Managers and most other people in business are pretty well accustomed to attending training sessions where they are asked to do strange things--fall on the ground, walk around in circles, etc. They are willing to do those things because they believe they will learn something in the process.
Where there is resistance, or I strongly suspect it will be there, I teach people to use index cards as a planning exercise and as a metaphor for planning. I tell them, "You may not be able to do this for your real projects, but let's investigate the benefits that would accrue if you could do it." They are generally willing to stretch the exercise to larger and larger (imaginary) projects, just to see what happens--a very ExtremeProgrammingish thing indeed. At the end, some of them will use index cards directly on real projects--usually the smaller ones that don't involve getting anyone else's approval.
For the other people and projects, index cards become a metaphor for a better way of doing things. By setting up the index card as a sort of ideal that cannot be reached--at least not in the cave of their current environment--they have a simple way to seek out improvements within their current planning approach. For example, from the cards they may learn to:
Cards as a metaphor is not nearly as good as real cards, so I don't do it if there is actually a chance of using cards themselves. But it's still a useful approach and a sneaky way to talk about something that might otherwise get shut down. It can even lead to doing the real thing once people start thinking about it.
-- CharliePoole