The holidays have a funny way of bringing up feelings that have been simmering under the surface throughout the year. And one well-intentioned comment about money can turn a perfectly good dinner into an incendiary family debate.
The holidays are one of the rare times when aging parents, adult children, and extended family are all under the same roof. That makes them a natural moment to start conversations about money, planning, and shared goals. The big caveat is that these discussions need to be handled with a little care and tact. The goal isn’t to solve everything. It’s about starting to talk in a way that keeps everyone at the table.
Start With Stories, Not a Lecture
The easiest way to derail a financial conversation is to let it turn into a lecture. No one wants to be talked at, especially by a sibling or child who has suddenly appointed themselves the family CFO. A better approach is to invite stories rather than issue out instructions.
Ask about the hardest financial decision someone ever had to make. Ask a parent what they wish they had known earlier. Ask a cousin what they hope the family never has to deal with someday. Stories naturally open the door to shared understanding, and they allow people to participate without feeling defensive.
Stories slow the conversation down; they replace “you should” with “here’s what happened,” which makes it easier for everyone to listen. Once stories are flowing, the practical planning tends to follow naturally and with less resistance.
As a family financial planner, I’ve been the intermediary for many discussions like these. I’m obviously not enjoying ham and eggnog at my clients’ Christmas tables or kicking back a few latkes in the lounge during the holidays, which is why I’m sharing this advice here.
Timing Is Everything!
When and how you start the conversation matters just as much as what you say. These discussions shouldn’t happen before the meal, when people are hangry or distracted. Waiting until everyone has eaten, dessert plates are cleared, and the room has settled helps keep the tone calm. Food lowers defenses, so wait until after the peppermint stick ice cream has been served!
Before the Eggnog, Not After
There’s also a clear line to draw around alcohol. Serious financial conversations are best had before the eggnog starts flowing; this is not the moment to debate AI-driven car wash investments or the next “can’t-miss” crypto opportunity. Clear heads make for better decisions and fewer holiday regrets.
Family Financial Talks – Clarity Beats Avoidance, Everytime
At some point, families need to talk about the unglamorous but important details.
- Where are the documents?
- Who knows the passwords?
- Who understands how things are organized?
These conversations are about clarity. Putting them off year after year doesn’t make them easier; it just kicks the can down the road. Sorting through accounts and paperwork after a loss is something no family wants to do if it can be avoided; it’s terrible, and I’ve seen it happen to many families. Being ahead with legacy planning is a million times better for all than being behind with it.
One way to avoid tension is to make sure no single person dominates the discussion. Think of it less like a presentation and more like a roundtable. Everyone has a role. One person may focus on logistics, another on family values or history, another on next steps. When responsibility is shared, the conversation feels collaborative.
Family Financial Talks – Progress Over Perfection
A little financial etiquette goes a long way. No interrupting. No mocking. No surprise pitches. No “I told you so.” For every joke, there should be a serious recommendation underneath it. Most importantly, remember that you don’t need to solve everything in one holiday weekend. Starting the conversation thoughtfully and respectfully is often enough.
The real win isn’t walking away with all the answers. It’s knowing that when the time comes, no one will be left guessing, overwhelmed, or sorting through things alone.
If you and your family need assistance with legacy planning and succession planning, please reach out. Start the new year with some clarity and guidance.
