First day, first time... the user didn't know to press F1 for help... I made sure it was ALWAYS on the screen after that (back in the days of MS-DOS). One time he asked "what happens if we disconnect right now?", the next week and forever after, it was immune to data loss if there was a disconnect.
The main thing I learned is that people are doing a job, your software is just a tool, and it should make it as easy as possible for them to keep doing it.
Oh... and never have them type data more than once.