Family Discussions During the Holidays


Family DiscussionsWritten By: Kevin Reardon, CFP®

Family Finances & Holiday Cheer

The holidays are here and it’s time to get together with those you love the most. We can all picture the scene – the front door opens and people pour in. The family is together again. Perhaps your special guests include adult children, grandchildren, parents, in-laws or even Uncle Louie and Aunt Edna. There is food, drinks, laughter and lots of conversation. If your time together lasts only a few hours, soak up every second and be present in the moment.

For some, however, these get-togethers last for an extended period, perhaps even days. The lighthearted moments transition to in-depth discussions and possibly even moments of lengthy silence.  It’s in these extended moments where you have an opportunity to dive into meaningful discussions that many times get pushed to the back burner.

Before we review some important discussion topics, let’s address the elephant that all too frequently exists in these rooms. Some people believe it’s taboo to talk about finances, health, family dynamics and other sensitive issues. We all see the elephant sitting there and choose instead to talk about the weather or rehash an old family story rather than address important topics. This year, I encourage you to take a chance and open the door to what could be some of the best conversations ever had.

Listed below are starter questions and comments to open the door to meaningful conversations.


To ask mom or dad:

  • Do you work with a financial advisor? I would like to have their contact information so I know who to call when something happens to you.
  • My friends’ parents organized a family meeting to talk about their family finances and she said it was incredibly insightful and productive. What do you think about doing that with our family?
  • You mentioned providing some money to pay for your grandchildren’s college education. What did you have in mind so we can plan accordingly?
  • Have you purchased long term care insurance?
  • Where do you keep your financial records?

To ask adult children and in-laws:

  • How much life insurance do you have? I want to make sure you have enough to support our precious grandchildren if you or your spouse would die prematurely. If not, I’ll end up supporting them and that is not in my financial plan.
  • How much disability insurance do you have? My friend’s son had a health event recently and can’t work. He didn’t have disability insurance and it’s created a massive strain on the entire family, including his parents.
  • How much money are you saving each year? We struggled to save money when we were your age until our advisor put us on an automatic savings plan.
  • How much have you set aside for your children’s education?
  • Do you work with a financial advisor? If I could go back and do one thing differently, I would have talked to a financial advisor while I was younger.


To ask mom or dad:

  • Tell me about our family health history. My doctor asked and I realized I need to know more.
  • What medications do you take?
  • I wouldn’t mind coming to your next doctor appointment to learn more about how you are doing. Would that be OK?
  • When your parents were older, you had to take away their car keys. When will I know it’s time to do that for you?

To ask adult children:

  • Do you have any health issues I should be aware of?
  • Does your doctor know about our family history?
  • Have you had a colonoscopy, PSA or mammogram lately? (Age appropriate)
  • I need to tell you about some health issues I have been having.

Estate Planning

  • My financial advisor wants me to do some estate planning. What have you done in that regard?
  • Who is your Financial and Health Care Power of Attorneys (POAs)? Tell me about that.
  • Who is your executor and/or successor trustee?
  • Have you had discussions with your POAs and executor/trustee about your plan?
  • One of your children or grandchildren has special needs. Have you made any adjustments in your estate plan to ensure that person is not disqualified from federal or state benefits?
  • When I die, I’ve decided I want to be cremated/buried. Have you thought about that?
  • You are recently married/had a child/divorced/widowed/had a health event/inherited money. Do you have an updated estate plan?


  • What do you want to happen to the beloved family cabin or warm weather condo when you’re gone?
  • You have some personal items that various people may want. Have you given any thought to who gets your personal affects when you die? We want to avoid any family strain.
  • Some of your personal items are valuable (guns, fishing gear, stamps, coins, chinaware, silver, etc.). What do you want to happen to those things when you die?
  • If you had one wish for our family when you are gone, what would it be?


  • Where do you keep your passwords for the computer and various logins?
  • If you were to die next week, what’s the number one thing I need to know about your situation?

Although asking these questions may seem scary, it is amazing how people will open up once you give them the opportunity. After you’ve had one crucial conversation, they get easier in the future. In fact, the person you are talking to may become proactive in starting the conversation next time.

Of course, there are always a few people who think it’s “none of your business” to ask these questions or have these discussions. The reality is they could not be more wrong. If your parent or child gives you the cold shoulder, provides vague answers, or says “you just want my money”, explain to them why you are asking. Give them real world examples that reinforce the benefits of having these conversations now while everyone is together and in good health. Ask for support from others in the family. It’s possible your biggest supporter may be that person’s spouse or closest confidant.

It has been said that the meaning of one’s life can be measured by the quality of their conversations.  This holiday season, we encourage you to dig deep, ask the hard questions and start some meaningful discussions. The best gift you can give each other is peace of mind. If you would like additional resources that will help facilitate these conversations, reach out to your Shakespeare team.