How to Ask ChatGPT Questions
Twenty questions to type into ChatGPT, with a note on each about why the wording changes the answer and what a poor response to it looks like. They cover getting it to ask you for missing information, requesting reasoning before conclusions, asking for options rather than a recommendation, testing your own premise, and checking which parts of an answer need verifying. For anyone whose results feel vague or generic.
The questions
Open any question for the note
Before you answer, what do you need to know from me?
Why ask it
Fixes the most common cause of a generic answer, which is a question with no context in it. Expect three or four clarifying questions back. If the reply skips straight to an answer anyway, say so directly and ask again, because answering the questions it raises is usually faster than rewriting your original prompt.
Here is what I am trying to do, who it is for, and what I cannot change. What do you suggest?
Why ask it
The three pieces most people leave out are the goal behind the task, the audience, and the constraints. Supplying them turns a request for content into a request for a solution, and it is the difference between a passable answer and a usable one.
Can you show your working step by step before you give me the answer?
Why ask it
Useful on anything with several stages, because it lets you see where a wrong answer went wrong rather than just that it did. Read the steps rather than skimming to the conclusion: a confident final figure on top of an error in step two is a common failure.
What are the three things I have most likely not thought of?
Why ask it
Asking for a fixed number produces sharper items than asking what you are missing. Discard the obvious ones without argument, which is usually one of the three, and treat this as a checklist prompt rather than as an assessment of your plan.
What is the strongest argument against what I have just said?
Why ask it
Worth asking because the default behavior is to agree with you and build on your framing. Ask for the strongest version specifically, otherwise you get a token objection that is easy to knock down and tells you nothing.
Which parts of that answer are you least sure about?
Why ask it
Flags where to look rather than giving you a reliable measure, since stated confidence is not calibrated and sounds the same whether the underlying claim is solid or invented. Use it to pick what to verify, not as permission to trust the rest.
Which of those claims can be checked, and where would I check them?
Why ask it
The important follow-up to any answer containing facts, figures or quotations. References can be produced that look correct and do not exist, so ask for the source and then go and open it. If a claim cannot be traced to anything, treat it as unsupported.
Give me three options with the tradeoff for each, and do not tell me which to pick.
Why ask it
Blocks the single confident recommendation that reads well and hides the reasoning. The instruction not to choose matters: without it you usually get three options and a nudge toward the middle one, which is rarely the best fit for your situation.
What would have to be true for this to be a bad idea?
Why ask it
Turns a general request for risks into a specific set of conditions you can go and check. The answers tend to be assumptions you had made without noticing, about timing, other people's cooperation, or money.
Where might my premise be wrong?
Why ask it
Most bad answers are correct answers to the wrong question, and this is the prompt that catches it. Expect some pushback on the framing of your own request, which is the point, and be prepared to restate the problem rather than the task.
Can you explain that as if I know nothing about it, and then again for someone who works in the field?
Why ask it
The two versions together are more informative than either alone, because the gap between them shows you which parts are genuinely technical and which were just jargon. Ask for the plain version first so it is not written as a summary of the expert one.
Here is my draft. What is the weakest paragraph, and why?
Why ask it
Asking for the weakest one gets a specific verdict instead of a friendly list of small suggestions. Ask why before you ask for a rewrite, since the reason is often something you can fix better yourself than it can.
Can you match the way I write? Here are two things I have written.
Why ask it
Examples do far more than adjectives about tone. Two samples of your own writing beat any instruction to be professional or conversational, and it is worth naming a habit to avoid as well, such as opening every paragraph with a rhetorical question.
What questions will my manager ask when they read this?
Why ask it
Rehearses the actual review you are about to face and produces a to-do list, not commentary. Say who the reader is and what they care about, because the same document draws entirely different questions from a finance reviewer and a customer.
What is the simplest version of this that would still work?
Why ask it
A useful counterweight, because the default output tends toward thoroughness: five phases where two would do. Ask for the minimum and then decide what to add back, rather than trying to cut an elaborate plan down.
Can you take the other side and push back on me while I argue this out?
Why ask it
Effective for preparing a difficult conversation, and it works best if you specify who the other person is and what they actually want. Tell it not to fold: it will otherwise concede after one round of resistance, which is no rehearsal at all.
What did I ask for that you could not do, and what did you do instead?
Why ask it
Catches quiet substitutions: a shorter list than you asked for, a constraint dropped, a section invented. Long instructions are where this happens most, and the earliest parts of your request are the ones most likely to have gone missing.
Can you cut that to five points I could say out loud in a meeting?
Why ask it
Naming the setting does most of the work, because points meant to be spoken come out shorter and less nested than points meant to be read. Read them aloud once: anything you stumble over is a sentence to fix before the meeting, not after.
If you had to guess what I actually want rather than what I asked for, what would you say?
Why ask it
Often produces the most useful reply in a long session, because it surfaces the goal you have been circling. It also exposes a wrong assumption that has been shaping every answer so far, at which point starting a fresh chat is usually quicker than correcting it.
What should I ask you next?
Why ask it
A reasonable closer when you are new to a subject and do not yet know the shape of it. Treat the suggestions as a map of the territory rather than as advice, and expect one or two to be filler you can ignore.
Getting better answers
Practical guidance for the conversation itself
What to put in the prompt
The four things worth stating every time
- The task, in one sentence, with the outcome you want rather than the format you imagine.
- The audience: who reads it, what they already know, what they will object to.
- The constraints: length, budget, tools you have, things you cannot change.
- The form of the answer: a list, a table, an email, three options, five hundred words.
Show rather than describe
One example of what good looks like is worth several paragraphs of instruction. Paste a piece of work you liked, or one you disliked with a note about why, and ask for something in that direction.
Say what to leave out
Negative instructions work: no preamble, no summary at the end, no bullet points, no adjectives you would not use in speech. This is the fastest way to remove the house style that makes output recognizable.
One question per message
Three questions in one message reliably gets two answered well and one skimmed. Ask them in sequence and you can also correct course after the first answer.
When the answer is not right
- Say what is wrong with it rather than asking again. "Too general, give me the version for a team of four with no budget" gets further than repeating the original request.
- Correct one thing at a time. Long correction lists get partially applied and you lose track of which parts were followed.
- If the answer keeps returning to a wrong assumption, start a new chat with a cleaner statement of the problem. Arguing inside a long thread is slower than restating it.
- Ask it to rewrite its own answer against a checklist you supply. Self-review catches some errors, though it will not catch a fact it is confident about.
- Be careful with agreement. Push back on a correct answer and it will often abandon it, so pushing back is not a good test of whether something is true.
What to check before you use it
- Any citation, quotation, case name, statistic or study. Plausible references that do not exist are a well-documented failure, so open the source before you repeat it.
- Numbers and arithmetic in anything that matters, including totals in a table it generated.
- Names, dates and job titles of real people, and anything about a specific company's current situation.
- Anything legal, medical, tax or safety related. Use the output to work out what to ask a professional, not as the answer.
- Code, before it goes anywhere near production. Read it, run it, and check what it does with bad input.
Habits worth dropping
Politeness padding
Please and thank you cost nothing but do not improve the answer. The words that change the output are the ones carrying information: audience, constraint, example, format.
Asking it to be creative and nothing else
Vague adjectives such as creative, engaging or professional produce the average of everything. Name a constraint instead, since a specific limit on length, form or vocabulary generates more interesting output than an instruction to be interesting.
Pasting things you should not paste
Customer records, credentials, unreleased financials, someone else's private messages. Check what your organization allows before you paste anything you would not put in an email to an outside supplier.
Accepting the first draft because it reads well
Fluency and accuracy are separate. The most confident, best-organized answers are also the easiest to accept without checking, which is where most real mistakes come from.