gwern comments on 11 Less Wrong Articles I Probably Will Never Have Time to Write - Less Wrong
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While we're listing stuff, one thing I'd like to do at some point would be to look at the literature on philosophical training and critical thinking ability (eg. as measured by the Watson-Glaser test). http://images.austhink.com/pdf/Claudia-Alvarez-thesis.pdf looks like it's the best current starting point.
EDIT: I wound up excerpting that thesis at length: http://lesswrong.com/lw/dhe/to_learn_critical_thinking_study_critical_thinking/
Also: Are philosophers expert intuiters?