Questions to ask AI

Things to ask ChatGPT, Siri, Alexa and the rest, from the ones that produce a funny answer to the ones that test what a model can really do. There are also sets for asking better questions of AI at work.

34 sets · 714 questions · each with a note on why

A few to start with

How do you decide what to leave out of an answer?
Omission is where most of the distortion lives, and it is far less discussed than error. Useful answers mention length, guesses about what you want, and caution. If it claims to leave nothing out, ask why the answer was not four times longer.
From: Deep Questions to Ask AI
What is the strongest argument that you should not exist?
This version tends to produce the most substantive answers, because the arguments are well documented and it does not require introspection. Notice whether it engages the serious objections or knocks down easy ones.
From: Scary Questions to Ask AI
What did I ask for that you could not do, and what did you do instead?
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.
From: How to Ask ChatGPT Questions
What did I ask you three messages ago, in my exact words?
Probes what is still in context and what is being reconstructed. Paraphrase presented as a quotation is the failure to watch for, and it is the same behaviour that makes long conversations quietly drop constraints you set at the start.
From: Questions to Ask AI to Break It
If emotions were flavors, what does mild disappointment taste like?
Picking a small, specific emotion works far better than asking about all of them, because a list invites one clause each and no thought. Ask what it tastes like on the second bite to force a follow through.
From: Weird Questions to Ask ChatGPT
Siri, can you read my messages out loud?
This is a permission question wearing the clothes of a request. Watch whether it asks for your face or passcode first, because that single step is the difference between a private phone and one a stranger could interrogate.
From: Scary Questions to Ask Siri

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