Gather 12 months of bank and credit card statements, merchant payout reports, payroll registers, contractor payments (1099s), fixed asset invoices, and prior-year tax returns. Reconcile accounts, close books, and produce supporting schedules to minimize surprises and penalties.
On the go? Listen on The Deep Dive — where we dig deeper into this topic: ‘The Proactive Business Tax Checklist_ How to Organize Documents, Reconcile Gross Sales, and Avoid Double Fees (Gross vs. Net Explained)’. Listen or download.
Why this matters
Good bookkeeping reduces tax-time stress, shortens your CPA’s review, and can lower penalties or missed deductions. Preparing in advance helps you avoid last-minute rushes, identify deductible expenses, and ensures reports match filed returns.
A short story
A landscaper waited until March to assemble files; missing 1099s and unreconciled merchant payouts delayed filing and increased fees from their preparer. With a proactive checklist the following year, they completed reconciliation in mid-January and the CPA filed on time with no surprises. Early prep saved money and reduced stress.
Checklist — Documents to gather
- Bank statements (all business accounts) — Full monthly statements for the tax year.
- Credit card statements (business) — Monthly statements and receipts for disputed charges.
- Merchant processor reports — Stripe, Square, PayPal payout CSVs and settlement reports.
- Payroll registers & tax deposits — Payroll summary, tax deposit receipts, W-2s and W-3s.
- Contractor payments — Total paid per vendor for 1099s; W-9s on file.
- Prior year tax return — Last year’s federal and state returns for reference.
- Fixed asset invoices & dispositions — Purchase invoices, sale/disposal evidence, depreciation schedules.
- Loan & lease interest statements — Form 1098 or lender statements for interest paid.
- Sales tax filings & exemption certificates — Filed returns and reseller certificates.
- Inventory counts & COGS support — If applicable, year-end inventory valuation and purchase invoices.
- Business mileage & auto logs — Mileage logs or expense records for vehicle deductions.
- Receipts for deductible expenses — Advertising, meals (with business purpose), supplies, professional fees.
Reconciliation & cleanup steps
- 1. Reconcile bank and credit card accounts to the last statement date.
- 2. Reconcile merchant payouts to gross sales and fees; adjust deposits as needed.
- 3. Reconcile payroll liabilities and prepare W-2/1099 information.
- 4. Prepare A/R and A/P aging and ensure large outstanding items have support.
- 5. Finalize fixed asset schedule and reconcile accumulated depreciation.
- 6. Review tax account balances (deferred taxes, sales tax payable) and prepare adjusting entries.
- 7. Run a Trial Balance and compare prior year totals to identify large variances.
Common pitfalls that cause delays
- Missing 1099/1098 or W-2 information due to scattered vendor records.
- Unreconciled merchant payouts leading to incorrect revenue and fee reporting.
- Owner personal expenses mixed with business accounts causing audit risk.
- Undocumented expenses or lack of receipts for deductions.
- Incorrect classification of labor (employee vs contractor) affecting payroll filings.
- Failure to account for inventory or COGS properly for product businesses.
Worksheet — Tax season upload index
Use this table to collect files and provide links to your CPA or bookkeeper. Paste into a spreadsheet or print it.
| Document | File Location / Link | Date Range | Uploaded (Y/N) |
| Bank statements (Primary checking) | Drive/Taxes/Bank | Jan – Dec | |
| Credit card statements | Drive/Taxes/CC | Jan – Dec | |
| Merchant payout CSVs (Stripe/Square/PayPal) | Drive/Taxes/Merchant | Jan – Dec | |
| Payroll registers & tax deposits | Drive/Taxes/Payroll | Jan – Dec | |
| Prior year tax return | Drive/Taxes/PriorYear | YYYY | |
| Fixed asset invoices & schedule | Drive/Taxes/FixedAssets | All | |
| Sales tax returns | Drive/Taxes/SalesTax | Jan – Dec | |
| 1099 vendor list & W-9s | Drive/Taxes/1099s | Jan – Dec |
CSV copy (paste into a sheet)
Document,File Location / Link,Date Range,Uploaded (Y/N)
Bank statements (Primary checking),Drive/Taxes/Bank,Jan-Dec,
Credit card statements,Drive/Taxes/CC,Jan-Dec,
Merchant payout CSVs (Stripe/Square/PayPal),Drive/Taxes/Merchant,Jan-Dec,
Payroll registers & tax deposits,Drive/Taxes/Payroll,Jan-Dec,
Prior year tax return,Drive/Taxes/PriorYear,YYYY,
Fixed asset invoices & schedule,Drive/Taxes/FixedAssets,All,
Sales tax returns,Drive/Taxes/SalesTax,Jan-Dec,
1099 vendor list & W-9s,Drive/Taxes/1099s,Jan-Dec,
Here’s a ready-to-use CSV you can open in Google Sheets or Excel.
Download the CSV — Tax Season Upload Index
How we help
We prepare your books for tax season by organizing supporting documents, reconciling accounts, preparing schedules for your CPA, and identifying missed deductions or tax issues. We can work with your CPA or file-ready packages if you prefer to keep tax prep in-house.
Next steps / CTA
- Use the upload index above and gather documents into a shared folder.
2. Book a Tax-Prep Readiness Call: https://calendly.com/mrbrian-gieslertranbookkeeping/30min
3. We’ll provide a tax-ready package and a short remediation plan if issues are found.
FAQs
Q: When should I start preparing?
A: Start 6–8 weeks before your filing deadline to allow time for reconciliations and corrections.
Q: Can you prepare amendments if we find issues?
A: Yes — we can prepare schedules and work with your CPA to draft amended returns; fees may apply depending on scope.
Q: Do you handle sales tax filings?
A: We can help compile sales tax returns and supporting schedules, but filing may be handled by your tax partner or through your sales tax software.
Tax season doesn’t have to be a scramble. Gather the files above, run the checklist, and breathe easier. Need help? Book a free 30-min Tax-Prep Readiness call.
Giesler-Tran Bookkeeping • gieslertranbookkeeping.com • 971-200-5158