The Questions You’ll Wish You Had Asked Your Parents
You do not have to ask everything at once. The goal is not to finish a checklist — it is to make sure no one is left guessing. Tracy walks through the conversations worth starting now, before a crisis makes them urgent.
5 takeaways from the conversation.
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01
If something happened tomorrow, you need to know the basics. Who is their advisor, accountant, and attorney? Where are the accounts, insurance policies, and estate documents? Do you have access to their digital accounts? The first crisis hour is not the time to be searching for passwords.
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02
Confirm who is legally allowed to step in. Is there a durable financial power of attorney? A healthcare proxy and living will? Is the will current and are beneficiary designations up to date? Without these documents, the state decides for you.
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03
Ask what they would actually want if their health changed. Would they want to live somewhere other than home? What medical treatment would or would not they accept? What matters most: independence, comfort, or being near family? Preferences you never ask about become preferences you have to guess at.
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04
Uncover the obligations you do not know about. Old pension, forgotten annuity, a life insurance policy. Debts, loans, personal guarantees. Financial promises made to specific family members that could surface later. Better to know than to be surprised at the reading of the will.
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05
Ask about what is not on the financial statement. Who should receive specific heirlooms? What are their funeral or memorial wishes? What should happen to their digital accounts and photos? These are the things families fight over, and they are the easiest to prevent.
The printable conversation guide
15 questions across 5 categories. Print it, share it with your family, and start with one.