Open enrollment is the annual window when your employees can make changes to their health insurance and benefits elections. For businesses in North Dakota and Minnesota running group health plans, it's also the time when you're making decisions about plan design, contributions, and carrier relationships that will affect your costs and your employees' experience for the next twelve months. When it's managed well, open enrollment is a two-to-three week administrative process that goes smoothly and keeps employees informed. When it's managed poorly, it creates confusion, missed enrollments, compliance issues, and frustrated employees who don't understand their coverage.
This checklist walks through what needs to happen — and when — to run open enrollment correctly.
60–90 Days Before Your Plan Anniversary
The groundwork for a smooth open enrollment happens well before the enrollment window opens. If your plan renews January 1, you should start this process by October 1.
Review your current plan's performance: Pull your claims utilization reports if available (level-funded and self-insured plans provide this; fully insured plans may provide summary data). How did your group use the plan? Are employees hitting high out-of-pocket costs that suggest the deductible is too high? Are there unutilized benefits you're paying for?
Evaluate your current carrier: Has the carrier's service been responsive? How did claims disputes get resolved? Are your employees' preferred providers still in-network? This is the time to assess whether you're getting what you paid for.
Get competing proposals: Your advisor should be shopping your group to multiple carriers 60–90 days before renewal. Waiting until 30 days out limits your options — some carriers take 2–3 weeks to produce a formal proposal, and you need time to evaluate before making a decision.
Decide on contribution strategy: Are you maintaining the same employer/employee contribution split as last year? Absorbing some or all of the renewal increase? Shifting cost to a different plan design? These decisions affect your budget and your employees' costs simultaneously, and they should be made deliberately — not by default.
Decide on plan design changes: If you're switching from a PPO to an HDHP, adding a second plan option, or changing your deductible structure, this is when you make and document that decision. Changes to plan design require more communication preparation than simple rate renewals.
Update your employee census: Verify that all eligible employees are on the list, confirm addresses and dependent information for anyone currently enrolled, and identify any employees who've had qualifying life events (marriage, birth of a child, change in hours) that may affect their eligibility status.
30 Days Before Enrollment Opens
Prepare employee communications: Write a summary of what's changing, what's staying the same, and what employees need to do during enrollment. If premiums are increasing, explain it plainly — employees who understand why something changed accept it better than employees who find out when their paycheck decreases. Be specific: "Your monthly premium will increase from $180 to $210 starting January 1" is far more useful than "some plan changes are coming."
Schedule enrollment meetings: A group meeting where you walk employees through the plan options is worth the time. Employees who don't understand their options often don't make a decision — which creates administrative problems when they come to you in February wanting to add coverage they missed. A 45-minute group meeting followed by an open door for individual questions resolves most of this.
Prepare comparison materials: If you're offering more than one plan option, employees need a side-by-side summary that helps them understand the trade-offs. Don't assume employees know what a deductible or out-of-pocket maximum is. Brief, plain-language explanations of the key differences are more useful than the full plan documents.
Update your benefits administration system: If you use an online enrollment platform (Ease, BenefitPoint, Employee Navigator, or similar), confirm the new plan information is loaded and the enrollment window is configured correctly before you tell employees to go online and make elections.
Prepare waiver documentation: Employees who are waiving coverage (because they're on a spouse's plan, for example) need to submit a waiver form. Have this ready — carriers require documented waivers, and participation calculations require tracking who waived and why.
During the Enrollment Period
Open enrollment for 2–3 weeks: This is the standard window for small group enrollment. Two weeks is the minimum; three weeks gives employees enough time to review options without dragging the process out too long.
Collect all elections and waivers: Every eligible employee should either enroll or document a waiver. Employees who don't respond create administrative problems — most carriers require you to account for all eligible employees.
Handle life event enrollments separately: If an employee is experiencing a qualifying life event mid-enrollment (marriage, birth), coordinate their mid-year changes alongside the open enrollment process rather than conflating the two.
Answer employee questions individually: After the group meeting, some employees will have questions specific to their situation. Keep an open-door or scheduled appointment approach during the enrollment window. Questions you don't answer now become calls to your carrier's member services line and complaints about coverage later.
Submit elections to the carrier: Most carriers have a submission deadline for open enrollment — often 10–15 days before the effective date. Know this deadline and don't miss it.
Post-Enrollment Tasks
Set up payroll deductions: Employee premium contributions need to be configured in your payroll system before the effective date. Verify the correct amounts are set up for each employee based on their elections (single vs. family, plan selected if multiple options were offered).
Distribute insurance cards and ID information: New plan year means new insurance cards for most carriers. Make sure employees know when to expect them and what to do if they need care before cards arrive (hint: they can usually get the group number from their carrier's website or your HR contact).
Confirm effective dates and who's enrolled: Within two weeks of the new plan year starting, verify with the carrier that everyone who should be enrolled is showing in the system. Enrollment discrepancies are much easier to fix in January than in March when a claim is already in process.
Document the process for next year: What worked, what created friction, what employees asked about most often. This information makes the next open enrollment faster and smoother.
What Your Advisor Handles vs. What You Handle
A good benefits advisor handles the carrier shopping, the proposal comparison, the submission of elections to carriers, and the coordination of administrative deadlines — taking most of the external-facing work off your plate. What you own as the employer: communicating to your employees, collecting elections from your team, setting up payroll deductions, and running the internal enrollment meetings.
The clearest division of responsibility prevents things from falling through the cracks because each party assumed the other was handling it. At the start of every open enrollment season, confirm explicitly with your advisor who's doing what.
To get ahead of your next open enrollment, visit /employee-benefits or schedule a conversation with Kain Carlson to start the process early.
Kain Carlson is an independent insurance advisor based in Fargo, ND, licensed in North Dakota and Minnesota. He works with owner-operated businesses across all three coverage pillars — commercial, benefits, and personal — under one advisory relationship. Schedule a review to see where your coverage stands.