The CMS Myth presents nice strategy for training CMS users: drop-in labs. The idea is similar to a college professor's "office hours" where the professor schedules time in his office to field questions from students. In this case, it is a computer lab that an expert on the system staffs on a pre-set schedule. Like office hours, this is a complement, not a substitute, to traditional classroom training. A contributor attends a class, goes through classroom exercises there, and then comes back later to practice what he learns on his own work.
This seems like an effective strategy for large CMS rollouts where it is impractical to distribute expertly trained power users across the office. Small companies could benefit as well. I can see an advantage of allowing users to learn from each other as they passively listen to the instructor solving their co-workers problem as they do they their own work in the drop-in lab. As any CMS user knows, each piece of content has its own little nuances and there are so many different ways to use a CMS. Working with an expert nearby shortens period of learning the most effective strategies for achieving the desired result. For example, "should I associate this image directly with this asset or put the image in a central image library and then reference it?"
Back in my in-house I.T. days, we used to make a point of "walking the halls" answering questions for weeks after a big system rollout. Drop-in labs seem much more efficient but you don't get quite the same amount exercise.