Skip to main content
How to Organize Your Life BlogOrganizing the Things in your Life

Difficult Conversations with Your Parents: Why They are Necessary & How to Have Them

By May 31, 2020October 4th, 202314 Comments

I don’t know about you, but I avoid difficult conversations like the plague. I would rather do almost anything other than have a difficult conversation. In fact, I have become talented at skirting around any topic that borders on introducing a difficult topic.

The fact is, though, that it’s necessary to have difficult conversations with your parents so that you know how best to support them and what their wishes are should a delicate situation arise.

I wrote a blog about a year ago after visiting with my son and his family in San Francisco. As a parent visiting my adult child and his family, I wanted to be helpful. There were certain things I could do and others that would be over-stepping boundaries. How did I know? We had a conversation.

Recently, the June issue of Real Simple magazine published an article which gives reasons to talk to your parents about their finances titled “How to Talk to Aging Parents about Future Finances”. This got me thinking about having these conversations with my children.

As the article indicates talking to your parents about their money and death are two topics most people avoid.

Money and Death

We avoid having these difficult conversations because they expose our vulnerabilities. My mother would never, ever have discussed her finances with me. If I brought the topic up, I am confident she would have given me a look, then told me it was none of my business, and walked away.

Now that I’m in that position, I know I will feel very uncomfortable and vulnerable when I have this difficult conversation with my children.

Talking about death is another difficult conversation. It serves to reinforce our own mortality. Of course, we all know that one day we will die. Why do we have to talk about it?

We must have these difficult conversations so that our loved ones will be informed and feel more in control. I will come back to this thought.


As parents, we think it’s our job to take care of ourselves and our family. Most of us do not think to share the details of our finances with our children. If we are in debt, we may not want to acknowledge that. Maybe we have ignored advice or invested badly, we may not want our children to know that either. Or, maybe just maybe we have done everything and have all our paperwork in order, and we think in good time we will share that information.

Here’s the thing. Our children need to know. As we get older and, maybe, less able to care for ourselves our roles reverse. It is our children who become the caretakers. They have a right to know if we have taken steps to protect ourselves financially.

The questions our children may want to ask are: Do you have a lot of debt? Who have you assigned to have financial power of attorney? Do you have long-term care insurance? Do you have a living will?

Something they probably will not ask is: What are your wishes should you pass away?  You may not know the answer to this question either. Think about it. The last thing you want your children to worry about is how best to honor your wishes when you do pass away. Do yourself and them a favor, write your wishes down. Give that information to your attorney to keep with your will.


Give your children peace of mind by providing them the answers to these questions. If you don’t have answers, let them work with you to figure them out. Both you and your children will feel more in control. They won’t worry as much because they will know what to do when the time comes.

How to have a difficult conversation

Now that we’ve established that it’s necessary to have these difficult conversations how exactly do you make this happen. As I said earlier, my mother would not have sat still for one. She would have silenced me with a look and walked out of the room.

Times have changed, we are living longer, and we share more with our children but still these are difficult conversations for anyone of any age.

Start by preparing

As parents, we can start from a place of understanding. Our children want to know we are safe and cared for. We can allow ourselves to be vulnerable and answer our children’s questions honestly.

As children, you can start by preparing your parents. Try not to dive into a sensitive topic. Perhaps begin by sending a text message saying something like: Mom/Dad there’s something I want to talk to you about this weekend. Do you have time? This may serve to alert your parents that you want to have a serious talk with them.

Organize your thoughts. Clear out the clutter. Come to this difficult conversation knowing the questions you want to ask. Have a plan. Do not expect to walk away in 30 minutes with your questions answered. Here is a great list of questions from Real Simple that will help guide your conversation.

Start small

These topics are HUGE and may require more than a couple of difficult conversations. You, as the children, may want to introduce the overall topic of preparing for the future needs of the parents. Then ask for the name and phone number of the attorney. Decide what is important for you to know now.

 As with any big project, I advise tackling one aspect at a time. No one wants to feel overwhelmed. Pick one small thing to address. When that is completed move on to the next.

Remember you are still our children. Have respectful, non-judgmental conversations. Your parents may not be aware of steps to take to protect their assets or pay down their bills. They will not want to feel as if they are giving up control of the way they life their life.

Avoid shut down

Parents may be tempted to shut down if they feel as if their children are making the decisions for them. Just as we gave you choices when you were children, you can provide your parents options and then let them decide what is best for them right now.

You never know what someone else is thinking unless you ask. Dare to have these difficult conversations with your parents while you can. They may have been worried about sharing this information with you but didn’t know where to start.

As a parent, I can honestly say, these are not conversations I am eager to have with my children, but I admit they are certainly necessary.

Be brave and initiate one or more of these difficult conversations with your parents. Reach out to me if you like some guidance organizing your plan for having these conversations.

Diane N. Quintana is a Certified Professional Organizer®, Certified Professional Organizer in Chronic Disorganization®, Master Trainer and owner of DNQ Solutions, LLC based in Atlanta, Georgia. Diane teaches busy people how to become organized and provides them with strategies and solutions for maintaining order in their lives. She specializes in residential and home-office organizing and in working with people affected by ADD, Hoarding, and chronic disorganization.


  • Yes, indeed this is a very difficult conversation to have. After the loss of a few friends and one recently to the Corona Virus, I’m compelled to put everything in order. The last thing I want is to leave unnecessary responsibilities for my children.

  • Julie Bestry says:

    You raise such excellent points. It’s funny the things we’re comfortable or awkward about discussing. My mother is very clear and comfortable discussing financial subjects with us; I’m comfortable discussing her finances, but not my own. I’m fine discussing my advanced healthcare directive with her and chatting about my own “final” plans, but she can’t bear the thought of me reaching a final life destination. I have no children, so I’ve been careful to put in place Powers of Attorney for my health and finances; it was easier to have this discussion *with myself* than coming to terms with the items in my advanced care directive.

    These are vital conversations. Whenever I work with a new residential client, no matter the area in which we’re going to work, I never leave the first session without asking: do you have a will? do you have a healthcare proxy? do you have a fire extinguisher? These three questions help get clients started in the direction of thinking about vital conversations. For some people, money is an awkward subject; for others, it’s death. But we all have to get better at having them.

  • I think you are correct when you say “times have changed”. Finances has become a lot more complicated for some people. The changing technology also makes it hard for older people to sometimes keep up. I know that I am assisting my mom with these types of things more and more these days.

  • Seana Turner says:

    This is a critical discussion to have. I think it helps if you can keep conversations short and casual… sort of like when talking with teens about sex:) Also, it can be possible to glean information on the sly. For instance, over dinner months ago with my parents, I asked, “What are your favorite hymns?” I took note, so I will remember when the time comes to plan a memorial service, but no one was the wiser. Of course, serious subjects require time an intentionality, so being open and trying to reach common ground is worth the effort.

  • Difficult conversations are just that- difficult. Like you, my tendency had been to shy away from them. At a point, it was clear that I could no longer do that. There were many family crises and occurrences that required delving, honesty, and discussions. A bunch of years ago, I went through Denslow’s Coach Approach foundation courses. Simultaneously, my father was dying. It was a tough time. The fascinating part is that during the coaching classes, Denslow and Cam gave me language and tools for having difficult conversations. The focus was to have those conversations with clients. However, the concepts translated into my personal life. Since then, I no longer shy away from these challenging conversations. They are still hard, but I now have the language that helps me have them.

    My mom has dementia and isn’t able to communicate like she once did. But before her cognitive abilities were compromised, we spent a lot of time together getting her affairs in order, making sure I understood her wishes and getting all of her paperwork updated. At the point she no longer could manage, I was able to seamlessly step in to help because she had everything in place (Power of Attorney, Advanced Health Directive, Living Will, etc.) and I knew what she wanted. It was one of the best gifts she could have given me, and I’ll always be grateful.

    We’ve had open conversations with our daughters so that they know where things stand. We still have more to do, but the idea is that they will be prepared when and if the time comes.

  • I totally agree! Communication is the key to knowing. I was the executrix of both my parents’ estates and I was so grateful that I spoke with them about their wishes before they passed. It helped me make decisions quickly and easily and was able to close both of their estates within the one-year time frame.

    I wrote a post several years ago about how to start this discussion with the parents. It’s a six-part series that goes in deep to help adult children figure out how to communicate in various areas like the discussion of downsizing, letting go of stuff, money matters, legal documents, paper management, and online presence. It’s one I am going to share again in these uncertain times. Thanks for the reminder and for sharing your thoughts.

  • Yeah….sigh…..these conversations ARE difficult, but SO, SO, important. Fortunately for me, my family is relatively open about these things. Even so, certain topics need to be revisited as time (and life) progresses. Plans need to be tweaked. Wills need to be updated. Minds need to be refreshed. Passwords need to be re-shared.

Skip to content