Late Invoice Escalation Skill

Most late invoices are disorganization, not theft — which is why the ladder starts friendly and blames the invoice, not the client. But freelancers fail at both ends: waiting four months of "gentle bumps" that teach the client lateness is free, or going nuclear at day 35 and torching a recoverable relationship. This skill runs the graduated ladder — each rung dated, worded, and slightly firmer — with the two real decision points marked: when work stops, and when the relationship is already gone and only the money remains.

What This Skill Produces

• The situation read — likely-disorganized vs. cash-crunched vs. disputing vs. ghosting, from the evidence
• The escalation ladder — dated rungs with verbatim send-ready messages, each escalating one notch
• The decision points — when ongoing work pauses, when it's final-demand time, and what the post-relationship options actually are
• The prevention terms — deposits, milestones, late fees, and stop-work clauses for every future agreement

Required Inputs

Ask for these if not provided:

• Invoice facts — amount, issue date, terms (net-15/30), days overdue, and whether a contract/PO backs it
• The trail so far — reminders sent, any client responses (a "sorry, next week!" and dead silence are different ladders)
• Relationship state — ongoing work happening now? future work wanted? (leverage and tone both change)
• The client's shape — enterprise AP department (slow by process — chase the process), small business (chase the person), or a known cash-crisis (a payment plan beats a write-off)

Framework: The Ladder Rules

1. Rung 1 (due +3–7 days), assume the best: "Just flagging this may have slipped through — invoice #N for $X was due [date], reattached for convenience." Blames the invoice's journey, not the human. Most cases end here.
2. Rung 2 (+14), add specificity and a question: "Following up on invoice #N, now two weeks past due. Can you confirm when payment will be processed?" A direct question demands an answer; silence after it is information.