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When Choosing or Using a Medicare Advisor, Ask These 5 Questions


If you’re contemplating choosing a Medicare plan and feel overwhelmed - you’re not alone.

Medicare is confusing! Each plan has different premiums and many plans have different benefits, prescription costs, and networks of healthcare providers. It is hard to compare the benefits of each plan and understand the trade-offs. That’s why many people use a Medicare advisor, agent, or broker to help choose coverage. Insurance companies are prohibited from charging a different premium if you use an agent instead of purchasing directly from the carrier. 


But how do you choose a Medicare advisor? Here you are the five most important questions we recommend asking when choosing to work with a Medicare advisor. 

5 Questions to Ask Any Medicare Advisors You Are Considering Working With

1. Does the advisor search every single Medicare plan in your area? 

A sad secret is that most Medicare advisors search only the subset of insurance companies that pay them commissions. This could be one plan, five plans, or any number. There is no legally required minimum. 

Most Americans have more than 50 Medicare coverage options available in their area. There are meaningful differences across costs and coverage for these plans. So it’s important to search them all. 

It is important to ask if any advisor you consider working with is searching every single carrier to ensure you are getting the best coverage that is right for your individual needs. 

2. Does your advisor consider the credit rating of the carrier?

Did you know like many other businesses, insurance carriers sometimes go out of business? It’s rare, but when it happens it can be very disruptive. 

This is one reason why it’s so important to confirm the insurance company you choose has a strong financial rating. This rating, typically known as an AM Best Rating, indicates the financial strength of the carrier. A strong AM Best rating indicates that a particular carrier is unlikely to be at risk of going out of business. 

3. Does your advisor forecast future premium changes in plans to help clients understand future cost exposure? 

If you initially consider signing up for a Medicare Supplement plan -- also known as a Medigap plan -- an agent will typically offer you a quote with initial monthly premiums. However, it is best practice not only to check your initial premium, but also what your future premiums might be over time. This is particularly important because many older Americans are often surprised by future rate increases. Make sure any advisory you are considering assesses potential future premium increases across carriers, in addition to current premium rates. 

4. Does your advisor take into account the doctors you see, the prescriptions you take, and your care priorities? 

Most advisors will ask you for your primary care physician to confirm that your doctor is covered in plans that are recommended. Some advisors will ask you for specialists like your cardiologist, neurologist, or nephrologist. 

It is important you also ask  whether the advisor considers all doctors important to you. This includes doctors you see several times a year as well as the ones you see once a year. 

If you are considering a Medicare Supplement, it’s particularly important to ask the advisor to triple-check that all your preferred physicians take Original Medicare. If they don’t accept Original Medicare, a Medicare Supplement plan won’t provide coverage.

Lastly, be certain the advisor prioritizes your drug coverage options based on your prescriptions. By choosing the optimal drug drug plan for their prescriptions, people often save thousands of dollars per year.

5. Ask an advisor, “Over the last month, have you recommended that at least 5 people choose  a plan that doesn't pay you commissions?”

The best advisors should put you at the center of every recommendation they make. Unfortunately, this doesn’t always happen. Most advisors can point to a few examples when they’ve done this, but it’s few and far between. The best advisors make this standard practice.  

We founded Chapter to be the Medicare Advisory organization that we wanted for our own families but couldn’t find. You can read more about our founding story here.

At Chapter, we designed our technology and tools to be able to answer “yes” to each of these questions. It’s the right thing to do and the right way to do business. 

Like other advisors, we do earn revenue from insurance companies. But the similarities stop there.


- We search every single plan, not just the subset that pay commissions. (We built our own proprietary database to enable this universal search.)

- We don't ever base our recommendations on whether we get paid, or how much. Your interests always come first.

- Our advisors' compensation is identical whether or not you choose a plan that pays us.

We would be honored for the opportunity to advise you and earn your trust. But it’s even more important that you get the best guidance, no matter what advisor you choose. We hope that you use this list of questions as you consider who to work with. We’re always here to help as well. 


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Ari Parker is Chapter’s lead Medicare advisor, Chapter’s co-founder and a Stanford trained lawyer. You can reach out to him at [email protected].

Cathy O’Brien is Chapter’s Director of Education and Partnerships. As a licensed advisor, she now supports large organizations and their employees  which builds on her 12 years of experience advising thousands of Americans. You can reach out to her at [email protected].

The number for their team is 605-205-8869.


While it would be a privilege to serve and advise you, it’s more important to ensure you get the best care, no matter which advisor you choose. We hope you leverage this list of questions during your research, and if you have any concerns, we’re here to help.

Get Medicare, Maximized