We all make mistakes! Below are my tips to get you more easily out of the hot seat.
1) Choose the right moment.
Wait for when the person is happy and relaxed, or even feeling a bit guilty for something they've done to you recently. The worst time to break bad news is when the person is preoccupied with something else, such as running late, getting home from a long day at work, exhausted from exercise or yard work, or already dealing with bad news from a sibling or coworker.
2) Avoid Mondays and Fridays.
For people with a Monday to Friday schedule, Mondays are a tough day because the fun and relaxation of the weekend is over. Similarly, Fridays are a day most people are excited for because the hell of the week is almost over. Breaking news on a Monday or Friday is likely to make the person angrier than normal because you're either making a shitty day worse than it already is or ruining what should have been the best day of the work week.
3) Get opinions from others who know the person.
If you have a mutual friend, or a family member who you trust, confide in this person first and see if they can offer any insight into the best way to break the news to the person in question. If the topic is too confidential for others' knowledge, you could also confide first in an anonymous way to someone online.
4) Describe the problem as if it happened to someone else.
Doing so allows the person time to process the situation objectively without the emotional reaction of it actually having happened to you. Then, once you've spilled the beans, you can gently let them know that the deed was actually done by you.
5) Take responsibility for the problem.
In many cases, the reason the bad news is so difficult to break is because you screwed up. Accepting your mistake and providing concrete examples of what you will do to prevent the problem from happening again will assuage any anger or disappointment and give the person a sense of reassurance.
6) Bury the bad news in lots of good news.
A good rule of thumb is to counter bad news with four pieces of good news. The gravity of the bad news will be overshadowed by the good news, so the person's reaction is likely to be less severe.
7) Use a movie or book that the person knows to introduce the subject.
This won't be possible for the delivery of all bad news, but if you start off the subject by saying something like the following, it will remind the person that you are not the first person who has done this:
"Hey, so you remember how in [movie the person knows], the guy was a decent guy, but he got pressured into [news you are trying to break], and then the girl freaked out even though it clearly wasn't all his fault? So, I went through that, and I am that guy."
8) Cite actual statistics and facts about the problem.
Doing so will put the problem into perspective for the person because it won't just be your opinion anymore. Check statistics for how common the problem is and cite available resources and possible solutions. This shows that you are responsible and determined to make things right.
9) Write a handwritten letter.
It can be hard in the heat of the moment to express ourselves how we planned to due to 'going blank' or being interrupted by questions and accusations before you've had a chance to finish. Writing a letter first will make sure the story is straight for you, and in turn, for the person. It will also be a good reference for when the person does, inevitably, contact you afterwards (unless you are literally planning to disappear).
10) Allow the person to fully react to the news.
Try your best not to interrupt the person once you have spilled the beans. Don't raise your voice. Don't make witty or sarcastic remarks. Don't roll your eyes or use profanity. Stay calm and let the person finish. This demonstrates maturity, restraint and respect. When they finish, politely ask if you may have a turn to speak so that you both can reach an agreement.
How have you broken bad news in the past?
Please share any tips you have for everyone's benefit!