If you're the only HR person at your company, you shouldn't be running open enrollment by yourself. Over the 90 days before your plan renews, most of the heavy lifting belongs to your broker: reviewing the renewal, pulling claims data, shopping carriers, building the portal and guide, and sitting with employees one-on-one. Your job is to make decisions on time, get the right people in the room and keep employees informed.
Many solo HR pros never get that split spelled out. They get a renewal packet and a deadline, and end up filling out paper forms and presenting plans alone.
This checklist walks through each stage of the 90 days and shows what's yours, what's your broker's, and where things usually slip. For the full stage-by-stage timeline, see our post on when to start open enrollment planning.
The Checklist: What's Yours and What's Your Broker's
| When | What You Do | What Your Broker Should Do |
|---|---|---|
| 90 days out | Confirm the effective date. Line up who has to sign off (owner, CEO, CFO) and book a quote review. Push employees to return medical questionnaires. | Review the renewal (is the carrier renewing, and by how much?). Request tier 1 and tier 2 claims data, pull an updated census, and send out medical questionnaires. |
| 75 days out | Flag anything employees love or hate about the current plan. | Shop several carriers and products. Bring back proposals that compare current vs. proposed cost and plans. |
| 60 days out | Make the decision, with sign-offs collected. | Walk you through the options, run a disruption report, and finalize contribution strategy and plan design. |
| 45 days out | Book the meeting room and dates. Review the announcement. | Build the enrollment portal, the benefits guide (paper and PDF) and the employee communications. |
| 30 days out | Get employees to the meeting. Send the announcement. | Run the group session and the one-on-ones. Chase non-responders and collect waiver reasons. |
| By the 15th of the month before coverage | Make sure late enrollees are done. | Submit all enrollments and paperwork to the carrier. |
| After enrollment | Pass deductions to payroll. Point employees to the broker. | Email temporary ID cards, calculate payroll deductions, fix errors in the first 30 days, and handle questions all year. |
If most of the right-hand column is landing on you, that's the gap.
Why Does Open Enrollment Prep Take 90 days?
Because most of the work happens before employees see anything. Before anyone opens a benefits guide, someone has to review the renewal, get claims data, collect medical questionnaires, shop carriers, pick a plan, build materials and set up the enrollment platform. Each of those steps waits on someone else.
"That 90-day window starts to go really fast," says Chris McIlroy of McIlroy Insurance Group. Medical questionnaires can take a week. Shopping for quotes can take another week. And open enrollment for most groups lands in the fourth quarter, when carriers and brokers are at their busiest.
"Your one-week turnarounds can become two-week turnarounds," Chris says. Add a CEO and a CFO who both need to sign off, and a few days of waiting on answers turns into a few weeks.
What Starting Late Actually Costs
When the timeline slips, you don't just get a stressful December. You lose options.
You run out of time to shop. "We've run out of options to shop for quotes," Chris says of late-starting groups. "We end up just renewing as-is." That means accepting the incumbent carrier's number, whatever it is.
Enrollment happens after the effective date. If decisions aren't made in time, the plan renews automatically and enrollment happens after coverage has already started. Every change after that is retroactive.
Payroll deductions fall behind. Retro changes mean deductions start late and have to be caught up, which is a hard conversation to have with employees in January.
ID cards are late. Enrollment paperwork is due to the carrier by the 15th of the month before coverage starts, and installing the group takes 1–2 weeks. Enroll against the deadline, and employees start the new plan year without them.
None of these are rare. They're what happens when a 90-day process gets squeezed into 30.
Days 90–60: What Should Happen Before You See Any Quotes?
This is the window where most of the real work happens, and where most brokers go quiet. Here's what it should include.
Review the renewal
The renewal usually arrives right around the 90-day mark. A good broker looks at two things first.
Is the carrier renewing you at all? Chris has seen carriers choose not to renew a group. If that's coming, you want to know at day 90, not day 45.
How big is the change? Did the rate go up a little, a lot, or even down? The number alone doesn't tell you much. What matters is why it moved, which is where claims data comes in.Pull your claims data
At the same time, your broker should request your claims data and pull an updated census. There are two kinds:
• Tier 1 claims are everyday claims: office visits, prescriptions, routine care.
• Tier 2 claims are large claims: a surgery, a cancer diagnosis, a long hospital stay.
Together they show how much the carrier collected in premiums against how much it paid out. "If the company spent the same as they brought in, then they're losing money," Chris explains, because the carrier still has administrative costs. A group whose premiums comfortably exceed claims usually gets a low renewal. Chris has even seen rates go down. A group whose claims exceed premiums can expect a steep increase or a non-renewal.Decide whether to shop the market
Claims data decides what's possible next. A healthy group has leverage: carriers want it, and shopping can bring real savings. A group with heavy claims may find some carriers decline to quote at all, which limits the options.
This is also the question Chris wishes more clients asked during this window: why did the renewal go up or down, and what does our claims data mean for what we can shop?Collect medical questionnaires and request quotes
If you're shopping, many carriers now ask for individual medical questionnaires. Every employee fills one out with height, weight, medications, and medical history, and it goes to underwriting.
It's extra paperwork, but it's worth it. "It's allowing us to shop a lot more carriers," Chris says. "And if that group is healthy, it's going to allow us to get a lot more competitive and lower rates."
Budget a week for questionnaires and another week for quotes. In Q4, budget two of each.
Compare proposals at 75 days out
Once the renewal, claims data, and census go out, proposals start coming back around 75 days out. A broker who really shops the market should bring back several carriers, such as Blue Cross Blue Shield, UnitedHealthcare, Aetna, and Cigna, and more than one product within some of them: fully insured, level funded, and specialty plans.
A good proposal puts your current plan and cost next to each option, shows the year-over-year difference, and gives enough plan detail to compare like for like. If you're only seeing one or two quotes, you're not seeing the full picture.
Days 60–30: How Fast Should You Choose a Plan?
Fast. The decision should be made by the 60-day mark, ideally within days of seeing the quotes. Chris's goal is a decision "within a few days to a week."
That speed only works if the decision-makers are lined up in advance. If your CEO, CFO or owner needs to weigh in, put the quote review on their calendar during the 90–60 window, before the quotes even arrive. Chasing three people for a yes is one of the most common ways a week turns into three.
Check the disruption before you switch
Price isn't the only factor. Are employees happy with the current plan? Is anyone in ongoing treatment where a carrier change could interrupt their care?
MIG runs disruption reports that show how many of your employees' current doctors and hospitals are in the new carrier's network. You might switch carriers and barely disrupt anyone. Or 40% of your employees' doctors might be out of network. Knowing which before you decide matters.
Lock plan designs and rates
Once the plan is chosen, confirm the final plan designs, rates and employer contribution. Every downstream piece depends on these numbers: the benefits guide, the enrollment platform, payroll deductions and your employee announcement. Changing them later means rebuilding all of it.
Build the materials and the platform
The build starts around 45 days out. By 30 days out, everything employees will touch should be ready:
The benefits guide (paper and PDF), covering each plan, costs per paycheck, and how to find a doctor
The enrollment platform or portal, built and programmed with the new plans
Your announcement and communication plan: what's changing, what it costs employees, and where to go with questions
Set the enrollment meeting dates
Book the meetings now, while calendars are still open. Chris's strong preference is in person, which we'll get to next. Schedule a group session plus time for one-on-ones, and send the invites before the 30-day mark.
Days 30–0: What Should Enrollment Meetings Look Like?
Open enrollment at the 30-day mark. The window typically stays open 1 to 1.5 weeks, and everything has to reach the carrier by the 15th of the month before coverage starts.
In person first, then one-on-ones
Chris's preferred format has two parts.
A short group session. "I talk to them all for probably 15 to 30 minutes," he says. He walks through the benefits guide and each plan. He also covers how to find a doctor, how to download the carrier app, what to do when you're out of town, how virtual care works, and the questions employees always ask.
Individual conversations. Employees then go back to work and come in one at a time. "We can talk through their personal situation, their personal needs, their personal budget, and help find the plan that's right for them."
That second part is where employees actually make decisions. It's also what a broker should be doing in the room, not handing you a slide deck and leaving you to present it alone.
What about virtual or recorded sessions?
Zoom works, but Chris calls it "a very distant second best." The problem is attention: "A lot of people are just going to be zoned out or playing on their phones."
Where video earns its place is the follow-up. Individual Zoom or phone calls let employees bring a spouse into the conversation, which matters when the household is choosing a plan together.
For employees who can't make the meeting, Chris doesn't send a recording. He schedules a one-on-one instead, by phone or Zoom. "We're going to do phone enrollments," he said in an earlier interview. "Many of them have personal questions," like a surgery planned this year or a specific medication. "We have the ability to look that up, maybe look at pricing, and we can recommend a plan."
Track who hasn't enrolled
Most employees finish the same day as the meeting. The rest filter in over the next week, and a few always need chasing. MIG's enrollment portal shows three groups: finished, logged in but didn't complete, and never logged in. Automated reminders go only to people who haven't finished, followed by emails, calls and texts.
Get waivers and dependent details now
Employees who decline coverage need to give a reason, usually that they're on a spouse's or parent's plan. Keep that waiver on file. Collect dependent details at the same time: names, dates of birth and anything the carrier needs to verify eligibility. Chasing these in January, after coverage has started, is how small gaps become billing problems.
Day 0 and After: Who Handles the Questions Once Coverage Starts?
Once the carrier installs the group, MIG emails temporary PDF ID cards right away. Physical cards follow in the mail and usually arrive around the effective date. Ask employees to download the carrier app and register for its portal, so their ID card and network are always on their phone.
Payroll deductions also need to reach your payroll team before the first payroll run of the new plan year. MIG calculates the pre-tax and post-tax deductions and sends them over, so they're right from day one.
The first few weeks after the effective date are cleanup time. The most common issues are typos in dates of birth, Social Security numbers and dependent names. Sometimes an employee realizes they forgot to add a dependent. Within the first 30 days, most corrections are still possible.
The fixes and the questions shouldn't all land on you. Your broker should handle the fixes and field employee questions with you. At MIG, that work continues all year: adds, drops, terminations, new-hire enrollments and everyday questions. Before day 0, agree on one thing with your broker: when an employee has a question, who do they contact? Put the answer in the benefits guide and on the last slide of the enrollment meeting.
The Timeline Your Broker Should Hand You
A good broker hands you this timeline before you have to ask for it. They pull your claims data before quoting, start the questionnaires early, and show up in the room for enrollment.
If yours hasn't, that's worth noticing before this open enrollment, not after it.
Not sure how your current broker measures up? Score them with our Broker Evaluation Scorecard and see where the gaps are before this open enrollment. [Get the scorecard]
Frequently Asked Questions
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A full-service broker reviews the renewal and claims data, shops multiple carriers, builds the enrollment portal and benefits guide, runs the employee meetings and one-on-ones, submits paperwork to the carrier, and handles corrections and questions afterward. HR's main job is making decisions on time.
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You may run out of time to shop and have to renew as-is. Enrollment can also end up after the effective date, which means retroactive changes and delayed payroll deductions.
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They let underwriters price the group more accurately. That opens up more carriers, and healthy groups often get lower rates as a result.
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Enrollment has to be submitted by the 15th of the month before coverage starts, and the carrier takes 1–2 weeks to install the group. MIG emails temporary PDF cards as soon as the group installs; physical cards usually arrive around the effective date.
