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How to Have Difficult Conversations With Aging Parents

A daughter having a difficult conversation with her aging parent

It’s never easy to have difficult conversations with aging parents, particularly around finances, health, and living arrangements. But those can be some of the most important conversations you ever have. As parents age, children often find themselves thrust into decision-making situations. And unfortunately, many don’t know their parent’s wishes or financial position.   

Iris Waichler, licensed social worker and expert in eldercare, says it’s important to have these conversations sooner rather than later. One of the biggest mistakes you can make is avoiding these discussions when loved ones are in good health. The sooner you talk, the better prepared you’ll be for inevitable changes in health, finances, or living arrangements.   

The following tips from experts can help you have difficult and constructive conversations with aging parents.

Tip #1: Make a List of Discussion Topics  

Before you approach your parents, have a clear sense of what you want to talk about. “Start by making a list of things you want to know and want to discuss with your parents,” says licensed cognitive behavioral therapist Amanda Levinson of the Neurofeedback and Counseling Centers of Pennsylvania.   

Don’t know what topics to cover? Suzanne Asaff Blankenship, author of “How to Take Care of Old People Without Losing Your Marbles” suggests that you break down the conversations into specific topics to discuss.  


If you might need to handle your parent’s finances, even for a brief period, such as when they might be recovering from a medical procedure, you will need to know where they bank, how to access their accounts, and more.   

Blankenship adds that you might also need to know things like:  

  • What are your parents’ assets and liabilities?   
  • What budget do they have if care is required or if they decide to move to a retirement community?  
  • Do they have a financial power of attorney?      

Living Arrangements  

As your parents become older, you may want to discuss whether they wish to continue living at home. And if they do decide to age in place, how will they manage if health issues arise? Questions regarding a living situation will evolve depending on health, marital status, and ability to be independent.   

Asking these key questions may help in deciding how they want to move forward:  

  • Do your parents want to age in place?  
  • Do they want to move closer to family?   
  • Do they want to live in a retirement community?    

Health Care   

Conversations regarding a parent’s health may be one that both parties may want to avoid. Still, it’s better to broach this subject when an older adult can still move physically and is of sound mind. Asking tough questions in the middle of a chronic or terminal illness is something you want to avoid.   

Some key points to address:  

  • Who do they want to care for them?   
  • Will a specific family member, friend, aide or agency look after them in case of illness?  
  • What are their wishes if they are terminally ill?   

End of Life Wishes   

Waiting until a parent is ill to evaluate assets, and end-of-life issues is not optimal.   

If you choose to have these end-of-life conversations ahead of time, here are some subjects to cover:  

  • Do they have a will? Where is it located?   
  • Do they have a medical power of attorney?   
  • Do they have an advanced directive?   


Some of the most difficult conversations may revolve around personal items and how a loved one wants to be remembered. Having conversations about legacy can be both rewarding and avoid family conflict down the road.  

Some conversation starters may include:   

  • What do they want to pass on to their loved ones?   
  • How do they want to be remembered?   
  • What can you do to honor their wishes?   

Do your homework ahead of time, adds estate planning attorney Lauren Blair. “Make certain you have consulted with attorneys and health care providers to understand the end-of-life processes and the needs of your particular parents.” If your parents have additional questions, be ready to answer with responses, it will allow them to connect with the right professionals to provide the advice and resources they need.  

Tip #2: Make it a Collaboration, Not a Confrontation  

Talking about these subjects may create tension because you and your parents may have different opinions about what’s best for them. As a parent ages, it can be difficult for them to ask for help or admit that they may in the future need support. Children need to listen to their wishes and concerns without interrupting or giving a knee-jerk reaction, even if they disagree.  

“Stay open-minded, be a good listener, and put yourself in their shoes regarding differences in decisions,” adds Levinson.  

Start With an Open Heart

Waichler advocates for opening the conversation with compassion. “Come from a place of love,”she says. “Tell them you care about them and want to do everything you can to help them live their life as long as possible with as much quality as possible.” Most importantly, tell them that you want to hear their thoughts instead of dictating what you want them to do.    

Keep it Light

Blair suggests that families look for ways to bring up sensitive topics more casually, so parents don’t feel judged or overwhelmed.   

“Don’t make dinner plans at a restaurant or summon your parents for a serious talk about needing a will and signing a DNR (do not resuscitate form). Look for opportunities to start the subject. Find a casual conversation and setting. Your listener will be more receptive to engaging in conversations if they don’t feel set up,” says Blair.   

You’re Together in This

When arguments occur, remind your parents and other family members that all of you are on the same team. You all are working toward your aging parents’ health, safety, and happiness.  

To emphasize this point, Blankenship says, “Use the word ‘we’ often. Don’t assume you know the elder’s opinion — Ask them what they think. Listen and admit if you misunderstood or didn’t clarify their opinion, wishes, or preferences.”   

“Go into the conversation from a place concern, not a place of control. These conversations are never easy for families because it means talking about end-of-life logistics, but getting it done will make the last years of your parents’ life the most comfortable they can be,” adds Levinson.   

Tip #3: Include Others in the Conversation  

With these challenging topics, involving other individuals that your aging parent respects may be helpful.    

Some potential people may include a doctor, a lawyer, a clergy member, an accountant, a longtime colleague, or a friend. “It lessens the potential of conflict with the adult child or family member being the one who made the decision,” says Blankenship.   

Waichler says it is also a good idea to include family members who may eventually be called upon to care for or manage specific issues. Think of it as building an all-star team for your parent. For example, one family member may have a medical background while another understands insurance issues. Another family member may be able to offer physical assistance or help get the appropriate care support.  

Tip #4: Recognize It Is a Process   

Many of these topics are complicated and will naturally cause uncomfortable feelings. Additionally, your parents may not be ready to discuss certain subjects. What’s important is that the conversation has started.  

“Recognize that this is a process and not a one-time conversation. If they are reluctant to discuss it at first, just let them know that you would be available to have the conversation in a month or whatever time frame makes sense,” says Waichler.   

Most importantly, Waichler adds, “Don’t push it if they don’t want to engage. You have opened the door to have the conversation at a later date.”  

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