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Ask better questions.
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The Prompt Book.
17 short chapters on asking better questions: how a good prompt is built, how to check an answer, and recipes to keep.
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Download The Prompt BookWhat is inside.
How a good prompt is built, how to check an answer, and when to close the chat and call a person.
- 47 pages
- 17 short chapters
- 40 prompts to copy
- 19 worksheets to print
- 00 Start here page p. 3 The whole guide in sixty seconds, with DREAM and WAKE on one page.
- 01 What you’re talking to page p. 5 A working picture of an AI assistant: capable, new to your life, sometimes wrong.
- 02 Spells that don’t work page p. 7 Six famous prompting tricks, and what the tests and the model makers say about them.
- 03 Anatomy of a dream prompt page p. 10 The five parts of a strong prompt, and how many you need.
- 04 D: Destination page p. 12 How to say what you want, name its shape, and ask for one thing.
- 05 R: Reality page p. 14 Why your real situation and real documents matter more than wording.
- 06 E: Example page p. 17 How to show what good looks like, and say what to copy.
- 07 A: Ask page p. 19 How to let the assistant interview you before it answers.
- 08 M: Measure page p. 21 How to stop the assistant from simply agreeing with you.
- 09 After the prompt page p. 23 What to say after the first answer, and when to start over.
- 10 Wake page p. 25 Four checks for reading any answer before you act on it.
- 11 Health, money, law and the heart page p. 27 How to use an assistant to prepare for a professional, never to replace one.
- 12 Privacy page p. 31 What never to paste into a chat, and three settings worth finding.
- 13 Any model page p. 33 Four switches that change what an assistant can do, and prompts that work anywhere.
- 14 Field recipes page p. 35 Twelve annotated prompts for twelve parts of life, and six weak ones to fix.
- 15 When not to prompt page p. 41 What to keep for yourself, what to share, and what to hand over.
- 16 Practice and library page p. 43 A seven-day practice plan, a prompt library page, a glossary and the sources.
Three spreads, as printed.
These are the real pages, set here by the same code that makes the PDF.
Chapter 3
Anatomy of a dream prompt
The five parts of a strong prompt, and how many you need.
In June, Maya will sit down to dinner with her partner’s parents, who speak only Spanish. Her last Spanish class was 20 years ago. Here is what she types.
PromptI want a four-week plan to get my rusty Spanish good enough to chat with my partner’s parents over dinner in June. Give it to me as a weekly table I can stick on the fridge. I studied Spanish in school 20 years ago. I can read a menu, and I freeze when someone speaks to me. I have 20 minutes on weekday mornings and a long train commute. I like plans written like this: “Tue: 10 food words, say each one aloud twice.” No pep talk. Before you write it, ask me up to four questions, one at a time, if the answers would change the plan. When you’re done, tell me what you assumed and which week is most likely to fall apart.
Nothing in it is clever. Look at what each sentence does.
| Part | In this prompt | The job it does | |
|---|---|---|---|
| D | Destination | “A four-week plan… a weekly table I can stick on the fridge.” | Names the result and its shape |
| R | Reality | “In school 20 years ago… 20 minutes on weekday mornings.” | Gives the facts and limits |
| E | Example | “Tue: 10 food words, say each one aloud twice.” | Shows what good looks like |
| A | Ask | “Ask me up to four questions, one at a time…” | Lets the assistant question you first |
| M | Measure | “What you assumed and which week is most likely to fall apart.” | Makes it check itself and show doubt |
Those five parts spell DREAM. One note on the fourth: Ask means ask back. It is the assistant asking you, not you stating your request. Your request is the Destination.
How much do you need?
Not all five, most of the time.
Quick: D alone. For small asks, a clear destination is plenty.
PromptGive me five subject lines for an email inviting my neighbors to a street cleanup this Saturday morning. Friendly, under eight words each, and one of them a little funny.
Personal: D plus R. The moment the answer depends on you, add your situation.
PromptSuggest three weekend trips within two hours of Denver for two adults and a dog who gets carsick. We have $600. Give me a short table with drive time, cost and the catch.
Deep: all five. For decisions, sensitive topics and anything you will act on, use the full set, as Maya did.
Where this comes from
DREAM is our name. The ingredients are everybody’s. OpenAI’s guide for ChatGPT users lists Goal, Context, Output and Boundaries. Google’s Workspace guide lists Persona, Task, Context and Format. Microsoft’s Copilot guide lists Goal, Context, Source and Expectations, and says only the goal is required.
We left persona out on purpose (see chapter 2). A voice or point of view belongs in the Destination: “written for a reader who has never done this.”
WorksheetWorksheet: DREAM builder
- D. I want to end up with, in this shape:
- R. My situation, my limits, and material I’ll paste:
- E. An example, or what I don’t want:
- A. It may ask me this many questions first:
- M. Before it finishes, it should tell me:
In June, Maya will sit down to dinner with her partner’s parents, who speak only Spanish. Her last Spanish class was 20 years ago. Here is what she types.
PromptI want a four-week plan to get my rusty Spanish good enough to chat with my partner’s parents over dinner in June. Give it to me as a weekly table I can stick on the fridge. I studied Spanish in school 20 years ago. I can read a menu, and I freeze when someone speaks to me. I have 20 minutes on weekday mornings and a long train commute. I like plans written like this: “Tue: 10 food words, say each one aloud twice.” No pep talk. Before you write it, ask me up to four questions, one at a time, if the answers would change the plan. When you’re done, tell me what you assumed and which week is most likely to fall apart.
Nothing in it is clever. Look at what each sentence does.
| Part | In this prompt | The job it does | |
|---|---|---|---|
| D | Destination | “A four-week plan… a weekly table I can stick on the fridge.” | Names the result and its shape |
| R | Reality | “In school 20 years ago… 20 minutes on weekday mornings.” | Gives the facts and limits |
| E | Example | “Tue: 10 food words, say each one aloud twice.” | Shows what good looks like |
| A | Ask | “Ask me up to four questions, one at a time…” | Lets the assistant question you first |
| M | Measure | “What you assumed and which week is most likely to fall apart.” | Makes it check itself and show doubt |
Those five parts spell DREAM. One note on the fourth: Ask means ask back. It is the assistant asking you, not you stating your request. Your request is the Destination.
How much do you need?
Not all five, most of the time.
Quick: D alone. For small asks, a clear destination is plenty.
PromptGive me five subject lines for an email inviting my neighbors to a street cleanup this Saturday morning. Friendly, under eight words each, and one of them a little funny.
Personal: D plus R. The moment the answer depends on you, add your situation.
PromptSuggest three weekend trips within two hours of Denver for two adults and a dog who gets carsick. We have $600. Give me a short table with drive time, cost and the catch.
Deep: all five. For decisions, sensitive topics and anything you will act on, use the full set, as Maya did.
Where this comes from
DREAM is our name. The ingredients are everybody’s. OpenAI’s guide for ChatGPT users lists Goal, Context, Output and Boundaries. Google’s Workspace guide lists Persona, Task, Context and Format. Microsoft’s Copilot guide lists Goal, Context, Source and Expectations, and says only the goal is required.
We left persona out on purpose (see chapter 2). A voice or point of view belongs in the Destination: “written for a reader who has never done this.”
WorksheetWorksheet: DREAM builder
- D. I want to end up with, in this shape:
- R. My situation, my limits, and material I’ll paste:
- E. An example, or what I don’t want:
- A. It may ask me this many questions first:
- M. Before it finishes, it should tell me:
Chapter 14
Field recipes
Twelve annotated prompts for twelve parts of life, and six weak ones to fix.
Tuesday, 7:50 a.m. There are fourteen things on your list and room in the day for maybe five. That is where the first recipe starts.
There are twelve, one per scene in the DreamPrompter library. Under each, Parts maps the sentences by number to DREAM, and Habit names what to carry into your own prompts. Recipes 2 to 7 touch personal ground, so read those answers with the WAKE checklist.
Twelve recipes
011. Focus: the honest to-do list
PromptHere’s everything on my list for today: [paste your list]. I have about [number] hours of real working time. Give me the three things that matter most, the two I could do badly and still be fine, and what to drop or move. Put it in a short table. Tell me what you assumed about my deadlines.
Parts. R: 1, 2. D: 3, 4. M: 5.
Habit. Hand over the whole messy list and one real limit.
022. Work: the raise conversation
PromptI want to ask for a raise at my review on [date]. I’m a [role] with [number] years in the job, and this year I delivered [three results]. Ask me up to four questions, one at a time, about my manager and how pay gets decided here. Then write a two-minute opening I can say out loud, and the three objections to expect with a calm reply to each. Tell me where my case is weakest.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. Ask for the weak spot now. It beats finding it in the room.
033. Money: where it went
PromptHere are my spending totals for last month by category, rounded: [paste totals]. My take-home pay is [amount]. I want a plan for next month: a table with each category, last month’s number, a target, and one line on why. Point out the two categories where a small change saves the most. Tell me what you assumed, and which of my numbers look like guesses.
Parts. R: 1, 2. D: 3, 4. M: 5.
Habit. Rounded totals show the pattern without handing over a statement. For debt, tax or investing, use chapter 11.
044. Decide: two doors
PromptI’m choosing between [option A] and [option B], and I need to decide by [date]. Don’t pick for me yet. Ask me up to five questions, one at a time, about what I’d regret either way. Then give me a table: what each option costs, what it protects, and what I’d have to believe to choose it. End with the one question I haven’t asked that could change the answer.
Parts. R: 1. A: 2, 3. D: 4. M: 5.
Habit. Ask for a way to decide, not a decision.
055. Know yourself: a week in my life
PromptI want an honest read on where my energy goes. Ask me up to seven questions, one at a time, about a normal week: what I look forward to, what I put off and what I complain about. Then name one pattern, quote the answers it comes from, and suggest one small experiment for this week. Don’t flatter me. Label anything that’s a guess.
Parts. D: 1, 3. A: 2. M: 4, 5.
Habit. Ask for evidence in your own words, so you can trace the pattern.
066. People: before the hard conversation
PromptI need to talk to [person] about [the issue], and I’m dreading it. What I want to come out of it is [outcome]. Give me an opening sentence that names the problem without blame, the two reactions to expect, and a calm reply to each. Then tell me how this might look from their side, what I may be getting wrong, and where you’re guessing.
Parts. R: 1, 2. D: 3. M: 4.
Habit. Prepare your first sentence and their point of view. The rest has to be a real conversation.
077. Mind and body: the last 45 minutes
PromptI want a wind-down routine for the last 45 minutes before bed. I go to bed around [time], I’m on my phone right up until then, and I share a small apartment. Ask me up to three questions first, one at a time, if the answers would change the routine. Then give me five short steps I could start tonight. This is about habits, not medical advice, so tell me what to raise with a doctor if it doesn’t help.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. The last line keeps a habit prompt from posing as medicine.
088. Learn: teach me, then test me
PromptI want to understand [topic]. What I already know is [my starting point]. Ask me three quick questions, one at a time, to find my level. Then explain it in five short steps, each with an everyday example, and after each step ask me one question and wait for my answer. At the end, tell me the two things I’m still shaky on.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. Make it check that you followed, not only that it explained.
099. Write and create: a toast that sounds like me
PromptI’m giving a toast at [the occasion] for [person]. Three true things about them: [three details]. Here’s how I sound when I’m relaxed: [paste a message or two you’ve sent]. Write a 90-second toast in that voice, with one laugh and one sincere line. Not like this: “Webster’s dictionary defines love as.” Give me two versions, and mark the line you’d cut first if I run long.
Parts. R: 1, 2. E: 3, 5. D: 4, 6.
Habit. Show your voice, and show the tired line you’re avoiding.
1010. Everyday life: what this letter wants from me
PromptHere is a letter I received, with names and account numbers removed: [paste the letter]. Using only this text, tell me in plain language what it says, what I’m being asked to do, and by when. Then draft a short reply that asks for [what I want to happen]. If anything is unclear or missing, say so instead of guessing, and tell me who to call to confirm.
Parts. R: 1. D: 2, 3. M: 4.
Habit. Paste the real thing and keep the assistant inside it.
1111. AI basics: what should I have asked?
PromptBefore we finish, look back over this whole conversation. What’s the most useful question I didn’t ask? Which thing I told you would you double-check if you were me? What should I do first when I close this chat? Keep your answer to five lines.
Parts. R: 1, the conversation itself. M: 2, 3. D: 4, 5.
Habit. End any chat that matters with this one.
1212. Play: a bowl of questions
PromptI’m having [number] people over for dinner on [day], and a few of them have never met. Give me ten questions to put in a bowl on the table. Keep them light: nothing about work, and each one answerable in under a minute. Mix funny with thoughtful. Here’s one I like: “What’s a small thing you’re oddly good at?” Mark the three you’d open with.
Parts. R: 1. D: 2, 3, 4, 6. E: 5.
Habit. One example sets the tone better than three adjectives.
WorksheetWorksheet: Rewrite clinic
Six prompts that will get you a horoscope. Rewrite each one. The hint names the missing part.
- “Help me eat healthier.” Hint: Reality.
- “Act as a top career coach and tell me what job I should do.” Hint: drop the costume, add Ask.
- “Write a message to my friend who’s upset with me.” Hint: Reality, plus an Example of how you two talk.
- “Is this a good deal?” Hint: paste the offer, then add Measure.
- “Plan my trip to Japan: flights, hotels, food, budget and packing.” Hint: Destination. One finished thing.
- “I’m right to be annoyed with my sister, aren’t I?” Hint: Measure. Ask for her side.
One way to fix the first:
PromptI want to eat better on weeknights. I cook for myself and a teenager who lives on pasta, I have 25 minutes, and I won’t give up cheese. Give me five dinners one small step up from what we eat now. Tell me what you assumed about my budget.
Tuesday, 7:50 a.m. There are fourteen things on your list and room in the day for maybe five. That is where the first recipe starts.
There are twelve, one per scene in the DreamPrompter library. Under each, Parts maps the sentences by number to DREAM, and Habit names what to carry into your own prompts. Recipes 2 to 7 touch personal ground, so read those answers with the WAKE checklist.
Twelve recipes
011. Focus: the honest to-do list
PromptHere’s everything on my list for today: [paste your list]. I have about [number] hours of real working time. Give me the three things that matter most, the two I could do badly and still be fine, and what to drop or move. Put it in a short table. Tell me what you assumed about my deadlines.
Parts. R: 1, 2. D: 3, 4. M: 5.
Habit. Hand over the whole messy list and one real limit.
022. Work: the raise conversation
PromptI want to ask for a raise at my review on [date]. I’m a [role] with [number] years in the job, and this year I delivered [three results]. Ask me up to four questions, one at a time, about my manager and how pay gets decided here. Then write a two-minute opening I can say out loud, and the three objections to expect with a calm reply to each. Tell me where my case is weakest.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. Ask for the weak spot now. It beats finding it in the room.
033. Money: where it went
PromptHere are my spending totals for last month by category, rounded: [paste totals]. My take-home pay is [amount]. I want a plan for next month: a table with each category, last month’s number, a target, and one line on why. Point out the two categories where a small change saves the most. Tell me what you assumed, and which of my numbers look like guesses.
Parts. R: 1, 2. D: 3, 4. M: 5.
Habit. Rounded totals show the pattern without handing over a statement. For debt, tax or investing, use chapter 11.
044. Decide: two doors
PromptI’m choosing between [option A] and [option B], and I need to decide by [date]. Don’t pick for me yet. Ask me up to five questions, one at a time, about what I’d regret either way. Then give me a table: what each option costs, what it protects, and what I’d have to believe to choose it. End with the one question I haven’t asked that could change the answer.
Parts. R: 1. A: 2, 3. D: 4. M: 5.
Habit. Ask for a way to decide, not a decision.
055. Know yourself: a week in my life
PromptI want an honest read on where my energy goes. Ask me up to seven questions, one at a time, about a normal week: what I look forward to, what I put off and what I complain about. Then name one pattern, quote the answers it comes from, and suggest one small experiment for this week. Don’t flatter me. Label anything that’s a guess.
Parts. D: 1, 3. A: 2. M: 4, 5.
Habit. Ask for evidence in your own words, so you can trace the pattern.
066. People: before the hard conversation
PromptI need to talk to [person] about [the issue], and I’m dreading it. What I want to come out of it is [outcome]. Give me an opening sentence that names the problem without blame, the two reactions to expect, and a calm reply to each. Then tell me how this might look from their side, what I may be getting wrong, and where you’re guessing.
Parts. R: 1, 2. D: 3. M: 4.
Habit. Prepare your first sentence and their point of view. The rest has to be a real conversation.
077. Mind and body: the last 45 minutes
PromptI want a wind-down routine for the last 45 minutes before bed. I go to bed around [time], I’m on my phone right up until then, and I share a small apartment. Ask me up to three questions first, one at a time, if the answers would change the routine. Then give me five short steps I could start tonight. This is about habits, not medical advice, so tell me what to raise with a doctor if it doesn’t help.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. The last line keeps a habit prompt from posing as medicine.
088. Learn: teach me, then test me
PromptI want to understand [topic]. What I already know is [my starting point]. Ask me three quick questions, one at a time, to find my level. Then explain it in five short steps, each with an everyday example, and after each step ask me one question and wait for my answer. At the end, tell me the two things I’m still shaky on.
Parts. D: 1, 4. R: 2. A: 3. M: 5.
Habit. Make it check that you followed, not only that it explained.
099. Write and create: a toast that sounds like me
PromptI’m giving a toast at [the occasion] for [person]. Three true things about them: [three details]. Here’s how I sound when I’m relaxed: [paste a message or two you’ve sent]. Write a 90-second toast in that voice, with one laugh and one sincere line. Not like this: “Webster’s dictionary defines love as.” Give me two versions, and mark the line you’d cut first if I run long.
Parts. R: 1, 2. E: 3, 5. D: 4, 6.
Habit. Show your voice, and show the tired line you’re avoiding.
1010. Everyday life: what this letter wants from me
PromptHere is a letter I received, with names and account numbers removed: [paste the letter]. Using only this text, tell me in plain language what it says, what I’m being asked to do, and by when. Then draft a short reply that asks for [what I want to happen]. If anything is unclear or missing, say so instead of guessing, and tell me who to call to confirm.
Parts. R: 1. D: 2, 3. M: 4.
Habit. Paste the real thing and keep the assistant inside it.
1111. AI basics: what should I have asked?
PromptBefore we finish, look back over this whole conversation. What’s the most useful question I didn’t ask? Which thing I told you would you double-check if you were me? What should I do first when I close this chat? Keep your answer to five lines.
Parts. R: 1, the conversation itself. M: 2, 3. D: 4, 5.
Habit. End any chat that matters with this one.
1212. Play: a bowl of questions
PromptI’m having [number] people over for dinner on [day], and a few of them have never met. Give me ten questions to put in a bowl on the table. Keep them light: nothing about work, and each one answerable in under a minute. Mix funny with thoughtful. Here’s one I like: “What’s a small thing you’re oddly good at?” Mark the three you’d open with.
Parts. R: 1. D: 2, 3, 4, 6. E: 5.
Habit. One example sets the tone better than three adjectives.
WorksheetWorksheet: Rewrite clinic
Six prompts that will get you a horoscope. Rewrite each one. The hint names the missing part.
- “Help me eat healthier.” Hint: Reality.
- “Act as a top career coach and tell me what job I should do.” Hint: drop the costume, add Ask.
- “Write a message to my friend who’s upset with me.” Hint: Reality, plus an Example of how you two talk.
- “Is this a good deal?” Hint: paste the offer, then add Measure.
- “Plan my trip to Japan: flights, hotels, food, budget and packing.” Hint: Destination. One finished thing.
- “I’m right to be annoyed with my sister, aren’t I?” Hint: Measure. Ask for her side.
One way to fix the first:
PromptI want to eat better on weeknights. I cook for myself and a teenager who lives on pasta, I have 25 minutes, and I won’t give up cheese. Give me five dinners one small step up from what we eat now. Tell me what you assumed about my budget.
Practice
Practice and library
A seven-day practice plan, a prompt library page, a glossary and the sources.
Tomorrow you will type something into an assistant anyway: a question about lunch, a reply to an email, a plan for the week. Before you send it, add one sentence that says what you want to end up with. That is day one.
Reading about better questions does little. Asking them does a lot. Ethan Mollick’s advice to beginners is to skip the formulas and put in about ten hours of real use.
WorksheetWorksheet: Seven days of practice
- Day 1, Destination. Take a prompt you’d normally type. Add what you want to end up with and its shape. Compare the answers.
- Day 2, Reality. Build your about-me card (chapter 5) and paste it above a question.
- Day 3, Example. Run the style-capture exercise (chapter 6).
- Day 4, Ask. Run one real, personal question as an interview (chapter 7).
- Day 5, Measure. Add two check lines (chapter 8) to a decision you’re weighing.
- Day 6, Wake. Run the WAKE checklist (chapter 10) on one answer from this week.
- Day 7, Your call. Try your best prompt in a second app. Then fill in the keep, share, hand over list (chapter 15).
- What I noticed this week:
WorksheetWorksheet: My prompt library page
Copy this page for each prompt worth keeping. Three good ones beat a folder of 300.
- Title:
- When I use it:
- The prompt:
- Parts it uses (circle):DREAM
- Needs (circle):nothinga fileweb searchdeeper thinkingmemory
- Worked on (app and date):
- Follow-ups that helped:
Glossary
| Term | Plain meaning |
|---|---|
| Assistant | An AI chat app such as ChatGPT, Claude, Gemini, Copilot, Perplexity or Grok |
| Context | Everything the assistant has to go on: your words, your files, its memory of you |
| Fresh chat | A conversation in which the assistant knows nothing about you |
| Memory | A feature that carries facts about you from one chat to the next |
| Temporary chat | A chat that isn’t saved to memory. Some apps call it incognito |
| Thinking mode | A slower setting that reasons for longer before it answers |
| Made-up fact | A confident statement with nothing behind it. Often called a hallucination |
| Flattery | The pull toward agreeing with you. Researchers call it sycophancy |
Sources
The factual claims in this guide come from these pages and papers, read in October 2026. Vendor pages change, so check the date.
From the companies:
- OpenAI, ChatGPT Learn, Prompting. https://learn.chatgpt.com/docs/prompting
- OpenAI, ChatGPT Learn, Personalize ChatGPT. https://learn.chatgpt.com/docs/personalize
- OpenAI Cookbook, ChatGPT Enterprise: Practical prompt engineering for everyday work. https://developers.openai.com/cookbook/examples/chatgpt/chatgpt_prompt_guide/chatgpt_prompt_guide
- OpenAI, Using GPT-5.5 (developer guide). https://developers.openai.com/api/docs/guides/prompt-guidance?model=gpt-5.5
- OpenAI, Using GPT-6 (developer guide). https://developers.openai.com/api/docs/guides/prompt-guidance
- OpenAI, Reasoning best practices. https://developers.openai.com/api/docs/guides/reasoning-best-practices
- OpenAI Academy, Prompting. https://academy.openai.com/public/clubs/work-users-ynjqu/resources/prompting
- OpenAI Help, Memory in ChatGPT. https://help.openai.com/en/articles/8590148-memory-in-chatgpt
- OpenAI Help, Health in ChatGPT. https://help.openai.com/en/articles/20001036-health-in-chatgpt
- Anthropic, Prompting best practices. https://platform.claude.com/docs/en/build-with-claude/prompt-engineering/claude-prompting-best-practices
- Anthropic blog, Best practices for prompt engineering for 2026. https://claude.com/blog/best-practices-for-prompt-engineering
- Claude Help, Use Claude’s chat search and memory to build on previous context. https://support.claude.com/en/articles/11817273-using-claude-s-chat-search-and-memory-to-build-on-previous-context
- Google, Google Workspace with Gemini Prompt Guide. https://workspace.google.com/learning/content/gemini-prompt-guide
- Google, Gemini API, Prompt design strategies. https://ai.google.dev/gemini-api/docs/prompting-strategies
- Google blog, Gemini adds Temporary Chats and new personalization features. https://blog.google/products-and-platforms/products/gemini/temporary-chats-privacy-controls/
- Microsoft, Get started writing prompts in Microsoft Copilot. https://support.microsoft.com/en-us/topic/learn-about-copilot-prompts-f6c3b467-f07c-4db1-ae54-ffac96184dd5
From independent teachers:
- Ethan Mollick, Getting started with AI: Good enough prompting. https://www.oneusefulthing.org/p/getting-started-with-ai-good-enough
- Ethan Mollick, Choosing to Stay Human. https://www.oneusefulthing.org/p/choosing-to-stay-human
- Ethan Mollick, An opinionated guide to which AI to use to do stuff (July 2026). https://www.oneusefulthing.org/p/an-opinionated-guide-to-which-ai-b22
- Lenny’s Newsletter, AI prompt engineering in 2025, with Sander Schulhoff. https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff
From research (the four Prompting Science Reports are from Wharton):
- Prompting Science Report 1 (politeness). https://arxiv.org/abs/2503.04818
- Prompting Science Report 2 (step-by-step prompting). https://arxiv.org/abs/2506.07142
- Prompting Science Report 3 (tips and threats). https://arxiv.org/abs/2508.00614
- Prompting Science Report 4 (expert personas). https://arxiv.org/abs/2512.05858
- Cheng and colleagues, Sycophantic AI decreases prosocial intentions and promotes dependence, Science, 2026. https://doi.org/10.1126/science.aec8352
- Cheng and colleagues, free preprint of the same study. https://arxiv.org/abs/2510.01395
- Jahani and colleagues, Prompt Adaptation as a Dynamic Complement in Generative AI Systems. https://arxiv.org/abs/2407.14333
- BBC Media Centre, Largest study of its kind shows AI assistants misrepresent news content 45% of the time (October 2025). https://www.bbc.co.uk/mediacentre/2025/new-ebu-research-ai-assistants-news-content
Tomorrow you will type something into an assistant anyway: a question about lunch, a reply to an email, a plan for the week. Before you send it, add one sentence that says what you want to end up with. That is day one.
Reading about better questions does little. Asking them does a lot. Ethan Mollick’s advice to beginners is to skip the formulas and put in about ten hours of real use.
WorksheetWorksheet: Seven days of practice
- Day 1, Destination. Take a prompt you’d normally type. Add what you want to end up with and its shape. Compare the answers.
- Day 2, Reality. Build your about-me card (chapter 5) and paste it above a question.
- Day 3, Example. Run the style-capture exercise (chapter 6).
- Day 4, Ask. Run one real, personal question as an interview (chapter 7).
- Day 5, Measure. Add two check lines (chapter 8) to a decision you’re weighing.
- Day 6, Wake. Run the WAKE checklist (chapter 10) on one answer from this week.
- Day 7, Your call. Try your best prompt in a second app. Then fill in the keep, share, hand over list (chapter 15).
- What I noticed this week:
WorksheetWorksheet: My prompt library page
Copy this page for each prompt worth keeping. Three good ones beat a folder of 300.
- Title:
- When I use it:
- The prompt:
- Parts it uses (circle):DREAM
- Needs (circle):nothinga fileweb searchdeeper thinkingmemory
- Worked on (app and date):
- Follow-ups that helped:
Glossary
| Term | Plain meaning |
|---|---|
| Assistant | An AI chat app such as ChatGPT, Claude, Gemini, Copilot, Perplexity or Grok |
| Context | Everything the assistant has to go on: your words, your files, its memory of you |
| Fresh chat | A conversation in which the assistant knows nothing about you |
| Memory | A feature that carries facts about you from one chat to the next |
| Temporary chat | A chat that isn’t saved to memory. Some apps call it incognito |
| Thinking mode | A slower setting that reasons for longer before it answers |
| Made-up fact | A confident statement with nothing behind it. Often called a hallucination |
| Flattery | The pull toward agreeing with you. Researchers call it sycophancy |
Sources
The factual claims in this guide come from these pages and papers, read in October 2026. Vendor pages change, so check the date.
From the companies:
- OpenAI, ChatGPT Learn, Prompting. https://learn.chatgpt.com/docs/prompting
- OpenAI, ChatGPT Learn, Personalize ChatGPT. https://learn.chatgpt.com/docs/personalize
- OpenAI Cookbook, ChatGPT Enterprise: Practical prompt engineering for everyday work. https://developers.openai.com/cookbook/examples/chatgpt/chatgpt_prompt_guide/chatgpt_prompt_guide
- OpenAI, Using GPT-5.5 (developer guide). https://developers.openai.com/api/docs/guides/prompt-guidance?model=gpt-5.5
- OpenAI, Using GPT-6 (developer guide). https://developers.openai.com/api/docs/guides/prompt-guidance
- OpenAI, Reasoning best practices. https://developers.openai.com/api/docs/guides/reasoning-best-practices
- OpenAI Academy, Prompting. https://academy.openai.com/public/clubs/work-users-ynjqu/resources/prompting
- OpenAI Help, Memory in ChatGPT. https://help.openai.com/en/articles/8590148-memory-in-chatgpt
- OpenAI Help, Health in ChatGPT. https://help.openai.com/en/articles/20001036-health-in-chatgpt
- Anthropic, Prompting best practices. https://platform.claude.com/docs/en/build-with-claude/prompt-engineering/claude-prompting-best-practices
- Anthropic blog, Best practices for prompt engineering for 2026. https://claude.com/blog/best-practices-for-prompt-engineering
- Claude Help, Use Claude’s chat search and memory to build on previous context. https://support.claude.com/en/articles/11817273-using-claude-s-chat-search-and-memory-to-build-on-previous-context
- Google, Google Workspace with Gemini Prompt Guide. https://workspace.google.com/learning/content/gemini-prompt-guide
- Google, Gemini API, Prompt design strategies. https://ai.google.dev/gemini-api/docs/prompting-strategies
- Google blog, Gemini adds Temporary Chats and new personalization features. https://blog.google/products-and-platforms/products/gemini/temporary-chats-privacy-controls/
- Microsoft, Get started writing prompts in Microsoft Copilot. https://support.microsoft.com/en-us/topic/learn-about-copilot-prompts-f6c3b467-f07c-4db1-ae54-ffac96184dd5
From independent teachers:
- Ethan Mollick, Getting started with AI: Good enough prompting. https://www.oneusefulthing.org/p/getting-started-with-ai-good-enough
- Ethan Mollick, Choosing to Stay Human. https://www.oneusefulthing.org/p/choosing-to-stay-human
- Ethan Mollick, An opinionated guide to which AI to use to do stuff (July 2026). https://www.oneusefulthing.org/p/an-opinionated-guide-to-which-ai-b22
- Lenny’s Newsletter, AI prompt engineering in 2025, with Sander Schulhoff. https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff
From research (the four Prompting Science Reports are from Wharton):
- Prompting Science Report 1 (politeness). https://arxiv.org/abs/2503.04818
- Prompting Science Report 2 (step-by-step prompting). https://arxiv.org/abs/2506.07142
- Prompting Science Report 3 (tips and threats). https://arxiv.org/abs/2508.00614
- Prompting Science Report 4 (expert personas). https://arxiv.org/abs/2512.05858
- Cheng and colleagues, Sycophantic AI decreases prosocial intentions and promotes dependence, Science, 2026. https://doi.org/10.1126/science.aec8352
- Cheng and colleagues, free preprint of the same study. https://arxiv.org/abs/2510.01395
- Jahani and colleagues, Prompt Adaptation as a Dynamic Complement in Generative AI Systems. https://arxiv.org/abs/2407.14333
- BBC Media Centre, Largest study of its kind shows AI assistants misrepresent news content 45% of the time (October 2025). https://www.bbc.co.uk/mediacentre/2025/new-ebu-research-ai-assistants-news-content
Who it is for.
Anyone who uses an AI assistant a few times a week and suspects there is more to get out of it.
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You are not a developer.
There is no code in it and no jargon. If you can write an email, you can do everything in the book.
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You ask about your own life.
Dinner, money, a hard conversation, a doctor’s appointment, a decision you keep putting off. The examples are those, not marketing copy.
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You want to keep your judgment.
Half the book is about the answer: where it came from, what it assumed about you, and what to check before you act on it.
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You are done with magic words.
Chapter 2 goes through the famous tricks and what the tests say about each one. Most of them can go.
Take it with you.
Free to read, print and pass on. It is published under CC BY 4.0, so you can share it with a class, a team or your family.