If you know that you have a problem being inconsiderate of other people's feelings, as i have been told i have, then you may want to try to figure out how to say something without stomping all over the other person. Instead of being "brutally honest", you might propose it as, how do WE solve this issue? People in your past might not have been open to such a discussion, but that would be transference making you assume that your t would take it badly also.

Eta - hope i didnt give away any trade secrets there!