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,

What does it mean to say “me too”?

Me too.

Despite all my skepticism for social media campaigns, this one felt important to participate in. To acknowledge the fact that I have struggled to say “me too” in the past, and never quite known how to.

9 years ago, a security guard groped me and pinned me against the wall before I could run away. Accordingly to the “morality” that had then been imposed on me, I had technically been somewhere where I shouldn’t have been, at a time I shouldn’t have been at with someone I shouldn’t have been there at. A fact that the guard pointed out before he used that situation to find me alone, and all of us, in that fear, had given in. I did not remember the face of the guard: I was in shock.

That night, I told one of my closest friends I had been molested. He was standing on the step lower than the one I was standing on, still taller than me, and with his body suddenly tightened, he asked me kindly: “what exactly happened?”. I described the event to him, still shaken up. “Oh! I thought it was a lot more when you said molestation. Thank God! That was just groping. I am sorry that happened to you, but it happens to women all the time. You will be fine”, he said. I liked to believe then that he was trying to make me feel better, and swallowed the “don’t be too dramatic, you will be fine” suggestion he gave, and shut up.

Thankfully, I had other friends who did not feel the same way. The friend that I was with remembered the face of the security guard and they complained. The guard was fired, and the issue was closed, right?

A gnawing feeling followed me though. Although still not sure of the nuances it entailed, I still called myself a feminist and had been for a while. When this incident, I was ashamed, more than anything else – this wasn’t how a feminist was supposed to react, right? The story of what happened was muddled with so many other stories that I wasn’t ready to own up to yet. I wasn’t ready to tell the story of why I was where I was. I didn’t want people to know that I was actually a coward who had not come forward to take action. I wasn’t even sure this was molestation (“groping”, as I had been corrected, remember), and I liked to believe I was strong for not letting that incident be important. I liked to believe I had “moved on”, because at 18, that’s the version of the stories I had heard.

A little more than a year later, I did tell the story though. On stage, as a part of a play. Something about telling the story again and again made me feel like I had owned up to it. Another friend came up to me after one of my performances and said “it was such a nice light-hearted play. You had to add your melodrama, no? Why can’t you deal with your crap in your own time?”. He then laughed. “Attention seeking” and “drama-queen” was squeezed in somewhere in all the mockery that followed. Guessing this was yet another social memo I had missed, talking about it felt less cathartic and right. There had been women who had hugged me for that piece, but it was this voice that continued to pierce through. I decided to “move on” again and not talk about it. After all, it wasn’t a big deal, being dramatic wasn’t cool and this happened to everyone all the time, right?

I grew up, learnt how to say no more strongly and fiercely, and said so in the coming years. I evolved to find friends who didn’t think there was something wrong with it. I forgot this had happened and assumed that meant that I had “dealt” with it, right?Or so I thought until a few years ago. It was the day after my birthday, and I intended to recover from the last night by treating myself to a late morning and a beautiful brunch. I was woken up instead, early on a Saturday morning, by a friend calling me to tell me that he had been molested. By another male friend. Who I didn’t know was in the process of coming out. As I heard his side of the story of impulsive lack of control that he deeply regretted, sitting with all the other male friends who were present when this had happened, I struggled to find my objectivity and “balanced view” – how does one begin to reconcile the images of the “kind of people who do this kind of stuff” with someone I deeply respected? I was driving the friend who had been molested back to his house when he, still shaking, looked at me baffled and mumbled, “this wasn’t even a big deal, women go through much worse. I am terrified for my sister who goes through this all the time. I don’t even know why I am so affected! I just don’t know how I am supposed to respond as a man”. I tried to push behind all the triggers that were pounding at me then – all the other chauvinist comments he had made in the past that had pissed me off, and all the layers to what he was saying right now. I don’t remember what I told him. I knew I had to tell him he had every right to speak up, to feel everything he was feeling, but given how I had responded in the past, I remember feeling hypocritical. I remember trying to find, once again, the right language to help him describe what had happened – (“grabbed?” “squeezed?” “groped?”).

I work with stories, and thus, by default, I am hyper conscious about how we tell our stories: the language we use, the images we paint, and what that means in how we understand the world. Recently, as I drafted this story as a part of another speech that I was writing, I struggled to find the right words. On one hand, my speech needed to be powerful, and there were certain ways that stories like that become powerful; I had learnt enough of that. At the same time, I also needed to make sure I wasn’t painting myself as a “victim” – I needed to retain my credibility. I remember poring over the words again and again – would saying “groping” be too graphic? “Molestated” sounded vague enough but powerful enough. Am I coming across as less of a “feminist”? Is it too “dramatic”? And as I pondered over what all of this meant, it also hit me that for such a long time,I was so busy with not being the victim, so concerned with making sure the story fit into my larger narrative, that I hadn’t given myself the time to hurt, and thus, heal. I hadn’t forgiven myself for not remembering the man’s face. For not being careful enough. For not finding the courage to complain. I mean, if I had been scared then, couldn’t it be possible that I wasn’t as courageous as I thought I was? Every time I had visited what had happened, I had found ways to make myself worse, a skill that they teach the girls so damn well.

Like I said, I work with stories, and in working with people on drafting impactful stories and building toolkits for people to do so, I find myself coming back to these questions again and again. How do we narrate these stories of what we go through? What does it mean to share this, in a context where we know “powerful” to be only in a certain way? What happens when what is powerful isn’t that easily true for the self (not just in terms of what happened, but also how one tells that story) or worse, vice versa? What does it mean to be a “victim” of sexual assault, across the spectrum of that (I cringe as I type that)? Can I not be a victim and still allow myself to hurt and grieve and heal (and cope)? Can I allow myself to be “a victim” and still be empowered? Does changing the language from “victim” to “survivor” help, or do the connotations follow? How can I forgive for my healing, but still be angry enough? When does this constant portrayal of “powerful” stories that look and sound and end only one way normalise it, and what does that normalisation look like?

I find myself struggling with these questions again as I type “me too” into my facebook box (which I must also say, I did do, for I think it is also important our fact-obsessed culture to “empirically” see what this is): What does it mean to say “me too” ? What does it mean when our entire timeline “outs” themselves as survivors? What are nuances of the normalisation that it beings about? What kind of solidarity does it stand for? Who gets included and excluded in this narrative? What does it do to how I, too, experience it and thus, how I, too, respond to it?

Perspectives, anyone?
Jayati Doshi
Oct 16, 2017. 1.12 pm EST

I was craving kindness today.

I think there are themes to our lives.

My mum told me that if you are in touch with your body well enough, your cravings tell you what you really need right now. Not the cravings for chocolate and maggi, she’d remind me, if you get your body used to the good healthy diet, it will truly crave the healthier things you need.

I tried this once. I don’t know about weight loss, but I remember my skin glowed at the end of it. And my body craved a lot of fruits – bursts of nutrients that scatter through your body, like the tickles of a child’s fingers – the kind of good that’s subtle in its presence.

I think it is the same with our lives and our mental and emotional and spiritual healths. I think our bodies and deeper parts of our minds know what we need, and we crave that. Cravings we lose touch with when we get too wrapped up in our calendars.

I have been craving kindness. I didn’t know that.

More than anything, she’s awfully kind, a friend, A, said a few days ago as she introduced me to someone for work. A strange trait to point out in the middle of a professional meeting perhaps. But K (the third person in the room) and I smiled. That’s an important characteristic to spell out in introductions, she chimed.

Despite all the long list of incredible ideas that meeting gave me, this one, for some reason, stayed. If I were being introduced to someone, I aspired, this is how I would like to be introduced.

I met this “kind” person a few days later. I don’t know what left me warm at the end of the meeting – the great conversation we had, the kindness she exuded or the fact that I was suddenly more aware of it because it had been pointed out?

Suddenly I started to see kind everywhere. In the meetings I’ve had these past few days, with people at varying degrees of high on my “admired” list, I am beginning to see how “kind” has perhaps been such an essential measure towards the admiration.

I told this to another friend, who had just introduced me to someone else with a note of he is very, very kind. We then spoke about a bunch of things before we circled back to the kindness I was suddenly so aware of. He called it humilityThat too, I said, suddenly feeling the need to justify, but kindness feels like it’s so much more than that. Empathy? Compassion? Generosity? All that, but not quite. I didn’t have any more ways to describe this qualitative difference in words; I might bode fairly well with words, but my brain thinks in the form of images: pictures. and smells. and sounds. and feel. and kindness, had its own catalogue entries in my senses. And I didn’t know how to curate that to explain.

I met the “very, very kind” person today. I was perhaps looking too hard for it.

I saw that kindness today. There’s a way that kindness touches you that makes something in your body relax. You know that feeling you get when you are meditating, and you can feel your body release tensions as you pay attention to it – something like that. Attention, like kindness, is in short supply lately. I wonder if there’s a connection.

I think I finally know what the term “kind eyes” means: it is the way eyes expand and pupils dilate because someone is interested in what you are saying, because they are taking in and considering it gently and patiently, not just without judgment, but with a sense of calm curiosity with an open heart, a light that shines from that opening.

And as I walked away, carrying this lightness and becoming aware of it at the same time, I started to think of this theme around me that had shaped up over the past few weeks: I was craving kindness, my source of it within myself slowly leaking away as I piled my jenga of unfinished things higher and higher, waiting for it to fall.


I didn’t know where to find the kindness to replenish my supply from.

The type-A me poked her head out as I thought that – she had never gotten along too well with the me that liked to think about things; the two of them have a classic product vs. process struggle with their values. So, I took my book out and scribbled, letting the both of them speak. And now that they are done unloading all that pent-up-unkindness, they are slightly more accommodating of each other.

I then showed them the images I had collected from last few weeks: above all, we are kind, I reminded them. Gave them a product and process to work on.  A prescription for a diet of fruits, in some ways.

Jayati Doshi
4th Oct, 2017. 5.12pm