HR Managers Need to Know THIS About Medicare

Hello Toni,
I’m an HR Manager for a local oil and gas company and have a question about an employee who is turning 65. His situation is a little unconventional. Next month, he’ll begin receiving chemotherapy for lung cancer. I’m not sure how to advise him because technically he’s working full-time.
He has 5 months of pay from unused vacation time that he can use while recuperating. This helps him keep his status as a full-time employee.
Our firm has over 100 employees, and I’ve been told there are certain rules based on company size. On behalf of the employees of my company, how can I make sure that I have the correct answer to my questions?
Thank you,
Katie from Tampa, FL
Hi Katie,
Your employee with cancer is approaching his Initial Enrollment Period. For reference, this period begins three months before his 65th birthday month and ends three months after his 65th birthday month. Many Americans don’t enroll in Medicare when turning 65. Generally, it’s because they (or their spouse) are still working at a company with over 20 employees. Through their employer, they typically have group health insurance. This rule can protect your still-working-full-time employee with health issues.

Now, readers, let us talk about who will pay your claim first. This depends on how many employees are on your company’s group health plan.
For further information, see the chart on page 21 of the “Medicare & You handbook on number of employees.)
If you are:
- 65 or older
- Work in a company with 20 or more employees
- Are married to someone who works in a company with 20 or more employees Then group health insurance pays first. (Please verify there are 20 or more employees enrolled in the employer group health plan). (It may be to your advantage to delay enrolling in Medicare without receiving a Part B penalty.)
Then group health insurance pays first. However, if there are fewer than 20 employees where you (or your spouse) work and receive benefits, then Medicare pays first. Simple enough, right?
Medicare Continued…

Katie, below is a checklist that might make your HR job easier:
- Verify your employees’ options by calling your company’s health insurance plan to discover how the plan coordinates with Medicare.
- Understand that it may be to an employee’s advantage to delay Part B enrollment. See the Medicare & You handbook under “Should I Get Part B?” or in Chapter 1 of my book Medicare Survival Guide: Advanced Edition for more clarification.
- Remind employees aged 65 and older to contact their local Social Security office immediately to enroll in Medicare if their work status changes from full-time to part-time, laid-off, or retired. Alternatively, they can visit Medicare.gov.
They will need to file the Social Security forms to avoid the “famous” Medicare Part B penalty. At this point, they’ll be eligible for a SEP (special enrollment period) and should enroll in retiree benefits, such as a Medicare Supplement or Medicare Advantage plan. Note that COBRA and retiree insurance aren’t considered current employer insurance, so don’t delay in enrolling in Medicare Parts B and D (Medicare’s prescription drug plan).
Readers, there are specific Medicare rules regarding leaving employer benefits after turning 65. Learning when, and how, to change Medicare plans is especially vital for an employee such as Katie’s. While Medicare is confusing, it doesn’t have to be.
Contact Toni: Email the Toni Says® Medicare team at [email protected] or call (832)519-8664 for all your Medicare questions!
Check out Toni’s interview with the co-author of the “Chicken Soup for the Soul” book series!
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Originally published August 16, 2023







