What Questions to Ask ChatGPT
Questions and instructions that change what you get back from ChatGPT, from asking it to interrogate you before answering to asking where it is likely to be wrong. Written for people who already use it and get bland results.
The questions
Open any question for the note
What do you need from me to answer this well?
Why ask it
Most weak answers come from a prompt with no context about audience, length, constraints, or purpose. Asking this first surfaces the three or four missing details that would otherwise produce a generic answer you then spend ten minutes correcting.
Ask me any questions that would change your answer before you give it.
Why ask it
Left alone, the model fills gaps with plausible assumptions and never mentions doing so. Forcing the questions to the surface exposes those assumptions while they are still cheap to correct, and often reveals that your own request was ambiguous.
Explain this as if I know nothing, then again as if I work in the field.
Why ask it
Two passes at different levels show you which parts of an explanation are genuinely simple and which were simplified into something misleading. The gap between the versions is usually where the real difficulty in the subject sits.
Give me the strongest argument against what you just said.
Why ask it
Models tend to agree with the framing they are handed, so a follow-up that demands opposition is more useful than asking whether the answer is right. If the counterargument is limp, that is a sign the original answer was a consensus summary rather than analysis.
How confident are you in that, and which parts are you least sure about?
Why ask it
Fluent prose reads as confident whether or not the content is reliable, and that mismatch is where people get burned. The stated confidence is not a calibrated number, but the parts it flags as shaky are worth checking first.
Which of this might be out of date, and how would I check?
Why ask it
Anything involving prices, laws, software versions, or current officeholders is a likely failure point. A useful answer separates the stable parts from the volatile ones instead of hedging over the whole thing.
Rewrite this paragraph of mine without changing my voice.
Why ask it
The default editing style flattens everything toward the same measured register, so the instruction to preserve voice is doing real work. Compare the output against your original sentence by sentence rather than accepting it whole.
Here is my draft. Tell me what is wrong with it before you suggest fixes.
Why ask it
Ask for edits and you get a rewrite that hides the diagnosis inside the changes. Separating critique from revision means you learn something repeatable, and it stops the tool from quietly replacing your argument with a smoother one.
Give me ten options, including three I would probably reject.
Why ask it
Asking for a number forces range, and asking for bad ones defeats the pull toward the safest possible suggestion. The rejects are frequently the most useful part, because they mark the edges of what you actually want.
What am I not asking that I should be?
Why ask it
This works because the model has seen the shape of your problem many times and can name the standard omission. Expect some filler, but it reliably catches one or two considerations that a person new to a subject would not know to raise.
Act as a skeptical reviewer of this plan and put your hardest questions to me.
Why ask it
Assigning an adversarial role produces sharper output than asking for feedback, which tends to arrive wrapped in encouragement. Answer the questions yourself rather than asking it to answer them, or you lose the entire benefit.
Summarize this document, then list what it does not say.
Why ask it
Summaries smooth over gaps, contradictions, and conspicuous silences, which are often the important content in a contract or a report. The absence list is the half you cannot get by reading faster yourself.
Turn this into a checklist I could actually work through tomorrow.
Why ask it
Advice tends to arrive as principles, which feel useful and change nothing. Demanding concrete steps exposes the parts that were never actionable, and any item you cannot start without more information marks a genuine gap in the plan.
What would someone experienced in this notice that I would miss?
Why ask it
This reliably pulls up the practical knowledge that sits between the textbook and the job: the step everyone skips, the cost nobody mentions, the order things have to happen in. It is the highest-yield question for any unfamiliar task.
Work through your reasoning step by step, then give me the answer.
Why ask it
Answers stated first and justified afterwards are often reverse-engineered, particularly on anything involving arithmetic, dates, or multi-step logic. Reading the steps also lets you find the exact point where it went wrong instead of discarding the whole answer.
Where are you most likely to be wrong about this particular topic?
Why ask it
Narrower and more useful than asking about general limitations. Answers tend to name thin training material, contested areas, and details that vary by jurisdiction, which is a decent map of where to verify independently.
Compare these two options on the criteria that actually matter, and tell me which you would choose.
Why ask it
Without the second half you get a balanced table and no conclusion, which leaves the work with you. Requiring a pick forces the criteria to be weighted, and you can then argue with the weighting, which is the productive conversation.
Teach me this by quizzing me rather than explaining it.
Why ask it
Reading an explanation feels like learning and mostly is not. Being asked questions exposes what you cannot yet do, and it is one of the few uses of these tools that leaves knowledge with you instead of on the page.
What should I search for to verify this myself?
Why ask it
Ask for citations and you may get references that look right and do not exist. Asking for search terms and the type of source instead gives you something checkable, and it is the correct habit for anything you will rely on.
Now do it again, shorter, and cut anything you added to sound thorough.
Why ask it
Output drifts long, with restated questions, preambles, and summaries of what was just said. A second pass aimed at deletion usually removes a third of the text without losing anything, and shows you how much of the first answer was padding.
Getting better output
Practical guidance for the conversation itself
How you frame the request
Say who it is for and how long it should be
Audience and length are the two constraints that change output most. A note for a colleague who already knows the background and a briefing for someone outside the field are different documents, and without being told it will write neither.
Give an example of what good looks like
One sample of the tone or format you want does more than three paragraphs of description. This is the single most effective habit for anyone using these tools for writing.
Ask for the reasoning on anything you will act on
For numbers, dates, and multi-step problems, requesting the working lets you find the error. Answers that arrive as a confident conclusion give you nothing to check.
Working in more than one pass
- 1Ask it to interrogate you first, and answer the questions it raises.
- 2Get a rough version and read it for structure rather than wording.
- 3Attack it: ask for the strongest objection, then for what a reviewer would flag.
- 4Ask for a shorter version with the padding removed.
- 5Do the final edit yourself. The last ten percent is where your own judgment and voice have to come in.
What always needs checking
- Citations, quotations, page numbers, and case names. Plausible-looking references that do not exist are a well-documented failure mode.
- Anything with a date attached: prices, tax thresholds, software versions, who currently holds a position.
- Legal, medical, and financial specifics, which vary by jurisdiction and are usually answered from the most common context rather than yours.
- Arithmetic in the middle of prose, where a wrong figure carries through the rest of the answer unremarked.
- Summaries of documents you have not read. Check the parts the summary treats as unimportant, since that is where omissions hide.
- Anything that agrees with you completely. Agreement is the default behavior, not a verdict.
Things it is not good for
- Deciding something you should decide. It will produce a confident recommendation from whatever framing you supplied, including a bad one.
- Confidential material. Assume anything you paste may be retained or reviewed unless your account settings and your employer's policy both say otherwise.
- Telling you what is happening now, unless it is actually retrieving current sources and showing them to you.
- Counting, measuring, or precise formatting of long documents, where it will assert a total it has not calculated.
- Emotional support in place of a person. It is available and endlessly patient, which is not the same as being any help with a serious problem.