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As National Estate Planning Awareness Week was ending, a friend reached out about her aging parents. During a recent visit, she realized they had some real physical challenges, and she worried that their affairs were not in order. “Do you have a checklist to help us start the process?” Here goes it!

Yes, you will be prying, and your parents may resist. Bring your empathy, because these conversations can stir up feelings about control, privacy, dignity, shame, fear and lack of confidence. An icebreaker helps: “I read an article about having hard conversations, and it made me think we should talk about your physical and financial security and what you would like to happen in the future.”

As any loyal viewer of “Law & Order” knows, discovery is the exchange of information before a trial. For our purposes, it’s when you assemble the documents needed to keep your parents safe and secure. Store everything in a central location so siblings can review and update it.

Health/insurance

— Medications, including vitamins and supplements.

— Medicare information, including plan types and supplemental coverage. If your parents agree, you and/or your siblings should get authorization to talk to Medicare directly. (Medicare Advantage and Part D plans are private insurers with their own authorization forms.)

— Doctors and their contact information. If your parents use health portals, ask permission to log on so you can see visit results.

Financial information/documents

Get contact information for any financial advisor or insurance agent. If your parents are comfortable, ask for duplicate statements or online access to monitor their accounts.

— Bank, investment and retirement accounts

— Automatic payments and payees

— Insurance policies (life, long-term care, disability)

— Housing, land and cemetery deeds

— Mortgage and loan accounts

— Vehicle titles

— Partnership and corporate operating agreements

— Marriage licenses, divorce papers and military discharge forms

— Existing estate documents and the attorney who prepared them

I’m old school and believe it’s worth hiring one, especially if there are complications like a second marriage, family estrangement, a special-needs family member, a small-business partnership or significant assets. That said, if your parents’ situation is straightforward, an online service is better than nothing.

With your discovery documents in hand, you or the attorney should ask:

— Are you worried about money?

— What would happen if you needed assistance at home?

— Do you want specific assets, including sentimental possessions, to go to specific people?

— Are you worried that heirs would squander their inheritance?

— Do you want to be charitable?

— Will: Directs assets to beneficiaries according to your wishes and names an executor to oversee distribution. Without a will, state law determines who gets what, and the probate court will take its time divvying up the estate according to a preset formula.

— Health care proxy: Names someone to make health care decisions if you can’t.

— Power of attorney: Names an agent to act on your behalf, like withdrawing money, responding to a tax inquiry or making a trade.

— Letter of instruction: Covers funeral wishes and disposition of remains, which matters if your choices break with family tradition.

— Trusts: Revocable (changeable) or irrevocable (not changeable). Trust assets avoid probate and allow more precise transfers, but a trust can also add complexity and cost.

— Transfer-on-death accounts: Many institutions let you name a beneficiary on non-retirement bank and investment accounts, which generally avoids probate.

The executor needs copies of the documents, which include names, addresses and Social Security numbers of everyone named in them, and contact information for the estate attorney and CPA who will help navigate the process.

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(Jill Schlesinger, CFP, is a CBS News business analyst. A former options trader and CIO of an investment advisory firm, she welcomes comments and questions at askjill@jillonmoney.com. Check her website at www.jillonmoney.com)

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