Do a month of bookkeeping in one sitting

What does this setup do?

Run a monthly bookkeeping close: categorize transactions, spot problems, summarize the month

Who is it for?

A small business owner whose bookkeeping is 3 months behind and dreads tax time

How do you set it up?

Tools

• ChatGPT or Claude (free tier works)
• Monthly bank and card statements as CSV exports
• Your list of expense categories, or let the AI suggest Schedule C buckets

Steps

1. Export last month's transactions from your bank and cards as CSV. Most banks have an export button.
2. Remove or mask full account numbers before uploading anything to a chatbot.
3. Paste the prompt below and upload the CSV files.
4. The AI categorizes each transaction and flags ones it is unsure about.
5. Review every flagged transaction yourself. This is the part you cannot skip.
6. Ask the AI for a month summary: total income, total expenses, biggest categories, anything unusual.
7. Save the categorized file and the summary in a folder named for the month. Done until next month.
8. After categorizing, run the reconciliation pass: match each transaction in your books to the same entry on the bank statement, line by line, and mark what matches. List everything left over on either side.
9. For the leftovers, add bank fees and interest you missed to your books, and keep a short list of outstanding checks and deposits in transit that explain the gap. The adjusted balances must match to the cent before you close the month.

I am doing my monthly bookkeeping. I have attached CSV exports of last month's business bank and credit card transactions. Categorize each transaction into these buckets: [LIST YOUR CATEGORIES, or use: advertising, supplies, software, travel, meals, rent, utilities, contractors, other]. Flag any transaction you are unsure about and tell me why. Then give me a summary: total income, total expenses, net for the month, the three biggest expense categories, and anything that looks unusual compared to a normal month.

Which chat tools work with this prompt?

Paste the prompt into any of these assistants (free or paid tiers).

• ChatGPT
• Claude

What tips make it smoother?

• Do it on the same day each month, like the 5th. Routine beats motivation.
• Never paste full bank account numbers or login credentials into a chatbot. CSV exports do not need them.
• Keep a running list of your categories and reuse it. Consistency is what makes year-end easy.
• Write a two-line note about anything unusual each month. Future you will thank present you.
• Sort both lists by amount while matching. A transposed number, like 54 typed as 45, shows up fast when the neighbors sit side by side.

Where do the claims come from?

Summaries use public sources linked below, not independent verification. How setups are picked.

• Read kCole Bookkeeping’s write-up (www.kcolebookkeeping.com)

  kCole Bookkeeping: Month-end checklist: categorize, reconcile, review AR/AP, run P&L, save documentation.

• Read Demar Consulting Group’s write-up (demarconsultinggroup.com)

  Demar Consulting Group: Monthly close routine: collect records, reconcile, review reports, turn findings into actions.

• Read Xero’s write-up (www.xero.com)

  Xero: Supports the walkthrough: compare opening balances, match transactions one by one, investigate unmatched items (outstanding cheques, deposits in transit, fees), adjust books, confirm closing balances match.

• Read NumberSquad’s write-up (numbersquad.com)

  NumberSquad: Supports the failure modes: transposed numbers, missing deposits, unrecorded fees, and the rule that reconciliation is not done until the difference is zero.