ChatGPT Questions to Ask
Twenty prompts to try with ChatGPT when you are not sure how to phrase what you want, covering explaining a topic, editing a draft, checking a calculation, comparing options, debugging code and verifying what it tells you.
The questions
Open any question for the note
Explain this topic to me as if I already understand [something related that I do know].
Why ask it
Naming a reference point you already hold sets the level, so you skip the encyclopedia opening. If it still starts from the textbook definition, your reference point was too broad to be useful and needs to be one specific thing.
What am I most likely getting wrong about this?
Why ask it
This pulls the common misconceptions to the front instead of the standard summary. An answer full of hedges about the topic being complex usually means you have wandered outside what it handles reliably.
Ask me questions until you have enough to help with this properly.
Why ask it
Most weak output comes from missing context rather than a weak model. Watch whether it asks one question and then guesses anyway, which is your cue to supply the constraints yourself.
Here is my draft. Which single sentence is the weakest, and why?
Why ask it
Asking for one forces a judgment instead of a tidy list of compliments. Skip past any opening praise; the reasoning attached to the sentence it picks is the only part worth reading.
Shorten this without losing anything, then tell me what you cut.
Why ask it
The second half is the test. If it cannot list what it removed, it rewrote the passage from scratch rather than editing it, and you have lost details you may have wanted.
Read this and tell me what a reader could reasonably misunderstand.
Why ask it
It reads without your intentions in mind, which is close to how a stranger will read it. Ambiguous pronouns and unexplained shorthand show up here that you cannot see in your own writing.
Give me three genuinely different approaches to this, with the tradeoff of each.
Why ask it
Without the tradeoff clause you get a ranked list where the first option is obviously the intended answer. If the three tradeoffs read almost identically, the options are variations rather than alternatives, so ask again.
What is the standard way to do this, and why do people depart from it?
Why ask it
The second half surfaces the situations where the default advice fails, which is usually the part you actually need. It also tells you whether there is a real convention or just one popular opinion.
Argue against the position I just took, as strongly as you can.
Why ask it
The failure mode is a straw man that is easy to knock down. If the counterargument is one you had already dismissed, say so and ask for the version a well-informed opponent would use.
What would a specialist in this field want to know before answering?
Why ask it
This produces the list of facts your question was missing: jurisdiction, timeframe, scale, budget. Filling those in yourself is usually the difference between generic output and something you can act on.
Where do experts actually disagree here, rather than what the consensus is?
Why ask it
Useful when you suspect a question is contested. Be wary if it manufactures two sides for something long settled, because that is a sign it is pattern-matching rather than reporting.
Walk me through this calculation step by step and show the numbers.
Why ask it
Arithmetic mistakes hide comfortably inside confident prose. Broken into steps they become checkable, and any step you cannot verify is one to redo by hand before you rely on it.
What should I read or search for to check this myself?
Why ask it
Treat whatever comes back as search terms, not citations. Plausible titles and author names can be generated for sources that do not exist, so nothing here counts until you have found the document.
Here is my code and the error message. What is the most likely cause?
Why ask it
Asking for the most likely cause avoids a wall of twelve possibilities. If it responds by rewriting your whole file, stop and ask it to explain the error line first, or you will lose track of what changed.
I have forty minutes and this deadline. What is the best use of the time?
Why ask it
Stated constraints turn advice into a plan. Without a time limit in the prompt you get a list of everything that could theoretically be done, which is no help at nine in the evening.
Turn this into a checklist I can follow tomorrow morning.
Why ask it
Forcing the output into steps exposes gaps that flowing paragraphs conceal. Any item you cannot picture yourself doing is a step that needs breaking down further.
Quiz me on this one question at a time, and do not tell me the answer until I have tried.
Why ask it
Testing yourself sticks better than rereading. The instruction matters because the default behavior is to include the answer in the same message, which turns practice back into reading.
Play the person on the other side of this conversation so I can practice.
Why ask it
Useful before a negotiation or a difficult call. Give it the other person's incentives and constraints, or it will play someone unusually reasonable and you will practice the easy version.
Where might you be wrong about this?
Why ask it
A useful answer names a specific class of case: a jurisdiction, a version number, a date after which things changed. A generic reminder that it can make mistakes means you should verify the whole answer elsewhere.
Summarize what we have settled in this conversation so I can paste it somewhere.
Why ask it
The summary shows what it is still carrying. Anything you decided earlier that is missing from the summary has dropped out of what it is working from, and needs restating before you continue.
Getting more out of the conversation
Practical guidance for the conversation itself
What actually improves the answers
Paste the real thing
Describing your draft, your spreadsheet or your error gets you advice about a hypothetical version of it. Pasting the actual text, numbers or message gets you advice about yours. This is the single largest difference in output quality.
State the constraint you are working under
Word count, deadline, budget, audience, reading level, the tool you are stuck with. Unstated constraints get filled with generous defaults, and you end up rejecting suggestions that were never possible.
Ask for one thing at a time
A prompt that asks for a summary, a critique and a rewrite gets a shallow pass at all three. Run them as separate turns and you can correct course after each one.
Correct it rather than starting over
Saying which part was wrong and why usually recovers faster than rewriting the prompt from scratch, because the context you have already built stays in place.
What to check before you rely on it
- Citations, page numbers and quotations. Confirm the source exists and says what it is claimed to say.
- Arithmetic and unit conversions, especially anywhere inside a longer explanation where the number is not the point.
- Anything time-sensitive: prices, laws, product features, who currently holds a role.
- Specific medical, legal and tax questions. Use it to prepare questions for a professional, not to replace one.
- Claims about itself, including what it can remember, what it can access and how it was built.
When to stop asking
After the second wrong answer on the same point
Repeated failure on one specific fact usually means it does not have the information, and further attempts produce more confident versions of the same error rather than a correction.
When a long thread starts drifting
Instructions given twenty turns back stop being honored. Ask for a summary of the decisions so far, open a new conversation, and paste the summary in as your starting point.
When you are using it to avoid deciding
It will generate another round of considerations for as long as you ask. If you already have the tradeoffs written down, the missing step is a decision, not another prompt.
Before you paste something in
Treat anything you enter as leaving your machine. Check your employer's policy before pasting internal documents, customer data or code you do not own, and strip names, account numbers and addresses when the specifics are not needed for the question. If the material is confidential and the policy is unclear, describe the shape of the problem instead of pasting the document.