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Home > Blog > Estate Planning > How to Approach Sensitive Estate Planning Topics Over the Holidays

How to Approach Sensitive Estate Planning Topics Over the Holidays


The holidays are a time for happy reunions with family members you may not see on a regular basis. As a result, it can also be the perfect time of year to bring up sensitive topics you may be reluctant to discuss over the phone or during other visits. The last thing on your mind may be matters pertaining to estate planning and end of life issues. However, holiday get togethers often open the door to these types of discussions and the following tips can help you guide the conversation.

Family Discussions About Estate Planning

If you are gathered around after a hearty Thanksgiving dinner or spending down time during an extended holiday weekend, it may present opportunities for important discussions pertaining to estate planning. Time warns that while families considering these types of conversations important, they often do not know when or how to have them. Bringing up issues related to wills, trusts, or advance directives directly may seem awkward, but there are ways to subtly steer the conversation:

  • Refer to an item that was left to you by a deceased relative and use it as a topic of conversation. “Grandma left me these dishes in her will and I am so grateful she did.”
  • Refer to an item you intend to leave to others. “It makes me happy to think that when I am gone, these goblets will still have a place at family gatherings.”
  • Ask broad, open ended questions that spark conversation about end of life issues: “What is the one thing you would want everyone to remember about you?” “What do you consider your most important accomplishment?”
  • Bring up a situation you have heard about from mutual friends or relatives. “Did you hear about ____? They died without a will and the family is struggling on how to handle their estate.”

These are all indirect approaches. Your other option is to approach the topic head on by suggesting a family meeting. Acknowledge that it may seem awkward, while emphasizing the importance of these discussions.

Bringing up the Need for Long Term Care

Holidays have the potential to highlight ways in which an older family member is struggling. Get togethers may reveal losses in functioning and abilities that indicate the need for more comprehensive care. The American Association of Retired People (AARP) recommends the following tips for addressing these issues:

  • State concerns in a loving, respectful manner;
  • Emphasize that your main goal is to be helpful;
  • Phrase your concerns as questions, such as asking how an older relative manages tasks;
  • Stay calm if they get defensive or angry.

It may take several conversations to actually reach a solution, but holiday discussions can open the door.

Contact Us Today for Help

At Cavallo & Cavallo, we know how challenging it can be to bring up certain topics and provide the caring, professional legal guidance you need in these situations, To discuss these matters with our New York estate planning attorneys, reach out and call or contact us online to request a one on one consultation in our Bronx or Westchester office today.




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