How to Talk About Money (and Estate Plans) with Loved Ones

Pew Research Center found in September 2025 that only about a third of American adults have created a will (32%) or a living will or advance health care directive (31%). And among older parents, only 44% had discussed with their adult children where they would want to live if they could no longer live independently. The most practical question is the one families skip. 

The holidays put everyone in the same room, and often become the time when these aging changes are more noticed and these concerns come about. If that happens to you this season, here are six steps to help you have that all-important discussion when the time is right. 

1. Start With What You Noticed, Not With the Documents 

"Do you have a will?" lands as an audit, and it puts a parent on the defensive. 

  Lead with the moment instead: "I have been thinking about you lately, and I realized if something happened I would not know who to call or what you would want. Can we talk about it sometime this fall?" That makes the conversation about your worry rather than their decline. Expect to raise it more than once. A first mention that gets deflected is not a failure; it is a seed. 

2. Pick the Right Time — and It Is Not the Dinner Table 

Holiday meals are crowded, emotionally loaded, and come with an audience. What the holidays are good for is proximity, so schedule the real conversation around the visit: the morning after, a drive, a walk. If there are siblings, a reasonable path is one initial conversation with your parents, followed by a family-wide one once they have agreed to talk. 

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3. Ask What They Want Before You Talk About What They Have 

Values first, numbers later. A few questions to ask aging parents: What would a good outcome look like for you if your health changed? Would you want to stay in this house, and what would have to be true for that to work? Is there anything you are worried about that you have not told anyone? 

4. Cover the Four Documents, Including Where They Are 

The estate planning documents checklist is short. A will directs what happens to assets and names an executor. A durable power of attorney lets someone handle financial matters if they cannot; without one, the alternative is a court conservatorship, which is slow, public, and expensive. A health care proxy, paired with a living will or advance directive, names who makes medical decisions and records what care they would want. And beneficiary designations on retirement accounts and life insurance control who receives those assets, regardless of what the will says. 

That last one is the quiet troublemaker. Designations are frequently decades out of date, naming a former spouse, a deceased sibling, or no one at all. Checking costs nothing. And existence is not enough: ask where the originals are kept and who else knows. If your parents are weighing whether to give now or later, see our guide to gifting vs. inheritance. 

5. Make the List of Who to Call 

Build a simple contact sheet: the estate planning attorney, the accountant, the financial advisor, the insurance agent, the primary care physician. Add where the accounts are held, whether there is long-term care insurance, and how bills get paid. 

Do not skip digital access. Many families discover after a crisis that nobody can get into the email account that receives every statement and password reset. A password manager with an emergency contact solves that. 

6. Decide What Happens Next — and Put a Date on It 

A conversation without a next step tends to evaporate by January. Before you leave the room, agree on one concrete action and when it will happen. Small and scheduled beats comprehensive and someday. This is the point I come back to with families more than any other: action is the best remedy to anxiety. 

Bonus Tip: You Do Not Have to Be the One in the Middle 

If the conversation feels loaded, and with siblings, second marriages, or a family business it often does, bring in a neutral party. In a joint meeting with the family's financial advisor, the advisor asks the uncomfortable questions and everyone hears the same information at the same time. We host these meetings regularly, for parents and adult children alike. 

A Note for Connecticut Families 

Connecticut's estate and gift tax exemption is $15 million per person in 2026, matching the federal amount, so most families here will owe no estate tax. But Connecticut is the only state with its own standalone gift tax, and its estate filing requirements apply broadly to resident estates even when nothing is owed. Make sure someone knows a filing has to happen and who is responsible for it. 

One Conversation, Then the Next One 

You are not trying to solve everything before dessert. You are trying to move the family from "we have never talked about this" to "we have started, and here is what happens next." And if you are the parent reading this, you can spare your children the awkwardness by raising it yourself. 

At WHZ Strategic Wealth Advisors, our Plan Well. Invest Well. Live Well.™ process is built for this kind of multi-generational conversation. Schedule a complimentary discovery session at whzwealth.com or call us at (860) 928-2341 to set up a family meeting before the holidays. Together, we can help your family move forward with Absolute Confidence. Unwavering Partnership. For Life. 

Authored by Holly C. Wanegar, CFP®. AI may have been used in the research and initial drafting of this piece. WHZ Strategic Wealth Advisors does not provide legal or tax advice. You should consult a qualified estate planning attorney or tax professional regarding your individual situation. This material is for informational and educational purposes only and is not a recommendation to buy, sell, or hold any security or to pursue any specific planning strategy. Estate and gift tax figures cited are for the 2026 tax year and are subject to change. Estate planning documents and their requirements vary by state. Investments are subject to risk, including the loss of principal. Securities and advisory services offered through Commonwealth Financial Network, Member FINRA/SIPC, a Registered Investment Adviser. 697 Pomfret Street, Pomfret Center, CT 06259 and 392-A Merrow Road, Tolland, CT 06084, 860.928.2341. http://www.whzwealth.com. 

RELATED FAQs

How do I bring up money and estate planning with my aging parents? 

Start with what you noticed and how it made you feel rather than with a question about documents. Saying “if something happened I would not know who to call or what you would want” frames the conversation around your concern instead of their capability. Expect to raise it more than once; a first attempt that gets deflected is normal. 

When is the best time to have a family financial meeting? 

Late fall works well because the holidays put everyone in the same place. Use the visit for proximity, but schedule the actual conversation outside the holiday meal — a morning walk, a drive, or a quiet hour works far better than the dinner table with an audience. 

What documents should every family know about? 

Four: a will, a durable power of attorney for financial matters, a health care proxy paired with a living will or advance directive, and up-to-date beneficiary designations on retirement accounts and life insurance. Just as important as whether they exist is whether anyone knows where the originals are kept. 

Why do beneficiary designations matter so much? 

Retirement accounts and life insurance pass by beneficiary designation, which overrides whatever the will says. These forms are often decades old and may still name a former spouse or someone who has died. Reviewing them costs nothing and is frequently the highest value item in the entire conversation. 

How many Americans actually have a will? 

According to a Pew Research Center survey of 8,750 U.S. adults conducted in September 2025, about 32% have created a will and 31% have a living will or advance health care directive. Even among adults in their 60s, fewer than half have a will. 

What question do families most often forget to ask? 

Where a parent would want to live if they could no longer live independently. Pew found that while about two-thirds of older parents had discussed funeral and medical care preferences with their adult children, only 44% had discussed future living arrangements — the most practically consequential question of the group. 

Should we include a financial advisor in the family conversation? 

It often helps, particularly when siblings, second marriages, or a family business are involved. A neutral third party asks the uncomfortable questions so no family member has to, and everyone receives the same information at the same time, which reduces later disagreements about what was decided. 

Does Connecticut have an estate tax my family needs to worry about? 

Connecticut’s estate and gift tax exemption is $15 million per person for 2026, matching the federal exemption, so most families will owe no state estate tax. Connecticut is, however, the only state with a standalone gift tax and has its own estate filing requirements, so a Connecticut estate attorney should confirm what applies to your family.