How To Tackle Estate Planning Conversations During the Holidays and Beyond
Written by
Cynthia Measom
Edited by
Rebekah Evans
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Thinking of capitalizing on family time during the holidays? It might also be the best time to have meaningful discussions on estate and other financial planning.
“The holidays bring families together and it’s also a time when people reconnect with relatives they haven’t seen in a while,” said Kevin Frankel, attorney and LegalShield provider. “This can bring awareness to health issues or signs of declining health that might not have been on anyone’s radar before. It’s a natural moment to start thinking about the future and planning for what comes next.”
Whether it’s the holidays or after, here’s how to tackle estate planning conversations.
How To Initiate These Discussions
“It can be helpful to bring it up, but in a way that feels natural — maybe by asking or gently suggesting a conversation,” Frankel said. “Timing is everything; if the mood feels right and everyone is relaxed, it could be a great time to start the discussion.”
Strategies for Successful Conversations
“Having difficult estate-planning discussions with family members can be more manageable with a thoughtful approach,” Frankel explained. He suggested utilizing the following strategies when having estate planning discussions.
Start With General Goals
“You don’t have to dive right into the details — starting with general goals, like protecting the family’s future or making things easier for loved ones, can create a positive foundation,” Frankel said.
Prioritize Shared Goals
It’s also important to bring everyone together.
“Focus on shared goals, such as ensuring fairness and avoiding future conflicts, while emphasizing the benefits of planning for everyone involved,” Frankel added.
Ask for Help From a Third Party If Needed
If there’s a history of conflict between family members or if it seems like this particular issue won’t be resolved easily, consider outside assistance.
“If it’s hard to keep the conversation neutral, having a professional, such as an attorney or advisor, present can help guide the discussion productively,” Frankel said.
Be Forthright and Organized
“Setting clear expectations with an agenda can keep the discussion focused,” Frankel said.
Be Gracious
“Finally, thank everyone for their willingness to engage in such an important conversation,” Frankel added.
How To Deal With Political Divisions
Frankel said that political divisions can complicate family dynamics. However, he pointed out that setting ground rules helps.
“Try explaining that the discussion isn’t about ‘you’ or ‘me’ but about the family as a whole,” he explained. “Emphasize the need to leave unrelated emotions or conflicts outside of the conversation.”
Who To Invite
“Include the people who will be directly impacted, such as immediate family members or anyone named in the plan, such as agents under power of attorney, a healthcare executor or a trustee,” Frankel said.
However, he added that it’s best to keep the group small and focused to avoid overwhelming the discussion.
How Much Time To Allow
According to Frankel, there’s no set amount of time that applies to estate planning.
“Estate planning is a fluid discussion with many moving parts, so it’s often best to start with one meeting to gather input and outline goals and then have follow-ups as needed,” he said. “This keeps the process manageable and allows everyone to think things through.”
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