How to Say the Hard Things

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

Next: How to handle strong opinions