Estate planning conversations are usually tough and probably not top-of-mind as families gather for the holidays. Discussing death and finances are often two of the most uncomfortable topics for families to talk about. Not talking about them, however, can lead to severe—and sometimes devastating—consequences.

While it might be difficult to broach the subject, the holiday season actually provides a great opportunity to talk to your family. Everyone is gathered in once place, opening the door to have important, distraction-free, in-person conversations. Many families take this time to share stories from the past, and celebrate what is to come, but these gatherings also provide the perfect canvas for heartfelt, emotional discussions. In fact, when to discuss estate planning during the holidays is a question many families overlook, and yet it is often the moment everyone feels the most connected. 

How to Approach the Conversation

Regardless of age, many adults delay the estate planning process, as it can be uncomfortable to contemplate one’s own mortality. Due to the delicate nature of the topic, conversations should also be approached delicately, and with the utmost respect for privacy and comfort zones. There are many ways to segue into how to talk about estate planning conversations during the holidays. Here are a few ideas to point you in the right direction.

• Start by having smaller conversations with other family members about their estate plans before going straight to mom and dad. This will allow you to test out the topic and determine how to best bring it up in a bigger group discussion.
• Wait for a good time to bring up your own experience with estate planning, or—better yet—ask the group for advice. This will open the door for a collective discussion about what documents your family has already put in place, and what still needs to be done. Do some research ahead of time, so you know what estate planning tools your parents should have in place. This will help direct the conversation, if you find that your parents do not have a comprehensive plan in place.
• Approach the conversation with empathy by leading with reassurance and care instead of diving straight into the details. Try saying something like “I want to make sure we’re prepared as a family if anything unexpected happens. It’s really important to me that your wishes are honored and that we can protect your legacy.”

Key Questions to Cover

When you finally sit down to have the estate planning conversation, it helps to come prepared. Instead of a rapid-fire checklist, think of these questions as a guide to help your parents open up, reflect, and share what they have or haven’t thought about.

• Have you already put together a will or trust? If so, when was the last time it was reviewed?
• Who have you chosen to step in for decision-making roles? Executor, trustee, financial power of attorney, health care agent.
  
• Do you have documents that outline your medical preferences? Advance directives, living will, HIPAA releases.
  
• Are your beneficiary designations up to date on life insurance, retirement accounts, and financial institutions?
  
• Have you thought about where you’d like to live long-term if care needs change?
  
• Where can we find important documents and information? Digital passwords, account lists, legal documents, and insurance policies.
  
• What fears or concerns do you have about the future, and how can we support you?

Documents & Tools to Have in Place

Here’s a straightforward checklist to help guide the conversation and ensure nothing is overlooked when thinking about how to create an estate plan:

Core Legal Documents

• Will
• Revocable or irrevocable trust (if appropriate)
• Durable financial power of attorney
• Health care power of attorney / health care proxy
• Living will / advance directive
• HIPAA authorization

Asset & Financial Information

• List of bank accounts, investment accounts, retirement accounts
• Insurance policies (life, long-term care, disability)
• Property titles and deeds
• Business ownership records
• Safe deposit box info

The goal of these discussions is not to pry or try to obtain information about your inheritance. It is to ensure that your parents have their estate plans in order, so that you and your loved ones aren’t left to contend with a probate nightmare after they pass. If you discover that they are ahead of the game, make them promise that they will revisit it every once in a while, to make sure it stays up to date with their situation and currents wishes.

If nothing has been done, suggest helping them research an estate planning attorney to get started and set up monthly check-ins to ensure everyone stays up to date on what has been done and any changes or updates. Having a plan in place will provide peace of mind that your parents are protected, and that your future won’t include a time-consuming, costly, and emotional probate battle. This is one of the best gifts your parents could give you this holiday season.

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