Is my AI paying for itself?
⏱ 40 min6 steps
tools cost little to start and keep billing long after anyone stops using them. That's how a business ends up paying for two that do the same job. You'll put every AI tool and on one sheet, with what it does, how often it runs and what it costs from your own bills. Then each one gets a : a question you answer before it bills again. Hunting down every charge is the slow part, and it takes longer than people think.
AI Short for artificial intelligence. Here it means a program like Claude that reads what you write and writes back in plain words. All wordsagent Claude given a goal and some tools. It plans, does a step, checks the result and keeps going until the job is done. All wordsrenewal test One yes-or-no question you write when you start paying for something, and answer before it renews, to decide whether it stays. All wordsBefore this, you'll want:
Steps
Gather every AI bill and every agent
Costs come only from your own bills. Never paste card numbers, account numbers or a full statement into a chat.
Look in three places. Last month's from "Where did the money go this month?", if you've done it. Your email, searching for receipt, invoice, and AI. And your agent review sheet from "Did it actually run?", for agents that run inside software you already pay for.
A contractor might find a quoting tool and an AI phone answerer. A store might find a product description writer and a chatbot on its website. An office might find a meeting note-taker, and a one-person service might find two chat assistants that do the same thing.
- Write each one on its own line: its name, what it does, how often it runs or you use it, and what you used it for last month.
- Add the amount and how often it bills, typed from the bill itself. If you can't find the bill, write FILL IN.
- If the bill shows a renewal date or says yearly, annual, renewal, subscription or plan, copy those words onto the line.
That's not what I see
- I'm not sure whether something counts as AI.
- Put it on the list. If its bill or its website says AI, assistant, agent, smart or automated, it counts for this review. You can take it off later.
- Some of these are on my personal card.
- Put the ones you use for the business on the list, and leave the personal ones out.
Start a new chat and build the AI spend review
This turns your list into one table. It uses only what you typed, and puts FILL IN anywhere you didn't give it an amount.
AI drafts and sorts; a person approves anything with a price, a date or your name on it. Claude lays out the table. You check every amount against the bill.
- Open the or claude.ai and start a new chat.
- Copy the prompt below.
I run a small business, [what you do]. Below is my typed list of every AI tool, subscription and agent I pay for or use, from my own bills and my agent review sheet. Make an AI spend review as a table with these columns: name, what it does, how often it runs or I use it, what I used it for last month, cost each time it bills, how often it bills, cost per month, renews, and renewal test. Use only my list. Don't look up any prices, and don't guess any amount. If a cost or anything else is missing, write FILL IN. Work out cost per month only from what I gave you, and show the sum. Fill in renews only where my list quotes a date or the words yearly, annual, renewal, subscription or plan, and quote them. Give a date only if my list shows one. If a line only looks like it might repeat, write Might repeat, and don't say when. Leave renewal test empty. Don't tell me what to cancel. I decide. My list: [paste your list]
- Paste it into the chat. Replace the parts in square brackets with what you do and your list from Step 1.
- Send it.
- Check three amounts in the table against the bills.
You should see:
A table with one row for each tool or agent, FILL IN where your list had no amount, and the renewal test column empty.
That's not what I see
- Claude filled in a price I didn't give it.
- Reply: Use only my list. Put FILL IN where I gave no amount. Then check the rest of the table again.
Write a renewal test for each line
A renewal test is a question you write now and answer later, so the decision isn't made in a hurry after a renewal email. This prompt drafts one for each line. You choose the numbers.
- Copy the prompt below.
For each line in the table, help me write a renewal test: one yes-or-no question I can answer on the day it renews, about what it did for my business. Base each one only on what I said it does and what I used it for. Put FILL IN where a number belongs, like how many times I used it or how many hours it saved, and I'll choose the number. Don't suggest a number yourself. Add the tests to the renewal test column and give me the whole table again.
- Paste it into the same chat and send it.
- Replace each FILL IN with a number you'd be happy to be held to.
- Change any test that doesn't sound like you.
You should see:
The same table with a yes-or-no question in the renewal test column for each line, with FILL IN where a number goes.
That's not what I see
- The tests are vague, like "Was it useful?"
- Reply: Make each test something I could check, like a count of times I used it. Then fill in the numbers yourself.
Check the totals
This prompt adds up the month and the year, with the sums written out, and lists anything left out.
- Copy the prompt below.
Give me the total cost per month and the total cost per year for everything in the table, and show every sum. Leave out any line whose cost is FILL IN, and list those lines under the totals so I know what's missing.
- Paste it into the same chat and send it.
- Add the monthly amounts from your bills on a calculator and compare.
You should see:
A monthly and a yearly total with the sums written out, and a list of lines left out because they had no amount.
That's not what I see
- Claude's total doesn't match mine.
- Add the amounts on a calculator from your own bills. Use yours, and check whether Claude read one amount wrong.
Answer each renewal test and decide
- Go down the table and answer each renewal test yes or no, from your agent review sheet and your own memory of the month.
- Write keep next to each yes. For each no, write cut or one more month, with the date you'll decide again.
- Cancel anything you cut yourself, in the company's own account or by calling them. Claude doesn't cancel anything.
- Write the date next to each one you cancel, so next month's ledger can show it stopped.
That's not what I see
- It's a yearly plan, and the renewal is months away.
- Answer the test today anyway, and again a week before the renewal date on the bill. If you don't know the date, find it in the company's own account settings, yourself.
Save the review and set reminders
This prompt puts the table, the prompts and the rules on one page you can keep.
- Copy the prompt below.
Put the table and the prompts from this chat on one page I can save, called AI spend review, with blanks in square brackets for what I paste. At the top, write these rules: Costs come only from my own bills. Claude never looks up or guesses a price. Every AI tool and agent gets a renewal test on the day I start it. No renewal date unless the bill shows one. Claude never cancels anything or contacts any company. I decide, and I check the totals on a calculator.
- Paste it into the same chat and send it.
- Copy the page into a note or a document called AI spend review.
- In your calendar, add a reminder a week before each renewal date the bills show. Call it Renewal test: and the tool's name.
- Add a 30-minute reminder every three months, called AI spend review.
You should see:
One page with the rules at the top, then the table and the prompts with blanks in square brackets.
That's not what I see
- The page looks messy when I paste it.
- Ask Claude for it as plain text, with a blank line between sections. Then copy it again.
Your challenge
Build your AI spend review this week from your own bills, and write a renewal test for every line. Before you sign up for anything new with AI in it, write its renewal test first, on the day you start.
Last checked 2026-10-20
Weekly helpers, in the app
Is my AI paying for itself?
One-page card · print it or keep it open
What you'll do
AI tools cost little to start and keep billing long after anyone stops using them. That's how a business ends up paying for two that do the same job.
The steps
- Gather every AI bill and every agent
- Start a new chat and build the AI spend review
I run a small business, [what you do]. Below is my typed list of every AI tool, subscription and agent I pay for or use, from my own bills and my agent review sheet. Make an AI spend review as a table with these columns: name, what it does, how often it runs or I use it, what I used it for last month, cost each time it bills, how often it bills, cost per month, renews, and renewal test. Use only my list. Don't look up any prices, and don't guess any amount. If a cost or anything else is missing, write FILL IN. Work out cost per month only from what I gave you, and show the sum. Fill in renews only where my list quotes a date or the words yearly, annual, renewal, subscription or plan, and quote them. Give a date only if my list shows one. If a line only looks like it might repeat, write Might repeat, and don't say when. Leave renewal test empty. Don't tell me what to cancel. I decide. My list: [paste your list]
- Write a renewal test for each line
For each line in the table, help me write a renewal test: one yes-or-no question I can answer on the day it renews, about what it did for my business. Base each one only on what I said it does and what I used it for. Put FILL IN where a number belongs, like how many times I used it or how many hours it saved, and I'll choose the number. Don't suggest a number yourself. Add the tests to the renewal test column and give me the whole table again.
- Check the totals
Give me the total cost per month and the total cost per year for everything in the table, and show every sum. Leave out any line whose cost is FILL IN, and list those lines under the totals so I know what's missing.
- Answer each renewal test and decide
- Save the review and set reminders
Put the table and the prompts from this chat on one page I can save, called AI spend review, with blanks in square brackets for what I paste. At the top, write these rules: Costs come only from my own bills. Claude never looks up or guesses a price. Every AI tool and agent gets a renewal test on the day I start it. No renewal date unless the bill shows one. Claude never cancels anything or contacts any company. I decide, and I check the totals on a calculator.
If it goes wrong
- I'm not sure whether something counts as AI. Put it on the list. If its bill or its website says AI, assistant, agent, smart or automated, it counts for this review. You can take it off later.
- Claude filled in a price I didn't give it. Reply: Use only my list. Put FILL IN where I gave no amount. Then check the rest of the table again.
- The tests are vague, like "Was it useful?" Reply: Make each test something I could check, like a count of times I used it. Then fill in the numbers yourself.
- Claude's total doesn't match mine. Add the amounts on a calculator from your own bills. Use yours, and check whether Claude read one amount wrong.
Words
- renewal test: One yes-or-no question you write when you start paying for something, and answer before it renews, to decide whether it stays.