How do we teach our kids to respect authority but know when to disobey?

Isn't that question like an oxy moron?

When playing Black Jack, how do you know when to take a hit or stay?

I don't think you teach them to disobey ever. If you teach them right from wrong, they should intuitively know when to refuse a foolish request.

With mine, I have always given scenerios. Sometimes something on tv or something they've started dealing with will be the springboard. Sometimes, something will pop into my head. Or, I'll speak from my own experience. When I was a pre-teen, I was groped by an 80-something old guy. Ever since, I don't automatically respect my elders, like the folks say to, so I discussed that experience with them. And, what's okay for a teacher to say, what touches are okay, that even if on a date, if you first say "yes" to something, it's okay to take it back, etc.