Who This Is For
You're running a company at $1-5M in revenue. You have somewhere between five and 30 people. And you are personally responsible for too many things that aren't your actual job.
You write the investor updates. You prep for your own board meetings. You draft the job descriptions. You do the competitive research. You write the team updates. You probably haven't taken a real weekend off in months.
You're not bad at your job. You're doing too many jobs.
This guide shows you how to set up Claude Cowork as the operator sitting next to you. The one who handles the work that eats your nights and weekends while you focus on the stuff that actually requires a human with your judgment and your context.
No fluff. No theory. Just the folder structure, the context files, and the exact prompts for five workflows that will collectively hand you back hours every week. The setup takes 30 minutes. The payoff starts the first time you use it.
Step 1: Download Claude and Open Cowork
Go to claude.com/download. Install the desktop app.
Open it. Click the Cowork tab at the top.
Select the Opus 4.6 model. Turn on Extended Thinking. These are the settings you want for everything in this guide. Don't change them.
Step 2: Build Your Folder
Create one folder on your laptop. Call it Claude-Work.
Inside it, create four subfolders:
Claude-Work/
├── About Me/
├── Projects/
├── Templates/
└── Outputs/
About Me is where Claude learns who you are.
Projects is where you'll store materials for specific workflows.
Templates is for any reusable structures you build over time.
Outputs is where Claude delivers everything it creates.
Point Cowork to this folder. That's how it reads your context.
Step 3: Let Claude Interview You
This is the part that makes Claude useful instead of generic. Claude needs to know about your company, your role, and how you like to work. But you don't have to write any of that yourself.
Paste this prompt into Cowork:
I need you to build my context files. Interview me to learn about
my company, my role, how I work, and how I communicate. Use the
question form so I can pick answers instead of typing essays.
Ask me about:
- What my company does, our stage, revenue, team size, and what
we're focused on this quarter
- What I actually spend my time on day-to-day (be specific, not
just my title)
- The recurring tasks that eat my week: investor updates, team
comms, hiring, competitive research, content, meeting prep,
financial modeling, anything else that takes hours and shouldn't
require me personally
- How I like to communicate, write, and make decisions
- What I never want to see in my documents (jargon, buzzwords,
emojis, whatever I hate)
- What kind of company I'm trying to build and where I want to
be in 12 months
I also need you to learn my voice. Ask me:
- How would I describe my writing style in a few words?
(casual, formal, direct, warm, technical, conversational, etc.)
- Who are 2-3 writers, speakers, or public figures whose
communication style I admire or relate to?
- What does bad writing look like to me? What makes me cringe?
- If I were explaining something to a smart colleague over coffee,
how would that sound compared to how I write in emails right now?
Am I more formal in writing than I am in person, or about the same?
After the interview, ask me to paste in 2-3 short samples of
writing I'm happy with. These can be emails I've sent, LinkedIn
posts, Slack messages, memos, anything that sounds like me on a
good day. If I don't have samples handy, that's fine. Work with
what you have from the interview.
Go deep. Ask follow-up questions if my answers are vague. The more
you learn now, the better everything works later.
When you're done, create four markdown files in my About Me folder:
my-company.md, my-role.md, my-preferences.md, and my-voice.md.
my-voice.md should capture my writing style, tone, the things I
like and hate in written communication, and any patterns you
noticed in my samples. This is the file that makes "write in my
voice" actually mean something.
Add this line to my-preferences.md:
"Default ask: Read my files before every task. Ask me questions
before executing. Show a plan first. Don't guess."
Don't start writing until you've asked all the questions and I've
had a chance to share samples.
Claude will generate a clickable question form. You pick answers. Some questions will ask you to type a short response. Near the end, it'll ask you to paste in a few writing samples so it can learn how you actually sound. If you have a LinkedIn post you liked, a good email you sent, or even a Slack message where you explained something well, paste those in. If you don't have anything handy, skip it. The interview alone gives Claude plenty to work with.
Plan for about 15 minutes. That's not a typo. You want this to be thorough, because everything Claude does for you afterward is only as good as what it learned here. A five-minute interview gets you generic output. A fifteen-minute interview gets you output that sounds like it came from someone who's been sitting in your meetings for a month.
When you're done, Claude builds four files and saves them in your About Me folder:
my-company.md — your business, stage, metrics, priorities
my-role.md — what you actually do, what eats your time, what you'd offload
my-preferences.md — how you work, how you decide, what you hate in documents
my-voice.md — your writing style, tone, influences, pet peeves, and patterns from your samples
That last file is the one that makes "write in my voice" actually mean something in every workflow that follows. Without it, Claude writes in its own voice and you spend 20 minutes editing everything to sound like you. With it, the first draft is already close.
You never open a text editor. You never write markdown. You just have a conversation, share a few samples, and your context files exist.
This is also a good preview of how every workflow in this guide works. You give Claude a prompt. Claude asks you smart questions. You answer. Claude builds the thing. That's the pattern.
Step 4: Build Your Project Folders and Feed Them
Claude gets dramatically better when it can reference your actual work, not just your descriptions of it. This step has two parts: create the project subfolders for each workflow, then drop in whatever relevant documents you already have.
First, create these five folders inside your Projects folder:
Projects/
├── Investor Updates/
├── Team Comms/
├── Competitive Intel/
├── Hiring/
└── Content/
Each of these maps to one of the five workflows later in this guide. Now comes the part that most people skip and shouldn't: go find whatever documents you already have and drop them into the matching folder.
You probably have more of this stuff lying around than you think.
Projects/Investor Updates/
Your last two or three investor update emails (even if they were short or late)
Your most recent board deck or slides
A screenshot or export of your metrics dashboard
Any financial summary or KPI tracker you maintain
Projects/Team Comms/
A recent all-hands email or team update you sent
Meeting agendas or notes from recurring meetings
Any Slack messages where you explained a decision or announced something (copy-paste into a text file is fine)
Projects/Competitive Intel/
Any competitive slides from a board deck or sales presentation
A sales battlecard if you have one (even an outdated one)
Screenshots of competitor pricing pages or feature comparisons
Win/loss notes from recent deals
Projects/Hiring/
Job descriptions you've used before (good or bad)
Interview notes or feedback from past hiring rounds
Your org chart or team structure doc
Any notes on what went wrong with a previous hire
Projects/Content/
LinkedIn posts you've written that performed well
Posts from other people whose tone or style you admire
Newsletter editions or blog posts you're proud of
You don't need all of this. You don't even need most of it. But every real document you add teaches Claude something that an interview can't. The difference between "here's what I do" and "here's an example of what I actually produced" is the difference between Claude generating something plausible and generating something you'd actually send.
If a folder is empty, that's fine. The workflow will still work. But spend 10 minutes doing a quick scan of your laptop. You'll probably find more than you expect. Drag whatever you find into the matching folder. If something doesn't fit neatly, drop it in the closest match. Claude will figure out how to use it.
Step 5: Set Your Global Instructions
Go to Settings > Cowork > Edit Global Instructions.
Paste this:
I'm [Your Name], [Your Role] at [Company]. Read my context files
before every task. Ask questions using the question form before
executing. Show a plan before building anything. Never delete files
without my approval.
This runs automatically in every session. You set it once and never think about it again.
Your prompts can now be 10 words long. Claude already knows who you are, what your company does, and how you like to work.
Step 6: Install the Plugins That Matter
Click Customize > Browse Plugins > Install.
Start with the Marketing plugin and the Product Management plugin. These give you slash commands for things like competitive analysis, stakeholder updates, content drafting, and roadmap planning.
Type / in any conversation to see what's available.
You don't need all of them. Start with two and add more as you find workflows you want to automate.
Now the Good Part: Five Workflows That Get You Your Week Back
The setup above takes about 30 minutes if you're thorough about it. That's the honest number. The five workflows below are where the time savings actually happen, and they'll pay back that 30 minutes the first time you use any one of them. Each one follows the same structure:
The problem: the specific thing eating your time
The setup: any files or folders you need for this workflow
The prompt: copy-paste it exactly
What you get: what the output looks like
Workflow 1: Investor and Board Updates
The problem
It's Sunday night. You're staring at a blank doc trying to write the monthly investor update. You know what happened this month. You lived it. But turning four weeks of chaos into a coherent narrative that makes your investors feel good without lying to them? That takes two hours you don't have. So you either send it late, send it thin, or don't send it at all.
The setup
If you followed Step 4, your Projects/Investor Updates folder already has your past updates and board materials in it. Before running this workflow each month, drop in your latest metrics (a dashboard screenshot or CSV works fine) and any notes on significant wins or decisions from the month.
Even just last month's update and a current metrics screenshot gives Claude enough to work with.
The prompt
I need to write my monthly investor update. Read everything in the
Investor Updates folder.
Here's what happened this month:
- [2-3 bullet points of what actually happened. Wins, losses, decisions.]
- [Example: "Closed two enterprise deals. Lost our lead engineer.
Decided to push the product launch to April."]
Write the update in my voice. Keep it under 500 words. Structure it as:
highlights, key metrics with month-over-month context, challenges
(be honest but not alarming), and what's next. No buzzwords. No spin.
If something was bad, say it was bad and say what we're doing about it.
Ask me questions first if anything is unclear.
What you get
A draft investor update that sounds like you wrote it, uses your real numbers, and is honest about what went well and what didn't. You'll spend 10-15 minutes reviewing and editing instead of two hours writing from scratch.
Workflow 2: Weekly Team Communications
The problem
You have 15 people. Every Monday you need to send a team-wide update. Every Friday the department leads need summaries. You're prepping agendas for three recurring meetings. You're writing follow-up emails after every one of them. None of this is hard work. All of it takes time. And it adds up to three or four hours a week that you could be spending on the stuff only you can do.
The setup
Your Projects/Team Comms folder should already have any past team updates or meeting notes you dropped in during Step 4. The one new thing to add is a running file called this-week.md where you jot quick notes throughout the week. Doesn't need to be pretty. Just timestamps and bullets.
# This Week — [Date Range]
Monday: Kicked off new sprint. Design team behind on the onboarding flow.
Tuesday: Customer call with [Company]. They want API access by Q3.
Wednesday: Hired the senior engineer. Starts April 7.
Thursday: Board member flagged concerns about burn rate.
Friday: Product demo went well. Three new trial signups from it.
The prompt
Read my Team Comms folder. Using this-week.md, draft three things:
1. A Monday all-hands update for next week (3-4 paragraphs, conversational,
celebrate wins, flag blockers, set priorities)
2. A Friday summary email to department leads (bullet format, what
shipped, what's blocked, what needs decisions)
3. Action items from this week organized by owner
Keep everything in my voice. No corporate-speak. These are real people
I work with every day.
Ask me questions first if anything needs clarification.
What you get
Three ready-to-send communications that would have taken you 60-90 minutes to write manually. Review, tweak, send. This alone saves you an hour a week, every week.
Workflow 3: Competitive Intelligence
The problem
A prospect asked you last week how your product is different from [Competitor]. You gave an answer. It was fine. It was also different from the answer you gave the prospect before that, and the one before that. Because you don't actually have a documented competitive position. You have vibes.
Meanwhile, your biggest competitor shipped something two months ago that you still haven't looked at. Your sales team is winging every competitive question. And the last time you did any structured competitive research, it was a slide in your Series A deck that's now 18 months out of date.
The setup
Your Projects/Competitive Intel folder should already have whatever competitive materials you dropped in during Step 4. Before running this workflow for the first time, paste this setup prompt:
I need you to build a competitors file. Interview me about my
competitive landscape using the question form.
Ask me about:
- Who are our top three competitors?
- For each one: what do they do, where do they overlap with us,
and where are they different?
- Which competitor comes up most in sales conversations?
- What's the most common question prospects ask about them?
- Where do we win against each one, and where do we lose?
When you're done, create a file called competitors.md in my
Competitive Intel folder with everything you learned.
Claude interviews you, builds the file, and saves it. You can also connect web-accessible tools through Cowork's connectors (Settings > Connectors). If your competitors have public changelogs, blogs, or pricing pages, Claude can pull from those directly.
The prompt
Read everything in my Competitive Intel folder. Then do a competitive
analysis against our top 3 competitors.
For each competitor, tell me:
- What they shipped or announced in the last 90 days (search their
blog, changelog, and any press coverage)
- Where they're gaining ground on us
- Where we have a clear advantage
- The one thing a prospect would ask about them that I need a
better answer for
Then build me a one-page battlecard I can share with my sales team.
Keep it practical. No fluff. These are talking points for real
conversations, not a strategy deck.
Ask me questions first if you need more context on our positioning.
What you get
A competitive landscape analysis and a battlecard your sales team can use tomorrow. The kind of deliverable that would take a research analyst a week. You'll have it in 20 minutes, and you can run the same prompt again next quarter to keep it current.
Workflow 4: Hiring (Job Posts, Scorecards, and Interview Prep)
The problem
You're hiring for two roles. You wrote both job descriptions at 11 PM because they needed to go up yesterday. One reads like every other JD on the internet. The other one you're not even sure accurately describes the role anymore because the role changed three times since you posted it.
Your interview process is "talk to the candidate for 45 minutes and go with your gut." You know this is how bad hires happen. Your last bad hire cost you six months. You just haven't had time to build anything better because you're too busy doing the job of the person you're trying to hire.
The setup
Your Projects/Hiring folder should already have any old JDs, org charts, or interview notes you dropped in during Step 4. For each new role, create a subfolder with the role name and add anything specific: the rough JD you've drafted, what the role needs to accomplish in the first 90 days, notes on what went wrong with previous hires in similar roles.
The prompt
I'm hiring a [Role Title]. Read everything in the Hiring/[Role] folder.
I need three things:
1. A job description that sounds like a human wrote it. No buzzwords,
no "fast-paced environment," no "rockstar." Describe what the person
will actually do in their first 6 months, what success looks like,
and what kind of person thrives here. Be specific about the problems
they'll solve, not just the skills they need.
2. An interview scorecard with 5-6 criteria tied to the actual job,
each with a 1-5 rating scale and descriptions of what a 1, 3,
and 5 look like. I want to be able to hand this to any interviewer
and have them evaluate candidates consistently.
3. Ten interview questions that test for the things that matter, not
the things candidates rehearse. No "tell me about a time when"
softballs. Questions that reveal how someone actually thinks
and works.
Ask me questions first. I'd rather you understand the role than guess.
What you get
A JD that reads like a human with opinions wrote it. A scorecard that turns your gut-feel interview process into something you can hand to any interviewer on your team and get consistent evaluations. And ten interview questions designed to reveal how someone actually thinks, not how well they rehearsed the STAR method. The whole package takes longer to read than it takes Claude to build.
Workflow 5: LinkedIn Content and Thought Leadership
The problem
You have ten years of experience and strong opinions about your industry. You know that posting on LinkedIn would build your personal brand, attract talent, and generate inbound leads. You also know that the last time you tried to write a post, you stared at a blank screen for 20 minutes, wrote three mediocre sentences, got interrupted by a Slack message, and never came back to it.
So you post once every two weeks. Maybe less. Your profile looks like a ghost town, and the people who would hire you or invest in you or buy from you have no idea what you think about anything.
The setup
Your Projects/Content folder should already have any LinkedIn posts or writing samples you dropped in during Step 4. Those samples, combined with the my-voice.md file Claude built during your interview, are what make this workflow produce drafts that actually sound like you instead of sounding like a chatbot.
Before your first content session, paste this setup prompt to build your ideas bank:
I need you to build a content ideas file. Interview me using the
question form.
Ask me about:
- What topics do I have the strongest opinions about in my industry?
- What mistakes do I see founders making that I could write about?
- What lessons did I learn the hard way that would save someone
else time or money?
- What questions do customers, employees, or investors ask me
most often?
- What conventional wisdom in my field do I think is wrong?
When you're done, create a file called ideas.md in my Content
folder with at least 10 content ideas based on my answers, each
described in one sentence.
Claude interviews you and builds the file. Going forward, whenever an idea hits you, just tell Claude to add it to the list. The goal is to never sit down to write without a bank of things to write about.
The prompt
Read my Content folder. Pick the idea that you think has the most
potential to resonate with growth-stage founders and write me a
LinkedIn post about it.
Structure: Hook that stops the scroll (2 lines max, no gimmicks).
Then a short story or specific example that makes the point real.
Then the insight. Then a question or CTA that invites conversation.
Keep it under 200 words. Write in my voice. Conversational, direct,
like I'm telling a friend something useful over a beer. No jargon.
No emojis. No "here are 5 tips" formatting.
Give me three options and let me pick. Ask questions first if you
need more context on my audience or voice.
What you get
Three draft LinkedIn posts, each with a strong hook and a clear point. You pick the one that feels right, edit for 10 minutes, and post. What used to take 90 minutes now takes 15. Post twice a week instead of twice a month.
One More Thing
Every prompt in this guide ends with "ask me questions first." That's intentional.
Claude works best when it understands the context before it starts building. When you tell it to ask questions, it uses a clickable question form where you pick answers instead of typing paragraphs. It takes 30 seconds. And the difference between a Claude output with good context and one without is the difference between "that's actually useful" and "that's a very polished piece of nothing."
The same logic applies to your voice file and your project folders. Claude with an empty About Me folder is a smart generalist. Claude with your voice profile, your past investor updates, your old job descriptions, and your writing samples is something closer to a colleague who's been paying attention. The more context it has, the less time you spend editing its output. And the less time you spend editing, the more time you actually get back.
Don't skip the context. Don't skip the questions. That's the whole game.
What's Next for This Setup
Anthropic just shipped Projects in Cowork, which lets you turn each workflow into its own workspace with persistent memory and dedicated instructions. Instead of one big folder, each workflow becomes a self-contained project that remembers what you did last time. I'm migrating my own setup now. Once I've run it long enough to have real opinions about what's better, I'll update this guide.
About This Guide
I'm Jason Jackson. I spent 20 years in product and operations at companies ranging from startups to enterprises, and now I work with growth-stage founders and executives who are learning how to build companies that don't require them to be in every room, on every call, and awake at 3 AM.
I write a weekly newsletter called The Next Gear about the operational, strategic, and very human challenges of scaling a company. You probably just subscribed to it to get this guide. One email a week. No fluff, no pitches, just something useful (and, if I wrote it properly, a little bit funny) you can read on a Wednesday morning.
