How to have better (and meaningful) conversations.

One of the questions I get asked most commonly when I talk about my work is “how do you get people to tell you all these intimate stories of their lives?”. Umm, I don’t really know. I don’t have a strategy. I just love talking to people and have been doing this for really long, so I hadn’t really formally thought about it. Then recently, I found myself reading and listening about conversations, trying to learn from the best conversationists I know, and analysing what I do, realising that there were indeed some very specific steps I had followed that worked.

Now, I am by no means an expert, but over the years with conversations being integral to the work I do, I have come to develop 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. Kio Stark, who talks about stranger interactions, describes this pleasure of conversations beautifully: “This is almost poetic. These were really profound experiences. They were unexpected pleasures. They were genuine emotional connections. They were liberating moments”.

So, I wanted to write down what I learnt, also as an invite for people to experience the joys of it.


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 about anyone:

  1. Do your homework – get your foundation right

“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 responding to 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; aka 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 consciously 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 self-work 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 friends, 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. And having them with people you share some history with are the best ways to learn about the dos and don’ts of navigating these.


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. With the unintended outcome being that it helped 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 outside of myself 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. After I got out, I dissected this: 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. And that has made a world of a difference.


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. It not only makes sure that I can make the most of the meeting, but also makes it possible for me to be 100% present at every meeting. When in a professional meeting, I actually have a standard set of questions that I make notes on: (a) what do I know about this person – not just in terms of what they do, but also how they think, (b) what they care about, (c) what do I know about those topics, (d) what do I want to know about those topics, and (e) what questions I have for them. I also often actually practice the introductions, or at least think about 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 readily accessible in my brain – it frees up brainspace for me to actually process what the person is saying and making all the relevant things I “know” only a few connections away from being found.


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? Taking the time to breathe. To neatly shelf out all the other thoughts that are boggling me. 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 a mutually beneficial 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. They know 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 how, people always know. And nothing pisses people off more. And rightly so! Almost none of us, given how we fill our calendars, 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 tip 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 elsewhere, 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.


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. But when you open up the space to do this, it is the one absolute surefire way to have a fantastic conversation that people remember.

The way I usually frame this in a conversation 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?”.


Almost always, the response to that includes them telling you what they know, and then also framing open-ended questions they might have – and that makes a continued conversation so much easier! Plus, in my own romantic way, I like to think that doing this allows me to connect the dots between the people I meet and the people they have known, while also learning more about the world in the process. I believe that this has not only made my conversations more meaningful and how I learnt so much of what I know through them, but has also brought me much much more belonging into the world. Just something about this process makes it easy to walk around with a curiosity mindset, to constantly learn, and while doing that, contribute to a collective sense-making about the strange world we live in, while also opening up possibilities in places and ways we did not know existed.  Also, I make notes about this, which are systematically organised and thus accessible (I use the time after a meeting to do this, or get back to it at the end of the day).

7. Follow up

Again, this part is obvious – write a thank you note, send them the resources you say you would send, and keep writing to them once in a while to stay in their memories.


Here’s how I learnt to do it better: I write a genuine thank you note, also bringing in little snippets (a line or two) about what I learnt in that conversation – this not only helps me demonstrate that I listened and makes them feel good about themselves (and everyone keeps an email/ message that makes them feel good about themselves), but gives them a concrete context to remember me by. This context I have found super useful in keeping in touch: Say I learnt a really interesting perspective or metaphor for an issue from person A, and I use it in conversation with person B – not only does it make person B trust me more because they now know that I actually remember and listen and quote other people, but also becomes a good reason for me to write to person A and say “I was telling someone about what you said, and they said this, and I thought of you and would like you to know”, opening up more space for conversations. Moreover, this context also becomes a reason they get in touch with me – I often receive messages and emails from people because they were reminded of something I said, and a conversation thus ensues. And, of course, while doing that, I only learn more in the process. It’s a win-win-win.


Mostly though…

(and you might already know this), conversations often do go wrong. All of us have some of those stories to share. I believe strongly that the solution to that isn’t less conversation, but more, while learning through it. To be able to laugh at that and learn from that, cliche as that sounds. At the end of the day, it is all about getting better, right? (Without, perhaps, taking ourselves too seriously!)


Hope that helps! Would love to hear people’s thoughts on this, and/or how it goes when they do try it out!

Many good conversations to you,

My life, on a google doc

We walked back from the Charles river, our impending romantic relationship apparent through occasional brushing of our hands. The boy had already lost track of the names of the people in my life I had introduced to him through my stories that night. There are too many people in your life, he complained. The aww-inducing thought underlying that complaint came right after: how do I know where I lie in your life?

Now, anyone who knows me knows that I am an obsessive categoriser. It is only natural then that all the people in my life are neatly divided into categories based on the roles they play in my life. The task then, was to now make these categories more concrete for the boy. As usual, Google had the answers.

Imagine my life were a story being written in real time on a Google doc, I told him. It’s a detailed narrative, filled with much details and anecdotes, the voice evolving as I grow.

This Google doc is publicly visible; my story, written with pseudonyms, is an open book. Anyone who wants to put the effort of looking up the url and opening it can read what is written in it.

Some people get commenting privileges for parts of this story. They can leave their thoughts, and I will look at it in my own time, and choose what I want to do with them, how much of those I take seriously. Some comments, obviously, are taken more seriously than the others.

Some people, the ones in my intimate circle, get editing privileges. They, each with their own voice, can make changes to my story, helping me make more coherent sense. These edits show up as suggestions, allowing me to keep the ones that make sense to me. This explains why my story can feel multi-hued at times, there are several eyes editing it with different linguistic aesthetics.

Someday, I hope to find someone who can write this story with me. That person will have edit without suggestions privileges, I tell him, blushing.
The boy never moved past commenting privileges, and slowly he stopped even viewing the document. However, the metaphor has stayed on; it’s helped me define roles and boundaries and made my life easy. I wrote to a friend recently complaining to her about an email feedback I received that had left me upset. Is this feedback a comment or an edit, she asked. One line, putting the distinction into perspective, putting the ownership of my Google doc back into my hands.

Jayati Doshi
14th June, 2017

Status: It’s Complicated

Baby, i’m not complicated.
i’m the intricate art
of layers
of chaos
collected from our complex world
as i embrace it
with open arms
naked body
curious soul
letting it consume me,
and through it,

i’m not the complicated that you mean, the abstruse
It might just be your baffling you project, darling.
i am the elaborate beauty that has taken time to build
with meticulous interaction with the world
the esoteric mess of inclusiveness
of perspectives
a center to multiple viewpoints
that shines like sunshine.

i’m not complicated, love
i am work
in progress
reorganising the world
into inviting categories of meaning
by being embedded in it.

or maybe i am
a bundle of paradoxes
of mistakes that consciously lead to wisdom.
if that’s what that word means, anyway.
i simply no longer
use that as a disclaimer
to my being.


Jayati Doshi
15th Oct, 2016. 9.33 am EST.

Us. Within our rhythms.

We take our circumstances and beliefs, and find our choices within.
You, to the best of your ability, slightly enchanted by your needs of the moment.
Me, to the best of mine, finding my way amidst the sea of my wishes.
We, dancing our moves through this stage full of improvisers, occasionally swinging together.
Organising our circumstances into stories. 
Somehow, through it all, orchestrating the rhythm that tunes our shared circumstance. 


Jayati Doshi
July 11, 2016. 4.14 pm

The piece about pieces


I spend my days collecting pieces
to make up my world
and trying to piece them together

with childlike curiosity
for meaning-making

I try and try,
finding the fit,
as closely as I can

And then I draw over them
intricate patterns,
with my schemas

There are some patches
Where the meaning is coming off;
But I draw on naked land, anyway

Pretty, shabby, beautiful, messy
incoherent, abstract, connected, meaningful
my little world of mismatched pieces

Some days it falls apart
the pieces I put together
my process, too much,

Today I felt you come around,
your hands too real, too coarse for my jigsaw,
but a semblance, a delusion of my world being held

while I start it piece it back again.

The making of the globe

Jayati Doshi
4th March, 2016. 8.02 pm