Chase an Overdue Invoice Without Burning the Relationship
Gives you a three-stage escalation ladder — friendly nudge, firm follow-up, and formal notice — plus the decision points for when to stop work or escalate. Use it when an invoice has passed due and you don't want to sound either meek or aggressive.
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Prompt
You are advising a freelancer on collecting an overdue invoice.
Invoice amount and what it was for: {{invoice}}
Due date and how far past due it is: {{days_overdue}}
Payment terms we agreed: {{terms}}
What I've already sent: {{prior_contact}}
The relationship — one-off client, ongoing, want to keep them: {{relationship}}
Whether work is still in progress: {{work_status}}
Give me an escalation ladder. For each stage: when to send it, the exact message, and what to do if there's no reply.
**Stage 1 — the nudge (a few days past due).** Assume it's an oversight, because usually it is. Warm, brief, resends the invoice, makes paying frictionless. No mention of terms or consequences.
**Stage 2 — the firm follow-up (around 14–21 days past due).** Still polite, now unmistakable. References the agreed terms, asks a direct question — is there a problem with the invoice, or a process delay on their end? — and requests a specific payment date rather than a vague commitment. Ask for the accounts-payable contact directly.
**Stage 3 — formal notice (30+ days).** States the amount, the days overdue, any late fee the contract allows, and a firm deadline. Names what happens after that deadline: work pauses, deliverables are withheld, or the debt is escalated. Professional and unemotional. No threats I won't follow through on.
Also give me:
- The phone-call script, because a call collects faster than email.
- When to stop working, given {{work_status}} — and the sentence that communicates the pause without drama.
- How to reply if they say "cash flow is tight": the payment-plan offer that gets me paid something now.
- What to change in my terms next time so this is less likely: deposit, milestone billing, shorter net terms, late fees.
Never apologize for asking to be paid for completed work.
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