Another kind of Plan
This idea about planning is from the comments on Robin Law's journal:
My current method is that the players tell me their plan, including inventing all sorts of details about how they think the enemy operates. They tell me what abilities they're using in terms of advance intelligence, tactics, knowing the area, having useful contacts, and so on. Then I roll to see how well they did (and don't tell them the result): and the better they succeeded, the closer their assessment of the situation is to reality. If I know they're making some major false assumptions, I'll put some minuses on the roll, but to a great extent, they get to design the opposition so as to showcase whatever aspect of their PCs they want to showcase.
Of course, this does require a certain degree of flexibility on my part.
Comments? Would you like to run it this way when, for example, assaulting the Tunneled Hills?
We tried this
I think our attempt to do this was when our characters went after the portly red scholar in order to retreive a string from the New City and we know how that went. We assumed a lot about our target (the resistance) and we either made many false assumptions or it was just a poor grasp of the plan that caused disaster. Either way, our plans can reflect this approach if it enhances the story. It is strategic thinking. Is any character a tactician?
Is any character a tactician?
Unless you mean the tactics of cavalry battles, then no, not by tendency. In terms of skills though, Rasa seems to have some skills that could be of tactical use. As does, arguably, Will.