Write a 3-email invoice-chase ladder. Each email gets firmer; none apologize.
- Email 1 (3 days past due): polite reminder, 3 lines max, offer to resend or change payment method.
- Email 2 (7 days past due): firmer, ask for confirmation of expected payment date, offer to fix any invoice issue within an hour.
- Email 3 (14 days past due): name the operational impact ('this is blocking the next phase of work I scheduled for {{date}}'). Ask for a date this week. Loop them in if there's a procurement issue you're not seeing.
No apology cushions ('sorry to bother you,' 'I know you're busy'). You're not in the wrong for asking to be paid.
Invoice details:
{{invoice_details}}
Invoice-chase ladder (3 emails)
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Example output
Email 1 (3 days past due):
Subject: Re: Invoice #1042
Hi Maya - quick reminder that invoice #1042 ($4,200) was due Tuesday. Easy to miss in a busy week. Reply if you need a fresh copy or a different payment method.
- Ivan
---
Email 2 (7 days past due):
Subject: Invoice #1042 - now a week past due
Hi Maya - invoice #1042 is now 7 days past due. Can you confirm the expected payment date? Happy to adjust the method if there's a hold-up on your end.
If the invoice itself has an issue (wrong PO, wrong amount, missing info), tell me what to fix and I'll resend within an hour.
- Ivan
---
Email 3 (14 days past due):
Subject: Invoice #1042 - blocking next sprint
Hi Maya - invoice #1042 is now 14 days past due. I have the next phase of work scheduled to start Monday and need the invoice cleared before I can begin.
Can you give me a date this week when payment will land? If there's a procurement issue I'm not seeing, loop me in and I'll work it directly.
- Ivan
Common mistakes
Don't apologize in any of the three emails - the apology cushion ('sorry to bother you,' 'I know you're busy') makes you look like you're in the wrong for asking to be paid. You're not. Also: don't merge the three emails into one. The escalation ladder works because each email has its own tone; collapsing them into one polite-but-firm message dilutes both. Third mistake: never sending email 3. The 'blocking work' email is the one that gets paid - if you only send the gentle two, the invoice rolls into month 2.
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Why it works
Invoice chasing is the admin task solopreneurs avoid most aggressively because every chase email feels like an attack on the relationship. This prompt produces a three-email escalation ladder (polite first / firmer second / 'this is now blocking my work' third), each scheduled at the right interval (3 days / 7 days / 14 days past due). The ladder structure does the emotional work for you - you're not deciding email-by-email how firm to be, you're following a plan you set up once. The third email explicitly names the operational impact ('this is blocking work I scheduled for X') instead of guilting the client about cash flow. Operational language gets paid; emotional language gets ignored. Tested cleanest on Claude Opus 4.7.