Family money conversations start at the holiday table, advisors say

As families prepare to gather for Thanksgiving and the December holidays that follow, financial advisors say the shared table offers a rare opening for family money conversations that many households have put off for years. The goal, they stress, is not to settle the estate plan over dessert. It is to start a dialogue that advisors can turn into structured planning once the season ends.

The need is real. Fidelity Investments’ 2025 Family & Finance Study surveyed parents age 55 and older with at least $500,000 in investable assets, along with their adult children. It found that 68% of parents had not told their children what they would inherit, and 52% had not discussed their net worth with them. The stakes keep rising: Cerulli Associates projects $124 trillion will transfer through 2048, with about $105 trillion expected to flow to heirs.

For advisors, those figures point to both a service gap and a business risk. Practices that never meet a client’s children can lose those assets when they change hands. That challenge has pushed many firms to rethink how they retain clients’ heirs in the great wealth transfer.

Why the holidays suit family money conversations

Kent Waugh is a Retirement Income Certified Professional and wealth planner with Accenden Wealth, Parkland Securities LLC and Sigma Planning Corp. in Colorado Springs, Colorado. He said the holidays are often one of the only times several generations share a room. That makes the season a natural starting point for discussions that are far easier to delay than to begin.

Waugh does not recommend launching into a full estate or legacy review over Thanksgiving dinner. He sees the gathering as a chance to raise the subject and set up a more detailed discussion once the holidays are over.

“Having everyone together, typically during a happy time, can be a great way to begin discussing wishes, desires, and what matters most to the family,” Waugh said.

Caroline Wetzel, a vice president and private wealth advisor at Procyon in Shelton, Connecticut, said the hardest part is often simply getting started. The break from routine helps.

“Holidays prompt families to pause from their routines, gather across generations, and reflect on their shared history and expectations for the future. As a result, some families find that important conversations they’ve been meaning to have with loved ones can finally take place in the comfort of living rooms or in the quiet kitchen after a full day of activities,” Wetzel said.

What role should advisors play?

Many parents have never discussed finances with their adult children or grandchildren, Waugh said. Often that is because money was off limits in the homes they grew up in, and they are unsure where to begin.

“As advisors, we can help prepare both generations for those conversations and, when appropriate, facilitate a more structured family meeting. We can also help explain financial planning, clarify responsibilities, and make sure everyone understands the intentions behind the decisions that need to be made. Ultimately, it’s not our money or our place to make those decisions for the family, but it is our responsibility to help them make informed decisions and communicate those decisions effectively,” Waugh said.

Wetzel described the advisor as a neutral third party. The advisor helps clients put their wishes into words and pass them on to the people who will carry them out. Before a gathering, she helps clients decide whether to raise the topic at all, depending on who will be there. Not every relative needs every detail, she noted.

“After the holidays, advisors can initiate the follow up work required to facilitate meetings among family and with attorneys and tax professionals to clarify intentions and update documents,” Wetzel said.

Joe Buhrmann is an advisory financial planning practice management consultant at eMoney Advisor, a financial planning software provider. He said families routinely spend hours on the menu and gift list but little time on money.

“Many families spend hours planning the meal or buying gifts, but far less time discussing financially taboo topics like money and estate planning. Holiday gatherings can help normalize discussions around values, wishes, legacy, and financial responsibilities before decisions need to be made in a crisis. The goal isn’t to turn Thanksgiving dinner into an estate planning seminar … but it could be to begin a conversation that can continue over time,” Buhrmann said.

He recommends that advisors lead with values rather than technical estate concepts. They can ask clients how they hope to be remembered, or how their loved ones would manage if something happened to them, and then keep probing.

“And they can help clients keep the conversation moving with two simple prompts: ‘Tell me more …’ and ‘What else?’ If a client answers, ‘My nieces and nephews would probably inherit everything,’ then respond with ‘Tell me more about them.’ The first answer is rarely the whole answer,” Buhrmann said.

Building relationships with the next generation

Waugh also encourages clients to introduce their advisor to their adult children, even without any expectation of new business. That connection matters, given research on why family fortunes rarely survive the second generation.

“One of our responsibilities as advisors is to encourage clients to introduce us to their adult children, not necessarily to establish a business relationship, but simply so they have a familiar face and someone to call when the need arises. The reality is that eventually we’re all going to be gone, and when that happens, it’s already an emotional and difficult time for the family. Having that warm introduction ahead of time can make navigating those circumstances a little easier,” Waugh said.

Wetzel runs family meetings, planned sessions where relatives review a client’s wishes together, around a single topic.

“When I host family meetings, they are focused on a specific topic, are guided by an agenda that includes time for each family member to contribute to the conversation, and I share with all participants key takeaways and actions. We use these meeting summaries to drive our future activities and meeting topics. And lastly, I strive to engage each generation of clients in ways they want to be involved; from spending time in person socially to having impromptu phone calls when major life events are about to happen to texting on their birthdays, I want my clients to know that I am available, accessible, and that I care about them,” Wetzel said.

Buhrmann said a secure, shared digital planning space gives families a common starting point. It can hold documents, priorities and goals, and access can extend to attorneys, tax professionals or trusted relatives. Younger clients tend to be comfortable with technology, he said, so tools such as client portals, goal tracking and budgeting insights can build trust before any wealth changes hands. 

For Buhrmann, the opportunity outweighs the awkwardness.

“It’s a chance to discuss values, priorities, and the legacy they want to leave behind. The advisor’s role is often less about presenting answers and more about helping families start a conversation they’ve been meaning to have for years,” Buhrmann said.