We've all been there. You're at an event, you meet someone new, and the conversation gets stuck on boring small talk.
Questions like "What do you do?" or "Where are you from?" often lead to one-word answers and awkward silence.
But great conversationalists know a secret: People love to talk about what they value most. The best way to build a real connection is to ask questions that show you are genuinely interested in them.
Here are 10 smart questions that will help you move past the boring stuff and build real friendships and professional connections.
The Secret: Ask About Values, Not Just Facts
The fastest way to connect with someone is to make them feel important. When you ask good questions, you show you are really listening. This makes you seem more trustworthy.
A simple rule to remember is that people enjoy talking about themselves and their own interests. Use these questions to unlock a much better conversation.
1. Instead of the "Naked Job" Question
Instead of asking: "What do you do?"
Ask this: "How do you spend most of your time?"
Why it works: The "What do you do?" question can be awkward. Some people might be between jobs, retired, or a stay-at-home parent. This new question is more graceful. It lets people talk about their job if they love it, or their hobbies and passions if they prefer.
2. Instead of the "Naked City" Question
Instead of asking: "Where are you from?"
Ask this: "What's one interesting thing happening in your hometown right now?"
Why it works: A simple answer like "Denver" can kill the conversation. This new question invites them to share a cool fact or a story about their city. It gives you something interesting to talk about next.
3. Find Their Passion
Instead of asking: "Is your job busy?"
Ask this: "What's the most exciting (or challenging) thing happening in your line of work right now?"
Why it works: This shows you are truly curious about their world. It lets them "geek out" about their job or even their favorite hobby. They will feel like you are an "insider" who really wants to understand them.
4. Ask What Makes Them Proud
Instead of asking: "What are your hobbies?"
Ask this: "What's something you've accomplished in the last year that you're really proud of?"
Why it works: People love to be recognized for their hard work. This question asks them to share a success, whether it's big or small. It helps you understand what is truly important to them.
5. Be a "Word Detective"
How it works: Listen closely for an odd or interesting word they use. If a lawyer mentions "my garden" or an artist mentions "my dog," that's your clue.
Ask this: "You just mentioned [the interesting word, like 'your garden']. Can you tell me more about that?"
Why it works: This proves you are paying close attention. It also lets them switch to a topic they really want to talk about, which makes them feel close to you.
6. Ask About Feelings, Not Just Ideas
Instead of asking: "Is that a good idea?"
Ask this: "What part of that idea makes you feel the most excited?"
Why it works: This question goes beyond logic and asks about their feelings. It shows you care about their excitement, not just their plan. This builds a much deeper, more personal connection.
7. Ask for a Story
Instead of asking: "How long have you worked there?"
Ask this: "What's the story behind how you got into this field?"
Why it works: People love to tell their own stories. This question invites them to be the hero of their own journey. Their story is almost always more interesting than a simple number.
8. Turn a Compliment Around
How it works: When someone gives you a compliment, don't just say "thanks." Use it as a chance to compliment them back.
If they say: "I love that tie!"
You say: "Thank you! That's kind of you to notice. You must have a great eye for detail."
Why it works: You praise them for being smart or observant, which makes them feel good.
9. Ask About Their Dreams
Instead of asking: "What are your plans for next year?"
Ask this: "If you had a year off with all expenses paid, what new skill or hobby would you want to master?"
Why it works: This is a fun, creative question. It gets people to talk about their secret dreams and passions. It's a great way to learn what really motivates them.
10. The Unforgettable Exit Question
How it works: As you are ending the conversation, end it on a high note.
Ask this: "Of all the people you've talked to today, what was the most interesting conversation you had?"
Why it works: This question makes them feel like an important, smart person whose opinion matters. (And if they say, "This one!" you know you've made a great connection.) It makes you memorable long after you've walked away.