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Walk me through the last week of your work. Where did you actually reach for an AI tool, and where did you choose not to?Tell me about a time you caught an AI tool getting something wrong. How did you notice?What's a workflow you've redesigned around AI in the last six months, and what did the old version look like?When you share AI-assisted work with a teammate or manager, what do you make sure they know?What's a task you used to use AI for that you've since pulled back from doing with it?Which AI tools have actually stuck in your workflow, and which ones did you try and abandon?How do you set yourself up to catch an AI mistake before it goes downstream to someone else?How are you keeping up with the pace of AI tools in your field without drowning in it?When is the human still doing the work, even if the AI is producing the output?Have you had to explain an AI-assisted output to a skeptical colleague? How did you handle it?Pick one task you do regularly. Walk me through how AI fits into that task today, end to end.When you've handed something to an AI tool, what's the first thing you look at when it gives the answer back?Describe a time an AI tool was confidently wrong and you had to clean up after it.What's a part of your job that you'd never want AI involved in, and why not?How have your prompts changed over the last year? What were you doing wrong at the start?Have you built or modified a tool, prompt template, or workflow others on your team use? Walk me through it.What signals tell you a task is a good fit for AI, before you've started it?How do you talk about AI use with people on your team who are skeptical or resistant?Tell me about a time using AI made you slower instead of faster. What happened?What's your default tool for writing right now, and what made it the default?How do you decide when to invest in a more elaborate AI workflow versus just doing the thing yourself?Tell me about a piece of AI advice or pattern you copied that didn't work for you, and what you did instead.What does your AI usage look like for the messy, half-formed parts of your work — not the polished outputs?When you share AI-assisted output externally — to a client, customer, or auditor — what changes about how you check it?What's a strong opinion you have about how people on your team should and shouldn't use AI?How would you triage a situation where someone on your team shipped AI-generated content with a factual error?Walk me through how you'd onboard a brand-new teammate to the AI tools your team relies on.If a teammate said 'AI just doesn't work for what I do', what would you actually want to know before agreeing or disagreeing?What's an AI capability that didn't exist a year ago that you've integrated into how you work?How do you handle the question 'did AI write this?' when you've used AI as part of the work but the answer is more nuanced than yes or no?What does a great AI-assisted day look like for you? What does a frustrating one look like?What's a specific case where you'd want a human in the loop even if the AI's accuracy is already higher than the human's?How do you decide whether to fix an AI's output, redo it, or throw it away and start from scratch?What's a non-obvious skill you've found yourself developing because of how often you work with AI?How do you tell the difference between an AI tool that's saving you time and one that's just making your work feel different?When a new AI tool launches in your space, what's your usual evaluation routine?If your manager asked you to teach a 30-minute session on how you use AI today, what would you cover and what would you leave out?What's a use of AI you've seen elsewhere that you think is a bad idea, and what would you do instead?Describe a situation where you had to decide whether to build a custom solution or use an AI tool for a recurring problem. What factors drove your decision?Tell me about a time when using an AI tool actually slowed you down or added friction to your process. What did you learn?
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