5 questions every aspiring CIO should be prepared to answer

CIOs, CTOs, and CISOs present budgets, digital transformation programs, and risk management priorities to the C-suite and board with greater frequency these days. But IT leaders who aspire to C-level roles have few opportunities to show key executives what they know. So, being prepared for those 30 seconds caught in the proverbial elevator with the CEO or a board member is critical because it may be your only opportunity to make an impression that paves the way for future C-level opportunities.

To shine in these moments you’ll need to illustrate your business acumen and tell a story about how technology is delivering business value at your company. And while there isn’t one right way to answer an executive’s off-the-cuff question at the watercooler, the first rule for aspiring IT leaders is to be prepared to answer any business executive’s questions in a way that avoids technical jargon and leaves a lasting impression by knowing the business’s primary objectives, growth targets, and operational goals.

Below are five questions that IT leaders aspiring to CIO and CTO roles should know how to answer when asked. Together they build a foundation for showing you have the mettle to make good on your C-level aspirations.

How are IT’s key initiatives delivering business value?

At a recent Coffee With Digital Trailblazers, Joe Puglisi, growth strategist and fractional CIO at 10xnewco, hosted a contest among technology leaders on who delivered the best response to key questions IT leaders may face when running into business executives. His question, “What business value did your last cloud migration deliver?” drew answers such as, “It allowed me to recuperate some cost in infrastructure,” “It made sure we got faster speed to market,” and “It improved business agility compared to fragmented older systems.”

Those are solid enough answers, but specific results that qualify and ideally quantify the realized business value would be preferred in making that lasting impression. Puglisi advised starting the answer by stating the objectives of the cloud migration and then sharing the results. Heather May, president of May Executive Search, suggested treating executives like clients by aligning the response to their interests and including a key learning from the initiative.

Similar questions about typical IT initiatives, such as around the growing costs of cybersecurity, drew exemplary answers. For example, Joanne Friedman, PhD and CEO of Connektedminds, responded, “What is the cost of recuperating all of our customers, our brand value, and our production capabilities? If you look at that in comparison, investing in information security is actually less than what we should be spending.”

The key to answering such a question is to focus on value delivered from past initiatives and targeted in current ones. Describe the initiative minimally, and instead specify which executives and department leaders IT is partnering with to deliver the value. Lastly, select initiatives that align with the business’s top strategic priorities.

How are we using technology to drive growth?

Board members consider leveraging technology for productivity improvements table stakes for well-run IT organizations. What they and many business executives are more interested in are the growth and disruption opportunities afforded by technology investments.

“You can find a lot of people who can talk a lot about technology and deliver programs,” says Stijn Christiaens, co-founder and chief data citizen of Collibra. “Convince the higher-ups that your technical approach and AI solutions drive business value, monetization, and revenue.”

Ross Meyercord, CEO of Propel Software, says, “CIOs lead with foresight, setting the pace ahead of where the business is going.” He recommends answering the question by showcasing where IT is a catalyst for future revenue opportunities and how you’re developing in-house skills and partnerships to accelerate the delivery of new technology capabilities.

Review the company’s growth strategies from public filings, press releases, and internal presentations when preparing to answer this question. Focus on answering how the business plan drives growth and where technology investments are enablers. Avoid getting into the weeds on the technology, the plans to roll it out, or other implementation details unless specifically prompted by the executive.

What’s the biggest technology risk we’re facing today?

Ram Chakravarti, CTO of BMC Software, says to answer, “How are you helping me sleep well at night?” as a more relevant alternative to this key question.

Chakravarti suggests focusing your response on the solutions, strategy, and business impacts rather than diving into the latest security and operational risks. Your answer should help convey a message: “Relax, I have your back and am leading the company to be more operationally resilient.”

Chakravarti’s response to this question is, “By making sure the worst thing you can imagine never makes it to your inbox. We design for disruption, not just uptime, so we recover fast and stay operational when the unexpected happens. Every critical system has a plan B and a tested one at that.”

But there is a completely different approach to answering this question if your strengths lie in delivering innovations, customer experiences, and transformational outcomes. The biggest technology risk is falling behind competitors, losing customers, diminishing market share, and other disruptions if the company isn’t investing aggressively in technology and delivering outcomes from these investments. Answer the question on risks by highlighting where technology will improve competitiveness and the steps the organization is taking to deliver technology differentiators faster than the company’s competitors today and in the future.

A third approach to answering this type of question relates to how technology impacts the future of work, including people skills, job responsibilities, and workflow efficiencies. For example, Anant Adya, EVP of Infosys Cobalt, suggests using this prompt to answer, “How are you preparing your organization for an AI-first future?”

Rami Mazid, CIO at Nutanix, suggests answering a broader question on how you are enabling and reshaping the business. “Being a CIO is not really about running or managing the entire business. It’s about how that person will help transform the business and truly enable the employees to be the most productive in the work environment.”

What emerging technology should we be exploring now?

Any questions about technology investments and choices are trick questions. Most executives are not interested in implementation details or how the organization invests in emerging technology POCs.

Instead of diving into technobabble, IT leaders should focus on competitive differentiation, where technology enables growth, and how innovations improve customer experiences.

For example, generative AI is a hot topic right now, so it’s likely an executive will ask about where the company is investing in AI capabilities.

“It’s really about differentiation. Explain where you are introducing AI in your core products and services that are customer-facing and where the majority of the value is created,” says Dr. Philipp Herzig, CTO at SAP. “For example, underwriting in insurance, there’s a lot of room for innovation and differentiation right in the core products.”

When the media is covering a hot technology like gen AI, your answer should focus on where your organization is already delivering business value from AI and what new capabilities are on the near-term horizon. Share how you use AI agents in strategic platforms to improve productivity and enable highly impactful decision-making. For example, you might connect how AI is helping the organization optimize supply chains with the recent tariff announcements, then offer a second example of how the organization uses AI to improve customer experiences.

What is IT doing to improve its agility and effectiveness?

Executives with financial, technology, or operational backgrounds may ask about the IT department’s agility and effectiveness, which is really about how IT continuously improves its performance. Phillip Goericke, CTO of NMI, says to answer how IT creates leverage that drives enterprise value and to demonstrate that IT is not just overhead.

For example, Goericke suggested answering: “I build environments where others can make fast, high-quality decisions without me by giving them clarity, business context, and ownership, along with the freedom to experiment and make mistakes. My job isn’t just to run a great tech org — it’s to scale good business outcomes, accelerate growth, and increase the enterprise’s value as if I owned every share.”

Another approach to answer this question is to focus on a common problem facing IT departments and then demonstrate your solution.

For example, many organizations’ AI ambitions are held back by siloed applications and outdated data management practices. Manish Sood, CEO, founder, and chairman of Reltio, suggests answering, “To unlock AI’s full value, we need unified, trusted, real-time data in motion across every system, every interaction, and every touchpoint. We need to transition toward data-centric computing, where data — rather than applications — is treated as the enterprise’s most critical, long-term strategic asset.”

These questions come in many variants, and there’s always the oddball question that might come up. The best practice in handling executives’ questions is to avoid letting the mouth outpace the mind. Instead, pause, think, and then respond. Give your mind a chance to understand the question’s context and recall the executive’s background and interest. When you respond, focus on the business opportunity and value, not the technical details.