Well, you have probably received more feedback than you can handle, but here is how we have handled things at the University of Bridgeport.
After switching from Blackboard to Canvas some 3 years ago, some admins and faculty went through 3 2-hour sessions with Canvas. That helped with the transition, though most if not all of the things we learned this way are available in the Canvas guides.
To train our faculty, I have developed a Certificate Course in Online teaching with Canvas. This took lots of time and work, but it was well worth it. It consists of Modules containing needed info / instructions on performing every possible task, starting with setting up one's profile, etc. In addition to the purely "how to do it in Canvas" instructions, I have added a number of sections on why do it this way rather than that way, what choices mean, and even basic explanations on the nature of online learning (interactivity of online discussions - if done right; how to successfully use online quizzes, etc.). This way, we could both show our existing online faculty how to transition to Canvas and help new faculty understand the concept of online teaching. The certificate (received by dozens of faculty) is an additional incentive to some, while other don't care.
Once our university created a new division called Global Learning Initiatives (GLI) where subject Matter Expert work with Instructional Designers to create high quality courses that can then be taught with minimal changes by any instructor, we created a new certificate where instructors merely learned what was needed for successful course delivery, rather than creating a course by themselves. Finally, once classroom instructors started using Canvas more and more, turning classroom courses into hybrid courses, we created a third certificate course to help campus instructors supplement their classroom instruction with Canvas.
Obviously, there is quite a bit of overlap between these 3 certificate courses, but also many differences, hence it took a significant additional amount of work. But again, it was worth it. Now that we have it, we only need to update it whenever needed - and of course, I need to evaluate new instructors' performance, give feedback, etc. what this takes is a full-time position and someone who know how to do this.
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