At my current job and in past jobs, the best method for letting people know what is possible is to venture out of the IT area into the users' work spaces.
This included doing the jobs they do with the technology we created. I learned quickly on how inefficient my interface was when standing on a ladder seven steps up with the handheld computer in one hand and a box in the other. By working at their jobs we get to see the myriad steps and methods the users sometimes use to get around the program's shortcomings.
We also regularly do a walk-around to see how things are going and to say Hi. A lot of the time, the best time saving suggestions were from users, who when just chatting, mention how cumbersome certain features were. Often the fix was quite easy and saved a ton of their time.
I agree with other posts. Users seem to be afraid to ask for changes or are uncertain how we will react when asked. A constant reminder is still needed to get them to ask for changes and even more importantly, let us know when there is an error.