How to Choose a Medicare Agent You Can Actually Trust

Enrolling in Medicare should feel like a step toward peace of mind. Instead, for many people, it feels like stepping into a maze. Mailboxes fill with offers, phone calls pile up, and every agent seems to promise they can help you find the “perfect” plan. But behind the noise, one question lingers: who is really on your side?

The truth is, not all Medicare advice is created equal. Some agents genuinely want to help you make the best choice for your health and future. Others are more focused on getting you signed up quickly—sometimes steering you toward plans that benefit them more than they benefit you. That’s why knowing how to tell the difference is so important.

If you want to make a confident decision, start by asking three key questions. These questions will reveal whether an agent is truly committed to your best interest—or just looking to make a sale.

1. Are you an independent broker or a captive agent?

This distinction makes a big difference. Independent brokers work with multiple insurance companies, which means they can compare a wide range of plans and recommend the option that best fits your needs. Captive agents, by contrast, represent only one insurance company. That’s the only menu they can offer—even if a better plan exists somewhere else. In many cases, that means you won’t even hear about potentially better options. If you want real choice and flexibility, look for an agent who is independent and able to shop around on your behalf.

2. Do you offer both Medicare Advantage and Medicare Supplement plans?

Some agents only promote Advantage plans, not because they are always the best option, but because they tend to pay higher commissions. A trustworthy agent will explain both paths clearly—outlining the pros and cons of each—so you can make the decision based on your health, preferences, and budget. Advantage plans often come with lower premiums, but you may face higher out-of-pocket costs, network restrictions, and requirements for pre-approval. Supplement plans usually have higher premiums, but they also offer more predictability, freedom to see any doctor who accepts Medicare, and fewer barriers to care. If your agent avoids one side of the conversation or can’t explain both options in detail, it may be time to look elsewhere.

3. Will you help me find the right prescription drug plan?

Drug coverage is often one of the biggest healthcare costs people face in retirement. Even if you’re not taking any prescriptions now, that can change fast. Some medications can cost thousands each month without proper coverage. Unfortunately, many agents don’t help with Part D plans because there’s little financial incentive. But the right drug plan can make a huge difference—not just today, but in the years to come. You want someone who will take the time to review your current medications and pharmacy preferences, and help you choose a plan that fits. Even better, someone who will check in each year to make sure you’re still in the most cost-effective option. That’s why we’ve built a simple online tool that lets our clients update their prescriptions and pharmacy preferences. From there, we help find the best-value plan available in their area—every single year.

One last thing to consider

Drug coverage is often one of the largest healthcare expenses people face in retirement, and the right Part D plan can make a dramatic difference in your costs. Even if you don’t take medications today, that can change quickly, and some prescriptions cost thousands of dollars a month without proper coverage. Unfortunately, many agents skip over Part D because there’s little financial incentive to spend time on it. But you deserve someone who will review your current prescriptions, consider your pharmacy preferences, and help you select the most cost-effective option. Even better, look for an agent who will review your drug coverage each year to ensure you’re still in the best plan as your needs and the market change.

You Deserve a Guide You Can Trust

Choosing Medicare coverage is a big decision, and it’s not one you should have to figure out on your own. A trustworthy agent won’t rush you, pressure you, or leave you confused. They’ll take the time to listen, explain your options, and help you make a confident choice. That’s exactly what we do at Medicare School. Our licensed agents are here to guide you through every step—and we’ll continue to support you long after you enroll. Ready to get started? We’d be happy to walk you through your options. Schedule a free call with one of our trusted Medicare agents or call directly at (800)-864-8890.