In one stretch last year, several executives at the same level in one organization each told me, separately, that the hardest part of their job was talking candidly to each other. Each had spent 15 to 25 years in technology, and none of them was struggling with the technology. I’ve coached more than 1,000 technology professionals one-on-one, and a large share of my practice is now CIOs, CTOs and VPs of engineering and product. AI is supposed to be freeing these leaders from operational work so they can spend more time coaching, giving feedback and working through conflict. What I see instead is that AI is raising the bar on people leadership faster than most senior IT executives can learn to clear it. ## AI hasn’t lightened the load for the IT leaders I coach My clients tell me the relief AI promised hasn’t arrived. They’re expected to produce more, they’re in meetings most of the day and the person above them often doesn’t see how much work the new AI output takes. Several now have a half-dozen AI agents running in the background on top of their existing responsibilities, and nearly all of them oversee teams that do. The agents didn’t replace work. They simply added another layer to supervise, which is one reason so many senior IT executives are burning out without telling anyone. The research matches what I hear. Microsoft’s 2025 Work Trend Index special report found that 52% of leaders say their work feels chaotic and fragmented, and one in three employees said the pace of work over the past five years has made it impossible to keep up. Deloitte’s 2026 Global Technology Leadership Study, which surveyed more than 660 senior technology executives, found that 41% report their organization sees them as unable to keep up with demand. AI is also creating decisions that didn’t exist a few years ago. One engineering leader I coach at a large tech company co-leads an organization of a couple hundred people with his product counterpart. The two of them now receive a monthly budget of AI tokens and have to decide together how to allocate them across their teams. That’s a negotiation between peers over a scarce resource, and it lands directly on the skill most of my clients tell me they struggle with. The leaders I interviewed for this piece described the same split. Yogesh Joshi, senior vice president of global AI platforms at TransUnion, said AI is accelerating the product development lifecycle at his company, but that “it does not create trust, resolve conflict, develop talent or align teams around shared goals.” Diya Jolly, chief product and technology officer at Xero, said AI can draft a product requirements document or scaffold production code in minutes, but it can’t “own the hard tradeoffs, like do we build feature A or B?” That’s how AI exposes weak people leadership. When it absorbs the technical work, what remains is the people work, and the people work is where many senior IT leaders have had the least practice. ## Difficult conversations are the gap I see most often The executives I described at the start weren’t unusual. Most of the CIOs and VPs I coach struggle with some version of a hard conversation, even though they’ve been leading for decades. Some can’t give their CEO tough feedback. Others put off telling a direct report they missed the mark. The most common, and in my experience the hardest, is the conversation with an executive peer. Product and engineering are where I see it most. One client, a senior engineering leader, held off for months on a conversation with his product counterpart about who owned the roadmap and who decided which features got prioritized. He shared with me that he was worried about stepping on the other executive’s toes. When the two of them finally talked, the conversation was awkward, but they got aligned, and the conversations that followed got easier. Marketing shows up in these disputes too, though in my experience those conversations tend to be less heated. Breno Oliveira, CTO at Strider, described a version of this from early in his leadership career. Not long after stepping into a new role, he felt he had to give feedback about a close teammate’s performance on a project, but he held off. “Delaying the hard conversation was a mistake, it cost a few more weeks of misalignment,” he said. “The actual conversation turned out to be far easier than the versions I planned.” Part of the reason these interactions seem scary is where these leaders came from. Many built their careers in roles where having the right answer was the job. Paul Farnsworth, president and former CTO of Dice, put it this way: “Technical expertise may help get you into a leadership position, but succeeding in that role depends on fundamentally understanding business priorities and communicating with people who have very different perspectives and objectives.” Few of my clients were ever trained for that second half. Gallup’s 2026 State of the Global Workplace report notes that few managers have natural management talent and many haven’t received the training they need to coach their teams. The same report found manager engagement fell from 27% to 22% between 2024 and 2025, the largest year-over-year drop Gallup has recorded. AI won’t fix any of this. It takes over the technical work these leaders were good at and leaves them with the conversations they’ve been avoiding. ## What I coach IT leaders to do instead When a client is dreading a conversation, I start by asking what they want out of it. Why does it matter, and what does a good outcome look like? Technical leaders often go into a conversation wanting to convince the other person of their point of view. They want to give direction or advice. I ask them to set that aside and think about what they need to learn. Then I have them go through their calendar for the day. For each meeting, they write down one, two or three questions that will move the conversation or the decision forward. Many of my clients now do this daily, the evening before. Some print their calendar. Others work through it on screen, one meeting at a time. The prep shifts from a page of talking points to a handful of questions, and they make more progress in the room because they’re listening instead of trying to convince. The leaders I interviewed use similar approaches. Farnsworth, the Dice president, said he used to get flustered in difficult one-on-one conversations with the people he managed early in his career, and he learned to write down his key messages beforehand so he could stay focused and communicate more clearly. Joshi, the TransUnion executive, said the best leaders he knows “spend less time giving answers and more time asking questions,” and he advises rising IT leaders to treat coaching as a skill that requires deliberate practice. Jolly, the Xero executive, said she had to start fiercely protecting her calendar to carve out thinking time, and she advises leaders to hire people who can do their jobs without them. I also remind clients that having hard conversations is a skill, and skills improve with reps. The engineering leader with the token budget didn’t get better at negotiating with his product counterpart by reading about negotiation. He got better by having the conversation, debriefing it with me and having the next one. The market has already noticed. CIO.com reported earlier this year that companies hiring CIOs in 2026 want a business transformation officer with a technical pedigree and high emotional intelligence, and that relationship skills matter more than ever. AI isn’t coming for the CIO’s job. It’s coming for the part of the job that used to hide weak people skills behind strong technical delivery. The leaders who will thrive are the ones who treat difficult conversations as core work rather than an interruption and start practicing before the exposure arrives.

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