Asking the right questions is not to look for an answer.
Take a sip and feel the rush. Sit still and don’t move. Let the surge reverberate. Hear your heart pound and your veins expand. Drop the cup just to lift it again for another sip. For in your hand sits more than a cup of coffee.
Recently, I needed a fertility check-up. The “normal” route—doctor, referral, labs, wait, follow-up—meant seven steps and weeks of clock-watching.
Instead, I asked ChatGPT which tests to run, walked into a cash-pay lab, then fed the results back into another model. Three days, start to finish.
The reframing was everything. I stopped asking “How do I navigate healthcare?” and started asking “How do I get reliable data about my body?”
Consider how often we do this: A startup wants to “disrupt education” by making online courses more engaging. But they never ask whether courses are the right format.
A company wants to “reduce meetings” with a day without them. But they never ask why there were so many meetings in the first place.
We optimize the wrong things because we accept the wrong framings.
This is metacognition in action - thinking about thinking, questioning about questioning. It’s the difference between being trapped by someone else’s problem definition and having the freedom to see what’s really needed.
But here’s where it gets dangerous with AI. Ask ChatGPT: “help Carlo run a fertility health check in the most optimized way.” What will it give you?
It will optimize within the existing healthcare framework—better appointment scheduling, faster lab results, and more efficient referrals. It will never question whether you need the framework at all.
This is how easily we miss what’s important. This is how we are misusing AI. This is how we hand over our thinking to machines before doing the thinking about thinking ourselves.
Thus, turning ourselves into commodities in a world obsessed with content, knowledge, and THE answer. That is scary.
Can you sense the warm home feeling it delivers? The familiarity. The connection it builds on a simple interaction we recognize so deeply that it makes us friends in a mere few words.
Instead of providing information, it creates space for connection. Three words. Infinite possibility.
This is what the question creates.
It slips past transaction and sparks rapport. That tiny prompt is metacognition in miniature.
And this is exactly your litmus test for how hard this is to grasp, yet how crucial and powerful it is, especially in the context of AI.
And the best part, AI can help you bridge that chasm, too.
Don’t use it as Google. Use it as a thinking partner to elevate your cognitive faculties. To traverse the abstraction layers of meta-cognition. Ask it about reasoning and how it came to things.
Avoid confirming your bias in yes, you did great or no, you did badly. In other words, and not sounding like a broken record, ask it questions that do not provide an answer.
Instead, they can share a frame, a model, multiple options, a learning about learning. And then my friend, you are playing in a league of your own, drinking coffee with or without sugar.
Until next time,
Carlo
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