What if your smartest teammate never got tired, never lost focus, and always knew just the right question to ask?
For months, I’d been using ChatGPT like most people do, a capable assistant, helpful for outlining documents, summarizing ideas, and speeding up content. But I always felt like something was missing.
It wasn’t pushing me. It wasn’t making me better.
Until I changed one thing: the prompt.
From Assistant to Challenger
Instead of asking ChatGPT to agree with me, I asked it to argue with me. To challenge my assumptions. To stop being polite.
I created what I now call a Thinking Partner Prompt, a carefully designed instruction set that turns ChatGPT into an intellectual sparring partner.
The first time I used it, I froze. It asked a question that hit me right between the eyes:
“Are you sure the server is the root problem… or just a symptom of something deeper?”
That moment changed everything. And it became the beginning of a new way of working.
Why This Matters
Most people use AI to stay in their comfort zone. But growth lives on the other side of resistance. When you train ChatGPT to push you, it:
- Surfaces blind spots
- Stress-tests your strategy
- Exposes vague assumptions
- Sharpens your implementation plans
- Forces you to earn your confidence
In other words, it turns every project into a clarity machine.
What I Built
Over the course of a week, I refined a set of prompts that can now:
- Diagnose strategic gaps
- Challenge execution assumptions
- Walk through problem diagnosis
- Reframe decisions before they get costly
These prompts became a reusable framework I’m calling the Thinking Partner Series. And yes, you’ll be able to get access to it.
Want the Prompt?
I’m updating my free guide, Turn ChatGPT Into Your Smartest Teammate, with everything I’ve learned from this experiment, including:
- The full Thinking Partner Prompt
- Variants for strategy, problem-solving, and implementation
- How to use it one question at a time
- Why one good question beats ten mediocre answers
If you want the guide when it drops, join my email list here or follow me on your favorite platform. I’ll be sharing pieces of this journey over the next few weeks.
Final Thought
Tools don’t change us. Questions do.
And when your tools start asking better questions, you start thinking like the person you're trying to become.
Follow for more. This is only the beginning.
#PromptDesign #ThinkingPartner #AIProductivity #ChatGPT #InnovationTools #DigitalClarity
