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Why do you have a debugging skill? Just tell it to read the docs.

Skills are for packaging instructions for how to interact with your organizations homebrew process and tools. By definition skills shouldn’t be useful outside of your org because they’re just docs and third party tools already have them for humans.

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You don't. If you're using skills to force the AI to fullfill some must criterias, it's not going to work. Must criterias need deterministic checks -> be it hooks or what not.

This is also my biggest gripe with AI. I.e. for specifications, no matter what hype machine I tried, it never fulfilled my criterias, which are: easily verifiable, concise, small specs. Hence I built https://github.com/RicardoMonteiroSimoes/Yamlet initially for claude code, but then decided to use extend it for pi.dev. I now have a dedicated docker image for pi.dev, that only contains Yamlet plugin, and whenever I work on spec I spin it up.

The end result is a .yaml file that easily works in git + git diff, so that I can then proceed with the technical specs-

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A skill should only document behaviour the LLM didn't/couldn't exhibit on its own.

So you take your failed case (eg. working with gdb or whatever), write a skill and then test for that failed case.

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There are also skills that help LLM do the thing it can do without the skill, but faster (by cutting out unnecessary discovery). I guess for such skills the fail case is "being slow"?

I imagine many fail cases can burn a lot of tokens/usage/time because failing LLMs can be very persistent. Maybe some upper bound (turn count, timeout) would help too.

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