Here’s an uncomfortable number to start with: In a 2024 Voya survey, 91% of working Americans agreed that they typically select the same health plan as the prior year¹. Not because it’s the best fit, but because reviewing the alternatives feels like homework. 

When open enrollment doesn’t go as expected, the problems may surface on day one, but they often start weeks earlier. The plan lineup wasn’t pressure-tested, communications weren’t ready, or nobody decided who would answer the questions employees inevitably have.

That is why preparation matters. We developed this open enrollment checklist to help HR get the plans, systems, communications, and support in place before the enrollment window opens.

 

Open enrollment starts long before employees start enrolling

 

The enrollment window gets most of the attention, but by the time it opens, many of the decisions that shape the employee experience have already been made.

Employees are being asked to compare premiums, deductibles, networks, accounts, and coverage rules, often while trying to predict healthcare needs months into the future. HR’s job is to make that decision easier before employees ever sit down to enroll.

That means reviewing what worked last year, understanding what changed, testing the enrollment experience, preparing the people employees will turn to for help, and anticipating the questions most likely to cause confusion.

Think of day one as the deadline for preparation, not the beginning of it. So, how early should that preparation start? About 90 days out.

Setting your open enrollment timeline

 

Most enrollment stress traces back to compressed timelines. For example, when carrier renewals arrive late, decisions get rushed, and communication becomes an afterthought. 

Working backward from your enrollment start date, a realistic open enrollment timeline looks like this:

 

 

If you’re reading this closer to day one than 90 days out, don’t panic. Most of the items below can be compressed. The order still matters more than the specific calendar dates.

 

1. Audit analytics from the previous year

Before a single email goes out, pull the numbers from last season. In the analytics, search for the story behind the enrollment data rather than noting the stats alone.

We recommend focusing on the following trends:

• Participation rates by plan. If 85% of employees defaulted into the same PPO again, its likely new information hasn’t been fully understood.
• Where people got stuck. Platform drop-off points, the questions that hit HR’s inbox most, the deadline extensions you quietly granted.
• Under-used benefits. This can include an HSA with low contribution rates, an EAP nobody touched, voluntary benefits with single-digit uptake.
• Claims trends. High ER utilization often means people can’t find in-network urgent care. Rising specialty drug spend changes which plans you should spotlight. 

Even one hour with this data will shape better decisions than ten planning meetings without it.

 

2. Finalize the plan lineup and stress-test the changes

 

Your broker may lead renewal negotiations, but HR owns the translation. Once the plan decisions are made, employees need to understand what those changes mean for their healthcare and their wallets.

For every change this year, write down three things: what changed, who it affects, and what employees need to understand before making a decision. That exercise forces plan language into terms employees can actually use when comparing their options.

“We’re moving to a three-tier network” does not tell an employee much on its own. A message saying, “Your plan will now group in-network providers into different tiers. The tier you choose can affect what you pay, so review where your doctors and preferred facilities fall before you enroll,” gives employees a clear action to take.

 

3. Get the compliance housekeeping done early

 

Nothing derails an enrollment week like discovering a missing notice. Confirm these are updated and scheduled for distribution:

• Summary of Benefits and Coverage (SBC) for every plan
• Summary Plan Descriptions and any Summaries of Material Modification
• Required annual notices: CHIP, Women’s Health and Cancer Rights, Medicare Part D creditable coverage, HIPAA special enrollment rights
• ACA affordability check on your lowest-cost plan
• Section 125 plan document updates if you’ve changed contribution structures

Be sure to loop in counsel or your broker’s compliance team as soon as possible, not the week enrollment opens. This is the least glamorous section of the checklist and the most expensive one to skip.

 

4. Test the enrollment platform like an employee, not an admin

 

Every HR team has experienced some version of this: enrollment opens Monday at 9am, and by 9:20 someone’s dependent data is wrong, the new dental plan isn’t showing, or single sign-on fails for the warehouse team that doesn’t have company laptops.

Two weeks before day one, run a full dress rehearsal:

• Enroll a test employee in every plan combination, including waivers
• Verify new hires, rehires, and mid-year status changes display correctly
• Check carrier file feeds both directions, especially for plans you added or dropped
• Confirm payroll deductions map correctly to the new rates

Finally, ask someone who did not build the enrollment experience to test it from start to finish. A fresh set of eyes can catch unclear instructions, confusing steps, and broken links that are easy to miss when you already know how the process is supposed to work.

 

5. Build the communication plan around decisions, not announcements

Unum’s research found that employees spend 30 minutes or less reviewing benefits materials², and around one in five report feeling stressed, confused, or anxious during enrollment. A longer benefits guide is unlikely to solve that problem.

Instead, build your open enrollment communication plan around the questions employees need to answer at each stage:

• The save-the-date (30 days out): Share the enrollment dates, preview major changes, and explain whether employees will need to take action.
• The what-changed message (3 weeks out): Explain what is different this year, who may be affected, and what employees should review before choosing coverage.
• The decision-support push (2 weeks out): Point employees toward plan comparisons, decision-support tools, webinars, office hours, and other resources that can help them evaluate their options.
• The deadline sequence (final week): Send clear reminders as the deadline approaches. Each one should tell employees how much time is left, what action they need to take, and what happens if they miss the window.

Then, think about where those messages need to show up. Email may work for some employees, while Slack or Teams, manager talking points, workplace signage, or text messages may be more effective for others. The goal is not to be everywhere, but rather to ensure important information is visible.

If you would like a more detailed strategy for open enrollment communications, we have outlined a 6 week campaign for you! 

6. Make sure employees have somewhere to take their questions

Even the clearest communication plan will generate questions. Employees will want to know how plans compare, what unfamiliar terms mean, whether their providers are in network, and how different options could fit their healthcare needs.

The problem is that those questions rarely arrive neatly during HR’s office hours. Some employees will ask during a benefits webinar. Others will start comparing plans after work, between meetings, or the night before the deadline.

Before enrollment opens, decide where those questions should go. That could include:

• A searchable benefits hub with plan documents, comparisons, and FAQs
• Office hours or benefits webinars for questions that need a human conversation
• A dedicated HR or benefits support channel with clear response expectations
• Decision-support tools that help employees compare their available plans
• An AI benefits assistant like Healthee’s Zoe that can answer benefits questions and help employees navigate their plan information at any time

The goal is to give employees a clear next step when they get stuck, without making HR the only place they can get an answer. Once those support channels are ready, make sure the other people employees may turn to know where to point them.

7. Brief the people who’ll carry the message

Employees trust their manager more than a benefits portal. A short manager toolkit multiplies your communication for free:

 

• A one-page cheat sheet: dates, top three changes, where to send questions
• Two minutes of talking points for team meetings
• A clear escalation path so managers never guess at answers

 

If you have benefits champions or people leads in each location, brief them the same week. During enrollment, HR should be running the machine, not answering the same question forty times.

 

8. Decide how you’ll measure success before day one

 

Do not wait until enrollment closes to decide whether it went well. Choose the signals you want to track before day one so you know what to watch during the window and what to review afterward.

Start with a few metrics that tell you something useful:

• Active enrollment rate: How many employees reviewed or changed their elections instead of simply defaulting?
• Enrollment completion: How many eligible employees completed enrollment, and where did people drop off or need additional help?
• Employee questions: What did employees ask HR most often? Repeated questions can point to information that was unclear, difficult to find, or missing altogether.
• Decision-support engagement: Which comparison tools, webinars, office hours, or other resources did employees actually use?
• Employee feedback: After enrollment closes, send a short pulse survey asking whether employees understood their options, knew where to get help, and felt prepared to make their elections.

Be sure to capture what you can while the experience is still fresh. Those findings give you a much stronger starting point for next year’s open enrollment than trying to remember what went wrong months later.

 

9. Plan ahead for the week after enrollment.

Enrollment doesn’t end when the portal closes. The week after is where preparation either pays off or unravels, and it deserves its own short checklist:

 

• Reconcile the data. Compare platform elections against carrier confirmations and payroll deductions before the first paycheck of the new plan year.
• Run the exception process. Decide in advance who approves late enrollments and on what grounds, so those calls are consistent instead of case-by-case improvisation.
• Confirm ID cards and effective dates. The first “my new card didn’t come and I have a doctor’s appointment Thursday” message will arrive faster than you think. Know the carrier’s card timeline and publish it.
• Close the loop with employees. A short confirmation summary of what each person elected, sent before January 1, catches mistakes while they can still be fixed.

 

Planning for the week after enrollment gives HR time to resolve outstanding issues, answer follow-up questions, and close out the season before attention shifts to the new plan year.

 

Before you open enrollment: the final checklist

 

By this point, the planning should be done. This final check is about making sure all of that preparation has translated into a working enrollment experience. Before the window opens, confirm that the details are accurate, employees know what to expect and where to get help, and your team is ready to track what happens next.

• Plan changes, rates, and payroll deductions verified
• Enrollment platform tested end to end, including on mobile
• Required notices distributed or scheduled
• Employee communications loaded and scheduled
• Plan comparisons, FAQs, and decision-support resources live
• Employees know what happens if they take no action
• Help channels are ready, with clear owners and response expectations
• Managers and benefits champions know where to direct employee questions
• Success metrics are defined and ready to track
• Post-enrollment follow-up is already on the calendar

If every box is checked, HR can spend less time fixing preventable problems and more time helping employees through the decisions that brought them to open enrollment in the first place.

 

A better open enrollment starts before day one

 

Open enrollment will probably never be the easiest stretch on HR’s calendar. There will still be questions, last-minute decisions, and employees who wait until the deadline is staring them in the face.

But preparation changes what HR has to solve during the enrollment window.

When the plan details have been translated into plain language, the enrollment experience has been tested, communications answer the questions employees actually have, and support is ready when they need it, HR can spend less time reacting to preventable problems.

More importantly, employees get a better chance to understand the benefits they are choosing and how those choices could affect their healthcare and finances for the year ahead.

 

Sources

1. Voya Financial. “Majority of Working Americans Select Same Health Plan from Prior Year during Benefits Open Enrollment, Voya Survey Finds.” https://www.voya.com/news/2024/10/majority-working-americans-select-same-health-plan-prior-year-during-benefits-open

2. HR Dive. “Employees Spend 30 Minutes or Less Reading Open Enrollment Materials.” https://www.hrdive.com/news/employees-spend-30-minutes-or-less-reading-open-enrollment-materials/530224/