The money conversation

⏱ 35 min8 steps

Asking to be paid feels awkward, even when the due date has come and gone. Raising your prices can feel worse. In this lesson you'll build a ladder of four reminders that go from friendly to firm, and a short note for when your prices go up. You'll send every one yourself. Have your handy. Getting stuck on the firmer messages is normal, and each step has fixes.

payment terms What you and the customer agreed about paying, like how much, by when and how. They're usually on the quote, the bill or the contract. All words

Steps

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Check what you and the customer agreed
Every reminder rests on what you agreed: the amount, the date it was due, and anything your terms say about paying late. Find that before Claude writes a word.

Rules on chasing late payments, late fees and collections depend on your contract and on the law where you and the customer are. Before you charge a late fee or hand a bill to a , check your contract, and ask a lawyer if you're not sure. Never say you'll do something, like passing the bill on or going to court, unless you're allowed to and you really will.
1. Find the quote, bill or contract for the job.
2. Write down the amount, the due date, and how the customer can pay.
3. Write down anything it says about late fees or interest. If it says nothing, write none.
collection agency A company that chases unpaid bills for a business, usually for a share of what it collects. All words
That's not what I see
We never agreed a due date in writing.
Then the reminders can't point to one. Use the date you sent the bill, and keep the messages to the friendly end. From now on, put the due date on every quote and bill. The lesson "Write the quote" has a FILL IN for it.
Start a new chat and set the rules
This sets the rules for every message before Claude writes one.

drafts and sorts; a person approves anything with a price, a date or your name on it. A reminder has all three, so Claude drafts and you check the amount and the date against your own records.

This part of the section is words and worksheets only. Claude writes the messages, and you send them. In these lessons you don't connect Claude to your bank, your card reader or your invoicing software. Don't paste customer names, bank details, card numbers or account numbers into the chat. [Name] stands in for the customer, and you fill in the rest when you send.
1. Open the or claude.ai and start a new chat.
2. Copy the prompt below.
```
I own a small business, and I want to write a set of short reminder messages for customers who haven't paid by the date we agreed. You'll help me in this chat. The rules: you draft, and I check and send every message myself. Keep every message polite and factual. No threats, no guilt, and no claims of legal action. Write as me and my business, never as a collection agency, a lawyer or another name. Never mention a late fee, interest or any next step unless I give it to you from my own terms. Never suggest contacting anyone except the customer. Use [Name] for the customer, and FILL IN for the amount, the bill number, the due date and how to pay. Never ask me for bank, card or account details. First, ask me one question at a time: what I do, how I usually bill, and what my payment terms say. My business: [what you do]
```
1. Paste it into the chat. Replace the part in square brackets with what you do, like plumbing, a print shop or bookkeeping for small firms.
2. Send it, then answer Claude's questions one at a time.
prompt What you type to Claude. A good one says what you want, how to work and what never to do. All wordsAI Short for artificial intelligence. Here it means a program like Claude that reads what you write and writes back in plain words. All wordsClaude app Claude on your phone or computer, where you chat with it by typing. claude.ai is the same thing in a web browser. All words
You should see:
Claude says it understands the rules, then asks its first question.
That's not what I see
Claude asked me everything at once.
Type this and send it: One at a time, please. Then answer the first one.
Have Claude draft the first, friendly reminder
Often a late bill has slipped someone's mind. The first reminder assumes that. This prompt drafts one in an email version and a text version.
1. Copy the prompt below.
```
Write the first reminder, for a few days after the due date. Assume it slipped their mind. Start with "Hi [Name],". Say which bill it's about, the amount and the date it was due, all as FILL IN. Say how to pay as FILL IN, and offer to resend the bill. Keep it under 60 words. Give me an email version and a text-message version.
```
1. Paste it into the same chat and send it.
2. Read it out loud, and change any word you wouldn't say.
You should see:
A short, friendly reminder in an email version and a text version, with FILL IN for the bill, the amount, the date and how to pay.
That's not what I see
It sounds stiff, like a letter from a bank.
Reply: Write it the way I'd say it to a regular customer at the counter.
Have Claude draft the next three reminders
Each reminder after the first gets a little firmer and stays polite. This prompt drafts reminders 2 to 4. The last one leaves the next step blank for you to fill in from your contract.
1. Copy the prompt below.
```
Now write three more reminders, each a little firmer than the last, and keep all of them polite. Second: a check-in that asks if anything is wrong with the work or the bill. Third: a plain note that the bill is still unpaid, with the amount and the due date, asking them to pay or call me by a date, as FILL IN. Fourth: a final, firm note that asks for payment or a call by a date, as FILL IN, and says what happens next only as NEXT STEP: CHECK MY CONTRACT FIRST, unless I've given you that step from my own terms and told you I'll really take it. Keep each one under 80 words. Number them 2 to 4.
```
1. Paste it into the same chat and send it.
2. Decide how many days apart you'll send them, and write the days next to each one.
3. Before you send the fourth one, replace the NEXT STEP line with a step your contract allows and you'll really take. If there isn't one, delete the line.
You should see:
Three more reminders, numbered 2 to 4, each firmer than the one before, with FILL IN for dates and a NEXT STEP line in the fourth.
That's not what I see
Claude added a late fee, interest or "we'll take legal action".
Delete it, and reply: Take that out. Only mention a fee or a next step I've given you from my own terms. A threat you don't mean, or can't back up, can get you into trouble.
Claude suggested telling someone else, like their boss or their neighbors.
Delete it, and write only to the customer. Who you may contact about an unpaid bill depends on local law, so leave everyone else out of it. If the customer is a company, the person who handles its bills counts as the customer.
Have Claude read all four as the customer
A message can read harder than you meant it. This prompt has Claude read the ladder as the person who owes the money, and point out anything that could land badly.
1. Copy the prompt below.
```
Read all four reminders as the customer who owes the money. For each one, tell me anything that sounds rude, like a threat, or like a claim I can't back up, and any fee, deadline or next step I didn't give you. Then suggest one change to each, if it needs one. Don't add anything new.
```
1. Paste it into the same chat and send it.
2. Make the changes you agree with, in your own words.
If a customer says something is wrong with the work or the bill, stop the reminders and sort that out with them first. If a customer writes back angry, the lesson "The hard customer" walks you through a calm reply. If they offer to pay part of it, decide yourself what you'll accept before you answer.
You should see:
A note on each of the four reminders, with anything that reads badly and one suggested change.
That's not what I see
Claude says they're all fine.
Read the fourth one out loud yourself. If you'd be upset to get it from a supplier you'd always paid on time before, soften it.
Have Claude draft a price-increase note
When your costs go up, your prices may have to go up too. Fuel, stock and software all cost more over time. A short, plain note gives regular customers notice. Check your contracts and any terms you've published, because some say how much notice you have to give.
1. Copy the prompt below.
```
Write a short note telling my regular customers my prices are going up. Start with "Hi [Name],". Say what's changing and when, with FILL IN for the old price, the new price and the date it starts. Give one honest reason in a line, with FILL IN for it. Thank them for their business. Don't apologize more than once, don't offer a discount or a delay, and don't add anything I didn't give you. Keep it under 100 words.
```
1. Paste it into the same chat and send it.
2. Fill in the old price, the new price, the date and the reason yourself.
You should see:
A short note that starts with "Hi [Name],", with FILL IN for the old price, the new price, the date and the reason.
That's not what I see
I'm worried customers will leave.
Some might. Tell your best customers yourself, in person or on the phone, before the note goes out. Use the note for everyone else.
Put the reminders and the note on one page
This prompt saves the whole ladder and the price note with the rules at the top, so you're not starting from scratch the next time a bill runs late.
1. Copy the prompt below.
```
Put the four reminders and the price-increase note on one page I can save, numbered in order, keeping every FILL IN, [Name] and NEXT STEP line as blanks. At the top, write these rules: Check the amount and the date against my own records before I send. Polite and factual, every time. No threats. No fee, interest or next step that isn't in my contract. Write only to the customer. Late fees and collections depend on my contract and local law, so I check those, or ask a professional, before I use them. Never paste bank, card or account details into AI.
```
1. Paste it into the same chat and send it.
2. Copy the page into a note or a document called Money messages.
You should see:
One page with the rules at the top, then the four reminders and the price-increase note.
That's not what I see
Nobody has reported a snag on this step yet. Getting stuck is normal. Read the step again one line at a time, and compare your screen with the video.
Set a weekly check on who owes you
Checking once a week means a late bill gets its first reminder while the job is still fresh in everyone's mind.
1. Open the calendar app on your phone or computer.
2. Add a 10-minute reminder that repeats every week, on a quiet morning.
3. Call it Who owes me? Send the next reminder.
That's not what I see
I keep forgetting who's paid.
Keep a short list of open bills in a note or on paper, with the amount and the due date. Cross each one off when it's paid. Your weekly check reads that list.

Your challenge

Look at who owes you money today. If anyone is past the date you agreed, send them your first reminder this week, with the amount and the date checked against your own records. If nobody is, pick the price you most need to raise and fill in your price-increase note, ready for when you decide.

Last checked 2026-10-20

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