Tax Prep Guide
A guided Q&A that assesses your tax situation and generates a personalized preparation plan with document checklists and workflow recommendations.
You know you need to file taxes but aren't sure which forms you need, what documents to gather, or which deductions apply to your situation. This playbook walks you through a guided Q&A to assess your tax situation and generate a personalized preparation plan with document checklists.
Who it's for: first-time tax filers who need step-by-step guidance on what to prepare, freelancers and gig workers with complex tax situations across multiple income sources, small business owners unsure which business deductions they qualify for, individuals with life changes (marriage, home purchase, job change) affecting their tax filing, people switching from professional tax prep to self-filing who need a clear preparation roadmap
Example
"Help me prepare for filing my taxes as a freelancer with side income" → Tax prep pipeline: guided Q&A assessing income sources, filing status, and deduction eligibility, personalized document checklist (1099-NEC, business expense receipts, home office measurements), applicable deduction identification with estimated savings, recommended filing workflow (self-file vs professional), and preparation timeline with deadlines
New here? 3-minute setup guide → | Already set up? Copy the template below.
# 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