12 Ways to Make Intellectual Conversation

I LOVE intellectual conversations.

When I moved to a new town and didn’t know anyone, I was starved on them. I just got stuck in small talk with people I didn’t know well.

That forced me to learn to be really good at getting past the chit-chat and making intellectual conversation.

1. You can’t make intellectual conversation with everyone

Some people just aren’t interested in intellectual conversations. Only some of those you come across in life will be.

This guide is about how to figure out who is, and get past the shallow small talk with them so you can transition into more intellectual conversation.

I’ll also talk about where to find these people in the first place.

Let’s get to it!

2. How to figure out if you have mutual interests to base the intellectual conversation on

Okay so here’s the number 1 mistake I did: I didn’t ask the right questions.

You want to ask questions that help you figure out what someone might be interested in. When you do, you can find mutual interests to make deeper, more substantial and intellectual conversation.

You can’t make intellectual conversation before you’ve found mutual interests.

So, I learned to ask 3 specific questions to figure out mutual interests:

  • What do/did you study?
  • What do you do? (Or, do you want to work with after school)
  • What do you do in your free time?*

These questions are so powerful because they help you know what someone might be interested in.

(Don’t fire these questions off in a row, but ask them when it feels natural.)

*The most powerful question here is number 3: What they do on their free time. It represents people’s interests better than their jobs and studies, but all 3 help paint picture.

You can now make assumptions and see what sticks…

3. Make assumptions and see what sticks

So now, you asked the questions in the example above and have a better picture of the person.

Let’s say that someone…

  1. Studied history
  2. Works as a book editor
  3. Likes to read on their free-time

…you can match that with your interests. Read any author you think they might like? Any history events you are interested in?

Bring up things that you assume the person might be interested in based on their answers.

Some things stick (The person gets engaged or talkative) or it doesn’t stick (The person doesn’t react) and then I see if something else sticks a bit later.

So in the case of the book editor, I would do the following to move toward interesting conversation:

  • I would mention the book Sapiens I read a summary of the other day, and see if they’ve read it
  • I would ask what books they’re reading, to see if I’ve read any of them
  • I’d ask what kind of history they’re the most interested in, and see if we have overlap of interests there
  • I’d ask more about their job as a book editor to figure out what genre they’re in.

Another example. Let’s say that someone…

  1. Studied computer science
  2. Works as a programmer
  3. Likes to game on their free time

I don’t know how to code and I don’t game. But I can make assumptions about other things someone who’s interested in code might also be into.

Then this is what I’d do:

  • I’m fascinated by predictions about the future, so I’d ask how they think technology will change the world the coming years
  • I’d talk about self-driving cars and autonomous robots
  • I’d see if they’re interested in the concept of the singularity.

See how you can make assumptions about what someone might be interested in, even if you DON’T have the same interests at first glance?

4. Know where to find people who share your interests

To meet people who were more interested in intellectual conversation, I looked to join a philosophy club. Unfortunately, there were none in my town, so I started my own.

I posted on Facebook and Meetup, and made it a weekly event. For everyone who attended, I asked if they had friends they thought could be interested.

But you don’t need to create a group of your own. Just browse Meetup and Facebook groups and see what you might be interested in.

The key is this: Find out where the people are who share your interests. They’re also likely to share your personality.

5. DON’T write people off too soon

Go into the conversation with an open mind. (This is the most important piece of advice you will find on here.)

I don’t know how many friendships I’ve missed out off because I wrote the person off too soon.

Not everyone wants to make intellectual conversation. But you need to scout for similarities thoroughly before you can even know.

I’ve been surprised many times by the amazing conversations I’ve had with people who I’d first written off based on the first few minutes of interaction. After I asked some probing questions, it turned out that we had a lot of interesting topics to talk about.

6. To make intellectual conversation, dare to open up to be able

The flip side of not judging a book by it’s cover is not judging your own book harshly. You are the author of your own story, and thus you are the most critical on yourself. Everyone has something to offer. That’s including you of course.

This means that you need to dare to open up about yourself and your interests:

For others to feel comfortable opening up to you about what they’re interested in, you want to share a little bit about yourself between your questions.

Many who may be viewed as being boring aren’t actually boring. They just don’t know how to open up during conversations.

7. Don’t steer the conversation too much

So in the beginning of this article, I talked about how to move the conversation toward more intellectual topics.

That’s needed to get past the small talk. But at the same time, you need to be adaptable and move with the conversation.

There is no need to research an extensive topic prior to talking about it and try to stick to it. This isn’t school, and you aren’t giving a dissertation on the subject.

If the conversation moves towards something you don’t know much about, be honest. It’s okay to mention that you don’t know much about the topic.

8. Be OK with being a student

If the conversation goes somewhere that feels uncomfortable to you, ask yourself, why? Often, we get uncomfortable when we end up on a topic we don’t know much about and try to steer the conversation back into what we master.

Dare to keep going. Be open with what you don’t know, and ask sincere questions to learn about it. Be OK with letting someone explain to you a topic you don’t know anything about.

Later in the conversation, you might end up on your territory, and you’ll be able to teach them.

9. Be on the lookout for the hidden core of the subject

If your conversation revolves around the take-out food you ordered after your boyfriend broke up with you, ask yourself this, why are you talking about the food?

Use critical thinking to navigate towards the heart of the matter. In this example, the heart is clearly the breakup!

From there you can share your more personal thoughts like:

  • What happens to a person (you) after a breakup?
  • When does it become a growing experience?
  • What does it mean to be single now?

Be on the lookout for the hidden core.

10. Ask these “go deeper”- questions to turn shallow conversation interesting

In the same way that you must learn to navigate your own thoughts and speech away from the surface, you can also edit nearly any conversation you have with another person to be more interesting.

By being an active listener, you can pick up on when people say something that clearly has deeper meaning within it, and gravitate your questions towards that topic.

Some questions that often take conversations to the next level are:

  • Why do you think that is?
  • How does that make you feel?
  • How do you mean when you say [what they said]?

Don’t be afraid to pinpoint exactly what it was you heard in the conversation that struck you and asks the person to elaborate on it. Ultimately, we humans want to talk about ourselves, and it’s likely if you try to circle back to something more personal it will be met with a positive reaction.

Read more: How to have deep and meaningful conversations.

11. Create mini stories

The most interesting conversations take place when we are discussing a topic we’re interested in, but we’re also taking the initiative to insert our own feelings into the dialogue. Feelings aren’t opinions. Opinions are easy to share. Feelings stem from our personal stories, and that touch of personality adds layers to the facts and opinions we do choose to share with our conversation partner.

For example, if you are fascinated in American politics, rather than spewing facts about the latest news update you could intertwine the fact, your opinion on the fact, and explain why you feel that way.

This makes for a mini-story in a sense, and now your conversation partner has more information to pull from and move with as your time together unfolds.

12. Explain. Don’t Insist

When we insist on an experience we had, the feelings we felt because of it, we are limiting the way a conversation can unfold. While it’s certainly fine to say, “The traffic today was awful. I was mad!” It is a better conversation if you explain why you were mad. For example, “I’ve had so much on my mind lately, sitting in traffic was an angering experience. I felt like I was stewing with my thoughts.”

This sentence allows the person your speaking with to ask to follow up questions. They are also going to be interested because there is a bit of YOU in there. We don’t want to hear about traffic any more than we have to. But when the traffic story entails emotions that are explained, it opens up room for so much more to take place.

Remember, to make intellectual conversation is about coming from topics of interest.

8 years ago, I committed to build my social confidence and become great at connecting with people.

Hundreds of books and thousands of interactions later, I'm ready to share with the world what I’ve learned.

The interest in my findings has been beyond my dreams. We now have 30 000 members taking our courses. Perhaps you’ve seen my writing in magazines like Business Insider and Lifehacker.

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