How to Have More Meaningful Conversations

You don’t have to talk about the weather ever again — unless you want to

“Don’t talk unless you can improve the silence.”

— Jorge Luis Borges

How often have you found yourself in the middle of a pointless conversation, wondering how you got there? One moment, you thought you were entering an interesting discussion. The next, you’re desperately searching for an excuse to leave.

I’ve been there more times than I can count. Some variations of the meaningless conversations I’ve had included:

• Being asked for opinions on topics I have no clue about. Did you really just ask me whether the property market has gone up or down in the past year?
• Someone lecturing me on their favourite topic for hours. Do you even care if I’m listening?
• Talking just for the sake of avoiding awkward silence. How did I end up talking about that — and how do I stop?
• Stale conversations when no one’s eager to say much at all. Is anyone going to make an effort here, or am I the only one who cares?

Even just writing about those moments makes me cringe.

In the past year, I started being more proactive about the conversations I’m having. To be clear, I still consider myself a beginner. But here’s the best part: I discovered that, even as a beginner, there are so many things you can do to make your conversations more interesting and meaningful.

What I’ll share with you here is a blend of the lessons I learned from participating in mindfulness circles, playing authentic relating games, doing therapy, and talking to clients in my freelancing business. On the way, I discovered three ingredients of meaningful conversations — and practical ways to cultivate them.

But why should you even care about making your conversations more meaningful?

How Your Conversations Impact Your Future

Having meaningful conversations may not seem like a big deal. Every day, people talk about whatever comes to mind. We rarely stop to think about what we want to say — and what makes its way into our conversations by default.

This happens because spoken words are so intangible. We say them, they last for a millisecond and then they fade away. We may feel like we have limitless words at our disposal. If what you’re talking about right now isn’t exactly what you want to say, you can keep adding upon it indefinitely in the future.

However, what if you looked at conversations from a different perspective?

• First of all, whatever you say can’t be unsaid. Your words lead to a reaction from your interlocutor. These, in turn, influence you. In that sense, each moment of a conversation is causal to what happens next. With every word and sentence, you plant a seed (consciously or not) for what will follow.
• Second, as the recent pandemic has shown us, we can never know the future. The fact that you’ve been meeting your friend every week for a cup of tea for the past three years doesn’t grant you’ll see them next Wednesday. Why wait with what you want to talk about until “the next time” that may never come?
• Finally — and maybe most importantly — whenever you talk, you shape your future self. Verbalizing your thoughts forces you to choose some things and leave others out. With each sentence, you shape the bigger narrative of your life. You reinforce certain stories, beliefs, and feelings over others.

For example: When someone asks you about your weekend, you can’t share every detail of it. You need to choose what you’re going to say. Will you lead with the stressful dinner with your in-laws? Will you mention the serene Saturday morning when you finally got a chance to start reading that new book? Or maybe you’ll shrug and say “Oh, you know, the usual,” proceeding to ask them how they’ve been.

Those choices may seem insignificant at first. But when you make them over and over, they have a very real impact on your life.

You probably heard that “whatever you focus on, grows.” This isn’t some wishy-washy new age mantra, but a phenomenon confirmed by science. At the core of it is the concept of neuroplasticity. It means that your brain is constantly adapting and reshaping during your lifetime, based on what you pay attention to:

“There’s a traditional saying that the mind takes the shape it rests upon; the modern update is that the brain takes the shape the mind rests upon. For instance, if you regularly rest your mind upon worries, self-criticism, and anger, then your brain will gradually take the shape — will develop neural structures and dynamics — of anxiety, low sense of worth, and prickly reactivity to others. On the other hand, if you regularly rest your mind upon, for example, noticing you’re all right right now, seeing the good in yourself, and letting go (…) — then your brain will gradually take the shape of calm strength, self-confidence, and inner peace.

You can’t stop your brain from changing. The only question is: Are you getting the changes you want?” — Rick Hanson, PhD

The above is true for the thoughts you think, but even more so for the words you speak. By choosing which thoughts you verbalize, you send the signal to your brain: This is important. Additionally, whatever you mention in a conversation elicits a response from the other person. This way, what you talked about gets reinforced even more.

In the long run, the conversations you’re having are shaping your brain — and, as a consequence, your life. Knowing this, shall you decide to be more deliberate about your conversations?

The 3 Components of a Meaningful Conversation

To me, a meaningful conversation isn’t necessarily about “deep stuff.” My definition of it is very simple and inclusive — and it only has two criteria.

A meaningful conversation is one that:

• I want to be a part of.
• Enriches me in some way.

I wanted to increase the likelihood of having those conversations. The first step was to become aware of the baggage I was bringing with me which sabotaged that desire.

Over the past year, I started becoming acutely aware of the unconscious patterns I played out in my conversations. For example, when I started therapy, I became particularly conscious about the way I tend to talk about my problems.

On the surface, whenever I bring up my issues, I claim that I’m looking for a solution. I want to be practical about it. But as I started going deeper into my therapy, I realized that I wanted something else even more than a solution to my problems.

This thing was to be seen, understood, and sometimes, even pitied.

Because of that, I was victimizing myself through the way I presented my struggles. This didn’t just manifest in the relationship with my therapist, but also with my friends. The intention I had on a conscious level (them helping me solve a problem) didn’t align with the deeper, more primordial need (being seen). Because of that, my conversations felt disconnected and empty.

One thing I learned was that aligning my conscious intention with the underlying need was the way to have more meaningful conversations. Then, I realized that two other components — mindfulness and curiosity — also helped, even when my intention wasn’t clear.

You can see the components below as three possible “portals” to open up a meaningful conversation. I found it’s enough to focus on just one in any given interaction. Then, the other two follow organically.

1. Conscious intention

When I started examining my conversations, I realized that for virtually any interaction, I had some sort of intention. The question was whether I was aware of it or not.

Sometimes, the intention was as obvious as “landing a client” in a business Zoom call. When I was meeting a friend for a catch-up, it could be “refreshing our connection” or “sharing my ideas” with her. However, sometimes I could feel that the intention was hidden — and I couldn’t pinpoint what it was.

These were usually the times when I had an unmet need — but wasn’t fully aware of it.

I realized that to encourage a meaningful conversation, the easiest way was to get clear on my intention. Whenever an unconscious need was running the show, I was driven by a “hidden agenda.” I would try to manipulate the conversation for a particular outcome — but wasn’t even aware that I was doing it.

When you bring your unconscious need above the surface of awareness, you realize that this need also breeds a hidden intention. Once you see it, you have the power to decide. Do you want to navigate your conversation based on it — or do you want to consciously plant a new intention?

You can ask yourself whether your current intention supports your long-term growth — i.e. whether it’s wholesome. A lot of unconscious intentions are based on patterns from the past that aren’t necessarily beneficial for your present self. When you become aware of them, you have the power to change.

Remember: your intention doesn’t have to be deep or existential. It’s more important for it to be clear than to be deep. When I spoke about this to Sílvia Bastos, relationship coach and co-founder of JournalSmarter, she said:

“Sometimes the intention is just to explore freely and to get to know each other. Then, there doesn’t need to be a topic or a strict format. Remaining open to whatever comes up is the intention. But even then, it’s useful to remain aware of that intention throughout the conversation.”

This is where we touch upon the next aspect of meaningful conversations: awareness of what’s going on in the present, aka mindfulness.

2. Mindfulness

Being mindful in a conversation allows you to stay in touch with whatever’s unfolding in the present. You can monitor whether or not you’re being guided by your intention, but also — you stay open to what the other person brings into the equation.

Mindfulness can sometimes be misinterpreted. A lot of people associate it with bliss, harmony, or even being in control. A meditation teacher and mindful communication expert Susan Piver debunks this myth. According to her, this is what mindful conversation looks like:

“Mindful does not mean peaceful. It does not mean in control. It can certainly include those things. But what mindfulness really means is letting down your guard, opening to whatever situation you’re in and whoever you happen to be speaking to. (…) If you’re not letting what’s happening touch you, odds are you’re trapped in your hopes for how things should go or your fears for how things may go. And that is not mindful.”

Being mindful allows you to take your attention off a desired — or feared — outcome, and put it on the present moment. This ensures that your intention doesn’t turn into controlling. Intending for something to happen is very different than forcing it at all costs. Being mindful allows you to see that difference.

To be mindful often means to stay curious about what’s unfolding. These two qualities are like two sides of the same coin. When you’re mindful, you naturally become more curious, and vice versa.

3. Curiosity

Curiosity is the opposite of denial. Being curious means to acknowledge that there’s something you don’t know — and then, be open to learning about it. Being in denial means you’re not willing to admit there’s something to learn in the first place.

This brings us to an elegant definition Nadine Clay used in her recent article about cultivating curiosity. She defined curiosity as “the desire to resolve uncertainty or fill a gap in one’s knowledge.” From this perspective, curiosity is a feeling — but, as Nadine says, it can also be a sense-making skill:

“Every day, there are fragments of knowledge waiting to be collected and pieced together if you’re able to see them. Curiosity is the light in a kaleidoscope of knowledge, connecting the fragments into a work of art. It’s a powerful emotion that holds pieces of information together and forms new connections. Learning, after all, is defined by making new connections.”

Being curious in a conversation allows you to collect pieces of knowledge — about yourself, the other person, the subject matter — and put them together to make meaning. It also allows you to stay open to the unexpected caveats of a conversation and visit places you weren’t expecting to see.

Curiosity is especially useful when you’re uncomfortable in a conversation — e.g. feeling inferior, bored, out of control, or overpowered by the other person. If you can become curious about that discomfort — and maybe even investigate it out loud — you change the course of the conversation.

You can invite meaning by simply being curious about what’s unfolding.

As I said before, all these elements are interconnected and support one another. Cultivating one supports the other two.

Together, they breed what I like to call a podcast mentality. The best podcasts you’ve listened to are intentional conversations — but they’re not controlling. They’re a shared exploration of a topic and the relationship between interlocutors.

A good podcast host usually has a few questions prepared in advance. However, they won’t desperately cling to them if the conversation naturally gravitates somewhere else. The podcast guest also has an idea of what they’ll talk about — but they’re open to questions. In this sense, both of them have intentions — but they don’t control the conversation with an agenda. They’re curious and mindful about what unfolds and let themselves be guided by it.

A meaningful conversation is one that has a purpose, but also, affords the participants the freedom to express themselves. It’s the sweet spot between rigidly following a plan and mindlessly talking about whatever.

Of course, how the conversation unfolds depends on everyone involved, not just you. However, you can increase the likelihood of having a meaningful conversation by learning how to cultivate intention, mindfulness, and curiosity.

The best part? You don’t have to consider yourself eloquent, confident, or a “good conversationalist” to do that.

The Practical Guide to Meaningful Conversations

This guide is a collection of practical ideas to make your conversations more meaningful. You don’t need to use all of them to make a change in your life. Focus on those that match your context — and apply them.

Ultimately, remember that you’re going to learn through trial and error. I learned most of the below through failing to make meaningful conversations. Eventually, I was able to see the mistakes I made over and over — and started dodging them.

This is how you’ll learn as well: through experience. There’s only so much we can learn about relationships from reading about them. The rest is practising in real life.

I’m offering these tips to help you get started.

How to Create an Intention for Your Conversation

I took a closer look at my intentions when I noticed myself bored with more and more conversations — including with my closest friends. I realized that, sometimes, we had no idea why we were having that conversation in the first place.

Again, this doesn’t mean we should always be discussing something serious. Most of the intentions I bring to my conversations are simple. They revolve around wanting to be heard, asking for advice, holding space for someone, etc. These are things most people naturally look for in their conversations.

Being aware of the intention, no matter what it is, helps you know the “why” of the conversation. This usually means you’ll find it more interesting and purposeful.

Whenever I want to establish my intention for a conversation, this is the process I mentally go through:

1. First, I take a moment to check whether any intention is already present. Some questions to help with that: What do I hope to experience in this conversation? What drives me to meet this person? What do I want to talk about? How do I hope this conversation will make me feel?

2. Then, based on what I find, there are three possible courses of action:

• If I pinpoint a wholesome intention and I’d like it to guide me, I simply affirm it. Some examples include: “making a clear and honest pitch to a prospective client,” “getting vulnerable and honest with a friend” or “remaining open to get to know this stranger.” This is the most straightforward way to work with an intention. You simply acknowledge it, affirm it, and let it guide you in the conversation.
• If I find an intention I consider unwholesome, I ask myself: “What new intention can I plant to make this conversation more meaningful?” An example can be becoming aware of the intention to victimize myself. Knowing that this doesn’t serve me, but stems from a valid need to be seen, I ask myself: “What is a more wholesome intention to help me meet this need?”
• Finally, sometimes I find myself not aware of any intention at all. If you’re meeting someone but don’t know what you want from it, you can either (1) open yourself to whatever comes and find meaning in the conversation by staying curious and mindful, or (2) create any intention you want.

If you want to consciously plant a new intention for your conversation, here are a few tips:

Dedicate a moment of “white space” to find the intention

Sometimes, we don’t know what we want simply because there’s too much going on. When your mind is constantly jumping from one thing to another (e.g. you’re in meetings all day), there’s little space left to consciously connect with your intention for what’s next.

But even creating 2–3 minutes of “white space” — a time when you don’t do anything at all — can bring you to a place of clarity. You can, for example, schedule a few minutes of “white space” before the next call. Just by sitting with your thoughts and doing nothing, you may become clearer on what you intend this particular conversation to look like.

Use a list of possible intentions

To uncover your specific intention, you can keep in mind that there’s a “pool” of generic needs and desires that drive human behavior. They can differ in their individual expressions — but at the core, people are motivated by similar things.

There are different psychological models to describe them, but it doesn’t matter so much which one you use. The point is to present your mind with a list of ideas for what your current need or desire may be. From there, you can pick one that resonates with you and create a wholesome intention to fulfill it.

Here are a few lists I recommend starting with:

• Maslow’s Hierarchy of Needs
• Needs Inventory form The Center for Non-Violent Communication
• 16 Basic Desires listed by Steven Reiss, Ph.D. from his book Who Am I?

Consult your feelings

Sometimes, I find it hard to come up with any intention. I think and think about it — and then nothing comes.

Something I learned with my Gestalt therapist is that our needs, desires, and intentions often communicate themselves through feelings. When I find myself hesitating about what I want to explore during our session, she asks me what my body feels like in relation to different topics. I found this is a helpful way to connect to my intention.

When you pay attention to how your body resonates with certain topics, you may notice that some of them “light you up.” Others cause your body to feel dull, tired, or restless. You can use those feelings to understand what excites you and brings you joy in a conversation.

Co-create with the other person

An important thing is to keep in mind that your intention doesn’t exist in a void. The person (or people) you’re talking to are, consciously or not, bringing their intentions to the table.

If you feel safe enough, it can be a good idea to explore the intention together. I found many times that just asking a simple question at the start of the meeting — “What would you like to talk about today?” — makes both parties more aware of their intentions. It also increases the chances that the topics will be more interesting because you’re now picking them consciously.

However, sometimes you may be the only one concerned with the intentionality of the conversation. In that case, you may find yourself being “dragged” into a conversation you don’t care about by the other person.

In that case, remember that your intention can be renewed at any point. Sílvia Bastos told me:

“The key is to be aware of what intentions are surfacing organically. When the conversation goes stale or we disconnect from what makes us feel alive in it, the awareness that this is what’s happening is particularly important.

For example, one person may talk about themselves for a long time and you’re getting bored. If you’re not aware of the power you have to redirect the conversation, then it’s much less likely that it’s going to improve. You’re not aware of the intention that you could create in that moment, if you decided to.”

Propose a structure

Sílvia also shared with me that, sometimes, the simplest way to reinforce an intention is to decide a particular format for a conversation. In a personal conversation, she recommends authentic relating games — i.e., a structure for a meaningful conversation that everyone agrees to beforehand.

When we talked, she told me:

“When you have a defined intention, a format, or a structure, it gives you space not to have to think so much about it throughout the conversation — “Where do I want to go from now?” — because you already decided that.”

This way, you have more “processing power” to explore the conversation itself, since you’re not questioning the intention anymore.

I found this tip to be quite useful in my business meetings. Whenever I talk to a client, I try to lead the conversation by laying out the intentions and structure of the call. I found this is a great way to organize my (and my clients’) thoughts and get to the point quickly.

The important part whenever you propose a structure or format is to check with others if they’re happy with it, too.

How to Be Mindful in a Conversation

To remain mindful in a conversation means keeping your attention on what and how is being said right now. What happens in the present has the priority over trying to avoid or accomplish something specific in the future.

Of course, sometimes you have a clear goal in your conversations — landing a client, reaching a decision, solving an argument, etc. That’s fine and doesn’t exclude being mindful. You can still pursue your goals — but when you’re mindful, you won’t do it at all costs. For example, I’m not going to lie or dramatically lower my rates just to land a client.

I found a helpful framework for what it means to have a mindful conversation in this talk by Susan Piver, a Buddhist teacher and expert in mindful communication. She explains how mindfulness transforms the way we communicate:

“Most communications are sequential monologues. I make my talk, you make your talk, and so on. But a third thing enters every communication, and that is “us.” That’s why it feels one way to tell your ideas to your mother and another to tell your ideas to your boss — because the space changes. You’re the same, the ideas are the same, but the space changes. And the attunement to that space is a source of skilfulness in a conversation.”

The attunement to that space of “us” is what a mindful (and meaningful) conversation thrives on. According to Susan, four pillars facilitate this attunement. Here’s how I’ve been practising them in my conversations — and how you can, too.

1. Timing

Timing is about knowing when it’s your turn to speak and listen. This is what makes a balanced conversation, where both parties have a chance to express themselves and be heard — but also, to hold space for each other.

This isn’t about a perfect, 50:50 distribution of speaking and listening. In most conversations, one person will naturally speak a bit more than the other. What’s important is to maintain the feeling of balance. This way, everyone rests assured they can be both the giver and receiver in the communication.

How to practice it in your conversations?

I’ve been struggling with this for a long time. My natural inclination is to listen rather than talk. Then, when I finally start speaking, I often hear a voice in my head saying something along these lines: “That’s enough, Marta. You’re probably boring them to death. Ask them a question and stop talking.”

Usually, this is my insecurity speaking. The other person can very well be interested in what I have to say. But I need a way to discern whether that’s indeed the case — or whether it is my turn to shut up and listen.

The technique that helps me with that is quick reality checks.

I set myself an external trigger that reminds me to check-in with what’s happening. For example, whenever we’re ordering another round of drinks or I need to go to the restroom, I’ll withdraw from the conversation for a moment to ask a few internal questions:

• Does the other person look interested in what we’re talking about?
• Am I enjoying the current topic or do I secretly want to pivot?
• What does my body feel like?
• What is the body language of the other person telling me?

Noticing a few extra details often gives me a clearer perspective on whether I’ve been talking or listening too much or too little. Then, I can adjust accordingly — either by shutting up or becoming more confident about what I have to say.

2. Listening

Mindful listening isn’t about what you do. It’s about what you don’t do.

To be a mindful listener, you need to stop one habit that most people have: Using the time the other person speaks to think about what you’re going to say next.

Susan Piver says that it can be scary because it requires you to forget yourself. As she put it, to listen mindfully, you need to “cease thinking your thoughts and start thinking my thoughts.” How can you do that?

How to practice it in your conversations?

I often catch myself drifting off in my thoughts as the person in front of me speaks. I started realizing that this often makes me miss out on important nuances of their story.

This often happens when I feel insecure in a conversation. I may start thinking up my “lines” in advance to find a sense of control over the situation.

The first step to overcome this is to acknowledge the insecurity — and then, let it go. By “letting go,” I mean it quite literally, on the physical level. When I notice tension in my shoulders or an unnatural posture, I make a conscious decision to relax. The effect is usually immediate: relaxing my muscles sends a signal to my nervous system that I’m safe.

From this place, I can tune back into what the other person is saying. I may ask them to repeat the part that I’ve missed. I found that most people appreciate it when I honestly admit that I drifted off. This tells them that I care about their story enough to make sure I haven’t missed anything important.

Once I’m back on track, I try to put aside all the assumptions about my interlocutor. If it’s a family member or a friend I’ve known for a while, I try to approach them as if I’m meeting them for the first time. Not looking at the other person through the prism of your assumptions is the key to mindful listening.

You can check if you have any preconceived ideas about the person you’re talking to, such as:

• “This person is more successful than me.”
• “I can see where this is going — she’ll bore me to death with her work problems again.”
• “I’m convinced that this person doesn’t like me.”
• “He won’t know what I’m talking about, so there’s no point explaining.”

Such ideas may cloud your perception of what the other person is saying. The more you strip off your assumptions, the more mindful of a listener you become.

3. Agendaless-ness

To be agenda-less in a conversation is to be more open to how the process unfolds than fixated on the desired outcomes.

You still can have an intended goal for the conversation — e.g., closing a business deal or solving a problem. However, you don’t get so hung up on that goal that you become blind to what happens right in this moment.

How to practice it in your conversations?

To me, agendaless-ness is closely connected to staying curious (we’ll talk more about it shortly). But there’s also one simple trick that you can do to drop your agenda, even without curiosity.

That trick is to ground yourself in the material reality.

Whenever I notice myself obsessing about the outcomes of a conversation, I make a conscious effort to pull myself back into the physical space. I do that by consciously noticing my surroundings.

You can do it by becoming aware of simple sensual perceptions, for example:

• The colour of the walls in the room you’re in,
• The temperature of the coffee mug you’re holding in your hands,
• The texture of your trousers,
• The sounds coming from behind the window.

Focusing on the raw physical sensations in the present recalibrates your attention. It reminds you that you’re here, in this moment, in this conversation, that may or may not meet your agenda. You honour the present more because you become aware that that’s the only time you truly have.

When you realize it, whatever agenda you had naturally becomes secondary.

4. Confidence

It may not be intuitive, but confidence is an essential pillar of mindful communication. Feeling confident means being at ease. This is when you aren’t driven by your insecurities or defensive programming. Thanks to that, you can steer the conversation in a bolder and more meaningful direction.

Susan Piver says that feeling confident doesn’t require you to feel superior to the other person. You don’t even have to believe in yourself. Inducing confidence is surprisingly simple and it can be done in almost any conversation.

How to practice it in your conversations?

This is a tip that I copy-pasted from Susan’s talk into my life — and it’s been working for me ever since.

The guaranteed way to generate confidence in a conversation, Susan says, is to “place your attention on maximizing the other person’s position.” This simple trick sets up the interpersonal dynamics in such a way that you almost have no choice but to feel confident.

Highlighting someone else’s achievement or recognizing their skills puts you in a position of power. By acknowledging them, you sent a subtle yet powerful signal that you’re confident enough about your position to maximize theirs.

I use this technique often to reverse power dynamics when I feel overwhelmed. When I voice positive things I notice about the other person, they’re often humbled. Within seconds, they start relating to me differently.

Finding a way to maximize the other person’s position can restore balance in a conversation. At the same time, it can make you feel more connected, confident and empowered.

How to Stay Curious in a Conversation

The common misconception about curiosity is that we can’t do much to experience it. Either you’re curious about something or not — end of story. This is how most people I know think of it.

But this is true only if you believe it is. Once you open yourself to the possibility that curiosity can be nurtured, you’ll see how easily this can be done.

In her recent article, Nadine Clay frames curiosity as a skill that can be trained — but also, a habit of the mind. Through self-experimentation, she first induced curiosity very deliberately and in specific moments. Then, she found that the more she practiced it, the more it became her default state.

“Curiosity transformed from a temporary state that arose when I wanted answers to a question into a powerful emotion that permeated every aspect of my life. (…)

Before my self-experiment, curiosity seemed like a temporary state — a fleeting moment of an impulse to explore a question that I may or may not have acted on. Now, after actively and meticulously cultivating it, it feels like an emotion. It’s with me all day, regardless of what I’m doing.”

That’s very aligned with the concept of neuroplasticity we mentioned in the beginning. Whatever you focus on grows, remember? That’s why it’s so important to start inviting curiosity to your conversations. The more you do it, the more your brain will become “optimized” for it. You’ll start experiencing curiosity spontaneously.

Here are three tips I use to become more curious in my conversations — especially when I feel bored. I’m convinced that every situation has an aspect you can become curious about if you only want to.

1. Notice unconscious scripts driving your conversation.

In many situations, we conduct conversations based on how we handled things in the past. Because of the way you were raised, the people you met, the culture you grew up with, you may be “programmed” to approach certain types of conversations in particular ways.

If you do that on autopilot, you don’t engage with them. Instead, you follow a script.

To become curious about the conversation you’re having, you must first become aware of your script and choose to leap beyond it. To give you an idea of what your scripts could be, here are some of mine:

• Meeting a new person from abroad. In this context, there are questions I default to without even thinking about it. Where are you from? What do you do? How long have you been living here? What do you miss about your country? There’s a certain pool of information I assume I need to acquire. Nothing wrong with that — but this is a script that easily puts me on autopilot.
• Talking to my parents on the phone. Recently, I realized that my default script with my parents is to talk about myself, highlight my accomplishments, and reassure my parents that I’m doing alright. I noticed that this keeps me from (1) being vulnerable with them and (2) learning about how they’re doing.
• Catching up with a good friend. My script in this context is to try and skim over their and mine life events that occurred since we last spoke. It’s as if both parties needed to have detailed knowledge of the other’s “timeline.” However, I noticed that this isn’t always required. The urge to follow this script can keep me from exploring the topics I’m genuinely curious about.

What about you? Do you notice any automatic scripts coming up in certain types of conversations? Once you become aware of them, you can leave them behind.

Letting go of the urge to follow a script clears out space for curiosity.

2. Ask the right questions.

Asking questions is one of the most powerful ways to ignite curiosity in a conversation. In one interrogative sentence, you have the power to zoom in or out on the topic that appeals to you. Or, you can even change the course of the conversation completely.

But it’s important how you choose the questions you ask. A good rule of thumb is to only ask what you’re genuinely interested in. Sílvia Bastos told me:

“Ask only questions that you’re curious about. This is a great way to keep the conversation alive and meaningful. Don’t ask stuff you don’t really want to hear the answer to. If you do that, you’ll feel disconnected and the other person will feel it, too.”

To ask questions you’re interested in, listen for the details in what the other person is talking about. Are they going on and on about their hobby and you’re becoming bored? You may pick up on something that grabbed your attention and ask them about that.

For example, recently my friend John has been talking a lot about trading stocks which I have no interest in. I was becoming bored and impatient. But when he mentioned how to be a good trader, you need to detach from making emotional decisions, it piqued my interest. I became curious about how trading impacted him on the emotional level.

I asked about that and the topic pivoted to something that we were both interested in.

Additionally, you can always have a “back-up list” of topics in the back of your mind. This is the stuff you’re generally interested in and you can always ask how the other person relates to it. Use your “back-up list” to reignite the conversation when it’s stalling.

A few items from my list include:

• The other person’s relationship with their parents;
• How they decided to do what they do professionally;
• Where they traveled in the world and what was their most fascinating travel experience.

I resort to these topics when I see the conversation is going nowhere. Because I’m always curious about them, the other person picks up on that curiosity and often gives interesting answers.

3. Bring awareness to the relational aspect of the conversation.

Becoming aware of what happens on the relational level is an almost guaranteed way to spark curiosity. This is connected to the attunement to the “us” space that Susan Piver talks about.

I discovered this in therapy when I started reflecting on what happens between my therapist and me in real-time. Sometimes it feels uncomfortable, but that discomfort is always compensated with something I consider invaluable: curiosity about what’s arising in our interaction.

Sílvia Bastos confirms that becoming aware of the relational level of a conversation prompts us to become curious:

“The more we bring awareness to the relational level — not talking about external topics and abstract concepts, but about what happens between you and me — the more exciting and alive the conversation will feel. If even one person is aware of this relational level then, inevitably, the other is brought into that space as well.”

Talking about what happens between you and the other person in the moment immediately adds authenticity to the conversation. As Sílvia said, even if you’re the only one aware of this relational aspect, you can invite the other person into that space, too. You can simply mention something connected to the relational level of your interaction.

Here are a few examples I sometimes use (or hear from other people):

• What you just said made me feel warm inside/taken care of/a little uneasy/[insert a description of your current feeling].
• I’m noticing that you’re checking your phone every other minute. Is everything okay? Is there an urgent message you’re waiting for?
• Because I just joined, I feel a bit confused. Would you mind giving me a quick update on what you’ve been discussing so far? (in a group conversation)
• When I said this, I noticed you became a bit tense. Would you like to share what happened for you in that moment?

Adjust these kinds of observations and questions to the context you’re in and how comfortable you feel with the other person. Don’t push it. Naturally, you won’t talk about the relational aspect with your boss in the same way you would with a friend.

The point isn’t to push anyone’s boundaries. It’s about gently bringing a bit more awareness where you feel it could benefit the conversation.

Parting Message

The point of this article isn’t to urge all your conversations to be deep and philosophical. This isn’t about being serious all the time, nor is it about perfection.

Making your conversations more meaningful is a form of fine art. You learn it through personal trial and error. You gradually discover what a meaningful conversation even means to you, based on what you’d like to see more of in your life.

The value of your conversations isn’t only found in what you talk about, but also how. I hope that, by now, this “how” aspect is a bit clearer. In my experience, the answer to “How to talk to others so that the conversation is worthwhile?” can be contained in three words.

Intentionally, mindfully, curiously.

Allow these three words to navigate your conversations. Remember that you probably won’t be able to force those qualities. But, you can certainly do a lot to encourage them.

If you do that for a while, you’ll start reshaping your brain to naturally gravitate towards more meaningful conversations.

Imagine in what ways this could transform your life. All you need for it to happen is to add a bit more intention, mindfulness, or curiosity to one of your conversations — today.

Thanks for reading! If you enjoyed this, you can support my work by buying my book Ego-Friendly on Gumroad.