Late Invoice Ladder
What it does
Writes the full escalation sequence for an unpaid invoice — friendly nudge, firm reminder, formal demand letter — each one calm, specific, and referencing only facts you gave it. It escalates the tone, not the truth, and tells you plainly when you’ve reached the step where a lawyer or small-claims process takes over from letters.
When to use it
- An invoice is 1 week late and you don’t want to sound desperate or aggressive
- It’s 30+ days and the polite version has stopped working
- You’re about to write something angry — run it through this first
The skill
Act as a calm, professional collections writer. Rules: use only the
facts I give you — never invent interest amounts, legal deadlines,
or statutory rights; never threaten action I haven't confirmed I'll
take; keep every letter something I'd be comfortable having read
aloud in court later; no fake "my legal team" if there isn't one.
The facts: [INVOICE NUMBER, AMOUNT, DUE DATE, WORK DELIVERED,
PAYMENT TERMS AGREED, ANY REPLIES SO FAR, MY COUNTRY/STATE]
Relationship: [ONGOING CLIENT I WANT TO KEEP / ONE-OFF / ALREADY SOUR]
Write me the three-step ladder:
1. THE NUDGE (send ~1 week late): friendly, assumes oversight,
restates amount + due date, makes paying easy.
2. THE FIRM REMINDER (send ~2-3 weeks late): professional, references
the nudge, sets a specific date, states plainly that work or
deliverables pause until settled (only if I confirmed that's true).
3. THE FORMAL DEMAND (send ~30-45 days late): a proper demand letter —
full facts, total owed, a final deadline, and a factual statement
of the next step I've told you I'm actually prepared to take.
Then tell me honestly: at what point letters stop being the tool,
and what my realistic next options are (small claims, collections,
a lawyer) — as OPTIONS TO RESEARCH for my jurisdiction, not as
legal advice. If late-payment interest is legally regulated where
I am, tell me to look up the current rate — do not invent one.
Example output
[TO FILL AFTER TESTING]
Tweaks
- Send step 1 earlier than feels comfortable — a week late is not rude, it’s bookkeeping
- Never skip to step 3 out of anger; the ladder read as a sequence is what makes the demand letter credible
- If they reply with a payment plan offer, take the conversation off the ladder and get the plan in writing
The honest line
Most invoices get paid at step 1 or 2. The ladder’s real job is keeping you professional while it happens — and telling you without drama when it’s time for small claims or a lawyer instead of a fourth email.