Tactical, Operational, Strategic--Planning is Different for Each

At the tactical level, one is concrete and particular, and complex planning with what-if's is possible--although you know that invention on the part of the actors will be required.

Operational and strategic levels do not deal with many contingencies, except when things go big awry. Then you go back to the drawing board, so to speak. The Colonels' and Generals' planning teams have to think differently than does the Captain and Major, who are often tactical.

What the Operational and Strategic have to do is to figure out big goals and how to go about it. I think of arguments toward the end of WWII about whether to go to Germany directly or in a pincer. I am surely getting this wrong, since my memory for such details is likely fuzzy. But the point is that Eisenhower made a choice  and all else followed. If it did not work out, presumably they had to think about what next.

The complexity planners face is in part that the other side (or the customers, in business) has their own agenda, may act surprisingly (even as they think of themselves), etc. So the question becomes whether one's judgment is mildly reliable, and whether you have enough feedback and agility to know and deal with reverses. To use my current hobby horse, Rumsfeld got lots of feedback, but he had little of the requisite agility (or so the historical record seems to show--it may be wrong). Pride is useful in forcing one to persevere, but it is disastrous when one has to acknowledge things are not going your way. Strength lies in taking that disappointment and dealing with what needs to be done next. That is, do you have an ability to either have backup plans, or to generate them, when they might be needed. That's real strength.