I have been assigned a project where I need to start doing Salesforce usability testing with a customer service department. My issue is that I've never tested an application that will require user training. I generally have an application where the user won't get training, so I give them a task and tell them to show me what they would do. Pretty easy.
So I've been looking for guidelines on how to accomplish testing with an application that will require user training but haven't had much luck. My thought process is divided between these three approaches:
I could give them a task without any training and see where they go, just to see what they do. But my concern is that Salesforce is so large I'm not sure my findings would actually be helpful.
I could require a quick overview a week (not sure on the best time here) before the testing and then pull them in to see how they do. But how much training is too much training?
I could run a test or two and just have them run wild, then test with trained users, then switch back to new users, and so on.
I'll be testing once a week for the next three months so I don't have a ton of time before this project launches, but I do have a bit of wiggle room.
Does the UX Stack Exchange community have any advice on this or any documentation/guides/articles/books that might be able to help me plan my attack?