Use these 15 deep questions to get to know someone well

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It’s no secret that introverts hate small talk. It’s superficial, meaningless and quite frankly, a waste of time.

An introvert doesn’t care what you think about the weather. They want to know more. They want to dive deep and know your purpose, your values and why you get up in the morning.

And as it turns out, introverts are onto something.

Research has found that meaningful conversation is actually good for us. A recent study, published in the Journal Psychological Science, involved college students who wore an electronically activated recorder with a microphone on their shirt collar that captured 30-second snippets of conversations every 12.5 minutes for 4 days.

This created a “conversational diary” of their day. The researchers then went through the recordings and categorized them as small talk or more substantive conversations. They also looked at how subjectively happy each person was.

The results? The happiest person in the study had twice as many substantive conversations, and only one-third the amount of small talk, as the unhappiest person.

In the New York Times, the lead researcher of the study, Matthias Mehl, discussed how human beings – both introvert and extrovert – are social animals who have a need to connect with others, and meaningful conversations connect more than small talk does.

So the question is, how can you skip the small talk and engineer more meaningful conversations?

We’ve come up with 15 deep questions you can ask to get to know someone.

But before we get to those 15 questions to get to know someone deeply, there are 3 important principles we need to understand first:

Principle 1: Welcome the silence

We get uncomfortable when we experience silence. Even if we’re truly listening and engaged in the conversation, we feel the need to avoid silence at all costs.

However, silence makes us panic and fill the gap with empty words.

Instead of seeing silence as a bad thing, allow it to linger and let the conversation flow naturally.

The more silence occurs, you more you’ll become comfortable with it.

You’ll be able to stop and think about what is actually being said and give yourself time to come up with a meaningful response.

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2) Don’t assume

We’re all guilty of this. When we listen to people, we come up with preconceived conclusions in our head. We use our past experiences and stereotypes so we can understand things better. It’s normal, but be careful.

Don’t let your own brain’s judgment cloud reality. If you’re trying to understand where someone is coming from, don’t try and change what they mean by saying things like, “Oh you mean you prefer doing it this way.”

Instead, ask questions like, “now wait, explain that to me again. How do you exactly prefer doing it?”

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3) Stop thinking about what you’re going to say next

We hate silence, so most of us prepare what we’re going to say when someone stops talking. But this causes us to not really listen to what someone is saying.

The conversation doesn’t flow correctly and their message is lost. Next time, every time you notice yourself preparing your answer, just let it go and focus on what they’re saying.

You might come back to it, or you might let the conversation flow in a totally new and fun direction.

The 15 questions you need to ask to get to know someone deeply

Now that we’ve covered those 3 important principles, here are 15 questions to really get to know someone.

1) What’s your story?

This is a great starting question that can inspire a meaningful answer.

Some people will have an immediate, awesome response to this question that can lead you down many paths.

Others will need a helping hand. If someone isn’t open to answering the question, you can ask them further questions like, “what has your life been like until this point?”

2) What are you passionate about?

One of the quickest ways to talk about something interesting.

The person answering will usually be excited and you’ll get to see them unleash their true energy.

If you feel the passion with them, you’re well on your way to being involved in a deep conversation.

3) If I really knew you, what would I know about you?

An open-ended question allows the person to go as deep as they want.

This can produce some sincere and in-depth questions, so be prepared to listen, understand and make them feel heard.

4) What in your life currently makes you feel the most fulfilled?

This is a great question that gets people thinking about what really makes them feel happy. A great positive energy booster for any conversation.

People open up about things that make them feel good, so it can lead to some deep conversations.

5) How would you describe yourself?

This question might seem like nothing special in particular, but its ambiguous nature will reveal a lot about their personality.


Because you can answer this question in different ways. They might talk about their personality, their job, their family.

Whatever the answer will generally show their priorities in life.

This can give you insight into what’s important to them, and by probing a little further, you can get them talking about what they really want to talk about.

6) Who is your personal hero?

This question says a lot about a person.

Some will describe a family member, others will describe an athlete or a pop culture celebrity.

Dig deeper and really get to know why they selected who they did. What traits about this person do they admire?

You’ll learn a lot about their values. Usually, they’ll mention traits or characteristics that they aspire to have in themselves.

7) What is your dream job?

An ambiguous question that will reveal a lot. Some will mention creative pursuits. Others will mention jobs that earn a lot of money.

And some who like to have a laugh and use their imagination will describe jobs that don’t exist like “beer taster or “puppy cuddler”.

Whatever they respond with, it will reveal what they desire in the future and whether they’ve thought about before or not.

8) Have you read any good books?

This is an excellent question and the answers will vary wildly.

It’s another great way to get to know what someone is passionate about.

Some people will be honest and say “they don’t read”. But if they take time to search for an answer, it might mean they’re trying to impress you.

9) What is your biggest accomplishment?

This will give you critical insight into a person’s past and will get them talking about something that is meaningful to them.

Again, a great way to get someone to open up and speak with passion about themselves.

10) What’s a story of yours that you don’t get to tell often enough?

This can really get someone talking if they’ve got a story they’re itching to tell. People loved being listened to, so keep your ears open and this question will break the ice like you wouldn’t believe.

If they don’t have a story to tell, then don’t worry. Simply ask one of the other 14 questions!

11) What is your ultimate goal in life? 

This is another ambiguous question that will reveal a lot about what their priorities are in life.

Do they mention a self-serving goal? Or do they have a mission that’s about other people and higher than themselves?

Either one is fine, but you’ll begin to see whether they’re really a person you would like to include in your inner circle for the long haul.

Keep in mind that you might need to probe a bit to really get the answer out of them, but once you do, they’ll speak with such passion and authority that they’ll begin to reveal who they really are.

12) What are you most afraid of? 

This question can take a dark turn, so be careful. But everybody is afraid of something, so it can really get the conversation ticking.

Once you get them to fully explain why they’re scared of something, you’ll probably begin to understand why it really is frightening.

This can build empathy and comfort which are two important traits for a deep conversation.

13) What’s the best approach to solving a conflict? 

An interesting question that will reveal a lot about how they approach difficult situations.

Are they a direct kind of person? Do they believe that honesty is the best policy? Or do they believe in keeping the peace and resolving issues in a positive manner?

Depending on which way you bend, you’ll start to see if this is the type of person you really want to spend time with.

14) What’s the best way to earn somebody’s respect?

An eye-opening question that explains what they actually value in themselves and others. Do they admire kindness? Or do they give their respect to work hard?

There are lots of different ways to answer this question, so probe them further and ask why kindness or work ethic (whatever it may be) is their number one indicator of respect.

15) Which is more important: what you say or how you say it? Explain your answer.

A great question to see if this is the kind of person you could develop a significant relationship with.


Because you’ll understand whether they value appearance and beauty above the practical results of actions.

Now don’t get more wrong, I’m not saying either one is worse than the other, but you will start to see whether you two will truly get long.

In conclusion

They’re all great questions to ask, but keep in mind that they do require some probing to get the true answer out of them.

Once you’re able to get them to speak their piece, these questions will reveal whether they really are someone you’d like to spend more time with.

Also, remember that they’ll probably ask you the same questions, so make sure you have some prepared answers that will wow them!

You may also like reading:

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Lachlan Brown

I’m Lachlan Brown, the founder, and editor of Hack Spirit. I love writing practical articles that help others live a mindful and better life. I have a graduate degree in Psychology and I’ve spent the last 15 years reading and studying all I can about human psychology and practical ways to hack our mindsets. Check out my latest book on the Hidden Secrets of Buddhism and How it Saved My Life. If you want to get in touch with me, hit me up on Facebook or Twitter.

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