Can you share what worked and what didn't when it comes to training people remotely?

Checklists are the big one. We've got a big spreadsheet of general areas that people should know, each with a lecture attached, but those are for self-study; I go over each one in detail with each new hire in a series of sessions typically lasting ~3 months, at 2-3 sessions per week.

Separately, I hold what amounts to office hours 3 times per week, where anyone who feels like it can show up to ask questions—but new hires are encouraged to do so until absolutely certain they don't need to, and also to keep track of questions between sessions.

There's more, but this is the part that's easy to explain.

What didn't work... crucially, waiting for newbies to ask questions doesn't work; they won't. You need to actively go looking, and also bring up areas they might not even know they ought to ask about.

Thanks for the answer. I see the theme is you have to be proactive instead of passively dump info hope for the best. It makes total sense.