Topic

Operating Philosophy

9 essays on Operating Philosophy, from 25 years at the seam between the boardroom and the codebase.

Operating PhilosophyMay 2026 · 6m

Find the Bottleneck Before You Automate Anything

Automating around a constraint just moves it somewhere worse. Find the real bottleneck first, fix ownership, and most of the tooling you were about to buy turns out to be optional.

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Operating PhilosophyApr 2026 · 7m

Support Is a System

Support isn't two help desks bolted to the side of the org, it's one feedback loop. Run it as a system, instrument the right KPIs, and it pays back in product and ops fixes, not faster ticket-closing.

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Operating PhilosophyApr 2026 · 6m

Aligning Technology With the People Who Aren't in Engineering

The hardest part of a technology org isn't the code. It's keeping it pointed at what operations, product, and the business actually need.

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Operating PhilosophyMar 2026 · 6m

Protecting the Roadmap Without Becoming the Department of No

Staying responsive to the business without letting every urgent request shred the roadmap. How to say no without becoming the department of no.

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Operating PhilosophyFeb 2026 · 6m

Prioritization Is the Job

A technology leader's real work isn't deciding what to build. It's deciding what not to build, and holding that line against the pull of every loud request.

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Operating PhilosophyFeb 2026 · 6m

Vision Is Cheap. Execution With Accountability Is the Whole Game.

Anyone can paint a future. The job is closing the gap between the vision and the shipped thing, and owning the result either way. Here's what that takes.

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Operating PhilosophyJan 2026 · 6m

Planning Season Without the Theater

Quarterly and annual planning is where most tech roadmaps quietly drift from what the business actually needs. Here's how I keep the plan honest, sequenced, and tied to the numbers leadership cares about.

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Operating PhilosophyMay 2025 · 4m

Business Before Backlog

Most roadmaps are a pile of features looking for a reason. The fix is to start from the product and the P&L, then build the engineering to match.

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Operating PhilosophyMay 2025 · 4m

Read the Thesis Before the Code

Architecture is a means, not an end. Before I judge a system, I learn what the business is trying to become.

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