How to have the right kind of money conversation on Thanksgiving weekend

Family gatherings can trigger uncomfortable conversations, and Thanksgiving is no exception. But with the right approach, tackling financial issues head-on instead of tiptoeing around them could become the most rewarding part of the holidays.
The key to transforming family friction into financial harmony lies in broaching tricky topics with empathy, advisors say.
To avoid situations in which family members feel ambushed, Janine Guenther recommends scheduling a discussion beforehand. It also helps manage expectations.
“You could say something like, ‘We want to talk to you and your sisters about our retirement plans during Thanksgiving break, and we’d like to do that on Saturday afternoon,’” says Ms. Guenther, a portfolio manager and senior family wealth advisor at Bellwether Investment Management in Vancouver.
“If [the topic is] particularly sensitive, you might want to plan to talk [about it] when you don’t need to make eye contact – maybe plan a pickleball game or discuss while you’re all raking leaves.”
Wendy Brookhouse, a money coach and founder of Black Star Wealth in Halifax, recommends a practical approach to discussing financial matters.
“A great way to introduce the conversation may be to reference work you’re doing with your advisor, lawyer, or accountant, and how it made you think about what plans everyone else has,” she says.
Bringing in a neutral reference can make these discussions feel less personal and accusatory. Another effective method is to use articles or videos that cover important topics – such as the need for a will, says Ms. Brookhouse. Online tools such as executor checklists or videos on benefits planning can make these discussions easier to digest.
“You might casually mention an article you read about what happens if someone dies without a will and use that as a stepping stone to discuss estate planning,” she says. “By using external resources, you create a buffer that makes it easier for everyone to engage in the conversation without feeling defensive.”
Kelly Ho, a certified financial planner and partner at DLD Financial Group in Vancouver, offers another effective tactic: “Ask how family friends are doing and use it as an opportunity to bring up issues that have yet to be discussed, such as health wishes, long-term care, and the type of lifestyle they’d like to maintain.”
Thanksgiving gatherings are ultimately about connection, so conversations about friends or acquaintances can be a natural segue into financial topics. To avoid making anyone feel uncomfortable, keep it general, Ms. Ho advises.
“Always come from a place of care as these topics are extremely sensitive and, for some families, taboo,” she says. “Maintaining a light, curious approach rather than an interrogative tone can make all the difference. Instead of cornering a family member with pointed questions, consider sharing a story and then let the conversation evolve naturally.”
Whether it’s a personal discovery or a friend’s experience, this helps create a relatable entry point for proactive discussions on both sides.
Sara La Gamba, a senior financial advisor at SPM Financial and King Financial and Benefits Inc. in London, Ont., cautions that not everyone may be ready to have these discussions – and that’s okay.
“Planting the seed for a future conversation may be the most reasonable step,” she says, adding that creating a non-judgmental space is the most essential factor in helping family members feel comfortable to open up on their timeline.
Thanksgiving is also a good opportunity to check in on how new university students are managing their finances.
“It’s important to tell them it’s perfectly normal to be unsure when you’re first on your own,” Ms. Guenther says.
When held in a supportive environment, these conversations can help build both financial literacy and confidence.
Tami Romanchuk, a financial advisor based on Vancouver Island, points out that Thanksgiving is also a moment to express gratitude.
“It’s a good time to remind loved ones how grateful we are that they’ve put their plans in place,” she says.
Acknowledging the work that’s already been done can make the conversation more positive rather than just focusing on what’s missing. If some important plans still need to be made, it’s an opportunity to encourage family members gently, she says.
“Some of these conversations take courage as planning for the unexpected can be very difficult for some people. I’ve watched clients become visibly uncomfortable in their seats when discussing items surrounding the death or serious illness of a loved one,” Ms. Romanchuk says.
Currently recovering from a craniotomy after being diagnosed with a brain tumour when her daughter was only a year old, Ms. Romanchuk is acquainted first-hand with the necessity of these conversations.
“While they weren’t able to remove the full tumour, I continue to realize how precious each day is,” she says. “My future goal is to talk to as many people about the importance of living benefits as possible.”
Editor’s note: Tami Romanchuk, a financial advisor based on Vancouver Island, is no longer with Shoreline Financial and Insurance Services, as a previous version of this article stated.