The Art of Asking Questions!

I’ve started to notice something lately. The same person can give completely different answers depending on who is asking the questions. It’s the way the questions are shaped.

Some questions are like keys. They open doors to deep, layered answers. The kind that you can’t fully understand at first. You have to sit with them, turn them over in your mind, decode what they really mean. These are not answers you just listen to/follow up. They’re answers you live with for a while.

Then there are questions that start simple and slowly climb higher. They build a bridge between everyday thinking and high-level thinking. Those questions make the other person explain their complex ideas in a way anyone can follow. It’s not just about getting the answer it’s about watching how they translate their thoughts for different minds.

Sometimes, the smartest way to ask is to make the problem universal. Not like, here’s my specific problem, what should I do? But, here’s a challenge that many people face, how would you solve it? This pulls the other person out of just giving you advice, and into sharing their own battle tested methods. And those methods are often more useful than a ready made solution.

But here’s the thing. We can’t force a conversation like this. When it’s interesting, it flows on its own. When you talk to someone who’s seen a lot, someone with high agency, the goal shouldn’t be to squeeze out one answer for one problem. It should be to understand how they see the world, how they connect the dots, how they think when there’s no ready answer in front of them.

Because once we learn how they think, we start solving problems we didn’t even know were coming.

Cheers

PS: Figuring out & Think School

Check out the previous post: The Real Game!

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