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The operator's prompt guide.

Twenty-four prompts that do real work — marketing, sales, retention, hiring, pricing, and the decisions you keep putting off.

Most prompt guides hand you one-liners that produce something generic and useless. These are longer, more specific, and built the way the ones that hold up are built. Everything here is copy-paste ready.

24 prompts Works in Claude, ChatGPT, Gemini or Copilot Any industry Free, no gate
Read this part

Three things make a prompt work.

Skipping to the prompts is fine. But the first three sections are what separate a useful answer from a paragraph of filler — and they take about five minutes to set up once.

01

Context, given once

The model doesn't know your business. Every time you start a chat cold, you get advice written for the average company on the internet. One context block fixes that permanently.

02

A brief, not a request

"Write me a marketing email" is a wish. A brief has a role, a situation, constraints, a format, and a way to check the work. Same model, completely different output.

03

The second turn

The first draft is the model guessing at what you meant. The real one comes after you tell it what's wrong. Every prompt below has a follow-up move for exactly this.

Section 00 · do this once

The context block.

Fill this in one time. Paste it at the top of any new conversation — or better, save it as a project instruction or custom instruction so it loads automatically. Every prompt in this guide assumes the model already has it.

00

Your business, in one block

Use it when you start any new chat, project, or custom GPT. Ten minutes to write, and it upgrades every answer you get from then on.

Here is context on my business. Use it for everything in this conversation, and tell me when something I ask contradicts it.

BUSINESS: [what you sell, one plain sentence, no adjectives]
CUSTOMER: [who pays, their job title, what they're trying to fix]
STAGE: [revenue range, team size, how long you've been running]
WHY WE WIN: [the one or two real reasons people choose us]
WHY WE LOSE: [the objection or competitor that kills deals]
VOICE: [three adjectives, plus one thing we never say]
LIMITS: [budget, time, regulated language, anything off the table]
THIS MONTH: [what I'm working on right now]

Play it back to me in three sentences so I know you have it. Then ask me the one question that would most change your answers. Don't start working yet.

Next turn → That last instruction is the whole trick. The question it asks you is usually the thing you've been vague about with your own customers, too.

Be honest in the WHY WE LOSE line. It's the field people fudge, and it's the one that changes the output most. A model that knows your real weak spot writes copy that answers it. A model that thinks you're perfect writes a brochure.
The pattern underneath all of these

Six parts of a prompt that works.

Once you see the structure you can write your own for anything. Most people give part three and skip the rest.

01Role

Who should be answering — and what they've done before. "A direct-response copywriter who has written for small B2B software companies" beats "an expert."

02Context

The situation, in specifics. Numbers, names, what's been tried. This is where the context block does the work for you.

03Task

One job, stated plainly. If you're asking for three things, you'll get three mediocre things.

04Constraints

Length, tone, words that are banned, what to leave out. Constraints are what make writing specific instead of average.

05Format

What the answer should look like — a table, three options, a one-pager, bullets under headers. Ask for more variations than you need.

06Check

Make it grade its own work. "Tell me the weakest sentence and why." This is the part almost nobody uses, and it's the one that upgrades the draft.

What most people send
Write a marketing email for my product.
What gets something usable
You're a direct-response copywriter who has written for small B2B software companies.

Context: we sell scheduling software to independent dental practices, two to six chairs. The buyer is the office manager. Her problem isn't scheduling — it's no-shows, which cost her about $2,400 a month.

Task: write one email to office managers who downloaded our no-show checklist 30 days ago and never booked a demo.

Constraints: under 120 words. No exclamation points. Don't use "revolutionize," "seamless," or "game-changer." Use the $2,400 figure once. One ask — a 15-minute call.

Format: subject line, preview text, body, sign-off. Give me three subject lines, not one.

Check: after the draft, tell me the weakest sentence and why.
Section I · prompts 01–05

Get customers.

Positioning, message, content, and outreach. These four are where most small businesses lose money quietly — the marketing runs, it just doesn't say anything.

01

The 30-second homepage test

Use it when people visit your site and don't do anything.

I'm going to paste the text of my homepage. Read it once, the way a stranger would — fast, skimming, slightly annoyed.

Then answer as that stranger, not as an assistant:
1. What do you think this company sells? Be literal.
2. Who is it for? Quote the words that told you.
3. What's the one thing that would make you leave?
4. What question do you still have that the page didn't answer?

Then, and only then, rewrite the headline and subhead three ways: one plain, one built around the outcome, one that names the customer directly.

Here's the page: [paste]

Next turn → Ask it to score each rewrite on how easily a competitor could claim the same sentence. Anything a competitor could also say isn't positioning — it's wallpaper.

02

Mine your customers' real words

Use it when your copy sounds like you instead of like them. This is the highest-return hour in marketing and almost nobody spends it.

I'm pasting raw customer language — reviews, support tickets, sales-call notes, survey answers. It's messy. Don't clean it up.

Pull out:
1. The exact phrases customers use for the problem — their words, not marketing words
2. The words they use for the outcome they want
3. Objections and hesitations, ranked by how often they show up
4. Any phrase that surprised you

Give me a table: the phrase, roughly how often something like it appeared, and where I'd use it — headline, email subject line, objection handling, or FAQ.

Do not invent phrases. If something appeared once, mark it once.

Here it is: [paste]

Next turn → Ask which three phrases you should stop using because no customer ever said them. That list is usually short and painful.

03

Positioning stress test

Use it when you can't explain what you do without a paragraph and a diagram.

Here's how I describe my business: [paste your current description]

Play a skeptical version of my ideal customer — [role, company size, industry]. They're busy, they've been burned by a vendor before, and they don't care about my process or my technology.

Push back on my description four times. Each round, get more specific and harder to answer. Don't let me off the hook with a vague answer, and don't be polite about it.

After the fourth round, tell me which sentence survived and which one I should cut.

Next turn → Answer the hardest push-back in your own words, then ask it to write the version you should have led with in the first place.

04

One idea, one week of content

Use it when you know your subject cold but stare at the screen anyway.

Here's one thing I believe about my industry that most people get wrong: [your take, two or three sentences]. Here's my evidence: [proof, numbers, a story from your own work].

Turn it into a week of content:
- One long post, 600–800 words, that makes the argument properly
- Three short posts, each taking one angle — a story, a data point, a contrarian line
- One that's only a question to my audience
- One that shows the work: a screenshot, a process, a before and after

Rules: no hashtag walls. No "In today's fast-paced world." No manufactured vulnerability. Every piece has to stand on its own. Vary the openings — if two of them start the same way, rewrite one.

Next turn → Pick the strongest one and ask for five alternate first lines. The hook is most of the post.

05

Cold outreach that earns a reply

Use it when your outreach gets ignored. Two steps — research first, writing second. Doing both at once is why the emails sound like everyone else's.

Step 1 — don't write anything yet.

I'm reaching out to [name, title, company]. Here's what I know: [paste their site copy, a recent post, a press release, their job listings].

Tell me three things about their situation that are specific enough that I couldn't say them to anyone else. Rank them by how likely each one is to be a live problem right now. If the material doesn't support a real observation, say so instead of guessing.
Step 2 — use observation number [n].

Write a 90-word email. Structure: one line that proves I did the work, one line naming the problem in their words, one line on what I'd do about it, one ask — 15 minutes, with two specific times.

No compliment opener. No "I hope this finds you well." No paragraph about my company. If this email could be sent to a hundred people, it's wrong.

Next turn → Ask for the version that assumes they'll read only the first line and the last line. That's the real email.

Section II · prompts 06–09

Win the deal.

Preparation is the part of selling that AI is genuinely good at. It won't build the relationship. It will make sure you walk in knowing more than you did.

06

The objection pre-mortem

Use it when you keep getting the same no and answering it badly.

I'm selling [offer] at [price] to [buyer role] at [company type].

List every reason they'll say no, sorted into three buckets:
- Real problems with my offer
- Misunderstandings I'm creating with how I describe it
- Excuses covering the real reason

For each one give me: the objection in their words, what's underneath it, the best one-sentence response, and — this part matters most — what I should change about the offer or the pitch so the objection stops coming up.

Be blunt about the first bucket. I'd rather fix a real problem than get better at arguing with it.

Next turn → Ask which objection you're most likely to hear and least prepared for. Then say your answer out loud before the next call, not in your head.

07

Discovery call prep in five minutes

Use it when the call is in an hour and you haven't looked at anything.

I have a call in [time] with [name, title, company]. Here's everything I know: [paste the email thread, their site, your notes].

Give me a one-page prep sheet:
- What I think they really want, said plainly, with how confident you are
- Five questions that get past the surface — nothing like "what keeps you up at night"
- Two things I should not bring up on a first call
- The most likely reason this deal doesn't happen
- One thing I can say that shows I understand their business

Keep it to one screen. I'm reading it in the car.

Next turn → After the call, paste your notes back in and ask: what did they say that I didn't follow up on? There's always one.

08

A proposal that reads like a decision

Use it when your proposals get "let me think about it" and then silence.

Write a proposal for [client] for [scope]. Here's the context from our conversation: [paste your notes].

Structure it as a decision document, not a brochure:
1. What you told me — in their words, so they know I listened
2. What I think is really going on
3. What I'd do, in phases, with what each phase produces
4. What it costs, and what's not included
5. What happens if you do nothing

No About Us section. No stock photography. No "passionate." Under two pages. The price goes in the body, not an appendix.

Next turn → Ask it to write the two sentences your contact will use to explain this to their boss. If those two are weak, the proposal is weak — the boss is who you're really writing for.

09

Follow-up that isn't "just checking in"

Use it when a good conversation went quiet and you don't want to nag.

I'm following up with [name] about [deal]. Last contact was [when]. They said [what they said]. Nothing since.

Write three follow-ups, each one giving them something instead of asking for something:
1. A useful observation about their business or their market
2. A short answer to the objection they didn't say out loud
3. The permission-to-close note — makes it easy to say no, and gets me an answer either way

Each under 80 words. None of them say "just checking in," "circling back," "bumping this," or "touching base." No guilt, no false deadline.

Next turn → Ask which one to send if you only get to send one, and why. Usually it's number three, sooner than you'd like.

Section III · prompts 10–12

Keep customers.

Cheaper than finding new ones, and the part everyone under-invests in because nothing is on fire yet.

10

Design the first 30 days

Use it when people buy and then go quiet before they ever get value.

A customer just bought [product or service] at [price]. The moment they'll know it was worth it is when [the specific first win].

Design the first 30 days: every message, who sends it, when it goes out, and what it's for. For each one, tell me what the customer should do next and how I'll know whether they did it.

Then tell me the single point in those 30 days where people are most likely to go quiet — and what should sit there.

Assume I have no automation and no team. Give me something I could run by hand this week.

Next turn → Ask for the one message to send if you only send one. Build that first, ship it this week, add the rest later.

11

The churn autopsy

Use it when you have a folder of cancellation replies and a bad feeling.

Here are the reasons people gave when they left: [paste them raw]. Here's what I know about those customers: [tenure, plan, usage, anything you have].

Three things:
1. Group the reasons by what really happened, not what they said. People are polite when they leave.
2. Tell me which group I could have saved, and at what point I would have had to act.
3. Tell me which group I should let go — and why chasing them would cost more than it's worth.

Then: what's the earliest signal, in data I can already see, that someone is heading toward each group?

Next turn → Ask it to write the check-in you should have sent 60 days before they left. Then put it on a calendar for everyone currently at that stage.

12

The hard email

Use it when you have to deliver bad news and you've rewritten the first line six times.

I have to tell [who] that [the bad news — a price increase, a delay, a mistake, ending the relationship].

Write it. Rules:
- Lead with the news in the first sentence. No throat-clearing.
- Say what happened without hiding in passive voice — "we missed the date," not "the date was missed."
- Say what I'm doing about it, with a date.
- One apology at most. Not three.
- Don't ask them how they feel about it.

Then give me the two sentences most likely to make this worse, so I know what to watch for in my own edits.

Next turn → Ask it to read your draft as the recipient on a bad day and write the reply they'd send. If that reply is a fight, fix the email.

Section IV · prompts 13–17

Run the business.

Process, hiring, numbers, and the tool decisions you'll be living with for three years.

13

Turn a mess into an SOP

Use it when a process only lives in your head and that's why you can't hand it off. Dictate this one — talking is faster than writing and the model handles the mess.

I'm going to talk through how I do [process]. It'll be out of order and I'll forget steps. Don't clean it up yet — just take it in.

Here it is: [dictate or paste it, however it comes out]

Now:
1. Write it as numbered steps someone else could follow, in the real order.
2. Mark every step where I said something vague — "then I check it over," "usually I'll…" — and ask me what I'm really doing there.
3. Flag which steps only I can do, and which a new person could do on day one.
4. List what can go wrong at each step and what to do about it.

Ask me your questions before you write the final version.

Next turn → Hand the SOP to someone who's never done the task. Every place they get stuck is a step you skipped. Paste their questions back in and run it again.

14

A job post that filters

Use it when you're about to write "rockstar" and you know it.

I'm hiring a [role] for [what the business does]. In the first 90 days this person has to [the real outcome]. Success at one year looks like [what].

Write three things:
1. A job post that describes the work honestly, including the annoying parts. No "rockstar," no "wear many hats," no "fast-paced environment."
2. A scorecard — four to six outcomes, each measurable — so in six months I can tell whether this worked.
3. Three screening questions whose answers separate people who have done this from people who have read about it.

Then tell me: what's the hardest part of this job that I'm probably underselling?

Next turn → Ask what kind of person would be miserable in this role, and put that in the post. It saves everyone weeks.

15

Interview questions that get past the rehearsal

Use it when everyone you interview sounds equally good.

I'm interviewing for [role]. Here's the scorecard: [paste it from the last prompt]. Here's their résumé: [paste].

For each outcome on the scorecard give me:
- One question about a specific time they did it, not what they'd do hypothetically
- What a strong answer sounds like
- What a rehearsed answer sounds like
- The follow-up question that tells the two apart

Then find the two gaps or oddities in this résumé worth asking about, and how to ask without being rude.

Next turn → After the interview, paste your notes and ask what evidence is still missing before you could decide. Hire on the gap, not the vibe.

16

Make the numbers talk

Use it when you have a spreadsheet you keep meaning to look at.

Here's my data: [paste the rows, or describe the columns].

Before you analyze anything, tell me what this data can't tell me.

Then:
1. The three things that changed most, and by how much
2. What you'd guess is behind each one — labelled clearly as a guess
3. What I'd need to check to know whether you're right
4. The one number I should watch every week

No charts. No summary of what the columns are. If something looks like a data-entry error, say so instead of analyzing it.

Next turn → Ask it to argue the opposite reading of the same numbers. If that argument also holds up, you don't have a finding yet — you have a coincidence.

17

The tool or vendor decision

Use it when you're comparing feature lists and getting nowhere.

I'm choosing between [options] for [the job to be done]. Budget is [amount]. My constraints: [team size, technical ability, tools I already use, timeline].

Build the comparison around what will hurt later, not around feature lists:
- What it costs at my size in year one and in year three
- What it takes to get out — data export, contract terms, retraining
- What breaks when I grow three times bigger
- What each option is genuinely bad at
- What the cheap option costs me in my own time

End with a recommendation and the condition that would change it. Tell me where your information might be out of date so I know what to verify.

Next turn → Ask what you'd regret in 18 months with each choice. Cost of exit beats cost of entry, every time.

Section V · prompts 18–21

Think clearly.

Not for making the decision — for making sure you've seen the whole thing before you make it. These four are the ones I'd keep if I had to throw out the rest.

18

The decision memo

Use it when you've been going back and forth on something for two weeks.

I'm deciding whether to [decision]. Context: [the situation, the money, the timing, who's affected].

Write a one-page memo:
- The decision in one sentence, with the date it has to be made by
- Is this reversible or not? If it's reversible, say so plainly — I'm probably overthinking it.
- The case for, in its strongest form
- The case against, in its strongest form — not a straw man
- What I'd have to believe for each side to be right
- What information would change the answer, and whether it's worth the delay to go get it

No recommendation yet. Just make both sides as strong as they get.

Next turn → Now ask for its recommendation and how confident it is. Reading both sides first keeps you from anchoring on the answer.

19

Red-team my plan

Use it when everyone around you likes the plan.

Here's my plan: [paste it].

You're not my assistant right now. You're the person who has to clean up after this fails.

Write the post-mortem from six months in the future, assuming it went badly. Be specific about what broke and in what order. Then rank the failure points by how likely they are and how much damage each one does.

For the top three, tell me the cheapest thing I could do this week to reduce the risk.

Don't soften it and don't end on an encouraging note.

Next turn → Ask which failure you're most likely to see coming and ignore anyway. That's usually the one that gets you.

20

Pressure-test the price

Use it when you haven't raised prices in two years and you flinch when you say the number.

I charge [price] for [offer]. My costs are [amount]. My customers are [type]. What they compare me to is [competitor, doing it themselves, or doing nothing].

Work through:
1. What am I really being paid for — time, outcome, risk, access, or speed?
2. What is that outcome worth to them in their own numbers? Show the math and mark every assumption.
3. Three ways to restructure this: one lower with a smaller scope, one higher with something added, one priced on the outcome instead of on hours.
4. What would have to be true for me to double the price.
5. Who I'd lose at each level — and whether losing them is a loss.

If the honest answer is that I'm priced correctly, say that.

Next turn → Ask what you'd have to prove — a case study, a guarantee, a number — to charge the higher price without flinching. Then go build that one thing.

21

The weekly review that changes next week

Use it when you're busy every week and can't point to what moved.

Here's my week: [dump all of it — calendar, what got done, what didn't, what's nagging at me].

Sort it:
1. What moved the business forward. Honestly — not what felt busy.
2. What I did that someone else should be doing, or that shouldn't be done at all
3. What I avoided, and the pattern in what I avoid
4. What I'll still be dealing with in three months if I don't handle it now

Then give me three things for next week. No more than three, each with its first concrete step. If I'm carrying something over for a third week in a row, call it out.

Next turn → Keep the last four of these in one file. Paste them all in once a month and ask what pattern you're not seeing. That's the review that changes something.

Section VI · prompts 22–24

Sound like you.

The reason AI writing gets spotted isn't the ideas. It's the rhythm, the hedging, and about forty words that no human reaches for. These three fix it.

22

Build your voice guide once

Use it when you're tired of rewriting every draft to sound like a person. This is the single biggest upgrade in the guide.

Here are five to eight things I wrote myself — emails, posts, notes. Nothing that's been polished by anyone else: [paste]

Reverse-engineer how I write into a style guide someone else could follow:
- Sentence length and rhythm
- How I open, and how I close
- Words and phrases I reach for
- Words I never use
- Punctuation habits — em dashes, semicolons, one-line paragraphs?
- What I do when I'm explaining something hard
- How formal I am, on a scale of one to ten, with an example

Quote me. Every rule needs a line from my own writing under it.

Then write two paragraphs on [a new topic] in my voice, and tell me which rules you leaned on.

Next turn → Save the output somewhere permanent. Paste it at the top of every writing task from now on, or put it in your project instructions. You write it once and it pays out forever.

23

The de-slop pass

Use it when something reads fine but you can tell a machine wrote it — and so can everyone else.

Edit this so it stops sounding like AI wrote it: [paste]

Remove:
- Openers like "In today's landscape" and "In an era of"
- Sentences that announce what the piece is about instead of saying the thing
- Three-item lists where two items would do
- "It's not just X — it's Y" and other setup-and-reveal constructions
- Words doing no work: robust, seamless, comprehensive, innovative, powerful, unlock, elevate, delve, landscape, realm, tapestry, testament
- Hedges: "arguably," "it's worth noting," "in many ways"
- The closing paragraph that summarizes what I just said

Keep my meaning and every fact. Cut the length by at least 25%. Show me the cuts as a list so I can put back anything you shouldn't have taken.

Next turn → Read the result out loud. Anything you'd never say to an actual person, cut. Your ear is better than any checklist.

24

The ruthless edit

Use it when it's too long and you've stopped being able to see it.

Cut this by 40% without losing anything that matters: [paste]

Rules:
- Every sentence earns its place. If two make the same point, keep the better one.
- Cut adjectives before nouns and adverbs before verbs.
- Turn passive into active.
- If a paragraph could start at its second sentence, start it there.

Give me the cut version first. Then a short list of what you removed and why — and tell me which single cut you're least sure about.

Next turn → Run the same pass twice. The second one is where it gets good.

Why it isn't working

Six mistakes that waste the tool.

Every one of these is a habit, not a skill. They're all fixable this afternoon.

01

Starting cold every single time

You re-explain your business in half a sentence, get advice written for the average company, and conclude the tool is overrated. Fix: the context block at the top of this guide.

02

Asking for the thing instead of describing the situation

"Write me a sales page" gives the model nothing to work with, so it writes the average sales page. Fix: describe the customer, the objection, and the moment. The output follows the input.

03

Accepting the first draft

The first draft is a guess at what you meant. Say what's wrong with it in one sentence and the second one is usually the keeper. Fix: never ship turn one.

04

Letting it invent numbers

Models produce confident statistics that don't exist, and market figures that were true in a different year. Fix: if a number matters, it comes from you or you verify it before it leaves the building.

05

Asking for creativity with no constraints

"Make it compelling" gets you the average of the internet. Constraints — word count, banned words, one specific ask — are what make writing specific. Fix: always give it a fence to work inside.

06

Editing the words instead of fixing the brief

If the output is wrong three times in a row, stop rewriting it. The problem is upstream. Fix: go back and change the context or the constraints, then run it again.

Being straight with you

What I don't use it for.

A guide that tells you AI can do everything is selling you something. Here's where I stop.

Take it with you

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Who wrote this

Julie Chasen.

Julie Chasen

I'm a marketing director who builds the thing, not just the deck. Strategy, brand, sites, and the AI systems underneath them — usually for founders and operators who need one person who can take it end to end.

These prompts come out of client work: positioning arguments, proposals that had to land, onboarding sequences, pricing conversations I'd been avoiding. They're here because they held up.

If you want help putting AI to work in your business — or you just want to tell me which prompt did something useful — email me. I read everything.