Conversation Starters for Holiday Talks with Your Aging Parents

Community Manager
Community Manager
4 Comments (4 New)

 USAA Community Questions for Aging Parents.jpg

Just get the ball rolling.


When it comes to conversation, sometimes the biggest challenge is getting things started. At least, that’s the case in my experience. And things can be even more difficult if your broaching an uncomfortable topic, like your parents morphing from their life-long role of caregiver to someone in need of care.


Getting a handle on things should begin with some frank conversations before the family hits crisis mode. But, but how do you kick them off? There’s nothing quite like grinding through a laundry list of yes or no questions. With that in mind, here are six open-ended questions to kick off those important discussions with your aging parents:


  1. Tell us about your “what-if” game plan? I wrote “what-if,” but “when” is a more accurate characterization. Your parents probably have at least an idea of what they would like to see happen if they are incapacitated or pass away, but a mere idea isn’t enough. To make things happen according to their wishes, they will need to draft or update a suite of legal documents that may include wills, trusts, powers of attorney (both medical and financial) and living wills. A qualified estate-planning attorney can help them build the plan.

  2. Who is doing what? Whether they are naming an agent to make decisions, selecting an executor or naming a successor trustee to manage things, everyone should be on the same sheet of music as to roles and responsibilities. The result: efficiency and family harmony.

  3. What caused you to last look at your legal documents? Your parents may have laid out a robust plan when you asked them about it, but if they drafted the documents that bring that plan to life decades ago, it could be time for a refresh. Tax laws have changed dramatically and it could also make sense to re-establish their intent with respect to powers of attorney. A financial institution may be less likely to recognize a 25-year-old power of attorney than one drawn up a couple of years ago. In the same line of thinking, determine if all their beneficiary arrangements reflect their current wishes and are synchronized with the other means by which their assets will be distributed.

  4. What type of insurance do you have? The open nature of this question could cause you to chew up a lot of time. But do you really know what’s going on with your parents’ insurance coverage? I happen to know my mom has a long-term care policy, but only because I sold it to her! A firm grasp of your folks’ life, long-term care and health insurance policies is important knowledge. A survey of their insurance could identify gaps or unnecessary coverage and influence care or lifestyle decisions. It could be that policies purchased decades ago don’t make sense today or new ones should be considered.

  5. Who do we need to contact? If your parents already have a letter of instruction documenting their key contacts (attorneys, accountants, etc.), providers (banks, brokerages, insurance companies, etc.) and social media account details in a single document or notebook, that’s fantastic. If not, ask them to get it done. Are there special programs or services they’re eligible? Perhaps, they have or should go through the VA pre-need burial eligibility process or as USAA members you, the children, could take advantage of services offered through the Survivor Relations Team. Dig into the details.

  6. How should we handle things when you’re gone? This question provides a blank slate to dig into the details of their wishes. There’s a lot of ground to be covered, but details might include your parents’ desire on a wide range of topics including: preferred burial location, cremation, type of service, obituary details.


If the thought of diving into these questions doesn’t make you just a bit uncomfortable, you’re probably the exception. However, the easiest route to understanding is to let your parents do the talking. I hope these open-ended questions will help you make that a reality.


Have you had to have these difficult conversations with your parents?


About the Blogger: JJ Montanaro is a Certified Financial Planner® professional and part of the Military Affairs team at USAA. He’s a graduate of the U.S. Military Academy and has over 20 years of financial planning experience.


Disclosures: "Certified Financial Planner Board of Standards, Inc. owns the certification marks CFP® and CERTIFIED FINANCIAL PLANNER™ in the United States, which it awards to individuals who successfully complete the CFP Board’s initial and ongoing certification requirements."

The information contained is provided for informational purposes only and is not intended to substitute for obtaining professional financial advice. Please thoroughly research and seek professional advice before acting on any information you may have found in this article. This article in no way attempts to provide financial advice that relates to all personal circumstances.

No Department of Defense or government agency endorsement.

The trademarks, logos and names of other companies, products and services are the property of their respective owners.


257207 - 1118

Occasional Visitor

Excellent article. My mom is 65 years old; my siblings and I have discussed this lightly, but really just to the extent we all agree that no one knows anything... Not a great starting place. As-is we figure that whoever could get there to take care of her business would be the one who made the decisions. Who knows what would happen... After reading this article I'm going to make it a goal to talk with her on this matter over the holidays. Thank you so much!

Julie 2

My mom is 76 and we made an appointment at a funeral home last month because she was ahving questions about the cost of burial and didn't want it to be a burden on the family.    It is a good idea becasue now I know how she wants to be buried and we can now plan for that financially.

Community Manager
Community Manager

Dear @Kiba17, Thank you and good luck with your conversation!

Community Manager
Community Manager

Dear @Julie 2, Thank you for your comment. Glad to hear your family is making a plan!