8 Tips For Difficult Holiday Discussions

Over the next few months, most people will be spending at least a little, if not a lot, of time with immediate and extended family. This is a time you catch up, reminisce, and check in on how everyone is doing. It’s also a time when wills, estate planning, and long-term care begin to come up in conversation with aging family members, or really need to come up. Here are some tips to help make it less painful for everyone.

1. Gather information beforehand. Know what a will, trust, power of attorney, medical directive, Medicaid 5-year lookback, and signs of cognitive decline are, so you know enough to start the discussion.

2. Plan how you want to approach it and what your goal is. Is your goal to find out if they have a will? Is it to see if they are still able to care for themselves? Are you planning on just gathering information or offering support and advice? Know the goal so you know how to begin.

3. Choose an appropriate time. Four glasses of wine in is likely not the right time to start a discussion about death. (Or maybe it is for your family) Try to plan to start the conversation at a time when you will not be interrupted or distracted. You may also want to choose a time when other family members won’t be able to chime in with unhelpful anecdotes.

4. Prepare for the possibility that they are not ready or don’t want to talk about it. If you prepare for rejection, you will feel better about whatever information you are able to gather or wisdom you are able to impart.

5. Be honest and empathetic throughout the conversation. That may mean sharing your concerns and hearing their feelings as well. Often, people do not like to confront feelings of mortality or talk about planning for their own death. They will feel attacked if you tell them you are worried they can’t care for themselves or their house like they used to. Put yourself in their shoes before you comment and be kind. This is someone you love, and understanding where they are coming from will go a long way.

6. Actively listen to them. This means not being on your phone and not doing most of the talking. Make eye contact, nod your head, and tell them that you hear what they are saying. Make sure they feel heard.

7. Use “I” statements. To avoid having them feel attacked or ganged up on, make sure that your wording is done in a way like “I feel worried” or “I have concerns” rather than “You are worrying me” or “We are all concerned.” The conversation will not be able to move forward if you make them defensive.

8. Stay calm and focus on collaborating. If they begin to feel defensive or push back, just remain calm. Do not raise your voice or give them an ultimatum or guilt trip. Use some of the knowledge that you gained prior to the conversation to let them know how you feel and why it is important to you. Offer to take meetings with them and to help find the attorney, insurance agent, or long-term care team that will best suit them. Make the solutions a team effort and back off if it is upsetting them. Sometimes planting the seed now will lead to a conversation your can cultivate later.