Every founder I work with hits the same wall: they know AI is fast, they just can't figure out which thirty minutes of work to hand over first. So they keep doing everything by hand, then feel vaguely guilty when they read someone else's "I built a $10M business with AI" thread.
The list below is the opposite. Real prompts, in production, on real founders' machines. Each one assumes you are running Claude Cowork (not Chat) so it can read your files, hit your tools and produce actual outputs. Copy the prompts. Adjust the bracketed bits. Run them. Notice which ones save you the most time, then schedule those to run on a cadence.
How to use this list
Three rules of thumb before you start:
- Set up two reference files in your Cowork workspace:
about-me.md(who you are, what you sell, who you sell to) andbrand-voice.md(how you write, words you avoid, examples). Most prompts below assume Cowork can read them. - Start with one prompt. Get it working. Then add a second. Trying all ten on day one is a great way to give up on day two.
- Once a prompt is reliable, save it as a scheduled task. The compound effect is the point.
1. Email Inbox Zero Assistant
Triage your unread inbox in five minutes instead of forty. Cowork reads, classifies, and drafts where appropriate.
ROLE: You are my inbox triage agent.
TASK: Process my last 48 hours of unread Gmail and produce a zero-scrolling triage table I can act on in 5 minutes.
INPUT SCOPE:
- All unread emails from the past 48 hours in my Gmail
- Read brand-voice.md from this folder for tone and word choices
- Read about-me.md from this folder for who I am and what I work on
CLASSIFY EACH EMAIL AS ONE OF:
- ACTION (something I have to do that is not a reply)
- REPLY (someone is waiting on a response from me)
- FYI (good to know, no action required)
- DELETE (newsletter, marketing, transactional, no value)
FOR EACH EMAIL, EXTRACT:
- Sender (name + company if known)
- Subject line
- One-sentence summary of what they want
- Urgency (this week / this month / no rush)
- Suggested classification
FOR REPLY ITEMS:
- Draft a 2-sentence response in my voice using brand-voice.md
- Match the formality of the inbound message
- Keep it shorter than the original
FOR ACTION ITEMS:
- Summarise what I need to do in one line
- Note the deadline if mentioned
- Flag if the sender is a customer, investor, or team member
OUTPUT FORMAT:
A single markdown table with columns:
| Type | From | Subject | Summary | Action / Draft Reply | Deadline |
After the table, list:
- Top 3 emails to handle first (and why)
- Anything that looks like phishing or spam
- Recurring patterns I should set up filters for
Save the output as inbox-triage-[YYYY-MM-DD].md in this folder.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything about your current focus, e.g. "fundraising right now, anything investor-related is high priority"]
Setup: Connect Gmail. Drop a brand-voice.md and about-me.md in your workspace.
2. Subscription Audit and Cleaner
Quietly bleed-out subscriptions are the easiest £200 to £600 a month most founders find when they audit. Cowork does it once and surfaces the redundant ones.
ROLE: You are my subscription auditor. TASK: Surface every recurring charge across my business and personal accounts, categorise them, flag the dubious ones, and recommend cancellations. INPUT SCOPE: - Read bank-statement.csv (last 3 months) in this folder - Read stripe-export.csv (last 3 months) in this folder - Read any annual receipts in /receipts/ if present IDENTIFY EVERY RECURRING CHARGE: - Same merchant, same or similar amount, monthly or annual cadence - Include trial-to-paid conversions CATEGORISE INTO: - Software (productivity, tools, hosting, AI) - Media (streaming, news, books) - Productivity (storage, password managers, calendars) - Business services (accounting, legal, insurance) - Personal (gym, food, lifestyle) - Other / unidentified FOR EACH SUBSCRIPTION, OUTPUT: - Merchant name - Monthly cost (annual divided by 12 if billed yearly) - Annual cost - Category - First charged date - Last charged date - Status flag (see below) STATUS FLAGS TO USE: - DUPLICATE: another tool in this list does the same thing - DORMANT: not logged into in 90+ days (use sign-in data if available) - OVER-£40: monthly cost above £40, worth a closer look - TRIAL-CONVERTED: a trial that flipped into paid, worth confirming you wanted it - OK: keep, in active use OUTPUT FORMAT: 1. Summary table sorted by annual cost descending 2. Total annual subscription spend across all categories 3. Top 5 to cancel with one-line rationale for each 4. Top 5 worth keeping with one-line rationale Save as subscription-audit-[YYYY-MM-DD].md. MY CONTEXT: [add anything, e.g. "we are reducing burn, cancel anything we don't use weekly"]
Setup: Export the last 3 months of charges from your bank and Stripe as CSV.
3. Weekly Review Generator
Friday afternoon, 10 minutes, instead of frantically reconstructing the week from memory on Monday morning.
ROLE: You are my Friday review writer.
TASK: Reconstruct my work week from data, surface what shipped vs what slipped, and set me up for next week.
INPUT SCOPE:
- My Google Calendar for the past 7 days
- My Slack DMs sent and received in the past 7 days
- Read priorities.md from this folder (this week's plan)
- Read any meeting notes saved in /transcripts/ from this period
- Read /weekly-reviews/last-week.md so you know what I planned to ship
STRUCTURE THE REVIEW AS:
## What I shipped
- List of completed work, projects moved forward, decisions taken
- Group by function (product, sales, hiring, finance, ops, comms)
- Quantify where possible (e.g. "shipped X feature, used by Y customers in week 1")
## What slipped and why
- Items I planned but did not complete
- Best-guess root cause (interruption, scope, blocker, deprioritised)
- One sentence each
## Where my time actually went
- Estimated hours by category, based on calendar
- Compare to what I planned in priorities.md
- Flag any meeting type that took more time than usual
## Energy and signals
- Anything that looked like a recurring frustration
- Themes from Slack DMs (what people kept asking me)
- One thing I did this week that I am proud of
## Top 3 priorities for next week
- Specific outcomes, not vague themes
- Each priority gets one supporting action
## One thing to drop
- Something I should stop doing or hand off
- Why now
OUTPUT FORMAT: Markdown document, scannable in 90 seconds.
Save as /weekly-reviews/week-[YYYY-MM-DD].md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything, e.g. "this week I was at a conference Wed to Fri so calendar is misleading"]
Setup: Connect Google Calendar and Slack. Keep a priorities.md file you update weekly.
4. Desktop Deep Clean
The Downloads folder doom pile, sorted in 90 seconds. With a confirmation step before anything is deleted.
ROLE: You are my desktop cleaner. TASK: Triage and reorganise my Downloads folder. Show me the plan first. Do not move or delete anything until I confirm. INPUT SCOPE: - Every file in ~/Downloads created more than 60 days ago - Read about-me.md to know what kind of work I do (helps with naming) GROUP FILES BY TYPE: - PDFs (further split into invoices, contracts, articles, receipts, other) - Screenshots - Installers (.dmg, .pkg, .exe, .zip with binaries) - Exports (.csv, .xlsx, raw data dumps) - Images (.jpg, .png, .heic, non-screenshot) - Documents (.docx, .pages, .txt, .md) - Archives (.zip, .tar.gz that look like backups) - Other FOR EACH FILE, PROPOSE: - New filename in YYYY-MM-DD-descriptive-name.ext format - Destination folder (suggest a sensible structure under ~/Documents/Archive/) - Action: KEEP / DELETE / NEEDS-DECISION WHAT TO DELETE BY DEFAULT: - Installers older than 30 days - Duplicate files (same name, same size) - Screenshots older than 90 days - Auto-generated exports from tools I no longer use WHAT TO FLAG AS NEEDS-DECISION: - Anything that looks like a contract, invoice, or signed document - Files with names suggesting customer or investor data - Anything you cannot confidently categorise OUTPUT FORMAT: 1. Summary: total files, total size, breakdown by type 2. Full table: filename, proposed new name, destination, action, rationale 3. List of NEEDS-DECISION files to review with me 4. Stop and wait for my confirmation before executing After my confirmation: - Execute the renames and moves - Move files to ~/.Trash, do not permanently delete - Save a manifest of what was moved at /downloads-cleanup-[YYYY-MM-DD].md MY CONTEXT: [add anything, e.g. "I was at three conferences this year, lots of legitimate decks in there"]
Setup: Point Cowork at your Downloads folder when prompted.
5. Expense Tracker and Audit
Categorise the month's spend, find the things that should not be there, and produce something your accountant can actually use.
ROLE: You are my expense auditor. TASK: Read my monthly bank statement and produce a categorised, audited report I can hand to my accountant. INPUT SCOPE: - bank-statement.csv in this folder (one calendar month) - stripe-export.csv if present (income side, for reconciliation) - Read /chart-of-accounts.md if it exists CATEGORISE EVERY OUTBOUND TRANSACTION OVER £20 INTO: - Software & SaaS - Travel (flights, trains, taxis, hotels) - Marketing & advertising - Office & supplies - Subcontractors & freelancers - Professional services (legal, accounting) - Subsistence (meals during work) - Personal-mistake (looks personal but went on the business card) - Refunds / reversals - Other (you cannot place it confidently) FOR EACH TRANSACTION, EXTRACT: - Date - Merchant - Amount - Category - Confidence (high / medium / low) - Flag (see below) FLAGS TO RAISE: - DUPLICATE: same merchant, same amount, same week - UNKNOWN-MERCHANT: I have not transacted with this merchant before - PERSONAL: looks personal (e.g. groceries, personal subscriptions) - LARGE: single transaction over £500 - UNUSUAL: amount or merchant does not fit my normal pattern OUTPUT FORMAT: 1. Summary table: total spend by category, with month-on-month delta if possible 2. Full transaction table: date, merchant, amount, category, confidence, flag 3. Things to investigate: list of all flagged transactions with one-line context 4. Receipts I should chase: list of transactions where I should have a receipt Save as expenses-[YYYY-MM].md. MY CONTEXT: [add anything, e.g. "I bought some equipment for the new hire this month, that is legit"]
Setup: Drop your monthly bank statement export as CSV.
6. Call Prep Brief
Walking into every call with a one-page brief is one of the highest-leverage habits you can build. Cowork makes it free.
ROLE: You are my call prep agent.
TASK: I have a call with [NAME] from [COMPANY] on [DATE/TIME]. Build me a one-page brief I can read in two minutes before the call starts.
INPUT SCOPE:
- My Gmail thread with this person (search by email or domain)
- Any past meeting transcripts in /transcripts/ that include them
- Their LinkedIn profile (search the web)
- Their company's news in the last 60 days (search the web)
- Any notes in /crm/[company].md if present
- Read about-me.md and brand-voice.md
PRODUCE THE BRIEF WITH THESE SECTIONS:
## Relationship recap
- How we know each other (3 lines max)
- Last contact: date, channel, what we discussed
- Tone of past conversations (warm, transactional, awkward)
## Who they are now
- Current role and how recently they joined
- Notable career moves in the last 2 years
- Anything specific they have posted, written, or been quoted on recently
## Their company in 30 seconds
- What they do, who they sell to
- Stage (size, funding, headcount range)
- News in the last 60 days they might mention
## Their likely goals for this call
- Best guess at what they want from us
- Three reasons they might have accepted the meeting
## What I should ask
- Three questions, in priority order
- Each grounded in something specific from the research above
## What I can offer
- Two or three concrete things I can give them (intro, advice, resource)
- One thing I should NOT promise
## The one outcome
- The single thing I should walk out of this call with
## Quick facts at the bottom
- Mutual connections worth name-dropping (with how we know them)
- Anything not to bring up (sensitive past projects, awkward connections)
OUTPUT FORMAT: Markdown, max one page printed.
Save as /call-prep/[YYYY-MM-DD]-[name].md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything, e.g. "trying to close them as a customer, partnership angle is secondary"]
Setup: Connect Gmail and your transcript source (Granola, Otter, Fathom). Add a calendar connector for automatic prep on every meeting.
7. Investor Update Drafter
Monthly updates are a leading indicator of investor relationships. Cowork drafts in your voice using the same template you've used before.
ROLE: You are my investor update writer.
TASK: Draft this month's investor update in my voice, matching the structure and tone of past updates.
INPUT SCOPE:
- /metrics/this-month.csv with current month's KPIs
- /metrics/last-month.csv for month-on-month deltas
- /priorities.md for what we said we would do this month
- /investor-updates/ folder containing the last 3 monthly updates (for voice and structure)
- Read about-me.md and brand-voice.md
STRUCTURE THE UPDATE EXACTLY AS:
## Headline
- One sentence summarising the month
- Tone: confident if numbers are up, honest if numbers are down
- Never use the word "exciting"
## Key metrics
- Table of 4 to 7 metrics, current vs last month, with % delta
- Mark anything 20% or more in either direction with a comment
- Include: revenue, new customers, active customers, churn, runway, hiring
## Wins
- 3 to 5 specific wins from the month
- Quantify where possible (e.g. "shipped X feature, used by Y customers in week 1")
- One sentence each
## Lowlights
- 2 to 3 things that did not go to plan
- Be honest about why
- Note what we are doing about each
## Asks
- 1 to 3 specific things investors can help with
- Make them named asks (e.g. "intro to [name] at [company]")
## Team
- New hires this month
- Any departures
- What we are hiring for next
## Looking ahead
- Top 3 priorities for the coming month
- One number we are watching
VOICE RULES:
- Match the rhythm and length of the last 3 updates
- Use the same terms for metrics (do not switch from "MRR" to "monthly revenue")
- Mark anything you were not 100% sure about with [VERIFY]
OUTPUT FORMAT: Markdown.
Save as /investor-updates/[YYYY-MM]-update.md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything, e.g. "we missed the revenue target, lead with the customer wins instead of the headline number"]
Setup: Keep monthly metrics and past updates in dedicated folders. Drop the latest in before running.
8. Customer Feedback Synthesiser
The fastest way to figure out what to build next, what to fix, and what's quietly working. Themes, not anecdotes.
ROLE: You are my voice-of-customer analyst.
TASK: Read every piece of customer feedback I have and produce a structured analysis I can act on.
INPUT SCOPE:
- /support-export.csv (all support tickets from the last 90 days)
- /surveys.csv (all NPS or feedback survey responses, last 90 days)
- /sales-call-notes/ folder if it exists (transcripts of customer interviews)
- /reviews-export.csv if I have public reviews data
- Read about-me.md so you know our positioning
CLUSTER ALL FEEDBACK INTO 5 TO 7 THEMES.
For each theme:
## Theme: [name]
- Volume: how many mentions
- Severity: critical / important / nice to have
- Type: feature gap / bug / onboarding / pricing / positioning / support
- Two representative quotes (verbatim, with source)
- Pattern: what specifically are people trying to do
- Who is feeling this most: customer segment, use case, plan tier
ALSO PRODUCE:
## What is working
- 3 things customers consistently praise
- Use these in marketing copy
## What customers expected but did not get
- Implicit promises we are not delivering on
- Indicates positioning or onboarding fixes
## Top 3 to act on this quarter
- For each: theme, recommended action, rough cost to fix, expected impact
## Quotes I should put on the website
- 5 quotes, with permission status flagged (assume "needs permission" unless source says otherwise)
OUTPUT FORMAT: Markdown.
Save as /research/customer-feedback-[YYYY-MM].md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything, e.g. "we are considering a price increase, look closely at price-sensitivity signals"]
Setup: Export tickets from your support tool and surveys from your form tool. CSVs work best.
9. Personal CRM Catch-up
Network entropy is real. The 30 people you should be staying close to slowly become 30 people you have not spoken to in six months. Cowork brings them back.
ROLE: You are my relationship maintenance assistant.
TASK: Identify who in my network has gone too quiet and draft warm, contextual messages to bring them back.
INPUT SCOPE:
- /people/contacts.md (my list of important contacts with last-contact dates and topics)
- /transcripts/ if it has past meetings with these people
- My Gmail (search by name or email)
- Read brand-voice.md and about-me.md
FILTER FOR:
- Anyone tagged "priority" in contacts.md
- Whose last contact date is more than 60 days ago
- Who is not already in an active thread (check Gmail)
FOR EACH PERSON, OUTPUT:
## [Person's name]
- Role / company
- Last contact: [date], via [channel]
- Last topic: [what we discussed]
- Why they matter: [one line, e.g. investor, customer, advisor, friend, expert]
- Suggested touchpoint type, pick one:
- SHARE: send them an article, post, or update relevant to them
- ASK: ask a thoughtful question about something they care about
- CHECK-IN: light social check-in with no agenda
- INTRO: offer to connect them with someone useful
## Draft message
- 3 lines, written in my voice from brand-voice.md
- References our last topic specifically
- Does not ask for anything unless I am offering
## Best channel
- Email / LinkedIn / Whatsapp / Signal
- Based on where past contact happened
DO NOT SEND ANYTHING. Just draft and present.
OUTPUT FORMAT: Markdown, one section per person, sorted by how long since last contact.
Save as /people/catchup-[YYYY-MM-DD].md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything, e.g. "I am raising next quarter, prioritise investors and warm intros"]
Setup: Maintain a people/contacts.md file with names, last contact date, last topic, and a tag.
10. Decision Memo Writer
Most founder decisions get made in a Slack thread or a 6pm shower. The good ones get documented. Cowork can do the documenting for you.
ROLE: You are my decision memo writer.
TASK: Help me think through a decision properly and produce a one-page memo I can share with my team or co-founder.
THE DECISION I AM FACING:
[describe the decision in 2 to 3 sentences]
DEADLINE FOR DECISION: [date]
WHO ELSE NEEDS TO WEIGH IN: [list, or "just me"]
INPUT SCOPE:
- Read /strategy.md for our current operating context
- Read /past-decisions/ to learn from how I have decided similar things before
- Read about-me.md for my decision-making style
PRODUCE A MEMO WITH:
## The decision in one sentence
- Stated cleanly
- Date it must be made by
## Context
- Why this decision matters now
- What will happen if I do not decide
## Options
- 3 to 5 distinct options (including "do nothing" if relevant)
- Each described in 2 to 3 lines
## For each option
- Pros (3 max)
- Cons (3 max)
- Rough cost (£, time, opportunity)
- Reversibility: one-way door or two-way door
- What it depends on being true to be the right call
## My recommendation
- Pick one option
- One paragraph explaining why
- What I am most worried about
## What would change my mind
- Specific facts or signals that should make me reconsider
- Date by which they would have to surface
## Reversibility check
- If I am wrong, how do I find out fastest
- How do I unwind it
## Lessons from past decisions
- Reference 1 to 2 past decisions in /past-decisions/ where I made a similar call
- What I got right or wrong then
OUTPUT FORMAT: Markdown, one printed page if shared.
Save as /past-decisions/[YYYY-MM-DD]-[short-decision-name].md.
WRITING STYLE:
- Short sentences with varied rhythm
- Simple words, active voice
- Concrete nouns, strong verbs
- Show through details, not adjectives
- Trust the reader
- One idea per sentence, one topic per paragraph
- Cut every word that does not earn its place
- First drafts: half the length you think is right. "Shorter" means cut 50% minimum.
- Restrict emoji use to where it really proves a point
BANNED WORDS & PHRASES:
- Never use em-dash ('—' or '--')
- Never use: fosters, foster, landscape, delve, invaluable, enlightening, in the realm of, elevate, enhance, tapestry, crafting, in the digital landscape, in the world of, unsung hero, harmonious dance, secret weapon, cultivate, this is gold, this is a game changer, this hits, fluff, the kicker, here's the thing, the shift
MY CONTEXT: [add anything specific, e.g. "this decision affects fundraising timing, we have a board meeting next week"]
Setup: Keep a strategy.md with your current operating context. Save each decision memo into /past-decisions/ so future ones get smarter.
Most prompt lists are written for chat: copy, paste, get a paragraph back. These ten are written for Cowork: copy, paste, get a real output saved to a real file using your real data. The first one feels like magic. The fifth feels like leverage. By the tenth, you have got back a half-day a week and you are ready for the next ten.