The holidays may be the best time to talk to your parents about their Will because the whole family is in one place, in person, for a few days. A parent can say their wishes out loud to every child at once, which heads off suspicion later. Start small. A good first goal is knowing where the documents are.
By Ben Farrow, estate planning attorney, Anderson, Williams, & Farrow, L.L.C., Montgomery, Alabama | Provider attorney in the LegalShield network
“Mom, you’re gonna die. I want mine.”
That’s the worst way I know to talk to your parents about their Will. It’s also what a lot of grown kids are scared they’ll sound like, so they never start it at all.
I’ve practiced law for more than 30 years, most of it here in Montgomery, and I lead a lot of estate planning seminars. After almost every one, somebody comes up to me in the middle of a family fight and says, “I didn’t think we’d fight.” Then, almost always, “I wish Mom was still here so we could ask her what she wanted.”
I’ve seen this work, with families I’ve helped and in my own. The holidays may be the best time all year to start this conversation. Start it at Thanksgiving, and you still have time to act before the Dec. 31 deadlines.
You’re all in the same room, probably for a couple of days. These conversations are hard over the phone or on Zoom. On a call, you won’t see Mom tense up when the subject comes up. In person, you will, and you can slow down.
The end of the year is a time of reflection, and at a good family gathering you start with a lot of goodwill.
The biggest reason has to do with what causes the most pain in families down the road. It’s the thought that there was a conspiracy. Two siblings against one, or Mom against one. When a parent says, “I want the house to go to Jane,” in front of everybody, there’s no secret. Everybody knows it was Mom’s wish because she said it out loud.
If your family only gets together out of duty and everybody’s on edge, pick another time.
Ask about the plan and the paperwork, and leave the inheritance out of the first conversation. The biggest hurdle is being the one who says it first. Nobody wants to look greedy.
Think about the birds-and-bees talk. Most parents have it in the car on the way to soccer practice. The kids can’t get away, and nobody has to make eye contact. A walk works the same way. Take Mom on a morning walk before the turkey is served and say, “Hey Mom, I’ve been thinking about what you want to do with your stuff.”
Coffee before breakfast works too, and so does the porch at sunset. Keep it away from the food and the TV. Treat it like religion and politics, unless you want indigestion.
Then let the silence work. People hate a pause, but a pause gives Mom time to think about what she really wants to say.
Once you start, almost everybody’s relieved. The dread is what keeps people from doing it.
The person in your family who’s best able to bring it up. Sometimes it’s Mom or Dad, because they set the tone. Sometimes it’s one of the kids. If it’s the kids, they should talk among themselves first about who’s best to approach Mom.
Be careful with the one-on-one. One of the biggest things I see is a sibling who’s perceived to have pushed Mom into something. Usually it’s the child who lives close and takes care of her. Mom wants more to go to that child because that child was there when she needed it most. The siblings who live far away start to wonder. Probably nobody did anything wrong. But the mind goes to a bad spot when it doesn’t have information.
Parents can start it too. One family I know had four kids home for Thanksgiving. Mom handed each one a different color of sticky notes and said, “Walk around the house and put a sticky note on everything you’d want.” One heirloom might end up with four sticky notes. But now Mom knows.
Parents don’t know what their kids took away from childhood unless they ask. I’ll give you mine. My mom would never guess it, but I want her cookie sheets. My dad made nachos on them, and the melted cheese left a little pattern on the pan. I still remember it.
Knowing where your parent’s documents are. That’s an absolute win. I mean the Will, the Power of Attorney and the Advance Health Care Directive. A Power of Attorney names who can handle someone’s money and bills if they can’t. An Advance Health Care Directive says what medical care they want if they can’t speak for themselves.
Bonus points if Mom can show them to you. You don’t have to read them. Just make sure they’re signed. An unsigned Will is no Will at all. An unsigned Advance Health Care Directive is just a piece of paper.
Here’s how I’d handle it this year.
Uncle Sam’s deadlines are Dec. 31, and they’re real. Some of them won’t apply to your family. The ones that do won’t wait for January. Your parents’ documents are different. A Will or an Advance Health Care Directive is good from the day it’s signed, whether that’s Dec. 31 or Jan. 1.
Start with gifts. There’s a yearly limit on what one person can give another before the federal gift tax rules kick in. In 2026, the IRS sets it at $19,000 per person. If your parents are fortunate enough to give you or the grandkids $19,000, they could give $19,000 on Dec. 31 and another $19,000 on Jan. 1. That’s $38,000 across two tax years without going over the limit. If they wait until January, both gifts land in the same year.
Going over usually means filing a gift tax return, and most families won’t owe the tax.
Retirement accounts have a deadline too. Once your parents reach a certain age, the IRS requires them to take a minimum amount out of a traditional IRA or 401(k) every year. That’s called a required minimum distribution. After the first year, it’s due by Dec. 31. Miss it, and the IRS can charge a 25% excise tax on what wasn’t taken, or 10% if it’s fixed within two years. Parents 70½ or older who give to charity straight from an IRA, through what the IRS calls a qualified charitable distribution, also have to finish it by Dec. 31 for it to count this year.
A holiday visit is a good time to ask, “Have you taken your distribution this year?” It’s an easier question than “What’s in your Will?” And it opens the door to the rest.
That’s the other reason I like the holidays for this. Thanksgiving is about five weeks before Dec. 31. If the conversation turns up a gift you want to make, a distribution nobody has taken or a document that was never signed, you still have time to get it handled before the year ends.
The most common is the secret plan. People are afraid to say it out loud. They’d rather be gone and have the kids read it later. That’s when the suspicion starts.
Families also forget the sibling who isn’t there. I know a family with six kids spread across four states. Dad told them what he wanted. When he died, the family still split into a group of 3, a group of 2 and 1 on his own, partly because they hadn’t talked enough while he was alive.
And some people try to finish it all in one sitting. You don’t need to. Nobody’s locked in because they said something at Thanksgiving, and people change their minds.
Everybody wants to talk about it. It just takes one brave person to open the door.
Before anyone signs or changes anything, have a licensed attorney look at your family’s situation. That can be a LegalShield provider attorney or your own lawyer.
No. It’s usually easier to talk about someone else’s plan than your own, because yours makes you think hard about your goals. Talking with Mom or Dad about theirs may help you sort out yours. As my mom says, “I’ve never been this old before.” Try asking, “What do you wish you’d done differently at my age?”
An Advance Health Care Directive, which in many states includes a Living Will. A Will works after you die. A Living Will covers the gray area where you’re alive but can’t speak for yourself, and it says what medical care you want. Without one, your family has to piece your wishes together from emails and texts. That’s very hard on the people you love.
No. I’m the middle child, and I’m the one in charge in my family because I’m the lawyer. The person who handles things should be the one most capable, and a Will lets you name that person.
Ben Farrow is a partner at Anderson, Williams & Farrow, LLC, a LegalShield provider firm. Licensed in Louisiana, Alabama, and Mississippi, Ben has been the firm's supervising attorney since 2003 and provides advice and counsel to LegalShield members every day.
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