Questions to Ask Before Hiring a Medicare Advisor or Brokerand the Answers to Listen For

1. "Are you an insurance agent, a SHIP counselor, or a fee-only advisor?"

Why it matters: each kind is regulated differently and paid differently; the label determines every answer that follows.

A good answer is instant and unhedged, whichever kind it is.

Jason's answer: Fee-only Medicare advisor — Florida Unaffiliated Insurance Agent, license W149493: an independent consultant paid "a fee established in advance by written contract," barred from affiliation with any insurer, insurer-appointed agent, or agency (Florida Statutes 626.015(20)). Also licensed in Arizona, North Carolina, Ohio, Tennessee, Texas, and Washington — the full list, with license numbers, is on the Licenses by State page.

2. "Are you licensed in my state, and can I have your license number?"

Why it matters: agents selling Medicare Advantage or Medicare drug plans must be licensed by their state, complete annual training, and pass yearly testing with a score of 85% or better (federal rule 42 CFR 422.2274). You can verify any agent's license through your state insurance department, or nationally at nipr.com. A professional who hesitates to hand over a license number is answering a different question.

A good answer includes the number without being asked twice.

Jason's answer: In Florida: W149493 — verifiable in about a minute at the Florida Department of Financial Services licensee search, licenseesearch.fldfs.com. Every other state license is listed on the Licenses by State page, each verifiable through that state's insurance department or nipr.com.

3. "Are you captive, independent, or not selling at all?"

Why it matters: in industry terms, a captive agent represents one insurance company; an independent broker represents several — but only the ones they hold contracts with. Both can only enroll you in what they sell.

A good answer is the label, plus how many carriers that means.

Jason's answer: Not selling at all. No carrier contracts exist to limit the menu — and the analysis can end in "keep exactly what you have."

4. "How are you paid — commissions, renewals, bonuses, or fees? By whom?"

Will I pay you directly, or are you paid by the insurance company? This is the load-bearing question, and the numbers are public. For Medicare Advantage and drug plans, CMS caps what insurance companies may pay:

CMS Contract Year 2026 agent and broker compensation memo (June 18, 2025). A few high-cost states run higher — California and New Jersey top out at $864 first-year. CMS has already published 2027 rates: $725 and $130 first-year. Renewal commissions continue each year the client stays on the plan.

Why it matters, continued: Medigap commissions are different — a percentage of the premium set by carrier contracts under state rules. In Florida, the first-year commission may not exceed 200% of the second-year commission, and renewals stay level for at least five renewal years (Rule 69O-156.013, Florida Administrative Code, adopting the national model). None of this is a scandal. It is the incentive structure sitting underneath "free" help.

A good answer is a number, not a speech — a commission broker passes this question by disclosing: "I'm paid commissions by the carriers — up to $694 first-year for a Medicare Advantage plan, about half that in renewal years — and here it is in writing."

Jason's answer: Flat fees paid by clients, only: $250, $500, or $1,000 by package, listed publicly on the pricing page before any conversation. Zero from insurance companies — a license condition, not a promise: Florida law forbids an unaffiliated insurance agent from receiving "compensation or any other thing of value" from an insurer (Florida Statutes 626.311(6)).

5. "Does your pay change depending on which plan I choose?"

Why it matters: even with CMS's caps, incentives can differ across products — and the honest response to this question depends on which pay model is answering.

A good answer depends on who's answering. From a commission-paid agent, the honest answer names the differences — a Medigap sale pays differently from a Medicare Advantage enrollment, and the renewal streams differ. From a fee-only advisor, "no" is the structural truth: the fee cannot change with the plan.

Jason's answer: No. The fee is identical whatever the recommendation turns out to be — including "keep what you have" or "use the free SHIP counselor."

6. "Will you put in writing which companies you represent and how you're paid?"

Why it matters: an honest arrangement survives being written down. Brokers who don't offer every plan in your area are already required by federal rule to tell you, in exactly these words: "We do not offer every plan available in your area. Currently we represent [number] organizations which offer [number] products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options." (42 CFR 422.2267(e)(41), as amended April 2026.) The rule requires only the counts — the carrier names are yours to ask for.

A good answer is the filled-in counts and the carrier names, on paper.

Jason's answer: Already in writing, here and across the site: no companies represented, no plans sold, fees public, nothing accepted from carriers.

7. "How many companies and plans can you actually offer me here?"

Why it matters: brokers can only enroll you in contracted plans, and the required disclaimer gives you counts, not names. The plans not on their list stay invisible unless you go look.

A good answer is a straight count, plus an offer to help you check the rest.

Jason's answer: Contracted with no one, so nothing is off the menu — the comparison starts from the Medicare Advantage and drug plans Medicare's own tool lists for your ZIP code, plus Medigap options, which that tool doesn't cover.

8. "Will you compare Original Medicare plus Medigap against Medicare Advantage — both paths?"

Why it matters: it's the one decision that's hard to undo, and the menu behind a recommendation shapes it — a broker can compare both paths but can only enroll you in plans they hold contracts to sell.

A good answer is "yes, argued, in writing" — with the trade-offs of each path named.

Jason's answer: That comparison is the whole assignment — both paths, priced and argued, in a written report you keep.

9. "Will you run the comparison with my actual doctors, drugs, and pharmacies?"

Why it matters: recommendations you can't see the work behind are testimony, not analysis.

A good answer shows you the results, not just the conclusion.

Jason's answer: Yes — the written report shows the comparison, and you keep it.

10. "How will you verify my doctors and prescriptions are actually covered?"

Why it matters: provider directories and formularies — the list of drugs a plan covers and at what cost — change. A careful helper verifies against the plan's current lists, not memory, and encourages you to confirm directly with providers and plans. This is a question good brokers win: the ones who do annual reviews do this constantly.

A good answer is a verification step you can watch happen, plus "confirm with the plan before you enroll."

Jason's answer: Against the plan's current directory and formulary lists at analysis time — with that same caution repeated in the report: confirm with the plan before enrolling.

11. "What do you need from me before you'd recommend anything?"

Why it matters: a recommendation that arrives before your doctor list, prescription list with dosages and pharmacy, other coverage, and budget is a recommendation for someone else.

A good answer is a list of homework for you.

Jason's answer: Doctors, prescriptions with dosages, pharmacy, other coverage — employer, retiree, VA — your state, travel, budget, and what you're worried about.

12. "What will my whole year cost — a normal year and a bad one?"

What is my worst-case year? The premium is the only number designed to be seen; the worst-case year is the number that hurts. In 2026, federal limits allow Medicare Advantage in-network out-of-pocket maximums up to $9,250 — $13,900 combined with out-of-network on a PPO (CMS limits) — and those maximums can sit behind a $0 monthly premium.

A good answer prices both a normal year and a bad year, with deductibles, drug tiers, and the out-of-pocket maximum in the math.

Jason's answer: Yes — both paths, normal year and bad year, in writing.

13. "If I pick Medicare Advantage now, what would switching to Medigap take later?"

Why it matters: the doors are not symmetric. Leaving Medigap for Medicare Advantage is easy; coming back usually means medical underwriting — health questions that can mean higher premiums or a decline — unless a limited federal window applies: the one-time six-month Medigap open enrollment that starts the first month you have Part B and are age 65 or older, or the 12-month trial right if you joined Medicare Advantage when first eligible at age 65 (medicare.gov, "When can I buy a Medigap policy?"). A helper who doesn't raise this unprompted hasn't finished explaining the decision.

A good answer raises underwriting before you ask.

Jason's answer: Covered in every Medigap-vs-Advantage analysis, including which windows and rights apply to you specifically.

14. "Who does the enrollment paperwork — and who calls me next fall?"

Why it matters: help has a lifespan. Enrollment is a transaction; next fall's plan changes, denied claims, and formulary shifts are the aftercare. Ask who does each part.

A good answer is honest about both halves, whoever gives it.

Jason's answer: Not me, on either count. Florida law forbids an unaffiliated agent from transacting or servicing an insurance contract (Florida Statutes 626.311(6)) — to enroll, you have real choices: medicare.gov, a phone call with the plan's representative or 1-800-MEDICARE, or a broker or insurance agent; the written report walks you through whichever path you pick. A broker handles enrollment for you and typically services the policy in later years; that is a real advantage of the commission model. What this practice offers instead is defined in writing — follow-up windows by package — and SHIP's free counseling covers questions and appeals year-round.