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How to Talk With Your Loved Ones About Estate Planning

While most people think the “birds and bees” talk is the trickiest one to have with their family, we can think of one that seems even more daunting – the estate planning conversation.

After all, this is a talk that involves some of the most delicate subjects you can possibly navigate with your loved ones.

Death, money, illness, and personal relationships – they’re all necessarily involved in the “end of life” conversation, and they can be tricky topics for even the most well-adjusted family.

So, how can you bring up these touchy subjects if you’re looking to have a serious conversation with your older relatives about the details of their estate plan – or even trying to convince them to put a plan together for the first time?

Here are a few things worth keeping in mind as you prepare to have this important talk with your aging loved ones:

Find the Right Time

When it comes to broaching the subject of estate planning, there are many outlets on the web offering suggestions on the “how,” “when,” and “where” – and a few may well be worth keeping in mind.

For instance, this blog post over at Fidelity suggests that anyone wishing to start this conversation on the right foot should ”pick a positive, comfortable environment during a period of relative calm,” and “stress the importance and benefits of this conversation to everyone affected.”

Over at, another writer suggests that younger family members start the conversation “by talking about themselves,” which offers an in for a parent who may otherwise be reluctant to dive into their own affairs. This great article from Kiplinger offers similar suggestions, advising families to have the conversation “early and often,” and to “ease into the subject” by bringing up “recent news or a friend's story as a way into the conversation.”

Stick to the Most Important Topics

There are a lot of steps that come with the passing of a loved one. The probate process needs to begin, financial accounts and other assets need to be handled, funeral and burial arrangements need to be made, creditors and debtors need to be paid, and disbursements need to be handed out in line with the wishes of the decedent. And that’s just the tip of the iceberg.

As we said, it’s a lot to tackle, and it can be daunting to bring up all of these important topics at once (particularly when you’re dealing with a family member who’s hesitant to be having any sort of conversation on the matter).

Instead of trying to figure everything out all at once, it may be productive to narrow your focus, and only discuss a few of the most pressing topics at a time. Here are a few important questions to consider asking, which will give you much of the vital information you may need about your loved one’s estate plan, without overwhelming them or intruding on their privacy:

“Do you have an up-to-date will?”
According to one study, roughly half of all adult Americans don’t have a will in place. This is an important estate planning document, which names an executor, offers directives regarding the care of children and pets, and generally helps lay out the wishes of the deceased when they can no longer speak for themselves. Without a will, the probate process can be long and costly, and fail to give family members what they think they’re owed, since the estate will be divided along rules set up by the state.

It’s also important to remember that wills should be thought of as living documents, regularly updated to reflect the current status of your personal relationships and account for all of your important assets.  

“Have you named a power of attorney?”
Designating someone as power of attorney gives them the ability to make important decisions regarding medical, financial, and legal matters in the event that a person can no longer do so for him or herself.

Dealing with this important matter can help ensure that your loved one’s wishes are met with care and attention by a knowledgeable, invested party, and provide for a smooth transition when it comes to handling funds for medical expenses, real estate transactions, and other important costs.

“Do you have other advanced care directives set up?”
A health crisis can hit at any moment, incapacitating your loved one and preventing them from clearly communicating their wants and needs. For this reason, it is important that adults have advanced care directives in place, including naming a power of attorney or proxy for healthcare and leaving a living will, which dictates what will happen to a person in the event of a catastrophic accident or medical event.

“Have you thought about what you’re going to do with your financial accounts and assets?”
Are your loved one’s biggest assets held in joint tenancy with rights of survivorship (allowing them to bypass probate)? Have they set up a revocable living trust for certain assets? Have they considered naming transfer-on-death beneficiaries or authorized users to their financial accounts to help make sure that someone has access at all times? These are important considerations, which many overlook until it’s too late to do anything about them!

The bottom line? While it may not be a fun conversation to have, talking about your loved one’s estate plan with them is one of the most important steps you can take to get ready for the future – and ensure everyone’s peace of mind in the here and now.

On the other hand, failing to clearly communicate with your family about these important issues could conflicts, questions, and uncertainty down the line, leading to a more frustrating and costlier probate process. Bringing on a qualified, experienced probate and estate professional early in the process could help alleviate some of these concerns.

For any questions or worries about any matters relating to estate planning and administration, probate, wills, trusts, and power of attorney, Chicago Probate Law is here to be your resource. Don’t hesitate to drop us a line today to get the conversation started.

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