A useful technique which I never see anyone use is to add a tooltip for a disabled UI control explaining why the control is disabled. So if there's a listbox which is disabled and it's not clear why it is disabled, I want to hover over it and it tells me why it's disabled. I want to see something like "It's disabled because two textboxes on the screen were left blank or because I didn't enter enough characters in some field or because I didn't make a certain action.".
I get into sooooo many such situations and it's frustrating. Sometimes I end up posting in the software's forum asking why a control is greyed out when a tooltip could have helped me in a second! Most of these software have help files which are useless in these kinds of scenarios.
Try to pretend you know nothing about your software and try using it. However this is not practical because you already have a certain mind set towards the app. So watch fellow developers or friends use the app and look out for the pain points and ask for feedback.
