Chess and go both teach you to think ahead like that, othello, checkers and other strategy games to less extent. Then take that, and run through what can happen. "Roleplaying", "sandtable exercise", whatever you want to call it, it is all "what if". If X happens, the likely outcomes are Xa, Xb, Xc... Xn. What are the likely outcomes of those. Work out what variations there might be. Then take problem Y.

Sounds like a pain in the butt. But once you start it, it turns into habit. For example, you don't think about all the things that can go wrong in a building, just that most of them involve getting out, so before long you are looking for conventional and unconventional ways out of every room as you walk in and drawing a map in your head back to the front door and to all the various exits.

*shrugs* At least that's how it works for me. My head is like a filing cabinet full of folders within folders, right down to "are the hostile alien invaders using directed energy weapons or kinetic energy weapons for their personal arms?" *grins*