“I don’t want to date anymore.”
“We’ve decided not to hire you.”
“I’ve decided not to buy your product.”
“I don’t want to hang out with you any more.”
“I want a divorce.”
“You didn’t win the contract.”
“You didn’t get the grant.”

Of course, every rejection is different. Declaring that you want a divorce is not the same as sending rejection form letters to hundreds of candidates not hired. Still, there’s a general art to saying clean compassionate “no thank you’s” that runs through all rejection communications. It’s an art, not a science, since there’s no perfect formula for ending things. Here are nine tips for how to think about that art:

1. Concentrate on honoring them, not you: We often feel guilty about having to say no, and end up rationalizing to comfort ourselves, not the rejected person. Don’t. Keep your rationalizations to yourself. Own your decision. Don’t add insult to injury by saying “I’ve decided not to engage with you any more. Now indulge me while I monologue to comfort myself.” That’s tacky.
2. In relationship we share; out of relationship we don’t: In a relationship, there’s an “us” to manage by giving and taking feedback. Out of a relationship, we’re just two separate people and “live and let live” is the cleaner approach. Rejection is the transition from “us” and separate individuals and there’s a tendency to carry forward the assumption that we owe each other feedback. Keep in mind that your rejection communications are part of that transition. Signal the transition cleanly by not pretending you’re still working things out together through feedback give and take.
3. Don’t patronize by explaining how the world works: Here’s something common but unnecessarily cold: You submit a proposal and it’s rejected with a letter that explains that, “we receive lots of proposals and can’t support them all.” Well, yes, you knew that. In more intimate rejections we find something similar, for example being told by a partner who is dumping you how love works and that it’s always a gamble. As if you didn’t know that. These patronizing explanations are probably what the rejecter needs to hear, not the person being rejected. They imply something like, “I’ve decided we don’t belong together and furthermore I’m more worldly than you.” It’s bad boilerplate. Remove it.
4. Don’t make stuff up: You probably don’t know all the reasons why you decided to say no, but you may be tempted to claim you do or to make up simple reasons that let you off the hook and humor the rejected. Remember how closely people are listening when you’re saying no to them. What you say can have a huge influence, so be careful. Don’t send them on a wild goose chase trying to solve a problem you made up on the fly to justify your “no.”
5. Acknowledge subjectivity: To feel final about a decision to reject, you may be tempted to reject with high certainty that it’s the right decision. It may well be the right bet, but it’s not a certainty, it’s a subjective guess your making about whether you belong together. Acknowledge the subjectivity. Don’t say “There isn’t a good fit,” but something more like, “I’m committing to a bet that there isn’t a good fit.”
6. If possible offer, but don’t volunteer honest feedback: Since they’re listening attentively to your rejection, it’s an opportunity for them to learn from your final feedback, not to learn what’s objectively true but to learn one rejecter’s subjective impressions. They don’t owe you a listen, but they may want to hear what you have to say anyway. Consider saying something like, “I have guesses why I’ve made this choice, and if you want to hear them I can share them but only if you want them and I’ll share them only on condition that you don’t try to override them. I’m not reentering negotiation.”
7. End it efficiently: No one likes being rejected and some will try to delay it as long as possible or indefinitely by keeping the conversation going.  Combine that with the sugar coating “we can still be friends” with which we often paint the bitter pill of rejection, and a rejection can turn into an open-ended discussion or debate. That’s not good for either of you. Though it may seem cold to just end it, in the long run it’s the kindest thing to do.
8. Don’t let it go to your head: Some people end up doing a lot of rejecting, for example HR professionals, foundation directors, and attractive, successful people. It’s hard not to let it go to one’s head as though you’re the supreme objective judge, a god deciding what’s good and bad. That makes for uncompassionate rejections but also a distorted worldview. If you end up doing a lot of rejecting, offset the tendency to end up swell-headed by remembering times when you have been rejected and when you will be again. No one gets to always reject. For example, we are all rejected at death, the ultimate rejection.
9. Strive for kindness even if they don’t think you’ve achieved it: We often hear that there’s always a way to be kind. It’s not true. Because kindness is gauged subjectively, you may think you’re rejecting kindly, but on the receiving end it may well hurt and therefore feel unkind. The rejected may well want to scold you for your lack of kindness. Maybe they’re right; maybe they’re wrong. Do your best to be kind when delivering rejections but don’t assume that your best can ever be perfect. Rejections hurt no matter how compassionately they’re delivered.

[Jeremy Sherman]