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There is a Buddhist idea that has lived in my head for decades now. The image is simple: a teacher raises their finger to point at the moon. The student stares intently... at the finger.

The teaching isn't about the finger. The finger is pointing at something. But the student, eager and well-intentioned, has confused the pointer with the thing being pointed at. They are...


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There's a thread on Hacker News asking what breaks first when an engineering team grows from 10 to 50 people. The answers are predictable: documentation, communication overhead, tribal knowledge, early hires having identity crises. All tru...


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The Cone of Uncertainty, Fibonacci scale, and Cynefin walk into a sprint planning session...

A product manager walked into a refinement session a few years back, dropped a one-pager on the table, and said: "How long will this take?" The team I was leading had been through enough of these moments to know the ritual. Someone would say a number. That number would get wri...


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A few years ago I was convinced we had a delivery problem. The evidence was everywhere. Features took weeks longer than estimated. The team was visibly busy, always in motion, always context-switching. Sprint reviews felt like triage sessions. My instinct was to look at the board, find where work was piling up, and fix that stage in the pipeline. I identified a bottleneck in ...


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Most engineering managers I’ve worked with have the same problem, and it’s not the one they think.

They think they need to coach more. They’ve read the books, attended the workshops, internalized the message that great managers ask questions instead of giving answers. They’ve been told, repeatedly, by people they respect, that their job is to “unlock potential” and “emp...


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