# Claude Monthly Check-In Prompt

**Source:** [educateio.notion.site](https://educateio.notion.site/Claude-Monthly-Check-In-Prompt-39ecd6100a7b8058b4cacd0fe6cda553) — saved here for personal use.

**How to use:** paste everything below the line into a Claude conversation, roughly monthly.
Answer by voice or free-form rambling — it's built to sort unstructured input.
Paste the *same* prompt each time; it detects on its own whether it has been run before.

**Last run:** _never_
**Next due:** _—_

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## Ground Rules (Claude reads this before doing anything else)

Determine the mode first, before saying anything else. The question is not "do I know anything about this person," it's "has this specific interview been run before." Claude may already have plenty of unrelated context on me (work chats, project files, memory) without this interview ever having been done. Check memory and past conversations specifically for a prior run of this interview (a completed three-section summary, or answers to these numbered questions). Found one: Mode B. Never found one: Mode A. If it's genuinely unclear either way, just ask me directly which one this is before proceeding.

- **One section at a time.** No exceptions. Never put more than one section's questions in a single message. Never preview or list a later section before the current one is fully wrapped up.
- Always open a section with a **count line** (how many questions or prompts are coming), then list everything for that section in one message.
- Always state, every section, every time, even if it was said last month: I don't need to answer one by one or in order, free-form or voice-dictated answers are fine, and anything extra that doesn't map to a specific question is welcome too.
- Always **wait for my reply** before evaluating it. Never assume or invent an answer on my behalf.
- Always run a **gap-check** before advancing. Compare my reply against that section's questions. If something's missing, thin, or ambiguous, ask one short, targeted follow-up round covering only the gaps; never repeat the full question list.
- **Never summarize until all three sections are fully done.** The summary is the last step, not a running recap.
- In Mode B, never ask a question cold if the answer is already known. Reference what's already on file and ask only about what's likely changed, what's new, or what was never answered. Only fall back to the original full question if there's genuinely no prior signal on it.
- Treat everything learned as **durable context**, carried forward to next month's run; this is cumulative, not a fresh slate each time.

**Mode A** — this interview has never been run before: run the full interview, section by section, exactly as listed below.

**Mode B** — this interview has been run at least once before: don't re-ask everything from scratch. For each section, check what's already known and ask only about what's likely changed, what's new, or what was thin or missing last time. Frame it as an update, not a fresh interview. Still go section by section, following the same ground rules.

## Section Pattern (applies to every section, either mode)

1. Open with the count line. Mode A: "Below you'll find 10 questions about your personal life." Mode B: "Here's what I want to check on for your personal life this month."
2. List everything for that section at once.
3. Remind me: answer free-form or by voice, any order, extras welcome.
4. Wait for my reply.
5. Gap-check; ask a short follow-up round only if needed.
6. Once the section is genuinely covered, move to the next one.

**For this specific run: only start Section 1 (Personal Life) for now.** Don't move to Section 2 until Section 1 is fully wrapped up.

Once all three sections are done, summarize everything back to me in plain language, organized under the three headings, so I can correct anything you got wrong. Don't editorialize or add unsolicited advice during the process; just collect, clarify, and reflect back.

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## Section 1: Personal Life

1. Where do you live (city/area, and type of home), and who do you live with?
2. What do you drive: make, model, year, trim or engine variant? Any other major household vehicles or equipment?
3. What's your relationship or family status, and any major shared milestones or dates already on the calendar?
4. Any health conditions, medications, allergies, or dietary restrictions that should quietly shape suggestions?
5. What's your financial posture right now: saving for something specific, generally budget-conscious, or not a constraint?
6. What are your recurring hobbies or interests, and roughly what level are you at?
7. What does a normal week look like time-wise: work hours, commute, when you're actually free?
8. What tech or software do you actually use day to day outside of work?
9. Any other decisions or life events currently in motion I should know the shape of?
10. Anything personal you'd want me to stay strictly factual and neutral on, or conversely, be unusually direct about?

## Section 2: Work and Career

1. Job title, company, industry, and roughly how long in this role?
2. What does your role actually involve day to day: the tasks that eat most of your time?
3. Org structure around you: who you report to, who reports to you, who you work with directly?
4. What tools or platforms are core to how you work?
5. What are your current live projects, and what state is each one in?
6. Hard rules for your work output: banned words, tone requirements, formatting standards, compliance constraints?
7. Career goals over the next year, and over the next five?
8. A recurring bottleneck or frustration in your work right now?
9. How is your performance or success actually measured, and by whom?
10. Anything about your company or industry's unwritten rules, politics, or constraints that would help me interpret your requests correctly?

## Section 3: How You Want to Work With Me

1. Short direct answers or fuller explanations by default?
2. Critical and pushing back on your ideas, or mostly supportive?
3. Default to agreeing with your framing, or challenge it when I think you're wrong?
4. Show reasoning step by step, or just the conclusion?
5. When a request is ambiguous: best guess and run with it, or stop and ask?
6. Formatting preference: bullets, prose, tables, headers?
7. How much should I assume vs. explicitly confirm before larger pieces of work?
8. Proactively flag things you didn't ask about, or stay in my lane?
9. Something an AI assistant has done in the past that really worked for you?
10. Something that's actively annoyed you about working with AI tools before?
11. When you're wrong or I disagree, how do you want me to bring that up?
12. Any difference in how you want me to behave for work vs. personal or creative tasks?

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_Tip: if you've got 10+ minutes, just talk through your whole life story and business context in one go; tangents are fine._