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Make it Awkward

If there is one “promise” I hear from potential clients more than any other, it is their assurance that they will come and see me “after the first of the year.” New Year’s Day is surely some kind of magical cutoff, after which clarity and pragmatism appear like so many unicorns to drive everyone into the local attorney’s office—after they hit the gym, of course—for a little estate planning. I have to ask: What are y’all doing in the meantime?

With the holidays quickly approaching, I assume that you are preparing to create a little of this family magic around the dinner table. What better moment could there be for informing Sweet Sally that she won’t be inheriting your antique silver tea set because you sold it on Ebay to help yourself buy a Cadillac? And the cranberry sauce will certainly help Ungrateful Gary swallow the news that you’ve cashed in your whole life insurance policy to afford the new drapes. Perhaps you’ve been holding back that the house is subject to a reverse mortgage so you can release it strategically, sometime between mashed potatoes and Aunt Helen’s pecan pie. But whatever your situation, I am quite sure you have decided to utilize these family dinners to help you prepare for our fast-approaching January meeting.

If you hadn’t planned on talking through your estate plan with loved ones this year, let me help you create a smooth transition to the topic instead of setting off a food fight. Below are some tips for including your holiday visitors (children, grandchildren, and siblings) in what I hope will be our productive January planning meeting.

1. Ask, Don’t Tell. If you have never discussed estate planning with your family, you don’t just get to spring a finished plan on them and expect NOT to create a scene. (E.g., see Danny Glover in the below movie scene.) While I am not suggesting that you need anyone’s permission to decide how best to dispose of your property or take care of your family, it may benefit you to assess everyone’s expectations prior to visiting my office. In fact, a lawyer should not be the first stop for most people.

Step one should probably be to ask questions about your family’s desires and expectations surrounding your own aging and/or death. Do the kids expect to inherit money? Are they okay with taking care of your vast collections of Boyd’s Bears in the event of your death? Did they have an emotional attachment to a particular item of yours? How did they envision your long-term care needs being addressed? Do they have their own financial plans that could be affected by an inheritance? Without announcing any of your own decisions, let them talk about theirs. You may be surprised to learn that their expectations do not align with your early planning at all.

2. Respect the Consensus. When all (or most of) your kids are in agreement on certain points—such as a desire to keep a piece of property in the family—and it doesn’t line up with what you were planning, try to see it from their angle before blowing past it. If they all agree, chances are there have been discussions behind the scenes. They share some goals. Use this: ask them if they have a plan in mind to make it work!

For example, if you had planned to sell the family home to help finance your assisted living plan, perhaps a child or another family member would like to purchase it at fair market value. If they didn’t know about your financial needs, discuss inviting a long-term care specialist to a later family meeting to help explain the advantages and disadvantages of following their shared wishes. But don’t write them off out-of-hand: wherever you have an agreement between potential heirs, using that agreement may prevent conflict between the heirs when the plan goes into effect.

3. Never Mind the Details, Pass the Pie! Do not allow a holiday dinner to descend into discussions about whose name goes on the serving bowls. Keep a high-level overview of the family's priorities at the fore.

Set some ground rules up front and keep it light. Perhaps while setting the table, you could let certain wise family members know that you want to approach sensitive topics about aging and death. Let them know how you will signal when it is time, and give them a safe word to call you off if necessary. Have them help you enforce the boundaries and keep the discussion on track.

For example, let’s say your sister is your best friend. “Janie, I’m going to ask the kids some questions about how my trust needs to be set up, but I need you to help me cut it off if things get tense. If you see Pete’s wife starting to fume, I need you to ask me for the dairy-free creamer and lay the smack down while I’m out of the room.” If you need to tackle these conversations in smaller groups or one-on-one, try to plan a walk around the block, a trip to the store, or another shared holiday task that you can do with one or two family members at a time during their visits.


I am not a therapist, I’m just a lawyer. You know your family better than I do—and perhaps yours is not as morbid as mine! If you have never talked at all about death and dying, you might find even the mere suggestion of any of the above objectionable. But I can promise you this: if you never discuss anything at all, you can be sure that the stuffing will hit the fan at some point. You may not be around to see it, but the unprepared family will not stay together and dine in harmony.

See you in January! And for the record, sweet potato casserole is my favorite.

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