I've been reading Sun Tzu's The Art of War, and I'm finding it a great help in thinking strategically. I tried the chess thing, but I don't have anyone to play with, so that didn't go too far.
By strategically, I assume that you mean how to turn a general direction into a set of steps. Here's another way to do it that may help:
- Describe a character's direction, and how you'd know if it got there. (e.g. Sir Ronald Bravelock wants to discover the killer of Lord Fairbright, his liege. He'll know that he's got the killer if he obtains a confession)
- Describe what's impeding getting there (E.g. Sir Ronald has no idea who the killer might be, he's never tried to find a murderer before, would have no idea how to make him confess if he did find him, and his wife Lady Bravelock is heavily pregnant and being very demanding)
- List what assets and resources the character can bring to bear. (E.g. While normally meek, Sir Ronald is prone to fits of passion that make him incredibly strong -- especially when he sees bullying. He has a loyal friend Squire Gimley who's cynical but a good judge of character. The local herbalist Dame Trot has a crush on him and would do anything for him)
- For each impediment, see if you can create a Situation of Opportunity in which the character can overcome one of his impediments. (E.g. while Sir Ronald has no idea how to find a killer, Dame Trot is a fund of wise folklore and might have some advice)
- For each Opportunity, see if you can create a Condition of Threat to make it difficult to realise the opportunity (E.g. Lady Bravelock is the jealous type and her pregnancy has made her paranoid. If she gets whiff of Sir Ronald visiting Dame Trot, she'll hit the roof)
- For each Opportunity and Threat, see if you can construct a scene that resolves them. The resolution of the scene might either achieve the goal or fail. In reaching that outcome, it might add more complications or add no complications. Wherever there's a failure or complications, see what Opportunities can correct them, and what Threats can make them worse. Then you can try to construct another scene to resolve them.
- As the plot progresses update the character's Assets, Resources and Impediments as these will change. This will result in changes to Opportunities and Threats.
Now imagine that the killer (Duke Blackheart) learns that Sir Ronald is after him. He too has a Goal (get away with murder) with Recognition (Sir Ronald dies, gives up, or punishes the wrong person), and Impediments and Assets and Resources. Now you have a game of chess. As Sir Ronald gains Assets and Resources, the Impediments to Duke Blackheart increase. He'll want to capture/kill/neutralise Sir Ronald's Assets and Resources. As Sir Ronald gains information, the Threat to Duke Blackheart increases. As Duke Blackheart finds ways to threaten or confuse Sir Ronald, his Opportunities increase.
This approach uses strategic analysis to help develop plot. The analysis is called a
SWOT analysis, because it lists Strengths, Weaknesses, Opportunities and Threats. That's the same stuff that Sun Tzu talks about, but he also offers advice how to limit your weaknesses, capitalise on your strengths, pursue opportunities and avoid threats. For fictional purposes it can be just as interesting to
ignore Sun Tzu's advice as to take it.
Hope that helps.