The Art of Asking Better Questions

Think about the best conversation you've had recently. Chances are, it wasn't because someone delivered a brilliant monologue. It was because someone asked you something that made you pause, think, and share something real.

Good questions are a skill, not a talent. And like any skill, you can get better at it with a few principles.

First: ask open questions, not closed ones. "Did you have a good weekend?" gets you a yes or no. "What was the highlight of your weekend?" gets you a story. The difference is tiny in effort and massive in outcome.

Second: follow the energy. When someone's eyes light up about a topic, go deeper. "Tell me more about that" is one of the most powerful phrases in any language. It says: I'm interested, keep going. Most people are starving to be heard.

Third: don't ask questions you could Google. "Where are you from?" is fine. "What do you miss most about where you grew up?" is better. The first is a fact. The second is a feeling. Feelings are where connection lives.

Fourth: embrace the weird. The most memorable conversations happen when someone asks something unexpected. "What's a belief you held as a kid that turned out to be wrong?" or "If you could have dinner with any fictional character, who would it be?" These questions break the script, and breaking the script is where the good stuff starts.

Fifth: be willing to go first. If you ask a vulnerable question, share your own answer. Reciprocity is the engine of connection. When you model openness, you give the other person permission to be open too.

The beautiful thing about better questions is that they don't just improve your conversations — they improve your relationships. When you consistently ask people things that matter, they feel seen. And feeling seen is the foundation of every meaningful connection.

You don't need to be charismatic or extroverted to be a great conversationalist. You just need to be genuinely curious — and willing to ask the question that everyone else is too polite to.