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Why Asking a Good Question Matters

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    James Yoo
    Twitter

We live in a culture that prizes answers. Grades depend on them, interviews search for them, and Google promises them in seconds. Yet the spark of real understanding doesn't begin with an answer—it begins with a question.

A good question is more than curiosity put into words. It's a way of shaping the world. If I only ask, “Is this right or wrong?", I miss the spectrum in between. If I never ask, “What else is possible?", then my vision narrows to what already exists. The question is the frame, and the answer only fills in the picture.

This truth feels even sharper in our age of artificial intelligence. When you type a prompt into an AI, the system doesn't magically know what you want—it follows the trail you've given it. A vague prompt brings vague output, like throwing a net into the ocean without knowing what you hope to catch.

Think about the difference between typing:

  • "Tell me about Paris" vs
  • "Suggest a 2-day Paris trip plan with hidden cafés, local bookshops, and evening walks along the Seine."

The first gives you a tourist brochure. The second gives you an experience. Same AI, same tools—but a completely different outcome because the question was sharper. And it's not just about AI. In conversation, too, a good question deepens connection. Imagine talking with a friend:

  • "How was your weekend?" vs
  • "Was there anything fun over the weekend?"

The first usually gets you a polite, one-word reply: “It was fine." But the second changes the energy. It nudges the other person to pause, think, and share a story. Maybe they tell you about a new restaurant they tried, a movie that surprised them, or even admit that nothing fun happened at all. Either way, you get a glimpse into their world that the standard version would never uncover.

It works the same way in countless everyday situations:

  • When choosing dinner: instead of “What do you want to eat?" (often answered with “I don't know"), try “What are you craving tonight?" One asks for a decision; the other invites desire.
  • After watching a movie together: instead of “Did you like it?", ask “Which part stuck with you the most?" The first ends in yes/no. The second opens a doorway into how someone thinks and feels.
  • Even at work: instead of “Is everything okay with the project?", try “What's the part of this project that's been trickiest so far?" That small shift can reveal problems people might not otherwise voice.

That's why asking a good question matters: it's an act of design. A question builds the path that thought—human or machine—will follow. It takes humility to admit you don't know, and imagination to ask in a way that reveals more than just information.