Talk to CEOs today and some common themes emerge: they’re moving faster, making bigger bets and relying more heavily on technology to execute their strategic agenda. Expectations on the IT estate have never been higher, yet many CEOs feel it’s a “black box” – essential, but difficult to see into and even harder to gauge.
At the same time, CIOs know that aging infrastructure is struggling to keep pace with AI-driven transformation, rising cyber risks or the agility their CEO has come to expect.
This expectation gap is exactly why Netskope’s Crucial Conversations research identifies the IT estate as one of the six essential discussions CIOs must master today if they are to successfully align with their CEO on their modernization agenda.
CEOs’ growing frustration with the “black box”
CEOs that took part in the research admitted they don’t understand what’s happening deep inside the IT stack and that makes them uncomfortable. Some feel their CIO shields them from the complexity; others feel the CIO overcomplicates it. Either way, this impacts confidence.
Why the IT estate has become a strategic conversation
Three forces are pushing the IT estate onto the CEO agenda faster than many CIOs expected:
1. AI demands modern foundations
Organizations are moving from AI experiments to AI integration at pace. But AI doesn’t run effectively on infrastructure designed for a pre-AI world. CEOs need to understand that modernization is not a technology preference – it’s a prerequisite for delivering the business outcomes they now expect from AI.
2. The cost/risk trade-off is shifting
CEOs expect CIOs to be “gatekeepers” of cost, challenging suppliers and avoiding unnecessary spending. But they also expect CIOs to be candid about the real cost of doing nothing – outages, slowdowns, security exposure and innovation bottlenecks that compound, year after year.
3. The estate has moved from technical debt to strategic debt
Aging infrastructure no longer just slows down IT; it slows down the business. It limits agility, restricts transformation, and reduces competitiveness. CEOs may not use the words “technical debt,” but they understand when the organization is weighed down by the past.
How CIOs should reframe the conversation
To build trust and alignment, CIOs need to take ownership of this conversation rather than waiting for disruption to force it, and CEOs want three things from them.
They want issues surfaced early and directly, with no surprises. CIOs need to lead with transparency.
Second is proactivity and the confidence to embrace change, make bold strategic calls, and recognize that even small fixes can have outsized impact, especially in an AI-driven environment.
And third is practicality. CEOs aren’t interested in “new toys,” but in well-evidenced, sensible solutions that reduce risk and address problems decisively when they arise.
Above all, they want CIOs to think long term, planning infrastructure over the next decade rather than the next budget cycle and moving beyond an “if it isn’t broken” mindset.
The moment for this conversation is now
Most enterprises are at an inflection point. Modernize the estate to unlock AI-driven advantage or carry forward a legacy footprint that cannot support the ambitions the CEO now expects the CIO to deliver. The CIO who leads this conversation will be seen as a true strategic partner.
Explore all six crucial conversations
The IT estate is only one of six crucial conversations CIOs need to master with their CEO. To dive deeper into the rest – cost, risk, innovation, people and measurement – read the full Crucial Conversations report now.
