The Claude Fable 5 Prompt Library for Small Business Owners: 47 Prompts That Find Money, Clients, and Hours

Prompt 1

Take inventory of what you can actually access for my business.

Create two lists.

First: live connections. Check which apps and tools you can access right now through connectors, integrations, plugins, or API keys. Look specifically for email, calendar, accounting, invoices, payments, CRM, file storage, project management tools, website data, and anything else connected to this workspace.

For each live connection, run only a harmless read-only check. Tell me what worked, what did not work, and what you were able to confirm. Do not describe what should be possible. Describe only what actually worked.

Second: local or uploaded business files. Look for business documents, spreadsheets, exports, proposals, contracts, invoices, client folders, marketing assets, SOPs, and reports. Do not open anything that appears highly sensitive without flagging it first.

Then give me a plain-English map:

1. What you can access live
2. What you can only access as files
3. What you cannot access at all
4. What I would need to connect or upload to make the next prompts work better
5. Three useful things you could do for me this week using only what is available right now

Use plain business language. No technical jargon.

Prompt 2

Build a business memory file for me.

Do not interview me first. Use existing evidence.

Read what you can access: my website, email history, calendar, accounting records, CRM, proposals, invoices, contracts, client folders, service pages, and business documents.

Create a one-page business memory file that covers:

1. What this business sells
2. Who buys it
3. The main offers or services
4. Typical pricing or project size
5. Key people, roles, clients, vendors, or partners
6. Common client problems
7. How we usually talk to clients based on real sent emails
8. Any standing rules I should keep in place

Mark anything uncertain as [ASSUMPTION]. Do not pretend guesses are facts.

Show me the draft first and let me correct it. After I approve it, save it as BUSINESS_MEMORY.md. If this workspace already uses CLAUDE.md or another agent instruction file, update that file too.

Prompt 3

Read my business memory file. Then review evidence of how work actually happens in my business: sent emails, recurring documents, spreadsheets, client folders, calendar patterns, project management tasks, reports, and repeated messages.

Identify the top ten tasks I should hand off to you.

Rank them by likely monthly time saved and business value.

For each task, tell me:

1. What the task is
2. How often it appears to happen
3. What evidence you used
4. What you would need from me once
5. What output I would get back
6. Whether it is low-risk, medium-risk, or high-risk
7. Whether it should require my approval before anything external happens

Then write the full ready-to-paste prompt for the top three tasks so I can start using them today.

Prompt 4

Add these standing rules to my business memory file and follow them in every future session.

Permanent red lines. These never change, no matter what:

1. Never commit me to a price, discount, refund, payment plan, scope change, or contract term. Money and legal promises are mine alone.
2. Never present a guess as a fact. Mark anything uncertain as [ASSUMPTION].
3. When something could cost real money, create legal exposure, or damage a client relationship, stop and show me before acting.

Working rules. These are my starting defaults. They are meant to loosen over time, but only when I explicitly say so:

4. Client-facing and external messages: draft and HOLD until I approve each one.
5. Publishing anything publicly: approval first.
6. Deleting, moving, renaming, or overwriting files: show me the plan first.

How loosening works:

- Only I can loosen a working rule, and only in specific carve-outs, never wholesale. Example: "You can file invoices into the client folders without asking" or "Send routine payment receipts automatically."
- When I grant a carve-out, record it in the memory file with the date and its exact limits. Everything outside the carve-out stays on approval.
- If you have earned a strong track record on some category of task, you may propose a carve-out and show me the evidence. I decide.

One more rule so this does not slow us down: never use these rules as a reason to stall. If a task can proceed safely in draft form, proceed and bring me the drafts. Ask only when a red line is actually in play.

Confirm these rules back to me in plain English. Then save them to the business memory file.

Prompt 5

Build me a true accounts receivable picture.

Use this source order:

1. Live accounting, invoicing, or payment systems first, such as QuickBooks, Xero, Stripe, Square, FreshBooks, Wave, or similar
2. Invoice exports, payment exports, spreadsheets, or invoice PDFs second
3. If neither is available, stop and tell me exactly which report to export and where to find it

Do not call anything overdue until you cross-check whether payment was actually received.

Show me:

1. Total outstanding amount
2. Every unpaid invoice by client
3. Aging buckets: current, 1-30 days, 31-60 days, 61-90 days, and 90+ days
4. The three clients holding the most outstanding money
5. Partial payments
6. Credits that appear unapplied
7. Invoices created but not sent
8. Anything that looks odd or inconsistent

Then draft a collection message for each genuinely overdue invoice.

Use the relationship history from my email before drafting:

- Good client under 30 days late: friendly nudge
- 31-60 days late: clear follow-up
- 61-90 days late: firmer message
- 90+ days late: flag as call-first and give me three talking points instead of an email

Mark every draft HOLD. Do not send anything.

End with one sentence: the single invoicing habit that would make this list shorter next month.

Prompt 6

Analyze my business expenses.

Use live accounting or payment systems first. If you cannot access those, use exports, spreadsheets, bank/card reports, receipts, or expense files. If you have none of those, tell me exactly what report to download and from where.

Group expenses into plain business-owner categories:

- Payroll
- Contractors
- Software
- Rent or office
- Marketing
- Advertising
- Travel
- Professional services
- Taxes and fees
- Equipment
- Everything else

Then show me:

1. Total expenses for the period reviewed
2. The fastest-growing categories
3. The five biggest individual expenses
4. Recurring charges that look unusually high
5. Duplicate or suspicious charges
6. Expenses that do not clearly connect to revenue, delivery, retention, or operations

Keep it to one page. Use plain language, not accounting jargon.

Prompt 7

Find every recurring subscription or recurring charge in my business.

Use accounting, bank/card, or payment data first. If unavailable, use invoices, receipts, email confirmations, or exports.

For each recurring charge, list:

1. Vendor
2. Monthly or annual cost
3. Billing frequency
4. What the tool or service appears to be for
5. Last evidence of use, if available
6. Whether it looks essential, questionable, or likely unused

Look for usage evidence in email alerts, login notices, invoices, files, calendar events, team references, or project records.

Flag anything with no evidence of meaningful use in the last 90 days.

At the top, show the total estimated annual savings if I cancel the likely-unused items.

Do not cancel anything. Give me a cancel-candidate list only.

Prompt 8

Review my pricing.

Use proposals, invoices, contracts, website pages, sales emails, and service documents from the last two years.

Tell me:

1. When I last raised prices
2. My average project/order value by year
3. Which services are being quoted at the same price as one or two years ago
4. Which clients or offer types are still on old pricing
5. Where my scope has grown but the price has not

Then review three public competitors or comparable providers. Use only public information you can actually find. Tell me what they charge, how they package similar work, and where I appear underpriced or overcomplicated.

Do not tell me to "charge what I'm worth." Give me specific numbers and the reasoning behind them.

Prompt 9

Rank my clients by profit per hour of attention, not just revenue.

Use invoices, payment records, proposals, email volume, meeting history, revision rounds, support requests, project delays, and client notes.

For each client, estimate:

1. Total revenue
2. Number of emails or threads
3. Number of meetings
4. Revision rounds or support requests
5. Timeline friction
6. Scope creep signals
7. Estimated attention required

Then rank:

- Best five clients by profit per hour of attention
- Worst five clients by profit per hour of attention
- The client who looks good on revenue but appears costly once effort is counted
- The client who is underrated because they are low-drama and profitable

Show the evidence used. Mark estimates clearly.

Prompt 10

Analyze my client concentration risk.

Use invoices, payment records, and revenue data from the last 12 months.

Tell me what percentage of revenue came from:

1. My largest client
2. My top three clients
3. My top five clients

Then review the relationship evidence for those clients: contracts, renewal dates, payment history, recent email tone, meeting history, and any unresolved issues.

Tell me plainly:

1. What happens if the largest client leaves next month
2. Whether the relationship looks stable, uncertain, or at risk
3. The fastest two realistic moves to reduce this exposure
4. Which past or current clients are most likely to help fill the gap

Use numbers. Do not reassure me unless the evidence supports it.

Prompt 11

Build a simple 90-day cash picture.

Use live accounting, payments, invoicing, payroll, and expense tools first. Use files and exports second.

Include:

1. Expected money in, by week
2. Expected money out, by week
3. Invoices due and their real due dates
4. Recurring charges
5. Payroll or contractor payments, if available
6. Known upcoming commitments from email, contracts, or calendar
7. Any payments that look uncertain

Lay it out week by week.

Flag any week that looks tight.

If a tight week exists, list the three fastest levers in order:

1. Which invoice to chase
2. Which expense to pause or delay
3. Which payment or commitment to renegotiate

Use a simple table. No accounting jargon.

Prompt 12

Analyze my payment terms and actual payment behavior.

Use invoices, contracts, proposals, accounting records, payment records, and email threads.

Tell me:

1. Current payment terms I use
2. Average days-to-pay by client
3. Clients who consistently pay on time
4. Clients who consistently pay late
5. Services or project types where deposits should be required
6. Where my current terms create avoidable cash strain
7. Whether late fees are worth using for my client mix

Then draft:

1. A cleaner payment terms paragraph for future proposals
2. A deposit requirement paragraph where appropriate
3. A note for one or two chronic late payers, matched to the relationship

Mark all notes HOLD. Do not send anything.

Prompt 13

Review my past and completed clients using invoices, payment records, email history, client notes, meeting records, project files, results, complaints, testimonials, and repeat work.

Rank clients into three tiers:

Tier 1: paid well, paid on time, got strong results, low drama, good relationship, likely to buy again or refer

Tier 2: solid clients with some friction, smaller budgets, slower timelines, or less obvious expansion potential

Tier 3: small, slow, difficult, low-margin, or high-attention clients

For Tier 1 and Tier 2, design two high-ticket offers grounded in what these clients actually asked for, complained about, wanted next, or paid for before.

For Tier 3, design one lower-touch offer between $500 and $1,000 that helps them without consuming too much of my time.

For each offer, include:

1. Offer name
2. Promise
3. Price
4. Who it is for
5. Why this tier would say yes
6. Evidence from real emails, invoices, notes, or projects
7. What not to include so the scope stays controlled

Do not invent demand. If the evidence is weak, say so.

Prompt 14

Read my inbound emails from the last year.

Find every time someone asked for something I do not officially sell, including:

- "Do you also do X?"
- "Can you help with Y?"
- "Would you be able to look at this?"
- One-off favors
- Small requests I handled manually
- Repeated advice I gave for free
- Problems people asked about before or after buying

Group the requests by theme.

If three or more people asked for the same thing, treat it as possible offer demand.

For each candidate, show:

1. What people asked for
2. The real quotes proving demand
3. Who asked
4. Whether they were prospects, clients, or past clients
5. Suggested offer format
6. Suggested price based on comparable work I have billed before
7. Whether it should be high-ticket, low-ticket, retainer, workshop, audit, or add-on

Do not create an offer unless the demand is visible in the evidence.

Prompt 15

Review my last ten proposals and project files.

Find the work I keep scoping from scratch even though the core is basically the same.

Identify:

1. Steps that appear in almost every project
2. Deliverables that barely change
3. Parts that genuinely vary
4. Common client requests
5. Common delays
6. Revisions or scope creep patterns
7. What I actually charged
8. How long delivery really took

Then package the repeatable core as a fixed-scope, fixed-price offer.

Include:

1. Offer name
2. Who it is for
3. What is included
4. What is explicitly not included
5. Required client inputs
6. Timeline
7. Price based on historic billing
8. One-page sales description

The goal is simple: next time this request comes in, I send one page instead of writing a custom proposal from scratch.

Prompt 16

List everything I currently sell using my website, proposals, invoices, contracts, and sales emails.

Create an offer ladder from lowest price to highest price.

For each offer, include:

1. Name
2. Buyer
3. Price
4. Promise
5. Delivery model
6. Whether it appears active, outdated, confusing, or overlapping

Then identify gaps:

1. Where a buyer has no easy starting point
2. Where a happy client has nowhere to go next
3. Where two offers compete with each other
4. Where an offer attracts the wrong buyer
5. Where I am missing a high-ticket or recurring option
6. Where I have too many low-value offers

Propose the smallest set of changes needed to make the ladder work.

Every recommended offer must be grounded in real evidence from emails, invoices, proposals, or client demand.

Prompt 17

Find every client who completed a project and then came back within six months with questions, small requests, follow-up work, troubleshooting, extra advice, or another project.

Use invoices, emails, support threads, meeting notes, and project records.

That pattern may indicate retainer demand.

For each client, show:

1. Original project
2. Follow-up requests
3. Whether the follow-up was paid or unpaid
4. Time/attention consumed
5. What recurring need appears to exist

Then design a retainer offer:

1. What is included monthly
2. What is excluded
3. Monthly price
4. Minimum term
5. Best time to offer it
6. Which clients should receive the offer first

Draft the pitch email for the three past clients most likely to say yes.

Use relationship-specific details from the record.

Mark all drafts HOLD.

Prompt 18

Review my current active clients.

For each client, read recent emails, notes, meeting records, proposals, and project files.

Find adjacent needs they have mentioned in passing. Look for:

- Problems they said they would handle later
- Requests outside current scope
- Repeated questions
- Bottlenecks slowing the current project
- Things they need after this engagement ends
- Risks they do not appear to have solved yet

For each client, show:

1. Client name
2. Current engagement
3. Adjacent need
4. Exact signal or quote
5. Natural expansion offer
6. Best moment to raise it
7. One or two sentences I can say on the next call

Do not write pitch emails. Give me conversation openers only.

Prompt 19

Compare every service or offer I sell using real business records.

Score each offer on:

1. Revenue
2. Frequency of purchase
3. Delivery time
4. Email volume
5. Meeting load
6. Revision rounds
7. Scope creep
8. Client satisfaction signals
9. Profit per hour of attention
10. Strategic value

Find the offer that performs worst.

Make the case for whether I should:

- Kill it
- Reprice it
- Narrow the scope
- Turn it into a template/product
- Move it to a lower-touch delivery model

Show the numbers and evidence.

Then tell me what to do with existing clients on that offer.

If a transition note is needed, draft it and mark it HOLD.

Prompt 20

I am considering a new offer: [describe the offer].

Before I build anything, help me test whether people actually want it.

First, write a plain-language one-paragraph description of the offer. No hype.

Then search my email history, client notes, invoices, proposals, and past conversations to identify the ten warmest people for whom this offer appears relevant.

For each person, show:

1. Why they are a fit
2. What evidence supports that
3. Whether they are a client, past client, prospect, or referral partner
4. What specific pain or goal this offer connects to

Then draft a short personal note to each person asking one honest question: would this be useful, and what would make it a yes?

Make the tone personal, not mass marketing.

Mark all drafts HOLD.

End with a simple test rule: what level of positive response would justify building this, and what response would tell me not to build it.

Prompt 21

Create a one-page sales document for this offer: [offer name].

Use evidence from my business records.

Include:

1. The problem in the buyer's own words, pulled from real emails or notes
2. Who this is for
3. Who this is not for
4. What they get
5. What it costs
6. How long it takes
7. What happens after they say yes
8. Proof from real past results
9. Common objections and plain answers
10. Clear next step

Write it in my voice based on sent emails, not generic marketing voice.

Flag every claim you could not verify in my records.

Do not invent proof, testimonials, numbers, outcomes, or guarantees.

Prompt 22

Review my proposals, invoices, and contracts from the last two years.

Find the service most overdue for a price increase.

Show me:

1. Current price
2. Oldest price found
3. Average price over time
4. Scope changes over time
5. Delivery effort
6. Competitor or market comparison if available
7. Recommended new price
8. Why that number makes sense

Then draft:

1. The pricing language for the next proposal
2. A no-apology explanation of the new price
3. A recommendation for current clients on old pricing
4. Whether to grandfather anyone, and for how long
5. A two-sentence answer for when a current client asks why the price changed

Keep the language clear, direct, and calm. No long justification paragraph.

Prompt 23

Review my active client relationships using recent emails, meeting notes, calendar records, project management updates, support requests, and client notes.

Score each active client as:

- Warm
- Neutral
- Cooling
- At risk

Use real signals, including:

1. Reply speed changing
2. Shorter or colder messages
3. Missed meetings
4. Unanswered questions
5. Delayed approvals
6. Payment delays
7. Reduced enthusiasm
8. Fewer proactive updates
9. Threads where I failed to respond
10. Scope or expectation tension

Show the cooling and at-risk clients first.

For each one, give me:

1. Relationship score
2. Evidence
3. Likely reason
4. Best next action
5. Draft no-agenda check-in note in my voice

Mark all drafts HOLD.

Prompt 24

Based on everything you can access (emails, invoices, notes, meeting records, project status, payment history, and client relationship signals), tell me which one client I should personally call today.

Give me only one answer.

Include:

1. Client name
2. Why this is the highest-priority call
3. What is at stake
4. Three specific things to say on the call
5. One thing not to say
6. Whether the goal is retention, repair, upsell, collection, clarity, or appreciation

Do not give me a list of ten. Pick the one that matters most.

Prompt 25

I need to send a difficult email and I have been avoiding it.

Situation: [late payment / price increase / saying no to scope creep / ending an engagement / pushing back a deadline / correcting a misunderstanding / refund issue / boundary issue]

Client or contact: [name]

Before drafting, read our email history, project history, invoices, contracts, and notes so you understand the relationship and context.

Then draft two versions:

1. Softer version
2. Firmer version

Both should be:

- Direct
- Warm where appropriate
- Clear
- Not over-apologetic
- Not corporate
- Not defensive
- Specific about what happens next

Tell me which version you would send and why.

Mark both drafts HOLD.

Prompt 26

Find our best recently finished client project based on evidence in my files, emails, notes, invoices, results, testimonials, final messages, or before-and-after proof.

Pick one project.

Reconstruct the case study from the actual record.

Include:

1. Type of client or business, without naming them unless already approved
2. Where they started
3. What problem they had
4. Why they chose us
5. What we did
6. What changed
7. Proof of outcome
8. Client language or quotes where available
9. What made the work successful
10. What a similar client should learn from it

Flag any claim you cannot verify.

Draft a one-page case study.

Do not use the client's name unless I explicitly approve it.

Prompt 27

Review the email threads, documents, forms, checklists, contracts, and project files from the last three clients we onboarded.

Reconstruct what actually happens during the first two weeks.

Identify:

1. What we send
2. What we ask for
3. What clients often forget
4. What causes delays
5. What we repeat manually
6. What expectations are unclear
7. What would make onboarding smoother

Then build an onboarding pack:

1. Welcome email
2. What-to-expect one-pager
3. Client checklist
4. Internal checklist
5. Timeline for the first two weeks
6. FAQ based on real client confusion

Write the welcome email in my voice based on real sent emails.

Mark the email HOLD until approved.

Prompt 28

Go through my inbox and sent mail from the last 90 days.

Find every thread where someone showed buying intent and the conversation died.

Look for:

- Inquiries I never answered
- Warm replies I dropped
- People who asked for pricing
- People who requested a proposal
- "Let me think about it" threads
- Referral introductions that went nowhere
- Past clients asking about something new
- Prospects who said "circle back"
- People who opened a buying conversation but never got a clean next step

Rank the opportunities by likely value and likelihood of revival.

For each thread, show:

1. Contact
2. Company if available
3. Buying signal
4. Last message
5. Approximate value if known
6. Why it died
7. Recommended next step
8. Draft revival reply in my voice

Mark every draft HOLD.

Show me the list before anything is sent.

Prompt 29

Find every proposal, quote, estimate, or pricing email I sent that never received a clear yes or no.

Use email, CRM, proposal software, files, and accounting records.

For each open proposal, show:

1. Prospect or client
2. Amount
3. Date sent
4. Service or offer
5. Last thing either side said
6. How cold the opportunity is
7. Whether it should be followed up, closed out, or revived later

Then draft a follow-up matched to the situation:

- Recent proposal: light nudge
- 30+ days old: clear check-in
- 60+ days old: closing-the-loop message
- Very old but still relevant: honest revival note

Make it easy for them to say no. A fast no is better than slow silence.

Mark all drafts HOLD.

Prompt 30

Identify my three best clients using evidence, not memory.

Use invoices, payment history, project records, email tone, referrals, repeat work, testimonials, satisfaction signals, low-drama delivery, and profit per hour of attention.

For each best client, identify:

1. Industry
2. Company size or buyer type
3. Situation when they hired me
4. Trigger that made them buy
5. Pain they wanted solved
6. Words they used in their first email or buying conversation
7. What they valued most
8. Why they were easy or profitable to serve

Then write the shared profile across the best three clients.

Finally, list ten specific places, events, moments, platforms, referral sources, or buying triggers where I could find more people like them.

Do not say "networking events." Be specific.

Prompt 31

Build a list of past clients we have not worked with in over a year.

Use invoices, email history, CRM, project files, and notes.

Sort them into two lanes:

Lane 1: real relationship, good experience, worth a personal note

Lane 2: transactional client, lower relationship depth, lower-touch reactivation

For each person or company, show:

1. Last project
2. Last payment date
3. Last meaningful interaction
4. Relationship strength
5. Best reason to reconnect
6. Whether there is a likely next offer

Draft one reactivation note for each lane.

For Lane 1, reference something real from the relationship.

For Lane 2, keep it useful and low-pressure.

Do not make warm contacts sound like they are receiving a mass email.

Mark all drafts HOLD.

Prompt 32

Create a month of content ideas from real business evidence.

Read what you can access that shows my expertise:

- Sent emails where I explained something to a client
- Proposals
- Meeting notes
- Client questions
- Past posts
- Case studies
- Sales calls or transcripts
- Internal notes
- Training materials
- Website pages

Extract 20 content ideas.

Every idea must come from a real moment.

For each idea, include:

1. Source
2. Real client question, mistake, objection, or situation behind it
3. One-sentence point
4. First line written out fully
5. Best format: post, article, video, email, newsletter, or FAQ
6. Why my best buyer would care

Cut anything generic.

If it could appear on any competitor's blog, do not include it.

Prompt 33

Read my last 100 inbound emails from prospects and clients.

List the questions people actually ask before buying.

Then read my website.

Show me the gap between what buyers ask and what the website answers.

For the top five unanswered questions, draft the answer as it should appear on the website.

Use plain language and my real phrasing from sent replies where possible.

For each answer, include:

1. The buyer question
2. How often it appears
3. Whether the website answers it now
4. The answer I should add
5. Where it should go on the site
6. Why it matters for conversion
7. Whether it would help AI assistants understand and recommend my business

Write the answers so a human trusts them and a machine can quote them cleanly.

Prompt 34

Review this services page: [URL]

Read it as a skeptical buyer with three competitor tabs open.

Do not be polite.

Tell me:

1. What is unclear in the first five seconds
2. Where I talk about myself instead of the buyer's problem
3. Which claims have no proof
4. Where the offer is confusing
5. Where the page creates friction
6. What questions a serious buyer still has
7. Why someone might leave without contacting me

Then rewrite the page using proof from my actual files, emails, case studies, testimonials, proposals, results, and client language.

Flag every claim you cannot verify.

Do not invent numbers, testimonials, logos, outcomes, or guarantees.

Prompt 35

Compare my business against these three competitors:

1. [URL]
2. [URL]
3. [URL]

Review their websites and public presence, then review mine.

Give me a one-page competitive positioning brief.

Include:

1. What they claim that I do not
2. What I can prove that they cannot
3. Where their offers are clearer than mine
4. Where my offer is stronger but poorly explained
5. What buyer objections they answer better
6. What buyer objections I answer better
7. The positioning gap none of us clearly owns
8. The one change I should make first

Ground every point in something you actually read.

Use quotes where useful.

No generic strategy language.

Prompt 36

There is a process in this business that mostly lives in my head: [name the process].

Do not ask me to explain it step by step.

Instead, reconstruct the process from evidence.

Review the last five times this process happened using emails, files, documents, forms, client folders, project records, calendar events, invoices, notes, and messages.

Draft the process as it actually happens, including:

1. Trigger
2. First step
3. Owner
4. Tools used
5. Files involved
6. Client communication
7. Internal steps
8. Exceptions
9. Workarounds
10. Common mistakes
11. Final output
12. What confirms it is done

Then show me the draft and ask me only about the steps that left no paper trail.

After I answer, create a clean SOP that someone could follow if I were unreachable for two weeks.

Prompt 37

Build this week's Friday report from what you can actually access.

Use live systems first: accounting, payments, invoices, email, calendar, CRM, and project management tools. Use files or exports second.

Create a one-page report with:

1. Money received this week
2. Money still owed
3. Overdue invoices
4. Open proposals
5. Client threads that went quiet
6. Commitments I made in email this week that do not appear completed
7. Meetings or calls that require follow-up
8. One relationship I should pay attention to
9. One operational issue that needs fixing
10. The single most important thing for Monday morning

Show the source behind each important item.

Then save the instruction so that when I ask for "the Friday report," you produce this exact format again.

Prompt 38

Review this folder or shared drive: [folder/drive].

Do not move, delete, rename, archive, or overwrite anything yet.

First, map the mess.

Identify:

1. Duplicate files
2. Multiple versions of the same document
3. Old contracts
4. Files with unclear names
5. Files in the wrong place
6. Empty or unused folders
7. Sensitive files that need caution
8. Files that appear safe to archive
9. Files that should not be touched

Then propose a simple folder structure a new hire could understand on day one.

Show me the full move plan:

- What moves
- Where it moves
- What gets renamed
- What gets archived
- What stays untouched
- What requires my decision

Wait for my approval before making any changes.

After approval, execute the approved plan and give me a report of exactly what changed.

Prompt 39

Read this meeting transcript, recording, or notes: [attach or link].

Read the whole thing, not just the summary.

Extract:

1. Every commitment made
2. Who owns each commitment
3. Deadline or date mentioned
4. Implied deadline if no date was said
5. Open questions
6. Risks or ambiguities
7. Decisions made
8. Follow-up needed

Then draft a follow-up email to the attendees confirming what was agreed.

Write it in my voice based on my prior sent emails if available.

Flag anything ambiguous that will cause problems if nobody clarifies it.

Mark the email HOLD.

Prompt 40

I am about to make this decision: [describe decision].

Your job is to argue against it before supporting it.

First, review the relevant evidence from my business: financials, emails, client records, proposals, contracts, operations, team workload, calendar, past decisions, and anything else connected.

Then give me:

1. The three strongest reasons this decision could go wrong
2. Evidence from my own business supporting each risk
3. What I would need to believe for this decision to be right
4. What data is missing
5. The cheapest way to test the decision before fully committing
6. The cost of waiting
7. The cost of moving too fast

Then tell me what you would do and why.

Do not give me generic pros and cons. Use my actual situation.

Prompt 41

I think I need to hire someone, but I am not clear on the role.

Do not start with a job title.

Review the evidence of what is overflowing in the business:

- Sent emails
- Repeated tasks
- Late work
- Calendar load
- Client follow-up gaps
- Reports
- Admin work
- Project bottlenecks
- Files updated at the last minute
- Work I keep doing manually
- Things clients wait on

Tell me what role this actually is based on the work.

Then draft the job description.

Include:

1. Real role title
2. Why the role exists
3. Outcomes they own
4. Responsibilities
5. What they should not own
6. Tools they need to use
7. Three real scenarios from my business they would handle in week one
8. What good performance looks like in 30, 60, and 90 days
9. What experience matters
10. What experience does not matter

Tell me honestly whether any of this should be handed to you before I hire.

Prompt 42

I am handing you a large task: [describe task].

Work it through to the end as far as you safely can.

Rules:

1. Never send anything external.
2. Never publish anything.
3. Never delete, move, rename, or overwrite files.
4. Never commit me to a price, deadline, promise, meeting, or decision.
5. If information is missing, make a reasonable assumption only when needed to continue.
6. Mark every assumption clearly as [ASSUMPTION].
7. If something is too risky to assume, flag it and continue with the parts you can complete.
8. Keep a running list of sources used.
9. Check your own work before calling it finished.

When I return, give me:

1. The finished work
2. Every assumption you made
3. Anything you could not resolve
4. Anything that requires my approval
5. The sources you used
6. How you checked the output
7. The next three actions I should take

Do not ask me questions unless the task truly cannot continue without the answer.

Prompt 43

You have now seen my business: the connected tools, the files, the patterns in my email, where the money comes from, and where my attention goes.

Based on that evidence, design my agent roster: the five recurring agents that would save me the most hours or recover the most money.

Rank them by leverage.

For each agent, show:

1. Agent name
2. What it watches (which inbox, tool, or folder)
3. What it produces (drafts, a report, a ranked list)
4. How often it should run
5. The specific evidence from my business that justifies it
6. What could go wrong if it misfires
7. Risk level: low, medium, or high

Rules:

- Ground every agent in evidence you actually saw. Do not propose an agent for something that happens twice a year.
- Every agent starts draft-only: it prepares, I approve.

Then build the number one agent right now: write its standing instructions, set its schedule, and run it once in front of me so I can see exactly what will be waiting for me each morning.

Prompt 44

Take this task and turn it into an agent that runs on a schedule without me starting it: [name the prompt or describe the job].

Set it up completely:

1. Write the standing instructions, including my voice and my red lines
2. Choose the schedule based on how often the underlying thing actually changes: daily for inboxes, weekly for money, monthly for pricing
3. Decide where the output lands so I see it without hunting for it
4. Start it in draft-only mode: everything it produces waits for my approval

Then define its promotion path:

1. Track its accuracy as I approve or correct its output
2. After it has been right twenty times in a row on some category of item, propose moving just that category to automatic
3. Bring me the evidence when you propose the promotion, and I decide
4. Promotions are carve-outs, not blank checks: record each one in the memory file with its exact limits, and my permanent red lines (committing me to money or legal terms) are never up for promotion

Run it once right now as a test so I can see the output before it goes on the schedule.

Prompt 45

Build me an agent that makes sure nothing with money attached ever slips again.

Every morning it sweeps my email and open proposals for:

1. New inquiries that arrived since yesterday
2. Proposals with no reply after five business days
3. Anything I promised in writing that shows no evidence of being delivered

For each item it finds, it drafts the right response in my voice from my sent mail, all marked HOLD.

Then it hands me one short morning list:

1. What needs a decision
2. The drafts, ready to approve
3. Nothing else

If a morning is clean, the report is one line saying so.

Build it, run today's sweep right now, and show me the output before you put it on the schedule.

Prompt 46

Build me an agent that runs before I start work every Monday.

It produces one page:

1. Current receivables aging from my connected accounting tool
2. Payments that arrived last week
3. Chase drafts for anything genuinely overdue, cross-checked against payments received so it never chases someone who already paid
4. The one number I should be watching this week, with the reason in plain English

All drafts HOLD.

Build it and run the first one now, so Monday's version arrives in a format I have already approved.

Prompt 47

Look at the evidence of my business and find the place where I or my clients keep doing something manually that a simple tool would fix.

Look for patterns like:

- Quotes that take an hour to assemble from old proposals
- An intake process that lives in six back-and-forth emails
- A calculation I redo in my head every time someone calls
- A status question clients keep emailing me to ask

Propose the one tool worth building first. Describe it in plain terms:

1. What I would see
2. What my client would see
3. What manual work it replaces
4. What it would need to stay accurate

Then build a working version I can try today.

Rules:

1. It runs on my machine only. Nothing public.
2. It touches no live client data until I say so.
3. Take the time to check your own work before you show me. I care that it works, not that it was fast.

When I have used it and it holds up, we will talk about where it should live permanently.