There is no option to force that dialog for a "update views" command since the software doesn't see that as a drawing change (we all know the drawing is changing but to the software, that is a model change). If you move a dimension or edit text, that is a drawing change and I assume you are getting the continue/check-out dialog box, correct?
In the past I used the workflow your users are using. I changed my workflow for several reasons. My current workflow is that before I work on a model or a drawing, I deliberately go and check out the models/drawings I am expecting to change. That puts me in control of what gets checked-out compared to letting the software tell me something is changing and asking me if I want to check out the model/drawings. If I get the pop-up dialog, that tells me that something is changing that I didn't expect to change and I need to research that to verify I am intending to modify that object.
It is my opinion that waiting for the software to tell me I am changing something is going to make the users complacent about the message and they will simply "check-out" everything when the dialog box comes up, which will in turn create "changes" to models that were not necessarily intended or desired.
