How to Approach Difficult Conversations with an Aging Loved One

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It’s important to have tough but necessary conversations about everything from living arrangements to final wishes early, face-to-face, and with backup from family or friends. Be empathetic and respectful. Stay positive instead of being critical, and reassure your loved one that you are their advocate. You’re on the same team, making decisions with them, not for them. 

In his book, How to Say It to Seniors, geriatric expert David Solie explains that because elderly people face so many losses at this stage of life, they tend to rigidly control the few things they can. Be patient. Ask open-ended questions instead of making judge-y sounding statements. Frame the conversation around what matters to them, not what’s the matter with them. Listen to how they feel, acknowledge their fears/concerns and talk about what might ease their mind, compromise, and come up with a plan together. Try to avoid drastic changes. Read on for tips on discussing six important topics with your aging loved one.

The Will Talk

A Last Will and Testament dictates the way that your assets will be distributed and utilized following your death. A Living Will states your wishes regarding life support in the event that you are in a persistent vegetative state or irreversible coma and cannot communicate your wishes.

When someone without a will or trust dies, their estate goes through probate, meaning a large percentage of its value goes to taxes and court fees. That’s why having a living will is important, even though it’s a big old bummer. Has your loved one made plans for when they’ve departed this planet? Have they signed a DNR? Do they want to be buried or cremated? Where do the ashes go? It’s okay to ask, no matter how macabre it may seem. 

Having these uncomfortable conversations early can eliminate having to make tough decisions in a difficult time. Consulting an attorney on estate planning can raise questions you may have never thought of. 

In addition to legal and estate planning, a planning tool like the Family Love Letter provides a place to store info such as contacts, assets, liabilities, insurance and benefits, documents, and more. Approach them in a way that focuses on you, not the fact they’ve spent more time here than they have left. Say, “I know you don’t want me to stress out about (issue). I just need some clarity on (issue).” It’s likely that you don’t have these papers in order—perhaps you and your loved one could fill out your living wills together. Making plans now can minimize conflict in the future.

Are They Safe To Drive?

The amount of drivers on the road who can only see out of one eye is probably pretty frightening. Physical and cognitive decline can make reacting, seeing, and therefore, driving difficult, if not dangerous. On average we’ll outlive our ability to drive by about 10 years. If you notice these warning signs, it might be time to shift from the driver’s side to the passenger’s seat. Unfortunately, no adult wants to give up their keys, but this could literally turn into a life or death situation. 

#1) Don’t bring it up in the car! With all of these difficult conversations, you want to select a good time and place and plan what you’re going to say. If possible, wait until they are rested, fed, and in a good mood. Ask open-ended questions to find out how they see the issue. Instead of forcibly taking away the keys, suggest a driving assessment from the DMV to get an outside opinion. Many areas offer “mature” driving courses through the DMV, AAA, AARP, and auto insurance companies both online and in person.

Separate mobility from the concept of independence by exploring other transportation options, including ridesharing services for seniors like Uber or Go-Go Grandparent (for those who don’t use smartphones), local senior transportation services, carpooling, or finding a neighbor or friend with wheels. This way, they can still do their shopping, get to doctor’s appointments, go to church, and stay social. 

The Driving Dilemma offers more resources for older drivers and their families. If all else fails, report them as an unsafe driver to the DMV. 

Long-term Care Plans

Many Americans will age beyond their ability to live independently. Talk to your loved one about their expectations and options should they become unable to take care of themselves. How do they plan on covering the expenses? Does your loved one have savings, Medicaid, Medicare, veterans benefits, or long-term care insurance? Here are some good ideas for paying for assisted living. Contact a financial planner or an elder law attorney if you need help figuring out how to fund long-term care.

Physical and Mental Health

Your aging loved one’s health is an ongoing conversation. Do you know who their doctors are? What medications they’re on? And for what medical conditions? Some people are reluctant to complain or may not realize they’re experiencing symptoms. Look out for physical changes, as well as shifts in their emotional and cognitive states. Are they having trouble with stairs? Did they almost set the kitchen on fire trying to fry chicken again? Are they showing signs of confusion? Significant shifts in their well-being need to be relayed to their physician in the timeliest of manners.

Address Financial Issues

Money can be a complex and taboo topic. Some people would rather arrange their own funeral than go through their finances. Talk to your loved one about who they want to manage their money and make decisions for them should they be unable due to stroke, dementia, etc. Here are 10 more financial questions to ask. Have they set up a power of attorney? Without a POA in place, the courts will have to grant guardianship in order for someone to access accounts on their behalf. Would it be a good idea to put the house in your name? offers great strategies for managing your parents’ finances.


Due to nostalgia, or reluctance to pack up a lifetime of possessions, your loved one may not want to move. But what if their living situation becomes too much to handle? Perhaps it’s too difficult or expensive to maintain, or the layout just doesn’t make sense anymore due to physical limitations. Look for visible and tangible clues that might help open a convo about future living arrangements, particularly downsizing to a residence that’s much more manageable. Stay positive. Instead of dwelling on the loss of a dwelling, focus on the good aspects: less responsibility, easier maintenance, and more moolah!