Q: What's the most common mistake managers make when planning for training?
A: Not planning for contingencies. It never goes according to your project plan. You always need to have resources available for training changes, for communicating issues, and for changing plans mid-stream.
Q: When's the best time to start communicating a rollout?
A: It depends on the size of your organization and the culture of communication. I would say as soon as you are committed to the plan and understand the implications to work groups you need to start garnering good will and feedback. Starting with the leaders of an organization gets early buy in and gets everyone thinking about what they might need to address. The pilot is when you practice the communication plan - putting yourself in the user's shoes - and tell them what's going to happen to them.
Q: Can you over-communicate?
A: Well...in theory you can but I have never seen too much communication ruin a migration. So I'm going to say never. Ever.
Q: How do you get busy people to show up to training?
A: The same way you would come -- you have to compel people. When you really think about what is in it for them and listen to their concerns about time, etc. you can tailor a learning plan that is meaningful to them. Accept you just aren't going to get everyone to come (unless your leadership mandates it) but you can get everyone to learn what is essential to their survival. Provide one-on-one support only for the most business -critical operations for each person. Oh and one more thing - food and giveaways compel people to come to training. :-)
Q: What do you do about the person/people who just don't understand?
A: Bolster floor support. Heavy floor support can serve two purposes: they help people with their specific questions and, in the process, teach people how to do their specific activities.