Download our free probate checklist. Download now

The Conversation: Talking with your family about estate matters during the holiday season

The holidays are one of the few times the entire family gets together during the year. That also means it's a great time to talk about estate planning.

Estate planning conversation during the holidays

Preparing for “the talk”

As with any important conversation, arguably the most important part is getting prepared. This doesn’t mean just getting your facts straight or knowing where the conversation could head. It also means knowing yourself, too.

Know your facts

Talking about estate and financial matters can be highly complex. If you decide to dive into the chat head first without a proper understanding of how the estate process works, you’ll only work to confuse your loved ones.

We can’t stress enough how important it is to know exactly what you’re talking about and why you want to bring it up in the first place. We’ll address that second point below. First, here’s a quick reference list of some popular estate topics to help you get as educated as possible.

The Ultimate Guide to ProbateThe Estate Executor’s Checklist
How to Choose an ExecutorWhat is a Power of Attorney?
Main Tasks of an ExecutorWhy is Estate Planning Important?

In addition, here’s a list of definitions you can refer to when explaining how estate matters work; if your loved ones are not aware already:

TermDefinition
BeneficiaryA person or entity named in a Will or financial or insurance contract as the inheritor of the property when the property owner dies.
EstateRefers to all the assets of the deceased at time of death.
ExecutorThe person appointed in the will to settle the estate. The appointment in the will gives them the authority to do what is required to deal with the assets and debts of the estate as per the deceased’s wishes (where applicable). Can also be called Estate Trustee, Personal Representative, or Administrator.
IntestateThis term is used when someone dies without a will. It means that the estate doesn’t have an executor and someone will need to apply to be appointed as such by the court. This also means that what remains in the estate after all debts are paid is distributed according to the intestacy laws in the jurisdiction where the deceased resided.
Power of AttorneyAn authorization to act on someone else's behalf in a legal, business, or health matter while they are living. A power of attorney may be limited to one specified act or type of act or it may be general.
ProbateThe legal process where a person’s will is reviewed and validated by the court.
WillA legal declaration in writing by which a person, the testator, names one or more persons to manage their estate. This also includes providing instructions as to how their wishes will be carried out.

Examine yourself

Arguably even more important than understanding the facts is understanding yourself. Taking some time to review your motives for bringing up the topic will go a long way in making the interaction organic.

If you have already tried to broach the topic with your family members in the past, with only negative repercussions, taking this introspective pause is crucial.

By not examining previous frustrations from your last conversation, you may make the same mistakes again. Even worse, your approaching the topic while still harboring old irritations will be noticeable by your interlocutor(s) immediately and effectively shut down the conversation.

Take the time to ask yourself some questions as well, such as:

  • Are my motives for bringing up this topic selfish? (i.e. I want to see if I am in my parent’s will)
  • Am I in the right state of mind to discuss these often sensitive matters?
  • Am I under too much external stress?
  • Do I have my own estate planning done? If not, why?

Questions to ask

In addition to asking yourself questions, you also need to prepare some thoughtful (but not forced) questions for your loved ones to consider. Here are some solid examples:

  1. Do you have a will? If so, do you know where it is stored?

  2. Are there assets you are particularly concerned about going to specific people?

  3. If something happens to you, do you have plans in place for your dependents?

  4. Do you have anyone in mind to take care of your estate and ensure your wishes are followed?

One of the most sensitive topics is regarding who will receive the assets of the estate. Because asking such a question can make people uncomfortable, we recommend asking that further down the road. Once they are open to estate planning matters in general, then it is a good time to ask about specifics.

Starting the conversation

Use personal anecdotes

One of the best ways to immediately create an organic environment, and produce a genuine connection, is through stories. Using a personal anecdote–or one about a famous celebrity–allows you to set up the conversation without making it feel forced. Here are some examples:

  • Did you hear about Patagonia’s big decision to move their funds into trusts for environmental reasons? What do you think about that?

  • My partner and I got our wills, powers of attorney, and medical directives all done last week with our estate professional. We had a great time. Have you ever thought about doing that?

  • With inflation being as high as it is, one of my financially responsible coworkers mentioned looking into a family trust as a source of tax breaks. Have you heard anything similar?

Listen and respect them first, then speak

This is by far the most important piece of advice we can give you when it comes to having these kinds of conversations. Ready?

Listen to understand, not respond.

Too often–especially on social media–we are comfortable with listening to counter someone’s opinion and aren’t realizing (or care to realize) how that undercuts any relational connection we have established with that person.

When it comes to discussing estate matters, it is crucial to first listen to your friends or family members, respect their opinion and then respond; if appropriate.

Ultimately, they may not want the conversation to go further, which is okay. But, you need to respect their decision and be willing to simply hear them out, regardless of the outcome. Doing so will keep the relationship intact and healthy, so if they do decide to plan their financial future, they’ll turn to you for guidance.

Dealing with objections

Although you may have gotten the conversation going smoothly, and made sure you are as prepared as you can be, you aren’t out of the woods yet. Just as difficult as planning for the talk is facing objections from friends or family. Here are some common objections you might run up against this holiday season.

It’s too expensive

For many people–especially during a time of financial upheaval–legal matters are seen as unnecessary and too costly. In the case of some high-end probate lawyers, their objection about high costs hits the mark. But, that isn’t the only option for estate planning.

Many companies–ClearEstate included–offer cost-effective estate solutions that cost much less than the more traditional route. Estate planning is not synonymous with an expensive probate lawyer.

You just want to be in the will

This objection may stem from including questions about who the beneficiaries of the will are before listening to your loved one’s thoughts first. They need to realize that you care about them, and not just where their assets are going. Making sure to listen to them, and including questions about the beneficiaries at the end of the talk, will help make this objection come up much less.

Another way to deal with this objection is to offer proof of your motivations, as it is aimed at your reasons for bringing up the topic of estate planning in the first place. Offering reasons for your motivations being pure and altruistic (such as sharing concerns that their wishes regarding their assets won’t be realized) will help settle the situation. Offering a personal anecdote to organically strengthen your case is an even better approach.

It’s too complex and overwhelming

This final objection is one of the most common we hear at ClearEstate. Among the hundreds of statutes that govern estate law, the never-ending opinions about how to best avoid probate, feeling overwhelmed is the default reaction–for good reason.

From our own experience, the best approach is to ensure you hear and empathize with their concerns, rather than immediately try and fix them. Offering more information that simply adds to their stack of stressors may only make things work. Helping them work through those emotions and then offering advice will be much more effective.

Finishing the conversation

When it comes time to end the conversation, there are three possible scenarios.

First, the discussion goes poorly and your ideas get squashed.

Remember that this is healthy and a common occurrence. People need time to process preparing for their end-of-life decisions, as facing the fact that they won’t be around forever is quite unnerving.

It is crucial to not push them to discuss the topic further and simply give them space. The goal isn’t to bring them over to your side, but to merely get them thinking, and you’ve done that.

Second, the conversation goes very well.

Your loved ones are highly receptive to your information and advice and they decide to set up wills and other estate documentation right away. In this instance, congratulations! You’ve helped someone make one of the most important financial decisions they will ever make. But, be sure to not overdo it. Give them time to figure things out on their own time and help them along the way without suffocating them with advice.

Finally, the conversation doesn’t go anywhere or at least doesn’t lead to a concrete outcome.

Our family members might have listed to your advice, but did not respond much or didn’t show a receptive attitude. In this instance, our approach would be to give them time to process the conversation, but also not forget them either. Once some time has passed, be sure to kindly follow up with them and see how they react. That will give you a clear impression as to where they stand on the matter.

Final Thoughts

To conclude, the most important takeaway is to listen. Understanding where your family is at regarding their estate matters, and respecting their decision at the end of your conversation is crucial. At the end of it all, what matters the most is the relationship you have with those people, not whether they have a concrete estate plan or not.

Looking for some advice and information on how to approach estate planning topics with family and friends, or even get your will drafted? Contact one of our estate professionals for a free consultation. We would love to hear from you. Happy holidays from all of us at ClearEstate.

Probate Checklist Join the 10,000+ executors who have downloaded our blueprint to probate

Use our 12-step blueprint to probate, avoid settlement delays, and settle estates sooner.

Download yours for free!