Thought Leadership

How to Have Hard Conversations with Aging Parents About Money

People say there are three topics you don’t talk about: politics, religion, and money. Now, we won’t speak to the first two, but we can confidently say that talking about money is one of the most important things you can do, especially when it comes to your aging parents. We know these conversations are difficult and most people will do just about anything to avoid them, but tackling the topic in a forthright manner is vital. 

Why do we avoid these conversations? 

When you know you need to have a conversation with your parents, you will often find creative ways to avoid the topic. So, why do we avoid the discussion so much? Here are just a few of the main reasons. 

Facing Reality. Conversations with aging parents about money are hard because it forces everyone in the room to face the reality of parents aging and their ultimate demise. Engaging in these conversations brings to light the reality that aging can be difficult and that unknown health and life stage challenges may lie ahead. 

Role Reversal. It feels odd to have a conversation with your aging parents where you are discussing taking care of the people who have cared for you your entire life. If you’re the one initiating these conversations, it can feel even more awkward. 

Confusion. Let’s face it: retirement, finances, and estate planning are confusing! There are so many different options and levels of complexity to consider with each topic, it can feel overwhelming to know where to start. 

But you can’t bury your head in the sand and ignore the circumstances. The worst outcome is to have an unwanted situation materialize in the future  that could have been better planned for and managed through proactive and forthright conversations today.

So, what questions should you be asking your aging parents and what issues should you have on your radar? Consider these three categories to discuss:

Estate Plan

As their child, you should know the basics of what your parents have put in place for their estate plan. Do they have a will mapped out? What about a trust? If so, who is the trustee and successor trustee, who has medical power of attorney, and are there any specific instructions? Knowing who to turn to should something happen or knowing if plans are put in place will make hard situations much easier to manage. 


What happens if health fails? Ask your parents about their medical directives, and if they have been explicit about any specific requests. Make sure you know who is the main medical power of attorney, and who has been designated as a backup. Discuss what level of care they want if health deteriorates and identify decisions that need to be made in advance of failing health.


What assets are in place? How are they owned and where are they located? Do they have enough money to support their future needs? Will you be needed to provide financial support? Most children have questions about how their parents are set up financially, but few know the details. 

How to Make Hard Conversations Easier

Each of these three topics are not easy to cover with aging parents, and we know that the financial side is often the most difficult of all. So, how can you make these conversations easier for everyone involved? 

We’d like to offer up a few simple tips:

  1. Set a distinct time for a conversation. Ask your parents if there is a time you can plan to talk about their retirement situation, estate planning and health care wishes. Leave the kids with a babysitter. Find a comfortable and private location. Eliminate as many distractions as possible. 
  2. Ask regularly. It doesn’t have to be a long, drawn-out conversation, but have a regular check-in to ask your parents if anything has changed from year to year. Tune into changes occurring in their health and their ability to process and make decisions.
  3. Be patient. Although you want to prepare for how you can support your parents wishes, and directives, understand they may not be ready to dive into all the specifics. Coming to terms with their health and mortality may be a hard topic for them to process. Understand that this will take time and requires a caring approach each step of the way.

At Planning Alternatives, we are here to help. We regularly hold family meetings where we bring parents and their children together to discuss important matters. We act as a facilitator to help guide the conversation. Relying on the guidance of a third party actually helps ease some of the stress and emotion, allowing family members to approach the topics in a more matter-of-fact manner. We also help explain some of the background behind how finances are structured, answer questions regarding healthcare and estate issues, and make sure the conversation is of a comprehensive and productive nature. We prepare clients with the pre-work needed to ensure the meeting is as effective as possible, and offer ourselves as a resource to any family member after the meeting occurs. 

As fiduciaries, we are here to support you first and foremost and provide guidance that’s in your best interest. We are here to look out for your wellbeing and help your family gain clarity around your wishes. That’s why these family conversations are so helpful. We’re here to do what’s right for you and your loved ones. 

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