The Hidden Risks of Shadow IT
Timothy Chester explores the realities of shadow IT through a recent CIO interview experience. This episode delves into why shadow IT forms, its persistence, and what it reveals about executive leadership and organizational priorities.
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Chapter 1
Introduction
Timothy Chester
A colleague recently interviewed for a high-profile CIO role. The opportunity looked promising, but when they interviewed, red flags emerged. The hiring executive had created a shadow IT unit, tasked with using AI to deliver much-desired efficiencies. The leader of this team, like any “star quarterback,” was confident, opinionated, and clearly had the full trust of the executive. But he showed less concern for the IT organization, enterprise architecture, or long-term support
Timothy Chester
After meeting this superstar, my friend called me to talk it through. I said plainly, “It sounds like he’s the real CIO, without the responsibility of being one. No governance, no need to deliver resilient systems. Just build fast and impress the boss.” That was all they needed to hear. They withdrew from the search.
Timothy Chester
In today’s Dispatch, we discuss shadow IT. Not just how it forms, but why it persists and what it reveals about those who enable it. It is a recurring symptom of poor leadership foresight, shallow governance, and executives chasing quick wins at the expense of resilience.