Request: A friend in need asks for a Trump-worthy loan.
What you should say: "I wish I could, but as a rule, I don't lend money to friends."
Why it works: It's clear that you are not singling out this person as untrustworthy.
Why you shouldn't feel guilty: Lending any amount of money can cause problems, says communications trainer Don Gabor. "It can change the nature of your relationship if the person doesn't pay you back."
How to avoid the situation in the future: Never lend money to friends and you won't get a reputation as a walking, breathing ATM.
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Request: A coworker wants you to chip in $25 for a gift for a colleague you wouldn't recognize at the watercooler.
What you should say: "Oh, I've never really had a conversation with Sam. I think I'll just wish him a happy birthday in person."
Why it works: Chances are, the person taking donations has no idea how close you are (or are not) with the intended recipient. By clarifying the nature of your relationship — and emphasizing your intention to get to know the person better — you come across as thoughtful rather than cheap.
Why you shouldn't feel guilty: "A gift isn't a gift if it's an obligation," say etiquette writers Kim Izzo and Ceri Marsh.
How to avoid the situation in the future: If workplace gift giving is getting out of hand, take the lead in restoring sanity by circulating a card before someone can break out the gift-donation plate. Make sure others know you don't expect anything on your birthday.
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Request: Your third cousin asks to bring her boyfriend-of-the-month to your $150-a-plate wedding reception.
What you should say: "We've already had to make so many tough decisions to get the guest list down to size. We really can't squeeze in/afford another guest. But I would love to have you two over for drinks sometime so I can meet him."
Why it works: If you illuminate some of your behind-the-scenes planning, your cousin may get a clue about the inappropriateness of the request.
Why you shouldn't feel guilty: It's your party and your pocketbook, says author Patti Breitman.
How to avoid the situation in the future: Make a few calls before you put together the guest list to see if there are new additions you should consider as you plan.
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