There's no simple answer, really.
Where possible, cultivating relations helps. People tend to act in patterns when they're avoiding something so you can learn to pick up when you're treading towards something uncomfortable for them.
Offering opportunities to say things in a face-saving way is a serious skill. Learning how to phrase things in that way where possible can help, but becomes less helpful if it is allowed to become an excuse. Balancing act.
However, moments where you need to be insensitive may still happen. Like getting unpaid bills actually paid.
