Situation: There's a job opening at your company, and your friend asks you to recommend her for the position. You love her to death, but you wouldn't trust her with your favorite stick—let alone the sales department.

What to Say: Since she's a friend, there must be something you like about her. Lead with that:
  • "It seems to me that what you're good at is working with people and being creative, but this job requires strict organization. It may not be a great fit." — Douglas Stone, coauthor of Difficult Conversations
  • "Give me your résumé. I don't have a lot of say in these matters, but I'll bring it to the right people. I should tell you, though, that there are a lot of people applying for the job, so it may be a long shot." — Jeffrey Fox, author of How to Become a Great Boss

Situation: A friend wants to borrow your car—and you've seen how she drives.

What to Say: If you make a policy and stick to it, it'll be hard for her to argue with you.

  • "I know this sounds weird, but I just have a thing about this car. I get freaked out about anyone else using it." — Douglas Stone, coauthor of Difficult Conversations
  • "I'm sorry, my insurance policy says that I just can't have anybody else driving the car." — Jeffrey Fox, author of How to Become a Great Boss
  • Or opt for humor that gets the point across: "I'd like to, but if anything happened to it, I'd have to kill myself." — Holly Weeks, instructor at the Radcliffe Institute at Harvard University and author of the Harvard Business Review article "Taking the Stress out of Stressful Conversations"

Situation: An acquaintance is telling jokes you find racist, homophobic, sexist, or all three.

What to Say: Denouncing someone as a racist or homophobe is likely to start a big fight. How direct you want to be in your response depends on the situation—you may want to make less of a scene at a friend's dinner party than on the street—but you want to leave little doubt about your position.

  • In the workplace, such talk can be grounds for firing. Use that as a way to scare the joker off the subject. Just put your finger to your lips, lean in close, and whisper, "The walls have ears." — Jeffrey Fox, author of How to Become a Great Boss
     
  • Give the person a hard look and the straight truth. You want to make it very clear you don't agree with him: "This is not a conversation I would like to be a part of." — Judith Martin, a.k.a. Miss Manners
  • "When something is funny to you but not to me, I don't know what to say." — Holly Weeks, instructor at the Radcliffe Institute at Harvard University and author of the Harvard Business Review article "Taking the Stress out of Stressful Conversations"

Situation: You've got a monster for a boss: a yeller, an insulter, an all-around jerk. How do you handle this situation?

What to Say: First of all, you don't want to have the discussion mid-yell, when you're probably too flustered to make sense and the whole office may be watching. You need to find a way to postpone the conversation, something like:
  • "I'd really like to talk about this. Can I come to your office in a half hour to go over the problem?"

Then later, open the conversation with a line acknowledging the boss's situation, rather than putting him on the defensive.
  • "I know you're under a lot of pressure right now and that you really need to get results. I've got a suggestion that I think will help. But when I'm shouted at, my mind goes totally fuzzy. I clam up and I just don't do as good a job." — Barry Winbolt, psychotherapist and the author of Difficult People

Situation: People are making fun of or complaining about a friend of yours behind her back. What can you say to get them to stop?

What to Say:
  • "Well, she always speaks so highly of you." — Judith Martin, a.k.a. Miss Manners
  • "Really? I've had the opposite experience with her. You should give her another chance." — Jeffrey Fox, author of How to Become a Great Boss
  • "You know, she's actually a friend of mine, and I'm starting to feel a little disloyal here." — Joseph Grenny, coauthor of Crucial Conversations

Situation: Your best friend shows up with an unfortunate new haircut. She asks your opinion.

What to Say:
  • "Wow. That's really interesting. I've never seen anything quite like that." — Barbara Pachter, author of The Power of Positive Confrontation
  • "I'm the wrong person to ask, because I really liked you with longer hair. But it's good to see you so excited." — Douglas Stone, coauthor of Difficult Conversations
  • If you know she hates the cut herself, you might try a little humor: "Oh, my. Who else was hurt in the ceiling fan accident?" — Carol Leifer, writer, actress, comedienne, and producer

With fashion purchases, which are more easily changed, you can afford to be more blunt:
  • "I love you in anything. I love you in rags. I don't like you in that dress. Take it off and take it back." — Betty Halbreich, head of the personal shopping department at Bergdorf Goodman

Situation: You value your friend's opinions, but not necessarily every minute of the day. How can you tell her to back off?

What to Say: As always, accusations—i.e., "You're nosier than Ray Romano" —are likely to put the person on the defensive and lead to an argument. Start with acknowledging her good intentions:
  • "I know you're trying to be helpful, and I like to know what you think. At the same time, I feel I need to make my own mistakes." — Douglas Stone, coauthor of Difficult Conversations
  • "You can fall back on an old Chinese saying: 'Please don't trouble yourself with my concerns.'" — Holly Weeks, instructor at the Radcliffe Institute at Harvard University and author of the Harvard Business Review article "Taking the Stress out of Stressful Conversations"

Situation: Your job description says "manager," but you're sorting paper clips. How do you ask for more responsibility?

What to Say: "This is what I want to do, and this is how much money or time it will save or make for the company." (Nothing gets a boss's attention like the sound of cold, hard cash.) — Jeffrey Fox author of How to Become a Great Boss

Situation: You're working 60-hour weeks and the boss keeps piling more and more on your desk. How can you make it stop?

What to Say: "Thanks for trusting me with all this work, but I'm starting to worry that I won't be able to do all of it well. Can you tell me what the most important parts are, so I can concentrate on those?" — Barry Winbolt, psychotherapist and the author of Difficult People

Situation: You've endured a friend's daughter's first piano recital. The girl is not the next Horowitz. Now your friend wants to know what you thought.

What to Say: Our experts unanimously agree that this is one situation that does not require saying the hard thing. "What possible use would it serve?" asks Judith Martin, a.k.a. Miss Manners. So if you don't want to outright lie, find something to praise besides the child's tunefulness.
  • "She really seems to know what she's doing!" — Barbara Pachter, author of The Power of Positive Confrontation
  • "Gosh. She was really composed out there." — Barry Winbolt, psychotherapist and the author of Difficult People

Situation: An acquaintance is in town and wants to meet. You'd rather gnaw off your left arm than devote any time to her right now, but don't want to end the relationship. How do you beg off?

What to Say: Don't lie. The moment you do and say you'll be at x, y, or z, you know you'll run into the person at q. Offer a blanket response rather than a specific scheduling conflict.
  • "This is a terribly busy time for me. I'm saying no to everything right now. Why don't I give you a call when I'm more free?" — Judith Martin, a.k.a. Miss Manners
  • "I'm so wiped out that I know I would just be a drag on you." — Barry Winbolt, psychotherapist and the author of Difficult People

Situation: Someone you never want to see again keeps asking to meet up. What can you say, as kindly as possible, to ensure that you will never hear from him or her again?

What to Say: Here you want to be very clear; a little discomfort now will spare you both the pain of more calls later.
  • "I've enjoyed our friendship, but I just can't make it a priority going forward." — Joseph Grenny, coauthor of Crucial Conversations
  • "You and I have really different expectations for this friendship." — Douglas Stone, coauthor of Difficult Conversations

You'll probably need to back up each of these statements with specific reasons, such as "You always want to talk about your problems, but you never ask about mine" or "We don't really have anything in common anymore" or simply, "We should save each other the disappointment."

Situation: The dishes are piling up in the sink; the sales report is overdue; nobody has taken out the recycling in weeks; or you're working overtime to make up for other slackers. How can you get a housemate or coworker to start pulling his weight?

What to Say: The first thing to do is some research: Identify exactly what the person was supposed to do and what he has actually done. Then present your findings in terms of a busted contract.
  • "Look, when we started, we agreed that you would do x, y, and z. It seems to me that x isn't getting done. What's happened?" — Joseph Grenny, coauthor of Crucial Conversations

Issue a reminder emphasizing that you're on his side: "Is there anything you need to get the job done?" — Barry Winbolt, psychotherapist and the author of Difficult People
  • If the lazy person's work winds up falling to you and all else fails, issue a simple, firm refusal: "You've left me with a task to do and, I'm sorry, I just can't do it. If that's a problem, you're going to have to take it up with the boss." — Judith Martin, a.k.a. Miss Manners

Situation: How do you deliver bad news—death, firing, breakup, arrest—as painlessly as possible?

What to Say: Here's the thing: Everybody wishes there were some magic words that would make bad news somehow less bad. There aren't. Our experts say the best you can do is be honest, to the point, and sympathetic. One line of warning helps; try saying "There's something upsetting that I need to tell you." — Douglas Stone, coauthor of Difficult Conversations

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