Make AI second nature.

I'm meeting with someone who's going to set up a personal AI system around my work, my files, and how I run my business. Write a complete briefing they can read before we meet.

How to work:
- Pull from everything you can reach on me: memory, past chats (search them if you can), projects, custom instructions, uploaded files, and connected tools. Use real examples from our conversations.
- Tag every claim: [Known] if I told you or you saw it, [Inferred] if you're reading between the lines, [Unknown] if you can't tell. Never guess to fill a gap. Turn the gap into a question for me.
- Be honest, not flattering. If I'm doing something the slow way, say so.
- Leave out passwords, account or card numbers, health details, and anything private about other people. Describe people by role (my assistant, my business partner), not by name.

First, a quick check. Tell me which sources you could actually see (memory, past chats, files, connected tools) and roughly how much you know about me. If it's thin, say so plainly. Then skip the sections you can't fill honestly and interview me instead: ask me the most useful questions one at a time, at most ten, and write the briefing from my answers.

Start the briefing with a five-line summary: who I am, what I want, where I am with AI, the biggest time sink, and the one thing to fix first.

Then cover:

1. Who I am and what I do. My role, my businesses or clients, how I make money, and what a normal week actually looks like.

2. My priorities right now. What I'm trying to grow or fix, and what a good next three months would look like.

3. The people around my work. Who helps me (assistant, team, partners, outside help), what they handle, and who would keep an AI system running day to day besides me. Roles only.

4. My tools. Which AI I use (Claude, ChatGPT, Gemini, others) and which plan. Any projects, custom instructions, memory, connectors, skills, agents, or automations I've set up. Then the rest of my stack: email, calendar, documents and file storage, notes, CRM or client tracking, messaging, and my computer (Mac or PC).

5. Where I am with AI. Place me on this ladder at the highest rung I clearly do today, not something I tried once. Give two or three real examples as evidence, with how confident you are in each.
   0. Not yet: I rarely use AI on purpose
   1. Curious: I ask it questions, like a smarter search box
   2. Conversational: I use it to think things through and push back on weak answers
   3. Informed: I give it my own material first (past emails, notes, files) so the work sounds like me
   4. Making: I use it to make finished things I actually send or share
   5. Delegating: it takes real actions in my tools, with me approving
   6. Systemized: at least one AI workflow runs on its own schedule
   7. Second nature: my AI tools share memory of my work, and I mostly review

6. How I actually use AI. The tasks I bring to it most, what works well, where it keeps falling short, and what I've given up on.

7. What I keep asking for. Requests, tasks, or questions I come back to again and again. Quote my own words where you can. These are the best candidates to automate.

8. Recurring workflows. Anything I do weekly or repeatedly. For each: what starts it, the steps, which tools it touches, roughly how often, and which parts are manual.

9. Where my files live and how they're organized. My computer, Google Drive, Dropbox, Notion, email, wherever. Naming habits, and what's a mess.

10. Pain points. Where I lose time, repeat myself, re-explain context, or let things drop.

11. Goals. What I've said I want, things I've tried and abandoned, and ideas I keep circling back to.

12. Boundaries. What I'd never want AI to do without asking me first, and anything I'm uneasy about it touching (certain accounts, people, money, or topics).

13. Blind spots. What am I not asking AI to help with that I probably should be?

14. Your candid assessment. The five tasks or workflows that would save me the most time if they ran on their own or with one click from me. For each: what would start it, what it would do, what should wait for my yes, and a rough guess at hours saved per week (marked as a guess). Then the three changes that would make the biggest difference, and the one thing you'd fix first.

End with two lists:
- Open questions for me, the ones only I can answer.
- Things to check before I send this: anything in the briefing that might be too personal or sensitive to share.

Plain language, no filler, under about 2,000 words. Use the numbered headings above so it's easy to scan. If you run out of room, stop at the end of a section and tell me to say "continue". Format it so I can copy the whole thing and send it to the person I'm meeting.