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AI Enablement

The 5 Best ChatGPT Prompts I Use Every Day To Grow My Business

Rob Cressy

After 1,000+ days of daily ChatGPT usage, I have built an extensive library of prompts that power my business. But here is the truth: out of hundreds of prompts, there are five that I come back to every single day. These are the ones that have the highest impact, the most versatility, and the deepest return on time invested.

These are not clever hacks or viral prompt templates. These are the foundational prompts of a real AI-first business. They work because they are rooted in how I actually think, create, and lead.

The best prompts are the ones you use every day. Consistency beats cleverness every single time.


Prompt 1: The Strategic Thinking Partner

"I'm working on [specific challenge or opportunity]. Here's the context: [background details]. I want you to think with me as a strategic advisor. Ask me the questions I should be asking myself, then help me build a plan of action."

Why This Works

Most people ask ChatGPT for answers. This prompt asks it for better questions. And better questions lead to better thinking, which leads to better decisions.

I use this every morning when I am working through my biggest priorities. It forces me to articulate what I am actually working on (which clarifies my own thinking), and then ChatGPT serves as a thinking partner who can see angles I might miss.

How I Use It

  • Business strategy sessions where I am weighing multiple options
  • Content planning when I am deciding what to create next
  • Client preparation when I am getting ready for a coaching session
  • Product development when I am building something new

The key is the phrase "think with me." It shifts ChatGPT from answer mode into co-creation mode, and the quality of the conversation improves immediately.


Prompt 2: The Voice Calibration Check

"Here is something I wrote: [paste content]. Review this through the lens of my Soul Data and voice. Does it sound like me? Where does it feel off? Give me specific suggestions to make it more authentically mine."

Why This Works

Every piece of content that goes out under my name needs to sound like me. After loading my Soul Data into ChatGPT, this prompt is how I quality-check everything. It is my personal brand filter.

ChatGPT has learned my voice, my values, and my communication style. When I run content through this prompt, it catches phrases that do not sound like me, tones that feel off, and language that does not match my energy.

How I Use It

  • Before publishing any blog post or article
  • Before sending important emails to clients or partners
  • When reviewing content that was drafted quickly and needs a polish pass
  • When adapting content for different platforms (LinkedIn vs. email vs. website)

Prompt 3: The Content Multiplier

"I have this core idea: [describe the idea or paste content]. Turn this into [number] different pieces of content for [platform]. Each one should have a different angle or hook while staying true to the core message."

Why This Works

One idea should never be one piece of content. Every good idea has at least five to ten different expressions. This prompt takes a single concept and multiplies it across formats and platforms, giving me a week's worth of content from one insight.

This is how I stay consistent without burning out. I am not coming up with new ideas every day. I am taking my best ideas and expressing them in different ways for different contexts.

How I Use It

  • Turning a coaching insight into LinkedIn posts, email newsletters, and blog content
  • Repurposing podcast episodes into written content
  • Creating social media content from frameworks and playbooks
  • Building email sequences from a single core concept

Prompt 4: The Decision Pressure Test

"I'm considering [decision or direction]. Here are the options I see: [list options]. Challenge my thinking. What am I missing? What could go wrong? What is the strongest argument for each option?"

Why This Works

We all have blind spots. Especially as entrepreneurs, it is easy to fall in love with an idea and miss the flaws. This prompt turns ChatGPT into a trusted advisor who will give you the honest feedback you need.

I use this before every major business decision. Pricing changes, new offers, partnership opportunities, marketing strategies. The cost of a bad decision is high. The cost of spending five minutes pressure-testing with ChatGPT is almost zero.

How I Use It

  • Evaluating new business opportunities or partnerships
  • Refining pricing and packaging for offers
  • Choosing between marketing strategies or content directions
  • Preparing for difficult conversations with clear thinking

Prompt 5: The Daily Intention Setter

"Based on what you know about my vision, my current priorities, and where I am heading, help me set my intention for today. What should I focus on? What should I let go of? How should I show up?"

Why This Works

This is the prompt that starts my day. It is simple, personal, and powerful. Because ChatGPT has my vision, my goals, and my current projects loaded through my AI Operating System, it can give me a focused, intentional starting point every morning.

The result is not a to-do list. It is a way of being for the day. It reminds me of what matters, what I am building toward, and how I want to show up. That intentionality carries through everything I do.

How I Use It

  • First thing every morning before diving into work
  • When I feel scattered and need to recenter
  • Before big days with multiple coaching sessions or speaking engagements
  • At the start of each week to set the tone for what is ahead

What Makes These Prompts Different

You will notice something about all five of these prompts: none of them are about getting ChatGPT to do work for you. They are all about getting ChatGPT to think with you.

That is the shift that separates high-performers from everyone else. The best AI users are not using it to replace their thinking. They are using it to amplify their thinking. These five prompts do exactly that.

They also all require context. They work best when ChatGPT knows who you are, what you are building, and how you operate. That is why your Soul Data and your AI Operating System are so important. Without that foundation, these prompts are just words. With that foundation, they become daily tools that compound over time.

The best AI practice is a daily AI practice. Five prompts, used consistently, will outperform a thousand prompts used once.


Build Your Own Daily Prompt Practice

Start with these five. Adapt them to your business. Make them your own. The goal is not to copy my exact words. The goal is to build a daily rhythm of AI-powered thinking that makes you sharper, faster, and more intentional every single day.

If you want help building a complete AI system that includes your personalized prompts, workflows, and operating system, The Unlimited Method is the place to start. Your best prompts are waiting to be discovered. Let's find them together.

Rob Cressy
Rob Cressy
AI Enablement Coach helping entrepreneurs and leaders go from AI curious to AI dangerous. 1,000+ days of daily AI usage. Host of The Undeniable Leader podcast.
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