Categories / Invoicing/
Three-stage invoice chase
Solo consultant · 14 invoices went through the sequence in 90 days
- Task
- write firm-but-polite overdue emails in her own tone and stop avoiding chasing
- Result
- over 90 days, 14 invoices went through the sequence: 9 paid after the Day 3 or Day 14 email (avg ~9 days faster than her old single nudge), 3 paid after the Day 30 email that mentions statutory interest, 2 never paid on time. ~40 min to build; 2–3 hrs/month saved
- Tools
- ChatGPT (or Claude)
- Xero or QuickBooks automatic overdue reminders
- calendar reminders
- Setup
- paste 2–3 of your past chase emails so AI learns your tone → ask for a Day 3 / Day 14 / Day 30 sequence with invoice number, amount and due date as placeholders → add one calm line about statutory late-payment interest (UK: 8% + base rate) → either set calendar reminders or paste the wording into Xero/QuickBooks automatic overdue reminders → re-read Day 14/30 emails before sending (5-minute edit) → take 30–50% deposits and put late-payment terms in contracts for repeat late payers
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A ready-to-send prompt built from this card. Your AI will ask a few questions about your business, then give you a beginner setup plan.
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Help me set this up for my business: "Three-stage invoice chase".
Example business: UK freelancer/consultant (solo) with £14,200 in unpaid invoices at the start. Task: write firm-but-polite overdue emails in her own tone and stop avoiding chasing.
Reported result: over 90 days, 14 invoices went through the sequence: 9 paid after the Day 3 or Day 14 email (avg ~9 days faster than her old single nudge), 3 paid after the Day 30…
Tools: ChatGPT (or Claude), Xero or QuickBooks automatic overdue reminders, calendar reminders
Setup outline:
1. paste 2–3 of your past chase emails so AI learns your tone → ask for a Day 3 / Day 14 / Day 30 sequence with…
First, ask me up to 5 questions about my business and tools. Then give me a beginner step-by-step setup plan, plus copy-paste prompts/templates I can use. Plain English, and tell me if any step needs a tech helper.
via autopilotbusiness.ai/use-case/owner-uses-chatgpt-to-write-a-3-stage-invoice-chase-sequence-14-invoic/Step-by-step setup guide + copy-paste prompt
What's AI here: the AI writes and tightens the wording in your own voice. Sending is manual or rule-based (calendar reminders, or Xero/QuickBooks automatic reminders).
Prerequisites
- A free ChatGPT or Claude account.
- Two or three of your past chase emails, and one email from an easy client and one from a hard client.
Step-by-step setup
Step 1. Teach it your tone. Open a new chat (or a Project in ChatGPT or Claude) and paste in your past emails. Ask it to describe your natural tone.
Step 2. Generate the sequence. Use the prompt below to get three emails: Day 3 (friendly), Day 14 (firm, states amount and days, no apology), Day 30 (direct, mentions late-payment interest).
Step 3. Add the interest line. In the UK you can charge statutory interest on late business-to-business invoices (8% above the Bank of England base rate, plus fixed compensation). The author found one calm sentence about it did the most work, and would use it at Day 14 next time. Check the rules that apply where you are before quoting any figure.
Step 4. Put it on a schedule. Either set calendar reminders for Day 3, 14 and 30 after each due date, or turn on your accounting software's automatic reminders and paste the AI-written text in. In Xero: Sales → Invoices → Invoice Reminders, tick Email customers when an invoice is, and edit the 7/14/21-day reminders (up to five). In QuickBooks Online: Settings → Account and settings → Sales → Reminders.
Step 5. Re-read before you send. The author never sends the Day 14 or Day 30 email without a five-minute re-read, because drafts can drift too soft or too stiff.
Step 6. Fix the cause too. If you chase the same clients every month, take a 30–50% deposit and put a late-payment clause in contracts before work starts.
Copy-paste prompt
Here are three emails I've sent clients (paste). Describe my tone in 3 bullet points.
Now write a 3-email overdue-invoice sequence in that tone:
- Day 3 after due date: friendly, assumes an oversight.
- Day 14: firmer, names the amount and days overdue, asks for a payment date this week. Never apologise for asking to be paid.
- Day 30: direct, notes that late-payment interest may apply, asks for payment by Friday.
Leave placeholders for [invoice no.], [amount], [due date], [client name]. Under 100 words each.Sources
- Freelancer's 90-day write-up: "I let AI write my invoice chase emails". Credit: a UK freelance consultant (first-hand).
- Xero invoice reminders walkthrough (Xero Central video). Menu names may differ slightly.
- QuickBooks: Send invoice reminders automatically or manually
Industries: AI automation for Agencies & Consultancies
Results as reported by the source; not independently verified. Community-sourced from public sites and attributed to the source platform. Original author? Ask us to correct or remove it. Read the disclaimer.