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7 proven conversation questions (and why they work)

Effective, engaging questions aren’t picked randomly from a list. For questions to be really great, you have to understand why they work and when to use them.

Ramit Sethi · April 8th, 2016

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.

It doesn’t have to be this way. Ever. 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:

Quiz: What is your earning potential? Choose the answer you agree with the most
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  • 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, it’s 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.

How to connect more deeply with questions

Great conversations are all about give and take. Both people should be sharing and adding value — not one person asking question, question, question, question.

If you find yourself asking too many questions, you can use one of these strategies to tip the balance and keep the conversation flowing naturally.

Strategy 1: Question, question, statement
You’re not adding any value to the conversation if you’re just asking questions. A good rule of thumb is to ask two to three questions and then make a statement.

Bad example:
“Where are you from? How long have you been there? Oh, do you like it? What brought you here?”

Good example:
“Where are you from?” “I’m from Michigan.” “Oh, I’ve been to Michigan before. I actually grew up in Phoenix, but I live in Chicago now, pretty close by.” “Oh, really? So how long have you been there?”

Instead of acting like an interrogator, you’ve engaged this other person. You very subtly made a connection.

Strategy 2: Give observational compliments
Complimenting someone in a thoughtful, authentic way can be one of the best things you do to engage them in the conversation. The best part of all? If you do it authentically, it makes them feel good. This is not as simple as, “Nice dress,” or “I like your shirt.” The observational compliment goes one step further.

Bad example:
“You’re the bravest and smartest person I’ve ever met. How can I be more like that?”

This is not authentic and people can feel that. They are thinking, “Why are you such a weirdo,” or “What do you want from me?”

Good example:
“You know, you seem pretty adventurous. I know a lot of management consultants, and I don’t know any of them who would do scuba diving in their off time. How did you get into that?”

Notice the difference in what just happened there. This person feels great. They like you because you have made an observation that happens to be accurate about them. We all love to be told something about ourselves. And you showed you were really listening to what they had to say.

Strategy 3: Have an opinion
One of the things that kills conversations is when people don’t have an opinion on anything. Imagine talking to someone who only asked questions but never shared their own thoughts. You’d have no idea what they’re about. You wouldn’t feel connected or be able to trust them.

That’s why it’s critical to express your thoughts and opinions. Here’s what I mean:

Bad example:
“Wow, what do you think about that crazy fire that just happened in California?”
“Oh, yeah. I don’t know too much about it.”

Good example:
“Wow, what do you think about that crazy fire that just happened in California?”
“I saw that on the news! I just heard a quick soundbite but it sounded like it was started by some dumb kid hikers. Have you seen any more about what happened?”

In the moment, you might think, “I don’t really know enough about the topic to add any value to this discussion.” That’s an invisible script at work. The truth is no one is looking for a Ph.D.-researched thesis. They just want to know a couple of thoughts and move on.

Strategy 4: Become unshakeable
We all know someone who is completely comfortable in almost any situation. They can walk into a conference or a bar, and you’d think they knew everyone there.

How did they get that way?

It wasn’t luck, or genetics, or the “it factor” (whatever that is). It’s a skill. You can develop confidence, too.

I used to feel uncomfortable and out of place. But over time I’ve developed hacks for confidence in new situations. I’ll show you exactly how I do it in these 3 short videos. Just enter your email for instant access.

3 tactics for unshakeable confidence in any conversation.

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