JGWeissman comments on 3 Levels of Rationality Verification - Less Wrong
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Good rationalists, taken as a group, shouldn't be systematically optimistic.
Perhaps we can still test for this systematic optimism, while filtering for the noise I objected to, by instead of asking a "yes" or "no" question, asking for the probability that the student is in the top 50%. Treat the sum of these probabilities as the count of "yes" answers in the original version. Then a rational student should be able to account for his ignorance of other students in his answer.
This is even easier to game: assuming the school has any merit, any individual you ask should have good incentive to simply say "50%" guaranteeing a perfect score. The very first time you used the test it might be okay, but only if nobody knew that the school's reputation was at stake.