CIOs' Hardest Problem Isn't AI. It's Leading People.

Under pressure, even capable leaders fall back on habits that don't always fit the moment. Executive coach and former CIO Jessica Kral finds that leaders who are thriving are doing a few specific things: they stay honest about what they don't know, translate ambiguity into direction, and keep their people at the center.

I recently interviewed seven technology C-suite leaders about their biggest challenges right now. Of course I heard about AI. But the real conversation was about people.

Yes, AI is the catalyst. But the deeper challenge I heard had nothing to do with the technology itself. It was about how to guide organizations, teams, and partners through uncertainty and rapid change. As I reflected on my own years as a CIO, I realized this has always been true: leading people is the hardest part of leading technology.

In my conversations with technology executives, a pattern emerged. Under this kind of pressure, even the most capable leaders tend to fall back on the habits that carried them this far—and those habits don't always match the moment. But some are handling it remarkably well. What follows is what I learned about why this era feels different, what happens when our default responses don't hold up, and what thriving leaders are doing differently.

The Pressure Is Real

Every leader I spoke with described a similar environment: an urgent mandate to deliver AI results and a pace unlike anything they've experienced. These are seasoned leaders. They've navigated mainframe to client-server, client-server to web, web to mobile, on-premises to cloud. They know how to deliver technology change. And they're telling me this time is different.

Two things stand out as genuinely new.

The first is speed. Not just the speed of change, which has always been part of the job, but the speed at which people expect results. Eighteen months ago, experimentation and proofs of concept were acceptable. Now the conversation is almost exclusively about achieving outcomes quickly. One CIO I spoke to put it bluntly: "A couple of years ago, the pressure was to do something—anything—with AI. Proofs of concept, pilots, experimentation. There wasn't much focus on value. That has completely shifted, and now the finance team is requiring proof. They want to know where the cost came out in this year’s P&L." And it isn't only finance looking for value. It's the market, the analysts, and the board. When the demand for immediate results meets tools evolving faster than organizations can absorb them, the speed can send people spinning.

The second thing that stands out is harder to name but may matter more. In previous cycles, the responsibility for implementing new technology largely stayed within technology organizations; business leaders consumed the outcome. AI is different. Business leaders are now expected to have a plan, a strategy, and a point of view on AI. They are being told not just to support it, but to own it. At the same time, the barriers to building technology have diminished or even disappeared. You no longer need to know how to code or manage infrastructure to create something. Almost anyone can build now.

That combination of everyone expected to have an answer, and almost anyone able to act on it, creates a leadership challenge few have faced before. And it’s technology leaders who have to navigate it.

What Pressure Reveals

Here's what I've noticed: pressure doesn't reveal weakness; it reveals the default. When the path is unclear, and the stakes are high, leaders unconsciously revert to what has always worked for them. And sometimes those instincts become a liability.

Here are some examples I’ve seen:

• A CIO who had built a high-performing team by trusting them to own their domains found herself making decisions without their input during a cybersecurity emergency. Instead of providing their wisdom to help address the situation, the team wasted time balancing making their boss look good and fighting the fire.

• A tech executive with deep expertise, who had learned to present complex topics as crisp, executive-level recommendations, fell back into overly detailed explanations when pressed to defend an additional technology investment. She lost the room and with it, the funding her team was counting on.

• A business leader known for empathy thought he was protecting his team by not sharing the company's financial struggles. He kept everything positive thinking the situation was temporary. When it all came out, the team was blindsided. As a result, the trust he'd built with them took a serious hit.

• A technology leader who had advanced by staying on top of the latest trends answered a board question with old data. He knew things were changing fast, but his default was to answer quickly and confidently. He and his team then had to absorb the consequences of a board commitment based on faulty information.

None of these leaders was failing. They all were human. And in an environment moving this fast, the difference between one's default settings and what the moment needs can be vast.

What Thriving Looks Like

The leaders who stand out aren't the ones with the most answers. They are the ones who have learned to absorb pressure rather than transmit it, translate ambiguity into direction, and take their people with them.

I see leaders being more transparent about their own uncertainty. The instinct under pressure is to project confidence, but the best leaders resist it. They replace that instinct with something more honest and more useful: here's what I do and don't know, here's what I'm working to get clarity on, and here's what I'm going to make the call on.

I have also seen a shift in the questions the most effective leaders ask. Instead of "How do we solve this?" the question becomes "What can we do with what we know right now?" It sounds like a small distinction, but it isn't. The first can paralyze a team if the needs aren’t clear. The second absorbs the pressure and keeps the team moving.

The reality is that the direction is often missing. Business partners and clients who traditionally defined the requirements are facing the same uncertainty as everyone else. Some technology teams are being asked to go further and define the need themselves. Brian Schulte, CIO at Optum Whole Health Solutions & Optum Serve (UnitedHealth Group businesses that provide population health services and federal health programs for the military and veterans), describes the shift this way: “Technology is no longer just delivering what the business wants. We are driving strategy. That means my team needs to understand the responsibility that comes with that, and be clear about when they are empowered to drive and when they need to bring me in." For a team accustomed to receiving direction, a leader who helps them through that new responsibility makes all the difference.

And I see them checking in differently with their teams and spending time finding out what people need to do their best work in a hard environment. That requires setting aside the pressure long enough to be fully present with the people feeling it, too. Nasir Ahmed, CTO at CoverMyMeds (a wholly owned subsidiary and core business unit of McKesson), captured something essential about this moment. "When you move at that kind of speed," he told me, "you have to take humans with you." That kind of steadiness doesn't come from having all the answers. It comes from knowing who you are as a leader and staying grounded when everything around you is moving fast.

The Leadership Opportunity

The technology challenge is real. The pace is intense. The expectations are high. The paths are rarely clear. And yet, in every conversation, underneath the strain and uncertainty, I heard leaders recognize that this moment, as demanding as it is, is also an opportunity.

Those capitalizing on the opportunity aren't waiting to be asked. "You have to perform to earn the right to transform," a CIO at a property and casualty insurance company told me. The leaders who understand that and bring their people along as they build it will define the next era of technology leadership.