3 steps for creating deeper conversations.

How interested do you think strangers and acquaintances are in hearing your personal stories?

If you’re like most people, your answer is probably somewhere between “not very” and “not at all”. In fact, a study from 2021 found that most people assume personal conversations with someone they don’t know well are likely to feel awkward and uncomfortable.

But according to the study (and confirmed by my almost 2-decade-long career)—that assumption is wrong.

After asking the study participants to predict how personal conversations with strangers would feel, the researchers had them engage in both shallow and deep conversations. Afterwards, the participants filled out another questionnaire to describe what the conversations were actually like.

Their findings were clear: deep conversations felt significantly less awkward than expected and created more genuine connections.

And I don’t think we need to cite a study to agree that uninteresting small talk can be both uncomfortable and disconnected, do we? (At least unless you do it correctly and avoid making it uninteresting in the first place;)

In other words, when we hold ourselves back from having more personal conversations because we worry that it might be awkward, we’re actually making it more likely that things will get awkward and blocking connection at the same time!

So why do so many people make this mistake?

The simple fact is that we underestimate how interested people are in hearing other people’s stories.

Because even though the facts and circumstances of our personal lives might be very different from each other, the fundamental human experiences that exist within them tend to be things we all share. So relating to them isn’t just easy—it’s interesting.

Now, don’t get me wrong, I’m not saying that every stranger out there wants to listen to your 3-hour one-person show about your childhood. But, generally speaking, those who have an interest in having a conversation with you would much rather have a relatively deep one than a shallow one.

And besides, these conversations shouldn’t be initiated by launching into long monologues about our most traumatic experiences, but by gradually getting more personal together.

Three steps to gradually deepen conversations.

Step 1: Replace your autopilot questions with intentional ones.

The easiest way to start leading into a more personal conversation is to ask a question that’s just slightly more personal than what you’d otherwise ask. Something that most people don’t ask and that lets the other person choose how deep they want to go.

So instead of asking “how was your weekend?” try something like, “so what’s been on your mind lately?” or “what’s something you’re excited about these days?”

If they engage even just a little by answering these questions with more than half-dismissive answers like, “Oh, not much, just work, I guess”, they’re showing you that they’re interested in getting a little more personal.

Step 2: Reward them for going deeper.

When someone engages with your personal questions, it’s important to show them that what they’re saying interests you—or at the very least that you appreciated that they shared.

The best way to do this is to ask genuine follow-up questions—questions that show that you’re curious about hearing more.

If you can’t think of any, or it doesn’t feel fitting to what they told you, the next best thing is to express appreciation for their answer. You can literally just thank them for sharing, or show excitement or appreciation in the way that you continue the conversation.

Step 3: Match their depth—and add to it.

After you’ve listened, asked follow-ups, and/or expressed your appreciation—or whenever they ask you a question in return—it’s your turn to share something real.

If you want to deepen the conversation more, a good rule of thumb is to go just slightly deeper than the other person did. You can do that by being more vulnerable or honest, sharing something you don’t often share, or sharing just a little bit more than they did.

Keep in mind that we’re still not launching ourselves into long, dramatic, intimate monologues. We’re just sharing a little bit more of our true selves.

Don’t overthink it.

When people see that you have an interest in them as a person and that you’re equally willing to be open and personal in return, odds are that things will start to move forward on their own. In most cases, the conversation will end up at a level of personal exchange that both enjoy.

The goal of these conversations shouldn’t be to go super deep fast, but simply to connect with people we meet about things that matter to us. Our lives, interests, passions, and so on.

And the good news? You don’t have to wait until the next time you have a conversation with a stranger to start practicing. You can practice this with friends, family, coworkers, and whoever else you regularly talk to.

Sure, it won’t necessarily feel the same as it might when you’re talking to someone new—but practicing replacing your habitual surface-level questions with more meaningful ones will make it a lot easier to ask them to new people later on.

Have fun with this!
-TJ

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Source: Kardas, M., Kumar, A., & Epley, N. (2022). Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology, 122(3), 367–398. https://doi.org/10.1037/pspa0000281

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