3 Questions to Ask Every Medicare Prospect

In the last video we walked through the five-step conversation framework. Step three was identify needs, and I mentioned three specific questions that drive every Medicare decision. Those three questions are so important that they deserve their own training. If you memorize nothing else from this entire track, memorize these. They are the foundation of every recommendation you'll ever make.

Question one. What doctors do you see and what hospitals or health systems do you use? This question tells you whether network matters. If a client sees three specialists at a major hospital system, you need to make sure any plan you recommend includes that system in its network. If the plan doesn't, it doesn't matter how good the premiums are or how many extra benefits it offers. The client can't use it the way they need to. On the other hand, if a client only sees a primary care doctor once a year for a checkup, network flexibility may be less of a priority and they may have more options. Let the answer guide you. Don't assume. Ask, and then verify the providers are in network before you make a recommendation.

Question two. What prescriptions do you take? Drug coverage is one of the biggest factors in plan selection, and it's the one most likely to surprise a client if you get it wrong. Every Part D plan and every Medicare Advantage plan with drug coverage has its own formulary. That means a medication covered at a low cost on one plan could be a high-tier specialty drug on another, or not covered at all. You need the client's full medication list, including dosages. Then you run those medications through the plan's formulary tool to see what their actual cost would be on each plan you're considering. A $20-a-month difference in premium means nothing if one plan charges $400 more per year for their prescriptions. This question protects the client from a bad surprise and it protects you from a phone call three months later asking why their medications cost so much.

Question three. What's your comfort level with monthly premium versus out-of-pocket cost when you use services? This is the question that helps the client understand the real trade-off between Medicare Supplement and Medicare Advantage, and between different plan tiers within each. Some clients want to pay more each month so they never have to worry about a surprise bill. Those clients often lean toward a Medicare Supplement plan where the premium is higher but the out-of-pocket exposure when they actually use services is minimal. Other clients are healthy, rarely go to the doctor, and would rather keep their monthly cost as low as possible, accepting that they'll pay more if something happens. Those clients may be a fit for a Medicare Advantage plan with a lower or zero-dollar premium but higher copays and coinsurance when they use care. Neither answer is wrong. Your job is to understand their preference and match it to the right plan structure.

Here's why these three questions matter so much. Everything else in a Medicare conversation is secondary. Benefits like dental, vision, hearing, gym memberships — those are nice to have. But the three things that determine whether a plan actually works for a client day to day are whether their doctors are covered, whether their medications are affordable, and whether the cost structure matches how they think about money. If you get those three right, the client is well served. If you get any of them wrong, it doesn't matter what extras the plan includes.

One more thing. Ask these questions every time, even when you think you already know the answer. A client you helped last year may have new medications this year. They may have switched doctors. Their financial situation may have changed. Never assume the answer is the same as last time. The three questions reset the conversation and make sure your recommendation is based on where the client is right now, not where they were 12 months ago.

Your action step is to practice asking these three questions out loud until they feel natural. Doctors and hospitals. Prescriptions and dosages. Monthly cost versus out-of-pocket cost. If you can ask all three within the first five minutes of an appointment without it feeling like an interrogation, you're in control of the conversation and you'll make better recommendations every single time.

Keep it conversational. Instead of a rapid-fire list of questions, ask it like you're curious: "Who's your primary doctor these days?" and then follow with "Do you see any specialists regularly?" and "Which hospital system are they affiliated with?" Write it down in front of the client so they see you taking their information seriously. Most clients will name their doctor, then remember a specialist, then mention another one halfway through the appointment. Leave room for that. If they draw a blank, ask them to grab their insurance card or a recent bill — it will usually have the provider network listed.

You need drug name, dosage (milligrams), and frequency (how many times per day). Generic vs. brand matters too. Dosage is where most agents get lazy — "Lipitor" isn't enough, you need "Atorvastatin 40mg once daily." Without dosage, the formulary tool can't give you accurate pricing. Ask the client to grab their prescription bottles or their pharmacy's printout. If they're on five or more medications, it's always worth the extra two minutes to get it right. Cost differences across plans can run hundreds of dollars per year on a single prescription.

Reframe it in plain language: "Would you rather pay a little more each month so that if you ended up in the hospital, you'd owe very little? Or would you rather keep your monthly cost as low as possible and take the chance that if something big happens, you might owe more?" Most clients can answer that version. You can also ask them how they think about other expenses — car insurance, for example. Clients who carry a low deductible to avoid surprises usually lean Medicare Supplement. Clients who carry a high deductible to save on premium usually lean Medicare Advantage.

Yes. It only takes three or four minutes and it prevents the most common mistake in this business — recommending a plan based on last year's information. Doctors retire or leave networks. Medications change as clients age. Financial situations shift when a spouse passes or a client retires fully. If you skip the three questions on the annual review, you are assuming nothing has changed, and that assumption is what turns a loyal client into a chargeback or a complaint. Ask them every time, even if you've known the client for a decade.

Be upfront about it. Tell the client the specific plans you can offer and which of their providers are covered under each. If their preferred doctor is only in a plan you can't write, say so — they will trust you more, not less, for being honest. Then ask whether the doctor is important enough that they'd want to stay with that provider even if it means a plan from another source, or whether there's flexibility to find a comparable in-network doctor. Clients appreciate the straight answer, and a referral back to you for other needs often comes from that kind of honesty.