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.
My main issue is that decisions about features software should have shouldn’t be delegated to a specific role. That’s absurd. I’ve never seen a situation where this works. Because a product owner can be misaligned with executive level and their specifications for new requirements are always lacking.
But because of the way the industry works I could probably see myself taking on such a role someday as it seems to be one of the paths away from being a direct IC programmer into something more.