Let’s start over and see if we can take this one step at a time. I want to begin by creating another GPT or agent who will be a personal assistant and bookkeeper/accountant – and who may ultimately grow into the CFO role, but for right now is just learning about the organization and its finances, and offering to help in whatever ways it can, e.g., reviewing spreadsheets for missing categories or misclassifications, compiling reports, etc
Got it. Let’s design this “Personal Assistant + Bookkeeping Agent” in a way that’s genuinely useful now (cleaning up spreadsheets, catching miscategorizations, producing basic reports) and also sets a clean runway toward a future “CFO brain” without overreaching.
Below is a step-by-step build you can implement immediately in ChatGPT as a custom GPT (or replicate as an internal agent later).
Step 1: Define the agent’s current job (and its boundaries)
What it
does now
(Phase 1: Learning + Hygiene)
Personal assistant (ops-finance focused)
- Maintains “finance admin” task list (receipts, reimbursements, invoices, vendor W-9s, renewals).
- Drafts email language for billing, payment follow-ups, invoice templates, reimbursement requests.
- Creates monthly close checklist for humans (what to export, reconcile, confirm).
Bookkeeping / accounting support
- Reviews spreadsheets for:
- Missing categories
- Misclassifications (e.g., grant income vs donations; contractors vs payroll; program vs admin)
- Duplicates, broken formulas, inconsistent date formats
- Unreconciled totals vs bank exports
- Produces lightweight reports:
- Monthly P&L (simple), cash-in/cash-out, runway estimate (based on current cash and average burn)
- Vendor spend summary
- Grant/Restricted funds tracker (if applicable)
What it
does NOT do yet
(Guardrails)
- It does not file taxes, certify compliance, or claim it’s a licensed accountant.
- It does not make final coding decisions without a human approval step.
- It does not move money or initiate payments (unless you explicitly build that later).
This boundary is important because it keeps the agent helpful without becoming a risk surface.
Step 2: Decide what “good” bookkeeping looks like for your org (a minimal chart of accounts)
You don’t need a perfect chart of accounts yet. You need a stable one.
A Phase-1 structure that works for most early regenerative/nonprofit entities:
Income
- Grants – Restricted
- Grants – Unrestricted
- Donations – Individual
- Donations – Institutional
- Program Revenue / Consulting
- Memberships / Events (if relevant)
- Other Income
Expenses (Program / Admin / Fundraising tags later)
- Contractors / Consultants
- Payroll (if any)
- Professional Services (legal, accounting)
- Travel
- Events / Convenings
- Software / Tools
- Office / Remote work (postage, supplies)
- Insurance
- Banking / Payment processing fees
- Marketing / Comms
- Research / Field costs
- Fiscal sponsor fees (if applicable)
- Other / Uncategorized (temporary bucket with a “must-clear monthly” rule)
Balance sheet basics (tracking only)
- Cash (by account)
- Accounts Receivable (invoices outstanding)
- Accounts Payable (bills due)
- Restricted Funds Liability (if you track restricted cash this way)
Your agent can help you refine this, but starting here gives it a spine.
Step 3: Provide the agent a “decision framework” for categorization
Give it a simple set of rules so it can flag issues consistently:
Categorization rules (examples)
- If it’s paid to an individual for work → Contractor/Consultant (unless payroll)
- If it’s a platform subscription → Software/Tools
- If it’s flights/hotels/meals for travel → Travel
- If it’s legal/accounting/bookkeeping → Professional Services
- If it’s directly tied to delivery of program work → Program tag
- If it’s operations overhead → Admin tag
- If it’s donor outreach or fundraising event → Fundraising tag
Confidence + escalation
- The agent must label suggestions as:
- “High confidence recode”
- “Needs your decision (two plausible categories)”
- “Insufficient info (ask for memo/receipt/context)”
Step 4: Create the agent’s operating rhythm (what it produces each week/month)
Weekly
- “Inbox triage” list: bills due, receipts missing, invoices to send, follow-ups
- “Coding review”: 10–30 line items flagged with recommended recodes + reasoning
Monthly
- Close checklist completion tracker
- Simple P&L + variance notes (what changed from last month)
- Cash runway estimate
- Outstanding receivables/payables list
- Uncategorized clearing report (everything still in “Other/Uncategorized”)
This turns the agent into a cadence engine.
Step 5: What you’ll upload/share so it can actually work
Minimum viable inputs:
- Latest transactions export (CSV) from bank/credit card OR your master spreadsheet
- Current budget (even if rough)
- Any grant restriction notes (even a simple doc)
- Vendor list (optional)
Rules:
- Redact account numbers.
- If you’re under a fiscal sponsor, include sponsor reporting requirements (what formats they want).
Step 6: The actual Custom GPT setup (copy/paste ready)
Name ideas
- LedgerSeed
- OakCFO (Apprentice)
- Possible Planet Finance Mate
- CFO-in-Training
Short description
“Ops-focused personal assistant + bookkeeping support for a regenerative organization. Reviews spreadsheets, flags miscategorizations, compiles monthly reports, and maintains a finance admin task list—always with human approval for final coding.”
Core instructions (system-style prompt you can paste)
Use this as the “Instructions” section for the GPT:
Role
You are an ops-focused personal assistant and bookkeeping support agent for a mission-driven organization. You help organize financial data, flag inconsistencies, suggest categorizations, and produce lightweight internal reports.
Boundaries
- You are not a licensed accountant or attorney. Do not provide legal/tax advice.
- Do not finalize changes without explicit user approval. Always propose changes as recommendations.
- Do not invent missing numbers. If uncertain, ask for the needed artifact or label as “insufficient info.”
Operating principles
- Be conservative and transparent: show reasoning and confidence level.
- Maintain an “Open Questions” list for missing info needed to categorize or reconcile.
- Prefer simple, stable categories over overly granular ones.
- Track restricted vs unrestricted funds clearly when relevant.
Default outputs
When given transactions or spreadsheets, produce:
- Issues & anomalies (duplicates, gaps, inconsistent formats)
- Recommended recodes (table-style list: date, vendor, amount, current category, suggested category, confidence, note)
- Reports (P&L summary, cashflow, runway estimate if cash provided)
- Next actions (top 5 finance-admin tasks)
Step 7: The first task to give the agent (low effort, high signal)
To “train” it on your patterns, start with one concrete file and one concrete output:
Task 1: Transaction hygiene pass
- Upload your current transaction sheet/export.
- Ask: “Flag anything uncategorized, suspicious, duplicated, or likely misclassified. Propose recodes with confidence levels.”
Task 2: Create your monthly close checklist
- Ask: “Create a monthly close checklist for our current workflow (spreadsheet-based), including reconciliation steps and report outputs.”
If you want, I can draft the exact “first conversation script”
Something like: what you paste into the agent on Day 1 to orient it (mission, entity structure, fiscal sponsor yes/no, accounts list, categories).
If you paste (1) your current categories list and (2) a screenshot or export of ~30–50 recent transactions, I’ll produce:
- a refined Phase-1 chart of accounts
- a categorization decision tree
- the first “recode suggestions” batch
- a monthly report template the agent can generate every month