Not every news cycle adds clarity. This piece on 7 ways to kick off an estate planning talk with your parents aims to do exactly that: cut the noise, share the core facts, and offer a balanced read of the implications for individuals and small businesses.
Do you know anything about your parents’ estate plan? Do they have one? Do you know where it is?
You may assume they have one. Everyone gets one when they retire, right?
Not quite. Actually, not even close.
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more – straight to your e-mail.
Profit and prosper with the best of expert advice – straight to your e-mail.
USA Today says 52% of people over the age of 55 have no will in place. A study from Trust & Will broke it down by generation and found that 56% of Baby Boomers (born 1946 to 1964) and 34% of the Silent Generation (born 1925 to 1945) have no instructions for what to do with their assets when they pass away.
You may feel uncomfortable bringing up estate planning issues with your parents, but a few awkward moments could be the difference between them having an estate plan and not having one.
That being said, with sensitive conversations like this, your approach can have a huge impact on the outcome. If you bring up the conversation the wrong way, you run the risk of the whole thing going off the tracks before it even starts.
A lot of the time, the hardest part of having difficult conversations is just getting them started. With the right opening question, you can start things off on the right foot.
Here are seven questions that could help you start an estate planning discussion with your parents:
Question No. 1: Can you review my estate plan to see if I’m missing anything?
The least confrontational way to approach the estate planning conversation is by asking your parents to help you look at your own plan.
By creating yours first, you set the right example. Plus, you can tell them exactly how you did it, who you worked with and how easy it was.
My firm, Clarity Wealth Development, has created a beginner’s guide to estate planning that you may find useful.
Question No. 2: Do you have an estate plan? What does it include?
The second option uses the straightforward approach: Just ask.
Your parents may say yes, which is great. The second question (what does it include?) is an essential follow-up. They may think “estate plan” is just another term for a will, but it’s much more than that and includes:
Question No. 3: Have you ever heard of a legacy drawer?
More than 50% of people have no idea where their parents’ estate planning documents are kept. That’s where a legacy drawer comes in handy.
Have you ever seen those glass boxes on the wall in buildings that say, “In case of emergency, break glass”? A legacy drawer is similar, except it’s a place where you say, “In case something happens to me, look here.”
A legacy drawer doesn’t have to be an actual drawer. A lot of people use binders or safe boxes. For ease of access and security of the information, it should be a physical collection, not a digital one stored online.
Legacy drawers are intended to act as a physical place to put all of the important information people would need to know if you were gone:
- A list of all of your online accounts, from Spotify to Schwab, and where you have securely stored your passwords for them, such as a password manager
- Will and estate planning documents/instructions
- Financial accounts
- Funeral instructions
- Insurance information
- Letters to loved ones
- Any family secrets, whether it’s the secret ingredient in Nana’s chocolate cake or something heavier
- Other important documents such as your birth certificate and Social Security card
Question No. 4: What would you want us to do if we start noticing signs of incapacity in you?
This one may feel a little direct, but it lets your parents know that you’re planning ahead so you can take care of them in the way they want.
Almost 90% of people over the age of 65 want to continue living in their own home as they age, as reported by AARP. However, it has been reported that more than 20% of people over the age of 85 require help with basic daily activities (e.g., bathing, dressing), and 42% of Americans over 55 will develop dementia at some point.
Incapacity can be a tough topic to bring up, but someday you and your parents may be very glad you did. If one of your parents starts showing either mental or physical signs of incapacity, you don’t want to have to force them to move against their will. By discussing this openly with them before the fact, you increase the chances of everyone being on the same page.
Present this question in the context of the “emergency contact” info you add to medical forms. Who would your parents want you to contact in case of an emergency?
Your parents probably have a financial adviser, attorney, accountant, doctor, religious adviser, as well as friends they would like to be notified if they become incapacitated or die.
They could keep a “please notify” list in the legacy drawer.
Question No. 6: Do you have a safe-deposit box?
There has been a significant decline in the number of safe-deposit boxes in America, which makes it a great question to help open the conversation. (“I saw in the news that safe deposit boxes are disappearing. Do you guys have one anymore?”)
For a little context: In November 2024, The Wall Street Journal reported that “No one can find safe-deposit boxes anymore.” And in August 2025, Chase Bank announced that it was phasing out safe-deposit boxes at all locations nationwide.
Whether your parents have a safe deposit box or not, the question could lead to a broader conversation of how to handle their assets when they’re gone. (“You don’t have one? So where do you keep important items?”)
Question No. 7: What wisdom do you want to pass along?
If none of the other questions on this list seems like the right way to start a conversation with your parents, try this one.
While the other questions are very practical, this one is more introspective. By asking them for wisdom, you are showing love and respect while also encouraging them to reflect on the legacy they will leave behind, which can be a great lead-in for a broader estate-planning discussion.
It may feel difficult to start the conversation, but if it can help make your parents’ lives easier, you’ll be glad you did.
