Show up in person.
Tempting as it may be to e-mail or have a one-way conversation with an answering machine, talking face-to-face shows respect, especially if you're discussing the loss of a job or relationship. Also, an e-mail or voice message is easy to misinterpret, whereas when you're physically with someone, you can explain or clarify immediately so there's less room for misunderstanding, according to Judith Bram Murphy, PhD, a Manhattan clinical psychologist who also does executive coaching.
There's never a great moment to have a tough talk, but you can avoid undue hurt by finding the least terrible time (New Year's Eve is not the night to ask for a divorce), says Linda Sapadin, PhD, author of Now I Get It! Totally Sensational Advice for Living and Loving. The place, too, can make a difference: It should offer relative privacy, the option for a quick exit, and an atmosphere that will allow the other person to feel comfortable and react safely. (Sitting in a well-chosen restaurant can be more conducive to a sensitive conversation than driving in a car, where both of you are stuck after you drop the bomb.)
The impulse to memorize exactly what you're going to say is understandable (all the easier to just spit it out and make a beeline for the door). But scripting the entire speech as if it's a state of the union address will make you seem insincere, Sapadin says. Also a brusque, agitated delivery can cause both of you to feel worse, says Dana Bristol-Smith, president of Speak for Success, a business communications firm in San Diego. It's not a bad idea to practice the first few sentences to help you through the initial awkward moments, but after that, try letting the words come naturally.
The truth is, you don't want to hurt anyone. Nor did you likely cause the situation—you may be keeping it from becoming worse. Continuing to lead someone on, for example, will only create more heartbreak in the long run. If you have to fire an employee, it's probably because she's not performing up to snuff or the budget was cut and she's the least useful to the company. If the other person will be disappointed by what you have to say, perhaps it's because of her own expectations—ones that you don't share.
If you're stumbling over how to start, Sapadin suggests an opener like "I don't know how to say this, but I must tell you something" or "I don't want to scare you, but there's something you need to know."
You can soften the blow by paying tribute to the other person's strengths. In the case of breaking up, says Bram Murphy, you might sandwich the negative between positive statements, as in: "You are terrific—generous, kind, and funny. I've enjoyed our time together, and I've really grown as a person. But I just don't see us going forward together, and you deserve to be in a wonderful relationship."
Uncomfortable as this can be, keep in mind that most people wind down after an initial outburst. Remaining conscious of your breathing, keep it slow and steady—that will go a long way in helping you stay calm. (When you're nervous, you tend to breathe very rapidly or hold your breath.) Try not to interrupt or respond emotionally to the other person's upset. If their anger escalates and feels unsafe, announce that you are providing some time to cool down, and leave the room.
For someone who is visibly crushed or sobbing hysterically, acknowledging your role in her distress ("I'm really sorry this is making you so upset") lets her know you care despite the circumstances. If there are tears, offer Kleenex or a glass of water, and ask if she would like a few minutes of privacy, Bristol-Smith suggests. If she's angry, something like "I hear you" at least offers some validation of how she's feeling. Just make sure your empathy is rooted in reality, Sapadin cautions. "Saying, 'I can understand that you're angry with me because I disappointed you, and that was not the way I wanted it to work out, either,' shows concern without giving false hope."