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Let's start with what not to say. Here's the absolute worst choice:
That's right. Nothing is the worst possible thing to say when someone you know is hurting.
I have known that, intellectually, for at least three decades. That's when my own boss lost his job. (Well, he didn't actually lose his job, but another layer of administration was put between him and the president, which so completely transformed what he did that it was the emotional equivalent.) I didn't know what to say to Max, so I said nothing. I went about my work in a way that distanced me from him as much as possible, rationalizing that I was saving him the embarrassment of having to talk about the demotion. A month later, though, when he had found a new job and was moving on, I was in his office to talk about something else and he suddenly burst out.
"Do you know how many people have TALKED to me in the last month?" he asked me. "One. One person had the guts to come in here and say 'Are you going to make this work or are you going to tell them to shove it?' Every other person at this university has acted like nothing at all has happened."
To this day I regret that I was not that person who said something but I also vowed I never again would let let my own embarrassment keep me from saying something to a hurting person. I've not always kept that vow, but I've been ashamed of the times I've failed.
So today, here is a handy list of things you can say when you are tempted to say nothing.
1. I'm sorry.
2. I'm thinking of you.
3. You're on my prayer list.
4. I love you.
5. I'll miss seeing you in the bathroom.
6. Hang in there.
7. I'll miss you the next time I have an apostrophe question.
8. Thank you for all you've done.
9. Good luck.
10. This sucks, doesn't it?
11. Let's keep in touch.
12. You weren't very good at your job, but I know this hurts and I regret that.
Yes, even number 12 is better than saying nothing.
You don't have to use them all of these handy phrases--please don't, in fact, use number five unless...well, use your own judgment. You'll be able to read the room and know if the person you're talking to wants to change the subject, but the elephant in the room will have shrunk to a manageable size. And feel free to make up your own something-to-say.
Just please, please, don't say this: