Hey Colin,
I'm going to echo what others said. We're getting ready to enter year four and our PD has changed significantly over the last several years. We had a staged rollout, where expectations were raised incrementally. We came from a wild west environment, where some were using Schoology on their own, there was some Edmodo, and lots of Google Classroom. So, we had to wrangle everyone into one place.
We have an online course that teachers can work through, also earning badges along the way. We start with creating Pages and Assignments and looking at how the Calendar pulls things together. Then, we layer in Modules, Quizzes, and Discussion as extensions of those early building blocks. I push advanced users into Outcomes and Rubrics so they know what their students know and can react more fluidly to needs.
For in-person work, what I've found best is to split those topics into "supported work sessions." I would do spurts of teaching, 20 minutes or so to show best practice and ways to do things. For the beginner group, I would walk through each item in the menus (Assignment groups, scoring and submission types, etc) and answer questions as they came up. I would also use old classes as a model for participants to see how I would set things up. After the teaching, they would have time to start building things. I rotated and moved around the room, giving feedback and answering questions as needed. The pace was great and everyone had plenty of time to actually use what they were learning in the session.
It's definitely a lot to tackle, so I would say multiple opportunities with clearly defined scopes are the most important things to remember.
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