_Proofs and Refutations_ tops the list. Dialog and progressive discovery are crucial to solving problems, and these things happen even after (mostly after?) you arrive at a good solution. _P&R_ provides a working example of how this might go, and how a diligent and magnanimous mind might approach the process. I think it's a really fun and engaging book, too. Works on pragmatism by CS Peirce were really impactful, though I can't recommend a specific book. In a very focused way, Peirce advocates for evaluating ideas in terms of their real-world effects, often by employing a measured skepticism. On the psych/behavioral side, _Gut Feelings_ shows how to be an efficient thinker. Largely contrary to Kahneman's work, it vindicates intuition, but does so in a qualified way. It explains when and how to trust your instincts, and emphasizes the importance of cultivating them.
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