I thought that Socratic questioning was designed to take care of this problem, some 2500 years ago.
Socratic questioning can certainly fall prey to the illusion of transparency; when you know what conclusion you're trying to reach, it can cause you to overestimate how obvious the answers to the questions in each step are, or close your mind to other possible answers to the questions. I've had some people try to use it on me when I was younger, and they were sometimes very frustrated with the results.
It is certainly much harder to use than declarative teaching, as you have to model your pupil's mind so you can tailor the questions appropriately. And it takes longer and more effort to present the same material. Thus it is completely unsuitable for, say, public schools.
If the model is wrong, Socratic questioning fails spectacularly: "I don't understand what you are asking!" "That's because you are stupid!" Or worse, it can degenerate into guessing the teacher's password, with neither side the wiser. I presume that is what you mean by "falling prey to the illusion of transparency".
However, when done right (and EY is certainly a prime candidate for doing it right), it leads to a deeper understanding of the issue by both sides, precisely because of these "other possible answers".
Or maybe I am falling prey to the positive bias.
Today's post, Double Illusion of Transparency was originally published on 24 October 2007. A summary (taken from the LW wiki):
In addition to the difficulties encountered in trying to explain something so that your audience understands it, there are other problems associated in learning whether or not you have explained something properly. If you read your intended meaning into whatever your listener says in response, you may think that they understand a concept, when in fact they are simply rephrasing whatever it was you actually said.
Discuss the post here (rather than in the comments to the original post).
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