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

Next: The best way to handle bad news


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