late-invoice-escalation

# 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. 3. **Rung 3 (+30), firm with consequence preview:** "Invoice #N is 30 days past due. Per our terms [cite late-fee clause if it exists]. I need payment or a payment date by [specific date] — after that I'll need to pause work in progress." Only preview consequences you'll execute. 4. **The work-stop (the real leverage, use it once):** ongoing work pauses when promised dates pass — stated as procedure, not anger: "Pausing work until the account is current; happy to resume immediately on payment." Never threaten it twice — the second unexecuted threat marks every future rung as bluff. 5. **Rung 4 (+45–60), final demand, relationship already spent:** total owed, hard deadline (7–10 days), and the named next step — collections agency, small-claims filing (designed for exactly these amounts, no lawyer needed), or a demand letter. At this point being collectable beats being liked; a genuine cash-crisis client gets offered a written payment plan with dates *once* instead. ## Output Format # Collection Plan: invoice #[N], $[X], [D] days overdue ## The Read [Which failure mode the evidence suggests · what that changes about pace and tone] ## The Ladder | Rung | Date to send | Channel | Message (verbatim) | |---|---|---|---| [Each message ready to paste · rungs already burned marked done] ## Decision Points Work-stop: [trigger date and exact wording] · Final demand: [date, total, named next step] · Payment-plan branch: [if cash-crisis, the once-only offer] ## Prevention (every future client) Deposit [%] before work starts · milestone billing over monthly-in-arrears · late-fee clause [% per month, where lawful] · stop-work clause · for enterprise: PO + AP contact captured before work begins > Late-fee enforceability, demand-letter form, and small-claims limits vary by jurisdiction — verify locally; for large amounts or a contract dispute, a lawyer's letter early can be cheaper than months of the ladder. ## Quality Checks - [ ] Every rung has a date and verbatim text — a ladder without dates is a mood - [ ] Rung 1 is genuinely warm — no passive-aggressive garnish - [ ] Consequences are previewed exactly one rung before execution, and executed on schedule - [ ] The work-stop is stated as procedure, not punishment - [ ] Prevention terms appear — the best collection is the deposit you took up front ## Anti-Patterns - [ ] Do not send rung-1 wording six times — repetition without escalation teaches that lateness is free - [ ] Do not threaten what you won't execute — one hollow threat converts the whole ladder to noise - [ ] Do not vent in writing — every message should read fine attached to a small-claims filing, because it might be - [ ] Do not keep delivering new work into an unpaid account past the stop trigger - [ ] Do not skip the read — an enterprise AP maze, a cash crisis, and a ghost need different ladders, not one angrier email