Start Talking!

20 Questions to Ask when Mom or Dad Retires

written by Ellen Freudenheim, MPH

So your parents are retiring! What’s that got to do with you? Plenty, it turns out. Retirement is a change in life status that can affect the whole family.

What’s at stake? Oh, not much—just money, health and relationships. Not to mention the family heirlooms.

Here are 20 questions to ask your parents, whether they are about to retire, or currently retired. But take it slowly! You don’t need to ask every question the morning after the big retirement party!


1. Do your mom and dad each have an up-to-date will — and do you know where is it kept?

2. Do they each have a health care proxy, living will, health care power of attorney and other essential legal documents?

3. Do they have a system for keeping track of complex Medicare reimbursement forms, doctors’ bills and other health expenses?

4. Do you have lists of their important contacts, such as doctors, lawyer, and neighbors?

Getting a Life

1. What are mom and dad planning to do with the extra 40 or 60 hours a week they’ll have free in retirement? Do they have a vision of their new life?

2. If you are concerned that your parents will be isolated in retirement, where can they meet nice people or how can they strengthen existing social ties?

3. What are your parents doing to stay physically active?

4. If your dad is retiring while mom keeps working, then how will their household roles change—as in, who does the housework, cooking, shopping and bookkeeping?


1. Americans are living longer. Mom and dad might well make it past the ripe old age of 80 or 90. Do they have a financial plan for retirement– and does it cover the possibility of a long life?

2. Do your parents know how much money they have and where it is invested? (They don’t have to share this with you, but do they know?)

3. Have they worked out –in real numbers—what their expenses are likely to be in retirement?

4. Do your parents need financial planning help?

5. Do they have adequate long-term care insurance?

6. Do they need to work in retirement? There’s nothing wrong with that, but if so, what kind of work would be suitable? Might they retrain?

7. Do they know how to use a computer to keep track of their finances? If not, do they have a coherent system for keeping financial information up to date?

8. Have you talked about whether they plan to leave money or assets to you or your children upon their death, or whether they expect to spend their estate?


1. Some people move far away in retirement. How does this work for both your mom and dad—and for the rest of the family, too?

2. If they move, how does that impact your relationship?

3. Do your parents need help sorting through their possessions, and downsizing? Are there things you would like to ask them for, as in heirlooms or memorabilia? Can you say no if they want to dump too much on you?

4. Will the place your parents plan to move meet their needs in 5 or 10 years?

Retirement is a gift of time to enjoy. When your parents retire, their decisions may well affect you, too. So: Start talking!