Tips for a Successful Medicare Enrollment Season

With years in the Medicare business, I can tell you that success isn’t about luck. It’s about strategy. Medicare enrollment season can make or break your year, but with the right planning and focus, you can turn every quarter into an opportunity to serve your clients and grow your business. Success is not about chasing every opportunity frantically. It is about making wise, steady, and calculated moves. Whether you’re a seasoned agent or just getting started, the key to long-term success lies in your ability to plan effectively, build strong relationships, and execute with discipline.

Let’s break down each quarter and the best practices that will put you ahead of the curve.

If there’s one thing I’ve learned, it’s that helping seniors should be your priority. Seniors live on fixed incomes and are accustomed to their routines, so you should mirror that stability in your approach. You must be as reliable and consistent as the products you offer. Just like the best technology, you should aim to make the complex simple for your clients. Your clients value honesty and clear communication. When you approach your clients, don’t focus on completing a sale. Focus on providing value. Whether it’s keeping detailed notes, sending birthday cards, or being available when they call, these small efforts add up. Be there when they need you, help them understand their options, and build trust over time.

Remember, they’re pen-and-paper planners with an eye on the future—adopt that mindset, and your business will flourish.

Planning Your Leads for the Year

Leads are the lifeblood of your business. Knowing how many to work each quarter will ensure a steady flow of prospects and sales. Here’s a general lead guide to follow per agent each month:

Q1: 250 leads/month
Q2 & Q3: 500 leads/month
Q4: 100 leads/month

This quarterly strategy ensures you consistently have opportunities to build your client base without feeling overwhelmed.

Quarter 1

If you’re like me, you know the ADP (January 1 through March 31) is golden. The ADP (Annual Disenrollment Period) is a government-implemented dis-enrollment period directly after the Annual Enrollment Period (AEP), where clients who wish to disenroll from Medicare and start on a different plan can do so. This period is a gift. This period provides a way to help clients transition to plans that are a better fit if their initial choice isn’t working out. It’s your chance to do more than sell—it’s your chance to solve a problem. This situation is also a chance to strengthen relationships with existing clients and revisit prospects who didn’t commit during AEP.

Nurture Existing Clients –This is your time to shine as a trusted advisor. Contact your clients, ensure they are satisfied with their plan, and educate them about anything they may ask about. Remember that while you can’t outright solicit a change, you can certainly be the first person they think of if they’re unhappy with their coverage. Always be that agent who keeps the client’s best interest at heart. Pursue building trust, maintaining their satisfaction, and showing you’re there for the long haul.

Revisit Lost Opportunities – The most successful agents know that failure is only the beginning. It’s all about looking at the long-term. For every client who didn’t sign up during AEP, this instance presents your chance to reach out, reconnect, and show that you care beyond the sale. That kind of attention doesn’t go unnoticed, and when the time comes for them to make a change, they’ll remember who treated them like more than just a sale. After all, people don’t just buy products—they buy experiences. I have personally had clients who came back to me months later because they remembered my honesty and willingness to help without pushing a sale.

Quarter 2

Q2 is your moment to be proactive and maintain the connection with your clients. You’re not just their agent; you’re their healthcare advocate. During this quarter, you’ll want to focus on policy reviews, discussing life insurance options, and financial planning concerns. It’s also the perfect time to focus on those who are turning 65 or who qualify for Special Enrollment Periods.

Start Setting AEP Appointments Early

Q2 is a great time to start setting appointments for AEP. You heard that right—start now. Planning isn’t just good. It’s essential for building a strong book of business. You should already be booking appointments for AEP well in advance. Get ahead of the game, so when October 1st rolls around, you’re not scrambling—you’re ready to execute. The earlier you start, the stronger your foundation will be

Quarter 3

Q3 is about preparation—think AHIP, carrier certifications, and contracting. Don’t procrastinate here; the more you get done now, the more time you’ll have for client meetings during AEP. Trust me, I’ve seen agents scramble in September, and it’s not pretty. It’s a good idea to knock out the paperwork as fast as possible to keep yourself up-to-date and provide availability to meet client needs. You should have every day from October 1 through December 7 booked by the end of Q3. The difference between a successful agent and an unsuccessful one is preparation. If you prepare, you can write over 100 policies in AEP. If you don’t, then you’re lucky to hit 20!

Quarter 4

This quarter is your payday. All your preparation and hard work come to fruition from October 1 to December 7. Think of AEP as the harvest season—the time to execute, sell, and make the most of the opportunities you’ve prepared for all year. You’ve already laid the groundwork, and now it’s about going all in, staying focused, and giving it your best effort. Successful agents are busy from October 1st through December 7th. And when it’s over, don’t forget to take a moment to reflect, recharge, and celebrate your achievements. This is the moment you’ve built for all year.

Why Procrastination Kills Your Medicare Enrollment Count

Carrier Appointments

The earlier you complete your carrier appointments and certifications, the better. If you wait until the last minute to request carrier appointments or complete certifications, you’re setting yourself up for failure. Background checks take longer, servers bog down, and contracting staff get overwhelmed the closer we get to AEP. Trust me, I’ve seen agents wait until September and get stuck in the bottleneck. Plan and you’ll breeze through.

Certifications

Certifications are done online. That means a server is working the information and driving the certification classes. Servers get slower and crash with an overload of visitors. So, servers bog down and experience technical issues the closer we get to AEP. Additionally, once a certification is in, it needs to be verified by the carrier’s contracting staff. The closer we get to AEP, the heavier their workload.

Isn’t it easy to imagine how these setbacks could ruin a good selling season? Procrastination is the number one cause of agent failure during the selling season. Heck, procrastination is probably the number one reason agents fail all year long! If you write down all your tasks and check them off as you go, you will be much happier and significantly less stressed when the starting bell tolls.

Company Recommendations

We love a free tool called Trello for task management help. It is a great little utility and operates from your PC, Mac, or mobile device. Trello deals with macro-to-micro organization using Boards, Lists, and Cards, and works wonders for keeping you focused and helping you feel less overwhelmed when work piles on.

For example, you could use Trello to make a board about a broad topic like ‘Home Projects.’

Then, inside the board, you make lists: ‘Yard,’ ‘Patio,’ ‘Garage,’ ‘Craft Room,’ etc.

Inside the lists, you make cards. So, inside the ‘Patio’ list, you may have these cards (small tasks):

Prepare base
Lay Flagstone
Pots and Plants
Seating
Hot tub

Each card can have a full description, checklist, images, diagrams, and more nested neatly inside it. Plus, you can drag and drop cards to an archive list or right-click and archive them. If you are interested, you can get Trello for free by clicking here.

Some board, list, and card ideas for you, an agent:

Board: AEP Medicare Enrollment

Lists:

Basic Prep
- Make a list of all Medicare prospects
- Order ongoing Medicare leads
- Start Calling to set appointments for October 1 for MA prospect presentations
- Start setting appointments for every day of AEP on Outlook (book solid through Dec 7)
Certifications
- Get AHIP done as soon as it is available
- Get carrier certifications done as soon as each is available
Carrier Appointments
- Change Aetna, Humana, Cigna, and UHC to Empower Brokerage now
Plan Announcements
- Aetna
- Cigna
- Humana
- UHC
Walmart Store
- Store obtained
- Rules and deadlines
- Materials needed
- Plan of action

Agents

We hope that this information on medicare enrollment is useful to you.

Empower Brokerage is dedicated to helping you make informed decisions about your health and finances. Whether it’s through webinar training, one-on-one calls, seminars, or marketing plans, we want you to be successful!

Give us a call at 888-539-1633 or leave a comment below if you have any questions.

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This article was updated on 9/25/2024.