I’ve been begging you to switch from ChatGPT to Claude for months.
So I wrote countless Claude guides, getting millions of reactions.
But only recently, everyone *actually* switched:
Claude is all the rage right now because of Cowork: it’s the best thing to happen to AI since ChatGPT. If you don’t code, you must be using Claude Cowork now.
Some of you read my guide in March, and spent an hour setting up Cowork:
That’s a good start.
But you’re using it the way I taught you on March 5.
And a lot has changed since then. This free guide shows you exactly what & how.
Before starting, I want you to do two things:
1. Save this guide & block 20 minutes this week to test Cowork.
1. Send it to anyone who still hasn’t tried Cowork (or Claude).
Skip this if you already use Claude Cowork.
Quick reminder on how to access Claude Cowork:
1. Go to claude.com/download. Download the app on your computer.
1. You must have a Pro account ($20/month). I pay for the $100/month plan.
1. Open the app. Click on the Cowork tab at the top between Chat & Code.
1. Select a folder from your computer. More about it right after this set up.
1. Make sure to always select “Opus 4.6” for complex tasks. It’s the smart model.
I - My Cowork folder (updated).
Claude Cowork is all about how you set up your folder inside your computer.
Because each session on Cowork starts like this:
Here’s how I set this up.
1. Create a new folder on your computer named Claude Cowork.
1. Copy this folder structure: 3 subfolders inside the Claude Cowork.
1. (1) ABOUT ME (2) OUTPUTS (3) TEMPLATES.
Let’s start with the ABOUT ME folder - the most important one.
Step 1: Three core files in the ABOUT ME folder.
These are the only files Cowork reads automatically. The other two folders (OUTPUTS & TEMPLATES) are just here in case you need them for later.
File #1 — about-me
Who you are. How you think. How you want Claude to write for you.
A few months ago, I wrote an extremely long and complex about-me file. I asked Claude to interview me through 100 questions. But that single file was eating 22,000+ words of Cowork’s context window.
In simpler terms, Claude had to read too much before answering.
So I trimmed it to under 2,000 words by extracting the patterns and throwing away the raw transcripts. Almost the same, but 10x less noise.
IF YOU ALREADY HAVE IT, trim it. Here’s how:
1. Go to Claude Cowork. Upload your previous about-me file.
1. Then simply asked Cowork this prompt:
This is my about-me file and I need to save tokens.
Ask me questions on how to trim effectively until we have the perfect document.
NOW IF YOU DON’T HAVE ANY FILE, here’s how to make yours from scratch:
1 - Open a new Cowork session.
2 - Prompt it:
You are building my about-me.md file for my Cowork folder. This file will be read by Claude at the start of every session to help you do my job with me. It needs to be concise and high-signal.
Your job: interview me using AskUserQuestion (20 questions), then compile the answers into a condensed about-me.md under 2,000 tokens.
How to interview me
Use AskUserQuestion for every question. One question at a time. Let me use "Other" to dictate long answers when I need to.
If I give a vague answer, push back. Ask for a specific example or rephrase. Don't accept "I like to keep things clear" without knowing what clear looks like in my work.
Follow interesting threads. If something unexpected comes up, go deeper before moving on.
What to cover (15-20 questions, adapt based on what matters for my role)
WHO I AM (3 questions)
- What do I do? What's my role, my company, my industry?
- Who do I work with or work for? (clients, team, stakeholders, audience)
- What does a good week of work look like for me?
HOW I WORK (4 questions)
- What tools do I use every day and how?
- Walk me through how I start a typical task from zero to done.
- What does my review/editing/QA process look like?
- When I hand something off (to a client, a boss, a reader), what does "done" look like?
WHAT GOOD LOOKS LIKE (4 questions)
- Show me or describe the best output you've produced recently. What made it good?
- What separates great work from average work in your field?
- When you look at someone else's work and think "this is good," what are you reacting to?
- If I had to judge your work, what should I be looking for?
WHAT YOU HATE (4 questions)
- What's an example of bad work in your field? What specifically makes it bad?
- What patterns, shortcuts, or habits in your industry make you cringe?
- When Claude writes something for you and it's wrong, what's usually off? (tone, structure, detail level, assumptions)
YOUR RULES (3 questions)
- What do you never do in your work? Hard lines you won't cross.
- What are the 2-3 non-negotiables that every piece of your work must have?
YOUR OPINIONS (3 questions)
- What do you believe about your field that most of your peers would push back on?
- What tools, methods, or trends do you think are overrated? What's underrated?
Output format
After the interview, compile everything into a single markdown file. Do NOT save raw Q&A transcripts. Extract the patterns from my answers and write them as condensed prose and bullet points.
Structure:
# ABOUT ME: [My Name]
Who I am
[2-3 sentences. My role, my work, my audience/clients. Current facts and numbers if relevant.]
How I work
[My daily tools, my process, how I start tasks, how I review, what "done" looks like. Short paragraphs.]
What good looks like
[What I value in my own work and others'. The standards I hold. Condensed from examples I gave.]
What I hate
[Patterns, shortcuts, and mistakes that bother me. What "wrong" looks like. Specific, not vague.]
My rules
[Numbered list. Hard lines and non-negotiables.]
Instructions for Claude
[10 numbered rules for how to work with me. Derived from everything above. Focus on what Claude must DO and NOT DO, not abstract principles.]
Target: under 2,000 tokens total. Every sentence should carry signal. If a sentence could be cut without losing information, cut it.
Save the file as about-me.md in my ABOUT ME/ folder.
3 - Click where you need to click.
4 - Dictate your answers when you need to say specific things. Make sure to use Wispr Flow instead of typing on your computer. It’s free & much faster.
You will end up with an about-me file that knows exactly you & your style:
File #2 — anti-ai-writing-style
You hate AI writing. I hate AI writing.
You want your taste, as a set of rules. The words you hate. The sentence patterns that make you cringe. The formatting rules you care about.
Mine bans 80+ AI words (delve, harness, tapestry, the usual suspects), kills reframe patterns (”this isn’t X, this is Y”), and limits paragraphs to 3 sentences. I shared the full list in my AI detection newsletter.
You don’t need to copy mine. But you need *something* here. Without it, Claude writes like Claude. With it, Claude writes like you *(minus the parts you hate)*.
If you want to copy my updated file, subscribe to my newsletter, and you will receive it for free as a gift (with tons of other stuff). If you have already subscribed to it, leave a comment on this blog, and I will personally send it to you!
File #3 —my-company
Your targets. Your strategy. What you’re focused on. What you’re saying no to.
Mine has my audience targets per platform (1M Substack subs, 1M LinkedIn followers), my consulting service lines (workshops, full deployment, AI sprints, fractional chief of AI), and a *“what I’m saying no to”* section.
I update it when something actually changes. Maybe once a quarter. Cowork doesn’t need to know your Tuesday deadline. It needs to know your north star.
Go to Claude Cowork, not a new session, but the same one you used for about-me *(just keep prompting after)*, and paste this:
You are building my my-company.md file for my Cowork folder. This file tells Claude what I'm working toward right now so it can make better decisions on every task.
Important: my about-me.md already covers who I am, how I work, and my standards. This file is ONLY about goals, strategy, and decisions. No overlap.
Your job: interview me using AskUserQuestion (6-8 questions), then compile the answers into a condensed my-company.md under 1,000 tokens.
How to interview me
Use AskUserQuestion for every question. One question at a time. Let me use "Other" to dictate long answers when I need to.
What to cover (6-8 questions)
GOALS (3-4 questions)
- What are your top 2-3 goals for this year? Specific numbers or milestones.
- What platforms, channels, or markets matter most right now?
- What's the one metric that would tell you this year was a success?
- Do you have revenue targets, audience targets, or product milestones? What are they?
DECISIONS (3-4 questions)
- What are you actively saying no to right now? (opportunities, trends, platforms, tactics)
- What did you recently stop doing? Why?
- Where are you spending most of your time and energy this quarter?
- Is there anything you're betting on that most people in your field aren't?
Output format
After the interview, compile everything into a single markdown file. Short sections, mostly bullet points. No filler. No identity info (that's in about-me.md).
Structure:
# MY COMPANY
Goals
[Bullet points. Specific targets with numbers where possible. Organized by category if needed.]
Focus right now
[What I'm spending time and energy on this quarter. 2-3 bullet points max.]
Saying no to
[Bullet points. Things I'm actively declining or ignoring.]
Target: under 1,000 tokens. Update this file when priorities change, not on a schedule.
Save the file as my-company.md in my ABOUT ME/ folder.
This file looks very different if you are a lawyer, a nurse, or a plumber.
Step 2: The OUTPUTS folder for Claude’s work.
This is simply where Cowork will work and save his document.
One subfolder per project. Cowork organizes everything itself. It never reads from this folder on its own *(that would eat your token budget = you save money).*
But when you need to reference a past deliverable, you just say:
“Read the report in OUTPUTS/project-name.”
Step 3: The TEMPLATES folder for Claude’s best work.
Cowork fills this folder automatically *(more on that in a second)*.
You don’t maintain it. You don’t organize it. You just point Claude to a specific template when you want to reuse a structure.
How? Thanks to *(better)* Global Instructions.
II - How to set up Global instructions.
Your folder is not as good without global instructions.
Global Instructions is a prompt that Claude Cowork always read before any task. I use it to explain how my folders work.
Claude Cowork doesn’t know what your files mean or when to read them unless you tell it. So go to: Settings → Cowork → Edit Global Instructions.
Paste this and change the file descriptions to match yours:
Before every task, read every file in ABOUT ME/:
- about-me: [describe what's in yours: your role, how you work, your standards]
- anti-ai-writing-style: [describe what's in yours: your writing rules, banned patterns, formatting preferences]
- my-company: [describe what's in yours: your goals, strategy, what you're focused on]
Never read OUTPUTS/ or TEMPLATES/ unless I specifically point you to a file.
Save all deliverables in OUTPUTS/ under a subfolder named after the project.
If the brief is unclear, use AskUserQuestion. Don't fill gaps with filler. Don't over-explain. Deliver the work.
Why this matters: Cowork reads your ABOUT ME files before every single task. If those 3 files are small (under 6,000 tokens total), it reads all of them completely. Every session. You never re-explain who you are or what you’re working on.
If your files are too big, Cowork starts summarizing them loosely instead of reading them carefully. Keep the files lean. The context window is for your actual task, not for your profile.
How templates work with global instructions.
The TEMPLATES folder doesn’t fill itself. When Cowork builds something you like (a report, an email, a brief), you say one sentence at the end of your session:
*“Save this as a template in TEMPLATES/.”*
Claude strips the content, keeps the skeleton (sections, order, format, length), and saves it. Next time you need something similar, you say “use the template in TEMPLATES/[name of the file]” and Cowork follows the structure.
I feel like you’re starting to understand how effective Claude Cowork is.
Actually, it’s so effective that the bottleneck is not the technology… but you.
III - Your Cowork has a bottleneck. It’s you.
This is a typical Cowork session:
1. You type a prompt. 30 seconds.
1. Cowork reads your files. 5 seconds. It generates a plan. 20 seconds. It asks you clarifying questions using AskUserQuestion. 5 seconds.
1. Now you answer those questions. You click some options. Fine.
But sometimes you need to type a custom answer (and custom answers are where the best outputs come from). So you stop. Think. Type.
60 seconds per answer. Maybe 2 minutes.
Across 8 questions, that’s 8-15 minutes of *you* being the slow part.
But Cowork can read 100,000 words in 15 seconds. It can build a spreadsheet in 90 seconds. And it has to wait for you to type at 60 words per minute.
But you could be faster. Because you speak at 150 words per minute.
Side note ⚠️ I know it sounds ridiculous to optimizing everything for speed. But talking instead of typing has another massive benefit: it sounds natural. It’s you, your voice. And your brain thinks very differently when it has to talk.
Did you realize how good your ideas are, your flow is, when you’re talking to a colleague about solving a problem? We want the same flow state here.
How to set up Wispr flow.
Quick reminder for those who missed it: Wispr Flow is a dictation tool. You hold a key, talk, release. Your words appear wherever your cursor is.
Anywhere on your computer. Including inside Cowork’s chat box.
What makes Wispr Flow different: its accuracy.
Near perfection, every single time.
Wispr Flow + Claude Cowork is the perfect match to counter a common problem when using AI: you steer the conversation, and make sure you are in flow state.
Instead of typing *“I need a Linkedin post,”* you start talking *“I recently found out about… and I want to share more about… but first I need to make sure that… so maybe we should start covering… and end up with… as a conclusion”.*
1. The initial prompt: I speak it.
I say this out loud. Wispr types it.
The point isn’t to be faster, but we end up giving much more context when we talk (we are yappers by nature), rather than with a lazy typed prompt.
And the more context, the better.
2. AskUserQuestion answers: I speak those too.
Cowork generates a form. Most options I just click.
But when I need to add context (*”make it more direct, she’s a CEO who hates fluff, and reference the ROI data from the last call”*), I dictate that instead of typing it.
I don’t self-edit while speaking. I dump my thinking.
Cowork figures out what matters.
3. Feedback and pivots: spoken.
When Cowork produces something that’s off, I used to type feedback like: *“Tone is wrong. Make it less formal.”*
Now I say: *“The tone is too stiff. I want it to sound like I’m texting a friend who happens to run a 200-person company. Keep the data but make it casual. Only redo section 2.”*
Spoken feedback is richer because I am a yapper.
How to download Wispr Flow for free.
1. Go to wispr.ai. Download Wispr Flow. Install it.
1. The free tier is capped at 2,000 words/week - perfect to know if you like it.
1. Choose your favorite keystroke to activate Wispr Flow. I personally love “Shift”, the little arrow below “Enter”.
1. Go to any app, hold your keystroke (like shift) and… talk.
1. You now type 4x faster than before. Congratulations.
1. You get a free month when you pay for my newsletter* (you don’t have to).*
There’s no “integration” to configure. Wispr types wherever you type.
IV - How to save credits in Cowork.
The $20 paid plan of Claude will give you credits (called tokens).
But you will use them up very fast.
At the scale of a company, saving tokens = saving thousands of dollars!
This section is about saving as many credits (= tokens) as possible.
1 - Restart your conversation. Don’t send a follow-up.
First, Claude doesn’t count messages. It counts tokens. Every time you send a message, Claude re-reads the entire conversation history.
Message 30 costs 31x more tokens than message 1.
When Cowork gets something wrong, you want to type *“No, I meant...”* and send another message. Don’t.
Every follow-up stacks on top of the full conversation history. Claude re-reads all of it every turn. At ~500 tokens per exchange, 20 messages burns 105K tokens. 30 messages burns 232K.
Instead: click “Restart the conversation from here” on a previous message (much higher ideally so you do save tokens).
In Cowork you can’t edit a previous message. So when something goes wrong early, start a new session with a better prompt or restart the conversation higher.
It’s the biggest hack!
2 - Start a fresh session every 20 messages.
Long conversations are token furnaces.
One developer tracked his usage and found 98.5% of tokens were spent re-reading history. Only 1.5% went to the actual output.
When a Cowork session gets long: ask Claude to summarize everything, copy it, start a new session, paste the summary as your first message.
You keep the context. You lose the bloat.
3 - Batch your tasks into one message.
Three separate prompts = three full context reloads.
One prompt with three tasks = one reload.
Instead of: *“Summarize this article”* then *“List the main points”* then *“Suggest a headline” *write: *“Summarize this article, list the main points, and suggest a headline.”*
4 - Use Sonnet (not Opus) for quick tasks.
Grammar checks, brainstorming, formatting, short answers. Sonet handles all of this at a fraction of the cost. And technically, Haiku is even cheaper.
Save Opus + Extended thinking for the work that actually needs it. Drafts and simple tasks on Sonnet-Haiku free up 30-70% of your budget for deep work.
5 - Keep your ABOUT ME files small.
Cowork reads your folder before every single task. If your files are bloated, that’s thousands of tokens burned before any real work starts.
My about-me.md used to be 22,000 tokens. Now it’s under 2,000.
That’s kind of the point of this entire newsletter. Please do it :)
6 - Spread your work across the day.
This one is impossible to actually do in practice, but it works.
Claude uses a rolling 5-hour window. If you burn your entire limit in one morning session, most of your daily capacity goes unused.
Split into 2-3 sessions: morning, afternoon, evening. By the time you come back, your previous usage has rolled off. And avoid peak hours (5-11 AM Pacific on weekdays) when the same query costs more against your limit.
Cool in theory, but I never do it ahah. If I want to work, I work. That’s why I pay for the $100/month paid plan. So far, no problem (but a lot on the $20 plan).
V - Your first 20 minutes with Claude Cowork.
You read this newsletter, and want the quick and easy setup in 20 minutes.
Open your calendar. Block 20 minutes this week.
Bonus point: book a meeting with your team to do it together!
Minutes 0-5: Set up the folder.
Download the Claude desktop app (duh!) and get the paid plan ($20 or $100).
Create the folder structure on your computer from this newsletter. ABOUT ME/ with your 3 files, plus empty OUTPUTS/ and TEMPLATES/ folders.
For your about-me file: open a Cowork session, ask it to interview you, dictate your answers. Then ask it to condense everything to under 2 pages.
For your anti-ai-writing-style file: write the words and patterns you hate. Or start with mine from the detection newsletter. Or subscribe for free to my newsletter, I will send you all of my own files as a gift!
For your my-company file: your targets, your platforms, your strategy. What you’re saying no to. Keep it short.
Minutes 5-6: Paste the global instructions.
Go to Settings > Cowork > Edit Global Instructions. Delete whatever’s there.
Paste the version from this newsletter. Adjust the file names if yours are different.
Minutes 6-8: Install Wispr Flow.
Go to wispr.ai. Download. Install. Select your favorite keystroke.
When you use the keystroke and release, you can talk and it types.
Now open Cowork. Start a new task. Test Wispr Flow there. It works!
Minutes 8-15: Run your first voice session.
Open Cowork. Speak a task: *“I want you to read my folder and help me write [something you actually need this week]. Ask me questions before you start.”*
Answer the questions by speaking. Let Cowork build it. Review the output.
You’ll feel the difference in the first 3 minutes.
Minutes 15-20: Feel comfortable with your folder.
Ask Cowork to create a template inside the TEMPLATE folder from the conversation you just had. Now go on your computer’s folder, and check all of the subfolders (so you feel comfortable):
1. ABOUT ME is all of your files that explain who you are.
1. OUTPUTS is just for Cowork outputs. Check it just to feel it.
1. TEMPLATES is where the templates are saved. You can use them anytime.
You are a Claude Cowork pro now! in 20 minutes.
A message from the author, Ruben.
This article exists because 50,000+ people decided AI is too important to leave aside. Not only that, but they shared it around them. They understand they are the sum of the 5 people around them. So better have them using AI.
If this helped you — or if it’ll help someone you know — forward it to them. That’s how this grew. Just readers like you sending it to people like them.
And if you're new here, follow me on X →@rubenhassid (also free!)
