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Wondering How to Talk to Your Aging Parents About Estate Planning? Here Are 7 Conversation-starting Questions That Could Help

Kim Hall

January 27, 2026

This article was originally published at Kiplinger.com

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. 

USA Today says 52% of people over the age of 55 have no will in place. Trust & Will did a study that broke it down by generation, and found that 56% of Baby Boomers (1946-64) and 34% of the Silent Generation (1925-45) have no instructions for what to do with their assets when they pass away.

You’re not the only one wondering how to talk to parents about estate planning. But even if you feel uncomfortable bringing up estate planning issues with your parents, keep in mind that 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 #1: Can you review our 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. 

You can learn more starting your own estate plan here.

Question #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 followup. They may think “estate plan” is just another word for a will, but it’s much more than that: 

  • Power of attorney
  • Healthcare power of attorney
  • Setting up a trust
  • Advanced directives around healthcare decisions (e.g., whether or not you want to be on life support)

Question #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:

  • Passwords to all of your accounts, from Spotify to Schwab – canceling accounts is a huge headache without login info
  • 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
  • You can also include other important documents like your birth certificate, Social Security card, etc.

Question #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 the way they want to be cared for.

While more than 90% of people over the age of 65 want to continue living in their own home, 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.

Question #5: Who would you want us to contact if something happened to you?

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 advisor, attorney, accountant, doctor, religious advisor, as well as a number of friends they would like to be notified if they become incapacitated or die.

They could keep a “Please Notify” list in a legacy drawer.

Question #6: Do you have a safe deposit box anymore? 

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 declared that “no one can find safe deposit boxes anymore,” then in August 2025, Chase announced that they are 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 #7: What wisdom do you want to pass along?

If none of the other questions on this list seem 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.

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Just Found Out You’re the Beneficiary of a Trust? Here Are 14 Questions & Answers You Need to Know

Just Found Out You’re the Beneficiary of a Trust? Here Are 14 Questions & Answers You Need to Know

If you have been named as a beneficiary of a trust, you probably have many questions about what comes next. Trusts can take many forms and may be governed by unique provisions established by the creator of the trust or “grantor.” As a trust beneficiary, you have certain rights. But to ensure that your financial and other interests are fully protected, you need some basic information about different trust structures and their management.

Trust Basics

At their most basic, trusts can be grouped into two broad categories – living trusts and testamentary trusts. A living trust is created by an individual during his or her lifetime. The grantor transfers property to a trust that is managed for the trust beneficiaries by a trustee. The grantor may act as trustee, or he or she may appoint another family member or family advisor, such as an attorney or accountant to be the trustee. A testamentary trust is established by will upon the death of the person whose assets it represents. Testamentary trusts can be used for many purposes; chief among them to provide for current and future beneficiaries.

In either case, it is the trustee who is charged with administering the trust in strict accordance with its terms. If this so-called fiduciary duty of the trustee is breached in some way, beneficiaries have the right to protect their interests by taking legal action against the trustee.

Role of the Trustee

Following is a brief overview of the trustee’s role and responsibilities.

• Asset collection and protection – Two of the trustee’s key responsibilities are collecting assets earmarked for the trust and ensuring the protection of those assets. For instance, if real estate is included as a trust asset, the trustee is responsible for the maintenance and upkeep of the property and maintaining appropriate insurance on the property. In the case of financial assets, such as cash or securities, the trustee must maintain one or more separate accounts on behalf of trust beneficiaries.

• Investment oversight – The trustee ensures there is a plan in place to address the needs and interests of current and future beneficiaries. Typically, trust investments are expected to generate income for beneficiaries while also retaining and reinvesting principal. In some cases, the trustee may have the authority to make distributions of principal to beneficiaries.

• Taxes – The trustee reports all income generated by trust assets and pays tax on any undistributed income as well as capital gains realized by the trust. In addition, the trustee informs beneficiaries of the amounts that they must report on their personal income tax returns as a result of trust distributions.

• Recordkeeping – The trustee is responsible for documenting every transaction that takes place in the trust accounts. Prior to final settlement, the trustee must demonstrate to the beneficiaries that all assets and income have been properly administered and distributed.

Beneficiary Right to Action

In addition to regular accounting of trust assets, beneficiaries have a right to request a special accounting from the trustee if there is reason to suspect a problem with the trustee’s performance of his or her fiduciary role. If it is found that the trustee is in violation of his or her responsibilities or fails to provide proper documentation of trust activity, then the beneficiary has the right to take legal action, including removing the trustee and requesting a replacement. Such action is normally handled by filing a petition with the local probate court.

Revocable vs. Irrevocable Trusts

Living trusts may be revocable or irrevocable. As its name implies, property held in a revocable trust may be “revoked” at any time; the terms of the trust may be changed and assets returned to the grantor. He or she can establish detailed instructions as to the handling of trust assets during his or her life and ensure continuity of management upon incapacity or death. Revocable trusts need not be filed in probate court after death, thus maintaining family privacy. However, the grantor will be subject to income and estate tax as if the property were owned outright.

In contrast, assets placed in an irrevocable trust are permanently removed from the grantor’s estate, and any income and/or capital gains taxes owed on assets in the trust are paid by the trust. Upon the grantor’s death, the assets in the trust are not considered part of his or her estate and are therefore not subject to estate taxes.

Irrevocable Trusts Offer Lifetime Giving to Beneficiaries

While requiring some loss of grantor control, a properly drafted irrevocable living trust allows individuals of substantial wealth to begin transferring assets to beneficiaries during their lifetime without incurring gift or estate tax. (Please note that a three-year survival period may be required in certan situations).

For example, the normal annual limit on tax-free gifts is $14,000 per beneficiary in 2015, an amount that may be indexed for inflation in future years. Under some circumstances, a taxpayer may include amounts above that in his or her unified estate and gift tax exclusion amount ($5.43 milliion in 2015 for an individual, twice that for a married couple, and subject to indexing for inflation in subsequent years). In addition, upon the grantor’s death, appreciation on the remaining trust assets is not subject to estate tax (assuming any three-year survival requirements are met).

Being named as a beneficiary of a trust is indeed a welcome event, but not without its complications and, if handled improperly, unfortunate consequences. For help understanding your rights and protecting your inheritance, it may be wise to engage the services of an experienced trust attorney.

Financial Planning Association
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