Thought provoking questions to start a conversation

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

Ramit Sethi · November 18th, 2016

The scene is a familiar one. You’re trying to start a conversation with someone. Maybe it’s someone you just met — a date, a potential client, or someone at an event. Or, maybe it’s even the family dinner table or out for a coffee with a friend.

But the conversation goes nowhere. You ask a question. They answer briefly. You ask another question, they answer again. You wait for them to take the helm. But nothing. The silence fills the room. Uneasy, you try again. How did you become the awkward one here?

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Luckily, 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 thought provoking questions ready to ask anytime you feel the conversation lull.

I used to hate events. But 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 to start a genuine, long-lasting conversation.

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 5 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.)

5 thought-provoking questions and why they work

1. “What do you mean by that?”
(Variation: “I’ve never heard of that. How does that work?”)

Why this question 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.

As a bonus, they’ll usually be thrilled to elaborate. Remember, they are nervous about the conversation, too. But allowing them the floor, you’re calming their fear of being boring or talking too much.

2. “What made you decide to do X?”
(Variation: “How did you get into that?”)

Why this question 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.

3. “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 question 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.

4. “Why do you say that?”
(Variation: “Now, I would have thought X, but you just said Y.”)

Why this question 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.

5. “What was the hardest part about X?”
(Variation: “If you had to do X again, what would you do differently?”)

Why this question 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 really start thinking 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 thoughtful questions

Thoughtful 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.

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

“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.

“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?”

“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 a thoughtful 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:

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

Them: “Wow, what do you think about that crazy fire that just happened in California?”
You: “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 PhD-researched thesis. They just want to know a couple of thoughts and move on.

Bonus strategy: 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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  1. Brilliant post and lots of excellent ideas as well. But I have to add telling someone “Tell me something I don’t know” sparks an interesting conversation between you two. I’ve tried it with everyone and I always end up befriending the person.

  2. “telling someone “Tell me something I don’t know” sparks an interesting conversation”

    Which context do you use it in, David? Where I’m from, we have the tendency to use “Tell me something I don’t know” in a very sarcastic, shady kind of way, lol.

    It usually ends in laughs and every once in a while, serious discussion.

  3. I’m the individual who leans against the wall, twiddling my thumbs, because I don’t know what the fudge to say. Or, when I do try to say something, I end up having a nervous tone in my voice and a minor anxiety attack. Which causes me to sink away in the background even more.

    So, I thank you for posting this because I do believe this will help me and I’m going to give it a test run since my job involves me interacting with the public on a regular basis (A very hard to please public, mind you).

    This is something that needs to be taught in schools, imo.

  4. Brilliant article with lots of tips. Actually, it depends on which country you are in, some people like straight forward questions and think you are weirdo if you you speak in a different way. But know where and how to talk makes sense. So travel more guys and you will see the difference in phrases people use. anyway, thanks for examples.