The accidental CIO is disappearing, and that might be a problem

When I first became a CIO, remarkably few CIOs I knew seemed to have set out to become one.

In fact, the title itself was still relatively unusual at the time. In many organizations, the most senior technology person was the IT Director. The idea of deliberately building a career towards becoming a CIO wasn’t how most of us thought about it.

We arrived there almost accidentally.

People came up through programming, infrastructure, operations, projects or business systems. Careers zigzagged rather than followed carefully designed paths. You took something on because it had broken, or because somebody had been fired, got dragged into an acquisition, found yourself negotiating a major contract, or suddenly found yourself, as I once did, standing in a boardroom trying to explain why something had gone horribly wrong.

Looking back, it was a remarkably unstructured way to develop a senior executive. But I’m beginning to wonder whether that was also its strength. Somewhere in all that career messiness, we acquired breadth.

Today we’re much better at developing technology specialists and creating defined career paths towards senior leadership. Surely that’s progress?

I’m not so sure anymore.

I’ve been guiltier than most. I’ve spent years trying to create career paths for my teams: defining roles, competency frameworks, development plans and logical routes towards leadership. It felt like exactly what a responsible CIO should be doing. Best practice, even. But I’m beginning to wonder whether, in professionalising those career paths, we’ve accidentally engineered out some of the messiness that developed us.

Not certificates. Not CPD credits. Experience.

I see this increasingly when I talk to people who want to become CIOs. An aspiring CIO will sit in front of me with a folder full of certificates, accreditations and courses they’ve completed. They can confidently explain what they’ve studied. But when I put the folder to one side and ask, “Tell me what you’ve achieved,” the conversation can become much harder.

Tell me about the transformation you led. The failing program – yes, we all have one. The acquisition you integrated. The sceptical CFO you persuaded. The commercial decision you got wrong and what you learned from it. The team you built. The board you had to convince.

That’s the experience I want to hear about.

My concern is that we’re becoming very good at helping future CIOs prove what they know, while the modern CIO role increasingly demands evidence of what they have done. And there’s the paradox: Technology careers are becoming more specialized and qualifications more structured at precisely the moment when the CIO role requires greater breadth of experience.

Worse still, much of the formal development I see aspiring CIOs undertaking seems designed to prepare them for the CIO job as it existed five years ago. The job has moved on. Specialization is getting deeper while the CIO role is getting broader

Looking back, some of the experiences that prepared me most for senior leadership weren’t things anybody would sensibly have put into a development plan. They were problems. None came with learning objectives, CPD credits or a certificate at the end. But they taught me. It wasn’t elegant career development. But it produced leaders who had accumulated scars from lots of different battles.

Today, technology careers look very different. We have increasingly sophisticated specialisms in cloud, cybersecurity, data, AI, product, architecture, engineering, digital experience and platform operations. Those disciplines need deep expertise, and specialization has undoubtedly made technology organizations more professional. But there is an unintended consequence. Someone can now spend 10 or 15 years becoming extraordinarily good at one part of technology without ever really needing to understand how the whole organization works.

That’s not necessarily a problem for a specialist. It becomes a problem when we expect them to become an enterprise leader. Because the CIO job is moving in precisely the opposite direction.

CIO’s 2025 State of the CIO research found that 81% of IT leaders described themselves as change makers responsible for championing both business and technology initiatives. Seventy-seven percent said they had developed a strong educational partnership with the CEO and board.

That’s not describing an AI, cloud or cybersecurity specialist. It’s describing an enterprise leader.

Are we still developing CIOs for yesterday’s job?

I think there’s another problem. When organizations deliberately prepare people for technology leadership, much of the curriculum still reflects what we historically believed a CIO needed to know. Technology strategy. Architecture. Cybersecurity. Operating models. Cloud. Governance. Program delivery. Data.

Important? Absolutely. But increasingly they’re the entry ticket, not the differentiator.

Deloitte’s research into contemporary CIOs illustrates the shift. It contrasts the conventional CIO, technical expert and internal technology provider, with a contemporary leader expected to enable transformation, create topline value, take appropriate risks and influence business strategy.

The expectations keep expanding. Deloitte reported in late 2025 that 80% of technology executives surveyed said their roles had significantly expanded to meet business objectives, more than a third were managing a P&L, and 65% of CIOs reported directly to the CEO. That requires a very different development model.

The modern CIO needs to understand technology, certainly. But they also need to understand how their organization makes money. They need to understand a P&L, cash flow, capital allocation and investment cases. What the hell is EBITDA? Well, they should probably know.

I’ve come to realize that being a CIO is as much about everything outside technology as it is about technology itself. I need to understand customers. I need to be able to negotiate. I need to influence people over whom I have absolutely no authority. I need to know when to challenge the CEO, and when a particular hill simply isn’t worth dying on. I need to be able to walk into a board meeting and explain a complex technology risk without drowning everyone in acronyms, but equally without simplifying it to the point where it becomes meaningless.

Over the years, I’ve also had to understand acquisitions, regulation, geopolitics, organizational design, workforce transformation and commercial strategy. None of those things would once have been considered core technology disciplines. Today, I’d struggle to imagine being an effective CIO without understanding them.

And then, of course, AI arrived and somehow made an already broad job broader again. CIO.com recently reported that in more than 75% of enterprise CIO searches conducted by executive-search firm Caldwell, candidates are now expected to be “board ready”, able to engage directors strategically and speak the language of business leadership.

That phrase interests me. Because I’m not convinced you become “board ready” by completing a module on board communication and receiving a certificate. You become board-ready partly by accumulating enough experience to understand what the other people around that table are worried about.

We need to manufacture the breadth that careers no longer provide. This doesn’t mean recreating the career chaos of the past. I certainly wouldn’t advocate deliberately putting someone onto a failing transformation program for three years because it will be character-building. But we should recognize what those messy careers accidentally provided and deliberately recreate the useful parts.

My concern is that we’re becoming very good at helping future CIOs prove what they know, while the modern CIO role increasingly demands evidence of what they have done. Increasingly, I think the gaps in a future CIO’s experience may tell us more about their readiness than the certificates they’ve collected.

The question I ultimately want answered is simple: Have they experienced enough of the business to understand how the whole organization sees the world, not just how technology sees it?

If the answer is no, that’s where I’d start their development. Instead of building development primarily around knowledge, we should build much more of it around exposure.

That means deliberately engineering breadth rather than hoping someone picks it up along the way. If I were developing a potential CIO today, I might move them out of technology for a period and give them real responsibility in a business unit with a P&L; put them into a major transformation where success depends as much on people, customers and commercial decisions as it does on technology; and make them part of an acquisition from due diligence through integration. I’d want them negotiating a difficult supplier deal, defending an investment in front of the CFO and presenting to the board when the answer isn’t straightforward. These shouldn’t be observational placements or a week spent shadowing another executive. Give them something to own, decisions to make and consequences to live with. In other words, if modern careers no longer accidentally create breadth, organizations need to manufacture it deliberately.

Some of it can be taught. Much more of it has to be experienced. Technical depth remains enormously important. A CIO without sufficient technology understanding will struggle to challenge their organization intelligently.

Technical credibility and technical specialization aren’t the same thing

The CIO increasingly needs to be able to zoom out. Enough technical understanding to ask the difficult question of an architect. Enough financial understanding to challenge the business case. Enough commercial understanding to see the opportunity. Enough organizational understanding to recognize why the change might fail — and enough influence to bring everyone with them anyway.

Perhaps the accidental CIO wasn’t such an accident after all. We spent decades creating technology leaders through careers that were messy, unpredictable and broad. Now we’re creating clearer pathways, deeper specialisms and more structured professional development. That’s progress. But we should be careful not to optimize away the very experiences that made many of the previous generation effective.

The challenge isn’t to bring back the accidental CIO.

It’s to work out how to deliberately create the breadth that accident used to provide.