Open Enrollment Guide for Employers: Checklist and FAQs

Open enrollment season is one of the most important times of year for employers and HR teams. It is also one of the most challenging. From ensuring compliance and keeping costs under control to fielding employee questions, the process can easily become overwhelming without a plan.

This guide combines a practical open enrollment checklist with the most common employee questions you are likely to hear. Whether you are a small business or a large employer, following these steps will help you run a smooth, efficient, and compliant open enrollment period.

Table of Contents

• Open Enrollment Checklist for Employers
• Common Questions Employees Will Ask During Open Enrollment (With Answers)
• Final Thoughts About Running A Successful Open Enrollment Period
• Frequently Asked Questions About Open Enrollment (FAQs)

Open Enrollment Checklist for Employers

Step 1: Prepare Before Enrollment Begins

• Review last year’s open enrollment successes and challenges.

• Survey employees to identify preferred benefits and communication methods.

• Meet with your benefits broker to evaluate plan performance and costs.

• Select benefits offerings such as medical, dental, vision, life, disability, and HSAs. What about a wellness program?

• Confirm compliance with ACA and other legislative requirements. F

• List and promote any new or enhanced benefit offerings.

• Compile all necessary materials: plan summaries, rates, enrollment forms, FAQs.

• Announce open enrollment dates at least one month in advance via an email or internal communications platform.

• Set up or update your online benefits platform for easy access.

• Schedule reminders, including one the day before enrollment opens.

Step 2: Stay Organized During Open Enrollment

• Distribute benefits materials to employees early.

• Provide clear instructions for completing forms.

• Offer Q&A opportunities (like webinats) and encourage employee questions.

• Send reminders as deadlines approach.

Step 3: Follow Up After Enrollment Ends

• Check enrollment forms for completion and accuracy.

• Verify compliance with benefits laws.

• Submit enrollment data to carriers promptly.

• Update HR and payroll systems with employee elections.

• Share contact details for ongoing benefits questions.

Common Questions Employees Will Ask During Open Enrollment (With Answers)

1. What is the difference between an HMO and a PPO?

• HMO (Health Maintenance Organization): Employees must choose doctors and hospitals within the HMO’s network, and referrals are typically required to see specialists. The trade-off is lower premiums and lower out-of-pocket costs.

• PPO (Preferred Provider Organization): mployees can see both in-network and out-of-network providers without referrals. Out-of-network care usually costs more, but the plan gives greater flexibility in choosing providers.

In short: HMOs are more affordable but more restrictive. PPOs cost more but give employees more freedom.

2. What do premium, deductible, coinsurance, and out-of-pocket limit mean?

• Premium: The amount taken from each paycheck for insurance.

• Deductible: The amount employees pay before insurance begins covering costs.

• Coinsurance: The cost-sharing percentage after the deductible. Example: 80/20 means insurance covers 80% while the employee pays 20%.

• Out-of-pocket limit: The maximum an employee pays in a year, not including premiums.

3. Why do premiums increase each year? 

Healthcare costs rise due to advanced technology, specialized treatments, and prescription drug costs. Employers and employees both share this increase. KFF reports that annual premiums for employer-sponsored family health coverage have risen steadily, with 2023 averages surpassing $23,000 per family.

4. How do taxes impact employee benefits? 

Employees can confirm if their benefits are deducted from wages on a pretax or after-tax by checking their pay stubs.

• Pretax benefits (like medical, dental, vision, and FSAs under a cafeteria plan) are deducted before taxes, reducing taxable income and increasing take-home pay. Because employees already receive tax savings through payroll deduction, they cannot claim those pretax payments again as qualified medical expenses on their tax return.

• After-tax benefits are deducted after taxes, so they do not reduce taxable income. However, employees may be able to claim certain after-tax medical expenses as deductions when filing taxes.

5. How do I choose the best plan based on the options available? 

Encourage employees to compare:

• Monthly cost vs. expected usage — a lower premium may mean higher out-of-pocket costs later.

• Provider network — whether their preferred doctors and hospitals are included.

• Family needs — prescriptions, dependents, or ongoing care requirements.

• Flexibility — whether they want more choice (PPO) or lower cost (HMO).

Tip: Offer employees access to side-by-side plan comparison tools in your benefits platform so they can make informed decisions.

6. What if my spouse already has coverage or I'm a dependent under another plan?

Employees may still be able to:

• Waive coverage if they are covered elsewhere.

• Enroll in specific benefits such as dental or vision, even if they decline medical coverage.

• Review coordination of benefits rules, which determine which plan pays first if both plans cover the same person.

Encourage employees to compare total costs (premiums, deductibles, and out-of-pocket expenses) between the employer plan and their spouse’s or parent’s plan before making a decision.

Final Thoughts About Running A Successful Open Enrollment Period

A well-run open enrollment process improves employee satisfaction, keeps your company compliant, and saves administrative time. By following this checklist and preparing answers to the most common employee questions, you can approach this year’s enrollment season with confidence.

Ready to simplify open enrollment?

Frequently Asked Questions About Open Enrollment (FAQs)

©2025 - Content on this blog is intended to provide helpful, general information. Because laws and regulations evolve, please consult an HR professional or legal expert for guidance specific to your situation.