Open Enrollment Checklist for Employers: 12 Steps to a Smooth Process

Open enrollment is one of the most important — and most stressful — times of year for HR teams and business owners. Employees are making decisions that affect their health and financial security for the next 12 months. Employers are managing deadlines, paperwork, and compliance requirements simultaneously.

The good news: with the right preparation, open enrollment doesn't have to be chaotic. Here's a 12-step checklist to help you run a smooth, compliant, and employee-friendly open enrollment.

Step 1: Start Early — 90 Days Out

The biggest mistake employers make is starting too late. Begin your open enrollment preparation at least 90 days before your plan renewal date. This gives you time to:

• Shop the market for better rates
• Evaluate plan design changes
• Prepare employee communications
• Coordinate with your broker and carriers

Step 2: Review Last Year's Claims Data

If your carrier provides claims data (most do for groups of 25+), review it carefully. High utilization in specific areas — mental health, prescriptions, specialist visits — can inform plan design decisions and help you anticipate cost trends.

Step 3: Benchmark Your Benefits

Are your benefits competitive with other employers in your industry and region? Your broker should be able to provide benchmarking data. If your benefits are below market, you may be losing candidates and employees without realizing it.

Step 4: Shop the Market

Don't auto-renew without shopping. Even if you're happy with your current carrier, getting competitive quotes ensures you're getting fair pricing. An independent broker can do this on your behalf at no cost to you.

Step 5: Evaluate Plan Design Changes

Consider whether your current plan design still makes sense. Common adjustments include:

• Adding or removing plan tiers
• Adjusting the employee/employer premium split
• Adding an HSA-eligible HDHP option
• Modifying deductibles or out-of-pocket maximums

Step 6: Prepare Your Employee Communications

Employees make better decisions when they understand their options. Prepare clear, plain-English materials that explain:

• What's changing from last year
• How to compare plan options
• How to use HSA/FSA accounts
• Enrollment deadlines and how to enroll

Step 7: Schedule Employee Meetings

Don't just send an email and hope employees read it. Schedule group meetings (in-person or virtual) to walk through the options, answer questions, and explain any changes. Employees who understand their benefits use them more effectively and appreciate them more.

Step 8: Update Your Eligibility Records

Before enrollment opens, audit your eligibility records. Remove employees who are no longer eligible, add newly eligible employees, and verify dependent information. Errors here create compliance headaches later.

Step 9: Confirm COBRA Notices Are Current

If you've had any qualifying events during the year (terminations, reductions in hours, etc.), confirm that COBRA notices were sent correctly and on time. Open enrollment is a good time to audit your COBRA compliance.

Step 10: Communicate the Enrollment Window Clearly

Employees need to know exactly when enrollment opens, when it closes, and what happens if they miss the deadline (typically, they're locked into their current elections or default to no coverage). Communicate this multiple times through multiple channels.

Step 11: Collect and Submit Elections on Time

Work with your broker and carrier to ensure elections are submitted before the carrier's deadline. Late submissions can result in coverage gaps or administrative penalties.

Step 12: Confirm Coverage and Distribute ID Cards

After enrollment closes, confirm that all elections were processed correctly. Ensure employees receive their new ID cards before the plan year begins — especially if there are plan changes.

Working with an Independent Broker Makes This Easier

A good independent broker doesn't just help you pick a plan — they help you manage the entire open enrollment process. From shopping the market to employee communications to enrollment support, the right broker is a true partner.

If your current broker isn't providing this level of service, it may be time for a second opinion.

Contact Anderson Financial Group to discuss your upcoming open enrollment and how we can help.

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Anderson Financial Group is an independent employee benefits advisor serving businesses nationwide.