There’s an old popular joke that is relevant to this lesson. To shorten it to its essence—removing most of the humor as well—would be something like this:
A teenager tells her parents, “I was expelled from school.” The parents were furious. She then adds, “And I’m on drugs” and the parents were furious. And then she adds, “And I’m pregnant” and the parents are furious, and so on and so forth—until she finally admits it was all a ruse. Why?
“Oh, I just got a bad grade on this one test.”
This is powerful because it’s true, putting bad news into perspective helps remind you what really is or isn’t important.
But there’s a more subtle message from the joke as well. The fury of the parents after the first 2 items on the list is so high that it doesn’t really change once you add items 3, 4, and 5 from that list as well. If your parents are so angry at you, they’re going to punish you in the most extreme ways they can. Then also telling them bad news X and Y doesn’t increase the punishment nor the anger anymore (since it’s already at the max.)
This is a key observation in sharing bad news. As long as your boss or client is going to be so angry with you, may as well get it all out there at once. Hey, you’re human and they’re human, and humans sometimes make mistakes. For some humans, too often!
Look at it this way. If you tell your client today, “I made tiny mistake X” and then tomorrow “I made tiny mistake Y” and the day after “I made tiny mistake Z” even if they’re all tiny, it gives him the impression you just make mistakes every day. But imagine you go 10 days and never mention a mistake, and then on day 11, you go to him and say, “I was reviewing my work for the last week and I found these 10 tiny mistakes I made” doesn’t that make you sound competent for doing that? The bug has become a feature!
But more interestingly, the converse is also true, and just as important. Imagine you have great news Q, R, S, and T to share with your client. You don’t speak for 8 days and then you tell him, “Great news: Q, R, S, and T!”. He’ll be excited. Then he won’t think about you for 8 more days until you talk again. But imagine, instead, every 2 days you ping him. On the first you say, “Great news: Q!”, and then 2 days later you tell him, “Great news: R!”, and then two days later, “Great news: S!” and so forth. Guess what? Every day he’ll be reminded of the great things you’re doing.
To any clients of mine reading this: yes, I’ve probably done this to you, and you should do this to your clients. Part of the beauty is that knowing explicitly this was a strategy does not in any way discount from its effectiveness.
