Best Overall
Claude
Calm escalation ladder; won’t invent fees if told not to.
Open Claudesmall business · ~25 min
Not legal or collections advice. Use only invoice facts and fee language you already have. Do not invent late fees, interest, or legal threats.
Best Overall
Calm escalation ladder; won’t invent fees if told not to.
Open ClaudeBest Free
Enough for a three-email sequence from pasted facts.
Open ChatGPTBest Power-User
Draft the sequence in one; hostility / invented-threat check in the other. Keep amounts in your AR/Sheets source of truth—chat is for wording only.
Open ClaudeStep 1 of 5
Invoice #, amount due, original due date, days overdue (or ages for day-7/14/30 drafts), customer name + billing contact, payment link/instructions you already use, prior reminder dates if any, and any late-fee or pause-work terms that are already in your contract/invoice—or write NONE.
Step 2 of 5
Paste the rules first so the model cannot mint a late fee or a legal threat.
Copy-paste prompt
Draft a late-invoice email sequence for my small business. Hard rules: - Use ONLY invoice facts, payment instructions, and fee/terms language I provide. Do not invent late fees, interest, statutory penalties, legal threats, credit reporting, or “collections agency” steps. - This is NOT legal advice and NOT a debt-collection compliance guide. Keep language factual and professional. - Produce three emails: Day-7 (friendly nudge), Day-14 (direct reminder), Day-30 (firm, still non-threatening). Same facts; escalating clarity only. - Include subject lines and a clear ask + how to pay using MY payment instructions. - If amount, due date, or fee language is missing, mark [NEED FACT]—do not fill numbers. Confirm in one sentence, then wait for my pack.
Step 3 of 5
Paste invoice facts, then send the generate command. If a fee or “we will sue” line appears that you did not type, delete it.
Paste pack
CUSTOMER / COMPANY: [ ] BILLING CONTACT (if known): [ ] INVOICE #: [ ] AMOUNT DUE: [ ] CURRENCY: [ ] ORIGINAL DUE DATE: [ ] DAYS OVERDUE TODAY (or target for each draft): [ ] PAYMENT TERMS ON INVOICE: [e.g. Net 15 / Net 30] PAYMENT INSTRUCTIONS I ACTUALLY OFFER: [link / ACH / check address] PRIOR REMINDERS SENT: [dates or NONE] LATE FEE / INTEREST LANGUAGE ALREADY IN MY CONTRACT OR INVOICE: [paste or NONE] WORK STATUS: [completed / ongoing / on hold] RELATIONSHIP NOTES (optional, factual): [ ]
After you send the filled pack, copy the Generate command in the next box and paste it into the SAME chat so the AI runs the decision tree / produces the output.
Generate command — copy and send this next (same chat)
Draft Day-7, Day-14, and Day-30 emails now. Subject + body for each. Keep under ~150 words each. Mark [NEED FACT] gaps. No invented fees or legal threats.
Step 4 of 5
In the other tool, paste the sequence plus your invoice facts:
Second-model check
Here is a day-7/14/30 invoice follow-up sequence from another assistant plus my invoice facts. Find: (1) any invented fees, interest, or legal threats, (2) wrong amounts/dates vs my pack, (3) hostility that could damage a good client, (4) missing payment instructions. Return only corrections. Not legal or collections advice.
Step 5 of 5
Attach or link the real invoice. Log send dates in AR. If the customer disputes the work, stop the sequence and resolve the dispute—do not use AI to argue merits.