I often say to Claude "you're doing X when I want Y, how can I get you to follow the Y path without fail" and Claude will respond with "Edit my claude.md to include the following" which I then ask Claude to do.

Not sure this is a great idea. The model only internalized what it was trained on and writing prompts/context for itself isn't part of that. I try to keep my context as clean as possible, mostly today's models seem smart/aligned enough to be steered by a couple of keywords.

Ah yea I do that too. I often have reflection sessions with Claude where I ask it "how can I make sure you do behavior X so we get outcome Y?"

It works relatively well but not always.