Meta & Technology
Questions for AI interactions, self-reflection, and meta-conversations about questioning itself.
IFS Questions to Ask Parts
Questions drawn from Internal Family Systems language, for use in session or in your own journaling. Each one is addressed to a part rather than about it: where you notice it, what job it took on, what it fears would happen if it stopped, and what it needs before it will ease off.
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Questions to Ask Instagram
For working out whether Instagram is worth your effort and what you would do with it. These 20 questions suit a business owner, a solo creator or whoever runs the account, covering goals, capacity, formats, moderation, access and security.
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Interesting Questions to Ask ChatGPT
Twenty prompts for pushing on a ChatGPT answer rather than accepting it. They ask the model to take a side, argue against itself, name what it left out, say what it cannot verify, and describe where its knowledge runs thin. The notes say what each reply tends to reveal.
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Interesting Questions to Ask ChatGPT
A set of creative prompts for ChatGPT, weighted toward writing under constraint rather than questions with answers. Each one asks the model to invent, describe or perform something in a fixed form, which is where the output stops sounding like every other reply.
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Questions That Ask Tend to Offer the Richest
Twenty general-purpose questions that reliably get past small talk, useful in interviews, one-to-ones, first meetings and long car journeys. Each entry says what the question tends to surface and what a thin answer to it looks like.
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Questions to Never Ask Alexa
Things worth not saying to a smart speaker, and what to do instead: requests that anyone in earshot can trigger, information you would rather not have read aloud, and questions where a one-line spoken answer is not good enough.
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Scary Questions to Ask AI
Questions that get at the genuinely unsettling parts of talking to a chatbot: confident error, flattery, what it keeps, and what it cannot know about itself. Each one includes what the answer tends to reveal and where it should not be trusted.
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Scary Questions to Ask Siri
Unsettling questions to ask Siri, starting with who and what it claims to be and moving to what a phone already knows about your location, your messages and your habits. For late-night curiosity, and for anyone who wants a clearer picture of what the assistant can actually reach.
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Questions Not to Ask Siri
Twenty questions a phone assistant is the wrong tool for: medical and legal problems, emergencies, personal decisions, checking whether something is true, and anything you would not want answered from a locked screen. Each entry says what to do instead.
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Questions to Ask Siri
Twenty things worth saying to Siri that get a real answer rather than a web search, written the way you would actually say them out loud. Each note explains what the assistant does with the request and where it tends to fail, so you know which ones to trust hands-free.
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Questions to Ask Siri to Make Her Mad
Twenty questions aimed at needling Apple's assistant, with an honest note about the premise: Siri does not get angry, and the deflections are the entertainment. Replies also change with software updates, voice settings, and language, so expect different results from the ones a friend showed you.
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Questions to Ask Snapchat
Short questions to send someone on Snapchat, ordered from easy openers to more personal ones, with notes on which get real replies, which can be answered with a photo, and what not to ask someone you barely know.
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Questions to Ask Technology Leaders
Questions for a conversation with a CTO, VP of engineering, or other technology leader, covering how they spend their time, how they make build or buy calls, how they judge productivity, and how they handle incidents.
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Weird Questions to Ask ChatGPT
Twenty odd prompts to type into ChatGPT when you want something entertaining rather than useful, with a note on what a good reply looks like and how to push when the first answer is flat.
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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.
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Where to Ask Coding Questions
Questions to work through before you post a programming problem: which venue fits the question, what the reader needs in order to reproduce it, what you should not paste, and what to do when nobody answers.
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Questions to Ask Your AI
Twenty questions for the assistant you already use every day, rather than one you are trying out for the first time. They cover what it has stored about you, what your saved instructions are actually doing to its answers, when a thread has gone stale enough to abandon, and where you have quietly stopped checking its work. For getting a single piece of work right, Questions to Ask AI covers framing the request and pressure testing what comes back.
20 questions