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For the past two years, the loudest debates inside our company have used the same vocabulary: scale, productivity, AI. Every quarter delivered a fresh version of the same conversation. How do we scale sales? How do we make customer success more productive? Which AI tool takes which workload off whose desk? The vocabulary came from…
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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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Around the third report a team lead’s job changes. We treated it as a coaching problem, not a ceiling, and our player-coaches learned to run teams of four or five.
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An enterprise customer we had built toward for months backed out, late and without warning. The gut punch lasted twenty minutes. What mattered was the next few hours: what we told a team of forty, and in what order. Here is the playbook, and where we went off script.
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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.
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Generative AI was supposed to clear the fog inside organizations. It produced a new one: five layers of opacity that the old management tools cannot navigate.