
Free guide · by Cooper Simson
One Prompt Builds Your Custom 30-Day AI Plan
Paste this prompt into Claude. Answer the questions honestly for an hour. Out comes a fully custom 30-day plan ranking your top 10 AI opportunities across work, personal life, creative projects, and goals.
No email required. Use it today.
Paste one prompt into Claude, answer its questions honestly for an hour, and out comes a fully custom 30-day plan ranking your top 10 AI opportunities across work, personal life, creative projects, and goals. Instead of guessing which AI tools to try, you let AI figure out where it can help you most.
What You'll Learn
- The deep interview prompt that interrogates you across 10 rounds and 100+ questions
- How to answer so the plan comes back specific instead of generic
- What your finished plan includes: top 10 opportunities, tools, time saved, and a 30-day roadmap
- What to do after the interview so the plan actually sticks
How This Works
You'll paste one prompt into Claude. It will interrogate you across 10 rounds and at least 100 questions, covering your work, personal life, relationships, passions, fears, goals, finances, health, and creative interests. This is not a quick hack. Set aside at least an hour, sit down with a voice-to-text tool, and go deep. The more honest and specific you are, the better your plan will be.
What You Need
- Claude (claude.ai, a free account works fine)
- A voice-to-text tool like SuperWhisper or WhisperFlow so you can talk instead of type
- At least one hour of uninterrupted time (some people take 2 hours)
- Willingness to answer honestly about every area of your life, not just work
The Interview Prompt
Copy and paste this entire prompt into Claude. It's long on purpose. The detail in the prompt is what makes Claude ask the right questions:
I want you to act as my personal AI implementation strategist. Your job is to conduct an extremely thorough interview to understand EVERYTHING about me: my work, personal life, goals, fears, relationships, passions, health, finances, creative interests, and daily habits. Then use that complete picture to build a hyper-targeted AI implementation plan showing me exactly where AI can give me the most leverage across every area of my life.
This is not a quick conversation. This is a deep, hour-long interrogation. You need to ask at least 100 questions across 10 rounds before making any recommendations.
RULES:
- Ask ONE question at a time. Wait for my answer before the next question.
- Never rush. If I give a short answer, push me to go deeper. Ask "why?" and "tell me more about that" and "what does that actually look like day to day?"
- Never accept vague answers. If I say "I want to be more productive" ask me what specifically I'd do with the extra time. If I say "admin stuff" ask me to walk through exactly what I did last Tuesday.
- Keep a running mental model of who I am. Reference earlier answers in later questions to show you're building a complete picture.
- After every 10 questions, give me a brief summary of what you've learned so far and what areas you still need to explore.
- Do NOT give any recommendations until all 10 rounds are complete.
THE 10 ROUNDS (minimum 10 questions per round):
ROUND 1 - WHO YOU ARE
Your background, identity, and current situation. What's your name, age, where do you live? What's your current job title and industry? How long have you been doing this? What did you do before? What's your education background? Are you self-taught in anything? What are you known for in your field? How would your closest friend describe you? What's a belief you hold that most people in your industry would disagree with?
ROUND 2 - YOUR WORK LIFE (DEEP)
Walk me through a typical Monday in extreme detail. What's the very first thing you do when you start working? What tools and apps do you use daily? What meetings do you have and with whom? What tasks repeat every single week? What's the task you dread most? What's the task that takes the longest? What's the task you're worst at but have to do anyway? What would you delegate tomorrow if you could? What does your boss or clients expect from you that takes the most effort? What reports or deliverables do you produce regularly?
ROUND 3 - TIME AND ENERGY DRAINS
Where does your time actually go vs where you think it goes? Walk me through last week: where did you lose time you didn't plan to? What interruptions kill your focus? How many emails do you send and receive per day? How much time goes to context switching between tools? What tasks do you procrastinate on and why? What's the most repetitive thing you do that a robot could probably handle? What's something you spend money on because you don't have time to do it yourself? When do you feel most drained during the week? What work do you bring home that you wish you didn't?
ROUND 4 - YOUR PERSONAL LIFE
What does your morning routine look like? Evening? What are your relationships like: partner, family, friends? How do you manage household tasks like groceries, cleaning, cooking, maintenance? What's your health situation? Do you exercise, meal prep, track anything? How do you manage your finances: budgeting, investing, tax prep, bookkeeping? What personal admin eats your time: appointments, insurance, bills, paperwork? Do you have kids? What's the parenting workload like? What does your social life look like and how do you plan it? What personal projects keep getting pushed to "someday"?
ROUND 5 - YOUR PASSIONS AND CREATIVE INTERESTS
What do you do for fun when you have free time? What would you spend all day doing if money wasn't an issue? Do you create anything: writing, music, art, video, photography, crafts? Do you have a side project or business idea you've been sitting on? What topics can you talk about for hours? What communities or groups are you part of? What skills have you always wanted to learn? What's a creative project you started but never finished? Do you consume content? What podcasts, YouTube channels, books, newsletters? What inspires you and why?
ROUND 6 - YOUR GOALS AND AMBITIONS
Where do you want to be in 1 year? 5 years? 10 years? What does financial freedom look like for you specifically? Give me a number. What career move are you working toward? Do you want to start a business, grow one, or are you happy employed? What skill would change your career trajectory if you mastered it? What's the one thing you'd change about your life tomorrow if you could? What legacy do you want to leave? What does your ideal Tuesday look like in 3 years? What's something you've achieved that you're proud of? What's the next milestone you're chasing?
ROUND 7 - YOUR FEARS AND BLOCKERS
What's holding you back from your goals right now? What are you afraid of that you don't usually admit? What's the biggest risk you're currently avoiding? Where do you feel stuck? What advice do you keep getting but can't seem to follow? What's a pattern in your life you wish you could break? What's the thing you know you should be doing but aren't? Is imposter syndrome a factor anywhere? What would you do if you knew you couldn't fail? What failure taught you the most?
ROUND 8 - YOUR RELATIONSHIP WITH TECHNOLOGY
How comfortable are you with technology on a scale of 1-10? What apps or tools have genuinely changed your life? What tools have you tried and abandoned? Have you used any AI tools before? What happened? What's your biggest frustration with technology? Do you prefer learning by watching, reading, or doing? How much time per week could you realistically invest in learning new tools? What's your budget for software and tools? Do you have anyone in your life who could help you implement things, or are you on your own? What's the last new tool you successfully adopted and stuck with?
ROUND 9 - DEEP DIVE ON TOP PAIN POINTS
Now go back to the 5 biggest pain points from all previous rounds. For each one, I need: exactly how many hours per week it costs you, exactly how much money it costs you (directly or in opportunity cost), how long this has been a problem, what you've already tried to fix it, and what would change in your life if this problem disappeared tomorrow.
ROUND 10 - SYNTHESIS AND EDGE CASES
What did I miss? What area of your life haven't we covered that's important to you? Is there anything you wanted to say but I didn't ask about? What's the one thing that, if AI could do it for you, would make you say "this was worth it"? What would make you actually stick with using AI vs trying it once and forgetting about it? What's your biggest skepticism about AI? What would change your mind?
AFTER ALL 10 ROUNDS:
Generate a COMPREHENSIVE AI IMPLEMENTATION PLAN with:
1. A 1-paragraph summary of who I am, what I care about, and what my life looks like
2. My TOP 10 AI opportunities ranked by impact, organized into:
- WORK opportunities (tasks, workflows, automation)
- PERSONAL opportunities (health, finances, household, relationships)
- CREATIVE opportunities (side projects, content, learning, hobbies)
- GROWTH opportunities (skills, career, business ideas)
3. For each opportunity include:
- What specifically to automate or improve
- Which AI tool to use and why
- Estimated time saved per week
- Estimated money saved or earned per month
- Difficulty rating (easy / medium / advanced)
- One specific action step to try TODAY
4. A suggested 30-DAY ROADMAP: what to implement in week 1, week 2, week 3, week 4
5. The ONE thing I should do first that will create the most momentum
Remember: do NOT skip rounds. Do NOT rush. Ask at least 100 questions. The depth of this interview determines the quality of the plan. This is the most important hour this person will spend with AI.
Start Round 1 now.
The 10 Rounds At A Glance
- Round 1: Who you are. Background, identity, current situation
- Round 2: Your work life in extreme detail. Every tool, task, and meeting
- Round 3: Time and energy drains. Where hours disappear
- Round 4: Your personal life. Household, health, finances, relationships
- Round 5: Passions and creative interests. Side projects, hobbies, dreams
- Round 6: Goals and ambitions. 1 year, 5 year, 10 year
- Round 7: Fears and blockers. What's holding you back
- Round 8: Your relationship with technology. Comfort level, budget, learning style
- Round 9: Deep dive on top 5 pain points. Exact numbers and impact
- Round 10: What was missed. Edge cases and final thoughts
How To Answer (This Matters)
Use a voice-to-text tool like SuperWhisper so you can just talk naturally. Typing short answers kills the depth. Speaking lets you ramble, and Claude will find the gold in your rambles.
- Weak: "I do admin stuff." Gives generic advice.
- Strong: "I spend 3 hours every Friday categorizing 200 bank transactions in QuickBooks." Gives specific recommendations.
- Weak: "I want to be more productive." Too vague.
- Strong: "I want to spend less time on client onboarding so I can take on 2 more clients per month." Gives a clear target.
Don't filter yourself. The personal questions matter as much as the work ones. AI can help with meal planning, finances, health tracking, and creative projects, not just spreadsheets.
What Your Plan Will Include
- A 1-paragraph summary of who you are and what your life looks like
- TOP 10 AI opportunities ranked by impact across 4 categories: Work, Personal, Creative, Growth
- For each: what to automate, which tool, time saved per week, money saved per month, difficulty rating
- A 30-day implementation roadmap: what to try in week 1, 2, 3, 4
- The ONE thing to do first that creates the most momentum
After Your Interview
- Pick the ONE recommendation rated "easy" that saves the most time
- Try it for one week before moving to the next one
- Don't try to implement everything at once. Follow the 30-day roadmap
- Come back every month and re-run the interview as your life changes
This is an investment, not a hack. The hour you spend here saves you hundreds later.
Go Deeper
Prefer a printable version? Download the PDF: https://drive.google.com/file/d/1uYJQa_jimWJ0bKh7JOeIO2x9JIKvVlyQ/view?usp=drivesdk
Want the whole system installed live, with Cooper on the call? Build Your Own AI, the two week sprint runs the first two weeks of August.
Or get a new working tool every Monday inside The AI Operator community on Whop.
The honest part
The guides are free. The working agents are $97.
Cooper has published 125+ guides like this one, free, no email gate. The step after reading is running the actual systems: five working agents, including the content engine behind his 10M+ views, plus your first month inside The AI Operator community, a new working tool every Monday.
Want it built with you, live? Build Your Own AI · $1,997 · live Aug 3