Tag: Startup Leadership
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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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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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Over the past couple of years, I have had a few product people on my team, received coaching myself, and picked up a lot from conversations with other PMs, founders, and people who think deeply about building products. The contexts are always different. Different industries, team sizes, stages. But two patterns keep coming up with…