gjm comments on Dangers of steelmanning / principle of charity - Less Wrong
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Issue 1 above has nothing to do with losing sight of how incompetent our civilization and most of its individuals are. It's about almost the opposite problem: trying to be charitable to someone else by adjusting their position to be more like your own, at the risk of messing it up in the process.
[EDITED because I wrote "Issue 2" where I meant "Issue 1", and also to fix up a minor consistency arising from the fact that an earlier draft had had "Issues 1 and 2".]