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8 Insider Tips to Take Advantage of the Next Medicare Enrollment Season

Updated: Apr 26

This article was written in partnership with Keen, based on content shared in a Hively discussion hosted by Scott Matthews, a licensed Medicare advisor from Keen.

Do you want to get ready to get the most out of the upcoming Medicare Annual Enrollment Period (AEP), starting 10/15? Read further to understand how Medicare sales really work from the inside, how you make smart choices, and make sure you are protecting yourself throughout the process.

Tip 1: Be smart and shop your Medicare plan each year Medicare is a business that has a lot of competition! Each year, plans change so you should be rethinking and shopping your plan each year. Yet 70% of Medicare beneficiaries do not shop each year, missing out on cost savings and benefits. Important dates to remember:

  • September - Annual Notice of Change

  • October 1 - 2024 plans released

  • October 15 - Enrollment begins throughout December 7th

Tip 2: Medicare is… complicated. You should probably get some expert help. One of our members who is a Physician once said, “If Medicare is confusing to me, I can't imagine how confusing it must be for others!” And it’s true - it can take 10 - 20 hours of work to do a good job of understanding and comparing plan options. There are so many choices, options, and some plans such as Medicare Advantage and Part D plans are highly non-standard with extra costs and medical benefits.

It may be to your benefit to speak to a licensed health insurance agent. They are well-trained and regulated, have the expertise to save you time (and give you a peace of mind), and usually monitored for compliance. Some helpful resources:

Tip 3: But, you should know your Medicare agent’s potential BIAS

Many agents sell a limited set of products, are paid primarily on sales commissions that vary by product, and often to get paid they must sell you a new plan. They can also be influenced by special incentives.

Tip 4: Be Medicare Advertising Savvy Have you ever seen one of the Medicare Coverage “Helpline” TV commercials, or Medicare help websites, or “official” and urgent looking home mailers? There’s a high chance that these are lead generators that just sell your information to different agents! Tip 5: Remember, CMS is on your side! You have rights. The Center for Medicare and Medicaid Services (CMS) is the federal agency that oversees Medicare. They regulate the activities of Medicare sales agents, and ensure calls are recorded, products can only be sold with your explicit permission, and require full disclosure. If you have a complaint about Medicare sales activity, you should report it to CMS or the relevant insurance company!

Fun fact: Complaints to CMS about Medicare marketing were up 100% in 2021! (source)

Tip 6 Take control of the Medicare sales call You should be ready to take control of the call with the Medicare sales agent. Ask their first and last name, national producer number (NPN), agency name, and direct phone number. Confirm with the agent that the call is being recorded. Ask for all the names of the insurance companies they represent, and check whether they sell both Medicare Supplement and Medicare Advantage plans. Lastly, ask how they are paid! Tip 7 Make sure the agent works in your best interest All agents should work in your best interest, but unfortunately not all do. Those who do will probably do the following:

  • Inform you of how you can learn about all of your options AND recommend options from all available plans on the market

  • Get your permission to discuss plans (“Scope of Appointment”)

  • Look up all your doctors, medications, and ask you about other related medical and social needs (e.g. dental, vision, hearing, transportation, nutrition)

  • Understand your financial situation (e.g. Medicaid, Extra Help, Medicare Savings Program)

  • Clearly explain all plan details

  • Support you after the enrollment as well

Tip 8 Understand your benefits and how to use them Unfortunately, many benefits typically go unused because of lack of awareness and/or the complexity of enrollment. Remember that often with your Medicare comes benefits such as but not limited to: In home care, flex cards, Food, gym access, hearing support, dental support, and even a personal emergency response system.


Yes, Medicare is confusing. Even Donna, a Hively member and physician, recalled how she had trouble understanding how Medicare is set up and the multiple challenging steps required. In hope of making this process easier for all of you, this content was produced in partnership with Keen. Keen is the “Genius Bar” for Medicare. They are independent experts you can trust, that work off of NO commissions, and show commitment to their clients with lasting long-term relationships.

With the enrollment season starting Oct. 15, Scott has offered a free 1-hour, no objective, no obligation Medicare consultation to our members.

To learn more about Keen, visit here.

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