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Don’t Ask AI to Pick Your Health Plan.
Ask It to Do This Instead..
In this guide, AskGwyn will show you how to use AI to prepare yourself or someone you love for health care open enrollment.
Plan changes.
Drug lists.
Pharmacy information.
Medicare notices.
It gets confusing fast, especially if you’re helping someone else (e.g. parents).
This is where you turn to AI.
But NOT to choose a health plan!
IMPORTANT: Use AI as a translator and organizer to understand what you’re reading, keep track of information, and also figure out what questions to ask.
Here’s the simple 3-step process.
Medicare is the example we’ll use, but the same framework helps with other plans.
1. Create one AI chat that keeps you organized.
Start one chat for yourself or the person you’re helping.
Leave out names, Medicare or health plan numbers, full addresses, birthdays and other identifiers.
Use this prompt in any AI chat (tweak to your situation):
Create and maintain a running tracker with five sections: Medications, Current plan basics, Notices and changes, Questions and verified answers, and Next steps.
I’m helping a parent who has Original Medicare and a Part D drug plan, they take three prescriptions and use one pharmacy.
List what we should review before 2027 Open Enrollment. Add it to the tracker. Do not recommend a plan. Flag anything requiring verification through Medicare.gov or the plan. Do not replace verified information with assumptions.
Now you have once place to keep track of what you know and what still needs work.
2. Make AI explain the fine print
When plan documents arrive, remove identifying information and attach it as a photo or PDF to the same chat.
Ask:
Explain this notice at a 4th grade reading level. List only changes stated in the document. Flag anything affecting drug cost or access. Note the page or section for each change. If the notice does not include an answer, write “not found” instead of guessing. Update the tracker.
Still confused?
Keep asking!
For example:
The notice says one of the drugs moved to a different tier. Explain what that means in plain English. Tell me what I need to check to understand what the person would pay.
If the person you’re helping speaks a different language, ask AI to explain it in their language.
Now you know what changed.
Next, find out what needs an answer…
3. Make AI find the questions you didn’t know to ask
Type this prompt:
Based only on the plan documents, our tracker, and verified information, give me 5 questions that still need answers before Open Enrollment. For each, identify the best authoritative source to check.
If you’re unsure say so. Do not recommend or rank plans.
For Medicare that might mean: Medicare.gov, the health plan, a pharmacist, prescriber or SHIP (State Health Insurance Assistance Program).
For other coverage, check with the health plan, employer’s benefits team, or official Marketplace resources.
Verify the answers and bring them back to the chat. Ask AI to update the tracker and show unanswered items.
AI shouldn’t make your healthcare decisions.
Its job is to help you organize information, understand the language and help you ask better questions before you decide.
This is for general educational information only, not plan advice. Verify Medicare coverage information through Medicare.gov, your plan or SHIP.
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Great idea, Sabrina, to make such a practical use case! As someone who works in this industry and sometimes serves as a content manager, it is useful. Some healthcare companies claim they don't use AI (even though everyone does, whether their company knows it or not)... One reason I'm trying to help is to support those who have a policy but don't know how to communicate about it.
This is great advice. Thank you