Bonus Feature
How to Turn ChatGPT (or Any AI) Into Your 24/7 Executive Coach
Imagine having a no-BS executive coach that knows your goals, your flaws, your finances, and even your posture—available 24/7, never distracted, never judgmental. That’s exactly what you can do with a bit of creativity with prompts. The result? A custom-built AI sidekick that helps you make better decisions across career, health, money, and more!
Disclaimer...this can seem a bit intrusive to many. If you decide to try something like this only put in information you are comfortable sharing, the steps below are just suggestions. Don't enter in personally identifiable information like address, phone #, SSN, account numbers, email addresses, or full names. Hint: Use a nickname or callsign.
I try to keep some things generic with a mindset of "if this was seen by anyone else, would they be able do anything nefarious with it".
Step 1: Let ChatGPT Interview You
Before ChatGPT can be your advisor, it needs to know you like your therapist does. Start by prompting ChatGPT to “ask me everything you need to know to understand who I am, how I think, and what I want out of life.”
Then—brace yourself—answer every question. Spend some time here, provide detailed and honest answers.
Your Move
- Ask ChatGPT: “Make a list of questions to fully understand me—my values, goals, habits, fears, the whole deal.”
- Answer them honestly and thoroughly. More data = better results.
Step 2: Ask Your Network for Feedback
Think you know yourself? Your friends might disagree. Create a simple 2-question Google Form and send it to 10+ people in your circle to get unfiltered feedback.
Then feed those responses to ChatGPT. Boom—instant outside perspective.
Your Move
- Ask your network: “What’s one thing I do really well?” and “What’s one thing I could improve?”
- Copy/paste their (anonymous) replies into your AI’s brain.
Step 3: Feed the Beast (with Boundaries)
Don't stop at personality quizzes. Load ChatGPT with data about your:
- Favorite books
- Favorite foods
- Financial details (estimates...don't link your bank account!)
- Current or desired job description
- Professional development goals
- Military career highlights
- Military job
- Education and/or professional certifications
- Fitness and diet logs
- Bloodwork results
- Posture photos (seriously)
- Style preferences and body measurements
What happens next? The AI starts connecting dots. It gives better advice, surfaces insights you missed, and becomes a personalized strategy machine.
Your Move Upload info based on your goals. Examples:
- Mindset: Books you live by, long-term goals, your “why”
- Job Performance: Performance reports
- Money: Income, savings, net worth breakdown
- Health: Diet logs, lab results, wearable data
- Style: Size charts, preferred brands, past purchases
Step 4: Give It Killer Instructions
Treat ChatGPT like a team of specialists. Use different Projects to keep advice tailored—like “Networking Strategies,” “Health Optimization,” or “Style Advisor.”
Use crystal-clear prompts with specific tones, frameworks, and expectations.
Your Move Set up a few dedicated Projects and include:
- A description of what the AI should know and how to act
- Tone preferences (e.g., “speak like a McKinsey consultant with a sense of humor”)
- Clear deliverables (e.g., “build me a wardrobe itinerary for job interviews with links”)
✅ Your AI Coach Setup Checklist
Here’s a quick-and-dirty guide to replicate this AI system:
🔍 Build Your Profile
- Ask ChatGPT to interview you
- Answer in detail (seriously, don’t skimp)
- Upload your “life playbook”—books, values, routines
🗣 Get Outside Feedback
- Send 2-question survey to friends/family
- Upload responses to ChatGPT
📊 Add Relevant Data
- Finance: net worth, budgets, savings goals
- Business: KPIs, bottlenecks, dashboards
- Health: bloodwork, diet logs, fitness goals
- Anything else that matters
🗂 Organize Projects Smartly
- Use separate Projects for different life domains
- Include context, tone preferences, and references
The Bottom Line
The secret isn’t just using AI—it’s training it. Challenge responses, push back, and refine your prompts until the advice is genuinely useful. When ChatGPT spits out junk, tell it why and ask for a better answer.
The result? An executive coach who never sleeps, doesn’t judge, and knows you well enough to give you customized advice.
⚠️ Pro Tip: This works with any LLM—Claude, Gemini, whatever. The magic is in the setup, not the tool.
Start with what matters most to you. Test. Refine. Repeat. And don’t be afraid to tell your AI when it’s being an idiot.