Think of those conversations that never seem to get beyond the surface.
How's work? Good.
How was your weekend? Nice.
Been up to much lately? The usual.
Now think of the conversations that make you lose track of time.
The ones where one story leads to another, where you find yourself genuinely fascinated by what someone has to say, where you walk away feeling like you understand a little more about who they are.
What Makes These Conversations So Different?
We often assume it's the subject matter—that to have more meaningful conversations, we need to skip the small talk and start asking deeper questions.
But what if small talk isn't the obstacle to deep conversation, but the very thing that makes it possible?
Imagine Walking Into a Dark Room
You have no idea what's inside. There might be paintings on the walls, bookshelves full of fascinating stories, or doors leading into entirely different rooms.
But you can’t see anything clearly. You don’t know what’s there.
So you use your flashlight to scan the room, allowing yourself to discover what's there.
And when something catches your attention, you move closer, examine it from different angles, and begin to discover details you couldn't see from a distance.
That’s Precisely What Small Talk Is For
By asking a variety of surface-level questions, you’re using your flashlight to scan the room.
When you come across a topic that seems to spark the conversation, you know you’ve found something worth picking up and learning more about.
You ask deeper questions, seeking to explore this topic from different sides.
Go deep enough, and you may even learn why it matters to the person you’re speaking with and what that says about them.
The Art of Knowing What to Dive Deep Into
Consider how two conversations can begin in exactly the same way, yet end up somewhere entirely different:
You can spend hours talking with someone, collecting one piece of information after the next, yet walk away feeling like you barely got to know them.
So how do you know what to dive deep into so the conversation moves somewhere more interesting?
You don’t need to introduce some profound philosophical question. You simply need to notice an interesting detail, and probe further:
Rather than constantly moving from one topic to another, recognise an opportunity to move further into something that seems to:
- Make them come alive—a change in tone, facial expression, enthusiasm
- Matter to them—something they emphasise, linger on, or reveal a feeling about
- Make you want to learn more—something that sparks your own curiosity
The skill isn't necessarily asking better opening questions. It's asking better follow-up questions.
Often, that might simply mean repeating back the interesting signal you noticed (in the example above: “Your first proper holiday in ages?”).
What Makes for a Good Follow-up Question?
A good follow-up question follows what the other person has given you reason to explore.
Consider the difference between these questions:
- What do you do for work? → What drew you towards that kind of work?
- Where did you grow up? → What was it like growing up there?
- What do you enjoy doing? → What is it about that activity that you find so rewarding?
- What are you planning next? → What makes that something you want to pursue?
The first question gathers information about someone's life.
The second begins to explore their experiences, motivations, feelings, and values.
This makes the shift from learning about someone to understanding them.
The Perfect Question
There are countless lists online promising the perfect set of questions to spark meaningful conversation, some of which may be useful.
But perhaps we're placing too much emphasis on what to ask next, and too little on what someone has just told us.
That’s where you’ll find your cue for something worth diving deep into.
In fact, in a series of studies, psychologists found that people who asked more follow-up questions tended to be better liked by their conversation partners. Why? Because those questions communicated that they were listening, interested, and responsive.1
Not Every Conversation Needs to Be Deep
Sometimes the setting isn't appropriate.
Sometimes a lighthearted chat is all that’s needed.
And sometimes an attempted follow-up receives a short answer that tells us the other person would rather move on.
That’s perfectly fine.
The aim isn't to make every conversation deep, but to recognise when depth is possible and take that opportunity when the moment feels right.
The Next Time You Find Yourself Making Small Talk
Imagine you're holding that flashlight. Start by shining it around, asking surface-level questions.
Notice what makes them come alive, what seems to matter to them, and what interests you.
When you discover something worth exploring, stop moving from topic to topic.
Dive deeper. Ask questions that cover every angle. Seek to understand why it matters.
That's when small talk stops being a barrier to deep conversation and becomes the gateway to it.