Writing a good AI prompt is a skill anyone can learn — no programming knowledge required. Here is how to ask the right questions and get answers that actually apply to your situation.
A note on AI tools: Public AI tools like Claude, ChatGPT, Copilot, Gemini, DeepSeek, Perplexity, Meta AI, and GROK can help you explore topics quickly. AI can occasionally produce inaccurate or outdated information — responses shouldn't be treated as expert advice. For anything consequential — health, legal matters, finances — consult a licensed professional and cross-check with trusted sources.
In AI, prompting is the process of writing a question or instruction into an AI model — like a chatbot — to get an answer. The AI responds quickly, often in seconds. Common chatbot examples include ChatGPT, Claude, Google Gemini, Microsoft Copilot, Grok AI, and Perplexity AI.
Writing a proper prompt is a skill most anyone can learn. It does not require programming knowledge.
For example, rather than asking a general question about how to enroll in Medicare, you can provide your personal situation and receive a targeted, specific answer. But you need to know what to ask — and what not to share.
The following is an actual Claude chat session from May 2026, showing how a targeted prompt — and a smart follow-up — produced specific, actionable guidance.
You
Claude
Great question — and no, I don't need your Social Security Number, health information, or any other sensitive personal details to help you with Medicare enrollment. I can give you accurate guidance based on just a few general details about your situation.
Here's what would actually be helpful to know:
That's genuinely all I need. With those answers I can walk you through exactly what steps to take, key deadlines to watch out for, and how to avoid late-enrollment penalties.
You
Claude
This is a very important question, and the answer is: No, do not wait for COBRA to terminate.
COBRA ≠ Employer-Sponsored Insurance for Medicare Purposes
Medicare has a specific exception that lets people delay Part B enrollment without penalty — but only if they have active coverage through a current employer. COBRA does not qualify for this exception. It is considered continuation coverage, not active employer coverage.
The Risk of Waiting
Your Timeline
Since you turn 65 in October, your IEP runs from July through January. Since COBRA ends in November, you are still within your IEP — but you should enroll before or during October, not wait for November.
Bottom Line
Enroll in Medicare during your IEP, and let COBRA either run alongside it briefly or drop it once Medicare kicks in. Many people keep COBRA as secondary coverage for a short overlap, which is perfectly fine.
Medicare Advantage plans are tied to geography. When you move out of state, your coverage doesn't follow you — but important rights do. This example shows how a detailed, specific prompt produces a complete action plan.
The Prompt
You
Claude
1. Will you need to change plans?
Yes. Your Illinois Aetna PPO plan will not follow you to Florida. Medicare Advantage plans are geographically restricted by ZIP code and county. You must act before or shortly after your move.
2. Special Enrollment Period (SEP)
Yes. Moving out of your plan's service area triggers a SEP. Notify Aetna before your move and your SEP starts in July 2026, running through approximately October 31, 2026.
3. Medigap without underwriting — your best window
Yes. This move triggers federal Guaranteed Issue (GI) rights — your right to enroll in a Medigap policy with no health questions, no denial, and no higher premiums. You have 63 days from August 20, giving you a deadline of October 22, 2026. Florida has no birthday rule, so this move window may be your only opportunity.
Your three options
Action Timeline
How to get accurate, useful answers from Claude when handling complex Medicare questions.
Every strong Claude prompt for Medicare work has these four parts. The more you include, the better the answer.
| 1. ROLE | Tell Claude who it's helping — e.g. "You are helping a Medicare counselor who needs accurate, cited guidance" |
| 2. CONTEXT | Give the specific situation — beneficiary's plan type, age, health status, what happened |
| 3. QUESTION | Be specific, not vague — include the exact service, the setting, and what you need to know |
| 4. FORMAT | Tell Claude how to respond — e.g. "Explain in plain language, then give the technical CMS rule" |
Copy and customize the template for your situation. Replace all text in [BRACKETS] with specifics.
Use when a beneficiary asks whether Medicare covers a specific service, item, or procedure.
You are assisting a Medicare counselor. Answer accurately and flag any areas of uncertainty. A beneficiary has [Original Medicare / Medicare Advantage plan: NAME]. They are asking whether Medicare covers [SERVICE/ITEM/PROCEDURE]. Their situation: [relevant clinical details, e.g. "physician ordered it following a diagnosis of X"]. Please answer: 1. Does Medicare cover this? Under which part (A, B, C, or D)? 2. What conditions or criteria must be met for coverage? 3. What would the beneficiary likely owe out of pocket? 4. Is there a relevant LCD, NCD, or CMS policy I should reference? 5. Flag anything I should verify directly with CMS or the plan.
When coverage depends on the setting or classification of care.
A Medicare beneficiary received [SERVICE] in [SETTING: hospital/SNF/home/outpatient]. They want to know which part of Medicare applies and what their cost-sharing will be. Explain: 1. Whether this falls under Part A or Part B (and why) 2. The relevant deductible and coinsurance amounts for 2026 3. Whether a Medigap or Medicare Advantage plan would change the cost 4. Any common billing errors or disputes associated with this service
When you need to explain a complex Medicare concept in simple terms.
I need to explain [COMPLEX TOPIC, e.g. "the Medicare donut hole" / "what an MSP is" / "how coordination of benefits works"] to a Medicare beneficiary. They are [age, any relevant context - e.g. "newly eligible, turning 65, somewhat anxious about costs"]. Please write a clear explanation that: - Uses plain language (no jargon, or explains any term used) - Is no longer than 150 words - Ends with the 1-2 most important things they should do or know - Does NOT sound like a legal disclaimer
Helping a beneficiary choose between Original Medicare and Medicare Advantage, or decide on Part D.
A beneficiary is deciding between Original Medicare + Medigap vs. Medicare Advantage. Their situation: - Age: [AGE] - Health status: [e.g. "manages diabetes and sees 3 specialists regularly"] - Medications: [list key drugs or say "unknown"] - Budget priority: [e.g. "wants predictable costs" / "wants lowest premium"] - Travel: [e.g. "travels frequently" / "stays local"] Please: 1. Summarize the key tradeoffs relevant to THIS person's situation 2. List 3 questions they should ask before choosing a Medicare Advantage plan 3. Note any enrollment period deadlines they need to be aware of 4. Flag anything I should verify with the specific plans available in their area
When a claim has been denied and you need to understand the appeal options and grounds.
A Medicare beneficiary received a denial for [SERVICE/CLAIM]. The stated reason for denial was: "[PASTE DENIAL REASON]" They have [Original Medicare / Medicare Advantage / Part D]. Please explain: 1. What level of appeal applies here (Redetermination / Reconsideration / ALJ / etc.) 2. The deadline to file this appeal 3. What documentation or evidence would strengthen the appeal 4. Whether a physician's letter of medical necessity would help, and what it should say 5. Whether an Immediate Appeal / expedited review applies in this situation 6. The specific CMS or plan process they must follow
When you paste in a Medicare manual section, LCD, transmittal, or EOB and need Claude to interpret it.
Below is [a section of the Medicare Benefit Policy Manual / an LCD / a CMS transmittal / an EOB]. Read it carefully, then answer the following: QUESTION: [your specific question about the document] If the document does not clearly answer my question, tell me exactly what it says and what additional source I should consult. Do not infer or guess beyond what the text states. --- DOCUMENT START --- [PASTE DOCUMENT TEXT HERE] --- DOCUMENT END ---
Important Reminder
Claude is a research and reasoning assistant, not a final authority on Medicare policy. Always verify coverage determinations, appeal deadlines, and benefit amounts against CMS.gov, the Medicare Benefit Policy Manual, or by contacting the plan or Medicare directly. Never paste a beneficiary's Medicare ID, SSN, name, or other PHI into any AI tool.
AI is a great starting point — but for decisions that affect your coverage and your wallet, a real conversation with a knowledgeable person matters. Jim Sullivan offers plain-language guidance with no sales pressure.
(800) 820-9232 Ext. 2800Call between 9 am and 5 pm CST