A small thought: I came up with another place where different modes of thought
result in different approaches -- namely, the preparation of setting material.
For Guardian mode, you wouldn't want too much pre-planned detail, because it might interfere with the desired fluidity and symbolism of game play. It would probably help, though, to have some ideas regarding who are the (good) insiders and (bad) outsiders.
For Warrior mode, it would be important to establish what sorts of power you can have and what sorts of opposition you'll face. That probably means you'll want lots of flavorful options for cool characters, and similarly flavorful villains, monsters, or rival organizations.
For Manager mode, you'd want to make sure you've detailed the established order -- societies, social institutions, cultural norms. It's important to have fairly well fleshed out both which things are right and which are wrong, and the social context in which those decisions happen.
For Strategist mode, the setting material needs to make clear what's possible and what isn't within the imagined world. That is to say, if you're playing in a modern setting, and a magic wand shows up without some indication that this is possible, it's likely to break Strategist mode fun. For this mode, it's also likely to be important that setting material interacts strongly with the strategic possibilities -- for most games, that'll mean the mechanics.
For Radical mode, I think you'd want setting materials that were suggestive and evocative but open to reinterpretation. Probably also setting materials that present multiple perspectives on people, cultures, places, and so forth.
It strikes me that if you look at the setting material presented in a book, you might be able to get a pretty good idea of which kind of fun it's trying to create. For example, if you look at most D&D books, you'll find materials that are pretty close to how I described Warrior and Strategist modes. Lots of cool abilities and character types welded to lots of crunchy mechanical bits.
A related data point: A friend of mine has a pretty strong preference for Manager mode play. While he does often end up playing D&D, his fun really doesn't have much to do with either the crunchy stuff or being powerful. His favorite d20 game: Wheel of Time, where the setting has all kinds of cultural detail, as well as a strong right/wrong dynamic.
I'm sure you can expand on some of those pictures, especially if they're the ones you like best. What have I left out? Which strategies do you find helpful for prepping materials for each of these modes?