For Benefits Administrators ·
What you'll accomplish
By the end of this guide, you'll have generated the complete set of open enrollment communication materials — announcement email, plan comparison guide, FAQ document, reminder email series, and a "which plan is right for you?" decision guide — using ChatGPT Plus. What normally takes 2–4 weeks of writing and editing gets compressed into a single working session. You'll come out with polished, employee-ready materials in your employer's voice.
What you'll need
What you should see: A chat interface with GPT-4o selected in the model dropdown at the top center of the screen.
Begin by giving ChatGPT the full context in one message — this is the "briefing" that everything else builds from:
I'm a benefits administrator preparing our open enrollment communications. Here are the details:
Company: [Company Name]
Open Enrollment: [Start date] through [End date]
Coverage effective: [Coverage start date]
Enrollment portal: [URL]
HR contact: [Name, email, phone]
Plans offered (with key details):
[Plan 1 name]: $[EE only premium]/month, $[deductible] deductible, $[OOP max] OOP max, [HMO/PPO/HDHP]
[Plan 2 name]: $[EE only premium]/month, $[deductible] deductible, $[OOP max] OOP max, [HMO/PPO/HDHP]
[Plan 3 name if applicable]: [details]
Key changes from last year: [list any plan changes, new plans, terminated plans, premium increases]
Tone: [Professional but friendly / Straightforward / Warm and supportive]
I need you to generate a full open enrollment communication package. Confirm you have what you need, then we'll go piece by piece.
What you should see: ChatGPT confirms it has the details and is ready to generate materials.
Ask: "Write the open enrollment announcement email for our employees."
What to expect: A 3-4 paragraph email covering what open enrollment is, what's new this year, the dates, and how to enroll. Review for accuracy and add your HR team's signature block.
Ask: "Now write a 15-question FAQ covering the most common employee questions about our open enrollment."
What to expect: A numbered FAQ addressing questions like "Do I have to do anything if I want to keep my same plan?", "Can I add a dependent?", "What happens if I miss the deadline?", and plan-specific questions based on the details you provided.
Ask: "Write a 'which plan is right for you?' decision guide comparing our plan options, with scenarios for different employee types."
What to expect: A narrative guide with 4-5 employee scenarios (rarely sees a doctor, has a family with kids, has a chronic condition, is expecting major medical expenses) and which plan makes most financial sense for each.
Ask: "Write three reminder emails: one 2 weeks before the deadline, one 1 week before, and one on the final day."
What to expect: Three escalating reminder emails with appropriately increasing urgency — the final day email should clearly state the deadline time and the consequences of missing it.
Download the generated content. Read each piece as an employee would read it. Look for:
Write an open enrollment announcement email for [Company]. Open enrollment runs [dates]. Key new feature this year: [change]. Portal: [URL]. Tone: professional but approachable.
Generate a 12-question FAQ for our open enrollment. Plans: [list]. Key employee concerns typically include: changing plans, adding dependents, and what happens if they miss the deadline.
Write a "which health plan is right for you?" guide comparing [Plan A] vs [Plan B]. Include scenarios for: a healthy 25-year-old, a family with two kids, someone managing a chronic condition, and someone expecting surgery.
Write an open enrollment deadline reminder email for employees who haven't enrolled yet. Deadline: [date]. Portal: [URL]. Urgent but not alarmist tone.
Translate our open enrollment announcement email into Spanish, maintaining the same professional tone and all specific details.