Three Big Questions to Ask Your Aging Parents

Every few months, someone sits across from me looking exhausted. Not financially exhausted, but emotionally exhausted. They’ve just come through a crisis with an aging parent, and somewhere in the fog of hospital visits, legal scrambles, and family tension, they say the same thing: “I wish we’d talked about this sooner.”

I get it. These conversations are awkward. Your parents don’t want to feel like they’re losing control, and you don’t want to seem like you’re circling the inheritance. But if you wait until there’s an emergency, you’re making decisions under the worst possible conditions.

If your parents are in their seventies or beyond and you haven’t had these talks yet, consider using your next visit as the opening. You don’t need to cover everything at once. But you do need to start.

Where do things stand financially?

A client of mine, let’s call her Susan, assumed her mother was fine. Nice house, comfortable lifestyle, never asked for help. Then Susan’s mother had a stroke, and Susan discovered the house had a reverse mortgage she didn’t know about, credit card bills had been piling up for months, and nobody knew the login to the bank account.

You don’t need your parents to hand over their statements. But you should know the basics: Are they living off Social Security, a pension, investment income, or some combination? Are bills getting paid on time? If something happened tomorrow, would you know where to find the important paperwork?

Now, if they’ve named you as executor of their estate, that changes things. In that case, you really do need to see statements and have a full picture of what they own and what they owe. You can’t settle an estate if you’re hunting for accounts you didn’t know existed.

And while you’re at it, ask about usernames and passwords to important websites. The bank, the brokerage, Social Security, Medicare, utility companies. Write them down and store them somewhere secure. When the time comes, you’ll be grateful you did.

If the logistics are getting hard for them, autopay can be a lifesaver. So can simplifying down to one bank account and one credit card so there’s less to track. And if you’ve noticed signs of cognitive slippage, that’s worth a gentle conversation about seeing a doctor. Denial doesn’t age well.

The other thing to sort out: who has power of attorney to manage their finances if they can’t? That paperwork takes time to set up properly, and banks can be remarkably difficult about honoring it even when it’s in place. Don’t wait until you need it.

What’s the plan if something happens?

Nobody wants to talk about dying. But if your parents don’t have a will, the state gets to decide who inherits what, and that rarely matches what they would have wanted. I’ve seen families torn apart over a house, a car, even who gets the photo albums.

A will is the starting point. But there’s more. Beneficiary designations on retirement accounts and life insurance policies override whatever the will says. If your dad remarried and never updated his IRA beneficiary from his first wife, that’s where the money goes. I’ve seen it happen.

Then there’s the healthcare side. A healthcare power of attorney lets someone make medical decisions if your parent can’t. An advance directive spells out what kind of care they want at the end of life. Without these, you could end up in court while your parent is on life support, arguing with siblings about what Mom would have wanted.

And yes, ask about burial wishes. It feels morbid, but it’s a kindness. The last thing you want is a family argument at the funeral home.

Can they still live where they’re living?

Most people want to stay in their homes as long as possible. That’s understandable. Home means independence, memories, identity. But wanting to stay and being able to stay safely aren’t always the same thing.

Can they handle the stairs? The yard work? What happens if they fall and nobody’s there? For some families, a few modifications solve the problem: a bedroom on the main floor, grab bars in the bathroom, a medical alert device.

For others, the honest answer is that the house doesn’t work anymore. That’s a harder conversation, especially if they’ve lived there for decades. But I’ve found it helps to frame it around what they gain, like proximity to grandchildren, less maintenance, and built in community, rather than what they’re giving up.

If they’re not ready to move, at least get to know their neighbors. Exchange phone numbers. In an emergency, those relationships matter.

Start small

Your parents may not be ready to talk about all of this the first time you bring it up. That’s okay. The goal isn’t to check every box in one sitting. It’s to open the door so the next conversation is easier.

And if you’re the one in your seventies reading this, the same advice applies in reverse. Your kids don’t want to guess what you would have wanted. Tell them.

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