May 26, 2026
Most teams, the moment they decide to build something serious with AI, reach for the ritual they already know: the offsite, slides full of confidently drawn boxes and arrows, a roadmap with quarters marching across the bottom, and then the reorg to deliver it. Draw the destination, point the organization at it, march. It’s a familiar ritual – it’s worked for most of the things we’ve ever built – but pointed at AI, it runs almost exactly backwards.
The reason is what Ethan Mollick named the “Jagged Frontier.” The capability surface of LLMs is wildly uneven, and you cannot read its shape from the outside – the AI model nails the task you assumed was hard and fails miserably on the…
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