When to use
- You said "what do I need to file my business taxes this year?" or "am I missing anything before I go to my accountant?"
- Tax season is approaching and you want a personalized list instead of a generic "here's what you need" article.
- Your situation changed this year — new entity type, first employee, first contractor, new state, a vehicle or home office added — and you're not sure what that adds to the pile.
- You want the checklist organized by where each document comes from (bank, payroll provider, payment processor, prior accountant) so gathering it is a to-do list, not a maze.
Do not use it to calculate what you owe, to decide how to file, or to interpret tax law for your specific situation — it does not do that. It is a document/data organizer, not a preparer or an advisor.
What it does
Asks a short intake, then returns a checklist grouped by category:
- Intake questions (only what's needed): entity type (sole prop, LLC, S-corp, partnership, other/not sure), state(s) you operate in, whether you have employees, whether you paid contractors, whether anything changed since last year (new entity, new state, vehicle, home office, equipment purchases, a loan, an investor).
- Income documents: bank/merchant statements, 1099s you should expect to receive, invoices, platform payout reports (Stripe, Shopify, PayPal) — named by source, not assumed to exist.
- Expense documents: bank/card statements, mileage log, home-office measurements, receipts for large purchases, payroll reports if you have employees.
- Prior-year references: last year's return, depreciation schedules, carryforward losses — flagged as "ask your accountant for this if you switched preparers."
- Entity-specific items: only the ones that apply to the entity type given (e.g., K-1s for partnerships/S-corps, payroll tax filings if there are employees) — it does not list items for entity types the user doesn't have.
- Open flags: anything the intake couldn't resolve (e.g., "not sure if you're a sole prop or single-member LLC") is listed as a question for the accountant, not guessed.
It never tells the user what they owe, which forms to file, or how to classify a borderline item (worker vs. contractor, deductible vs. not) — those are flagged as "ask your accountant/CPA or check IRS.gov", not answered.
If they pay contractors, the W-9s come first. A business with contractors cannot close its tax prep without a W-9 on file for each one — it is what the 1099-NEC is built from, and chasing a contractor in January is far harder than in June. Always list it explicitly; it is the single most commonly missing document, and its absence is only discovered at the deadline.
How to use
- Answer the intake questions (entity type, state, employees/contractors, what changed this year). If you don't know an answer, say so — the skill will flag it instead of assuming.
- Get the categorized checklist. Check off what you already have.
- Use the "ask your accountant" flags as your actual agenda for the handoff call — they're the parts that need a professional, not a search engine.
- Re-run it if your situation changes mid-year (e.g., you hire your first employee) to see what's newly added.
Best for
Solo founders, freelancers, and small business owners without an in-house finance team who want to walk into tax season (or their accountant's office) with the right pile of documents instead of a guess. Not for anyone who needs an actual tax calculation, a filing decision, or advice on a specific tax position — that always goes to a licensed CPA/EA or a search of IRS.gov, and the skill says so every time it's asked to cross that line.