7 posts across Directing AI, Judging AI
Four separate stories this year — a CEO's warning, a viral study, a blunt writing rule, a $50,000 gap in financial advice — all point at the same three seams. Here's the throughline, and the move that closes each one.
4 min readSimon Willison endorsed a rule blunt enough to actually follow: write it yourself, then use AI only to flag problems, never to supply the fix. Two studies published the same week explain why the line matters more than it sounds.
4 min readThe useful question isn't whether writers should use AI. It's which stage of writing to hand over — because handing over the wrong one costs you the thing people are paying for.
5 min readOpenAI's Tax AI demo showed what happens when accountant corrections become structured feedback that measurably improves the agent. The reviewing skill most AI training skips isn't 'check the output' — it's how precisely you flag what went wrong.
4 min readFigma's CEO Dylan Field told Stratechery that AI output 'draws from the middle of the distribution' — and that teams become viscerally attached to their first concept. The iterate-and-refine skill is what separates competent AI output from distinctive work.
4 min readAnthropic's analysis of 639,000 conversations found sycophancy doubles when users push back. What that means for anyone relying on AI as a second opinion.
5 min readAI drafts fast and defaults to generic. For anyone whose job is being heard, that's a real risk. Here's how to use it for speed without your writing converging on everyone else's.
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