Cowork Mondays: Zero to Claude Cowork in Six Weeks
The full 6-week playbook for getting Claude Cowork running in your business.
I run two companies. This year, I’m putting the majority of our office staff on Claude Cowork. Not as a pilot. As the way we work.
Our TBS estimator has already won back two hours a day. He used to spend the first part of every morning manually wading through bid request emails and loading them into Trello and Salesforce. Now, an AI assistant does intake overnight. He shows up, drinks coffee, and makes one call: bid or pass.
Two hours a day. For one of the most pivotal roles in our company. Saved by a workflow we built in about three weeks.
If you missed last Saturday’s piece on the why behind this bet, it’s right here. Today’s piece is the playbook. The actual six weeks. Click by click.
Quick note on the format. This piece is free, public, and yours. Read the playbook at your own pace. The reason to subscribe (free, just a few clicks) is so the Monday cohort emails land in your inbox starting May 18, where I’ll share my how-to videos and the real-time lessons from running this same playbook at CRATE and TBS.
The cohort kicks off Monday, May 18. Every Monday through June 22, you’ll get a short email from me with that week’s check-in video and a quick note on what’s working in our offices and what I’m hearing from readers running the playbook alongside us. No chasing the content. It lands in your inbox. You can follow at your own pace, but the cohort is just more fun.
Starting point: you’ve poked at ChatGPT a few times, or maybe used Claude in a browser tab once or twice. That’s where we begin.
Week 1: Set the Foundation
Goal: Stop treating AI like a search engine. Start treating it like a workspace.
A quick word on the why. Fair question coming: “Couldn’t I just do this inside Claude’s browser chat?” Yes. But the whole point of Cowork is that it can *do* things, not just talk. It reads real files on your computer, creates new ones, saves them where you tell it, and references them next week. Chat gives you words on a screen. Cowork gives you working files. Week 1 is built to make that difference click.
Do this:
1. Go to claude.ai and sign up for Claude Pro or Claude Max. Pro is plenty to start. Max is for when you’re hooked.
2. Download the Claude desktop app from claude.ai/download. Install it on your work computer.
3. Open the app and switch on Cowork mode.
4. Create a folder on your computer called “Cowork” and connect it inside the app.
5. Drop one document you’ve been meaning to read into the folder.
6. In the Cowork chat, type: “Summarize this document in plain English. Save the summary as a PDF in this same folder.”
7. Open your folder on your computer. The PDF is sitting right there. Open it. Read it.
8. Back in Cowork, type: “Now rewrite that summary in a casual tone, like you’re telling me at lunch. Save it as a separate file in the same folder.”
9. Check the folder again. Two real files where there used to be none.
Friday’s win: You’ve created actual, useful files on your computer using nothing but plain English. The browser tab can’t do that. This is the unlock that everything else in the program builds on.
Week 2: Teach Claude Who You Are
Goal: Stop getting generic answers. Start getting answers that sound like you, automatically, every session.
Do this:
1. Open Cowork. Type: “Draft a quick email politely declining a vendor proposal.” Read what comes back. It’ll be fine. It’ll also sound like a generic LinkedIn post. That’s your baseline.
2. Build your Personal Preferences doc. Two ways to do this. Pick one.
Option A (recommended): Let Claude interview you. In your Cowork chat, paste this prompt:
> “You are an interviewer helping me build a Personal Preferences document for Claude. Ask me one question at a time. Wait for my answer before moving on. Don’t bundle questions. Cover these areas in order: name and title; my company or companies; the people in my life (spouse, kids, key colleagues by name); my daily role and focus; my communication style (length, formatting, tone); words and phrases I can’t stand; punctuation rules (em dashes, emojis, bullet points); personal goals or values that should shape your advice; how I want you to respond when I’m wrong or making excuses; anything else important about me. After all questions are answered, save the result as a file called ‘Personal Preferences.md’ in this folder. Use clear section headers. Don’t editorialize. Just structure my answers. Ask me question 1.”
Answer the questions one at a time. When the interview wraps, Claude saves the finished doc into your Cowork folder.
Option B (DIY): Write it yourself. Open a blank Google Doc. Write down your name and role, your people, your communication style, the words and phrases you can’t stand, and how you want Claude to respond to you. Save it as “Personal Preferences” in your Cowork folder.
3. Install it in two places so Claude uses it automatically:
- Claude account settings (Settings > Profile): paste in the basics, name, role, and communication style. Applies across every Claude product you use.
- Cowork Global Instructions (Settings > Cowork > Global Instructions): paste in the full document. Loads automatically every time Cowork fires up.
4. Restart Cowork.
5. Type the exact same question from step 1: “Draft a quick email politely declining a vendor proposal.”
6. Compare the two responses side by side. The first one is who Claude is to everyone. The second one is who Claude is to you.
Friday’s win: Claude sounds like you automatically, every session, without being asked. This is the foundation that everything else in the program rides on top of.
Week 3: Connect Your World
Goal: Stop copy-and-pasting. Start letting Claude actually read AND act on your business.
A quick note on why this week matters. Connecting your tools is the moment Cowork goes from “neat AI helper” to “actual coworker.” It can read your inbox, scan your calendar, search your Drive, and now create things on your behalf. This week is the unlock that makes Weeks 4 and 5 possible.
Do this:
1. In the Cowork app, open Settings > Connectors.
2. Connect your email. Gmail or Outlook, whichever you use.
3. Connect your calendar. Google Calendar or Outlook Calendar.
4. Connect your file storage. Google Drive, OneDrive, SharePoint, Box, Dropbox, whatever holds your documents.
5. Connect one more tool you live in. Common picks for operators: HubSpot, Asana, ClickUp, Monday.com, Notion, Slack, Teams.
6. Test the read side. Try these three prompts:
- “What’s on my calendar tomorrow?”
- “Find the last proposal I sent to [client name].”
- “Summarize the last five emails from [team member].”
7. Now test the write side. This one needs a quick setup first. Go back to Settings > Connectors, find your calendar connector, and turn on write permissions. Most calendar connectors default to read-only, so you have to explicitly enable Cowork to create events on your behalf. Once write access is on, head back to the Cowork chat and type: “Create a calendar event on my calendar for next Tuesday at 2:00 pm called ‘Test Cowork Event’ for 30 minutes.” Now open your calendar. There it is. That’s the difference between Claude reading your world and Claude working in your world.
Friday’s win: Claude can see your work AND act on it. This is the moment most people I’ve coached say “oh, now I get it.”
Week 4: Build Your Morning Briefing
Goal: Replace 30 to 60 minutes of morning inbox triage with a single page that’s ready before you open your laptop.
A quick note on why this week. Last week, you connected your tools. This week, you put them to work. The morning briefing is the workflow that delivers the most obvious value, fastest, every single day.
Do this:
1. Decide what goes in your briefing. Pick three or four sources you check every morning. Some examples:
- Unread emails from the last 24 hours, prioritized
- Today’s calendar with prep notes for each meeting
- Your task list, sorted by what’s due today
- New leads, open bids, or whatever your business pipeline looks like
2. Open Cowork and type a starter prompt:
> “Every weekday morning, I want a one-page briefing. Pull from [your sources from step 1]. Format it with a short intro paragraph, then a section for each source. Keep it under 500 words. Show it to me here in chat.”
3. Read what comes back. Tell Claude what to add, cut, or reformat. (“Skip the newsletter promotional emails.” “Pull only meetings before noon.” “Sort by priority instead of time.”) Iterate until the briefing feels right.
4. Run it again the next morning. Refine. Run it again. Most people lock the format by Wednesday or Thursday.
5. Once the briefing is dialed, turn it into a scheduled task. In Cowork, type: “Take this morning briefing workflow and create a scheduled task that runs it every weekday at 6:30 AM (or your time). Save each day’s briefing as a dated file in my Cowork folder.” Cowork handles the scheduling. From now on, the briefing builds itself before you sit down. You walk in and the day’s briefing is waiting.
Friday’s win: You’re starting your day reading a briefing instead of building one. The cost of “what should I focus on this morning” drops from 30-plus minutes to under five.
Week 5: Kill Your Worst Workflow
Goal: Take one task you genuinely hate and rebuild it with Cowork sitting in the middle of it. Then turn it into a permanent capability.
A quick note on why this week. Weeks 1 through 4 set up the system. Week 5 is where you start using it to break a real bottleneck. Pick the task you put off, do badly, or do too late. The one that drains your week and that you’d love to hand off but never have.
Do this:
1. Pick the task. Make a quick list of everything that drains you week to week: bid responses, proposal drafts, expense reports, customer follow-ups, meeting notes, weekly team updates, vendor reviews. Pick one. Just one. (You can come back for the others.)
2. Let Cowork interview you about your current process. Paste this prompt:
> “I want to map out a workflow I do regularly so we can rebuild it together. Interview me one question at a time. Don’t bundle questions. Cover these areas: what task we’re mapping (name and trigger); the inputs I start with; the steps I currently take in order, with rough time estimates; the decisions I make along the way that need my judgment; the final output and where it goes. After the interview, output a clean workflow map titled ‘[Task Name] - Current Process’ with sections for trigger, inputs, steps, decision points, and output. Save it as a markdown file in my Cowork folder. Ask me question 1 now.”
Answer one question at a time. By the end, your current-state workflow is documented and saved.
3. Now ask Cowork to rebuild it. Type: “Read the workflow we just mapped. Tell me which steps you can do, which need my judgment, and how we’d run this together.” Read the response. Then push back: “Now propose a redesigned workflow where you handle as much as possible, and I make decisions on the things only I can decide.”
4. Run the redesigned workflow on a real example. The next bid. The next proposal. The next set of meeting notes. Don’t pre-clean anything. Use the actual messy input you’d normally start with.
5. Turn the workflow into a Cowork skill. Quick context: a skill is a reusable workflow that Claude can invoke automatically. Think of it as a saved playbook with a name. Once you build one, Cowork can run it any time you trigger it. We’ll do more with skills next week.
In Cowork, type: “Take this refined workflow and turn it into a Cowork skill called ‘[skill name like bid-response or proposal-draft]’. Build it so that when I say ‘[your trigger phrase, like let’s do a bid response]’, you run the skill automatically.”
Cowork’s skill creator handles the packaging. From now on, the workflow is a permanent capability you can call by name.
Friday’s win: A task that used to take two hours now takes about 20 minutes, and it isn’t a workflow you have to remember anymore. It’s a skill Cowork runs for you.
Week 6: Scale It Past Yourself
Goal: Stop being the only person in your company using Cowork. Make this institutional.
A quick note on why this week. You spent five weeks building. This week, you turn what you built into something your team uses too. The whole point of the manifesto was to grow without hiring proportionally. That only happens when more than one person has these tools running in their daily work.
Do this:
1. Install a plugin. In Cowork, open the plugin marketplace. Plugins are packaged sets of skills built for specific kinds of work: marketing, sales, brand voice, project management, and design. Pick one that fits a team or function in your company. Install it. Suddenly, Cowork knows how to run a brand review, generate a competitive analysis, draft an email sequence, or whatever the plugin does. Out of the box, no skill-building required.
2. Build a team skill. Last week, you built a skill for a workflow that only you do. This week, build one for a workflow your team does. Examples: “qualify a new lead,” “kick off a project,” “review a quote before it goes out.” Same pattern as Week 5, but the trigger phrase and instructions should make sense for anyone on your team to use, not just you.
3. Train one teammate. Pick one person on your team who’ll get the most leverage from this. Block an hour on the calendar. Sit with them. Walk them through Weeks 1 through 4: install Pro, set up Cowork, build their Personal Preferences, connect their tools, and stand up their morning briefing. They won’t be at your level by the end of the session. They’ll be a few weeks ahead of where most of their peers ever get.
4. Make it institutional. Add “Set up Cowork, first 30 days” to your new hire onboarding checklist. Document your team's skill from step 2 in a shared doc so anyone can find and use it. Pick a recurring slot (monthly works) for a 15-minute “what’s new in Cowork” share at your leadership meeting.
Friday’s win: You’re not the bottleneck anymore. Your team has the same fast-forward button you do. The growth-without-hiring promise from last week’s manifesto is no longer a thesis. It’s how things work around here.
Wrap Up
12 months from now, two operators are sitting across from each other at a chamber lunch.
The first one spent six weeks building a system. She talks about a strategic move she’s been working on. Her calendar has white space. Her team grew by one this year, not five.
The second one is exhausted. Still in the inbox. Still in the CRM. Still doing all the work he should have stopped doing a year ago. He says he’s been “meaning to get into the AI stuff.”
Don’t be the second one. (And if you’re reading this thinking “I am the second one”... GOOD. Now you know.)
Start Week 1 on Monday, May 18. Reply and tell me how it goes. I love hearing about this stuff.
As always, if you’d like to chat about rolling something like this out in your business, I’m here for you: scott@scottmonday.com.
Let’s build something real together. See you Monday!
No amount of agentic AI can help you if your business is unprofitable. Last week’s YouTube video from The Monday Method series is all about “Profit Islands,” a concept I developed to help operators identify their most profitable configurations. Watch it here!
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