Advisors say holiday meals can open the door to family finance talks

Holiday get-togethers can create an opening for estate planning conversations and help advisors strengthen relationships with younger generations.

As families come together for the holidays, financial advisors say the shared table can be one of the few places where long-delayed money conversations finally begin. The purpose, they emphasize, is not to wrap up an estate plan over dinner. Rather, it is to start a discussion that can later be turned into more formal planning.

The need is substantial. Fidelity Investments’ Family & Finance Study found that among parents age 55 and older with at least $500,000 in investable assets, 68% had not told their children what they would inherit, and 52% had not discussed their net worth with them. The larger wealth transfer is also looming: Cerulli Associates expects $124 trillion to move through 2048, with roughly $105 trillion going to heirs.

Advisors see those numbers as both an opportunity and a warning. Firms that never connect with clients’ children risk losing assets when wealth shifts to the next generation. That reality has pushed many practices to rethink how they retain heirs during the great wealth transfer.

Why the holidays work for these conversations

Kent Waugh, a Retirement Income Certified Professional and wealth planner with Accenden Wealth, Parkland Securities LLC and Sigma Planning Corp. in Colorado Springs, Colorado, said the holidays often bring several generations into the same room. That makes the season a natural time to begin conversations that are easier to avoid than to start.

He does not suggest trying to resolve a full estate or legacy review at Thanksgiving dinner. Instead, he views the gathering as a chance to introduce the topic and arrange a more detailed follow-up after the season.

“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, vice president and private wealth advisor at Procyon in Shelton, Connecticut, said the biggest hurdle is often simply getting the discussion underway. A break from the usual routine can help.

“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 advisors can do

Waugh said many parents have never talked about money with their adult children or grandchildren, often because finances were taboo in the homes where they grew up. That can leave them unsure of 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 said the advisor often serves as a neutral third party who helps clients put their wishes into words and share them with the people who will carry them out. Before a gathering, she helps clients decide whether the topic should come up at all, depending on who will be in attendance. She added that not every relative needs to hear every detail.

“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, advisory financial planning practice management consultant at eMoney Advisor, said families often spend plenty of time on menus and gifts but very little 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 advises starting with values instead of technical estate language. Advisors can ask clients how they want to be remembered or how loved ones would manage if something happened to them, then continue to explore those answers.

“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.

Connecting with the next generation

Waugh also encourages clients to introduce their advisor to adult children, even if no immediate business is expected. He said that matters because of the research showing why family fortunes often do not last beyond 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 also holds family meetings, which are planned sessions focused on one topic at a time and guided by an agenda that gives each relative a chance to contribute.

“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 can give families a common starting point. It can store documents, priorities and goals, and it can also be opened to attorneys, tax professionals or trusted relatives. Younger clients often feel comfortable with technology, he said, so client portals, goal tracking and budgeting tools can build trust before wealth is transferred.

For Buhrmann, the awkwardness is worth it.

“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.