How to Have a Deep Conversation
New York City’s Bryant Park is an oasis of green surrounded by a desert of grey concrete buildings. I sat on a dark green chair underneath a dark green umbrella overlooking a square of bright green grass.
“So how important is luck?” a voice inquired next to me.
I turned my head and met the eyes of an older gentleman sitting to the right of me. He looked like your stereotypical grandfather with a blue polo shirt, tan shorts, and hair gone completely white.
“Are you talking to me?” I asked.
“Yes! I was wondering what you learned from your book,” the gentleman followed up.
I glanced at the cover of the book on my table, Competing Against Luck, before looking back at the man.
“Oh, uh, I would say that luck is still very important to a business but the book’s point is that truly successful companies minimize luck by creating things consumers actually need.”
I thought that was the end of the conversation and was about to go back to reading when the man followed up, “I want to hear your thoughts then, would you say a company such as Uber or Apple figured out what consumers needed first or did they just build something great and then figured out how to market it?”
I paused to contain my surprise. That was the exact question I had been pondering. I shifted my body to face this mind-reading stranger.
“That’s a really interesting question,” I stated, “I think companies such as Uber and Apple still create products based on consumer needs even if it isn’t always obvious what that need is at first. For example, anyone who has ever been in a taxi knows that the experience is terrible. Uber just identified that pain point and created a product around it.”
“And what made you choose this book?” the man asked.
“My company gave every employee a copy. They think it’ll help boost innovation or creativity or something like that.”
“Guessing from the sound of your voice, you don’t agree?”
“Well it’s not that I don’t think it’s a good start…”
I proceeded to explain how I believed innovation needs to be at the center of everything a company does and that just giving away a book won’t suddenly make your employees more innovative.
The man probed into what I meant by the “center of everything” and we ended up having an hour-long conversation. I learned that his name was David and we moved away from talking about my job to talking about our personal lives.
I told David about the blog I was writing and I opened up about how I sometimes felt like a fraud because I’m not an actual expert in any of the topics I write about. I explained how I’m often torn between writing about topics I’m actually curious about versus topics I have more experience in.
Along the way I learned that David was in New York visiting his daughter. He had a military background but is now semi-retired, occasionally consulting for corporations.
After an hour we said our goodbyes — he to find his daughter and me to go back to reading. We exchanged email addresses and David promised to check out my website.
Even though my interaction with David happened years ago, the memory has stayed with me. I had a more meaningful conversation with a complete stranger than 99% of my conversations with friends.
That’s the power of a deep conversation: they stand out. In contrast, most of our day-to-day conversations are forgotten within 5 minutes of us having them.
Our normal conversations gravitate toward the same topics (travel, work, gossip, etc.) and we rarely talk about the bigger topics in our lives — ambitions, worries, beliefs.
It’s a shame because I truly believe a lot of the world’s problems would be solved if we just had more thought-provoking conversations with each other. That’s why I started Late Night Froyo, I wanted to write articles that sparked more intellectual conversations.[1] So I started researching interesting topics to bring up in conversations with my friends.
The quality of my conversations immediately improved. My friends and I began have deep conversations around interesting questions and topics such as whether the baker in Colorado had a right to refuse the cake to the gay couple. I learned which of my friends were thinking about getting a tattoo. I discovered intimate details about my friends’ upbringing and how it has impacted their worldviews. Through a handful of in-depth conversations, I felt more connected to my friends than from the countless interactions I’ve had with them before.
I also started talking to strangers. A lot of them. I interviewed NYC street vendors, struck up conversations with strangers in a park, and talked to random people over the phone. Every person I met had a unique story with their own personal challenges.
All these conversations changed my worldview. I realized that everyone has had different life experiences that has shaped them to be who they are today. And even if I don’t always “get” how someone thinks, I can at least at least understand what they’ve been through. More than anything, having all these conversations made me more empathetic.
I’m not an expert conversationalist by any means. I’m still terrified about approaching strangers and I still have awkward discussions that lead nowhere. But through the hundreds of conversations I’ve had, I wanted to share what I learned in the hopes that it will help you have better, more meaningful conversations in your life as well.
WHY WE NEED A FRAMEWORK
When I get into something, I get into it. So when I became interested in having better conversations, I examined existing articles, books, videos, even podcasts, that covered the subject.
What I realized is that while there’s a lot of available material covering conversational tips and tricks, there’s not a lot of information about an overall approach to having better conversations.
The advice is limited to tactics and conversation starters — how to maintain eye contact, tips to remember the other person’s name, conversation topics to bring up — but there is nothing cohesive to bring all the information together.
So when I tried putting the advice in practice, I would be so preoccupied running through a checklist of actions that I wouldn’t listen to what the other person was actually saying.
But I persisted. I kept having more conversations — some good, some painfully awkward — and over time, developed a system.
My goal is not to just give you conversation starters, but to share a mental framework for having better conversations. My belief is that by sharing an approach to conversations, you’ll spend less time trying to remember lists of things to do, and can spend more time focused on the conversations itself because your actions will come more naturally.
WHAT IS A GOOD CONVERSATION?
Let’s start by defining what it means to have a good conversation.
We instantly recognize a good conversation. Our voice feels heard and we feel connected to the people we’re talking to. We mull over what was discussed hours, sometimes even days later. But what separates these standout conversations from the everyday?
Good conversations have three characteristics in common:
Mutual Engagement
Forming a Connection
Personal Growth
Mutual Engagement
Mutual engagement means everyone in the conversation is mentally present and invested in the discussion. Each person is actively listening to what other people are saying and gives thoughtful responses or asks thought provoking questions that progress the conversation. You can tell when there’s mutual engagement when you can have a deep conversation for an extended period of time.
Mutual engagement does not mean everyone is constantly talking. Too much talking is actually a sign that people are more interested in hearing themselves speak than in having a real dialogue.
It’s obvious when individual members are disengaged based on their body language. They’ll constantly check their phone or their eyes will search for an exit.
Mutual engagement is the basis of any fruitful intellectual conversation. Because one person cannot have a good conversation by themselves, all parties need to put in the effort to speak and listen.
Forming a Connection
Forming a connection means emotionally bonding with the people you’re having a conversation with. You leave the conversation with a better sense of who they are, how they think, and what they care about. You don’t need to agree with all of someone’s beliefs to form a connection. You just need to empathize with the journey that led them to those beliefs.
The foundation to every connection is trust. Trust allows us to be vulnerable and share the parts of ourselves that we’re not always proud of. Trust is a self-fulfilling cycle. The more trust we give, the more we share about ourselves. The more we share, the more likely the other person reciprocates with their own vulnerabilities. The connection deepens leading to more trust.
That’s why a single spark of trust can turn a brief interaction into a genuine connection. For example, imagine a friend asks you about your day. Instead of giving the default “Good” as an answer, you explain how you’re mentally processing an email from your boss about your recent work performance.
By taking the small step to trust the person you’re talking to, you shared a vulnerable piece of information. In response, imagine your friend intently listens and supports you. They share how they are also facing difficulties at work. Your friend has opened up with their own vulnerabilities. As a result, you now feel more connected to your friend.
Personal Growth
The best conversations are the ones that grow you as a person.
I’m not talking about learning a new skill or discovering some new fact, but rather genuine personal growth. You exit the conversation with an expanded worldview from the one you entered the conversation with.
To achieve personal growth, you have to be exposed to viewpoints and opinions that you don’t necessarily agree with. You can’t grow if you only talk about topics you already believe.
This is hard because when confronted with ideas that don’t align with our own, our immediate reaction is to shut it down. We start thinking about how we’re going to prove the other person wrong or we change the topic as quickly as possible. Either way we stop listening and we end our opportunity for growth.
Good conversations can be uncomfortable. Having moments where your beliefs are challenged is natural because it means your perspective is being stretched. The worst thing you can do is end a potentially meaningful conversation because you don’t agree with what is being said. The most difficult conversations are often the ones that develop us as a human.
The most difficult conversations are often the ones that develop us as a human.
WHY DO WE HAVE CONVERSATIONS?
Now that we know what a good conversation involves, we can begin our journey to have more of them. The first step is understanding why we have conversations in the first place.
It’s tempting to think that we have conversations solely to exchange useful information. When our ancestors roamed the Serengeti, having conversations did allow them to know which berries were poisonous or where they saw a herd of antelope. This helped our forefathers survive and pass on their genes, so it is easy to believe that this is why conversations evolved to be an innate part of human behavior.
But this isn’t the complete picture. It doesn’t capture the range of conversations we have. We discuss our childhood and tell each other our hopes and dreams. We argue about politics and have extended debates about what is right and wrong. These conversations cover topics with little direct survival benefits, yet are the conversations we find the most engaging. There must be a greater purpose to conversations than just passing on information.
In fact, conversations have two additional purposes: to group and to impress.
Grouping People
Our brain is wired to group people together. The most prominent mental group are the individuals we label “friends & family.” These are the people we are the closest to and care the most about. But we also group people into other categories such as “co-workers,” “Republicans,” “Americans.” It’s how we make sense of the world and decide whether to trust someone, and whether we feel obligated to attend their kids’ birthday party.
We use conversations to determine the groups that someone belongs in. In ancestral times we would have chatted about someone’s family tree, favorite hunting spots, and the weather to look for common denominators. In modern times we talk about TV shows, sports teams,politics, and still, the weather. We try to determine if the other person belongs in similar groups as us (“in-group”) or are in groups different from us (“out-group”). Although we don’t always consciously make these judgements, our behavior is still affected.
You’ll know what I’m talking about if you’ve ever discovered an unexpected detail you had in common with someone else — a shared hometown, a favorite British TV show, matching tattoos . Suddenly you feel the urge to like the other person more even though their personality hasn’t changed. As we’ll discuss later, we tend to like people similar to us.
Using conversations to group people also explains why we gossip. Gossip not only tells us who belongs to which group, but it also strengthens our position in the group. If you’re gossiping with someone, it means we belong in the same group as them.
Impressing People
The other reason we have conversations is to impress people. Even though we would like to think we treat everyone the same, our natural tendency is to treat people differently. We look up to the rich and famous and we (unfortunately) tend to look down on the downtrodden.[2] Although we may hope for the contrary, there’s a natural hierarchy to the world. Sometimes that hierarchy is formally defined — such as in a corporate environment where we have a boss and employees, and sometimes that hierarchy is unspoken — such as a woman who is the leader of her friend group.
Our social standing influences how we see ourselves, who we are friends with, and who we have a relationship with. We tend to seek romantic partners on a similar level as us. That’s why when we see a supermodel dating a plain looking guy, we assume that the guy has other characteristics that elevate his status — he’s famous, has a lot of money, or is unbelievably funny.
Conversations are a way for us to climb the social ladder. We share our vacation plans or show off our new handbag because we want to impress other people with the exciting details of our lives.
This may seem shallow and self-centered, and especially if you don’t like being the center of attention, you may believe you’re beyond showing-off. But if you have ever left a conversation wondering how the other person felt about you, then you’ve cared about your social standing. We may not always consciously show-off during a conversation, but we all enjoy being validated. It feels good when we tell a story that makes people laugh and it feels good when our friends are impressed with our promotion. So we subconsciously seek more of those positive experiences out.
At the end of the day, we care about how people see us and conversations are one way to manage those perceptions.
SO WHY ARE GOOD CONVERSATIONS SO TOUGH? (AND WHAT WE SHOULD DO ABOUT IT)
Given that we’ve been talking to each other for thousands of years, you would think we would naturally be good conversationalists. But in fact, our innate human nature actually makes having deep conversations difficult.
By having conversations that exchanged information, grouped people, or increased our status, our ancestors were more likely to survive and pass on their genes. Our ability to have intellectual debates or discuss literature isn’t from some higher moral imperative, but because having those conversations supported our own selfish evolutionary interests. As a result we have predisposed biases that influence our every conversation.
Sometimes these evolutionary forces make our conversations better. We discover a shared hobby with someone that labels them as a “friend.” Or we feel compelled to share a funny story about our trip to Italy because it subconsciously raises our social status. But other times, our natural tendencies hold back our conversations. Someone says something that rubs us the wrong way and we end up in a shouting match because our evolutionary instincts view them as a threat. We stop listening to someone because we’re so preoccupied with coming up with the next impressive thing we are going to say.
In particular, we have natural mental barriers that block the elements (mutual engagement, connection, growth) that define a good conversation. So the first step to having better conversations is to shift our mindset to recognize and address these blocks. Only after we have changed our thinking about conversations can we take the actions needed to improve our conversations.
Only after we have changed our thinking about conversations can we take the actions needed to improve our conversations.
Mutual Engagement Barrier: We like to talk but we don’t like to listen.
A good conversation is a continuous back-and-forth between two people. One person leads the conversation by talking while the other person follows by listening. At some point, the roles can switch and the person “following” now leads. There is a constant balance between listening and expressing yourself.
You can’t have a good conversation if both people are trying to lead.
But because we are naturally self-centered, our impulse is to bring the conversation back to us. Even when we are supposed to be listening, we are often thinking about our response or how to connect the conversation back to ourselves.
Here’s an example:
Amy: I’m not sure how I feel about my new boss.
Joe: Oh really? When I got my new boss I was super nervous as well. It definitely took me few months to get acclimated to her leadership style. Those were crazy times.
Amy: Yeah my boss sent me a note asking to meet on Monday to talk about my performance.
Joe: You should prepare what you’ve done for the last 6 months. I know when I got a new boss, my first meeting with her was to show her what I work on and my accomplishments.
Amy: Yeah but the tone sounded more friendly, like he wants it to be informal.
Joe: Yeah, I don’t know, I still think you should be prepared.
Amy: Yeah, maybe.
Aaron Sorkin I am not, but I hope the example gets the point across. Amy is trying to explain her concerns to Joe, but Joe is too busy thinking about his own experiences.
As a result, two people are just taking turns talking about unrelated topics. This example illustrates how easy it is to leave a conversation feeling like a lot of talking was done, but not a lot of listening.
The problem of overtalking is magnified when you’re discussing a topic with opposing viewpoints. You may start off listening to the other person’s point, but after you encounter an opinion you don’t agree with, it’s easy to switch to debate-mode.
When that happens, you spend all your effort trying to convince the other person about your position. You may be emotionally invested in the conversation, but you’re no longer engaged because you stopped listening. The conversation devolves into a shouting match where two people talk on top of each other.
MINDSET CHANGE: A successful conversation isn’t one where you talk, it’s one where you understand.
The reality is that most people won’t change their mind and don’t want your advice. Most people just want to express themselves and be understood. Changing someone’s beliefs is usually extremely difficult, if not impossible.
The best we can do is understand the other person. This means not just listening to what the other person is saying, but empathizing with them and trying to see the world from their view.
In the book How to Talk How to Listen, Mortimer Adler calls this the “meeting of the minds.” It’s when one person fully gets the intended meaning behind what another person is saying and both people have a shared understanding. In general, but especially on topics in which you don’t agree, your number one goal for the conversation should be to fully comprehend what the other person is saying.
You should not just be able to explain what you think the other person is saying, but also articulate the points in a way that the other person would agree with. This requires spending significantly less time talking and much more time listening.
Listening is hard. We are always tempted to relate the conversation back to ourselves and our interests. Resist that temptation and instead focus on understanding the other person more. That’s what this mindset shift is all about.
Connection Barrier: Separating Us & Them
Having a meaningful conversation requires connecting with another person on a personal level. It’s not enough to just know facts about the other person, you need deeper insights about who they are and how they think to really form a bond.
Creating that connection requires trust and vulnerability. You have to share parts of yourself that you may not be 100% comfortable with and hope that the other person accepts you for who you are. That is intimidating because by opening yourself up, you’re also allowing yourself to be potentially hurt. It’s incredibly painful to try and form a genuine connection with someone who doesn’t reciprocate the effort.
Consider the two example scenarios:
Amy: “I’m really worried about the future of my job because I can feel my job being slowly automated.”
Nancy: “Oh I’m sorry to hear that. Oh by the way, have you seen the latest Ariana Grande Instagram post?
Amy: “I’m really worried about the future of my job. I feel like I’m in a difficult position right now where I can feel my job being slowly automated.”
Nancy: “That’s a dumb thing to say. No way robots are going to take our job.”
In both cases Amy is reaching out to Nancy for support. And in both cases, Nancy shuts Amy down. Nancy either changes the subject or dismisses Amy’s concerns. If you cringed while reading the dialogue, that’s because getting rejected really hurts.
That’s also why we are so selective about who we are vulnerable with. We use conversations to mentally group people into people who we can and can’t trust.
We’re more likely to be vulnerable with our friends and family than a guy we just met at a bar.
But our tendency to group people also has a downside — we actively distance ourselves from people who we perceive as not belonging in the same groups as us.
In a famous study done in the 60’s, teachers separated students into blue-eyed and brown-eyed groups. Throughout the day, the teachers would artificially elevate certain groups with praise (e.g. “Blue-eyed students are the smartest”) and special privileges (“Brown-eyed students get to sit in the front of the class”). The students immediately took note and separated themselves based-off eye-color.
A similar study separated boys at a summer camp into two random groups. Halfway through the summer, the groups were introduced to each other. The two groups immediately saw the other group as rivals and each group would insult and prank the other group.
These studies illustrate the power of the groups that form in our mind. Once we create the internal dialogue of “us” versus “them,” we hold back our ability to connect with “them.” We start seeing “them” less as individuals and more as stereotypes of the groups they belong in..
In life, “them” is anyone different from you. If you’re a Democrat, Republicans can be “them.” If you’re white, “black people” can be “them.” If you love Star Wars, Star Trek fans are “them.” Anytime we make a broad-sweeping generalization about another person, we create the “us vs. them” story. And when we do that, our ability to connect with that person vanishes.
MINDSET CHANGE: Everyone has their own story.
To overcome this mentality, we need to see people as more than just their labels. We need to see people as PEOPLE.
No matter what someone says or believes, everyone sees themselves as the main character of their own story. Everyone has a reason to act how they do. And while people are capable of doing some horrible and unkind things, nobody sees themselves as a villain.
This isn’t to say that you need to always agree with someone else. People say hurtful and ignorant things. But if your immediate reaction is to label someone you don’t agree with as an “idiot,” you dehumanize that person and destroy the chance for a genuine connection.
Only by treating people as individuals worthy of our respect can we build trust. And that trust is crucial for us to open up to them and for them to open up to us. That’s the only way a personal connection can be formed.
GROWTH BARRIER: Our echo chambers.
If the previous mental barrier is our tendency to disregard the thoughts of people different from us, our final mental barrier is our tendency to overweight the thoughts of people similar to us.
When we group people into “us vs. them,” the “us” is made up of people who share our beliefs, opinions, and values. We enjoy hanging out with people like ourselves. In one experiment, psychologists matched random people up to have a conversation. Prior to the conversation, psychologists gave each person some information about who they were about to talk to. The catch is that the information was bogus and was tailored to make each person feel like their partner was similar or dissimilar to themselves.
Psychologists found that not only did people naturally like individuals who were actually similar to themselves, but even when participants just thought the person they were talking to had a similar background, they were predisposed to like them more as well.
And because we like people who think like we do, we seek those people out as friends. That’s why smaller colleges actually promote more diverse friend groups. In larger colleges there are more people so you’re more likely to end up befriending people who happen to share your exact interests.
We end up living in an echo chamber surrounded by points-of-view similar to our own. Technology has only amplified the reverberation. With so much available information on TV and the internet, we gravitate towards the content that matches our predispositions.
For personal growth to happen, you have to be open to changing how you think. But our echo chambers hold us back because our echo chambers close our mind to new ways of thinking. In the back of our heads, our mind is already made-up.
So we ignore any information that contradicts our existing viewpoint and we refuse to believe other positions can be valid. No matter how much we listen during a conversation, if we refuse to change our thinking, the conversation will be pointless and personal growth will be impossible.
Mindset Change: Usually we’re wrong (because there’s no “right” answer).
We need to be more humble. This is the hardest mental barrier to overcome because it requires us to acknowledge the limitations we face. No matter how educated we think we are about a topic, we need to recognize that all the news sources we consume, all the content we read, and all the discussions we have had, are likely with sources and people that align with our pre-existing beliefs and provide a one-dimensional narrative.
To overcome our echo chambers, we need to be as critical about the information that supports our beliefs as the information that goes against them. This is easier said than done. Especially for complex issues (e.g. systemic racism in America), there often isn’t a “right answer.” Every point-of-view has pros, cons, limitations, and trade-offs.
Let’s look at an hypothetical example:
Diane: How can you choose to eat meat? The meat industry is terrible to animals being killed for your benefit. For what? Just so you can have a Big Mac whenever you want?
Joe: They’re animals! That’s where they fall on the food chain! We don’t feel bad when lions and sharks hunt their prey, why should we feel bad if we eat meat? Think about all the jobs that would be lost if the meat industry didn’t exist. This is a first-world problem because people in many other countries would starve if they didn’t have meat.
Diane: But you’re smarter than an animal and not in a third-world country. You have a choice so you should take it. Look at this horrible video of KFC treating its chickens and tell me you can continue to eat meat.
Joe: I do have a choice and I’m choosing to eat meat. I like how meat tastes and that’s why I usually try to choose organic or free-range meat whenever possible.
Both people are simply reiterating the facts that support their case without acknowledging the other person’s point. In this case, as in many other cases, there isn’t a real “right” answer.
It’s true that eating meat requires killing another living being. But it’s also true that the living being is also not human. Eating meat is a personal decision based on a number of factors such as how you value animal life, what you believe is the natural order of things, and what alternatives are available to you. So arguing about the right decision is futile because an objective “right” doesn’t exist.
Most of our values and beliefs are not based on rational, calculated, reasoning. Our environment and upbringing have a large role in impacting how we think. So the beliefs that we feel most strongly about are more a reflection of how we were brought up than any actual standard of truth.
…the beliefs that we feel most strongly about are more a reflection of how we were brought up than any actual standard of truth.
The best we can do is recognize the limitations of our beliefs and keep an open mind. Joe shouldn’t try to argue with Diane, he should ask her why she believes the meat industry is so bad and use the conversation as a moment for self-reflection. The point is to break out of our ingrained beliefs and allow ourselves to be convinced of alternative viewpoints.
I’m not saying there are two equally valid sides to every debate. There are concrete facts (e.g. Earth is round) as well as prevailing moral principles (e.g. killing people is bad) in which there is clearly a dominant position. But for most of our beliefs, we wildly overestimate the strength and rationality of our position and underestimate the influence of our echo chambers and biases.
So to break this mental barrier, we need to see conversations as chances to learn and grow. Only then can we have better, more meaningful conversations.
HOW TO HAVE A GOOD CONVERSATION
After breaking down our mental barriers, it’s time to tackle the actual conversation itself. Conversations progress through three stages.
Pleasantries — where we talk about facts
Small talk — where we talk about opinions
Big Talk — where we talk about beliefs
While each stage doesn’t require equal time, you typically pass through each stage to reach the subsequent stage.
To have a good conversation, the positive conversational elements identified earlier (mutual engagement, personal connection, and personal growth) need to be in each stage though each stage tends to draw out certain elements more than others. You’ll naturally promote these elements in your interactions with the right mindset which is why breaking down our mental barriers is more impactful to having a good conversation than trying to remember a list of conversational tips and tricks.
But there are a few specific behaviors that can improve your conversations at each stage. We’ll take a look at each stage and discuss one action per stage to help progress your conversations.
Pleasantries
The first stage of a conversation is pleasantries. This is when two people try to get a sense for the sort of conversation they are about to have.
Especially when you meet someone new, this is where the standard conversation starters are exchanged: “How are you doing?” “How’s work going?” “What plans do you have for the weekend?” We say these things not only to start the conversation, but to also gauge the level of engagement we can expect from the other person.
If the other person gives a canned response, we use that as the basis for the rest of the conversation and the exchange will likely be brief. But if the other person gives a more thoughtful answer, their response opens the door to discussing more interesting topics.
At the same time, we’re also signaling our own engagement through what we say and our body language. Are we on our phone? Are we looking around to other people? Are we making eye contact? These are all cues to signal how invested we are in the conversation.
KEY ADVICE: Break the script.
To signal that you want to have a deep conversation (provided you actually want one of course), you need to “break the script” — either by giving a non-standard answer or giving a non-standard question.
When we first start talking to someone, especially someone we’ve just met, we default to certain topics: work, culture, vacation plans, gossip. Because they are predictable topics, we give predictable responses.
Here’s an example conversation:
Olivia: How was your weekend?
Joe: Good! I went with some friends to the beach on Saturday to relax. And on Sunday I ran some errands and picked up groceries.
Olivia: Oh that sounds nice, which beach?
Joe: Jones beach.
Olivia: Oh I’ve heard good things about that beach, I need to check it out.
Joe: Yes definitely, can’t recommend it enough.
Olivia asked standard questions and Joe gave standard replies. Unsurprisingly, the conversation was brief and didn’t lead anywhere. That’s fine in our day-to-day work conversations where we need to be efficient with time, but our conversations with friends often fall into similar patterns as well.
That’s why when you’re in this stage of the conversations, you need to push the dialogue with interesting questions and interesting topics that truly engage the other person.
So how do you do that? It’s less about what you do than what you don’t do. DON’T ask the standard questions and DON’T give standard answers.
Imagine instead that the conversation with Olivia and Joe had gone like this.
Olivia: How was your weekend?
Joe: Good! I went with some friends to the beach on Saturday to relax. And on Sunday I ran some errands and picked up groceries.
Olivia: Would you say that you’re more of a lay on the beach person or a take a hike in nature type of person?
Joe: Hmmm, I think I am generally a hike type of person but this weekend I really just had a desire to relax. I had a really stressful week so I wanted a day where I did nothing.
Olivia: Interesting…what do you think makes someone fall into either camp? I’m totally a beach person because I’m like you, I treat the weekends as time to have no obligations. But I know some people can’t wait to be active during the weekends which I’m always surprised by. What do you think?
Joe: Huh, I guess most weekends I feel like I’m sitting at my office all day I just want to get out. It’s funny you say that because I have a friend…
During the pleasantries stage, we tend to focus on facts such as upcoming weekend plans or events that happened at work. Facts are easy to talk about because they are straightforward and non-offensive. But fact-conversations often quickly dry up because there’s nowhere for a conversation to go from a fact.
Instead, look for opportunities to ask for opinions. Opinions engage the other person because it forces them to put thought behind their responses. It also starts to move the conversation out of the realm of the scripted and into the next stage.
Small Talk
After we exchange pleasantries, the conversation moves into small talk. This is where we reveal more about ourselves by talking about our opinions on different topics.
We give our take about the latest TV show. We gossip about the latest drama that happened within our friend group. We ask for advice about our dating life. The conversation is interesting, but not necessarily substantive as personal beliefs and values are not usually shared.
Even though small talk sometimes has a negative connotation, there’s nothing wrong with small talk. Most of our conversations fall under small talk. You can’t start a conversation just jumping into discussing someone’s innermost thoughts so that’s why small talk has a role.
Small talk fosters the connection and trust between people that leads to the vulnerability needed for “big talk.” The goal for this phase is to open the dialogue.
KEY ADVICE: Listen, Validate, Repeat.
To do that, listen, validate, and repeat.
Listening means actively hearing and comprehending what the other person is saying. Validating means understanding the “why” behind the other person’s statements and affirming their emotions.
You don’t need to agree with someone to validate their feelings. Validating just means standing in the other person’s shoes and empathizing with where they are coming from.
If you continuously repeat these steps, you’ll build trust with the person you’re talking and they will increasingly open up. The steps are simple but not easy. You need to listen and validate while withholding our urge to pass judgement or give advice.
That’s because in most cases, people don’t want our help or advice, they just want to be heard. When facing a problem, people usually already know what they are going to do, talking about it is simply a way to cope. So when someone comes to you with a problem, resist jumping in with how you think they should act. Instead, hear them out and simply affirm that it’s okay for them to feel how they do.
To see validation in action, let’s look at the following scenario
Katy: I am so sick of Meg as my boss. She’s the worst!
Alexa: What happened?
Katy: She just sent me an email asking for something she needs tomorrow.
Alexa: Oh that sucks, did she give you a reason why she needs it so urgently?
Katy: Yeah apparently her boss asked her for it and she knows that I’m the only one who can do it. I can’t believe Meg just rolled over like that.
Alexa: This sounds like a frustrating situation, I’m sure it doesn’t feel great that she signed you up for a project with a short-term deadline without asking you first.
Katy: Yeah, if she had just checked with me first, I would have been okay with it. But the fact that she volunteered me without asking is a little insulting. I could have had plans tonight instead of working.
Alexa: No I totally get that. What are you going to do?
Katy: I guess I have to do it. I’ll probably set up time to talk to Meg after I do it because I don’t want this to be a regular occurrence.
Alexa: That sounds like a smart approach.
Katy: Thanks for understanding, I just needed to vent.
All Alexa did was take the time to understand where Katy was coming from and then validate those emotions. Even if Alexa believes that Meg’s ask was reasonable, Alexa can still be supportive in understanding why Katy might feel differently.
Katy already knew her course of action, she just wanted Alexa to listen and be on her side.
Katy now feels better coming out of the conversation, and the closer connection between Alexa and Katy can potentially lead to a deeper conversation.
Big Talk
Big talk is the final stage. This is where deep, thought-provoking conversations occur. You move away from talking about opinions and instead talk about the beliefs and values that define us. When you think of a meaningful conversation, you’re thinking of big talk.
Big talk is when we’re most likely to be exposed to new ways of thinking through deep conversation topics that change how we think. Big talk done right and you’ll have an emotionally fulfilling conversation that brings you closer to the person you’re talking to. But this stage is also the most risky.
Having a deep and personal conversation can ruin a relationship if one or both parties use it as a chance to attack the other person.
The key to big talk is vulnerability. One person needs to take the first step to open up to the other individual. Only then will the other person feel safe to reciprocate. And since you’re the person that wants a better conversation, that person is usually you.
KEY ADVICE: Take the first step to being vulnerable
In the prior stage, you engaged the other person in conversation by validating their feelings and emotions. You built trust through understanding. But to make it to big talk, it’s not enough just to listen, you need to push the conversation forward.
Take the first step to guide the conversation into deeper topics by opening up. Share something that keeps you up at night. Explain an idea you have that everyone may not agree with. Talk about your insecurities or your ambitions.
Let’s look at an example:
Hannah: I’m really glad I got to see my nephews before I left Iowa.
Dave: Yeah it sounds like a great time with your family! Does spending that much time with your nephews make you want to have kids?
Hannah: Yeah I think so.
Dave: It’s funny, even though I came from a big family, I actually don’t think I want to have kids.
Hannah: Oh really, why is that?
Dave: This may sound a little selfish, but I know how kids are a lot of work and your life changes once you have them. I want to travel more in life and also advance my career so I’m worried that kids may hold me back.
Hannah: Wow that’s really brave of you to admit and those are perfectly reasonable feelings. I guess I never thought about why I even want to have kids, it just seems like the expected course of life.
Dave: Yeah I don’t always bring it up because I feel like most people don’t feel the way I do. Sometimes I try to avoid sharing certain thoughts because I’m not sure how people would react. Do you know what I mean?
Hannah: Yeah, I actually was at a work event and everyone was talking about our hiring processes and…
In this conversation, Dave took the first step towards vulnerability by admitting his uncertain feelings towards having children in the future. While this isn’t necessarily a controversial opinion, it is a belief that goes against the norm. Yet Dave took a risk at potential judgement by discussing his feelings.
Hannah could have responded by glossing over the statement (“Yep, kids aren’t for everyone”) or even casted judgement about it (“How could you not want kids?”) but instead she recognized and respected Dave’s statement. She lightly probed into why Dave feels the way he does and because Dave has sparked a safe space to have a meaningful conversation, Hannah also felt secure enough to talk about a personal experience as well.
We take a risk when we open up at being judged or that the other person doesn’t positively respond to our vulnerability. We need to accept these possibilities and not let any poor experiences from our past hold us back from being able to form genuine connections in the future. From my experience, if you genuinely open up to someone else, generally they will accept you for who you are.
A WORD ABOUT THE JOURNEY
So to have a deep and meaningful conversation you progress from pleasantries to small talk to big talk. Along the way, the trust between you and the other person strengthens, allowing both parties to discuss increasingly personal topics.
However, I don’t want you to think that you need to reach big talk to have a “good” conversation. Not every conversation goes all the way to big talk. Most of our conversations stay in the pleasantries or small talk territory and that’s perfectly okay .
Our day-to-day conversations are functional — we’re working on a project with a co-worker or having a quick catch-up conversation with friends. A brief round of pleasantries is totally fine before discussing whatever task is at hand.
And if you’re having a quick catch-up with a friend, the conversation will likely stay around life updates, gossip, and other small talk topics.
While having deep, meaningful big talk conversations are fulfilling, they are also time-consuming and exhausting. Small talk exists for a reason: it’s entertaining and requires less emotional and mental investment. We don’t always want to have an hour-long conversation about our upbringing, sometimes we just want to discuss the latest Marvel movie.
All a good conversation requires is mutual engagement, personal connection, and personal growth. Although certain elements are easier during certain stages of the conversation (e.g. personal connection during the small talk stage), each element plays a role in each of the stages of a conversation.
You can still foster mutual engagement during the big talk stage by actively listening to the other person and you can still form a personal connection during the pleasantries stage by mentally humanizing the person you’re talking to.
So as long as we actively address the barriers that hold us back, and take a few easy steps during the course of a conversation, we can try to make every conversation a good conversation. And along the way, we can learn more about others and ourselves.
ONE MORE THING…
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[1] As you can see, I continued writing articles that interested me.
[2] I’m drawing a distinction between what we naturally do and what we “should do.” Just because this is what we do doesn’t mean we should treat people differently.