Your best friend wants you to help her land a job she'd be lousy at. Your boss shrieks at you. Your sister's new hairstyle looks like an old pie. What do you say to these dear folks? We'll put the words in your mouth.
Difficult conversations come in all varieties: problems that need addressing at work, confrontations with friends, disagreements with family members you don't want to hurt. Most of us will do nearly anything to avoid these little talks. Sooner or later, though, work will become unbearable, friends will wonder what's going on with you, family will bring the problem back to you—in short, the unsayable will have to be said.

We asked a panel of communication experts for their recommendations on how to say the hardest things. Some of these scripts you'll be able to use verbatim; others you'll have to tailor to your specific situation. Still others are good to keep in your back pocket, ready to be used when tough encounters make a surprise appearance. We hope they will ease your way over the rockiest conversations.

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

Next: What to say to the Borrower, the Sexist and the Boss
From the March 2003 issue of O, The Oprah Magazine

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