Look. You've got money sitting out there right now that you earned weeks ago. And you haven't chased it, because chasing it feels like begging for something that's already yours, and because you don't want to torch a relationship over a bill that's probably just sitting in somebody's stack.
That's the trap. You wait, it gets more awkward, and the longer you wait the more it feels like a confrontation instead of a reminder. So it never happens and you eat it.
Here's the thing. The reason it feels awkward is you're writing the message from scratch, at 9pm, annoyed. Write all three of them once, right now, calm. Then it's not a confrontation. It's a step in a process, and processes aren't personal.
What you need
- Claude
- Email and your phone
- A calendar
Setup
- Run the prompt below. You get three messages: day 3 past due, day 14, day 30.
- Save them where you can grab them fast.
- When you send any invoice, drop three calendar reminders in at those marks. Delete them the second you get paid.
- Send message 1 and 2 by email so there's a paper trail. Message 3 goes by email AND a phone call the same day. Not one or the other.
- Attach or link the actual invoice to every single one. Half the time the reason it's unpaid is nobody can find it.
The prompts
Write the three messages:
I run a [YOUR BUSINESS TYPE] in [YOUR CITY]. My customers are
[WHO: homeowners / other businesses / property managers / patients].
Typical invoice is [AMOUNT RANGE]. My terms are [YOUR TERMS,
example: due on receipt, net 15, net 30].
Write me 3 escalating messages for an unpaid invoice.
MESSAGE 1, 3 days past due, email. Under 80 words. This assumes it's
an honest oversight, because it usually is. Warm, zero accusation.
Restate the invoice number, amount, and how to pay in one line.
MESSAGE 2, 14 days past due, email. Under 120 words. Firmer. Still
professional. Ask a direct question that requires an answer, so they
can't just not respond. Give them a way to tell me there's a problem
if there is one.
MESSAGE 3, 30 days past due, email. Under 150 words. This is the last
one before it goes somewhere else. Clear, unemotional, states exactly
what happens next and by when. No threats, no anger, no capital
letters. It should read like a policy, not like I'm mad.
Rules for all three:
- Never sarcastic, never passive aggressive
- Never "as per my last email"
- Refer to the customer as they/them, I don't know who's reading it
- Subject lines under 50 characters, and each one different so they
don't thread together and get ignored
- Written the way I talk: [DESCRIBE OR PASTE A SAMPLE]Write the phone script for day 30:
Same business. Write me what to say on the phone when I call about the
30-day one. Under 60 seconds spoken. Include:
- The opening line
- What to say if they say the check is in the mail
- What to say if they say they're unhappy with the work
- What to say if they say they can't pay right now
- How to end it with a specific commitment and a date
Keep me calm and in control the whole way. Don't have me apologize for
asking to be paid.Write a payment plan offer:
Same business. Sometimes people genuinely can't pay all at once.
Write me a short email offering a payment plan, under 120 words. It
should protect me (specific amounts, specific dates, what happens if a
payment is missed) without sounding like a legal document. Make it
easy to say yes to.What to check before you trust it
Verify the invoice is actually past due before you send anything. Check your terms, check the date you sent it, check whether the payment already came in and you didn't mark it. Nothing burns a customer relationship like a past-due notice on something they paid last Tuesday.
Never put a threat in writing that you're not going to follow through on. If message 3 says it goes to collections on the 15th and it doesn't, every future message you send is noise.
Read the tone once more before sending. You wrote these calm. Send them calm. Do not add a line at 11pm because you're frustrated.
If you're in an industry with rules about how you can collect a debt, and a lot of you are, know them before you send message 3. That's a real thing with real teeth in some states, and a template doesn't know where you live.
Keep every one of these. Date, time, what you sent. If it ever goes further than a nudge, that record is the whole ballgame.
— Jordan