Which late invoice should you chase first?

Chasing money is unpaid work, so it should be aimed. Not at the biggest invoice, and not at the oldest one. At the one where age and amount multiply into the biggest risk.

Guide · FantasyLab ·

The method, plainly

Score each open invoice as amount × weeks late. A $1,180 invoice at 19 days late outranks a $2,000 invoice at 4 days, because an invoice gets harder to collect the longer it sits. Chase the top score first, and send the first nudge before it hits 30 days.

The escalation ladder

  1. Day 3 past due: a friendly re-send with the invoice attached. Most lateness is disorganization, not refusal.
  2. Day 10: a direct note naming the amount and the date, plus the easiest possible way to pay. Remove every step between them and the payment.
  3. Day 20: a phone call. Voices collect what emails can't.
  4. Day 30: new terms for this client going forward: deposit up front or card on file. Think of it as pricing their risk.

The pattern matters more than the invoice

One late invoice is weather. The same client late three times is climate. You're working as their line of credit, interest-free. Price it, require deposits, or plan their replacement. Your receivables list, sorted by that score once a week, is one of the highest-paid five minutes in your business.

Common questions

Should I charge late fees?
A stated late fee changes behavior even when you waive it. What it mostly buys you is a reason for the day-10 email to exist. Deposits and card-on-file work better than fees for repeat offenders.

Counsel

Counsel does this math on your real numbers.

Connect Stripe, Square, Shopify, Etsy, QuickBooks or a bank feed, or drop in a CSV. Every answer comes with a receipt that shows the method, the sample size and how confident it is. When the math isn't conclusive, the app says so.

Every figure on this page is computed from Counsel's demo businesses or from the numbers you type in. None of them are made up. This is cash math, not tax or legal advice. Written and kept up to date by the founder.