Dan Maccarone, product strategist and co-founder of the design studio Charming Robot, draws a line between what expertise can be documented and what must still be learned through first-hand experience:

The move nobody makes: run both plays on purpose. Structure what you can, and still teach it to a person.

The trap is thinking you have to choose between them like my co-founder clients. But you don’t. The better move is to run both plays at once, on purpose: write down everything about your judgment that will survive being written down, and build the apprenticeship for everything that won’t.

Start with the writing-down, because there’s a catch everyone hits. Getting your judgment out of your head isn’t the same as dumping your files into Claude. Do that and you get mush. The model grabs the loudest thing you’ve ever said and hands it back with total confidence.

In design, AI guardrails can store the reasoning, conditions, and exceptions behind a product decision. Apprenticeship gives people decisions in context through critique and design reviews, where correction becomes pattern recognition. Reading the expert’s answer is not the same as learning how to arrive at one.

Trust it like you’d trust a very sharp new hire who’s read everything and lived nothing: useful, fast, and occasionally, cheerfully, wrong.

Maccarone’s prescription is to document the method and pair it with apprenticeship, so people learn when to use their own judgement.