Open Enrollment (OE) is one of the most important and pressure-filled periods for HR teams each year. Whether you're part of a large organization or managing benefits solo, success comes down to one thing: preparation. A smooth open enrollment process starts months in advance, and the steps you take now will shape how confident and supported your employees feel when it's time to choose their benefits.

This timeline breaks the open enrollment season into three practical phases which are prep, process, and post open enrollment— with clear actions and reminders for each stage. Whether it’s your first OE season or your fifteenth, this guide can help reduce stress, minimize confusion, and give you room to breathe. We've also created a interactive open enrollment survival guide that includes additional step-by-step checklists to help you to plan your easiest open enrollment yet.

Prep Phase: What to Do Before Open Enrollment Starts

Think of this phase as your foundation. The more organized and strategic you are early on, the fewer fire drills you'll face later. From collecting data to finalizing benefits and communicating early, your work here sets the tone for everything that follows.

60+ Days Before: Get Organized and Start Gathering Information

At this stage, your main goal is to collect the internal data and paperwork your broker or benefits platform needs to provide plan quotes and funding options. You’re laying the groundwork so the decision-making process can move forward without unnecessary delays.

• Confirm key open enrollment dates, deadlines, and broker/carrier timelines

• Gather current employee demographic data and dependents

• Ask your broker what documentation they need to run market quotes

• If using alternate funding strategies, clarify whether medical questionnaires are still required for 2025

• Coordinate with Finance or Operations to align on budget guardrails and cost modeling

Getting this info early prevents bottlenecks when it’s time to finalize benefits — and gives you more time to review quotes and options with a clear head.

45–30 Days Before: Finalize Plans and Draft Your Communication Strategy

Once you've reviewed your plan options and funding levels with your broker, it's time to lock things in. Then, shift your focus to the messaging and materials employees will receive. This is where a lot of stress can build — especially if you’re juggling multiple stakeholders — so frontload the creative and planning work now.

• Choose final plans, contribution strategies, and any new benefit additions

• Draft and review OE communications for tone, clarity, and compliance

• Create your high-level comms calendar (emails, town halls, reminders)

• Pull or request updated SBCs, plan summaries, and FAQs from your broker or carriers

• Loop in legal or compliance reviewers early if needed

The sooner your messages and materials are mapped out, the more time you’ll have for feedback and adjustments. This also helps you stay proactive if new questions or plan changes pop up.

30 Days Before: Launch the First Wave of Employee Communication

Employee communication should start early — and go beyond a single email. People are busy, overwhelmed, and likely to skim. Your goal now is to raise awareness, build trust, and clearly explain what employees need to do and by when.

• Send a kickoff message announcing OE dates and high-level changes

• Invite employees to any upcoming Q&A sessions, benefit fairs, or webinars

• Highlight any new plans or perks that may generate questions

• Remind employees what happens if they take no action

• Post information in all the places your employees check: email, Slack, intranet, text reminders

This first touchpoint doesn’t need to answer everything — it just needs to be visible, clear, and reassuring. Let employees know support is coming and give them a reason to pay attention.

15–7 Days Before: Send Final Packets and Prep Internal Teams

As open enrollment nears, shift into execution mode. Make sure employees have everything they need to make confident decisions — and that your internal team knows how to handle questions, submissions, or tech hiccups.

• Distribute final OE packets (digital or print) with plan overviews, costs, and comparison info

• Include a checklist of what each employee needs to submit (and when)

• Add affirmation forms for employees staying on the same plan

• Ensure team members are briefed on FAQs and escalation paths

• Test any online enrollment platforms to catch login or usability issues

Taking the time to equip both your employees and internal teams now can save you hours of troubleshooting and last-minute chaos during the enrollment window.

Process Phase: During Open Enrollment

You’ve done the prep. Now it’s time to launch. This phase is about supporting employees as they make choices — and staying organized so no one falls through the cracks.

Week 1: Monitor, Support, and Answer Questions

Expect questions, confusion, and last-minute realizations. Your job now is to stay calm, keep the information flowing, and make sure every employee knows how to get help.

• Monitor email or help desk channels for incoming questions

• Offer office hours or live Q&A sessions (with broker support if possible)

• Track participation rates to identify who hasn’t started yet

• Confirm that online tools or forms are working correctly and capturing data as expected

• Encourage employees to submit elections early (especially if switching plans)

This is where preparation pays off — instead of putting out fires, you can focus on delivering helpful, human support that keeps things moving.

Week 2: Remind, Re-engage, and Close the Loop

In the second week of OE, shift to follow-ups. Many employees delay making decisions until the last minute, so proactive reminders now can significantly boost completion rates.

• Send gentle nudges to anyone who hasn’t submitted forms or logged in

• Post deadline reminders via internal channels (Slack, Teams, company newsletter)

• Re-share the benefits summary or FAQ one-pager to simplify the decision process

• Clarify the default outcome if no action is taken (e.g., waived coverage, auto-enroll, etc.)

• Confirm how employees will receive confirmation of their elections

Your goal is to help employees complete their elections with confidence — not panic. A few well-timed reminders can make all the difference.

Final 2–3 Days of Open Enrollment: Last Call and Rapid Response

As the deadline approaches, urgency ramps up — and so does the volume of questions and last-minute changes. This is your final push to make sure no one misses their chance to enroll, and to confirm that everything submitted is complete and accurate.

• Send a “final reminder” message with the deadline, what’s at stake, and how to get help

• Keep your inbox monitored closely for urgent employee issues or corrections

• Be prepared to manually assist anyone having trouble logging in or completing their election

• Coordinate with your broker or vendor to confirm when systems will close and data will lock

• Run a quick check to ensure all employees submitted something (even if it’s an affirmation)

These final hours can feel hectic, but staying calm and responsive helps employees feel supported — and reduces errors you'll need to fix later.

Post Open Enrollment Phase

Once the window closes, your job isn’t done — but the pressure starts to ease. Now’s your chance to tie up loose ends and set yourself up for a smoother year ahead.

1–3 Days After: Verify Elections and Send to Broker/Carrier

Act quickly to review employee submissions while the process is still fresh. Small errors now can create big headaches later — especially if they affect coverage or payroll.

• Cross-check submissions against internal records

• Flag and correct duplicate or incomplete forms

• Send verified elections to broker or carrier for processing

• Confirm timeline for ID card generation and plan activation

Getting this step right helps ensure there are no coverage gaps and builds trust with employees going into the new plan year.

1–2 Weeks After: Communicate What Happens Next

Just because OE is over doesn’t mean employees feel done. They may still have questions about next steps — and it’s your job to proactively address those before they start flooding your inbox.

• Let employees know when ID cards will arrive (or how to access them digitally)

• Share how to confirm elections in the benefits portal or via pay stub

• Provide a support contact for post-enrollment questions

• Confirm dates when new payroll deductions (HSA/FSA, premiums) will begin

Taking the lead here shows employees that your HR team is organized, responsive, and still there for them — even after the deadline has passed.

Within 30 Days: Review, Document, and Debrief

Now that the dust has settled, take the opportunity to reflect. What worked? What didn’t? What feedback did you hear from employees or managers? Capturing those insights now will make your life easier next year.

• Host a short debrief with your HR team, broker, or vendors

• Send a quick pulse survey to employees asking for feedback

• Document any issues with forms, tech, timelines, or communications

• Update your internal OE playbook or checklist based on this year’s learnings

Don’t skip this step — even a few notes can help you build a stronger, smoother enrollment process next time.

Continue Benefits Education Year-Round

The best OE strategies don’t end with plan selections. By continuing to educate and engage employees throughout the year, you help them get the most value from their benefits — and reduce confusion during next year’s enrollment.

• Schedule monthly or quarterly “Did You Know?” benefits tips

• Highlight underutilized offerings like mental health resources, HSAs, or wellness programs

• Add benefits reminders to company all-hands or manager meetings

• Monitor questions or confusion trends to improve future comms

A little year-round support goes a long way. When employees feel informed, they’re more likely to appreciate — and use — the benefits you’ve worked so hard to provide.

Final Thoughts

Open enrollment doesn't have to feel like a scramble. With the right timeline, clear communication, and strong internal processes, HR teams can reduce stress for themselves and deliver a better experience for employees.

At Lively, we help employers and brokers streamline benefits year-round — from flexible HSA management to expert support during OE season. If you're ready to level up your benefits experience, contact our team today to learn more.

Disclaimer: the content presented in this article are for informational purposes only, and is not, and must not be considered tax, investment, legal, accounting or financial planning advice, nor a recommendation as to a specific course of action. Investors should consult all available information, including fund prospectuses, and consult with appropriate tax, investment, accounting, legal, and accounting professionals, as appropriate, before making any investment or utilizing any financial planning strategy.