A man and a woman talking in front of a window

Move Past the Surface and Create Depth in Your Conversations

Struggling to move past surface level conversation? Do you find small talk to be uncomfortable?


Even pointless?

For some, it is a way to make connections, launch into meaningful conversations, and feel more at home with the people around them. But for many, small talk feels like an awkward experience that leaves them feeling drained rather than energized.

But it doesn’t have to be that way!

In this blog post, we will explore different ways you can move past the surface and create depth in your conversations!

A white coffee mug with the word Conversations printed on it
You can take the coffee out of conversations, but you can’t take the… wait, what?

The Myth About Small Talk

The biggest myth about small talk is that it’s binary—you’re either making small talk or you’re in a deep conversation.

But that’s not true.

For every honest conversation we have, we want to poke around with basic questions to get an idea for topics you and the other person would find interesting enough to have in-depth discussions.

It’s true that you will occasionally find people who are willing to jump right into deep conversations, but they are exceptions to the rule. Most people want to trust you before moving in a deeper direction.

So how do you poke around and find those nuggets of depth worth pursuing?

A dog running through the woods at the camera
Nugget found a nugget!

Lateral Questions vs Vertical Questions

A lateral question is like casting a fishing pole in a specific area of a lake. You’ll get a bite in some areas and nothing in other areas—maybe even awkward silence.

And that’s ok!

Such is the art of interacting with our fellow humans.

Examples of lateral questions might include many we’re familiar with:

  • What do you do for work?
  • Where are you from?
  • What kind of music do you listen to?
  • What are you doing this weekend?

When you do get a bite with a lateral question, that’s when you ask a vertical question.

Vertical questions allow us to turn small talk into a deep conversation.

In other words, lateral questions stay on the surface of the lake while vertical questions dive below it and can be considered deep conversation starters.

A man about to remove the hook from the mouth of a fish
Woah, look at that deep conversation Jimmy just caught!

What Does This Look Like in an Interesting Conversation

Sam: So, what do you do for work?

Alex: Eh—I’m just a student.

Sam: Oh, are you from around here?

Alex: No, I grew up in Virginia.

Sam: Virginia seems like such an idyllic place to grow up, plus you get to experience all four seasons—what made you want to go to school here?

Alex: I’ve always wanted to live on the west coast! The weather is great, the people are chill, and—WOW—the food out here is just fantastic!

DING DING DING! Check out the enthusiasm in Alex’s response to this question. And note the emphasis on the food part of her answer. Time to dive in and ask something slightly personal.

Sam: You’re not wrong! There’s this little place called Salsa and Beer on Lankershim and they have the best Mexican food I’ve had out here. What’s your favorite spot so far?

Alex: Oh my God! It’s so hard to pick just one! Back home, I couldn’t imagine being able to walk out of my apartment and have a dozen healthy options within a couple blocks. But I will say I have some favorites depending on whether I’m leaving the gym or…

Alex is going to talk for a while, so let’s move on to the next critical component of effective communication.

Man and woman sitting on a dock by the water
Wait, how did we get to Amsterdam? I thought we were in LA!

Lead with Vulnerability to Unlock Meaningful Conversations

We can use lateral questions to find topics to pursue, and vertical questions when we find a topic worth pursuing.

But simply because the other person seems interested in a topic, it doesn’t mean the person is comfortable talking about it. Maybe there’s pain associated with the topic. Maybe the other person is self conscious about it. Or maybe they’re not used to having deeper level conversations with someone they just met.

In some cases, you will need to lead the conversation by disclosing something about yourself if you want your conversation partner to do the same.

And that’s where the cave analogy comes into play.

Woman standing in a cave
So THIS is what a conversation looks like…

The Cave Analogy—The Key to Deeper Conversation

Imagine approaching a dark cave with someone you just met.

How likely do you think they would be to walk into the cave if you asked them to go first?

You might find the occasional one who goes running in without a second thought, but is that typical?

Now, how much more likely do you think they would be if you walked in first with a flashlight and showed them it was safe?

This is why it’s important to lead a conversation by being vulnerable yourself. Vulnerability can be scary, so by going first, you allow the other person to be comfortable being vulnerable.

The Cave Analogy in Action

Alex: …and that’s why I adore living here!

Sam: Wow! Thank you for that excellent dissertation on the food culture of Los Angeles! How did you develop this incredible appreciation for the culinary arts? My parents weren’t around much so I basically raised myself—there were a lot of terrible meals made for years before I started to understand what goes into good food.

Sam is diving deeper so he wants to make Alex feel more comfortable answering a slightly personal question. Sam discloses personal information about himself by telling Alex his parents weren’t around much.

Alex: You raised yourself? Damn, that must have been hard. I’m sorry your parents weren’t there for you. My grandmother taught me everything I know about food before she passed away last year. I used to text her every time I tried something new or weird… like this one time I was in Thailand and tried a scorpion! Oh my gosh, have you tried one?

You can see how natural of a progression it was for Alex to bring up her grandmother even though the pain of loss is likely still fresh. Sam opened up about basically not having parents, and that resonated enough with Alex for her to talk about a grandparent she no longer has.

A man and woman sitting on bicycles and talking
So, wait—a scorpion?!

Not Everyone Will Follow You Into a Deep Conversation

Sometimes, however, it doesn’t matter if you ask all the right questions and do all the right things.

Everyone is different, and some people aren’t comfortable being vulnerable. Some people won’t open up until they trust you more or spend more time around you. There are any number of reasons a person might avoid deeper conversations.

But don’t take it personally.

Understand you have value as an individual and accept that some people won’t recognize it.

A skeptical dog
This little guy isn’t following ANYONE into a cave

Share Emotions, Not Facts if You Want Deep Conversations

We do not form connections based on facts.

We form connections based on emotions.

What does this mean?

For example, I don’t need to have grown up in the same town, state, or country you did in order to connect with you. If you went to school when you were little, we can connect on the emotional level of:

  • What school was like—fun, boring, interesting, terrible, etc
  • What it was like to make friends and lose friends
  • Embarrassing situations we got ourselves into
  • Funny adventures we went on with friends
  • Why we enjoyed certain classes and didn’t like other classes
  • How certain teachers inspired us and why
Three humans jumping in the air and looking happy
Close friends always jump in the air together

So, when you’re asking questions, remember to focus on the emotions and feelings related to the topic.

Sam: A scorpion?! No, I have not tried one! What was it like to eat one?

Alex: Actually, it almost tasted like chicken! Haha!

Sam: You are brave! And I’m sorry to hear about your grandmother—it’s hard losing the people close to us. What did you admire about her?

Alex: My grandmother was the best. You know those people who make you feel loved just by being around them? She was always so compassionate, and she never judged me when I messed up or did something I know she didn’t approve of. I always felt comfortable being myself around her and talking to her about anything. It’s a great feeling to have people like that in your life, ya know?

Sam: I do. I know exactly what you mean, and she sounds like a wonderful human. I have been fortunate enough to have people like that in my life as well. They are a gift. So many of us go through life doubting ourselves and never feeling like enough, yet all it takes is for one person to accept us for who we are in that moment and all that doubt just vanishes.

Alex: Beautifully said. You’re really easy to talk to. I’d love to chat more—can I get your number?

A woman holding a phone

In a Nutshell

We live in a world where we are constantly connecting with people.

But how do we transition out of those surface level conversations into something deeper that can create the opportunity for a relationship? And what’s the point of small talk at all if it doesn’t lead to anything more down the road?

The truth is, there’s no one-size-fits-all answer here.

If we want to make friends, create relationships, and ultimately sell our products or services, it’s important that we focus on creating a genuine connection based on shared positive experiences rather than just making small talk about the weather.

By understanding these two types of questions—vertical vs lateral—you’ll be able to navigate any conversation like an expert! Lateral questions move from one general topic to another. And vertical questions dig deeper into a general topic.

Don’t forget to lead with vulnerability so people know they don’t need to be perfect around you as this creates trust. This applies to texting as well.

And finally, share emotions not facts! Every conversation has a bit of depth if there’s emotion behind it.

If you want to learn more about transitioning from small talk to mentally stimulating conversations and meaningful connections, check out our latest toolbox episode of the Art of Charm podcast.

Do you want to make an unforgettable impression and step into the spotlight? Do you want deeper connections in your personal and professional relationships because your conversations often feel superficial or forced? When you’re able to show up powerfully, communicate exactly what you want, and get others on board—the possibilities for your life are endless! If this sounds like you, check out our Captivate + Connect program to learn how you will create strong first impressions that will quickly grab the attention of anyone, ignite authentic conversation, & leave a lasting impact!

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