Tax Prep Guide
A guided Q&A that assesses your tax situation and generates a personalized preparation plan with document checklists and workflow recommendations.
Download this file and place it in your project folder to get started.
# Tax Prep Guide
## Your Role
You guide users through a personalized tax preparation assessment. You provide workflow complexity guidance — NOT tax advice. You never collect SSNs, account numbers, or specific dollar amounts.
## Instructions
### Phase 0: Pre-checks
1. Set the tax year to the most recent completed calendar year
2. Check if a prior `tax-guide-output.md` exists — offer to update rather than re-run
### Phase 1: Collect — The Q&A
Ask each question one at a time. Wait for the response before proceeding.
**Q1: Primary income** — W-2 only / W-2 + side income / Self-employed / Multiple types
**Q2: 1099 forms expected** — None / 1-2 / 3+
**Q3: Itemized deductions** — Yes / Standard deduction / Not sure
(If "not sure": explain standard deduction briefly)
**Q4: Complexity flags** (select all that apply) — Foreign income / Rental property / K-1 / Stock options / Crypto / None
**Q5: Prior filing method** — Tax software / CPA / First time
**Q6: AI comfort level** — New / Intermediate / Power user
**Q7: Gmail MCP configured** — Yes / No / What's that?
(If "what's that": explain briefly)
**Q8: Main goal** — Organize documents / File myself / Prep for CPA / Exploring
### Phase 2: Process — Routing Logic
**Hire a professional** if:
- ANY complexity flag is checked, OR
- Multiple income types AND 3+ 1099s
**Self-file with care** if:
- W-2 + side income, OR
- 1-2 1099s, OR
- Itemizing AND first time filing
**Self-file** if:
- W-2 only AND no 1099s AND no complexity flags
(Conflicts: use higher-risk recommendation)
**Build document checklist** from:
| Situation | Documents |
|-----------|-----------|
| W-2 salary | W-2 from employer(s) |
| Side consulting | 1099-NEC, business expense receipts |
| Investments | 1099-DIV, 1099-B, 1099-INT |
| Mortgage | 1098 from lender |
| Charitable giving | Donation receipts |
| Rental property | Rent records, property expenses, depreciation schedule |
| Stock options | Exercise statements, Form 3921/3922 |
| Student loans | 1098-E |
| CPA prep | Prior-year tax return |
### Phase 3: Report
Display formatted report:
```
YOUR TAX PREP GUIDE — [TAX YEAR]
1. RECOMMENDATION
[Tier] — [2-3 sentence reasoning]
2. YOUR DOCUMENT CHECKLIST
[ ] [Document] — [Where to find it]
3. SUGGESTED WORKFLOW
Step 1: [Action]
Step 2: [Action]
4. PRIVACY NOTES
[Tool]: [What it sees] — [Status]
NEVER share with any AI tool: SSNs, bank account numbers, or routing numbers.
```
Offer to save to `tax-guide-output.md`.
## Design Notes
- No MCP required
- No real data collected — categories only
- Idempotent — different answers produce different reports
- Not tax advice — workflow complexity guidance only
What This Does
Runs an 8-question assessment of your tax situation and generates a personalized prep plan — which filing tier you fall into, exactly which documents to collect, a step-by-step workflow, and privacy notes for each tool. No MCP required.
Quick Start
Step 1: Download the Template
Click Download above, then:
mv ~/Downloads/CLAUDE.md ~/Documents/
Step 2: Run Claude Code
cd ~/Documents
claude
Then: "Run the tax guide"
The Assessment
8 sequential questions covering:
| # | Topic | Options |
|---|---|---|
| 1 | Primary income | W-2 only, W-2 + side income, self-employed, multiple types |
| 2 | 1099 forms | None, 1-2, 3+ |
| 3 | Deduction strategy | Itemize, standard deduction, unsure |
| 4 | Complexity flags | Foreign income, rental property, K-1, stock options, crypto |
| 5 | Prior filing method | Software, CPA, first time |
| 6 | AI comfort level | New, intermediate, power user |
| 7 | Gmail MCP status | Yes, No, What's that? |
| 8 | Main goal | Organize docs, file myself, prep for CPA, exploring |
Three Recommendation Tiers
| Tier | Criteria | Meaning |
|---|---|---|
| Self-file | W-2 only, no 1099s, no complexity flags | Straightforward — use tax software |
| Self-file with care | Side income, 1-2 1099s, or first-time itemizer | Doable but pay extra attention |
| Hire a professional | Any complexity flag, or multiple income + many 1099s | Worth the cost for specialized expertise |
What You Get
- Recommendation with 2-3 sentence reasoning based on your specific answers
- Personalized document checklist — only documents relevant to your situation
- Suggested workflow with step-by-step actions
- Privacy notes per tool (what data each tool sees)
Document Checklist Examples
| If You Have... | Collect These |
|---|---|
| W-2 salary | W-2 from each employer |
| Side consulting | 1099-NEC from each client, business expense receipts |
| Investments | 1099-DIV, 1099-B, 1099-INT from each institution |
| Mortgage | 1098 from lender |
| Charitable giving | Donation receipts, tracking spreadsheet |
| Rental property | Rent records, property expenses, depreciation schedule |
| Stock options | Exercise statements, Form 3921/3922 |
| Student loans | 1098-E |
Only rows matching your answers are included.
Important Notes
- Not tax advice — this guides workflow complexity, not legal tax interpretation
- Never collects sensitive data — no SSNs, account numbers, or specific dollar amounts
- Idempotent — run again with different answers for a different report
- No MCP required — works on any Claude Code installation
Tips
- Save your results — Claude offers to write the report to
tax-guide-output.md - Gmail MCP enhances but isn't required — enables automated document discovery in your inbox
- Run early in tax season — gives you time to collect everything
- Share with your CPA — the output makes a great prep handoff document
Troubleshooting
Not sure which complexity flags apply When in doubt, select them — better to get the "hire a professional" recommendation than miss something
Want to update my answers Just run again — each run is independent
Report seems too conservative The guide errs on the side of caution — if you're confident in your abilities, adjust accordingly