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Tough Talks: Tips on How to Start Talking to Aging Loved Ones About Their Wishes

Tough Talks: Sharing is Caring - Tips on How to Start Talking to Aging Loved Ones About Their Wishes by Fern Pessin


Having served as a caregiver for eight years—supporting my father with Alzheimer’s Disease and my mother, who developed pseudo-dementia from the stress of caring for her life partner of sixty years—I’ve learned a lot about the power of communication. Now, I’m on a mission to help others navigate the often complex and stressful world of caregiving. 

This article will dive into key strategies to help caregivers reduce stress and foster cooperative relationships through effective communication before your loved one is in a position of dependency. By having conversations early, and tactfully, you can avoid confrontation and help make sure your loved one's wishes are carried out.   

Clear and Early Communication

No one wakes up and says, “I’m going to have a stroke today; let me get my affairs in order.” Unexpected events like car accidents, falls, illnesses, or weather disasters can happen anytime. Suddenly, the things you always thought you would someday discuss, share, and handle as the need arises become urgent, and loved ones are scrambling to find answers.

None of us know when we will become unable to communicate. Everyone should create a plan, make arrangements, and declare their wishes to their family as early as possible. As the person most likely to be asked questions about caring for your loved one in an emergency, you will want to have the answers ready so gathering this from your loved one is necessary.

I’ve seen two fortyish friends lose their ability to speak—one due to COVID-19 and the other to a stroke—leading to the loss of their small businesses because their families had no information or access.

I’ve witnessed single people get terminally sick and lose communication skills without having shared their wishes about resuscitation, what to do if they’re unable to think for themselves, or whether they prefer to be in a hospital or at home if they are unwell or near the end of life. Friends stepped up to help but had to make decisions based on what they would want for themselves, assuming it was what their friend would wish too.

Knowing what you want is not enough. Letting others who will care for you know what you want will ensure your wishes are followed.

If you have no one local to care for you, you’ll want your plans written and placed somewhere so those tasked with caring for you know what you wish.

If you think your parents have taken care of everything and you won’t need to know anything in advance, let me just tell you, you’re wrong. You need to understand where everything is so you can comply with their wishes and avoid feeling guilty about decisions that may not align with what they would have wanted. Do you want to pay for a funeral only to find out they had a cremation already paid for?  Do you know if they have veterans’ benefits or a pension? What about bonds or certificates coming due? Is there a safe deposit box? Investments in a business made years ago might yield unexpected benefits that can pay for care.

It’s imperative to start planning now. Major life decisions such as moving, hiring help, stopping driving, or determining care wishes in case of a debilitating illness should not be made on the spur of the moment. It takes time to gather your thoughts, discuss them with loved ones, make revisions, and feel confident that you have prepared for most situations that might arise. This ensures your loved ones have the information they need to honor your wishes, and you have the wishes of your loved ones to honor them. Once everyone in the family has reached adulthood, optimally, spouses, siblings, children, and parents should all share their plans with each other.

Conversation Starters

How do you start these tough conversations?

  • You can use indirect triggers to initiate meaningful discussions, making them seem part of a regular phone call or dinner conversation. Creating a stressful “We need to talk” moment is unnecessary.
  • Subtly incorporating hints into everyday interactions, you can encourage information sharing organically, helping others feel less confronted or pressured. 
  • Articles or media stories
  • Social media memes shared in your network
  • Experiences of neighbors or friends
  • "My financial advisor was talking to me about my plans for..."


Keep the Conversation on the Right Track

Once you get the conversation going, here are some techniques to make the conversation less confrontational. Begin by explaining that your primary goal is to honor their wishes. Your "need-to-know" is not about satisfying your curiosity but ensuring you respect their preferences. If you are unaware of their desires, you might make decisions that go against their wishes, and you really don’t want to do that.


Inclusion and Input: Engage stakeholders like siblings, parents, and professionals for comprehensive input and planning.

Use “I Feel” Statements:   Using “I feel” statements instead of “You should” can make discussions more empathetic. “I would like you to consider [moving, stop driving, hiring help] because I feel [worried that you’ll get hurt and no one will know, you’ll get into an accident and hurt someone or yourself, you’ll take the wrong medicine/set the house on fire without someone to help you].

Where To Go Next

Once you've engaged your loved one in a conversation about their wishes, the next step is often to take that positive momentum and get their information organized for access when you will need it and to build a team to help them, and you, carry out a plan.   For more on this read our related articles: Tough Talks: Getting Organized and Tough Talks: Building a Support Team

Additional Resources: 

Try downloading a question-and-answer booklet that will guide you through the info and data to collect and questions to ask at the non-profit, www.fivewishes.org.
I’ll Be Right There: A Guidebook for Adults Caring for their Aging Parents includes worksheets, checklists, and guidance for various situations. This book is available through FortyW Advisors or on Amazon in Kindle or print versions at https://bit.ly/PessinBooks.