Is it possible to develop a set of meta-thinking skills that help us execute or create Less Wrong meta-thinking skills?

Here's a simple meta-thinking skill that aims at this: recursively ask yourself "How could I have thought of that?".

I've been playing with this in the context of solving math problems. I'll work on a problem for a set amount of time and then look at it's solution. I'll then think back to the thinking I did, and figure out what kind of meta-skill or meta-heuristic would have allowed me to make it to the next step of the solution. And so on, until the end of the solution if possible.