Category: Field Note
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A generalist we hired early ended up doing several jobs under one title, and the debate about it went in circles. Writing the job description again, years after hiring, turned a stuck title discussion into a package both sides could negotiate.
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AI agents are great at gathering context for 1:1s and coaching prep. But the judgment stays human. Here is the line between errand and judgment.
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Turning how your best people work into an AI Skill sounds like a documentation job. It isn’t. The hard part is judgment, and the moment you try to write it down you hit a forty-year-old problem that AI has quietly moved rather than solved: the work is no longer getting the knowledge out, it is…
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We’re a small company selling into a narrow, heavily regulated market. There are maybe a few dozen buyers that really matter, and most of them are cautious about anything new. For a long time I treated getting our first real customers as a search problem. Looking at where those customers actually came from, I realized…
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Structured learning programs felt like real development. The team kept reaching for short courses and coaching instead, and they were mostly right. A note on the founder’s time horizon, and what AI changes about it.
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We thought our onboarding developed people. Mostly we hired self-starters and paid for external coaches. A note on misattribution.