Open Enrollment Strategy for Mid-Size Employers: How to Help Employees Make Better Benefits Choices in 2026

Most employees spend less than 20 minutes choosing their health plan during open enrollment. That is not a guess. Research from the Employee Benefit Research Institute and Aflac's annual Open Enrollment Report consistently shows that a large share of workers either re-enroll in last year's plan without reading anything new or make a selection based on the monthly payroll deduction alone. For a 50-person company, that pattern quietly costs tens of thousands of dollars each year in adverse selection, underutilized HSA accounts, and mismatched plan choices.

For mid-size employers with 20 to 250 employees, open enrollment is not just an HR checkbox. It is one of the few moments in the year when you have a captive audience and a real opportunity to shift how your team thinks about their coverage. Run it well and you reduce confusion, improve plan participation, and protect your benefits budget. Run it the same way you did three years ago and you are essentially handing enrollment decisions over to inertia.

This guide walks through a practical open enrollment strategy built for mid-size employers. No jargon, no generic HR advice. Just a clear framework for communicating better, reaching more employees, and running an enrollment window that actually produces informed decisions.

Why Employees Make Poor Benefits Choices at Open Enrollment

The Average Enrollment Decision Takes Under 20 Minutes

Aflac's Open Enrollment Report has tracked this for several years. A substantial portion of employees spend fewer than 20 minutes reviewing their options before making a decision. Some spend less than five. For context, that is less time than most people spend deciding where to eat lunch.

The reasons are understandable. Enrollment materials are dense. Plan comparison documents are written by attorneys for compliance, not by communicators for clarity. Employees who are juggling shifts, deadlines, or family responsibilities are not going to read a 14-page Summary of Benefits and Coverage unless something specific motivates them to do so.

The solution is not more documents. It is fewer, better ones, delivered at the right time, in the right format, with a clear call to action.

The Default Bias Problem

Behavioral economists call it status quo bias. HR managers call it "everyone just re-enrolled." Either way, the pattern is the same: when people are uncertain and the stakes feel abstract, they default to whatever they did before.

For employees, re-enrolling in last year's plan feels safe. They know what the co-pay is. They know their doctor is in-network. They do not want to read fine print and risk making it worse. So they click through and move on.

The problem is that their situation may have changed. A new baby, a paid-off mortgage, a spouse who changed jobs and gained separate coverage. Any of these can make last year's plan the wrong plan for this year. But if no one prompts employees to reconsider, they will not reconsider on their own.

Good enrollment communication breaks that default. It gives employees a concrete reason to look at their options again, not just an email saying "enrollment is open."

Why This Costs Employers Money Too

Adverse selection is what happens when your higher-cost employees disproportionately enroll in your richest, most comprehensive plan, while lower-cost employees choose the bare-minimum option. Over time, this drives up claims in your comprehensive plan and distorts your renewal pricing.

HSA underutilization is a separate but related cost. If you offer a high-deductible health plan with an HSA and no one contributes to it, you lose a meaningful tax advantage. The IRS allows employers to contribute to employee HSAs on a pre-tax basis, which reduces payroll taxes for both the company and the employee. According to SHRM research, a majority of employees who are eligible for HSAs either do not contribute or contribute less than the IRS maximum, often because they do not fully understand how the account works.

Both problems are partially addressable through better enrollment communications. Not entirely. But meaningfully.

When to Start Your Open Enrollment Campaign

The 90-Day Runway That Separates Good Enrollments from Scrambles

Most mid-size employers start thinking about enrollment three to four weeks before the window opens. That is enough time to send emails and post a benefits guide, but not enough time to actually change how employees think about their options.

A 90-day runway gives you three things: time to update your materials, time to train your managers, and time to let information sink in before anyone is asked to make a decision. Adults need repeated exposure to new information before it sticks. One well-timed email three weeks out is not repeated exposure.

If your plan year renews January 1, your campaign should start in early October. If it renews July 1, your campaign starts in early April. Whatever the date, mark 90 days prior on your calendar and treat it as the start of the work, not the start of the communications.

The Month-by-Month Communication Calendar

90 to 60 days out (pre-enrollment): This phase is about awareness and education, not action. Employees do not need to do anything yet. Use this window to introduce any plan changes, explain what is staying the same, and begin the HSA or high-deductible education for teams where those options are available. A short video from the owner or HR lead, one page of plain-language highlights, and a posted FAQ are sufficient for most companies at this stage.

60 to 30 days out (countdown phase): This is when you introduce decision-support tools. Share the side-by-side plan comparison. Hold team walkthroughs. Send the employer dollar story message (described in the next section). If you have employees who are likely to need help, schedule individual 15-minute calls with HR or your broker during this window.

During the enrollment window: Three communications work well here: an open message with the enrollment link and deadline, a mid-window reminder with a participation count ("We still need 40 people to complete enrollment"), and a final 48-hour deadline reminder. Each message should have one clear call to action and nothing else.

Post-enrollment: Confirm enrollment to each employee individually. Send a summary of what they enrolled in and what their payroll deductions will be, before those deductions start appearing in their paychecks. Surprises in the paycheck erode trust faster than almost anything else.

Segmenting Your Message by Employee Type

How Salaried and Hourly Employees Evaluate Benefits Differently

Salaried employees at mid-size companies typically have consistent computer access, read their email during work hours, and are comfortable navigating online enrollment platforms. They also tend to have higher household incomes, which means plan design features like deductibles, cost-sharing percentages, and out-of-pocket maximums are legible to them in a way that is not always true for hourly workers.

Hourly employees are thinking about take-home pay first. For someone earning $18 to $22 per hour, a $40 monthly premium increase is a meaningful hit to cash flow. They are also less likely to have a strong mental model of how health coverage actually works, not because they are less intelligent, but because the system is opaque and no one has ever explained it in plain terms.

Your messaging needs to reflect this. The detailed plan comparison document that works for your salaried accounting team will not work for your hourly warehouse or field staff. Consider developing two versions of key materials: one with full detail for employees who want it, and one that leads with a simple monthly cost table and a two-sentence explanation of the key difference between your plan options.

For more on structuring benefits differently across employee segments, see our guide to building a two-tier benefits strategy for mixed workforces.

Reaching Employees Who Do Not Have Regular Computer Access

If 30 percent or more of your workforce does not regularly check email during working hours, your digital-only communication strategy has a structural gap. This is common at companies with manufacturing floors, retail locations, food service operations, or field crews.

A few approaches that work for these teams:

Print a one-page enrollment summary and post it in break rooms, near time clocks, and in any shared physical space where employees gather. Include a QR code that links directly to the enrollment portal.

Schedule a brief group walkthrough during a shift overlap or before a team meeting. Fifteen to 20 minutes with a manager who knows the basics is more effective than sending the same email three times.

Text-based reminders are increasingly effective for hourly teams. If your HR platform supports SMS notifications, use them. Enrollment deadlines do not get lost in a text thread the way they do in a crowded inbox.

Ask direct supervisors to participate. When a frontline manager says "HR needs everyone to complete enrollment this week," employees pay attention in a way they do not when the email comes from a [email protected] address.

The Five Communications That Actually Move Employees to Act

The Employer Dollar Story

Most employees have no idea what their employer pays toward their health coverage. According to the KFF 2024 Employer Health Benefits Survey, the average employer contribution for single coverage was in the range of $7,000 to $8,000 per year, and for family coverage, closer to $15,000 to $16,000 per year. Employees who see only their own payroll deduction often assume their employer is paying much less than that.

The employer dollar story is a simple one-page or one-screen message that shows the full picture: "Here is what you pay. Here is what we pay. Here is your total annual benefit." When employees understand that their employer is contributing $600 to $700 per month toward their health plan, they tend to value their benefits more and make more deliberate enrollment decisions.

This message also helps with retention. It is hard to leave a job when you have a clear picture of the total compensation value you would be walking away from.

The Side-by-Side Plan Comparison

Do not ask employees to compare plan documents. Create a comparison for them. A simple table with four or five rows, showing each plan option side by side, with the following fields: monthly employee cost, annual deductible, out-of-pocket maximum, primary care co-pay, and specialist co-pay.

Then add a "total annual cost" scenario. Assume a low-use year (one or two primary care visits, no major claims) and a high-use year (a hospitalization or surgery). Show what each plan would actually cost the employee in both scenarios. This is more useful than any amount of explanation about how deductibles work, because it connects abstract plan design features to real dollar outcomes.

The goal is not to steer employees toward any particular plan. It is to make the comparison legible so they can make a choice that fits their situation.

The HSA Primer

If you offer a high-deductible health plan option paired with an HSA, your employees need a plain-language explanation of how the HSA works before they can meaningfully evaluate that option. Most of them do not have one.

The key points to communicate: an HSA is a savings account they own and keep permanently, even if they change jobs. Contributions are pre-tax, which means they reduce both income tax and FICA. The money can be invested and grows tax-free. And withdrawals for qualified medical expenses are also tax-free. That is a triple tax advantage no other account offers.

If your company contributes to employee HSAs as part of the plan design, lead with that number. "We put $500 into your HSA on day one" is a more motivating message than any amount of technical explanation about contribution limits.

The Dependent Coverage Reminder

Life changes during the year. Employees get married, have children, get divorced, or watch a dependent age off their plan. Open enrollment is the annual opportunity to update dependent coverage, but many employees do not think to review this unless prompted.

A simple reminder, sent early in the enrollment window, that asks employees to verify their dependent list does two things. It catches errors before they become claims problems, and it prompts employees to re-examine their plan selection in light of their current family situation rather than last year's.

The Deadline Urgency Message

Most enrollment reminders say "enrollment closes Friday." The deadline urgency message says something more specific: "As of today, 23 employees on your team have not yet completed enrollment. If you miss the deadline, you will be auto-enrolled in [specific plan] at [specific cost] and will not be able to make changes until next year."

Specificity creates urgency. Generic reminders get ignored. When employees know exactly what happens if they do nothing, they are more likely to take the five minutes required to make an active choice.

Decision Support Tools That Work for Mid-Size Teams

Free Online Calculators and Comparison Tools

Several free tools are available that let employees enter their expected healthcare usage and see which plan option is likely to cost them less over the course of the year. These are not perfect. They rely on self-reported usage estimates that employees often get wrong. But they shift the frame from "which plan looks cheaper on the surface" to "which plan is likely to cost me less given how I actually use healthcare," which is a meaningful improvement.

Your broker or benefits administrator may have a plan comparison tool built into your enrollment platform. If so, make sure employees know it exists and how to access it. These tools go unused at most companies not because employees do not want them, but because no one told them they were there.

If you have a Section 125 cafeteria plan in place, your enrollment platform should also show employees the pre-tax savings they generate by paying premiums through the plan. That number, often $400 to $800 per year for a single employee, is concrete and motivating in a way that abstract tax language is not.

Enrollment Sessions That Actually Help

A 30-minute team walkthrough, offered two to three times during the enrollment window at different times of day, is one of the highest-leverage investments an HR manager can make. Not a webinar with 200 slides. A focused session that covers three things: what changed this year, how to compare your plan options, and how to complete enrollment before the deadline.

Record the session if possible. A recorded walkthrough that employees can watch at their own pace reaches people who could not attend live, and it reduces the number of individual questions HR has to field one at a time.

If you also offer voluntary benefits like life coverage, disability, or supplemental accident plans, give them their own dedicated five to ten minutes in the walkthrough. Voluntary benefits are frequently the least understood piece of the enrollment package, and employees who do not understand them usually skip them, even when the cost is low and the value is real.

Frequently Asked Questions

When should we start open enrollment communications?

Start 90 days before your enrollment window opens. Use the first 30 days for awareness and education, the second 30 days for decision-support tools and team walkthroughs, and the final 30 days for active enrollment reminders and deadline urgency messages. Companies that start within three weeks of the enrollment window typically see higher rates of default re-enrollment and more post-enrollment confusion about plan selections.

How do we help employees choose between a PPO and a high-deductible plan?

Build a side-by-side cost scenario using real plan numbers. Show the total annual cost for two situations: a low-use year with one or two routine visits, and a high-use year with a significant claim. For most healthy employees under 40 with no chronic conditions and no dependents, a high-deductible plan paired with an HSA will cost less in total, especially when the employer contributes to the HSA. For employees with chronic conditions, regular prescriptions, or young children who use primary care frequently, the PPO often wins on total annual cost despite the higher premium. The goal is to help employees do that math for their own situation, not to steer them.

What is adverse selection and how does open enrollment design affect it?

Adverse selection in employer health plans happens when your sickest, highest-cost employees disproportionately enroll in your richest plan option, while healthy employees opt for a leaner plan or waive coverage altogether. Over time, the claims experience in your comprehensive plan gets worse, which drives up its renewal cost. Good enrollment communications reduce adverse selection by helping all employees make plan choices based on their actual situation, not just defaulting to the most comprehensive option out of caution. Transparent plan comparisons, clear HSA education, and well-structured premium tiers all help flatten the selection curve.

Should we hold in-person benefits meetings if our team is remote or hybrid?

Yes, but adapt the format. A 30-minute live video session with screen sharing accomplishes most of what an in-person meeting does, as long as you record it and make the recording available for at least two weeks after the enrollment window opens. For hybrid teams, consider offering both a live session and a recorded option, and make sure your enrollment platform is fully accessible from personal devices, not just company-issued computers. If a significant portion of your workforce is hourly or field-based and lacks reliable internet access, pair the virtual session with printed materials and a text-based reminder campaign.

How do we explain HSA contributions in plain language?

Lead with the money, not the mechanics. "You put money in before taxes. You use it for medical bills. What you do not use stays in your account and can be invested. It is yours forever, even if you change jobs." That is the plain-language version. From there, add the specific numbers: the IRS contribution limit for the current year, what your company contributes, and the estimated tax savings on a contribution at or near the maximum. Most employees who understand those three things will choose to contribute. Most employees who only hear "pre-tax savings vehicle" will not.

What happens if an employee misses the open enrollment window?

If your plan has a default enrollment rule, the employee gets placed in whatever plan that rule specifies, typically the lowest-cost option or last year's plan. If there is no default rule, they may be left without coverage until the next qualifying life event or the next open enrollment period. Neither outcome is good. The best prevention is the specific deadline urgency message described earlier, sent at least 48 hours before the window closes, with exact language about what happens if no action is taken. Employees who know the consequence of missing the deadline are significantly more likely to act before it passes.

References

1. KFF. 2024 Employer Health Benefits Survey. Kaiser Family Foundation, 2024. https://www.kff.org/health-costs/report/2024-employer-health-benefits-survey/
2. SHRM. Benefits: Open Enrollment Resources and Research. Society for Human Resource Management. https://www.shrm.org/topics-tools/topics/benefits
3. Employee Benefit Research Institute (EBRI). Health Plan Enrollment and Decision-Making Research. EBRI. https://www.ebri.org
4. Aflac. Open Enrollment Report 2024. Aflac Incorporated, 2024.
5. Employee Benefit Research Institute (EBRI). Health Savings Account Balances, Contributions, and Distributions 2023. EBRI Issue Brief, 2024.