Enrollment seasons rarely fall apart on the big things. They fall apart on a broken link, an unbriefed manager, or a segment of the workforce nobody realized was unreachable. This is the list that catches those.
Use it as a working document rather than a formality. The items are grouped by the question they answer, and the ones employers miss most often are flagged as they come up. If you are also building your calendar, pair this with the week-by-week timeline.
1. Reach: can you actually get to everyone?
Start here, because every other decision depends on the answer. This is the section that most often surfaces an uncomfortable surprise.
- Segment the workforce: office, remote, frontline and deskless, shift workers, and dependents.
- For each segment, estimate the share who would see an important message within 48 hours.
- Verify how many employees have a working company email address, and how many actually read it.
- Confirm mobile numbers are current, and that you have documented consent for texting.
- Identify employees on leave, seasonal staff, and anyone hired mid-window.
- Check whether your benefits resource opens without a corporate login. If it does not, a spouse cannot reach it.
- Confirm accessibility: readable on a small screen, works with a screen reader, and available in the languages your workforce speaks.
- Locate the physical places frontline employees congregate — break rooms, time clocks, entrances.
2. Accuracy: is everything locked?
A correction sent mid-campaign costs more credibility than a message sent a week late.
- Final rates confirmed by coverage tier, expressed in per-paycheck dollars.
- Plan design changes documented, including anything being reduced or discontinued.
- Carrier and network changes confirmed, with a way for employees to check whether their doctor is still in network.
- Employer contribution amounts verified, including HSA or FSA funding.
- Enrollment open and close dates and times, with the time zone stated explicitly.
- What happens if an employee takes no action — written in one plain sentence.
- Required notices and compliance materials identified and scheduled.
- Every figure cross-checked against the carrier or broker source, not last year's deck.
3. Content: does it help someone decide?
The test for each piece: name the decision it helps an employee make. If you cannot, it is reference material and belongs in the portal rather than in an inbox.
- A plan comparison organized by employee situation, not by plan name.
- Real per-paycheck costs for every plan and coverage tier.
- The dollar value of the employer contribution stated plainly — employees consistently underestimate it.
- Coverage for dependents explained clearly, including who qualifies.
- The programs beyond medical: telehealth, mental health support, EAP scope, condition management, voluntary benefits.
- Jargon translated: deductible, coinsurance, out-of-pocket maximum, and HSA versus FSA.
- One action per message, with the next step obvious.
- Every message readable on a phone without pinch-zoom, and no attachments required.
4. Channels: is each one doing one job?
- Email assigned to explanation and detail.
- Text reserved for deadlines and action-required messages, with opt-out language included.
- A no-login mobile site serving as the always-available reference layer.
- Teams or Slack used for in-the-flow nudges to desk-based staff.
- Printed material placed where frontline employees actually are, with a QR code and an SMS keyword.
- Sessions offered at times that work for second and third shifts, not only for office hours.
- A recording or asynchronous option for anyone who cannot attend live.
- Reminder sends configured to suppress employees who have already enrolled.
5. Managers: are they equipped or exposed?
Managers get asked first. Left unbriefed, they either guess — which creates work you will have to undo — or stay silent, which wastes your most credible channel.
- Managers briefed before employees receive anything.
- One-page talking points with permitted phrasing for the three most likely questions.
- An explicit escalation line: what to say when they do not know the answer.
- A clear instruction that they should not advise on plan selection.
- A specific ask — mention it in the next two team meetings, confirm everyone on the shift has heard.
- A named HR contact managers can reach quickly.
6. Families: is the actual decision-maker included?
- At least one message designed to be forwarded home.
- Family coverage costs shown for each tier.
- Dependent eligibility rules stated in plain language, including age limits and documentation needed.
- Family-relevant programs highlighted: pediatric care, maternity support, dependent care accounts, mental health for dependents.
- A link that works on any device with no company credentials.
- Spanish or other language versions where your population requires them.
7. Operations: can you handle the response?
- A named human, phone number, and hours published in every action-oriented message.
- Coverage arranged for the final 48 hours, when question volume peaks.
- A shared answer document so your team responds consistently.
- Every link and QR code tested on a personal device, off the corporate network.
- A tracked list of who has and has not completed enrollment, refreshed daily during the window.
- A plan for employees who miss the deadline, and the qualifying-event rules ready to explain.
8. Measurement: will you be able to prove anything?
Decide what you are tracking before the campaign starts. Reconstructing it afterwards is where most measurement efforts die.
- Baseline figures captured from last year: completion timing, active election rate, program participation.
- Reach recorded by workforce segment, not only in aggregate.
- Completion curve tracked daily so you can see whether the early phase worked.
- Active versus default elections counted.
- Questions to HR logged by topic — the top five become next year's content plan.
- Participation measured in the specific programs you promoted.
- A one-page leadership summary drafted in advance, framed in behaviors and dollars rather than opens and clicks.
Consider running one element as a staged rollout — communicate to some locations first and hold others for a few weeks. It gives you a genuine comparison group at no extra cost, which is the cleanest way to attribute a result. The full method is in our guide to measuring communication ROI.
9. After close: do not go quiet
- Confirmation sent to every employee listing what they elected and what it costs.
- Coverage start date and what to expect in the mail clearly stated.
- Two setup actions prompted — register the carrier account, activate the HSA, download the telehealth app.
- A correction window and contact published for anyone who elected something in error.
- New hires and mid-year qualifying events covered by a standing process.
- The year-round calendar scheduled so nothing goes dormant until next fall.
- A short debrief captured while it is fresh: what worked, what broke, what to change.
Key takeaways
- Audit reach by workforce segment first — it determines every other decision.
- Test every link and QR code on a personal phone off the corporate network.
- Lock all rates and plan changes before the first send; mid-campaign corrections cost real trust.
- State the employer contribution in dollars, and the consequence of taking no action.
- Brief managers before employees hear anything, and give them permitted phrasing.
- Send at least one message built to be forwarded to the family.
- Decide your metrics and capture baselines before the campaign starts.
- Use the week after close for confirmations and two concrete setup actions.
Frequently asked questions
What should be on an open enrollment communication checklist?
Nine areas: reach by workforce segment, accuracy of rates and plan changes, decision-focused content, a channel plan where each channel has one job, manager briefing materials, messaging that reaches families, operational readiness for question volume, measurement set up before launch, and post-close confirmation. Reach comes first because it determines everything else.
What do HR teams most often forget during open enrollment?
Four things recur: testing enrollment links on a personal phone off the corporate network, stating the dollar value of the employer contribution, briefing managers before employees hear anything, and sending anything at all after enrollment closes. Each is cheap to fix and each costs a disproportionate amount when skipped.
How do you prepare for open enrollment questions?
Publish a named contact, phone number, and hours in every action-oriented message, staff the final 48 hours when volume peaks, and maintain a shared answer document so responses stay consistent. Log questions by topic as they arrive — the five most frequent are the strongest possible content plan for next year.
What should you measure during open enrollment?
Reach by segment, the completion curve day by day, the share of active versus default elections, question volume and topic, and participation in the programs you specifically promoted. Capture last year's baselines before you launch, because reconstructing a comparison afterwards is where most measurement efforts fail.
Rather not run this alone? We build and manage the whole campaign behind your brand.
Pairs strategic thinking with a drive to get it right every time. With 16+ years of experience — including a communication practice in Sydney, Australia — she specializes in simplifying complex benefit programs.
