Catch up months of overdue bookkeeping by filing each vendor where your books already put it: AI agent prompt
When the books are a year behind, the slow part is pulling every statement and deciding where thousands of transactions go. Let an AI do the sorting, but only by your own history: a vendor you've filed the same way before goes there again, and anything uncertain comes to you once and becomes a rule. In posts from Oct 15-20, 2026, Kris Collo described doing this for a friend's private school: an AI agent downloaded 15 months of bank and card statements and check images, loaded over 2,000 transactions into the free accounting app SlowBooks Pro overnight, filed vendors seen 3+ times in the same category 80% of the time, and sent only a few dozen to the general manager. The line-by-line pass also found a double-paid accounting fee and charges that kept running after being cancelled (his figures, unaudited).
FinanceBookkeeping backlog cleanupintermediateThe prompt
Help me catch up my overdue books for [business name]. Here are my bank and card transactions for [months]: [paste or attach CSV with date, payee/description, amount]. Here's how my books categorized past transactions: [paste or attach an export with payee and category], and my category list: [paste chart of accounts]. Rules: 1) If a payee appears at least 3 times in my history and went to the same category at least 80% of the time, use that category and show the count (e.g. 5/6). 2) Otherwise don't guess: put it on a questions list with your best guess and where this payee usually goes. 3) Clean up payee names first (drop store numbers, dates and card-processor prefixes like 'SQ *'). Give me two tables: 'Filed by history' and 'Questions for me'. Then list anything odd you noticed while reading every line: duplicate payments, recurring fees, subscriptions still charging, unusual amounts. Don't post anything to my accounting software; I'll review first. After I answer the questions, turn each answer into a simple rule (payee -> category) I can reuse next month.
How to use it
- Copy the prompt above.
- Replace every [bracket] with your own details (or fill in the blanks on AgentPlaybook Real Estate, which remembers your answers for the next prompt).
- Paste it into ChatGPT, Claude, SlowBooks Pro and review the answer before you use it.
Works with: ChatGPT, Claude, SlowBooks Pro, QuickBooks, Google Sheets
Real-world example: agentsfinance.io/entries/case-private-school-bookkeeping-backlog-slowb
Featured in: AI prompts for Google Sheets and Excel work
Before you use it: what to check
Already built into this prompt
- Don't post anything to my accounting software; I'll review first.
Check yourself
- Check every figure, price and total against your own records before anything is sent, posted or booked. A person approves refunds, discounts, payments and price changes.
- Remove names, contact details, account numbers and other personal data the task doesn't need before you paste, and check your AI tool's data and training settings.
- Read and edit the draft before it reaches a customer or goes public. If you later automate this prompt, start with "draft and notify me", not "send automatically".
- Check names, dates, numbers and any claim against your own source material before you use the answer. AI can misread or invent details.
Using an AI agent? Download this prompt as a SKILL.md agent skill with these checks built in, or get the .zip for Claude.ai. How to install skills.
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