How to have great (and meaningful) conversations.

One of the questions I get asked most commonly when I tell people about the time I spent talking to strangers about love is “how do you get people to tell you all these intimate stories of their lives?”. Umm… I generally love talking to people and have been doing this for really long, so I hadn’t really formally thought about it. Until recently though, when for a project I not only started watching and reading a lot about conversations and interactions, but also began to talk to a lot of people about it.

Now, I am by no means an expert, but I did realise that over the years I have developed some of these skills and they have been immensely useful — the conversations I have had have inspired me, brought me jobs, taught me so much of what I know, and given me a strange kind of robust support system, one that involves intimate friendships that I can count on as also a whole world full of strangers to learn from; conversations have seen me through my worst times and humbled me through my best. I have found belonging in the world through these conversations. Which is why, I thought I would put down some notes of what I learnt about meaningful conversations while interacting with strangers as my day job.

There is merit to connections and good conversations, there really is! Kio Stark, who talks about stranger interactions, describes this beautifully: “I’m obsessed with talking to strangers. I make eye contact, say hello, I offer help, I listen. I get all kinds of stories.About seven years ago, I started documenting my experiences to try to figure out why. What I found was that something really beautiful was going on. This is almost poetic. These were really profound experiences. They were unexpected pleasures. They were genuine emotional connections. They were liberating moments”

Before I get started, let me add two qualifiers. (1) No, I am not fully an extrovert (if we were to at all conform to that dichotomy). I love people, and I get a lot of my energy from talking to people, can open up to anyone, but I am also terrified of large gatherings and large group conversations and will usually occupy an observatory corner spot when I do attend those, love spending conspicuous long amounts of time alone and preferably even away from the internet and cannot have small talk to save my life (no seriously, if you put a gun by my head and told me to have small talk or you will kill me, I will die). The point being, this isn’t an extrovert or introvert-oriented list. (2) As many stories I have of the most fantastic conversations, I have also messed up more times that I would like to admit, in more ways that I fully comprehend, and have my own share of dramatically embarrassing moments. I shall spare you the details, but this list also encompasses the lessons I have learnt after.

Anyway. Without further ado, here is a seven-point non-preachy checklist for having better, more meaningful conversations, with anyone:

“Despite how open, peaceful, and loving you attempt to be, people can only meet you, as deeply as they’ve met themselves.” — Matt Kahn

You are “people”. You cannot have a deep and meaningful conversation with someone else if you have never had one with yourself. The best conversations have elements of wholeness, of thoughts and opinions that are connected to beliefs and values, and by extension, to feelings and emotions. One cannot respond authentically to a story about sadness and hurt, for example, if one has no idea how it feels to experience sadness and hurt. You don’t have to have gone through what someone has gone through (and you probably never will) — but the language of emotions can become a shared vocabulary only when one can empathise with what that root feeling is.

And it is not just about emotions. For someone to go to deep places within themselves in conversations, it is important to create a shared safe space where that is okay — and if you are hesitant about those spaces in your life, or if you have never gone there on your own, people know, and that will almost always block off deeper conversations.

Let me take a moment to clarify what I mean by “deep” — I do not mean the deep dark secret places where all the TMI is stored. I mean more of the things that people hold slightly more intimately, not just in the forms of their stories, but also their perspectives; the places where connection happens. These places might sometimes not be as brightly lit or as happy as one would like and might indeed often have stories that are slightly hard to respond to, but in my experience, the best wisdom I have found in conversations, the parts that I have carried with me — they all come from there. And if you have never sat in those places in your own hearts, you will probably not be able to be comfortable in someone else’s deeper places.

This metaphor (also a result of a beautiful conversation) explains this beautifully: you cannot build a strong house on the surface. You are going to need a strong foundation to build a strong house. And that foundation requires some digging. If you have never got your hands dirty, that digging is going to be way harder for you.

We know this in many ways. You know how we often say “there was something about her that made me want to talk to her”? I made a list of people I would put in that category and had conversations with them about this. And one thing struck out — they all really did inculcate those traits. Maybe they didn’t start off that way all the time, but genuine interest in someone else’s life, some measure of curiosity, a certain amount of positivity and cheer, a definite kindness — these are all things that they had worked to build within themselves, and that showed. I am sure there are ways of faking this that I don’t know of, but here’s my philosophy — if I can actually be positive and kind and curious with a little bit of effort, wouldn’t that make more sense than constantly putting in the effort in pretending to be so? ¯\_(ツ)_/¯ Plus, in just more practical terms, this is also a good way to know what works well for you, and what doesn’t, what your triggers are — and allows you to be more alert about them in the conversations.

2. Practice good conversations

While it is completely possible to have incredible conversations by accident, it can also definitely be induced by a little effort. If you have never before had a great meaningful conversation, you wouldn’t know one when you see one. If you have never shared a deep conversation, when you have one, chances are, you might get inundated. Or let me put it this way — if you have had one of those before, you will be able to respond much better when you have one in the future.

And this is where friends come in — gather your friend, bring out your favourite drinks (and maybe a cupcake) and talk. Really talk. Ask the stupid questions. Ask the questions that came up when you tried digging on your own. Ask the questions that you always thought you should know the answers to, but aren’t fully sure. That’s where the best conversations lie.

Saudade (the love project) started like that. I was heartbroken in more ways than one, and the more I tried to deal with it, the more convinced I was that (a) everyone else knew some thing that I had completely missed the memo of, and (b) somehow the way I felt things was an aberration. So, trained in research methods, I decided to find out. I began to ask my friends questions like “when you say you feel hurt, what exactly does that feel like for you?” or “do you ever feel like you are hurt and that feels crappy and you want to just really wallow inside your damn warm blanket, but you also are feeling worse because you don’t want to be a victim and so you would much rather pretend like you weren’t hurt, but that only makes you more cranky” (btw, almost everyone said yes). Apart from the fact that I have absolutely fantastic friends who played along and answered my questions, I think these conversations allowed us a sneak peak into each others’ shoes in ways that we hadn’t had access to before while at the same time giving words to our experiences and helping us understand ourselves as well as the world better. I like to think of this process as building a database — next time someone said they were hurt, I not only understood better what it means by hurt, but also have a vocabulary/ image/ context in my head that allows me to respond to them better because I get that a little bit more. But there was also a more nuanced outcome that came from this conversation — a subtle sense of solidarity that gets formed when you know that someone else also hurts in ways that are similar if not the same as you; a sense of comfort that comes from knowing that what we feel is slightly more normal and universal than we care we remember.

3. Prepare

As a student of theatre, I am professionally trained to improvise. And thus for the longest time, I was way too comfortable in my ability to “wing it”. I mean, I know my crap, I know how to use it and how to turn things around, what can go wrong, right?

Then one day, without intending to, I told a whole room full of people I admired, that I essentially had no idea what I was doing in my life and thus single (this is a very mellow version of what really happened). I have had a whole variety of embarrassing moments, but this one really hit me. All I was expected to do was introduce myself with a very little twist in the question — how hard should that be? I introduce myself to people all the time! But I had been having a few bad days, I was tense about something, and at that point all of that was on my mind. So, in moment of panic for being put on the spot, that was the first thing my brain found. Now, I am sure most people’s brains probably do not have the same sadistic sense of humour that mine does (it is abnormally adept at always finding the most awkward thing to say with much panache), but since then I have been way more intentional about what I have most accessible in my head before I go to meet someone.

As far as possible, I try to keep at least a 30–40 min recess before and after I meet someone and use that time to “get into the zone”. I schedule a lot more time before I go for a professional meeting, but even generally I’d try to keep at least some space to gather my thoughts. When in a professional meeting, I actually have a format that I think in: what do I know about this person not just in terms of what they do, but also how they think, what they care about, what do I know about those topics, what do I want to know about those topics, and what questions I have for them. I also often actually practice the introductions, and what aspect of myself I am going to highlight in the conversation; like making sure I have revised what I know about that experience. I know this sounds really strange, I mean, duh, I know everything there is to know about me. But, at least I have found it to be immensely useful to make this information accessible — it frees up brainspace for me to actually process what the person is saying and ask intelligent questions than send my brain running trying to find that experience that might be relevant on the spot.

I am a lot less organised when I meet someone for a more casual conversation, but I still take the time to just gather my thoughts — What’s on my mind? What am I looking to get out of this? How am I feeling? To breathe, to neatly shelf out all the other thoughts that are boggling me and to ensure that I am fully present in that conversation and not trying to process something else there. It seems like an obvious thing, but at least for me, simply being intentional about it has been game-changing. It not only prevents me from doing something stupid, but also allows me the mental and emotional space to really take in whatever it is that I get in that conversation. And just generally, I think rituals help, particularly on bad days when that state of mind is harder to come by.

4. Ask good questions

This is the simplest one to learn, and you will probably find much better resources out there on how to do this better. The thumb rules I have with my questions (some of them are on the list because I have messed this up when I didn’t follow them) are:

  • Don’t ask what you could find on Google. Or, as a friend once told me, don’t ask because you are too lazy to find those answers on your own.
  • Open-ended questions. Always. Not just in how they are framed, but mostly just making sure that the other person always has the space to explain, that this doesn’t feel like either a a job interview or a trial. When in doubt, a “why do you think” and “what do you mean by that” are the safest options.
  • Don’t ask if you are not willing to really hear the answers or if you aren’t ready to hear with an open-mind.
  • When I go with a particular end in mind, I always let the other person know that in advance or at least in the beginning of the conversation, and give context to make sure they know why I am asking. This rule is also helpful when someone else has initiated a conversation with me — it helps the conversation feel like one rather than an interrogation, because the motive is consensual and no one has anything to prove.

5. Listen. Pay attention. Be present.

Probably the most overstated advice when it comes to conversations. With good reason.

The tips for this are classic, so I won’t get into it. But here’s something I know for sure: people know when you aren’t listening. When you aren’t present in that conversation. When you are not paying attention. Or when you are faking any of it. I am sure there are microexpressions and subtle cues that go into this, but regardless of what the reasons are, people know. And nothing pisses people off more. And rightly so! Almost none of us, given how we fill our calendars, do not have extra time lying around to spare. So if someone makes the effort to give you time and effort, it is basic manners to do all of this. Everyone does this differently, so figure out what works for you and how you can get yourself to listen, but there is tremendous merit to doing that. But this shouldn’t be a trick, this absolutely needs to be genuine; there is nothing more condescending than someone who pretends to listen but isn’t really. Celeste Headlee, who gives this absolutely brilliant TED talk about having better conversations, says this best: “There is no reason to learn how to show you’re paying attention if you are in fact paying attention”.

6. Invite them into sense-making

This is the one you don’t get very often (although the same sentiment is often brought up differently in many places), but in my experience, it is mostly this that gets people to open up. Like I have said before, vulnerability is different for different people — not just in how vulnerable they are willing to be, but also what vulnerability looks like for them. Some people would be perfectly okay sharing a personal anecdote, but won’t tell you how they feel, some would never tell you what they really think of something, whereas some others might tell you the lessons they have learnt from their experiences, but never share the experiences. Having put a lot of thought and work into what makes me vulnerable, I know what my style is and what my boundaries are, and that helps me quickly also know what the other’s style is and boundaries are, and that often that makes it really easy for me to navigate this, particularly because the topics I speak to people about are deeply personal. But even generally, being gentle enough for people to draw and define their boundaries, and allowing them the time and space to build the trust to open us is in my opinion, non-negotiable.

That being said, one of the most vulnerable things to do is to make sense of something with someone, because that encompasses all the forms of vulnerability — it requires you to accept that something doesn’t make sense to you while also allows someone else to being a part of that process, and thus, affecting you. Which is why, I have found that inviting someone to make sense of something is perhaps the most profound way to show that you are vulnerable, while allowing the other person to decide how and how much they would like to be vulnerable. They might decide to do so through their experiences or opinions or questions of their own.

At the same time though, this is also the easiest way to equalise the power in a conversation. Sure, there will always be a dynamic of slight inequality, which might have to do with experience, knowledge, age, stature or sometimes even extroversion and introversion. But, regardless of what it is in the beginning, a shared sense-making not just equalises it to a large extent by making space for that conversation to be useful for everyone involved. All of us have some questions about life, none of us have figured everything out, yet all of us know a little bit about something — inviting someone into sense-making establishes all of that as context, and builds meaning into the conversation.

The way I usually frame this is: This is what I have been thinking about (with a line or two about why I have been thinking about it, usually involving a concrete short anecdote that allows for empathy, and why my own prep about making my thoughts accessible helps), This is why I am talking to you about it (this is where the “what does the other person care about” homework comes handy),

And then opening up the space for them to comment with “what do you think about it”.


Originally published at tadbitlikelife.wordpress.com on October 26, 2017.