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Field notes on enterprise program leadership
Lessons from hospital cutovers, M&A integrations, and programs with seven-figure stakes, written from the war room rather than the whiteboard. New posts most Tuesdays.
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I Helped Build Windows Update. Here’s What That Taught Me About Scale.
What building Windows Update at Microsoft taught me about scale: write the playbook, design for contained failure, and treat documentation as infrastructure.
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Compliance Isn’t a Phase. It’s the Program.
A lot of technical programs treat security and compliance like a gate. You build the thing, hand it to the security team, and wait to find out what…
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The Day We Had 12 Hours to Move a Hospital (and Why That Was the Easy Part)
People ask me sometimes what the hardest part of a hospital IT migration is, especially when you’re moving an entire hospital’s IT infrastructure. The honest answer is: not…
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$1.5 Million a Day Gets People’s Attention. Here’s What I Did With It.
There are moments in a program management career, usually when you have to reduce downtime that’s costing real money, where the numbers stop being abstract and start being…
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Translating Technical Risk into Executive Decisions
Here’s a situation I’ve been in more times than I can count, and it’s the heart of translating technical risk into executive decisions. An engineering team surfaces a…
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Enterprise M&A Integration: Where Technical Programs Succeed or Stall
M&A integration is one of the most reliably underestimated programs in enterprise IT. The deal gets announced. The press release goes out. Everyone is optimistic. And then the…
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Dependency Mapping at Scale: Where Enterprise Programs Actually Break
Enterprise programs rarely fail because of lack of effort. More often, dependency mapping stopped short. They fail because dependencies were misunderstood, assumed, or surfaced too late to influence…
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Designing Enterprise Cutovers That Don’t Fail
Enterprise cutovers rarely fail because of a single technical error. They fail because risk accumulates quietly — in untested rollback paths, assumed dependencies, incomplete rehearsal, and optimism masquerading…
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What Senior Technical Program Managers Actually Do
Let me tell you how most people describe my job when they hear the title “senior technical program manager.” “Oh, so you run meetings and make sure everyone’s…