Asking your parents about their wishes will ensure that you’ll know how to make the appropriate decisions when the time comes. Even though most people recognize the value of these discussions with their parents, actually initiating the conversation can feel uncomfortable. Will they think you’re invading their privacy, or worse, making a grab for their cash? It’s human nature to put off complicated or emotionally heavy tasks. And the loved ones you tried to protect by tiptoeing around these kinds of issues will be the ones who end up suffering the most. 

Although these conversations may be difficult, pushing through the challenge and engaging with your parents is one of the best things you can do for them and for you. In the end, it should reduce their anxiety and minimize potential friction between siblings. Remember, you aren’t trying to ask about your inheritance; you’re merely attempting to understand your parents’ wishes.

Don’t be surprised if your parents are reluctant to openly discuss these items. Some people are private by nature or fiercely independent. It’s also hard for some people to admit they might need help, especially from their own children. But it is possible to mitigate these issues by considering the items below. 

• Consider spreading the discussion over several get-togethers. If you feel that the discussion is productive and your parents are receptive, then you can consider addressing additional topics.

• Make your intentions absolutely clear or your parents may be reluctant and the conversation labored. Be sure to convey that you care about them and want what’s best for them. Assure them that you’re not trying to get your hands on their assets. 

• Think about times of the day when your parents are most productive. Some people are more mentally active in the morning and others in the evening.

• Determine the optimal logistics for the discussion. Meeting in person is usually the best option, but if that is not feasible, set up a video call. Being able to see your parents’ reactions during the discussion is important. 

• Carefully consider who should be a part of the discussion as well as who should lead it. In many families, one sibling assumes the primary caretaker role because he or she lives nearby or has a close relationship to their parents. These siblings may be the best to lead the discussion. Also take into consideration if a sibling has a contentious relationship with your parents or may cause them to resist being forthcoming. In some cases it may be best to bring in a trusted, independent party to help keep everyone focused and facilitate conversations about difficult subjects during the meeting.

• Be transparent with other family members. Try to include siblings in the conversation so it won’t seem as though you’re trying to be controlling or secretive. This will also help avoid family disputes and ensure everyone is on the same page. 

• Do you plan to stay in your current home for as long as possible? Are there things we need to do to your house so it’s safe and comfortable for you as you age? 
• Would you be willing to hire someone to help you at home if you can’t do it on your own anymore? 
• Are you willing to move into a smaller place that’s easier to manage? When? 
• Would you consider moving to an assisted-living facility? Can I help you scout out quality facilities now, so we know what’s available in case you need one in the future?
• Has either of you thought about whether you would want to stay in the house if you were alone? 
• Would you consider moving in with me or one of my siblings if we all agree that you need help with your personal care or aren’t safe at home alone anymore? 

• What doctors do you currently see? Are you happy with the care you’re getting? Will you consider giving your doctor permission to talk to us in case we have questions about your medical treatment?
• What medications are you currently taking? Are you able to manage various dosage instructions? Do you have any notable side effects? At what pharmacy do you get your prescriptions filled?
• What health insurance do you have? 
• How do you feel about being kept alive with ventilators, feeding tubes, or other interventions? And under what circumstances would you want that? 
• Do you have an advance medical directive (document expresses your parents’ wishes regarding life-support measures, if needed, and designates someone who will communicate with health-care professionals on their behalf)? Where do you keep them? Have you shared them with any family members, doctors, or clergy? 

• Do you have a will? How recently was the will written? Who will be the executor? Where is the original document? If the will is more than five years old, suggest they review it to make sure their current wishes are represented. 
• Do you have any have any specific personal property disposition requests that they want to discuss now?
• Who’s on your team? If your parents work with financial and legal professionals, ask for a list of their names, addresses and phone numbers (or make sure you know where to find that list if you need it).
• What financial accounts do you have — and where? Ask your parents to create a list of their bank, brokerage, and retirement accounts, including account numbers, name(s) on accounts, and online usernames and passwords, if any. If they’re uncomfortable doing this, have them put all the relevant info in a notebook, so you will have the essentials when you need them.
• Do you have a durable power of attorney (legal document that allows a named individual to manage all aspects of a parent’s financial life if the parent becomes disabled or incompetent)? Who is named individual?
• What insurance do you have and where are the policies?
• Where are your other important documents: Social Security cards, titles to their house and vehicles, outstanding loan documents, and past tax returns. 
• Do you have a safe-deposit box or home safe? Make sure you can access the key or combination.
• Are your beneficiary designations up to date? Beneficiary designations on your parents’ insurance policies, pensions, IRAs, and investment accounts will trump any instructions in their will.
• Do you have an overall estate plan? A trust? A living trust can be used to help manage an estate while your parents are still living.
• Are you willing to have a joint checking account with me so I can help you pay bills if necessary? 
• Do you need help paying monthly bills or reviewing items like credit card statements, medical receipts, or property tax bills? Do you use online bill pay for any accounts?

• What digital/social accounts do you have? Identify usernames and passwords, that might be required to shut down anything online. 
• See Optima’s "Guide to Protecting Your Digital Assets” 

• Do you want to be buried or cremated? Do you have a burial plot picked out?
• Do you have any specific requests or wishes for your memorial service?
• Are you an organ donor? Where do you keep your organ-donor designation; in some states, it’s on a driver’s license, in others there’s an organ donor card.

After each conversation, write down what was discussed. Share these notes with all parties to ensure that everyone is one the same page.