08/06/2026
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Itâs Open Enrollment Seasonđ
As the kids head back to school and the leaves start to change color, HR professionals gear up for their favorite time of year, Open Enrollment Season!! Seriously though, itâs the yearâs biggest opportunity to connect with employees and educate them on the value of their benefits. Early planning allows HR to focus less on logistics and more on what energizes us: helping employees navigate complicated information and make informed
choices. We are sharing planning tips and a checklist to avoid the following situations:
Open Enrollment Top Ten Quotes and Questions:
10. I lost my password.
9. Can you tell me which plan to pick?
8. I thought I had until tomorrow.
7. I completed it and forgot to hit Submit.
6. Just one quick question! (30 minutes laterâŚ)
5. I know enrollment ended yesterday, but I need toâŚ.
4. I never got an email. (it was sent 4 times)
3. Do I have to do something?
2. Whatâs an HSA again?
1. WaitâŚthereâs a deadline?!
Priorities
Planning begins with reviewing what worked and what didnât over the past year, employee feedback and of course budget. Schedule time early with your broker and insurance vendors for a plan review and strategies that combine cost, culture and employee needs. You may need to insist on a meeting if vendors say they wonât have data ready. Expectations can be set and strategy can be discussed, and itâs a plus if data is ready sooner with a meeting booked. Pre-plan by confirming timelines with carriers, prepare the system/packets for enrollment, create a communication schedule, draft emails, block time for in person/remote sessions. Focus on employee education about the plans and enrollment deadlines.
Some ideas:
ďˇ Schedule time to meet in person with employees: on off shifts, who are not tech savvy, who work on the floor or in the field â Go To Them.
ďˇ Invite spouses to join remote meetings and encourage emails be forwarded to dependents on the plan.
ďˇ Email is the top communication tool, but paper posted on a bulletin board, a door in their pathway or a bathroom stall/wall are still effective.
ďˇ On time enrollment = raffle entry for company swag or gift cards
ďˇ Have a countdown clock in a common area or on the intranet home page
ďˇ Offer a âbenefits cafĂŠâ with snacks, coffee and time for questions and help with enrollment
ďˇ A benefits fair is a one-stop shop for employees to talk to all vendors, enroll and maybe even get a flu shot plus wellness incentives â get creative! Employees love a 5-minute back massage and free toothbrush.
ďˇ Post QR codes everywhere with a link to enrollment portal, benefit guides, FAQâs, appointment scheduler: bulletin boards, next to or on time clocks, table tents, digital signage, pay stubs, newsletters, screen savers, etc.
ďˇ Equip supervisors and managers with talking points, meeting reminders, slide deck for team meetings and contact info for HR.
No HR professional looks forward to the I forgot to enroll, can you help me call the day after open enrollment closes. HR has many talents, but time travel is not one of them, providing plenty of reminders, resources, and opportunities to enroll helps reduce painful Iâm sorry, the deadline passed conversations.
Hopefully the Open Enrollment Planning Checklist included is a helpful tool:
60-90 Days Before
â Finalize plan design and rates
â Meet with carriers and vendors
â Review employee eligibility and up to date employee data
â Confirm enrollment timeline
â Prepare communication materials and timeline
30 Days Before
â Test enrollment systems
â Distribute benefit guides
â Train HR staff and managers as needed
â Announce open enrollment
During Enrollment
â Send reminders
â Monitor participation
â Answer employee questions
â Resolve issues quickly
After Enrollment
â Audit elections
â Verify payroll deductions
â Submit carrier files
â Evaluate the process for next year
Open enrollment is the busiest time of the year for HR and a great opportunity to connect and educate! It requires organization, communication, patience, and perhaps an extra cup of coffee. With thoughtful planning and a little creativity, you can help employees meet the deadline, navigate their benefit choices, take advantage of a great connection point, and celebrate the many benefits your company offers its valued employees.
Have fun this season!