How to Start an Estate Plan Conversation

Estate planning conversations
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Having conversations about estate planning can seem unpleasant during the holidays.

Estate planning is not known to be a particularly happy topic.

It involves facing our shared human condition of certain mortality, let alone potential morbidity.

Most people simply prefer to ignore these facts of life.

According to a recent Forbes article titled “Holiday Season Tips For Caregivers,” failing to consider these realities in the context of estate planning can create problems for you and your loved ones.

Estate planning conversations are important.
The holidays can be a good time to have estate planning conversations.

It can leave family assets at the mercy of the government and caregivers unable to act according to the best interests of their aging parents.


With roughly $68 trillion estimated to be transferred by 45 million Americans through inheritances over the next 25 years, this is a weighty topic in both moment and money.

Just how weighty?

This is would account for the largest wealth transfer in U.S. history.

Additionally, the National Alliance for Caregiving (NAC) and AARP conducted research about the quantity of unpaid caregivers in the U.S.

At this time, nearly 50 million Americans fill this role.

The number has grown by 25 percent since 2015, with female baby boomers filling this role most.

As baby boomers continue to age, they will soon become those requiring care.

As a result, the number is expected to grow.

Because estate planning involves both incapacity and death planning, it is important to prioritize these conversations with loved ones.

How should one begin this discussion?

Schedule a time.

People make time for what is important to them.

Having a set schedule can help hold everyone accountable.

Additionally, no one will feel ambushed because they can mentally and emotionally prepare for the conversation about estate planning.

During this conversation, you can outline responsibilities and timelines for accomplishing estate planning goals.

Share your wealth of knowledge.

Do your research.

Understand the functions of different estate planning documents.

You should also be aware of the consequences of not having an estate plan in your state.

When having the conversations, underscore the value of being able to outline specific wishes to be followed.

Ask questions.

If you are not sure what estate planning your loved ones have done, ask them.

Using open-ended questions invites dialogue and conveys a non-critical stance.

You may find they have thought carefully about their wishes and why they have made their decisions.

Share your plan.

If you have an estate plan in place, sharing about your own wishes can be a good way to begin a discussion.

Doing so can normalize the process and reduce fears over the unknown.

Leave the conversation open-ended.

Be empathetic toward others when talking about estate planning.

They may be feeling many emotions and may not have had the chance to process these feelings to the extent you have been able.

Set an expectation of checking in for future conversations and any follow up accountability regarding what has been discussed and decided.

If your estate planning conversations have led you to a point of action, be sure to work with an experienced estate planning attorney.

Reference: Forbes (Nov. 29, 2022) “Holiday Season Tips For Caregivers”

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