Use These 10 Deep Questions To Really Get To Know Someone

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 connects 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 5 questions you can ask someone that leads to deep conversations. Before we get to those 5 questions, there’s 3 important principles we need to understand first.

Related: 9 Big Questions To Make Your Brain Hurt (In A Good Way)

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.

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 judgement 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?”

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 5 questions you need to ask for deep conversations

Now that we’ve covered those 3 important principles, here are 10 questions we can ask that leads to deeper conversations.

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 that 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 they 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.

Related: 4 Signs You Love Someone Who Doesn’t Deserve You

6) Who is your personal hero?

This question says a lot about 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. If they don’t have a story, don’t worry. Ask one of the other 9 questions!

Looking to reduce stress and live a calmer, more focused life? Mindfulness is the easy way to gently let go of stress and be in the moment. It has fast become the slow way to manage the modern world – without chanting mantras or finding hours of special time to meditate.

Source: Hack Spirit

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