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Thought provoking questions to start any conversation

Thought provoking questions are the best way to start a conversion. Small talk tips & the five most intriguing questions for work events and dates.

Ramit Sethi

It’s a situation we’ve all been through before — and it’s also every shy person’s worst nightmare: an awkward conversation with a stranger.

They typically sound something like this:

YOU: So uhhh crazy weather we’re having, huh?

THEM: Yup.

(prolonged silence)

YOU: How’s your drink?

THEM: Fine.

(prolonged silence)

YOU: Seen any good movies recently?

THEM: Nope.

(prolonged silence followed by you muttering something about going to the bathroom and shuffling off)

Do you see what happened? Almost immediately, the conversation FLAT LINES and goes absolutely nowhere.

And there are plenty of situations where this happens:

  • First dates
  • Work conventions
  • Parties
  • Family gatherings

…but the outcome is the same. You try to force small talk by asking banal questions — only to get terse, one- or two-word answers back.

Luckily, it doesn’t have to be this way. Ever.

In fact, you CAN instantly establish a connection with people — even complete strangers — with great, thought provoking questions sure to start a conversation.

The power of a perfect thought provoking question

I’ve talked before about having a story toolbox — a running list of your best stories that you can tell others. Having thought provoking questions you can use when you want to punch up a conversation creates a question toolbox — effective, deep-conversation starting questions at the ready.

To further illustrate this, I’m going to pull out a story from my very own toolbox.

Years ago, I was studying abroad. On the first night, the rest of the students and I had gone to this bar to have a drink. We didn’t really know each other, so we all just sat at our table stewing in our awkward silence.

I decided to break the ice by asking a provocative question from my toolbox.

“Hey,” I said, “let me ask you all a question: Who would you rather walk in on while they were hooking up with someone — your son or your daughter?”

Yeah, yeah. I know. The question was crude and utterly juvenile — but it WORKED. It turned out everybody at the table had an opinion so they started talking.

Boom. Ice = broken.

If you’re afraid you’re too shy to even ask a question, check out my video on tactics to overcome shyness.

Asking great questions can be one of the best ways to engage the person you’re talking to and also ingratiate yourself with them — especially when there’s a lull in the conversation. I’ll go out on a limb and say “Who would you rather walk in on…” likely doesn’t work in all situations.

That’s why I’m going to show you 5 intriguing questions for consistently engaging conversations you can use in almost any context.

5 thought provoking questions to ask during small talk

Question #1: “What do you mean by that?”

Variation: “I’ve never heard of that. How does that work?”

This question is great because we rarely ever ask for clarification during a conversation for fear of looking or sounding dumb. After all, we feel foolish if we think that we missed something everyone else got.

The trick is to go in with the mindset of a curious beginner. Be inquisitive. Ask questions when you don’t understand something and don’t be afraid to seek out more information. You’ll actually make other people feel comfortable when you ask a question everyone else wants answered.

And the person you’re asking will be thrilled to elaborate. Remember: they’re nervous about the conversation too. But by allowing them the floor, you’re calming their fear of being boring or talking too much — while providing fodder to keep the conversation going.

Question #2: “What made you decide to do X?”

Variation: “How did you get into that?”

Do you want to know a truth that’ll help you in any conversation? It’s this:

People LOVE to talk about themselves.
If you can get somebody talking about their lives and what they do, you have the start of a great conversation. That’s why this question works so well. It prompts a story the other person will be more than willing to share, and it allows you to pull out elements of the story to make a connection.

You could learn you had the same major in college or maybe you both worked with the same client at one point — then the conversation becomes natural and easy.

Question #3: “What’s been your favorite part about X?”

Variation: “I really like [X speaker, flowers, venue] today, did you have a favorite?”

Eliciting someone’s opinion — especially if it’s a strong one — is always a great way to establish a connection. This particular question can get really fun when you give an opposing answer.

I’ve seen this exact same conversation at events about speakers:

Person 1: Oh I really liked the first speaker.

Person 2: Really? I thought he was the least engaging.

Person 1: Fascinating! Why do you think that?

And the conversation just flowed from there.

Too often people think that conflict is a bad thing — it’s not!!! Conflict can be a bad thing, but it can also be an opportunity to learn a new perspective from the other person you’re speaking to. People can talk about their preferences all night!

Question #4: “Why would you say that?”

Variation: “Now I would have thought of X, but you said Y.”

The next time you make small talk with someone, take notice of how many vague statements they make about their industry/city/background/whatever.

Something like, “It’s a terrible industry to get into right now,” before moving on completely.

The next time you hear a statement like that, follow up with them on it. By asking for more details, you’ll show that you’re listening and are truly interested in what they have to say — thereby encouraging them to talk more.

Question #5: “What was the hardest part about X?”

Variation: “If you had to do X again, how would you do it differently?”

People love talking about overcoming adversity. Not only is it interesting to those listening but it’s also an instant connection when you involve emotion into the conversation.

This works well when you meet someone you admire — an author, speaker, or leader in your industry for instance. You can learn valuable lessons about something you’re trying to do.

Crafting your question toolbox

Of course, depending on the context of your conversation, you’re going to want to have different questions for different scenarios.

After all, I wouldn’t want to go into a mixer with high powered executives ready to ask, “Who would you rather walk in on while they were hooking up with someone — your son or your daughter?”

Alternately, I wouldn’t want to go out with someone and ask my date, “So what has been the most significant change in your industry since you started your career?”

That’s why you’re going to want to craft different meaty questions for different scenarios.

So the next time you’re making small talk, take note of great questions you hear and ask. Save them in your question toolbox for later.

Here are a few good sample questions to get you started:

Networking events/industry conventions

  1. What made you decide to do X?
  2. What are the biggest challenges when it comes to your industry?
  3. If you had to do X again, what would you do differently?
  4. As you gained more experience in X, what became more important and why?
  5. What would make today/this event successful for you?
  6. What still surprises you about X?


  1. What are your biggest goals right now?
  2. How do you spend your time?
  3. Playful questions like: Which do you like more — pancakes or waffles?
  4. What do you hate most about dating? (This question is both interesting and can help you avoid doing the thing they hate)
  5. What’s your favorite restaurant in the city? Why?
  6. Which Spotify playlist is the soundtrack to your life?

Baristas/Wait staff

  1. What’s your favorite thing on the menu? Why?
  2. What’s the craziest thing someone tried to order this week?
  3. Have you ever written somebody’s name wrong on purpose because you didn’t like them?

BONUS: If you really want to exercise your social muscle, check out my video on improving your social skills. It’s less than 30 minutes.

Can’t I just skip the small talk?
NO. Small talk is an important social lubricant

“But Ramit, I HATE small talk! Why can’t I just get straight to the point?”

Small talk is a CRITICAL part of life and building relationships — it’s what helps people get to know each other, establish meaningful connections, and lays down the foundation for great long-term relationships.

The term “small talk” is actually a complete misnomer because of its HUGE impact on forming relationships and developing unshakeable confidence. As such, it takes a lot more care and nuance than just getting right down to the point.

If you walked right up to a CEO you admired at a mixer or convention and said, “I REALLY LIKE YOU. GIVE ME A JOB, PLEASE!” how do you think she’d react? She probably wouldn’t give you that job.

But if you went in with some care, and drew her into an amazing conversation and THEN asked her for a job (or better yet just advice or a coffee meeting), she’d be a hell of a lot more susceptible to it.

The key is realizing that confidence and the ability to carry a good conversation are skills — and like any other skills they can be learned, honed, and mastered.

I used to feel uncomfortable and out of place during social events too — 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. avatar

    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. avatar

    “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. avatar

    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. avatar

    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.

  5. avatar
    Drew Wallace

    Super useful post – I'm going to try a few of these questions at a painful work event later this week.

  6. avatar

    Incredible Post!
    Thanks for taking the time to write on the topic.

  7. avatar


    I made a comment on this article when it was first posted and I spoke about how horrible my small talk skills were. I also mentioned that I would use this at my job since I work with the public on a regular basis to see what the results would be.

    Well, six plus months later, I can say it works! I have had full length conversations that were interesting, intriguing and down right exciting with people I never thought I could have.

    The majority of the patrons at my job are very to the point, don't bother me type of people who are very busy. Using these techniques, I was able to have them stop what they are doing and take the time to talk to me.

    Think about: Busy people who do not want to be bother took the time to have a conversation with me.

    Worked like magic!

    So much so, that I was the one that had to pull away from the conversation because they wouldn't leave me alone, lol.

    I never had that happened before. It was always people trying to get away from me!

    So, if this can work at my job it can work pretty much anywhere.

    Also, I'm going to start applying these techniques when dealing with clients and see what the results will be!

    I'm quite sure they'll be awesome.

    I guess I'll update ya in another six months.

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  9. avatar
    Jay Wilson

    Hey Ramit,
    Thanks for creating that video, it was really engaging – the time flew by! I noticed one thing in particular that really made me smile and think. During one of your stories where you described meeting with the CEOs ("radio buttons, not check boxes!") and you cut to how other people in the room were getting bored with your monotone… I noticed how you shifted the camera's perspective just a little, showing a bit more of the background above your head, and in that instance it really highlighted the point you were making – it was cool!

    I definitely have a few things that I want to improve on, I think the biggest one would be how to extricate myself from a conversation and then move on to another one. I can usually start a conversation, and I'm decently able to politely end it, but then I usually find my head is swimming from that first conversation so I end up pulling out my phone or finding a quiet window to just stare out of! I'd like to make the most of the time allotted to networking, but usually my introverted self just gets exhausted along the way.

    Anyone else have that problem?

    Thanks again for the video!