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How to Have Deeper Conversations: Mastering the 6 Levels of Conversational Depth

  • 15 min read

Do you ever find yourself secretly getting bored in the middle of a conversation?

How about moments when you like someone and you want to connect more deeply with them…but it just doesn’t happen?

What if there was a way to create deeper, more connective conversations with the people you meet?

As you might expect, this blog post will teach you exactly that.

The first step to taking any conversation to a deeper level, is to understand which level it is currently at.  (Think of it like using a map: If you don’t know where you are, there’s no way to navigate to somewhere else.)

Roughly speaking, there are 6 different levels of conversational depth. So let’s begin by getting to know them:

Level 1: External Information

This is the level many people find themselves in when they are in a new group, still figuring out who they might like (or who might like them).

Typical topics are: News, sports, entertainment, celebrities, politics, and of course everyone’s favorite: The weather.

At this level, all conversation focuses exclusively on things that have nothing to do with the people who are talking.  

Still, that doesn’t make it impossible for such communication to spark a connection.  When someone brings up a topic that deeply excites me, but few other people care about, I definitely feel some connection with that person.

A good thing about a conversation at this level is that it can sometimes help break the ice.  But be warned: in other cases, it can actually freeze the ice a few inches thicker.  So it’s important to always be aware how the other person is responding.

For example, a guy once walked up to me in a bar, and the conversation went like this:

I like you, what’s your favorite soccer team?

Honestly, I’m not into football.

Which sports do you watch then?

Actually, I never watch any. I prefer to play instead of watching.

What about video games?

Don’t play them. My apologies for being a lousy conversationalist so far haha.

“OK, we clearly have nothing in common.  Cheers!”

I’m sure that if he had moved the conversation to one of the other levels, we would’ve discovered that we have a lot in common.  All people do (and sometimes in the deeper levels, having less in common makes it easier to find things to talk about).

But staying at this level after receiving uninterested responses made the conversation die out.  Sure, I could have taken initiative myself to steer the conversation to a deeper place. But at this point, I didn’t know yet whether I’d be interested in hanging out with this person or not.

And that’s the main risk of this level of conversation.  If you stay in it just a little too long, things can fizzle out quickly.

Because when you communicate in this way, you’re sharing nothing about yourselves with each other.

As a result:

  1. People won’t have a reason to like you or be interested in you
  2. People won’t have a chance to talk about themselves to you
  3. A disconnect can arise if people dislike the external topic you bring up (or find it uninteresting)

Level 2: Personal Information

This is the level of most small talk , networking and watercooler conversations.

Communication at this level is still centered around facts and information, but it’s information about the actual people talking.

Questions like, “What do you do for work?”  “How are the kids?” and “Got any cool plans for the summer?” all belong at this level.

I used to have a strong dislike for this type of communication (see the first post ever published on this blog). But since then, I’ve come to see the value of it. In fact, I’ve even started to enjoy it!

Beyond its seemingly casual nature, this level of conversation plays a significant role in social interactions and relationships.

  1. It acts as an icebreaker in new social settings, reducing awkwardness and enabling strangers to initiate contact (much more effectively than level 1, which sometimes creates the awkwardness).
  2. It contributes to social cohesion and creating community.  We simply don’t have the time or desire to go super deep with every single person we meet.
  3. It can lay the groundwork for potential friendships. 
  4. It helps us gauge appropriate topics without making ourselves vulnerable or accidentally breaking some taboo in a new peer group. (Breaking taboos is great once a connection is established.  If you do it before that point, some groups may react by ostracizing you in subtle or not so subtle ways.)

That said, for all its benefits, the problem that made me initially dislike this level of communication still hold true:

One of the ways small talk promotes social cohesion, is that it’s actually a form of ritual in which certain answers are culturally acceptable and others are not (“culturally” not being limited to your country but also the culture of your workplace, friend group, local church etc.).

This makes it often superficial and in some cases, can act as a mask. Preventing people from revealing their true feelings or concerns.

Responding to small talk in the “right” way shows that we understand the culture of the group, creating a sense of shared trust. Naturally, this also causes such conversation to exclude people who aren’t familiar with the cultural norms on the topics being discussed. As they will respond in ways that make others see them as “weird”.

I suspect that it was evolutionary beneficial at some point. For example, it’s a good defense mechanism against secret invaders from a hostile group.

When gathering around a 21st century watercooler, you’re obviously not worrying that the person in front of you is secretly a spy from another company (assuming it’s not the CIA’s watercooler we’re talking about). But your small talk will still follow the same “inclusion-exclusion” principles.

If this sounds like I’m totally overthinking something very simple, try this experiment:

Next time your co-worker asks “How are the kids?” respond with “irresistibly sexy” and observe what happens😉

Like alcohol, small talk is a great social lubricant when used in moderation. And like alcohol, it’s good to pay attention to whether it’s making things better or worse. Striking a balance between this level and the deeper ones can help you build more meaningful connections, while still blending in with social norms.

Level 3: Personal Stories

One a slightly more intimate level, we can tell each other stories about our lives and emotions.

This is the level of asking “How have you been?” and actually expecting an answer other than just “good, you?”.  And it’s the level of many drinking games, like “Never Have I Ever” or “Truth or Dare”.

Examples of communication at this level are:

  • Stories of things we did in our life and how we felt doing them
  • Sharing painful or dramatic experiences that shaped us
  • Talking about how our day went, and how we feel about it

Telling each other stories of our daily lives gives us a glimpse into each other’s psyche in a way that feels comfortable and safe.  In between the lines of each story, we learn about each other’s our inner opinions, values, motivations, memories, dreams, and aspirations for the future. All without the vulnerability of actually having the other person look into us, as the focus of the conversation goes to the story.

The more time we spend talking to someone at this level, the more we get the sense that we know them. That’s why such conversations are often the beginning of a friendship.

As with the previous levels, the same things that makes this level of conversational depth feel safe, are the things that stop it from going deeper:

Listening to our stories feels like getting to know each other, but what we’re actually getting to know is each other’s self-image. All our stories are about the past or future. And of course they are filtered through our own interpretation of those moments, as well as our preferences for how we want to be perceived by ourselves and others.  So at this level, we’ll always be sharing a version of ourselves that is close to who we are, but no cigar.

One way to connect on a level that has way less of this filtering, is to share with each other in real time.  

Level 4: Philosophizing

When we philosophize with each other, we are often talking about external facts.   Which, as an attentive reader, might make you think it’s a level 1 conversation.  

Still, you just know you’ve had a deep conversation when you stayed up all night taking about the meaning of life, the universe and why the hell the word “lisp” has an ‘s’ in it.  (Even though none of those things have anything to do with you.)

So even though it focuses on external things, this is the level most people talk about when they mention having had a “deep conversation”.

The are 2 main reasons we experience such talks as more deep and connective:

  1. When philosophizing, we go on an exploration of reality together (instead of 1 person sharing stories and 1 person listening).
  2. We are revealing the content of our mind with each other in real time.  No more reading between the lines, we get to see each other exactly as we think in that moment.

Both of these things can be especially nourishing for people, as they are not that common in daily interactions.  And this can create an intimate mental connection between the people involved.

Level 5: Emotional

Question time!

When you feel connected to somebody, how do you know it?

Where do you experience that feeling?

For most people, the answer is somewhere in their body.  Most usually the heart (although I bet you’ve felt it in other fun places before). 

That is why when we experience conflict or disconnect with someone, we say that we need to have a “heart to heart” conversation with them.  No one ever said “let’s have a mind to mind”. Because well, we’re already having those all the time.

Western culture is extremely mind-centered, and as a result, not very body-centered. But as we’ve established, we do not feel with our mind.  We feel with our body.  So as a result of not being very aware of that body, most of our feelings are hidden from other people (and even ourselves) in our day to day life.

Since the body is where we feel these feelings, it is also where we experience connection, friendship and love.  Because of this, talking about feelings can get us to deeper levels of connection than talking about thoughts.

It’s not like in Western culture, we never try to talk about feelings. But when we do, we usually end up doing so by talking about the thoughts we have about those feelings. “I have been depressed lately”, “I’m stressed because of work” or “I wish wasn’t so tired” are all examples of this.

True emotional communication happens when we share what we are actually feeling and experiencing in this moment without creating stories about it

A great example of this would be walking up to a stranger and saying:

“I’m a little bit nervous right now. Because I have no idea what to say to start this conversation or keep it going. But I saw you across the room and immediately felt a strong attraction to you. So I decided to just come up, see what happens and hope I don’t make a fool of myself.”

To steer the conversation towards this level, you can also ask questions that invite the other person to share their current emotions:

“What’s it like to be you right now?”

“When you’re recounting that story, what does it do for you in this moment?”

“I notice your lips curled up when you were speaking, what’s happening there?”

As simple as this sounds, where at the previous level, we were revealing the contents of our mind, now we reveal what’s going in our body and soul. And this can feel extremely vulnerable and connective for people who haven’t tried it.

The two requirements for creating connection at this level of conversation are vulnerability and curiosity. (This is where not having much in common is an advantage.  When the other person is very different, their experiences may be too.  So it’s very easy to be curious about them.)

After all, intimacy is about truly seeing each other (as the love guru would say “Intimacy is into-me-I-see”). 

Without vulnerability, the other person doesn’t get to see you.  And without curiosity, you don’t get to see them.

Level 6: Relational

The final level is “relational communication”.  Where both of us share how we feel and what we notice in this moment, in relationship to each other.

In essence, this is not that different from the previous level. Except that this time, instead of just revealing ourselves, we are revealing the connection between us and how it evolves. For example:

“When you were telling that story. I started to feel a little sad myself, and now that feeling gives way for a sense of caring for you. It deeply impacts me to imagine you at such a young age having to go through that. And it makes me appreciate even more the person you grew up to be.”

A question to elicit a response like this could be:

“While I’m saying this to you, I notice you start breathing faster and your pupils are dilating. What’s happening for you now?”

An ongoing conversation at this level, looks a bit like this:

I tell you what it feels like to be with you right now.

-You tell me how it feels to hear those words.

I tell you how your reaction has impacted me.

-You tell me how you noticed a change in the energy in the room after I said that.

I thank you for noticing it. Because I hadn’t notice the change, and I’m enjoying it now.

(and so on and so on).

This same type of interaction could happen between 3 people, 4 people, or an entire group.  And when you add more people to the mix, some of the emotions arising can get spicy quite quickly (conflict, attraction, unexpected triggers,…). But when you stay at this level, even situations of conflict can lead to extremely deep, connecting moments.

In fact, if everyone involved continues to communicate at this level for a while, you can get into some kind of odd conversational trance which is a truly unique experience. Compared to talking about the weather, we’re far from the shallows now

Relational communication, as simple as it is in concept, can create profound levels of connection, of the kind that you usually only experience by rare chance.

When we both open up about how it feels to be relating to the person in front of us, it fulfills a deep need to be seen and heard.  A yearning that is very real for most people, but in itself, often isn’t seen or heard by us.

Putting It All Together

Now that you are familiar with each level of conversational depth, the first thing you can do is identify which of them you rarely spend time in.

Do you avoid small talk (level 2)?

Do you have a hard time sharing your emotions with people (level 5)?

Then I invite you to deliberately spend some more time at those levels for the next few weeks. Get a feel for them, until they come naturally. (If you’re adventurous, you may even do a 30 day experiment of sticking only to one particular level.)

Once you’re used to all of them, you can navigate any conversation in any direction you want. To do so, simply adjust your own communication style to the desired level.  Whether it’s asking questions that elicit different responses, or sharing things about yourself in a different way.

From the way I write this post, you may think that I believe the deeper levels are superior forms of conversation.  But that isn’t necessarily the case.  For example, if you want to work together with someone in an efficient way, philosophizing is a terrible way of communicating.  But sticking to simple, level 1 communication works wonders.

I often favor depth in conversation.  But there are also moments when I prefer not to have any interaction at all (call it “level 0” 😉 ).  If you find yourself in such a moment, you can use this same knowledge to steer the conversation to a more shallow level.  

And of course, you have to take into account the other people involved. Just because you want to go deeper, doesn’t mean that that’s what the other person desires in that moment.  Some people need some time to get in the mood. Or may not be interested in connecting with you at that time at all. 

The most important skill for deepening conversations, is to slow down and pay attention to the other person’s (nonverbal) responses.  This way you’ll be able to lead it to deeper places at a time which is appropriate for both of you.

Think of conversations like a dance.  You can step in and out of the different levels in any direction, and lead the person towards what you would find most nourishing or fun in that moment.  But if you don’t sync with their vibe and pace, it’s not going to be a very enjoyable interaction.   

Next time you are with people, play around with this. Move to one of the deeper levels, see what happens.  And let me know how it went!

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