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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.
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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…
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Most people who work in product development agree that it is essential to understand key problems in order to build good solutions. This often involves understanding the customer or finding new products. It has also become common for engineers, who are responsible for building the product, to be involved from the start. This is explained…
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In my last blog post, “The Framework Trap,” I talked about all the problems we ran into when engineers, designers, and product team members were working together. I’ve come to see that Scrum, with its strong emphasis on the right processes, has actually been more of a hindrance than a help to our team. While…
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When we started working on our products, especially our software, we had a pretty inexperienced team. Some of us had already worked on software projects at other companies or participated in research projects at universities or research institutions. The team’s most experienced member, in terms of years of professional experience, was a software engineer with…