As a trainer for new into digital techs - It can be very difficult. I've had techs and Dr.'s walk in and say to "just show me how to design an arch" which just boggles the mind, then theirs even when I go step by step.
My training regime to help people.
1) DB - what to enter, and when, shortcut keys to make it faster
2) Scanning in ColLab. What options, what to scan when, how to scan, tips for getting harder areas.
3) SINGLE UNIT. Learn how to place that tooth, get used to the movement in a digital space, learn the tools, tell them to get a feel for it.
4) 3 Unit bridge - learn the placement with extra teeth, if they seem to learn it quickly, you get to see the chain mode tool as well (otherwise it's info overload)
DAY 2 (yeah - you can't learn digital or a new software in 1 day)
1) pop quiz - enter in a single unit case, scan, and design on your own
2) learn the cutbacks
3) design a bridge again (chain mode this time if not 1st),show all the hotkeys again for designing (freeforming hot keys, placement hotkeys, etc)
4) Stress that they cannot immediately do this perfectly, they will get it though
5) show them every step and explain it like analog and how it correlates. This is just like waxing, you're just looking at a screen the whole time, and you don't have to build up the wax for a crown.
If they want "expert" training for expert mode, quick pathways, implants, etc. If they don't pick it up quickly, they have to come back. Learning this stuff isn't easy, but if your trainer equates it to your analog style, then it becomes a lot easier in my mind.
I've had someone tell me they let the software place the tooth in 3Shape hit the "adapt" buttons for everything, then send it on for milling. sure it works, ugliest work imaginable though. Designing with a little effort in 3Shape though can still be good. Same can be true to Exocad. You can "follow the yellow brick road" (wizard) as I call it, keep hitting next, then smash those adapt keys (with pull to contacts set first) - and you're "golden".
That is NOT what Exocad is for though.