The Art of Conversation:
I hate that title, it sounds horribly pretentious – and like every self help book out there – which, this isn't, evidently.
I should've put in parenthesis: Your crash course on learning how to listen to people.
Because truly, that's all it is.
I had to put words to this thing, as I've spent the last month involved in an absurd number of meetings – both in my personal and professional life. There's one detractor that I've taken away from these discussions, especially the virtual ones, and that is: Some of you are in a toxic relationship with speaking.
Which is fine, we've all been there – none of us came out of the womb with a speakerphone and a 'vote for me' pin stamped on our chests.
Nevertheless, I am going to discuss this (once, and only once):
A. Because this is a question I'm often asked.
B. Because I was fortunate enough to be around someone who taught me this at a very young age.
Yes that's right, I didn't come out of the womb with a speakerphone either.
These things are taught, practiced, learned – rinse and repeat (this is the secret to basically everything in life by the way – barring strange circumstances, of course).
Okay okay, get to the point – here it goes:
When you're speaking with someone – know that this is not a monologue.
You're probably going “well, no duh????”
I know that it seems obvious, but I don't think it sinks in for many of us – not really.
You are not standing in front of the mirror speaking to your reflection, or to your journal, or your therapist – you are speaking to a living, breathing, human being (one who likely isn't being paid to tolerate your company, they're doing so because they either have to – or they'd like to...If it's the latter, let's keep them motivated to keep doing so).
The thing about living, breathing, human beings – especially in 2024 – is that our attention spans are finite (highly finite). In fact, if you've even made it this far, kudos to you.
When I'm speaking to people, I always have an invisible stopwatch ticking away in my head – I'm timing myself (not in an anxious way) – in a “how much reasonable space have I taken up in this conversation” way.
Make sense?
If you ever find yourself leading a conversation wherein you've been speaking for 10 minutes straight -without carving out an opportunity for the other party to jump in – we've made a blunder. You are not on a stage, this is not an audience – these are your partners, your friends, your colleagues.
Not only should you be mindful of how much time and space you're taking up in a conversation, you also have the responsibility of carving out pathways for the other person to jump in (it's common courtesy).
Think about it like this:
The conversation is a set of crayons, there is only one set, one piece of paper, and one drawing to fill out – but there are two of you, and you're both vying over the same coloured crayons (you'd have to, this colour scheme needs to be cohesive after all – we can't go around picking out weird colours all willy nilly).
It's your turn to colour first, you pick up the yellow crayon – and kick off the process. While it may be awfully easy for you to get lost in this drawing, thus, transcending the presence of time and space – you have an obligation not to do so. Because your friend is just sitting there, staring at the side of your face – in good faith – hoping they'll get their turn soon.
Let's say you are mindful of the time – you spend two minutes colouring in the circle, and not a second longer. Would you then sit there, holding onto the yellow crayon, and staring at your friend's face?
No – you ought to lean in – pass the crayon along, and maybe say something along the lines of:
“here you go, you can do whatever you'd like but I left this white space here for you specifically, so it might be easier to continue.”
And so it goes with conversations.
The person on the other side may be incredibly confident, and capable of carving out these spaces for themselves – or they may be shy / more reserved, silently hoping you'll provide them some sort of an opening to share their thoughts. You can bring humour into it, that helps sometimes. When I'm talking to candidates, for example – and I'm describing anything dry /tangential (i.e total compensation, or work culture) – I pause every now and then, and say something along the lines of:
“I know this is a lot of information! I'm going to pause here to make room for any questions you might have about x,y,z that I've shared?”
or
“This is a lot to absorb, is everything alright for you so far? Is it making sense or is there something I might be able to provide clarity on before we continue? Thank you for baring with me, by the way, I know this is dense content”
I'm doing a few things things here:
A. I'm reflecting the person's experience back to them verbally (they already know this information is dry / a lot, they now feel like I know the same thing as them – like we're on the same wavelength – this brings a certain level of comfort without the other person realizing that it's even happening, it's subtle).
B. I'm creating spaces to stimulate the person on the other side of the conversation – thus, (hopefully) keeping them engaged.
C. I'm encouraging the person to jump into these spaces – this is what makes a conversation a conversation, rather than a monologue.
D. Most importantly: I'm talking to the person, not at the person.
So – let's do a quick recap: Mental timer, space carving, crayon sharing – what's left?
People reading.
This one is tricky, it takes a lot of practice, and it's somewhat controversial – so I'll do my level best to be careful while addressing it.
Let's start with a basic principle:
Most people love being heard – this is why we pay hundreds of dollars to therapists, this is why every friend group has that one timid / shy friend, this is why folks form parasocial relationships with celebrities, and this is also the secret to every great conversation.
When I'm speaking with people: They are the centre of my metaphorical universe.
But there's a trick to executing this efficiently, because if it's too obvious – people will know, and the magic fades. You need to fine tune your approach, and subtlety is key. If you can remember things about people, this part becomes infinitely easier. For example, if I'm seeing a family member post holiday season, I may say something along the lines of:
“I remember last time I saw you, you were telling me about that frustrating admissions essay! What happened there?! I've been so curious!!”
Am I particularly riveted by / invested in this admissions essay? No.
Is the person on the other side likely still stressed out about it – and just looking for a good opportunity to vent? Yes. I'm tapping into that, and allowing them to carry the rest of the conversation.
The discussion will now centre around their experiences, with me throwing in a :
“When I was submitting my admissions essay a few years ago – they had a fixed topic, I wonder if that's changed?”
&
“Admissions essays are so silly, sometimes I feel like the whole system is rigged, and the world is on fire – the war for example...”
Again – I've done my homework. I'm not mentioning the war just for the sake of keeping the conversation going. I already know that this is a person that's highly politically charged, and that they have very strong opinions on warfare – this creates yet another opportunity for them to dive in and share their perspective.
Can you see how we're keeping the conversation flowing, while simultaneously centring the other party and their interests? These are universal topics, so they may not realize it – but here's the thing: I've never submitted an admissions essay in my life (I've observed others doing so). And I'm not nearly as politically charged as this person is, but I keep up with the news everyday.
“But that's deception!!!!”
No – that's a conversation.
What if you don't know this person? What if it's someone brand new, and you don't have fun facts to refer back to?
Then you're going to do a little improv, and we're going to start a knitting project.
Engage in the conversation with open ended questions, the moment this person reveals something about themselves that's niche – we're going to latch onto that, that's our yarn, and our base for the rest of this oddly shaped glove.
“The traffic in this city is a nightmare. So, what brings you to Toronto?”
“My cousin's getting married this summer – so I'm here for that...”
“No way! My friend is getting married in the summer too, it'll be a busy season. Is your venue also in xx by chance?”
Not likely.
“No it's actually in xx – I've never been...”
“I think I've heard of it! It should be relatively close to you if you're staying here – weddings are always tricky though, does your cousin have a registry going?”
Not an open ended question, but one that doesn't need to be open ended because everyone and their mother is dying to bitch about the nuances of gift registries.
See how we knit a conversation surrounding this person's upcoming experience? We're tapping into what we're guessing they may be anxious about. We're asking questions that are opening spaces for this person to divulge more information.
Honestly folks, if I actually do a deep dive on this one, I'll be writing my way into oblivion. But I think these basics should be enough to get you started.
I hope this helps, and I hope you use these ideas wisely – and with good intent.
Keep in mind, that we've all had these tactics used on us at one point or another, I'm just teaching you how to be on the other side (it's for the greater good) – because if I have to sit in another meeting where I'm being talked at for nearly half an hour, I will do bad bad things.