Ever find yourself secretly getting bored in the middle of a conversation?
Maybe even in moments where you and the other(s) do want to connect but it still feels dry, stuck, or just doesn’t go anywhere?
While it’s common to blame this on a cultural propensity for small talk (I used to), that’s not the reason.
It’s not that the majority of people prefer to stay stuck on the level of small talk.
It’s that none of us are directly taught how to transition to deeper connection, leaving us somewhat at the mercy of being in situations where (or meeting the people with whom) it just naturally happens.
But it doesn’t have to be that way.
When a conversation feels dull, it’s often not about compatibility.
It’s that the energy is stuck. The level you’re currently relating at doesn’t feel very alive or exciting anymore, but nobody is actively guiding it to a place that does.
The first step to learning to do that, is to understand which level of depth you’re currently at.
Think of it like using a map: If you don’t know where you are, you won’t know in which direction to go.
Here’s a framework I call “6 levels of Conversational Depth“.
Knowing which one you’re in can help you shift things, or stay where it feels most juicy for everyone involved.
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 speaking.
Communication is happening, but it does not communicate anything that reveals information about the people communicating.
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 also freeze the ice a few inches thicker. So it’s important to always be aware how the other person is responding.
To illustrate what the “ice freezing thicker” can look like: a guy once walked up to me in a bar, and the conversation went like this:
Guy: I like you, what’s your favorite soccer team?
Pep: Honestly, I’m not into football.
Guy: Which sports do you watch then?
Pep: Actually, I never watch any. I prefer to play instead of watching.
Guy: What about video games?
Pep: Don’t play them. My apologies for being a lousy conversationalist so far haha.
Guy: OK, we clearly have nothing in common. Cheers!
I’m sure that if one of us had moved the conversation to one of the other levels, we would’ve discovered that we have a lot in common.
All people have things in common. (and sometimes in the deeper levels, having less in common makes it easier to find things to talk about—because contrary to popular belief, connection doesn’t get sparked by commonalities).
But staying at this level after receiving uninterested responses made the conversation die out.
Now, to be fair, the guy was correct to move on. I was being an unfun and uncooperative conversational partner here.
I was not vibing. I gave him nothing to work with, no opening. I’m as responsible for making the conversation die.
But that’s how it goes. Out in the wild world of humans, you will meet people who aren’t vibing with your initial approach, and not attuning to that is a skill issue, not a compatability issue.
I could have taken initiative myself to steer the conversation to a deeper place. But I was there to have relaxed time-off, and helping people have deeper conversations is my job.
So what could this guy have done to steer the conversation to one of the deeper levels? And would could I have done, being on the receiving end of this?
From now on, each time we learn about a next level of conversational depth, I’ll give you clear examples how.
For now, let’s discuss why Level 1 (External Information) exists, and why I was wrong to demonize it in the past:
Meeting a new person is quite a crazy event, biologically.
We are a species that, for most of our history, lived in small bands or tribes. We had intimate knowledge of every other human in our environment.
Now imagine that one day, a new human appeared.
Who are they? Do they have our best interests in mind? Do they behave similarly to us in terms of values, culture and customs? Do they interpret our signals the same way? Is all of that real, or is it a manipulative ploy?
For nearly every human in history, getting this right meant life or death.
And even though it doesn’t anymore, the consequences are still real. Giving the wrong person intimate access to you can wreck your life.
Conversing at the level of external information gives people time to read each other’s nonverbal cues, allow their nervous systems to adjust to each other’s presence, and start a conversation without accidentally making ourselves more vulnerable than is good for us.
But that’s also the main risk with 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:
- People won’t have a reason to like you, remember you
- Our questions won’t invite others to share anything about themselves with us
- If people are uninterested or averse to the topic we brought up, disconnect can arise
(Side note: This is why going on a walk is a great first date idea. It gives you lots of external information to pull from in case you need some time to get comfortable with each other.)
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.
Beyond its seemingly casual nature, this level of conversation plays a significant role in social interactions and relationships.
- 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).
- 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. But having some information to mentally tag them with does create a degree of relationship.
- It can lay the groundwork for potential friendships.
- 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 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 slightly more superficial than it seems. And in many cases, can act as a mask. Its function of maintaining social cohesion can discourage people from revealing their true feelings or concerns:
One way that this level helps us create shared trust is that we can respond to small talk in the “right” way that shows that we understand the culture of the group and are attuned to it. (Basically that we are properly socialized and won’t pull any unexpected shenanigans.)
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 or outsiders.
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. And while skipping this level entirely is possible, it requires deeper attunement to the social context.
The best comparison I can give you is this: A Jazz musician can break all the rules precisely because they have mastered and transcended them. An inexperienced musician can break all the same rules and to most people, it will sound unpleasant.
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.
If this sounds like I’m totally overthinking something simple, try this experiment:
Next time your co-worker asks “How are the kids?” respond with “irresistibly sexy” and observe what happens😉
How to Make Better Small Talk
Here are some ways the nameless guy in the bar could’ve steered the conversation from Level 1 to Level 2.
Question:
Pep: Honestly, I’m not into football.
Guy: That’s cool, what are you excited about then? How do you like to spend your time?
Share:
Pep: Honestly, I’m not into football.
Guy: Oh, that’s too bad. It might be favorite thing to talk about. I grew up in (city) and it’s really part of our lifestyle there.
And here’s what I could’ve done to steer it there.
Question:
Guy: Which sports do you watch then?
Pep: None. I barely even watch TV. But I do love sports. I used to be a competitive judoka, and right now I’m learning gymnastics.
Share:
Guy: I like you, what’s your favorite soccer team?
Pep: None, for some reason the whole “pick a sports team” thing never made sense to my personality. But why don’t you tell me yours and why you picked it? Could be enriching for me to hear how that went for you.
Now, let’s go a bit deeper.
Level 3: Personal Stories
One a slightly more intimate level, we 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, or opinions we hold
- Sharing painful or dramatic experiences that shaped us
- Talking about how our day went, and what that means to us
Telling each other stories of our daily lives gives us a glimpse into each other’s psyche in a way that still feels comfortable and safe, because there is still a degree of distance: Instead of revealing ourselves directly, we reveal a narrative that helps others get an impression of us.
In between the lines of each story, we learn about each other’s opinions, values, motivations, memories, dreams, and aspirations for the future—all without the vulnerability of actually having the other person look straight inside our soul or how we feel in this very moment.
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.
So at this level, we’ll always be sharing a version of ourselves that is a narrative, rather than a “being”.
It’s not uncommon to never go deeper than this level, because most humans are hypnotized by our own self-image. Level 3 is how the majority of us relate to ourselves.
How to Move from Small Talk to Personal Topics
Here are some ways the nameless guy in the bar could’ve steered the conversation straight from Level 1 to Level 3.
Question:
Pep: Honestly, I’m not into football.
Guy: Interesting! It’s the most popular sport in the world. Any idea why it doesn’t move you?
Pep: Oh it’s not about football actually. It’s watching sports in general. On an intellectual level, I totally get why they are such a big thing in society. But for some reason, watching it doesn’t really grab me the way listening to music or watching a movie does.
Guy: What makes music and movies different for you? More of an artsy person than a sporty one?
Share:
Pep: Honestly, I’m not into football.
Guy: Haha alright. I often forget that not everyone is, because football really shaped me as a person. When I was growing up ____
And here’s what I could’ve done to steer it there.
Share:
Guy: I like you, what’s your favorite soccer team?
Pep: None. I don’t care much for watching sports. But now I’m curious, this being the first question you ask, I imagine it’s a big thing in your life?
Question:
Guy: I like you, what’s your favorite soccer team?
Pep: None. You know, it’s funny, these are the most normal questions to ask and I actually struggle answering them.. It’s like, to me the world is so full of unique and wonderful things. How could I ever pick favorites of anything?
On to level 4!
Level 4: Philosophizing
When we philosophize with another person, we are technically talking about external facts.
Which, as an attentive reader, might make you wonder why this is not level 1?
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.
The difference here is that we’re exploring the external world in a different way: Through questions, hypotheticals, meaning and interpretation.
This 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, despite being about external things:
- When philosophizing, we go on an exploration of reality together (instead of 1 person sharing stories and 1 person listening).
- 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.
In a sense, level 4 is the first level where we get to witness each other exactly as we are in that moment, which is why it can feel so special.
How to Go from Small Talk to Deeper Conversation
In general, transitioning straight from level 1 to 4 is a hit or miss. For some people it will feel awesome, for others awkward. And the more natural transition is to go through level 3 (personal stories) first.
Still, for the sake of example, here’s how the guy in the bar could’ve invited me there smoothly.
Share:
Pep: Honestly, I’m not into football.
Guy: Really? It’s possibly my favorite thing. I just love how it can bring people together. That surge of collective energy, it’s so powerful. You’ll see people that normally aren’t even friends hug each other tightly, jumping around, singing together. It’s magical to me. Have you ever experienced something like that?
Question:
Pep: Don’t play them. My apologies for being a lousy conversationalist so far haha.
Guy: Interesting. You describing yourself like that makes me think you have a pretty clear idea of what a good conversationalist would look like. How would you describe one?
And here’s how I could have done it.
Question:
Guy: OK, we clearly have nothing in common. Cheers!
Pep: Isn’t it funny that we seek for commonalities to connect, but then also claim opposites attract? Which one do you think is most true?
Share:
Guy: I like you, what’s your favorite soccer team?
Pep: You know. If I’m really honest with you, I spent a lot of my life judging sports fans. And I recently changed my mind. Do you wanna hear about it? Since you are into sports, I’d be so curious to hear your perspective?
Level 5: Emotional
Question time!
When you feel connected to somebody, how do you know it?
Where exactly do you experience that feeling?
For most people, the answer is somewhere in their body. 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 day.
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. Since the body is where we feel these feelings, it is also where we experience connection, friendship and love.
To add some nuance here: it’s not that 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. 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. Anyway, what’s your name?”
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.
One potent way to experience this level, you can also ask each other questions that point to your current feelings or sensations.
“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?”
If you’ve ever joined one of my workshops (or other Authentic Relating spaces) you may notice that many of the games and exercises we do are designed to stay in this level while expressing ourselves.
But of course, these are rather strange questions to ask in around the proverbial watercooler. So in daily life, it will look a bit different.
How to Pivot from Small Talk to Vulnerability
This is probably the easiest level to transition to, as long as you have the capacity to be with whatever happens in response.
If you want deeper conversations, getting really good at level 5 (and reading how people receive it when you invite them there) is the shortcut.
Here’s how guy-in-bar could’ve done it.
Share:
Pep: Don’t play them. My apologies for being a lousy conversationalist so far haha.
Guy: Apologies accepted. Not gonna lie, I do feel slightly bummed! I came in with kindness and high energy and the conversation deflated so quickly.
Question:
Pep: Don’t play them. My apologies for being a lousy conversationalist so far haha.
Guy: No biggie, we can’t always vibe with everyone and everything. I did notice you closing up there when I kept the small talk going. Curious what’s happening for you?
And here’s what I could’ve done.
Share:
Guy: What about video games?
Pep: Haha, I notice I’m about to give you a closed no again. You know what it is? A part of me assumes you want something from me, it’s a story I have a lot when meeting new people. So I’m feeling a bit defensive right now. Wanna start over and try again?
Question:
Guy: I like you, what’s your favorite soccer team?
Pep: I know the normal response would be to answer your question, but hey, why not, go to the part that really mattered! What did you feel towards me that made you exclaim to a stranger that you like 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, 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 I find myself having an even deeper admiration for who you are today.”
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 can 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, connective 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.
How to Lead Straight from Small Talk to Deep Connection
As with level 5, it’s fairly easy to transition to level 6 from any of the other levels, but it requires a certain depth of presence, both with yourself and to track how the other people are feeling. It’s not uncommon for people to have never experienced this before they try a “formal” connection practice like Circling or Authentic Relating.
Still, in many situations, you can safely invite people to this level without it getting awkward. Just be aware that you are amping up the intimacy by a lot, and not everyone will want to go there with you.
Here’s what guy in bar could’ve done:
Pep: Don’t play them. My apologies for being a lousy conversationalist so far haha.
Guy: I’m relieved to hear you say that. You know, it took some courage for me to come and talk to you. And before you said this, I was worrying I was doing something wrong. Wondering how it feels for you to hear that?
Here’s what I could have done:
Guy: What about video games?
Pep: Truth is, there’s a part that sees small talk as effort and wants to skip it. So I notice I’m turning your questions down, but what’s really happening is I’m just tired. There’s also a part of me that’s really proud of you for talking to a stranger and not giving up easily. How about we cheers to that?
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 the levels 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 exploriment of sticking only to one particular level.)
Once you become fluent at each of these 6 levels of conversational depth, you can use them to unstuck stale conversations. But deeper isn’t always better—and going too deep too fast can sometimes create disconnect. Small talk is social lubricant for a reason.
So how do you decide how deep to go?
The first thing you can play with is simply adjusting your own communication style to the desired level.
As strange as this may sound: Don’t assume you know what your desired level is. Actually check in with yourself:
I generally 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 nudge the conversation to a more shallow level, too.
Once you made an invitation to a certain level, observe how the other person responds. Do they follow you there? Do they react as if it felt a bit sudden?
This will help you calibrate your depth depending on what serves the conversation most.
If calibration doesn’t come natural to you, it can be useful to lead with sharing rather than lead with questioning.
Why?
Because you taking the lead with revealing more of yourself can show the other person it’s okay to do so. Whereas for some people, an unexpectedly deep question can feel quite invasive. In a sense, it’s asking them to lead with going deeper.
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.
People will rarely tell you this directly (since that in itself is already a Level 6 response), so the most important skill for deepening a conversation is to slow down and pay attention to the other person’s (nonverbal) responses.
This way you’ll be able to lead it to the exact place that feels most alive.
Usually that’s somewhere right on the edge of what feels comfortable and what feels new or unexplored.
Lastly, worth noting that each level has a clear function, and some contexts create limitations on which levels suit it:
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.
And if you are in a place where 100 people can hear you, you might not want to move to Level 5 or 6, because you’re effectively revealing yourselves to all those people, not just each other.
Think of conversations like a dance. Swinging between deep and shallow. Resonance and dissonance. Tension and release Hide and seek. Seeing and being seen. Leading and following. Blurring and dissolving the lines between. Disconnecting and catching each other again.
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. And if you’re not aware of the room, you’ll step on random people’s feet.
And as a final note:
This skill is best learned through direct experience, not analysis.
Everything mentioned so far is part of our core curriculum in The Connection Dojo, an online training space where we practice all of this (and many other things) live.
If you’re curious to hear more about it, just send me an email or DM, and I’ll send you a doc with all the info on how to join.
Much love,
Pep