If your company's open enrollment period is in the fall, you might think you have months before you need to worry about it. But the businesses that have smooth, successful enrollment seasons aren't the ones that start planning in October. They're the ones that start right now - in June and July.
Open enrollment affects every employee in your company. When it's rushed, participation drops, employees make uninformed decisions, and you lose the competitive advantage that good benefits should provide.
Here's a mid-year planning timeline that sets you up for success.
Assess your current plans. Pull utilization data. Which plans are employees actually using? Which ones are underutilized? Are there any pain points or frequent complaints? If you're working with a broker, schedule a mid-year review meeting.
Benchmark your offerings. What are similar companies in your industry and geography offering? Benefits benchmarking data is available through SHRM, BLS, and many broker platforms. This helps you understand whether your package is competitive.
Survey your employees. Before you renew, ask your team what matters to them. A short, anonymous survey about benefits satisfaction can reveal surprising insights. Maybe nobody uses the gym reimbursement, but everyone wants better dental coverage. Don't guess - ask.
Review compliance requirements. Have any regulations changed since last year? New state mandates, ACA threshold changes, or SECURE 2.0 provisions could affect your plan design or reporting obligations.
Negotiate renewals. Armed with your utilization data and benchmarking research, negotiate with your current carriers or explore alternatives. Switching carriers or plan designs mid-cycle is possible - but only if you start early enough.
Finalize plan options. Decide what you'll offer for the coming year. Consider the balance between premium costs (employer and employee share), deductible and out-of-pocket levels, network coverage, and ancillary benefits like dental, vision, life, and disability.
Build your communication plan. Enrollment materials shouldn't be an afterthought. Create clear, simple resources that explain each plan option, the differences between them, enrollment deadlines, and any changes from the current year. Consider multiple formats - email, one-pagers, FAQs, and a live Q&A session.
Launch the communication campaign. Start at least two to three weeks before the enrollment window opens. Send the first email introducing the upcoming enrollment period and key dates. Follow up with plan comparison materials and decision-support tools.
Host an information session. Give employees a chance to ask questions - either in person or virtually. This is especially important if you're making changes to existing plans. People resist change when they don't understand it.
Open the enrollment window. Most companies keep the window open for two to four weeks. Send reminders at the midpoint and close of the window. Make the enrollment process as simple as possible - ideally through your benefits platform, not paper forms.
Confirm elections. Send each employee a summary of their elections before the new plan year begins. Give them a short window to correct any errors.
Update payroll. Make sure premium deductions are correctly reflected in the first paycheck of the new plan year.
File any required reports. ACA reporting (Forms 1094-C and 1095-C for ALEs) and other compliance filings have specific deadlines. Get these on the calendar now.
When businesses rush open enrollment, employees make poor choices because they didn't have time to understand their options. Participation in valuable programs like HSAs, FSAs, and 401(k) matches drops. Employers miss negotiation opportunities with carriers. And HR teams end up fielding questions and corrections well into January.
Starting early isn't about doing more work. It's about spreading the work out so everything runs smoothly when it counts.
Need Help Planning?
If open enrollment planning feels overwhelming - or if you've never had a structured process - we can help. From benchmarking to employee communication to carrier negotiation, we work with small businesses to make enrollment season a competitive advantage, not a fire drill.
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