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GreyBrain Pulse · Published 14 Oct 2026

The questions to ask before it is too late

The human · What’s possible · F6

An interview plan and forty specific questions — including the ten people most regret never asking.

Why this matters for your role

A faculty discussion: which parts of learning should AI support, and which must students demonstrate independently?

Your worked example

A fictional doctor wants to restart a personal photography hobby. They have a phone camera, enjoy observing light and prefer a nearby public park. No schedule, budget or access information is provided.

Put it into practice

Suggest a small photo-walk creative brief with three observation prompts. Keep unknown opening hours, permissions and costs as questions to check. Do not claim guaranteed time savings or wellbeing benefits.

Practise with a synthetic example. Do not upload identifiable patient information. Check every factual claim and source before considering any real-world use.

Clinician prompt

The questions to ask before it is too late

An interview plan and forty specific questions — including the ten people most regret never asking.

Copy · paste into your AI

Help me record my family's history properly, before the people who remember it are gone. Who I want to record: [WHO — a parent, a grandparent, an aunt] What I already know: [A FEW LINES] Time I realistically have with them: [e.g. two afternoons] Produce: 1. An interview plan for the time available, ordered so it opens easily and reaches the harder things only once they are comfortable. 2. Forty questions grouped by period of their life — not "tell me about your childhood" but specific ones that unlock a real memory: objects, routines, smells, money, journeys, what was on the radio. 3. The ten questions people most regret never asking, and why each one matters. 4. How to record it practically, with the phone I already have. 5. What to do in the first week afterwards so the recording does not sit unlistened-to forever. 6. How to handle it if they become upset, or refuse a subject. End with a short section titled "Your check" listing what I must verify myself before using any of this.

Synthetic practice example. Run it as-is and check the output against the supplied facts.

Your check

Ask permission before recording, and let them stop whenever they want. This is their story, not your project.

Runs inChatGPT Claude Copy the prompt first — these links open the tool, they do not carry the text.

A personal exercise, nothing to do with clinical work. Treat what you are told as private unless they say otherwise.

Sources inform this fieldnote; their publishers do not endorse GreyBrain. This exercise does not confer clinical competence or a certificate.

The questions to ask before it is too late | GreyBrain Pulse | GreyBrain School of AI