Field-tested essays from twenty-five years in enterprise technology leadership — on governance, culture, judgment, succession, and what it means to lead responsibly as artificial intelligence reshapes the enterprise.
Strong technology leadership depends as much on stewardship, governance, and trust as it does on delivering successful transformation. The real test of a CIO isn't what happens while you're in the seat — it's whether the organization keeps running well once you're gone. This piece walks through what it means to build systems instead of dependence, and why the best leaders deliberately make themselves less necessary over time.
When electricity reached factories in the late 1800s, it took thirty years to show up in the productivity numbers, because leaders simply bolted a motor where the steam engine used to be. AI is running the same test on every organization today, and the winners will be the leaders who redesign the work, not just the ones who buy the license.
Roughly three out of four employees who use AI at work are already bringing their own tools to the job, often without telling anyone. Banning it doesn't remove the risk — it just blinds you to it. Here's the leadership playbook for bringing that usage into the open, safely.
Zillow's home-buying algorithm did exactly what models do: math, at speed, on the past. What failed was the human decision system around it. A look at the judgment advantage every leader needs when AI hands you confident recommendations in bulk.
When Air Canada argued its chatbot was "a separate legal entity," a tribunal disagreed in the plainest possible terms: when your AI acts, it is you acting. A practical look at building the trust account every responsible AI program depends on.
I transitioned from accounting into information technology during the Y2K era, when the deadline was set by the calendar itself. Twenty-five years, one layoff, and several turnarounds later, here's what that first crisis still teaches me today.
Both of my books expand on these ideas in full — one on governance and stewardship, the other on leading through the age of AI. Available in Hardcover, Paperback & Kindle.
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