1. First, Tread Carefully
Solomon recommends prefacing any conversation with honesty: Start by saying, “This is really awkward and difficult for me to talk about,” she says. Let them know that this is a tough subject for both of you, and your friend won’t feel put on the spot.
It’s also important to give your friend permission to stop the conversation at any time. Though it depends on the person, there might be some areas where you simply decide not to go there. Discussing a friend’s salary, for example, or a case where a friend loses a job and clearly knows money is tight, might be times to hold back.
Ask yourself if you are even capable of bringing up money without sounding judgmental. “Some people just have the right body language and tone of voice. They can say things and it sounds helpful,” says Solomon. “Other people can say the exact same thing and it comes off as scolding and acting like a disappointed parent.” If you’re in the latter group, accept that perhaps you’re not the one to intervene.
2. Choose Your Moment
Often, money can come up organically in a conversation. A friend might mention he’s splurged on another new gadget he didn’t have the funds for, or joke about the single digits in her savings account. Decide if this is the right time to jump in, Levine says. A lighthearted comment could be a good segue to a more serious discussion … then again, a lecture out of nowhere could be a perfect recipe for ruining brunch.
In terms of when not to speak up, here’s a good rule of thumb: Solomon advises using the acronym “HALT” to evaluate whether the setting’s right for such a touchy topic: “Never try to have a conversation when someone is Hungry, Angry, Lonely or Tired,” she says. Instead, she advises, pick a time when you’re both relaxed.
3. Frame the Conversation Positively
Sindy Martin, a business etiquette consultant, had a close friend with a bad habit of borrowing from family and friends—and never repaying her debts. At lunch one day, Martin says she used the classic “sandwich approach” to address the situation: First she chose a positive, like her friend’s career success, then she addressed her concern (not paying back money borrowed), bookended with another positive—her friend’s great reputation in the community. “I never used the word ‘you,’ ” she said. “I approached everything from the ‘I feel’ perspective.”
You might also start by sharing a story of how you yourself solved a money issue in the past. It’s easy to get preachy, but if you first recognize that no one is perfect with money, you can make the topic more of a mutual discussion than a nagging lecture, says Solomon.