Four Tips for Estate Plan Discussions at Holiday Gatherings

A younger woman and an older woman have a discussion while sitting at a table.

(Image credit: Getty Images)

published 22 November 2023

Believe it or not, the holiday season is right around the corner! Family members near and far are finalizing the details of their travel arrangements, excited to watch energetic grandchildren run around in their living rooms and have lively discussions with school-aged children about all of the new things they are learning and extracurricular activities they are engaging in.

For those thinking through their estate plans, these holiday gatherings present a unique opportunity to discuss their plans with their nominated representatives (e.g., trustee, executor, guardian). While walking through estate planning may not sound quite as exciting as the opening of presents, realistically, this is one of the few times when family members are all together each year, and it often carries plenty of downtime. Sideline conversations among subsets of adult family members surrounding familial issues such as estate and financial planning between multiple servings of dessert are incredibly common.

Having these discussions in person about potentially sensitive matters can ensure all parties are comfortable with their proposed roles in your plans. So, if taking some time around the fire to walk through your estate plan is something you’re considering doing this holiday season, here are four tips for handling these conversations in a way that is productive and won’t take away from all of the festivities.

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1. Start with a letter.

Before meeting in person, outline the role that you’ve nominated each individual for and your expectations. For example, a pet guardian may love your pets but may be unfamiliar with the concept of pet guardianship in estate planning. Consider something along these lines:

Dear Uncle Joe,

I hope you’re well. I’m writing my last will & testament and would like to name you as Pet Guardian. I’m sending you this letter to explain what that means. I’m looking forward to seeing you this holiday season, where I’d be happy to explain more.

What is a pet guardian?

Being named for pet guardianship usually means:

In the event I pass away before my pets, you will be responsible for giving them a home and taking care of them.
I would expect that you would treat my pets as companion animals, ensuring that they have a suitable home and are provided all appropriate diet, exercise, training and veterinary care.
These conditions generally apply to any pets that I have at the time of my passing, including those obtained after my will was written.

I know that you love my pets (and I know that they love you, too!), so when writing my will and thinking about this role, I immediately thought of you.

Love, Sally

2. Have a discussion face-to-face.

When the time is right (of course, avoid making an announcement at the dinner table) ask your family member to step aside with you. If possible, choose a more private or secluded location at a distance from the main festivities and comfortable for both of you. Refer back to the letter that you sent about the role you’ve nominated them for, explain why you’ve selected them for the role and answer any questions. Here is a script you can use to spark ideas and adapt to your specific situation:

Hi, Uncle Joe. Thanks for considering my request that you serve as pet guardian under my will. I know it’s a big responsibility. I chose you for the role because you are a pet lover and a responsible pet owner yourself, and I know that my pets — both Rover, the dog, and Felix, the cat — will be in good hands if I’m no longer here to care for them. I outlined some of my expectations for this role in the letter I wrote to you, but would like to answer any additional questions you may have.

3. Show them the relevant document.

If you are comfortable with it, let your nominee see the document in which they’re named. Consider bringing the document to the family gathering or having the conversation at the family gathering with an offer to show them a printout if that would be helpful. In estate planning, a little context can go a long way. Executors and trustees will want to know if they’ll be working with a co-executor or co-trustee and who that individual (or, if applicable, corporate entity) will be to make a decision if the dynamics will yield an effective working relationship.

4. Give them a chance to say no.

Make it clear that your nominee is under no obligation to serve in the chosen role. Let them know that even if nominated, they’re not obligated to serve. When the time comes, they can decide whether to accept this responsibility or not.

If they choose to decline, an alternate fiduciary can take over, and if no alternate is available, the probate court will appoint someone else to serve. If, however, they are already sure that they would prefer not to be named, let them know that’s okay, as well. Thank them for taking the time to consider the opportunity.

Having these types of difficult conversations during the holidays may not be the most joyous part of the gatherings, but they’re a significant act of love and compassion for all who make your life special.

So I hope you consider this opportunity to discuss your wishes with individuals you’ve selected to carry out key parts of your estate plan. When handled appropriately, these conversations can strengthen your plan and how your nominee feels about their role.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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Allison L. Lee is the Attorney-at-Law, Director Trusts & Estate Content for FreeWill, a mission-based public benefit corporation that partners with nonprofits to provide a simple, intuitive and efficient online self-help platform to create wills and other estate planning documents free of cost. Through its work democratizing access to these tools, FreeWill has helped raise billions for charity. Prior to joining FreeWill, Allison spent more than a decade in private practice.