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CuSithBell comments on Plant Seeds of Rationality - Less Wrong
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I have a glimmer that humor can work well in this capacity.
For instance, jokes about pathological reasoning can induce the listener to consider why certain chains of logic are (horrifically) invalid (and thus humorous), and perhaps apply these lessons to their own reasoning.
(There is also the related but less pleasant phenomenon in which the listener immediately recognizes one of their own flaws as the butt of the joke (as embodied in an abstract joke-land entity as opposed to themselves), laughs in embarrassment, and decides to alter their behavior (or company) based on how their acquaintances view that character trait, opinion, etc.)
I posted an example from The Simpsons in a recent rationality quote topic because that show occasionally hits this sort of humor right on the nose - I used "They did it because they're stupid, that's why everybody does everything", but a similar situation occurs when Homer's caught in traffic and says "Don't worry, I have a secret weapon!" before starting to honk his horn furiously.
Such stories are used by Idries Shah in many of his books for precisely this purpose.
Quite intriguing! Can you suggest any of his books in particular as a good place to start?
To suddenly discover Idries Shah is a bit like discovering the Sequences: there is so much.
I'd suggest The Magic Monastery (subtitled "Analogical and Action Philosophy of the Middle East and Central Asia"), which is a mixture of traditional teaching stories and stories of his own composition.
Then there are the books of Nasruddin stories (see the biblio at the end of the wiki article). Nasruddin is a traditional figure in stories all over the Middle East, and you can find a lot of Nasruddin stories on Google.
Shah's books are available in the US from ISHK and in the UK from Octagon. From places like Amazon too, of course, but the publishers' sites collect everything together more conveniently.
Hah! I'll have to check him out. I took a course on "Islamicate" literature and philosophy semi-recently, and found Sufism very interesting. Almost did my final paper on The Conference of the Birds (though the library's translation was ancient, called Muslims "Muselmen"). Thanks! :D