AI Prompts for Small Business Money and Cash Flow

Build me a true accounts receivable picture.

Use this source order:

1. Live accounting, invoicing, or payment systems first, such as QuickBooks, Xero, Stripe, Square, FreshBooks, Wave, or similar
2. Invoice exports, payment exports, spreadsheets, or invoice PDFs second
3. If neither is available, stop and tell me exactly which report to export and where to find it

Do not call anything overdue until you cross-check whether payment was actually received.

Show me:

1. Total outstanding amount
2. Every unpaid invoice by client
3. Aging buckets: current, 1-30 days, 31-60 days, 61-90 days, and 90+ days
4. The three clients holding the most outstanding money
5. Partial payments
6. Credits that appear unapplied
7. Invoices created but not sent
8. Anything that looks odd or inconsistent

Then draft a collection message for each genuinely overdue invoice.

Use the relationship history from my email before drafting:

- Good client under 30 days late: friendly nudge
- 31-60 days late: clear follow-up
- 61-90 days late: firmer message
- 90+ days late: flag as call-first and give me three talking points instead of an email

Mark every draft HOLD. Do not send anything.

End with one sentence: the single invoicing habit that would make this list shorter next month.

Analyze my business expenses.

Use live accounting or payment systems first. If you cannot access those, use exports, spreadsheets, bank/card reports, receipts, or expense files. If you have none of those, tell me exactly what report to download and from where.

Group expenses into plain business-owner categories:

- Payroll
- Contractors
- Software
- Rent or office
- Marketing
- Advertising
- Travel
- Professional services
- Taxes and fees
- Equipment
- Everything else

Then show me:

1. Total expenses for the period reviewed
2. The fastest-growing categories
3. The five biggest individual expenses
4. Recurring charges that look unusually high
5. Duplicate or suspicious charges
6. Expenses that do not clearly connect to revenue, delivery, retention, or operations

Keep it to one page. Use plain language, not accounting jargon.

Find every recurring subscription or recurring charge in my business.

Use accounting, bank/card, or payment data first. If unavailable, use invoices, receipts, email confirmations, or exports.

For each recurring charge, list:

1. Vendor
2. Monthly or annual cost
3. Billing frequency
4. What the tool or service appears to be for
5. Last evidence of use, if available
6. Whether it looks essential, questionable, or likely unused

Look for usage evidence in email alerts, login notices, invoices, files, calendar events, team references, or project records.

Flag anything with no evidence of meaningful use in the last 90 days.

At the top, show the total estimated annual savings if I cancel the likely-unused items.

Do not cancel anything. Give me a cancel-candidate list only.

Review my pricing.

Use proposals, invoices, contracts, website pages, sales emails, and service documents from the last two years.

Tell me:

1. When I last raised prices
2. My average project/order value by year
3. Which services are being quoted at the same price as one or two years ago
4. Which clients or offer types are still on old pricing
5. Where my scope has grown but the price has not

Then review three public competitors or comparable providers. Use only public information you can actually find. Tell me what they charge, how they package similar work, and where I appear underpriced or overcomplicated.

Do not tell me to "charge what I'm worth." Give me specific numbers and the reasoning behind them.

Rank my clients by profit per hour of attention, not just revenue.

Use invoices, payment records, proposals, email volume, meeting history, revision rounds, support requests, project delays, and client notes.

For each client, estimate:

1. Total revenue
2. Number of emails or threads
3. Number of meetings
4. Revision rounds or support requests
5. Timeline friction
6. Scope creep signals
7. Estimated attention required

Then rank:

- Best five clients by profit per hour of attention
- Worst five clients by profit per hour of attention
- The client who looks good on revenue but appears costly once effort is counted
- The client who is underrated because they are low-drama and profitable

Show the evidence used. Mark estimates clearly.

Analyze my client concentration risk.

Use invoices, payment records, and revenue data from the last 12 months.

Tell me what percentage of revenue came from:

1. My largest client
2. My top three clients
3. My top five clients

Then review the relationship evidence for those clients: contracts, renewal dates, payment history, recent email tone, meeting history, and any unresolved issues.

Tell me plainly:

1. What happens if the largest client leaves next month
2. Whether the relationship looks stable, uncertain, or at risk
3. The fastest two realistic moves to reduce this exposure
4. Which past or current clients are most likely to help fill the gap

Use numbers. Do not reassure me unless the evidence supports it.

Build a simple 90-day cash picture.

Use live accounting, payments, invoicing, payroll, and expense tools first. Use files and exports second.

Include:

1. Expected money in, by week
2. Expected money out, by week
3. Invoices due and their real due dates
4. Recurring charges
5. Payroll or contractor payments, if available
6. Known upcoming commitments from email, contracts, or calendar
7. Any payments that look uncertain

Lay it out week by week.

Flag any week that looks tight.

If a tight week exists, list the three fastest levers in order:

1. Which invoice to chase
2. Which expense to pause or delay
3. Which payment or commitment to renegotiate

Use a simple table. No accounting jargon.

Analyze my payment terms and actual payment behavior.

Use invoices, contracts, proposals, accounting records, payment records, and email threads.

Tell me:

1. Current payment terms I use
2. Average days-to-pay by client
3. Clients who consistently pay on time
4. Clients who consistently pay late
5. Services or project types where deposits should be required
6. Where my current terms create avoidable cash strain
7. Whether late fees are worth using for my client mix

Then draft:

1. A cleaner payment terms paragraph for future proposals
2. A deposit requirement paragraph where appropriate
3. A note for one or two chronic late payers, matched to the relationship

Mark all notes HOLD. Do not send anything.