How advisors can help clients on tough holiday conversations


The holidays can be a time of joyous gathering, but those gatherings can also generate considerable stress for clients — and by extension, their financial advisor. 

“I’ve had conversations the week after Thanksgiving with clients in the past, where the mother or father will call up and say, ‘My gosh, I’ve got three kids. They live in three different areas of the United States and they can’t agree on anything other than who gets the last piece of pumpkin pie!'” Andrew Crowell, a financial advisor who is the vice chairman of financial services firm D.A. Davidson, said in an interview. 

However, the winter holiday season can also be the perfect time for advisors to focus clients on their financial priorities and help their families create intergenerational wealth. 

“We are in a unique position to talk with the wealth creators about the future and about their concerns,” Crowell said, adding that families could use their advisor as a neutral outside party and a “bridge between generations” to mediate conversations. 

Advisors often have to step outside of their comfort zone to do this though, and step into family cultures in which conversations about money are often considered taboo. A study in April from financial services company Empower found that over half, 52%, of surveyed Americans never discussed finances growing up, and 63% don’t talk about money with their family. Research from Cerulli Associates earlier this year found that even among the wealthy, many parents fail to inform their children about their inheritances before their death. 

READ MORE: Wealthy investors do a lousy job of telling heirs what they’ll get: report

While some matriarchs, patriarchs or heirs may be anxious to buck that trend and spy a window of opportunity to do so in a family gathering, others are likely to dodge those attempts without a formalized setting for these conversations. Mainstream advice in the press this fall on handling relatives’ “intrusive” and well-meaning questions about one’s health, finances or romantic life consists of helping Americans find strategies to deflect, “keep it light” or “swivel” away from the topics rather than addressing the underlying issues head-on. That kind of avoidance and procrastination on key money-related questions can be destructive to a family’s finances. 

“If we as a profession take our stewardship of family wealth seriously, we need to be bold and open the door to even those awkward conversations,” Crowell said.

“If we don’t ask the question and there’s an ‘oops,’ it may be too late, at that point. So I don’t want any oopses on my watch.”  

Breaking bread, broaching the topic 
Most commonly around this time of year, these potential conversations can fall into a few different categories: health care and long-term care, estate planning and inheritances, and how to budget and handle family debt and holiday spending in the case of lower income families, Crowell said. 

For Chad Druvenga, advisors often find success in nudging clients along by framing the conversation the right way. 

“The emotion really is, a lot of people don’t want to be a burden to their kids,” he said. Especially when grown children live in other states, which he says is a common scenario, many clients will be moved to wonder what they should do in the event of a long-term care situation.  

READ MORE: Caregiving can sap retirement savings. Here’s how advisors can help

“‘What do you want to have happen? How do you want this to affect your next generation who’s going to take care of you?'” he said advisors can ask. “Once they’ve addressed how they want things to happen from an emotional standpoint, then let’s look at the logic” and compare products.  

Druvenga is the president and CEO of CBS Brokerage, an insurance brokerage firm that partners with advisors to help them find insurance and long-term care solutions for clients. He said in an interview that for clients who have extra assets they don’t need to live off of, advisors can help diversify those extra assets by discussing whether to put some into life insurance and give them a “floor,” instead of simply investing them to grow as aggressively as possible. 

“We spend a lot of time with advisors identifying whether from a math standpoint it can enhance the plan,” he said, adding that clients could also opt into concierge services for long-term care. 

Crowell said a good advisor can ask about liabilities, insurance and coverage, and even about clients’ health. “They’re willing to ask… ‘Were you to receive a diagnosis and require long-term care, memory care or physical care, what kind of coverage do you have?'” 

If a client pushes back, Crowell said the advisor can say: “I’m only asking you this out of protection for you and your family. I know it feels like I’m perhaps overstepping the bounds of our financial relationship, but I would not be doing my job where I’m not asking a question about preservation of assets, years from now.” 

Homes for the holidays 
Ron Strobel, the owner of fee-only RIA Retire Sensibly in Meridian, Idaho, said one of the toughest conversations he sees is “when the parents pass away and their adult children have to decide who will be the new host for their holiday gatherings.” 

“Adult children start hosting holidays for their own younger family members instead of gathering with their siblings and older relatives,” creating a schism, he said, adding that it happened on one side of his own family. 

Having a convenient meeting place for the extended family is also important to maintain a sense of unity, he said.

“My wife’s grandfather passed away about five years ago, and his children decided to keep his house as a place for gathering, even though nobody lives there any more. They maintain it as it was when he passed, and it provides a convenient meeting place any time the family wants to get together.” 

“Advisors can help guide clients through these scenarios by leading discussions about whether inherited houses should be sold,” Strobel said. “For some families, it might make sense to keep it.” 



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