Hiring IT Executives: A Media Organization Case Study for Hiring a CIO
Why Most Companies Get CIO Hiring Wrong—and How to Fix It
Due to my background in the global media industry and a decade of experience as a CIO, I recently had the opportunity to consult with the leadership team of a medium-sized media organization about hiring a new Chief Information Officer. What unfolded was a revealing and, frankly, concerning conversation.
The executive team, comprised of the CEO, COO, and CFO, admitted, without hesitation, that they had no idea how to work with a CIO. They didn’t know what the CIO should be responsible for, how to assess their performance, or even how to communicate with them effectively. One comment from the CEO stuck with me: “We don’t even know the right questions to ask.” To make matters more complicated, they weren’t even sure who the CIO should report to.
This company had recently let go of their former CIO due to operational failures that revealed a deeper issue: the IT team lacked critical capabilities. The board took notice, and for good reason. They flagged this to the CEO and the broader leadership team as a systemic failure of oversight. It was a wake-up call, and a necessary one.
Based on this experience, I wanted to share some key insights for hiring IT executives, especially at the leadership level, and highlight the role executive teams must play in understanding their IT environments.
Understand Your Business
Before you can evaluate or hire a CIO, you need to understand your own business. This might seem obvious, but it’s surprising how many executive teams lack fluency in the operations of their departments, especially IT.
Each executive should be fluent in their own domain, but they should also have a baseline understanding of what other departments do, particularly departments as essential as IT. If you can't communicate effectively with a peer executive, that's a leadership gap.
This applies not just to CEOs hiring CIOs, but also to CIOs hiring VPs of Infrastructure, Application Development, or Cybersecurity. If you don’t have deep expertise in a specific area, you need to learn enough to ask good questions, evaluate candidates, and understand what "good" looks like.
In this case, we were talking about a media company, a business that fundamentally depends on technology to deliver content. Yet their IT department was underfunded and underappreciated. That’s a strategic misstep. Every company today is a tech company to some degree, but media companies live and die by their ability to use tech effectively.
If you can’t get your media to the masses, you don’t have a viable product. Your IT investment should reflect that reality.
Understand the Role You're Hiring For
How can you hire someone if you don’t understand what they do? You can’t. And you shouldn’t.
If you don’t understand the CIO role, pause the hiring process. Bring in someone who does. It could be a trusted advisor, a former CIO, or a panel of experienced technology leaders. Use them to help define the role, vet the candidates, and support your decision-making.
The same logic applies when a CIO is hiring senior IT leaders. You should already know the functions of the roles you’re hiring. That knowledge should guide your interview questions, helping you evaluate both technical proficiency and cultural fit.
And here’s a critical piece of advice: don’t have subordinates interview their potential boss. That dynamic is backwards. It undermines the authority of the incoming executive and creates unnecessary politics.
If you want a technical vetting process, build an evaluation panel of outside professionals who are peers or senior to the role you're hiring. This approach ensures the process remains unbiased and free of internal agendas.
Establishing the Right Reporting Structure
One of the recurring issues I see is confusion around where the CIO should sit in the org chart. In some companies, the CIO reports to the CFO, which can limit their strategic impact. In others, they report to the COO, which might make sense if operations are tech heavy. But ideally, in a digital-first world, the CIO should report directly to the CEO.
Why? Because technology strategy is business strategy.
CIOs today aren’t just overseeing infrastructure and help desks. They are pivotal in product delivery, customer experience, data strategy, and innovation. Burying them two or three layers down in the org sends the wrong message and diminishes their ability to contribute.
If you want to get the most out of your CIO, give them a seat at the table.
How to Interview a CIO
Interviewing a CIO isn’t the same as interviewing other executives. The blend of skills you’re looking for includes deep technical understanding, strategic thinking, leadership, and business acumen.
Here are some guidelines:
Ask about impact. What business outcomes have they influenced through technology?
Dig into failures. What major projects failed under their watch, and what did they learn?
Explore communication style. Can they translate tech-speak for the boardroom?
Gauge cultural alignment. Are they a builder, a fixer, a transformer? What does your company need?
Test their knowledge. Use an external panel of tech leaders to evaluate their technical depth.
Building a Partnership Culture
If you want your CIO to succeed, the rest of the executive team needs to see IT as a business partner, not a service provider. This means inviting them into strategic conversations early, not just calling them when something breaks. I talked about this in my Chief information Officer equals Business Partner…Business Strategist article.
Culture matters. IT can’t operate in a silo. They need to collaborate with marketing, product, finance, and operations. That collaboration starts at the top.
Final Thoughts
Hiring the right CIO isn’t just about filling a role, it’s about setting your organization up for long-term success in a digital world. But success starts with understanding.
If you don’t understand the role, invest the time to learn. Bring in experts to help you assess candidates. Create a structure where your CIO can thrive. And above all, treat technology as the strategic asset it is.
Because at the end of the day, if you can’t get your message to your audience, someone else will.