A blog about Medicare. What you and your employees need to know

Unclutter – The Top 5 Questions Transitioning Employees Ask

Author: Lora Drummond

Medicare Transition Specialist

Posted: 01/25/2021


Solution #4  Unclutter – The Top 5 Questions Transitioning Employees Ask 

No one can deny that Medicare is complicated. Between when to enroll and what all the Medicare parts mean and which plans cover what and what parts of Medicare do folks actually need- It’s a downright puzzle!  And searching for answers doesn’t help folks solve the puzzle easily either.

That’s why the stress-free way to go is to partner with experts who provide solutions to these puzzling dilemmas daily. 

The Medicare Architects team are Medicare puzzle masters! This leads me to mention two benefits for your employees!

  1. One of the benefits of having a Medicare transition team as a partner is ready access to experts when employee questions come up, or employees need guidance.
  2. The second benefit is to minimize the risks of mistakes later for employees who don’t understand Medicare enrollment processes or didn’t plan for their transition.

You likely have several kinds of employees who will resource you in the future for guidance including:

  • Pre-retirees starting to ask questions to plan for when they leave their employer.
  • Folks turning 65 and still working who don’t know if they need to enroll in Medicare.
  • People 65 or older who are exiting and have no prior information on what Medicare is or what to do.

We sponsor free CMS-approved Medicare workshops every month so that employees can learn the basics of Medicare. At the end of each of those workshops, attendees can ask our experts questions. I have compiled a list of 5 common questions employees ask during these sessions and threw in a bonus detail about COBRA benefits and Medicare.

I turned 65 last month but want to continue working. Do I need to sign up for Medicare?

Not necessarily. If you are covered under an employer plan you can stay on that employer plan. However, it depends on a few factors like your company’s size and if the plan you are on is considered ‘creditable,’ meaning it’s a health benefit plan that meets a minimum set of qualifications equal to or better than Medicare.

 Employers with 20 or fewer employees should be versed in basic Medicare information to guide employees to enroll when they are turning 65. Employees can continue their employer plan and coordinate it with Medicare if it makes sense to carry both, but enrollment will be essential when eligible and cannot be deferred without a penalty when enrolling later. 

For companies with more than 20 employees, Medicare usually can be deferred without an enrollment penalty later.

Having a Medicare expert to help you confirm whether or not to enroll while still working provides peace of mind, so it’s worth a call to avoid stress later.

My company has great benefits; should I consider Medicare while I’m still working?

People are uniquely different. They have different needs. We act as a fiduciary, so we can guide you as an individual. We want you to be able to compare your current plan and Medicare options side by side. We provide the opportunity for you to compare costs and benefits to help you determine which plan works for your specific needs. We also have a tool that helps do that math for you called the Stay or Go Analysis. So you can see the math to decide for yourself. Sometimes Medicare offers opportunities a group plan doesn’t.

So it is useful when you have a Certified Medicare Planner® to help you compare.

If I delay signing up for Medicare while still working, will I suffer a penalty later?

Suppose you are covered by a creditable employer group plan. In that case, you can defer your Medicare enrollment until you are ready to leave your employer without a penalty when you enroll later.

Having a trusted expert to help you confirm your decision to defer enrollment provides you with peace of mind and can help you create a confident glide path later on what to do when you are ready to retire.

I will be new to Medicare in 6 months. What do I need to do first?

We like to meet with folks 6-9 months before they need Medicare. That way, you understand Medicare and your options and can make fact-based and confident decisions without insurance companies telling you what they think you need.

If I’m covered by employer insurance and not receiving social security, can I enroll in Part A since it’s free?

If you are eligible for Part A, you certainly can turn on your Part A benefits while working and continue your employer plan. However, there is a caveat to turning on Medicare. Once you begin receiving Medicare benefits, you can no longer contribute pre-tax dollars to an HSA savings account. Suppose you wish to continue contributing to your account. In that case, you need to delay enrollment in Part A and Part B. (Note that you cannot delay or opt-out of Part A if you receive any Social Security benefits (retirement, disability, or spousal).

This is another important topic for discussion with your Certified Medicare Planner® to make sure you understand the effects of turning on Part A while still working.

I am 65 and have just been laid-off. Can I extend my group benefit by taking COBRA rather than go on Medicare?

If you leave your employer before you are 65, you CAN go on COBRA only until you are eligible for Medicare. If you are 65 or older when you leave your group plan, you must enroll in Medicare – you cannot defer it. You can’t have COBRA if you are eligible for Medicare. 

If you have a spouse and dependents that will lose benefits when you leave, you still should not defer your Medicare to keep their coverage. A Certified Medicare Planner® can help you enroll in Medicare and provide guidance on where to search for plans to cover your family members.

Don’t leave that puzzle unfinished on your employee’s desk – or your desk for that matter. Engage your puzzle masters to help your employees find the pieces that fit their needs when planning for Medicare.

Let us help unclutter Medicare guidance for your employees in 2021.

Unclutter Medicare

By adding dedicated Medicare resources you are adding unrealized total rewards and providing more choices for your employees. Create a compliant Medicare benefit support plan. Give your employees personal guidance from a team of experts that will follow them after they retire.

You can receive helpful Medicare resources, and tips and tricks to build your Medicare transition strategy just by signing up to receive a blog article a week delivered to your email. ( We promise only one per week and you can opt-out at any time)

Plus get early notifications of any NEW helpful resources and Medicare news!  SIGN UP BELOW!


Your Medicare Transition Partner
– Lora

Helpful Links

Get the latest reason you need a Medicare transition team right in your inbox!

2021 TMA Medicare Guide image
65 and Counting Talk Show

Subscribe to Medicare@work

Get the latest reason you need a Medicare transition team right in your inbox!

Other Posts from Medicare@work

Stay Tuned! Medicare Help for Business is Here

Stay Tuned! Medicare Help for Business is Here

Don’t adjust your dial! Our Medicare help for businesses is now more accessible than ever. Stay tuned to your favorite social media sites for links to enjoy helpful topics for guiding employees with their options regarding Medicare. When folks turn 65, they have more healthcare choices. We are here to help!

Contact Us

(800) 568-1095

Brought to you from Scottsdale, AZ

Monday-Friday: 9am – 5pm

Get Started

Meet your dedicated Medicare Transition team today!
Share This