The 'broken handoff' leaving retirees lost on Medicare choices

Medicare enrollment form.
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  • Key Insight: Discover how a "broken handoff" from employers to Medicare advisers increases lifelong coverage costs.
  • What's at Stake: Unaddressed transitions raise employer healthcare costs and retention, plus compliance and reputation risks.
  • Supporting Data: 70 million Medicare enrollees; roughly 10,000 Americans turn 65 daily.
    Source: Bullets generated by AI with editorial review

Elizabeth Gavino compares it to being pushed out of a nest.

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When an employee retires after many years on a company-sponsored healthcare plan, they are often handed a COBRA notice and a last paycheck and given little advice about the transition to Medicare.

The decisions they make in the next few months — such as costly lifetime premium penalties for late enrollment and wrong plan choices — can follow them for years. Gavino, founder of Medicare Transition Partners, refers to this process as the "broken handoff."

Employees get lost in the shuffle because all of the people who are supposed to help them with the transition — from HR to brokers and financial advisers — think that someone else is taking care of it, Gavino says.

"Nobody knows that the employee is floundering," she says. " And when the employee goes back into HR, they're not getting the answers they need. They're just getting a form that might give them a little bit of an explanation and then they're sent on their way."

That's where Gavino, who has more than 30 years of experience in insurance, benefits and retirement strategy, com get es in. She works with companies and brokers to help employees prepare for the transition to Medicare before they retire, offering early-stage strategy, education and planning.

Most people are told to start planning about six months before they turn 65, but Gavino says that's far too late. "I argue that it should be a three-year window," she says.

Without clear guidance, people often rely on friends and family for advice, and Gavino says that's where they run into problems. Many Medicare beneficiaries describe the process of choosing coverage as "overwhelming and difficult" and say they lack confidence in their ability to compare options, according to the Kaiser Family Foundation.

"There's really a huge need for this and not enough people to do it and provide the value that's needed," Gavino says. "We need everybody working together to help educate."

A lack of understanding

As of January 2025, around 70 million U.S. adults were enrolled in Medicare coverage, according to the Centers for Medicare & Medicaid Services. That total continues to rise, with roughly 10,000 Americans turning 65 every day, according to the U.S. Census Bureau and aging into the program.

The average retirement age is 62, according to a recent MassMutual survey, but many people are staying in their jobs longer than they want because of uncertainty about health coverage.

"I see a lot of people delaying their retirement because they're afraid that they're not going to have good healthcare," Gavino says. "So they keep staying in a job that they don't want to work in anymore."

That hesitation can create ripple effects for employers as well. Workers who might otherwise retire continue drawing benefits, increasing costs for companies.  According to the 2025 KFF Employer Health Benefits Survey, the average annual cost of employer-sponsored health insurance reached $26,993 for family coverage and $9,325 for single coverage.

Read more: Here's how much employees need to save for healthcare in retirement

"Then the employer's paying for benefits that they shouldn't be paying because the person wanted to leave," Gavino added.

The issue is less about the availability of coverage and more about a lack of understanding. Many employees don't fully grasp how Medicare works, what steps they need to take, or whether they need to take action at all if they plan to keep working past age 65.

"With better education prior to retirement, everybody would know what the rules of engagement are and what their options are," Gavino says.

Advice for benefit leaders

Many benefit leaders spend their whole career trying to build a human-centric culture within their organization, Gavino says. But when companies fail to help soon-to-be retirees transition to Medicare, they can have an impact on the company's reputation.

"What was a happy time is now a very frustrating, upsetting time," Gavino says. "And if those people who are off-boarding still maintain relationships with their friends inside the company, that's when the bad conversations start to happen."


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