Recommended interview questions to ask your CIO candidates.

The responsibilities of CIOs are broad and deep. They are accountable for seamless operations, cost control, vendor management, innovation, delivery, team development, architecture, and business engagement. And not all CIOs are alike. They can be deep technologists, operational leaders, or visionaries. When hiring a CIO, what most CEOs, CFOs and COOs want is balance.

At Heller Search, we’ve developed an interview guide to help our clients assess a CIO candidate’s experience in all of the major areas of IT leadership.


Team management

Interview Question: How have you changed the culture of your current IT organization? 

What to listen for: Concepts like “client focus” and “consultative approach.”

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Interview Question: On a scale of 1 to 10, how would your current business community rate your IT organization? How do you know?

What to listen for: A concrete methodology for determining customer satisfaction.

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Interview Question: How are you developing “blended” IT leaders who know technology and have an understanding of the business context in which they are working?  

What to listen for: A programmatic, strategic approach to leadership development and to fostering a business focus in IT.



Interview Question: Tell me about a transformation that you’ve led that has had a positive impact on your business.

What to listen for: Examples of cross-functional leadership and the ability to reach across the enterprise to get business partners on board.

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Interview Question: What are your most important relationships in your current role, and how do you maintain them?

What to listen for: Examples of building trust through delivering on promises.

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Interview Question: Tell me about a time when you’ve had to exert influence over your company’s executive committee?

What to listen for: The candidate's use of data to get his or her point across.


IT Strategy

Interview Question: What is your experience with digital transformation? 

What to listen for:  Digital strategies that extend well beyond marketing and social media, into areas such as supply chain, employee productivity, and more.

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Interview Question: What is your company’s current IT strategy?  

What to listen for: Well organized answers that clearly connect the IT strategy with the company’s business strategy, and that do not go into deep technical detail. Also, inclusion of talent development as a critical part of their IT strategy. 


Vendor Management

Interview Question: What are the important elements to making a vendor relationship successful?

What to listen for: A thorough understanding of the new pricing models that cloud and SaaS providers have introduced. Also, the concept that vendors can be true valued partners.



Interview Question: How do you strike the balance between operations and innovation among your IT staff?

What to listen for: An organizational design that ensures that IT is not always stuck in the weeds, too busy with operations and no time to learn, ideate and innovate.

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Interview Question: Can you describe a major new digital product or business process innovation that your company has produced in the last year? What was IT’s involvement in that initiative?  

What to listen for: Whether IT was involved early in the initiative, helping to develop the idea, or called in only when it was time to deploy.


Business Engagement

Interview Question: How do you ensure that your company’s IT investment dollars are being spent on the right initiatives? 

What to listen for: The concept of IT investment decisions as business decisions, one that the CIO facilitates and guides, but does not own.

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Interview Question: How do you ensure that projects are delivered on time and on budget?

What to listen for:  A structured project management methodology; and a compelling story on how the candidate has improved their delivery capability using Agile and other iterative processes.

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Interview Question: What organizational structure allows for the best relationships between IT and its business partners?

What to listen for:  Concepts like business relationship management, product management, running IT as a business, and other formal operating models that allow IT to partner successfully with its stakeholders. 

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