> I only generate skills _after_ I've worked through a problem with the model.

This is the correct way vast majority of the time. There are exceptions. When I know for certain that the models do not have enough training material on a new library or one that isn't often used or an internal tool. In those cases I know I will have struggle on my hand if I don't start out with a skill that teaches the model the basics of what it does not know. I then update the skill with more polish as we discover additional ways it can be improved. Any errors the model makes are used to improve existing skills or create new ones.