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Employee Benefits

5 Common Open Enrollment Mistakes

By October 9, 2025December 4th, 2025No Comments

Having spent years as an HR Director before transitioning to a role as an Employee Benefits Consultant, I have seen firsthand how crucial open enrollment can be not just for employees but for the HR teams guiding them. Open enrollment is not simply a deadline on the calendar. It is the time when employees make critical decisions about health insurance, dental, vision, life insurance, and other benefits that directly impact their financial and personal well-being for the year ahead.

Unfortunately, many employees approach this period hurriedly or without proper guidance, which can result in costly errors or missed opportunities. These mistakes are disruptive for both employees and HR.

Based on my experience, here are the most common mistakes employees make and how HR can proactively help them avoid these pitfalls.

1. Waiting Until the Last Minute

Procrastination is one of the biggest hurdles during open enrollment. When employees wait until the final days to review their benefits, they’re more likely to make rushed decisions, overlook resources, or miss opportunities altogether.

How HR can help:

• Start communications early. Provide materials at least a few weeks before enrollment opens and highlight important deadlines in every reminder.

• Offer multiple touchpoints. Host Q&A sessions, webinars, or drop-in office hours to ensure employees understand their options.

• Encourage early action. Remind employees that waiting until the last minute could lead to errors, technology issues, or unanswered questions.

2. Assuming the Most Expensive Plan Is the Best

Employees often believe that higher premiums equal better coverage. While comprehensive plans may fit certain needs, they aren’t always the most cost-effective option. On the other hand, lower-cost options like high-deductible health plans (HDHPs) may appeal to some employees but can leave others unprepared for out-of-pocket expenses.

How HR can help:

• Provide plan comparison tools. Side-by-side breakdowns of costs, deductibles, and coverage can help employees make data-driven choices.

• Encourage self-assessment. Urge employees to review last year’s medical expenses and consider anticipated needs such as prescriptions, maternity care, or surgery.

• Educate on risk vs. reward. Help employees understand how premium costs, deductibles, and out-of-pocket maximums impact their total financial exposure.

3. Overlooking FSAs and HSAs

Flexible Spending Accounts (FSAs) and Health Savings Accounts (HSAs) are valuable tools for managing health care costs, but they are often underutilized. These tax-advantaged accounts can make a meaningful difference in employees’ financial wellness.

• HSAs (available only with HDHPs) provide a triple tax advantage: pre-tax contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. Funds also roll over indefinitely.

• FSAs allow pre-tax contributions for health care costs but have annual “use it or lose it” restrictions, with limited rollover.

How HR can help:

• Highlight the savings potential. Use examples to show how much employees could save in taxes and out-of-pocket costs.

• Clarify eligibility rules. Make sure employees know the difference between FSAs and HSAs so they don’t miss out on opportunities.

• Promote contributions. Encourage employees to at least contribute enough to cover predictable expenses like prescriptions or copays.

4. Not Learning From Past Mistakes

Many employees don’t take the time to reflect on last year’s benefits choices, which means they risk repeating the same mistakes. They may have overpaid for coverage they didn’t use, failed to take advantage of available programs, or skipped necessary care due to cost confusion.

How HR can help:

• Encourage reflection. Provide employees with year-end benefits and usage reports if possible.

• Prompt with questions. Ask employees to consider: Did your plan meet your needs? Were there unexpected costs? Did you use available wellness programs or savings accounts?

• Promote education. Use lessons learned to guide employees toward plans that better align with their needs this year.

5. Overlooking Enrollment Errors

Even when employees make the right elections, administrative errors can happen. The Nava Benefits audit revealed widespread issues such as employees being enrolled in the wrong plan, dependents not being added correctly, or deductions being miscalculated. Once the new plan year begins, these mistakes are difficult to correct.

How HR can help:

• Encourage verification. Remind employees to double-check their confirmation statements for dependents, coverage levels, and payroll deductions.

• Create a checklist. Provide employees with a step-by-step guide to review their elections before submitting.

• Offer support. Make HR accessible for quick corrections before enrollment closes.

Setting Employees Up for Success

Open enrollment is more than a compliance task. It is an opportunity to empower employees, enhance satisfaction, and strengthen your benefits strategy. When employees make informed decisions, they benefit personally while your organization reduces errors and improves retention.

I know that clear communication, proactive education, and verification processes are key to success. Partnering with a knowledgeable benefits advisor can also ensure that your open enrollment process runs smoothly, reduces administrative mistakes, and provides employees with benefits that truly meet their needs.

At McConkey Insurance & Benefits, we work with employers to streamline communication, optimize plan offerings, and provide the guidance needed to make each open enrollment period a success for employees and HR teams alike.

Michelle Collier

Employee Benefits Consultant | Contact me at mcollier@ekmcconkey.com or (717) 505-3150. Click here to read my bio!

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