There's listening, then there's listening. When someone is really learning, you are dealing with the edges of their model of the world and their conscious perception. When you are really teaching, you are playing in this dangerous interstice. Sometimes, the best way of teaching people is tricking them. Sometimes, if you just tell them, they'll just rationalize what you have to tell them away.

This is more apt to apply to classes in history than to computers, however. Even then, there are popular misconceptions to deal with.

Trick the mind, not the person. Symbolism may convey something you can't understand through normal conversation.