For example my goal for the Fall 2010 season was to perform a rich "Organic" Harold by December. Here was my general approach:
- Aug. Work on rich character development and perform the Henry
- Sept. Work on strong relationships within a scene
- Oct. Work on recognizing and continuing themes throughout a set of scenes and introduce the Harold
As you can see the general flow is building to the "Organic" Harold, as well as focusing on all of the important elements of good improvisational scenes.
However you can't stay rigidly die hard to your general outline. Your troupe is a living breathing creature and doesn't always progress at the speed that you expect. You can't be afraid to redo a workshop if your troupe didn't comprehend it fully the first time, and that being said you can't be afraid to scrap a workshop if your troupe is really good at the involved material.
Also make sure there is some time for your troupe to just play. Think of it as a scrimmage. Practice doesn't make sense until you play the game. Another thing is create workshops that are specific to your troupe. If your troupe has trouble developing interesting dynamic characters really dig in there and try to find the specific inhibitor and then workshop to remove it.
The last thing, and I think it is the most important thing in this post, is don't reinvent the wheel when you're running a workshop. That's not to say don't be original or creative in your approach, but keep it simple. I have been to a few workshops by really talented improvisers that were just confusing and not helpful because they were trying to be super clever in their delivery, when all they needed to do was let it happen. Keep it simple, keep it focused, keep it fun. Boom!