The current tooling isn't aggressive enough in that it's not the first thing that the agent checks for when it is prompted, at least for claude code. Way more often than not, i remind the agent that the skill exists before it does anything. It's very rare that it will pick a skill unprompted. Which to me kind of defeats the purpose of skills, I mean if I have to tell the thing to go look somewhere, I'll just make any old document folder in any format and tell it to look there.