On conversation

I want to have more conversations about conversation. Conversation is often overlooked and taken for granted, something that’s part of our everyday lives. But how often do you pause and think about what separates good conversation from bad conversation? Reading Jonny Sun’s essay “On proof” in his book Goodbye, again, I started to think about my relationship with conversation. 

I think I’m generally pretty fun to talk with. This is potentially self-aggrandizing to say (and I recognize that there’s always room for growth), but it’s especially noteworthy, because I used to be painfully shy. I distinctly remember a day in elementary school when I inexplicably decided I didn’t like the sound of my own voice. After that, I stopped raising my hand and speaking up in class. 

Some of my teachers found my shyness endearing, interpreting it as a byproduct of my studious and obedient nature. Other teachers found it frustrating, a sign of my rebelliousness and cavalier attitude. One day in elementary school, my music teacher was explaining time signatures. After soliciting different examples of time signatures from volunteers (i.e., people who actually raised their hands), she cold called me (i.e., someone who had not raised her hand). I mumbled “6/8.” In front of the entire class, my teacher asked why I hadn’t raised my hand if I knew the answer. 

Another time, after I visited Taiwan for three weeks in third grade, my teacher asked if I’d be willing to share with the class about my visit. I immediately panicked, and she empathetically and gradually reduced the size of her request until she finally asked if I could simply show my classmates where Taiwan was on a globe. I nervously agreed, but felt an immense sense of relief when this never manifested. 

But I was never shy at home and as I grew older, the circle of people I felt comfortable around steadily and naturally expanded. I’m fortunate for my Midwest upbringing. Growing up in Indiana, my friends and I never had much “to do” when we hung out. We would simply go on long walks or spend extended amounts of time talking in each others’ basements. When I first started college, I was befuddled with other people’s fixation on finding things “to do.”

These days, I’ve evolved into a gregarious person who is energized by talking and attention, but recharges by being alone. After interacting with a wide range of clients (thanks to my consulting background) and going on a lot of first dates (thanks to dating apps and my need for human connection), I feel pretty comfortable having a conversation with almost anyone. I love having conversations now, and it’s how I feel close to people. 

(Separately, I have a working theory that no one is actually shy - people just need to be in environments where they feel comfortable and safe expressing themselves fully. It’s on less shy people to cultivate these environments.)  

I want to share and reflect on what I’ve seen people do and what I’ve tried to emulate to make a conversation more enjoyable for everyone. As a caveat, of course the qualities that make conversation great are subjective and of course, sometimes you have ineffable chemistry with someone that makes the conversation naturally more fulfilling and this is hard to emulate. 

When you’re speaking:

1. Be cognizant of how much space you’re taking up: 

This is probably the most obvious tip, but conversations typically shouldn’t feel like they’re interviews. When I went through sorority recruitment freshman year of college and had 1:1 conversations with the women in sororities, I thought I wasn’t allowed to ask them anything about themselves. The conversations I had with these women consisted of them asking me questions, while I provided a response and awaited the next question. (Unrelated or maybe tangentially, I did not end up joining a sorority.) 

Great conversations don’t need to be a constant or equal back-and-forth where one person shares an anecdote and the other person rallies back with another anecdote. I love going in-depth about experiences my friends have had, even if that means one of us will be talking for a longer period of time at that specific point. But I also am conscious of how much time I’m speaking for. If I realize I’ve been talking for a while, I’ll generally try and direct the conversation to the other person or the next time I chat with that friend, I’ll let them do more of the talking. 

2. Use humor and self-deprecation to create a more comfortable environment: 

Growing up, I had a vivacious friend who could easily talk with anyone. When we were in middle school shopping at the mall, my dad would pick us up afterward, and she would have no problem happily chatting with him when he asked us what we had bought. By contrast, I always froze up whenever any of my friends’ parents tried to talk with me and provided them terse, stilted responses. 

One of the things I learned from this friend is that sharing vulnerable and self-deprecating anecdotes can create a more comfortable environment for others. Her silly stories took the pressure off of me to come up with conversation topics. I was free to just laugh and poke fun at her for whatever antics she had found herself in. 

These days, I use this trick especially when I’m talking with more taciturn friends or people that I’m not as familiar with. I’ll attempt to break the ice by sharing something goofy about myself and try to foster a comfortable environment. 

Some people are quick to label others as “self-absorbed” when they talk about themselves, but I find it endearing that people will make fun of themself to make others feel more at ease. 

When you’re listening:  

1. View listening as an act of love: 

This one is also inspired by an essay (“Who gets to speak?”) in Goodbye, again. 

There’s a popular saying that you should “listen to understand, instead of listening to respond.” I generally agree with this, but I want to take this a step further. I recently started viewing listening as an act of love, a way for me to show someone that I am paying attention to what they’re saying and care enough to let them fully express themselves uninterrupted. I’m generally pretty impatient so sometimes when someone is talking, I have a bad habit of wanting them to hurry up and finish so I can respond. Especially when someone is long-winded, I feel like I already understand their point early on and am wasting the rest of my time waiting for them to finish. 

But recently when I started viewing listening as an act of love, I’ve found myself more patient with friends in conversations. I consider it a privilege that they want to share certain details of their lives or certain thoughts with me.

2. Ask (specific) guiding questions: 

Have you ever had a conversation that goes something like this: 

Friend: Hey the pictures of your vacation looked awesome! I want to hear all about your trip! 

You (not knowing how to answer such a broad, generic remark, so you provide a similarly broad, generic response): It was great! We had good food, the place was beautiful, and it was so nice not having to worry about work.

Friend: Nice! 

*Neither person says anything, unsure where to go next with the conversation*  

These conversations are not very fulfilling for either party. Previously, when I had conversations like that, I used to think there was something wrong with me, and I was disappointing my friend by not providing a more detailed and juicy answer. But now I think some of the onus is actually on the listener to ask more specific guiding questions. As a listener, you have an active role in shaping the conversation and helping your friend go into more detail about what they’re talking about. Your friend likely wants to share more, but doesn’t know how much you want to hear or where to begin.  

I like to ask people how they feel / felt in certain situations or to explain a point they made that I might not completely understand. I also like when people ask me these questions, because it helps me crystallize thoughts I wouldn’t have a chance to otherwise. 

People generally enjoy talking about themselves, so if you provide space for that by asking questions, they will frequently leave the conversation feeling good. 

Asking questions is also my secret trick for furthering a conversation when I’m not sure what else to say. 

Of course, not everyone likes answering questions and conversations don’t always have to be heavy and introspective. I do try and read the people in the conversation to see if a question is an appropriate way to continue the conversation. 

Final (for now) thoughts: This is in no sense comprehensive, but again more than anything, I’d love to have more conversations about conversations. When you think about the people you enjoy talking with, what stands out about the way they converse? Let me know!