Hey Solopreneurs,,
Most solopreneurs are using AI like it’s 2019 Google search. They’re leaving 90% of its potential on the table.
Today, I’m breaking down the 5 Levels of Context Prompting – a framework that transforms AI from a generic search engine into your personal business strategist.
🚨 The Problem Most People Don’t See
You ask ChatGPT: “How do I grow my newsletter?”
It spits out generic advice that could apply to anyone, anywhere, in any niche.
Why? Because AI knows everything about the world but nothing about YOU.
That’s about to change.
Level 1: Chat & Ask Anything
Status: Google Replacement Mode
This is where 95% of users get stuck:
• You ask random questions - AI gives random answer
• Zero personalization - Maximum frustration
Example: “Write me a marketing strategy”
Result: Generic fluff that sounds like it came from a 2010 blog post
What’s Actually Happening:
• AI treats you like a stranger (because you are one)
• No context about your business, audience, or goals
• Responds with one-size-fits-all advice
When This Level Works: Quick fact-checking, general research, or when you genuinely want broad, universal information.
The Bottom Line: You’re treating a Ferrari like a bicycle. Time to level up.
Level 2: Unlock Hidden Trigger Words
Status: Secret Code Activated
Here’s what most people don’t know: AI models have programmed trigger words that unlock deeper, more detailed responses.
Power Words That Transform Your Output:
• “Deep dive into...”
• “Comprehensive analysis of...”
• “Step-by-step breakdown...”
• “Detailed framework for...”
• “Advanced strategies for...”
Before: “Help me with email marketing”
After: “Deep dive into advanced email marketing strategies for solopreneurs”
The Difference: Night and day. Same AI, 10x better output.
What’s Actually Happening:
• These trigger words activate different response patterns in the AI
• The model interprets “deep dive” as a signal to provide more thorough, research-heavy content
• Length and detail of responses dramatically increase
• AI pulls from more specialized knowledge instead of surface-level information
Why This Works: AI models are trained to recognize intent signals. Certain phrases tell the AI “This person wants expert-level detail, not casual advice.”
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This includes 48 Idea Prompts, 4 Newsletter templates and linking all AI Prompts
The Problem: You don’t know what trigger words work for different models. It’s trial and error.
Level 3: Program Your Personal AI Assistant
Status: Context-Aware Partner
This is where things get interesting. You’re going to teach AI about YOU.
Use System Prompts to Set Your Preferences:
“For all responses, follow these guidelines:
• Structure answers in bullet points
• Keep language conversational and direct
• Focus on actionable steps over theory
• Include specific examples when possible
• Write for busy entrepreneurs who value time”
What Happens: AI now responds in YOUR preferred style, every single time. No more reformatting. No more generic tone.
What’s Actually Happening:
• System prompts act like permanent instructions that apply to every conversation
• AI stores your preferences and applies them automatically to all responses
• You’re essentially programming the AI’s “personality” to match your communication style
• The AI references these instructions before crafting every response
Why This Changes Everything:
• Eliminates the need to repeat formatting preferences in every prompt
• Creates consistency across all your AI interactions
• Saves massive amounts of time on post-editing •
Pro Tip: Set this once in Claude or ChatGPT settings, and every conversation becomes personalized to your communication style.
Level 4: Create Your AI Business Partner
Status: Project-Specific Genius
This is the game-changer. You’re not just giving AI information about you – you’re giving it information about your specific project.
Here’s How:
• Create a dedicated project in ChatGPT
• Upload your business plan, target audience research, past content
• Include your goals, constraints, and success metrics
• Add competitor analysis and market positioning
Example Project Context: “I’m building a productivity newsletter for remote workers aged 35-50. My goal is 10K subscribers in 6 months. My writing style is casual but informative. Budget: $500/month. Main constraint: Limited time (5 hours/week).”
The Result: AI now answers through the lens of YOUR specific project. Every suggestion is tailored to your audience, budget, timeline, and goals.
What’s Actually Happening:
• AI creates a knowledge base specific to your project
• Every response is filtered through your project’s context, constraints, and objective
• The AI “remembers” your business details and applies them to every answer
• Instead of generic advice, you get recommendations that fit your exact situation
Why This Is a Superpower:
• AI becomes like having a co-founder who knows your business inside and out
• No more irrelevant suggestions (like “hire a team of 10” when you’re a solopreneur)
• Every piece of advice is pre-filtered for your budget, timeline, and audience
This is a superpower. AI becomes your co-founder who knows your business inside and out.
Level 5: AI That Questions Itself
Status: Self-Correcting Perfectionist
The final level: Make AI evaluate and improve its own responses.
Add These Auto-Evaluation Prompts:
• “Rate your confidence in this advice on a scale of 1-10”
• “Adjust the creativity level to 7/10 for this response”
• “Question your assumptions and provide alternative viewpoints”
• “Identify potential risks or downsides to this strategy”
Advanced Example: “Create a content calendar for my newsletter, then rate your confidence in each topic suggestion (1-10) and explain your reasoning. If any topic scores below 8, provide better alternatives.”
What Happens:
• AI shows its work
• Provides confidence scores
• Self-corrects weak suggestions
• Gives you probability assessments
What’s Actually Happening:
• You’re activating the AI’s “metacognitive” abilities : thinking about its own thinking
• The AI runs internal quality checks on its responses before delivering them
• Confidence scores help you identify which advice to trust most
• Self-evaluation forces the AI to consider multiple angles and potential failures
Why This Is The Ultimate Level:
• You get transparency into the AI’s reasoning process
• Weak suggestions get filtered out automatically
• You can dial up/down specific qualities (creativity, risk-taking, conservativeness)
• The AI becomes a more critical thinking partner, not just an answer machine
• You can spot potential blind spots before implementing advice
You get responses that are not just better – they’re transparently better.
The Bottom Line
Most solopreneurs are using AI like a search engine when they should be using it like a business partner.
The difference between Level 1 and Level 5 prompting isn’t just better answers – it’s the difference between generic advice and personalized strategy.
Start climbing the ladder. Your future self will thank you.
What level are you currently at? Hit reply and let me know , I read every single response.
Your Biggest Fan,
Mike
This is excellent advice and ideas! Thank you so much for sharing! What I want to find is a humanizing prompt that removes its own footprints, like the dreaded em-dash, etc. 😄💖🦋