How to Start the Estate Planning Conversation with Your Family

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Death and money are likely among the top two things you don’t want to talk about around the dinner table. Yet you probably know very well that an estate planning conversation is something you should discuss with your family sooner rather than later. Otherwise, your survivors may misinterpret or fail to follow your intentions, which is a huge no-no if you plan on creating a lasting legacy for your family.


So what’s the best way to get the estate planning conversation started?


For adult children (who probably feel like it’s none of their business to ask their parents such sensitive questions), you can start by asking your parents for estate planning advice on your own estate plan. In other words, “Hey Dad/Mom, I was thinking about (or recently completed) my estate plan and was just wondering if you had any input.” This is a great way to test the waters because, depending on how your parent responds, you can get a sense for their level of comfort in discussing such matters. If your parents start volunteering sensitive information about how they went about the process (or would go about the process if they don’t yet have an estate plan in place) then you can continue the conversation and gently move it towards the crucial point where it needs to be. This approach almost always works, but even it doesn’t then the worse case scenario is that they have little input and you end the conversation exactly where you started – no hard feelings.


For parents of adult children, you may be nervous that your kids will raise concerns about your estate plan that could then lead to disharmony. If this sounds like you, that’s all the more reason to have the conversation now while you still have a chance to alleviate any tension. While some may initially jump into “family announcement” mode and have the discussion over dinner, it’s probably best to start the conversation with each family member individually, if possible. If you have named any children as your fiduciaries (e.g., successor trustees or alternate agents under your health care proxy or power of attorney) then I’d start with them. By the way, you don’t have to talk about exact dollars values if you don’t want to. At least not initially. Instead, start with family values, hopes, and dreams: “this is what I want to do, this is why, and this is how I would like things to be done.” Resolve (or at least identify) all the issues individually first, then you can create a more organized approach to tackling these concerns in a systematic fashion either as a family or one-on-one. To be clear, I’m not saying you should be collecting votes on how things should be done, this is not a democracy (it’s your plan after all). But, by having the conversation you can ensure everyone’s on the same page as to what your intentions are and minimize future conflict.


For parents with minor children, it’s generally too early to have the discussion with your children about the nitty gritty details of your estate plan. In my experience, babies don’t care. Of course it’s never too early to instill family values by way of example, but for practical reasons your intentions only needs to be shared with your fiduciaries at this point. The biggest question being, “who do I want to raise my children if something were to happen to me and my spouse?” So first things first, come to an agreement with your spouse. Then I’d recommend either giving the person (or couple) a call with something along the lines of “Hey, I know this is super random, but my spouse and I are doing our estate planning and were wondering whether you would be comfortable taking care of our kids if something were to happen to us.” Nine out of ten times, the prospective guardian will be honored and immediately respond with “of course!” but before they have a chance to do that I would continue with something along the lines of, “I know this is a huge commitment so please feel free to think it over (or discuss it privately with your spouse) and I’ll follow up with you next week.” Once again, your prospective guardian will probably just say yes and leave it at that (in which case no follow-up call is necessary), but it’s best to give them a way out to ensure they are truly committed to being a guardian for your children rather than reflexively responding with a yes.


Lastly, if none of these options work for you, then just delegate the task to your attorney – they handle these conversations all the time. The attorney should have no problem leading the family meeting and looking like the bad guy if someone doesn’t like what they are hearing. After all, attorneys are used to being disliked by others – it’s part of their job.


If you have any questions about starting an estate planning conversation or about estate planning in general, then please feel free to contact Joseph Lento at Perennial Trust by calling (781) 202 – 6368 or emailing You can also download our Free Estate Planning Guide. Thanks for reading!

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