Question: 

Sometimes I wonder if I know what my father wants. He has historically been very closed off to conversations regarding his health, future, and finances. Since Dad is now approaching 90, I think that we as children need to become more involved. What is the best way to figure out what he wants? How do I start that conversation?
 

Answer:

You are very blessed to have an independent parent of that age. The fact that he is managing so well is wonderful. However, I do see your concern for the future, as most of us to get to the point in our lives where we need some assistance.

For someone completely independent, I would start by discussing an area of expertise in which you shine, an area your father has indicated he respects your knowledge of. This is an effective way to lead-in to conversations about your father's future.

Perhaps you are good at investing, and your father has told you he admires your work. Privately share some of your strategies with your father, and ask him about his. Do this when you two are alone together, never in a group. He is going to be most comfortable sharing his finances with a child who has demonstrated wisdom when managing his or her own. If your relationship is distant or strained, any talk of money will not go well. Also, if you have not been responsible with money, do not expect your father to feel comfortable talking to you about his estate. Find your unique area of expertise that can lead to conversations about your father's future. Once you develop this dialogue, it will be easier for him to trust your decisions and open up about his finances and the future. 

Now let's talk about care needs and planning for healthcare decisions. In most families, the elderly gravitate to sons and daughters who work in healthcare or who demonstrate the most knowledge of the subject. It is unlikely that you will have an expert in every category in your family unless it is very large and diverse, but that is okay.

You will more deeply connect with your father about his future if you make the effort to get to know him better. Learn what you can about your father’s life. Express true interest in hearing about it. Ask him to tell you about his military career, or his teen years, maybe his first car. Then wait for an opening to bring up the things on your mind.

At this point, I am sure you get the drift. Your father will talk to you and share with you if you show real interest. Trust is a two-way street. It will make life richer for you both, materially impacting your relationship going forward. The contact will also give you the opportunity to plan together.

I wish you the best.