How to Take Control of Awkward Money Conversations

“People get weird around money,” says Bobby Soler, a financial advisor with the firm Strategies for Wealth in New York City. “It can be really awkward with family members.”

He knows from firsthand experience. When it came to caring for his grandmother, his family avoided planning discussions, which led to stressful disagreements between siblings. He wants people to prevent that kind of situation by talking about money — even difficult topics like end-of-life planning — well in advance.

Opening up the conversation by using a recent news article can be an easy way to start, says Dan Casey, founder of the financial firm Bridgeriver Advisors in Bloomfield Hills, Michigan. You could mention that you read an article about the value of using a retirement calculator, for example, or how many people are concerned with having enough money.

That way, he says, “you’re just passing on knowledge,” and can avoid unintentionally seeming like you’re trying to find out what inheritance you might one day receive.

Try questions that evoke hopes and dreams, says Erika Wasserman, CEO of Your Financial Therapist based in the Miami, Florida area.

One question you can pose is, “Mom and Dad, what is retirement going to look like for you?” Then, you could follow up by asking about where they want to live or whether they plan to move.

“When you give people a chance to explain their vision, it gives you a different perspective and allows them to open up,” she says.

“Focus on the fact that you really care about them,” says Annie Cole, a Vancouver, Washington-based money coach and author of the book “101 Ways to Earn More, Build Wealth, and Live Rich in Your 30s.”

She recently asked her dad if he had a will.

“We called out the elephant in the room and just said, ‘This might feel a little awkward,’” she says. That comment broke the ice and made everyone laugh, and then they had a productive conversation about his retirement plans.

Try giving siblings and other involved family members a heads up before broaching a heavy topic together, says Elaine Swann, a San Diego, California-based etiquette expert and author of the etiquette guide “Let Crazy Be Crazy.”

She warns against springing a conversation about estate planning on siblings or family members.

“If you have a group family text, bring up the fact that you want to have a conversation,” she says, then pick a mutually-convenient time. That way, they can be physically and mentally prepared.

Have a conversation about vacation cost-sharing during the planning process of the trip, Casey says. If you are offering to host and pay for one element but not another, spell that out, he adds. And if you know a financially-strained family member can contribute in another way, such as cooking, discuss those contributions in advance, too.

Similarly, at a group dinner, it’s helpful to talk about splitting the bill before placing orders, Swann says.

“There’s nothing wrong with saying, ‘Hey, how would you like to split the bill?’ Have the conversation beforehand so it’s less awkward and you can sit back and enjoy the meal,” she says.

“It’s OK to put a boundary in place,” says Wasserman. “You can say, ‘Right now I’m working through financial issues and I have the support I need, but I appreciate your love and support.'”

Family members often want to make sure you’re OK or at least have a plan in place. “They want to see you are handling it. That is just reassuring to people who love you.”

If you don’t want to talk about your situation, Swann suggests being blunt.

“That’s not something I want to talk about. So anyway, how was your vacation this year?” is a script that helps you firmly pivot to another topic. “Be prepared to shift the conversation,” she says.

If you agree to loan family members money, it should always be in writing, Casey says, including any agreement around when it will be repaid.

If you don’t want to loan family members money, then Cole suggests offering to help in non-financial ways, such as by preparing meals or caring for any pets. You can also be honest about why you’re declining to provide financial assistance.

“We say, ‘We don’t mix family and money in that way,’” Cole says. “That’s our saying, and people understand.”