The Art of Meaningful Conversations

Three Types of Conversations

We’ve all had thousands of conversations, and we can have dozens a day. I’ve had conversations with people from all around the world who speak different languages and come from other cultures. I’ve found that there are three types of conversations.

The Optometrist

There’s the person who works in an optometry office who’s always talking about themselves and their accomplishments.

Unfortunately, in my experience, 70% of the human population are optometrists. Always talking about themselves, having zero awareness, and never ask other people any questions.

I’ve been on dates where the person speaks 100% about themselves, doesn’t even bother asking questions. I’ve really lost, excluded and fired many friends because of their lack of awareness.

The Airport Employee

The second type of conversation is the type that works at an airport.

They are almost constantly complaining about this, that, the football, the weather, never really talking with optimism, positivity, or possibility.

In this category, you have the condescending person who thinks that they know everything. Oh my god, it’s tiring.

But of course, there are people like that.

The Upward Spiral

The third type of conversation is the upward spiral conversation, where you’re architecting specific questions to get people to talk about their possibilities, their most exciting futures, and the things that make them come alive.

And this really is the best conversation to have because, as my friend Kyle Fussman said, the best questions in the world get the person asking the question and the person being asked the question interested in the answer. Why?

Because they often haven’t been asked those questions.

And when you ask them those questions, they have to look for those answers in their brains, and that gets them really excited because it’s getting them to explore new possibilities.

These people often ask to meet again and again because they are so enamoured by the idea of being inspired by a conversation.

What is the Caveat?

The caveat is that these people often don’t become interested in you. They walk away interested in what has come up for them, and they seek that out with you again.

But many people never actually wake up to the fact that they’re not returning the questions.

I’ve lost and fired a bunch of friends because of this absolute lack of awareness, of asking terrible questions, shallow interest, constant complaining, being right, and talking about themselves.

It’s such a bewildering thing. Wake up. Ask good questions. Be interested in the people around you.

How Can You Have More Meaningful Conversations?

Meaningful conversations only really come alive when there’s awareness, curiosity, and a genuine interest and authenticity in who’s sitting across from you.

When we ask sharper questions and practice the act of listening, we open up this whole space of possibility and inspiration, a doorway to deeper human connection.

Wake up, ask better questions and elevate the way you engage with the world.

FAQ: Mastering Meaningful Conversations

1. What are the three main types of conversations?

The three main types of conversations are:

• The Optometrist: People who only talk about themselves and their accomplishments

• The Airport Employee: People who are constantly complaining and negative

• The Upward Spiral: Conversations where you ask engaging questions to explore possibilities and inspire the other person

2. Why are upward spiral conversations the best?

Upward spiral conversations are the best because they:

• Get both people interested in the answers to the questions

• Encourage the other person to explore new possibilities and get excited

• Lead to deeper human connection through genuine curiosity and interest

3. What is the caveat with upward spiral conversations?

The caveat is that the other person may not reciprocate the interest and questions. They may remain focused on their own thoughts and experiences rather than engaging with you equally.

This lack of awareness and balanced exchange can be frustrating.

4. How can you have more meaningful conversations?

To have more meaningful conversations, you should:

• Practice active listening and ask thoughtful, open-ended questions

• Show genuine curiosity about the other person and their perspectives

• Avoid dominating the conversation or only talking about yourself

• Create an atmosphere of possibility, inspiration, and mutual understanding

Conclusion

Meaningful conversations are where real connection begins. When we become aware of how we show up, ask sharper questions, and actually listen, our interactions shift.

They expand our perspectives, deepen our relationships, and open up entirely new ways of seeing the world.

Note: This blog post is an adaptation of the transcript from the video below.