technological shifts in our industry? 

Why ask: As the IT industry is continually evolving, this question can reveal whether a candidate has a forward-thinking mindset. The right individual consistently has their ear to the ground, staying aware of current and emerging software and data trends. 

More importantly, while new technologies are exciting, the candidate understands that not all trends will be well-suited for the organization. Thus, this interview question also deciphers how practical and grounded one’s attitude is toward technology. 

Elements of a good answer: 

A good candidate will:

  • List specific professional IT resources, publications, or industry competitors they regularly track and evaluate. 
  • Express a willingness to learn and grow from their resources. 
  • Describe specific takeaways they’ve gained from the resources.

Candidates with a list of advantageous resources and publications to refer to demonstrate leadership aptitude. It shows that they are continuously learning and bettering their ability to be a leader in the technology field.  

5. Pick a complex technical solution you have previously worked with. First, explain it as we are your peers. Second, explain it as though you were selling the solution to an executive board. 

Why ask: As noted earlier, CIOs must be builders of technology and the business. Therefore, in addition to possessing a technical mindset to unlock IT solutions, they must have the interpersonal skills to present that information in an approachable way to a non-technical audience. 

Elements of a good answer: 

You should expect the first half of their answer to: 

  • Be rich with figures and facts. 
  • Communicate the information, using technical language common in their industry. 

If you, as the interviewer, do not possess a technical background, you may want to invite someone who does to the interview. That way, you can have someone who can vouch for the candidate.

During the second half of their answer, the candidate should:

  • Simplify and add value to complex technical terms. A good response will entail language a non-technical audience will understand. 
  • Go on to highlight the main value proposition of the technical solution.

It’s important that they can translate complex technical jargon in a practical way, in order to be well-suited for the role of CIO —a role where negotiating with (non-technical) executives to find cost-effective and shared solutions is crucial.

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