7 Great conversation questions (and why they work)

You’re quietly sitting at a table full of strangers. The kind of strangers you might like to impress — industry leaders, potential clients, or even your new in-laws. But it seems like nobody has anything to say. You can almost hear the Jeopardy theme song play softly somewhere in the background. This is the stuff nightmares are made of. But great conversation questions can get the ball rolling.

The easy fix — the way to instantly build a connection with people (even strangers) is to have engaging questions ready to ask anytime you feel the conversation lull.

But, it’s not as simple as picking a random question off of a list of 101 Great Conversation Questions. That just moves you from awkward to painfully awkward and predictable. Or worse, you end up being one of these people:

• The Interrogator. Rattling off 100 questions makes people feel like they are being interviewed — or worse. Where do you live? What do you do? What’s that like? It comes off way too aggressive.
• Mr. Generic. Boring, generic, overused questions get boring, generic answers. Where did you grow up Ohh, that’s so interesting. Any hobbies? We’ve talked about our hobbies our whole lives. Nobody wants to talk about hobbies anymore.
• Needy & Nervous. Sharing everything at once because this is their chance. Let me tell you what I do. First, I do this, but I also do that, and two years ago, I started this, and on the side, I do that. What about that Did you know about this At this point, everyone’s eyes glaze over. You palpably feel the energy drain from the group.

I know because I’ve done all three. Now, put me in front of anyone and within two or three minutes, we can find something in common and we can talk about it. Could be dating, living in a certain city, education, or even scuba diving. This isn’t because I’m ‘naturally’ good at social skills, but because I’ve studied and tested how great conversations work.

I used to hate events, but now I host meetups all over the world for my readers.

The truth is, you don’t need 100 questions, just a few of the right ones. The key is knowing how and when to use them to spark connection and create a natural, flowing conversation…almost effortlessly.

I’m going to show you the only 7 questions you need to know for consistently great conversations. And, more importantly, I’ll show you why they work.

(As a bonus, I’ll go even deeper. I’ll give you simple guidelines to keep the conversation going and create a lasting, positive impression on anybody you meet.)

7 conversation-sparking questions and why they work

How do you know X?
Variation: What brought you here?
Why this works: If you’re at a party or event, its easy to establish common ground. There may be a connection right off the bat. Or, worst case scenario, you have completely different stories and you can use that to ask more questions.

What do you mean by that?
Variation: I’ve never heard of that. How does that work?

Why this works: We naturally don’t want to ask for clarification. It makes us look dumb, we feel foolish, we wonder if we missed something that everyone else got. The tactic here is to think of yourself as the curious beginner. You actually making other people feel comfortable by asking the questions that everyone else wants answered.

What made you decide to do X?
Variation: How did you get into that?
Why this works: People love to talk about themselves. This question prompts a story and you can pull out elements of the story to make a connection. You could learn you had the same major in college or worked in the same industry — then the conversation becomes natural from there.

What’s been your favorite part about X?
Variation: I really liked [X speaker, the flowers, this venue] today, did you have a favorite?
Why this works: Like above, you are making a connection and eliciting an opinion. This question gets fun when you offer your favorite part of the day and they don’t agree at all. I’ve seen this at events about speakers. Really I thought he was the least engaging? People could talk about their preferences all night.

What’s your favorite restaurant in this city?
Variation: Where’s a place I can go tomorrow where I won’t find any tourists?
Why this works: People love being the ?expert.? If you’re in a new city and meet a local, they’re sure to have all kinds of tips about the best things to do. The best part is, you walk away with information to use right away.

Why do you say that?
Variation: Now, I would have thought X, but you just said Y.
Why this works: Often people make nonchalant statements about their industry, their city, or their background like, It’s a terrible industry to get into right now,? And then promptly move on. By asking for more details, you show you’re listening and are truly interested.

What was the hardest part about X?
Variation: If you had to do X again, what would you do differently?
Why this works: People love talking about overcoming adversity. It’s an instant connection when the conversation involves emotions. This also works well when you meet someone you admire — an author, a speaker, or a leader in your industry. You can learn counterintuitive lessons about something you’re trying to do.

Ask people any of these questions and gauge their response. See if their eyes light up and they start answering you in really engaging ways or if they give you one- or two-word answers. By doing so, you’ll build up a toolbox of proven questions you can use in any situation. You can even test your own questions to add to your toolbox.