Matt raised the question in the comments to a previous post on how to teach thinking. I don’t think (no pun intended) there is an easy answer to that question and no single answer that works in all cases, e.g. Edward de Bono’s six thinking hats is a nice approach to encourage considering different sides of an issue, but is not going to work for a difficult rashi. There is definitely a need for someone to work out a systematic approach to teaching textual skills in the context of gemara learning, but until someone does that I don’t understand why schools ignore one fantastic resource already out there.
The master of a didactic method that emphasized thinking has to have been Nechama Leibowitz. This article summarizes some of her approach, and the gilyanot give a good flavor of her methodology. If it worked for chumash, why has no one applied the same principles to gemara? As an example, I want to focus on one method she popularized - asking “mah kashe l’Rashi”. Instead of emphasizing just being able to repeat what Rashi says (which is itself valuable, as there is no more canonical peirush than Rashi’s), the question of "mah kashe l'Rashi" shifts the focus to understanding and grappling with difficulties in the text. Instead of knowing what Rashi says, the emphasis is on knowing how Rashi thought. Why every time a student sees a Rashi on a piece of gemara are they not automatically trained to ask (even if they cannot always answer) the magic question of “mah kashe l’Rashi”?
I can cherry pick an example from what I was learning with my son a few nights ago: In Bava Kama 5a the gemara mentions the act of “mefagel” as a form of nezek. I asked my son what pigul meats and he remembered that it is the result of offering a korban with intent to eat it after the proper time. Rashi in B”K explains “mefagel” to mean offering a korban chatas with the intent for it to be a korban shelamim. Question: mah kashe l’Rashi that prompted redefining pigul?
(Note: for the sake of clarity I decided to break this long post in two - more examples to come).