Nobody likes bad news, and delivering it is an uncomfortable job that comes with the very real possibility of ruining someone else's day. Unfortunately, it's often necessary. We have a tendency to be a little selfish and prolong the inevitable when offering up unfavourable tidings, but that's the wrong way to do it. Here's a better way.
Bearers of bad news have a bad reputation. Nobody likes to hear what they have to say, so it's unsurprising that the messenger approaches the situation with some level of anxiety. The phrase "don't shoot the messenger" dates back to 1598 in Shakespeare's Henry IV, Part II. Even earlier, "no one loves the messenger who brings bad news" was Antigone by Sophocles (written in or before 442 BC). We've been giving the messenger a hard time for many years, and that's probably led to consistent poor form when delivering bad news. It's time to forget all of that, drop the anxiety, and just get to the point when you have something difficult to say.
Get to the Point
Prefacing bad news with a lot of information is almost always a bad idea. While there may be a few exceptions here and there, providing all the facts before you get to the point creates an enormous amount of suspense and anxiety in the listener. If you relay the information chronologically, you may think you're explaining how your brother injured his foot. The person hearing this story, however, will be worried about where your story is going and imagine the worst. If you were writing fiction you'd be on the right track, but when you're sharing some bad news you need to get to the point as quickly as possible. Taking your time really only serves to make you feel better, not the listener.
Of course, what "the point" is can vary in levels of extremity. An injured foot is, of course, far less of a problem than death. Saying, "Hi Jill, Brian broke his foot and is in the hospital but he's fine now" works a lot better than "Hi Jill, Brian's dead." Sometimes the bad news you're bearing will require your delivery to be a tiny bit more gradual. You definitely do not want to waste time and beat around the bush, but in extreme cases you may want to start with something as simple as "I have some bad news". After that you can move right to the point.
The primary reason this is useful is because you sometimes need to indicate that you're serious. If you say "Hi Jill, I just saw your husband Fred kissing another woman in the supermarket," she might think you're joking. (On the other hand, in our examples Jill just lost her brother to a deadly foot accident so she may already be primed for bad news.)
It all comes down to this: Figure out the most important information, fit it into one sentence, and say exactly that without hesitation. When relevant, preface the news with a short statement such as "I have some bad news." It's that simple.
What You Said
I asked about this issue on Facebook, Twitter and Google Plus to find out how other people handle being the bearers of bad news. For the most part, you agree that it's best to be quick and to the point. Some of you also had a few helpful (and sometimes entertaining) suggestions.
Tami suggests offering some good — or at least helpful — news afterwards to lessen the blow, when possible:
Maybe there's a way to lessen the blow. [I]f you have to fire someone you like, let them know of other job openings you hear of and give a good reference, for example.
Cee Bee Cee reminds us not to start treating the bad-news recipient like a child:
Avoiding being patronising is a good way to go too. Treat them like a grown-up without being overly harsh about it.