How to Say the Hard Things

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