One nice way to do this might be to wait until EY releases The Art of Rationality, and then the LW community could develop a workbook of exercises and sample problems to go along with it. In many cases, the sample problems could be borrowed from textbooks on, for example, probability theory.
Very good suggestion. I'd read him mention writing a book. Maybe if he sees this post he'll be reminded that young Padawans are waiting in eager anticipation. And, yes, if LW-ers could put together a nice workbook to go along with it, that would be fantastic.
Note: This was originally posted in the discussion area, but motions to move it to the top level were made.
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My own desire to improve my rationality coupled with some posts criticizing LessWrong not too long ago led to an idea. For reference, the posts I mean are these: