FiftyTwo comments on Best articles to link to when introducing someone to Less Wrong? - Less Wrong Discussion
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You're probably correct in your first point, I should introspect on why my first instinct was to manage their experience myself. I am concerned that a randomly selected article might put them off for the reasons I mentioned above.
Your second suggestion is likely to be extremely effective from the sounds of it. I wouldn't worry about the dark arts elements, if we are finding areas they are interested in already, and they are already rationalist-ish they will likely agree with the main points anyway, and be impressed by the overall structure.