Weekly Recap: ”Will I Still Matter at 66?”
Why the next ten years of IT leadership will be more about people than technology.
Recently, my commentary “Will I Still Matter When I’m 66?” was published by EDUCAUSE Review, a long-planned response to Greg Jackson’s 2004 essay, “Will You Still Need Me When I’m 64?” Jackson was one of my profession’s giants, and his views shaped how I approached my first CIO role. Now, I’ve written my own vision for the next decade of IT leadership.
Why it matters
Two decades ago, Greg Jackson posed a deceptively simple question that lodged itself into the minds of many IT leaders, especially me: “Will you still need me when I’m sixty-four?” It was never really about aging; it was about relevance. About whether CIOs would still matter to higher ed once infrastructure faded into the background.
Last week, I returned to that question as a provocation for the next ten years.
The Leadership Pivot
The role of the CIO has always been shaped by disruption: the Internet, mobile, cloud, and now artificial intelligence. But something deeper is shifting. We’re no longer just translating technology into strategy. We’re being asked to help institutions navigate ambiguity itself: to guide, steady, and connect in an age where stability feels scarce.
Relevance now depends less on how well we manage tools, and more on how thoroughly we prepare others to lead when we’re not in the room with them.
The Shift: From Execution to Meaning
In the EDUCAUSE Review piece, I argue that the most important CIO work for the decade ahead is not technical execution, but cultural leadership. That includes:
Simplifying work: Institutions are still tangled in layers of legacy logic. The CIO’s job is to cut through that, not by automating bad processes, but by streamlining with empathy and intent. Simplicity isn’t efficiency. It’s clarity.
Protecting the institution: Cybersecurity has moved beyond infrastructure. It now lives at the intersection of trust, reputation, and readiness. CIOs must show up as calm voices in a chaotic environment, earning credibility as much as deploying controls.
Making data useful: Most campuses don’t lack data. They lack shared insight. CIOs must build systems that make meaning possible and cultivate cultures where better questions, not just better dashboards, drive decision-making.
Connecting the ecosystem: In a world of cloud sprawl and third-party tools, integration is no longer about connecting systems; it’s about aligning people, purposes, and platforms. It’s institutional sense-making of the highest order.
Driving adoption that sticks: Too many tech projects end at go-live. CIOs must stay with the work, ensuring that tools are trusted, embedded, and continuously refined through feedback. The goal is not installation, it’s continual impact.
The article reflects on what it means to lead when leadership itself is under pressure. Pandemic response, AI acceleration, and economic strain have exposed whether IT teams were truly aligned with people and mission, or just managing mechanics.
When leadership is grounded in moral clarity and shared trust, our teams are capable of responding not with panic, but with presence. That’s what matters now.
The final word
The infrastructure footprint may shrink, but the leadership footprint is expanding. The most consequential CIOs will be the ones who:
Help others make sense of complexity.
Build teams that quietly become indispensable.
Prepare their institutions not just to survive disruption, but to thrive despite it.
Jackson’s question remains. But the answer no longer hinges on what we do. It rests on how we lead. In a world where tools evolve faster than trust, the real legacy of a CIO isn’t the platforms deployed or the contracts negotiated. It’s the teams and cultures we leave behind: ones that can adapt, align, and thrive long after we’re gone.
That’s what it means to matter now.