Five files that teach Claude your business

The idea comes from Anthropic's own prompting guide: treat Claude like a new employee who lacks context. You end up with plain text files in one folder (the .md ending means plain text): five core files, up to four extras, and CLAUDE.md, which ties them together. A session is one conversation in Claude.

5

core context files

4

extras at most

45 to 60 min

start to finish

CLAUDE.md is the file Claude reads at the start of every session (memory docs). Each line that starts with @ tells Claude to open another file too, so everything loads together and you never paste anything in. Keep it short, with your top three rules in it. Think of it as the first page of the onboarding binder.

DiagramHow CLAUDE.md links your files

1You open a new sessionIn your business folder

2Claude reads CLAUDE.md firstEvery session, on its own

3It follows each @ lineand reads every linked file too

4It answers with your context

Your business folder

CLAUDE.md

Your top 3 rules

1. Use my customers’ words
2. Never invent a fact
3. Ask before anything is sent

Links@context/you.md@context/business.md@context/customers.md@context/strategy.md@context/brand.md+ one @ line per extra

context/

you.md

business.md

customers.md

strategy.md

brand.mdIncludes the AI words you ban

Extras, only if you need them OptionalUp to 4, such as offers.md or faq.md

1. You open a new session in your business folder.
2. Claude reads CLAUDE.md first.
3. CLAUDE.md holds your top three rules and one @ line per file, for example @context/you.md.
4. Claude follows each @ line and reads the five core files in the context folder, plus up to four extras if your business needs them.
5. brand.md includes the words you ban, such as the ones that make text sound AI-written.
6. It answers with your context.

Extras your business may need

After a few basic questions, Claude proposes at most 4 extras. Each comes with a reason, and you approve them. Every linked file loads every session, so the cap keeps things light.

What you need

• A paid Claude plan. Claude Code requires a Pro, Max, Team or Enterprise subscription. Free is excluded (pricing). As of September 2026.
• A Mac or Windows computer, and 45 to 60 minutes. The interview takes most of it.

No paid plan? Use the Claude Project route near the end.

Claude Code is the part of Claude that can read and write files on your computer. I recommend the desktop app. Anthropic keeps adding features to it, so it's worth learning. It includes Claude Code, so you don't need Node.js or the command line tool (desktop quickstart).

1. 1

   Go to claude.com and choose the Mac or Windows version.

2. 2

   Install the app and sign in with your paid account.

Screenshot · Oct 2026

Download the desktop app for Mac or Windows

3. 3

   Click the Code tab at the top centre of the app.

   You should see the Code screen.

Claude asks. You click or type short answers.

1. 1

   In Finder or File Explorer, create an empty folder in Documents. Name it after your business.

   It has to exist before you pick it in step 3.

2. 2

   In the Code tab, choose Local. Local means Claude works on files on your own computer (desktop quickstart).

3. 3

   Click Select folder and pick the folder you just made.

   You are now in a blank session that works inside that folder.

Illustration · as of Oct 2026

4. 4

   Set the mode next to the send button to Manual.

   Manual makes Claude ask before it edits a file (desktop docs).

The interview prompt

1. 1

   Paste the prompt and send it.

   You should see a few basic questions with answer choices.

2. 2

   Click or type your answers.

Illustration · as of Oct 2026

3. 3

   Answer the numbered follow-ups in your own words. Short answers are fine.

4. 4

   Paste a customer's sentence, and one or two emails or posts you wrote, when Claude asks.

5. 5

   Read the summary Claude plays back.

   You should see what it understood, what is unclear, and the files it will write.

6. 6

   Correct anything wrong, then type yes.

   Claude writes nothing before your yes.

Short on time? Type "enough, write it". Claude shows what it has, with the gaps marked (check).

After your yes, Claude writes the files and CLAUDE.md. In Manual mode, you approve each one. That is a quick second check.

1. 1

   Read each change Claude shows, then click Accept. CLAUDE.md comes last.

   You see the text Claude wants to write, with Accept and Reject buttons.

Illustration · as of Oct 2026

2. 2

   Open your business folder in Finder or File Explorer, then open the context folder.

   You should see CLAUDE.md beside the context folder, which holds your five core files plus any extras you approved.

Screenshot · Oct 2026

The context folder with your files, CLAUDE.md beside it

3. 3

   Double-click each file and read it. If your computer asks which app to use, pick Notepad (Windows) or TextEdit (Mac).

4. 4

   Tell Claude the right answer for every line marked (check).

5. 5

   Click Accept on each update.

6. 6

   Open CLAUDE.md.

   You should see your three rules, then one line per file, each starting with @.

Screenshot · Oct 2026

CLAUDE.md with three rules and plain @ lines

What the finished files look like

Here is one finished file, for a made-up studio that builds websites for dental clinics.

# Customers

- Who they are: owners of dental clinics.
- Who signs: the owner, often after asking the office manager.
- What they say:
  - "My front desk is drowning."
  - "Patients can't book online."
  - "Our site looks like it is from 2015."
- Words they use: patients (never "leads"), booking, front desk.
- What makes them say no: a timeline that feels long, a quote with no fixed price.
- Where they come from: referrals from other clinic owners (check)

brand.md also holds your ban list. Claude starts it with words that make text sound AI-written.

# Brand

- Voice: plain, warm, direct.
- Never sounds like: a corporate press release.
- Sign-off: "Talk soon," then my first name.

## Words I never use
delve, tapestry, landscape, realm, journey, unlock, unleash, leverage, seamless, elevate, robust, streamline, game-changer, cutting-edge, navigate

## Phrases I never use
"dive into", "in today's fast-paced world", "it's important to note", "I hope this finds you well"

## Patterns I never use
Em dashes. "It's not X, it's Y."

This is a starting point. Paste a paragraph from any AI text that made you cringe, and ask Claude to add five more words from it.

# Dental web studio

## My top three rules
1. Use my customers' words from customers.md. Never use a word from the "Words I never use" list in brand.md.
2. Never invent a fact, price or client. If you are unsure, write (check).
3. Ask me before anything is sent, posted or published.

Read these files before every task.

@context/you.md
@context/business.md
@context/customers.md
@context/strategy.md
@context/brand.md
@context/offers.md
@context/faq.md

1. 1

   Close the interview session.

2. 2

   Start a new session in the Code tab.

3. 3

   Choose Local, then Select folder, and pick the same folder.

4. 4

   Paste the test task below and send it. Give Claude nothing else. No notes, no attachments.

DiagramWhat the test tells you

1The test requestA short post to your customers about this quarter

No other info

2Claude writes the postUsing only your five files

3Two checks

Sounds like you?Uses your customers’ words?

Both yes

Your files work

Either no

Fix the thinnest filethen test again

1. Ask Claude for a short post to your customers about this quarter, with no other info.
2. Claude writes it using only your five files.
3. Check two things: does it sound like you, and does it use your customers' words.
4. Both yes: your files work. Either no: fix the thinnest file and test again.

Judge the post with this checklist. Pass means every box ticks.

Illustration · as of Oct 2026

If a box stays empty, fix the file behind it.

What went wrong	Fix this
Sounds generic	brand.md:addtwomorerealwritingsamples
Wrong customer words	customers.md:pasteexactphrasescustomerswrote
Wrong goal	strategy.md:rewritethisquarter'sgoals(redo it each quarter)
A banned word slipped in	brand.md:additto"WordsIneveruse"
Invented details	Tell Claude which line is wrong and what is true. Ask it to fix the file
Claude knows nothing about your business	Check the @ lines in CLAUDE.md: each on its own line, no backticks or quotes. Start a new session and test again

Claude Code is my pick. No paid plan? Use a Claude Project. Projects work on Free too, up to five of them. A Project has no CLAUDE.md, so your three rules go in the project instructions and you upload every file.

1. 1

   Open a normal chat at claude.ai and paste the interview prompt from "The interview prompt".

2. 2

   Paste the extra line below at the end of the prompt, then send.

3. 3

   Answer the questions.

   You should get a text block for each file, plus one for the project instructions.

4. 4

   Open Notepad (Windows) or TextEdit (Mac: Format, then Make Plain Text).

5. 5

   Paste the first file block, then click Save.

6. 6

   Name it you.md. In Notepad, set Save as type to All files first. On a Mac, if TextEdit asks, choose Use .md.

7. 7

   Repeat for each other file block, using its file name.

8. 8

   Go to claude.ai/projects and click + New Project (Anthropic help).

9. 9

   Click Set project instructions and paste the project instructions block.

10. 10

    Click + and upload every file.

Illustration · as of Oct 2026

Open a new chat inside the project and run the test task from "Test it in a new session".

A skill is a saved set of instructions Claude follows when you type its name. This one, grill-me, questions a plan or decision one question at a time and gives its own recommended answer to each. Use it before you launch an offer, change how you work, or make a hire. In the Code tab it also saves your decisions to decisions.md in your folder. I adapted it from Matt Pocock's skills (Copyright (c) 2026 Matt Pocock, MIT license).

---
name: grill-me
description: Interview me about a plan or decision, one question at a time, with your recommended answer for each, and save the decisions to decisions.md.
disable-model-invocation: true
---

# Grill me

Adapted from grill-me by Matt Pocock. Copyright (c) 2026 Matt Pocock. MIT License: https://github.com/mattpocock/skills/blob/main/LICENSE

Interview me about the plan or decision I give you until we both understand it fully. Look for gaps, hidden assumptions and choices that depend on each other. Settle them one at a time.

- Ask one question at a time. Wait for my answer before the next one.
- Give your recommended answer with every question, so I can just agree.
- If the files in this folder can answer a question, read them instead of asking me.
- There is no fixed number of questions. Keep going until the plan holds up.

After each answer, add the decision to decisions.md in this folder. Create the file on the first decision, with a one-line header: the topic and today's date. Then add one entry per decision: the question, what we decided, and a short reason. If you cannot save files here, show the log in the chat instead.

When we finish, show me decisions.md and ask if anything needs changing.

In the Code tab:

1. 1

   Copy the file above, paste it into a message, and add: Save this as a skill at .claude/skills/grill-me/SKILL.md in this folder.

2. 2

   Click Accept when Claude shows the new file.

3. 3

   Start a new session in the same folder. A new skill may not show up until then.

4. 4

   Type /grill-me, then describe your plan.

   You should see Claude ask one question, with its recommended answer.

In a normal chat: paste the file above, then your plan, and say: Follow these instructions on my plan. Claude shows the decisions log in the chat instead of saving it.