The 10 prompts I actually use every week
Read this week
Every owner I work with asks me some version of the same question after a few weeks of using Claude or ChatGPT: "Yeah it's useful, but I keep using it for the same three things. What am I missing?"
Fair question. So this issue is the answer: the 10 prompts I actually use, in rotation, every week. Not "100 ChatGPT prompts to revolutionize your business" — you've seen those LinkedIn carousels. They're noise.
These are 10 prompts I personally run, multiple times a month, that produce real output I use. Every one of them comes from real work — my own admin life, the advisory work I do with SMB owners, the writing I do for this newsletter. Copy them. Paste them into Claude (Pro, $20/mo, is the version I use). Edit them for your business. Save the good ones in a note on your phone.
The exact wording matters more than people think. I'll explain why for each.
Skip this week
The "Ultimate ChatGPT Prompts" PDFs being sold on LinkedIn and Twitter for $19-$49.
I've bought four of them in the last year, just to see. Every single one was a list of 100-300 prompts written by somebody who clearly did not run a business, copy-pasted from older lists, with no context for when to use what. They are not worth the $19. The good prompts that actually move work forward are the ones you write for your own situation, edit over time, and re-run with small variations.
This issue is closer to a starter set than a finished product. Take what's useful, ignore the rest, write your own from there.
The 10 prompts
I'll group them by what they do for you. For each: the prompt itself, when to use it, and what makes the wording matter.
Decision-making prompts
1. The "am I missing something obvious" prompt
"I'm about to [describe decision] because [reasons]. Before I commit, what are the three most important questions I should answer first, and what's the obvious failure mode I might be ignoring? Be direct, not polite."
Use this before any decision that costs you more than a week of work to unwind. The "be direct, not polite" is the part most people skip. Without it, Claude hedges. With it, you get the answer.
2. The "argue the opposite" prompt
"I've decided to [decision]. Argue the strongest possible case against this decision as if you were a skeptical board member who's seen this go wrong before. Don't be balanced — make the best counterargument you can."
I use this before any decision that involves spending more than $10K or committing to something for more than 6 months. About a third of the time the counterargument is weak and I proceed. A third of the time it changes my mind. A third of the time it makes me modify the plan. All three are valuable.
Writing prompts
3. The "rewrite this email" prompt
"Here's an email I'm about to send: [paste]. Rewrite it to be (1) half as long, (2) clearer about what I'm asking the recipient to do, and (3) less likely to make them defensive. Keep my voice — don't make it sound corporate. Tell me what you changed and why."
The "tell me what you changed" part is the trick. It teaches you, over time, what your writing habits are. I've learned more about my own email style from this prompt than from 20 years of just hitting send.
4. The "first draft of the hard email" prompt
"I need to write an email to [person] about [situation]. Here's the context: [details]. The outcome I want is [outcome]. Draft three versions of the opening paragraph: one direct, one warm-then-direct, and one diplomatic. I'll pick which to build from."
Use this for the email you've been postponing for three days. The three versions are key — picking is faster than writing.
Document and data prompts
5. The "read this for me" prompt
"Read this entire document and tell me: (1) the three things that matter most, (2) anything that obligates me beyond what I might expect, (3) anything unusual for this type of document, and (4) three questions I should ask before I sign or agree. Quote specific language with page numbers."
We covered this last week. Worth restating. Use for every contract, lease, proposal, RFP, or significant document before you respond.
6. The "what's the customer actually saying" prompt
"Here are [number] customer reviews / survey responses / cancellation reasons: [paste]. Tell me: (1) the three things customers consistently praise, (2) the three things they complain about or hint at, (3) the gap between how they describe my business and how I describe it, and (4) the single most actionable change I should make based on this."
Run this every quarter on your last 50 reviews or survey responses. It's the cheapest market research you'll ever do.
Operational prompts
7. The "SOP from a transcript" prompt
"Below is a transcript of me explaining how to [process] to a new employee. Turn it into a written SOP with numbered steps, a 'common mistakes' section, and a 'when to escalate' section. Use plain language. Don't add steps I didn't mention."
Record yourself walking through a process on your phone. Transcribe it (Otter.ai, ChatGPT voice mode, even just Apple Voice Memos with their built-in transcription). Paste the transcript in. You'll have an SOP in 10 minutes that would take you 90 minutes to write from scratch.
8. The "decode the meeting" prompt
"Here's a transcript / my notes from a meeting with [who]: [paste]. Tell me: (1) what was decided, (2) what's still unresolved, (3) what was said but not actually agreed to (watch for soft language), and (4) what action items I committed to, even if I didn't explicitly say yes."
The "soft language" instruction is important. People walk out of meetings with different versions of what happened. Claude is good at flagging the "we should probably look into that" lines that one person heard as a commitment and the other person heard as a brush-off.
Sales and customer prompts
9. The "follow-up after silence" prompt
"I sent a proposal / quote / pitch to [prospect] on [date] for [opportunity]. I've heard nothing for [time]. Draft three follow-up emails: one short and direct, one offering something new (a question, a piece of information, a softer ask), and one that gracefully closes the door so they have to respond. Keep my voice."
Use this every two weeks for stalled opportunities. The third version (gracefully closing the door) is the one that gets replies more often than the others. Counterintuitive, but it works.
10. The "real objection" prompt
"Here's what a prospect said when I quoted them [number]: [paste their response]. Tell me: (1) what's the surface objection, (2) what's probably the real objection underneath it, (3) three questions I could ask that would surface the real concern without pressuring them, and (4) one response that addresses the real objection directly."
Use this after any quote or proposal that gets a soft no, a "let me think about it," or a long silence. You will almost always learn something about the deal you didn't see.
The stack
What I use to run these:
· Claude Pro — $20/mo. Primary tool. Better at reasoning and longer outputs than the alternatives.
· ChatGPT Plus — $20/mo. I use it as a second opinion on high-stakes decision-making prompts (#1 and #2). Run the same prompt through both, see where they agree and disagree.
· A notes app on your phone — Free. The good prompts you edit and reuse are worth far more than the ones in a PDF you bought.
What I skip: every "ultimate prompts" PDF currently in market.
Sign-off
The owners I work with who get real value out of AI are not the ones with the longest prompt libraries. They're the ones who took five prompts, modified them for their actual situation, and ran them every week for six months.
If you only do one thing this week: pick the three prompts above that fit something you're actually doing this week. Copy them into a note on your phone. Use them.
If you've got 20 minutes more: take the next email you're about to send and run it through prompt #3. Read what Claude changed and why. That's your free writing coach.
— Hank