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4 Tips for Talking About Estate Planning with Your Family Over the Holidays

December 21, 2020

family in front of fireplace with stockings

With COVID-19 still raging, your 2020 holiday season may not feature the big family get-togethers of years past, but you’ll still likely be visiting with loved ones in some fashion, whether via video chat or in smaller groups. And though the holidays are always a good time to bring up estate planning, given the ongoing pandemic, talking about these issues is particularly urgent this time around.

That said, asking your dad about his end-of-life wishes while he’s watching football isn’t the best way to broach the subject. In order to make the talk as productive as possible, consider the following four tips.

1. Set aside a time and place to talk

Discussing planning while opening Christmas gifts most likely won’t be very productive. Your best bet is to schedule a time when you can all gather to talk without distractions or interruptions.

Be upfront with your family about the meeting’s purpose, so no one is taken by surprise and people come prepared for the talk. Choose a setting that’s comfortable, quiet, and private. The more relaxed everyone is, the more likely they’ll be comfortable opening up.

2. Create an agenda, and set a start and stop time

Create a list of the most important points you want to cover and do your best to stick to them. You should encourage open conversation, but having a list of items you want to cover can help ensure you don’t forget anything.

Also, set a start and stop time for the conversation. This will help keep the discussion on track and prevent people from veering too far off-topic. If anything important comes up that’s not on the list, you can always continue the discussion later. Remember, the goal is to simply get the conversation started, not work out all of the details or dollar amounts.

3. Explain why planning is important

Assure everyone that the conversation isn’t about prying into anyone’s finances, health, or relationships—it’s about providing for the family’s future security and wellbeing no matter what happens. It’s about ensuring everyone’s wishes are clearly understood and honored, not about finding out how much money someone stands to inherit.

Talking about these issues is also a good way to avoid future conflict and expense. When family members don’t clearly understand the reasoning behind one another’s planning choices, it’s likely to breed conflict, resentment, and even costly legal battles.

4. Discuss your planning experience

If you’ve already created your plan, start the talk by explaining the planning documents you have in place and why you chose them. If you’ve worked with me, as your Personal Family Lawyer®, describe how the process unfolded and how I supported you to create a plan designed for your unique wishes and needs.

Mention any questions or concerns you initially had about planning and how we worked with you to address them. If you have loved ones who’ve yet to do any planning and have doubts about its usefulness, discuss their concerns in a sympathetic and supportive manner, sharing how you dealt with similar issues whenever possible.

If you have not yet worked with us on your estate plan, consider setting up a free 15 minute consultation to learn what you might need to start the process, what you can do alone, and what I lawyer can best help you with.

For the Love of Your Family

With us as your Personal Family Lawyer®, we can guide and support you in having these intimate discussions with your loved ones. When done right, planning can put your life and relationships into a much clearer focus and offer peace of mind knowing that the people you love most will be protected and provided for no matter what. Contact us today to learn more.


This article is a service of Trinkl Estate Planning, S.C., Personal Family Lawyer®. We don’t just draft documents; we ensure you make informed and empowered decisions about life and death, for yourself and the people you love. That's why we offer a Family Wealth Planning Session™, during which you will get more financially organized than you’ve ever been before, and make all the best choices for the people you love. You can begin by calling our office today to schedule a Family Wealth Planning Session and mention this article to find out how to get this $750 session at no charge.

The information on this page is for educational and informational purposes only and does not create an attorney-client relationship. This information should not be construed to be legal advice.

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