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How to Use a Holiday Get-Together to Discuss Estate Planning

‘Tis the season to talk to loved ones about estate planning! Keep reading to find out why you should prioritize these conversations over the holidays.

As the holidays come around, we often see more of our family than we typically would get the chance to. The holidays are a great time to reconnect with our loved ones and have everyone within the same space despite our busy schedules. With everyone finally together in one room, it is a wonderful opportunity to discuss estate planning. Although estate planning may not be at the forefront of your mind during the holiday season, it is the perfect opportunity to get important discussions on the table when everyone can be present. 

Here at Trust and Will, we know that having estate planning conversations with your family members can sometimes feel uncomfortable. It can feel even more challenging around the holidays when everyone is catching up. However, with the holidays being an exceptional opportunity to have estate planning conversations, you will not want to pass it up. 

That is why we have assembled a list of tips about how to use a holiday get-together to discuss estate planning with your loved ones: 

Give a Heads Up

If you are feeling nervous about having the estate planning conversation at your holiday get-together, or are worried how your family might react, the best thing you can do is give everyone a notice in advance that you would like to talk about estate planning at your holiday party. This will avoid anyone being caught off guard and will also give them the chance, in advance, to think about topics they may want to bring up during the discussion. Otherwise, the conversation may fall short and leave many people feeling as if they did not have the opportunity to think about their own feelings and opinions before being asked. It will also eliminate any frustration that family members may have by not receiving a warning. 

Make Sure Everyone Has a Say

When having the estate planning discussion, it is vital that all family members are included. Otherwise, you will run the risk of having the family members who are left out of the conversation feeling frustrated, hurt, or angry that they did not get the chance to voice their opinion. In order to avoid this, when giving your family members a heads up that you want to have the discussion, also ask who will or will not be attending the family holiday gathering. For those who do not feel they will be able to make it, give them the option to call in or connect over Zoom to give them the chance to have their voices heard, as well. This will also help everyone to avoid any surprises on how family members would want estate planning handled.


To make any estate planning discussion meaningful and productive, it is important for you to enter into the discussion with a listening ear. Each member of your family will want the opportunity to speak their opinion and get a say in how the estate planning process will be handled. It is likely that you will not all agree but making sure that each person’s opinion is listened to and respected will make everyone much more open to compromises. If you do not feel that your voice is being heard, you will be less likely to want to reach a compromise as it may feel like your desires were dismissed. By listening, you will also be more likely to be empathetic to another perspective, making it easier to come to a compromise.

Be Honest

In addition to providing a listening ear, it is also important to be honest. If you are not honest with your family about what your desires are—such as mentioning that a specific sentimental item is important to you and you would like the opportunity to inherit it—you may leave the conversation with unaddressed concerns and harbor hidden resentment towards your family members for how the conversation turned out. There is no guarantee that you will always get your way in the estate planning discussion, but you will be sure to leave the conversation with no regrets of having not spoken up when it was important to you.

Do Not Expect to Solve Everything

It is necessary to remember when going into the estate planning conversation that not every issue can be resolved overnight. It is likely that you will need to have multiple conversations in order to solve more complicated matters among your family, especially if family members have strong opinions on specific matters. Additionally, it is important to remember that this is a holiday party in which you are bringing up the topic. People will not want to spend the entire time discussing estate planning. You will want to ensure there is room for catching up with your family members on what is going on in their lives. You do not want to devolve the entire evening into frustrating debates over estate planning matters. Know when it is time to table the discussion for a later date.

Estate planning can be a difficult topic to discuss and creating the plans themselves on top of this can sometimes feel like an insurmountable feat. Our team here at Trust & Will wants to help lighten the burden with our online, state-specific estate planning services. With our online services, it is easier than ever to create your own customizable documents. Through the affordable and easy-to-navigate website, you can create your Estate Plan all from the comfort of your own home. 

If you are having a hard time deciding where to start, take our free online quiz to begin. Get started today! Use a holiday get-together to discuss estate planning– and let Trust & Will guide you through the process!