start from the beginning
If they are brand new to shooting...I would start them off on composition. Steady, well composed shots. Once they get that right, have them learn sequencing. Wide, medium, tight, super tight. 3 shot, 5 shot, 10 shot, 20 shot sequences. Once they learn sequencing, it's good to get them thinking efficiently so they don't burn through tape and waste time in the edit bay. 4 to 1's like they do at the NPPA news video workshop are great drills. Shoot no more than 4 minutes of raw, and edit it down to a one minute story. This should be video only, with no audio. And the video should tell a story. I can go into more detail on those if you're not sure how they work, but i'll stop there for now.
Once they've got composition, sequencing and 4 to 1's down...they're ready for VO shooting. Show them how the lav works and how to compose and interview, and they're ready for VOSOTS. Before they shoot a package with a reporter or anything, I'd have them try a couple natpacks by themselves (not for air, unless they rock). This will teach them a lot about shooting a package. Mainly telling a good story, but also about working the mic, picking up nats, editing a package, etc. Then hopefully, they're ready and will learn the rest as they go.
That process should take a week to two weeks hopefully. But it's different for everybody, just depends on how quick they learn.