Field Notes
Notes from the work — technical alignment, vCIO strategy, systems thinking, and leadership. No theory I haven't run in the field.
Leadership
For a while I optimized for momentum and assumed the results would speak for themselves. They don't. Strategic work that nobody can see is the easiest thing in the building to pause.
2026
Systems Thinking
I built an assessment with 110 questions in it. The only complaint was that it takes too long. That's a scheduling problem, not a reason to skip the understanding — and you can't make good long-term decisions for a business you don't understand.
2026
vCIO / Technical Alignment
An engineer sees a server at end of life and reaches for the answer they've been rewarded for their whole career: replace it. But a newer server hosting the same problem doesn't remove a single support ticket. It just resets the clock on the same liability.
2026
vCIO / Technical Alignment
Most vCIOs are measured by the size of the projects they put in front of a client. By that scoreboard, one of the best things I scoped recently was a failure: it cost nothing. That gap is the whole problem with how the role usually works.
2026
Systems Thinking
I used to run three teams of ten engineers. We hit our KPIs. Then the organization shifted and I watched it all fall apart. Not because the people got worse. Because decisions were being made on vibes instead of a framework.
2026
vCIO / Technical Alignment
Most vCIOs are operating from one of two places: engineering lifecycle refresh thinking or sales quotas. The problem goes deeper than incentive misalignment. It starts with how the role thinks about clients.
2026
Leadership
Everyone says hire people better than you. The part nobody unpacks is what "better" actually means, because the advice stops making sense the moment you expect it to mean better across the board.
2026
AI / MSP Strategy
Everyone in the MSP space is either selling AI or hiding from it right now. Both camps are making the same mistake.
2026