At some point we all have to be the one to deliver bad news to another person. Whether it's breaking up with a significant other or firing an employee, we all have to do it. Quartz recently published a story by an oncologist who has to deliver bad news on a daily basis on what some of the best practices are for doing so.
While his advice is certainly a bit skewed toward telling someone they have cancer, it can come in handy in almost any situation where you need to pass along information another person might not want to hear.
The first step is making a plan. If you do in without a clear-cut idea of what you want to say, then you're likely to get tripped up and have a less-than-stellar delivery. Plan the conversation, and have any other conversations you might need to have related to the issue as well. For instance, if you're telling your roommate you need to move out, let them know that you've already spoken to the landlord and that he is fine with your roomie finding someone new and adding them to the lease. Do as much legwork as you can beforehand so there aren't a ton of lingering questions post-convo.
Get to the Point
There's no need to add a giant preamble to bad news. You're doing both yourself and the person you're talking to a disservice. Instead, get right to the point of the conversation. While you're delivering the news, don't be afraid to pause occasionally to allow the other person to ask questions or interject their own thoughts.
No one wants to be the bearer of bad news, but everyone has been told bad news at some point in their life. Think about how you would feel in the other person's position and try to empathise with them.
When you go at delivering bad news by considering the other person, you'll both likely have a much better conversation.