5 Tips to Handle Awkward Estate Planning Conversations

Tips on dealing with a very awkward conversation.

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Today we are going to look at a challenge that many of us face when we do our estate planning. What’s unusual — very unusual — about this particular challenge is this: I’m asked about it often, but, yet, I’ve never seen it addressed in a financial-planning book. To be honest, I’m not sure I’ve ever seen it addressed in any form.

C’mon, you’re intrigued, aren’t you? I’ve hooked you. I’ve pulled you in. You’re fixated on your screen. Okay, you’re mildly interested. Estate-planning experts are constantly — and wisely — telling us to pick the right person as our executor. And to pick the right person for our POAs. Those are tough roles.

The appointed person has to have many qualities. Choose the right individual. Don’t play politics. Don’t play favourites. Don’t worry about ruffling feathers. Don’t appoint co-executors and/or co-attorneys just to avoid upsetting someone by leaving them out. It’s all good advice. But geez. When you try to follow it, you quickly realize it’s not easy.

“Karen, we’d really like you to be our executor. Jeff, we’d really like you not to be our executor, but love your sweater.” Awkward. So, how do you handle those conversations? Delicate stuff. You don’t wanna harm your relationship with the unselected party or parties. And as important, you don’t want to in any way create ill feelings from them toward “the chosen one.”

Here are a few tips: 1) Have this conversation early. Don’t wait for a crisis nor for end-of-life. This will go over much better if it’s discussed when everyone is calm and everyone is healthy. The last thing we want to do is discuss this when people are already emotional. Emotions tend to make people more defensive, not what we want here.

2) Explain your decision based on your logic, and try hard not to come off as defensive or apologetic. Again, frame the decision around your logic, your reasoning that flows from the needed, specific skills and logistics. “Karen lives much closer. Sourov is a CPA, and you know, he’s a numbers nerd. Rosa has the time to take on all the work — and it’s a lot.”

Oh, and here’s something interesting: Several people have told me that bluntness interestingly, and humour have been a powerful combination here. “Mike, we love you to death, but let’s be honest, attention to detail is not your strength. You’ve lost your credit card 16 times, and remember when you showed up on time?

Neither do we.” 3) If you’re a couple presenting this info, form a united front. “We” language. 4) Reassure everyone about fairness. The executor carries out the wishes of the will, they don’t determine them. “All will be treated fairly. This has nothing to do with love or respect, as mentioned, it’s about logistics and skills match.”

And 5) Finally, do not make it a one-way conversation. Be open to questions and even criticisms. And if you’re still worried about all of this, get your spouse to do it.