Ask HN: How to rephrase or tweak bad questions?

I've noticed that PG in his essays solves a difficult question by transforming it, e.g see http://paulgraham.com/hubs.html (3rd paragraph) and http://www.paulgraham.com/nerds.html (6th paragraph). So transforming questions yields much better answers. Any advice on how to develop this skill? Can you point to some principles or recommend some books?