Operating Philosophy
13 essays on Operating Philosophy, from 25 years at the seam between the boardroom and the codebase.
Saying No to 1,000 Good Ideas
Focus doesn't mean rejecting bad ideas — those reject themselves. Part 4 of my product design philosophy: kill projects that miss the bar, prototype with working software, and restart when it isn't right.
Read →Nobody Asks for the Future
Customers describe their problems in the vocabulary of today's solutions. Part 3 of my product design philosophy: faster horses, seeing what others can't, and owning the parts of the stack that carry your vision.
Read →Start With the Experience, Then Work Backwards to the Technology
Design is not how it looks, it's how it works. Part 2 of my product design philosophy: the best interface is no interface, and the parts users can't see should be as beautiful as the parts they can.
Read →If Your Product Needs a Manual, the Design Already Failed
Simplicity is the ultimate sophistication. Part 1 of my product design philosophy: eliminate ruthlessly, question every assumption, and treat every "how do I…" as a bug report.
Read →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.
Read →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.
Read →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.
Read →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.
Read →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.
Read →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.
Read →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.
Read →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.
Read →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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