The once-a-year insurance and benefits review: what to gather, and who to ask

Put it in the calendar once, in early October

Pick a fixed date each year. The first Saturday in October works well for most families, and here is why.

Medicare's annual enrollment period runs from October 15 to December 7, with changes taking effect on January 1. The plan documents for the coming year arrive in the mail in late September, in an envelope most people put on a pile. Doing the review in the first half of October means you are reading, comparing and asking questions before the window opens, rather than making a decision on December 6 because the deadline is tomorrow.

Block three hours. Put it in a shared calendar so a sibling can join or take a turn. Do it at a kitchen table with the actual folder, not on a phone in a parking lot.

Set the repeating reminder now, while you are thinking about it, and set a second reminder for late September that says only: open the mail from the insurers.

One date, once a year, is the entire discipline. Everything else on this page is just what you do when the date arrives.

The folder: gather this before you start

Half of the work is retrieval, and it is much less painful in one sitting than in eight interruptions.

Collect both sides of every card: Medicare, any Advantage or supplement plan, the drug plan, dental, vision, and any employer or retiree coverage. The Annual Notice of Change letter for the coming year. Last year's premium statements. The most recent Explanation of Benefits notices. The current pharmacy details. Any long-term care policy. Homeowner or renters and auto policies. Life insurance policies, and any burial or pre-need funeral contract. The agent or broker's name and number for each.

Photograph both sides of every card and put the photographs in the binder and in your email.

Then build a single index page with one line per policy: type, company, policy number, premium, renewal or review date, phone number, and the agent's name.

That index page is the review. Everything else in the folder is backing paper. If the house floods, the index page is the document you would actually want.

• Both sides of every card, photographed
• The Annual Notice of Change letter
• Premium statements and recent Explanation of Benefits notices
• Long-term care, life, burial, home, auto policies
• Agent or broker name and number for each
• One index page: type, company, number, premium, date, phone

The Medicare calendar, and who explains it for free

The dates are set nationally and they do not move around by state.

October 15 to December 7 is the annual enrollment period, with changes effective January 1. January 1 to March 31 is the Medicare Advantage open enrollment period, for someone already in an Advantage plan. Separate special enrollment periods exist for particular circumstances, including a move to a new area. Confirm the current dates each year at medicare.gov rather than trusting a page from last year.

The part most families do not know: every state has a State Health Insurance Assistance Program, which gives free, unbiased, one-to-one counseling. Nobody is selling anything. Find yours through shiphelp.org or the Eldercare Locator at 1-800-677-1116.

Book the appointment, and bring the index page, the medication list and the Annual Notice of Change.

What to ask them: whether the plan still covers the pharmacy your parent uses, whether their doctors are still in network for next year, what the costs are changing to, whether the medications on the list are still on the plan's formulary, and whether any other enrollment window applies to your parent's situation.

• Oct 15 to Dec 7: annual enrollment, effective January 1
• Jan 1 to Mar 31: Medicare Advantage open enrollment
• Confirm dates at medicare.gov each year
• Free counseling: shiphelp.org, or 1-800-677-1116
• Bring the index page, the medication list and the notice letter

The policies people forget

Health coverage gets attention. These are the ones that quietly go wrong.

Long-term care. Ask the insurer what triggers a claim, what documentation they require, and how long they take. Write the answer down; the moment you need it, you will not want to be finding out.

Life insurance and burial policies. Check the premiums are still being paid and from which account. A lapsed policy is one of the more common and least necessary losses in this whole area.

Home, renters and auto. Address changes, and what happens if the house is standing empty. That is a call to the insurer, not a question to answer yourself.

Dental and vision, which often sit with a different company entirely and renew on their own cycle.

Add-ons that bill monthly: credit card protection plans, utility line cover, appliance warranties, alarm monitoring. Check the bank statement for anything recurring nobody can explain.

Veterans' benefits. A VA-accredited representative can tell you free of charge what may apply. Ask them; do not work it out from a forum.

For every policy, three questions: is the premium being paid, from which account, and is the address current?

The question goes to the right desk

Most of the frustration in this job comes from asking the right question at the wrong desk. Write the question down, then write the initials of who owns it.

SHIP counselor: plan comparisons, enrollment windows, assistance programs, and whether your parent might qualify for anything they are not getting.

The plan's member services number on the back of the card: coverage questions, network status, prior authorization, and the appeals process.

Area Agency on Aging, via the Eldercare Locator at 1-800-677-1116: what local programs exist in the county.

Social Security, at 1-800-772-1213: the Part B premium, address changes, benefit statements.

The agent or broker named on the policy: home, auto and life questions.

An elder law attorney: anything about authority, who may act for your parent, or estate paperwork.

An accountant or tax preparer: anything about tax.

When you call, write the answer on the same line as the question, with the date, the name of the person and any reference number. That single habit is worth more than everything else on this page.

• SHIP counselor: Medicare plans, windows, assistance programs
• Member services: coverage, network, authorization, appeals
• Area Agency on Aging: local programs
• Social Security: premiums, address, benefit statements
• Agent or broker: home, auto, life
• Elder law attorney: authority and estate paperwork
• Accountant: anything about tax

What to file, and what to throw away

The insurance tab in the binder holds five things, in this order.

The index page at the front. Then this year's Annual Notice of Change. Then the current policy documents. Then twelve months of statements. Then the call log, which is simply the running page of questions, answers, dates and names.

Superseded plan documents from previous years can go, but keep the policy documents themselves and anything that establishes a policy exists. When in doubt, keep the paper and ask the insurer whether it still matters.

Write the review date and your initials at the top of the index page, so the next person knows how current it is. Then email a copy of the index page to yourself and to one sibling. If the binder is ever lost, that page is the thing you would actually need to rebuild everything else.

Before you close the folder, put next year's date in the calendar. The review is only useful as a habit; a single excellent afternoon three years ago is worth very little.

Questions