Open Enrollment Best Practices: A Guide for HR Teams

Why Open Enrollment Matters More Than You Think

Open enrollment is the one time per year when most employees actually stop and think about their benefits. It's your window to educate, engage, and help them make decisions that will affect their financial security for the next 12 months.

A poorly executed open enrollment leads to:

• Underutilization of valuable benefits (employees don't enroll because they don't understand what's offered)
• Employee confusion and frustration
• Missed tax savings opportunities (especially with pre-tax benefits)
• Increased support tickets after enrollment closes ("Wait, I thought I had dental?")
• Difficulty attracting and retaining talent (if your benefits package isn't communicated well, candidates assume it's weak)

A well-executed open enrollment, on the other hand, demonstrates to employees that you're invested in their wellbeing, maximizes benefit utilization, and reduces year-long confusion and support burden.

Timeline: Start Planning 90 Days Out

A successful open enrollment doesn't happen overnight. Here's a month-by-month breakdown that works for most organizations:

90 Days Before Enrollment Begins

Focus: Plan and Prepare

• Review current plan offerings and employee utilization data
• Identify what's changing (rate increases, plan improvements, new offerings)
• Begin renewal negotiations with carriers if needed
• Confirm vendor deadlines and requirements
• Audit your Section 125 cafeteria plan document to ensure it's current
• Assign roles and responsibilities for the enrollment period

60 Days Before Enrollment Begins

Focus: Create and Design

• Prepare communication materials: emails, posters, decision guides
• Update your enrollment platform (if using one) with new plans and rates
• Create plain-language summaries of each plan and what's new
• Schedule HR staff and any benefits consultants for Q&A sessions
• Prepare one-page decision guides ("If you're single," "If you're a family," etc.)
• Draft reminders for key dates in the enrollment window

30 Days Before Enrollment Begins

Focus: Launch Awareness

• Send the first "coming soon" announcement to all employees
• Host a preview session (optional but helpful for large organizations)
• Post materials on your intranet or benefits portal
• Begin multi-channel marketing: emails, Slack/Teams messages, posters, physical mailings for remote workers
• Make sure all managers understand the timeline and can answer basic questions

During the Enrollment Window (2-3 Weeks)

Focus: Support and Engagement

• Offer live Q&A sessions daily or multiple times per week
• Make one-on-one support available (phone, email, video call)
• Send reminders at key intervals: 1 week remaining, 3 days, last day
• Monitor enrollment progress and follow up with employees who haven't enrolled (if your benefits require affirmative election)
• Be available to troubleshoot enrollment platform issues immediately

Immediately After Enrollment Closes

Focus: Confirm and Process

• Verify that all elections processed correctly in your enrollment system
• Send each employee a confirmation of their elections
• Transmit elections to carriers and payroll (on time)
• Update payroll deductions to reflect the new plan year
• File required documentation (Section 125 plan certifications, etc.)
• Address any remaining questions or errors

Communication Strategies That Work

The biggest mistake HR teams make during open enrollment is thinking one communication is enough. Employees need multiple touchpoints, in multiple formats, with consistent messaging.

Multi-Channel Approach

Don't rely on email alone. Employees consume information differently:

• Email: Formal announcements, reminders, detailed information
• Slack/Microsoft Teams: Quick updates, reminders, casual tone
• Physical mail: For remote workers who aren't checking company channels daily
• In-person sessions: Live Q&A where employees hear directly from HR
• Intranet/Portal: Central hub where all materials live

Plain Language Is Essential

Avoid benefits jargon. "PPO" and "coinsurance" mean nothing to most employees. Instead:

• Say "You pay $30 per doctor visit after you've paid $1,500" instead of "20% coinsurance after deductible"
• Use short sentences and active voice
• Put the most important information first
• Use examples and scenarios ("If you visit the ER, here's what you pay")

Lead with What's Changing

Employees care most about what's different. Lead your communications with changes: "Our health plan premiums are staying flat this year. Here's what's new." Then explain what stayed the same.

Personalize When Possible

If your enrollment platform allows, personalize emails and recommendations by family status or role. "Single employees: Here are the plans that fit your needs. Families: Here's what matters most to you."

Send Reminder at Critical Intervals

Don't just announce enrollment once. Send reminders at:

• Enrollment launch
• 1 week remaining
• 3 days remaining
• Last day (sometimes last few hours, depending on policy)

Each reminder can have slightly different messaging to re-engage employees who didn't act on the first message.

Educate, Don't Just Inform

This is the biggest missed opportunity in open enrollment. Most HR teams send a benefits guide PDF and call it done. That's information, not education.

Real education looks like:

Short Explainer Videos (2-3 Minutes)

Walk through key benefits, show real scenarios, and explain what employees need to do. Videos work especially well for visual learners and remote employees.

Comparison Tools

If you offer multiple health plans, provide a side-by-side comparison tool showing premiums, deductibles, and out-of-pocket maximums. Better yet, let employees input their expected usage and see which plan costs them the least.

One-Page Decision Guides

Create focused guides for different employee segments:

• "If you're single and healthy: Choose these plans"
• "If you have a family: Here's what matters"
• "If you have a chronic condition: This plan covers your medications"
• "If you want maximum out-of-pocket savings: This HDHP + HSA combo saves you $2,000/year"

Live Q&A Sessions

Host at least one live session where HR and/or a benefits consultant answer questions in real time. Record it for employees who can't attend live. Allow anonymous questions to encourage participation.

One-on-One Support

For complex situations, make HR available for one-on-one conversations. A 15-minute call can clarify confusion and prevent poor enrollment decisions.

Maximizing Participation in Voluntary Benefits

Many employees skip supplemental benefits during enrollment because they don't understand them or don't see the value. Here's how to drive participation:

Use Real Scenarios

Don't just say "Accident insurance pays for injuries." Instead, tell a story: "Sarah broke her arm in a car accident. Her emergency room visit cost $3,000, and she was out of work for 3 weeks. Our accident insurance paid her $2,500 immediately to help cover expenses while waiting for insurance reimbursement."

Highlight the Pre-Tax Advantage

When offering supplemental benefits through Section 125, emphasize the tax savings. "Accident insurance costs $20/month, but with pre-tax deductions, you actually pay $13/month after tax savings."

Use Opt-Out Rather Than Opt-In (Where Allowed)

If your carrier and legal situation allow, consider automatically enrolling employees in basic supplemental coverage with the option to opt out. Many employees don't opt in by default but keep coverage once enrolled.

Create Decision Guides for Voluntary Benefits

Link to our comprehensive guides: Supplemental Benefits 101. Use it in your communications to help employees understand what's available.

Common Open Enrollment Mistakes

Learning from others' experiences helps you avoid costly missteps:

Enrollment Window Too Short

A 1-week enrollment window isn't enough time for employees to research and make informed decisions. 2-3 weeks is standard and necessary. Plan accordingly.

Information Overload

Sending employees a 50-page benefits guide and expecting them to read it doesn't work. Instead, break information into small, digestible pieces. "Here's the health plan summary. Here's what's new. Here's the cost. Questions?"

No Reminders

Assuming your first announcement is enough is a mistake. Many employees are busy and forget. Reminders—especially a final "last day" reminder—drive participation.

Hard to Reach HR for Questions

If your HR team is too busy to answer questions during enrollment, employees make hasty decisions or don't enroll at all. Block your calendar for Q&A during the enrollment window.

Not Explaining Passive Enrollment vs. Losing Coverage

Employees need to understand what happens if they don't actively enroll. Do they keep their current plans? Do they lose coverage? Are there penalties? Make this crystal clear.

Skipping the Section 125 Update

If you offer pre-tax deductions, your Section 125 plan document must be reviewed and current. Failing to update it annually can cause legal compliance issues.

Post-Enrollment Checklist

Your work isn't done when enrollment closes:

Verify Elections

• Check that all elections processed correctly in your enrollment system
• Confirm no errors or duplicate entries
• Follow up with employees who appear to have dropped coverage unexpectedly

Send Confirmations

• Email each employee a summary of their elections
• Include effective dates and next steps
• Provide contact info for questions

Transmit to Carriers and Payroll

• Send elections to health insurance carriers on time (usually 15 days before plan year start)
• Update payroll system with new deductions
• Request confirmation from all carriers that elections were received

File Required Documents

• Maintain Section 125 plan certification if you made changes to the plan
• Document the open enrollment period dates and process
• Keep records of communications sent

Document Lessons Learned

• What worked well? What didn't?
• What questions came up most frequently?
• How many employees participated and in what plans?
• Note improvements for next year

How Section 125 Fits In

If you offer pre-tax deductions, Section 125 is essential for a successful open enrollment. Here's the basic timeline:

Your Section 125 plan document must be in place and signed before the plan year begins. If you're making changes to the plan (adding benefits, adjusting FSA limits, etc.), the document must be updated.

During open enrollment, employees make elections within the Section 125 plan. They choose which benefits to pay for with pre-tax dollars and establish FSA and HSA contribution amounts.

After enrollment closes, transmit the elections to your payroll provider so deductions begin in the new plan year.

For more on Section 125 setup and administration, see our guide: Section 125 Comprehensive Guide.

Final Thoughts

Open enrollment is your chance to show employees that you care about their wellbeing and have invested in a competitive benefits package. When you communicate clearly, educate effectively, and provide support, enrollment becomes a positive experience instead of a confusing chore.

Start planning early, use multiple communication channels, focus on education over information dumps, and make sure your team is available to support employees during the enrollment window. Your effort pays dividends in employee satisfaction, benefit utilization, and tax savings.