July 8, 2020

How to have better conversations — things I’ve learned from being socially awkward

Believe it or not, I was (and still am) socially awkward. Not just the guy that has no idea what to say or how to continue conversations even when he knows he should but the guy that saunters up to groups of people at conferences, listens in on conversations and then slinks away when he does not find a topic to talk about.

On a side note, conferences are really not my favourite thing even though I do get a lot out of the speeches and workshops — I think it’s mostly because I have never been a very good networker and I think that can be traced back to my perception of networking which was fake and ‘salesman-like’. Part of it is probably the fact that I’m an introvert although I’m being much more aware of the stories and scripts that I tell myself these days to make sure that I’m not pigeonholing myself into something that I can easily change.

Over time, through different courses, books and articles, I’ve learned that there are ways to have better conversations. Ways to have longer and deeper conversations. Ways to make things seem natural even if you just met someone for the first time.

Prepare in advance

Perhaps the easiest way to have better conversations is to prepare well in advance of any anticipated questions. If you know you are going to be asked about the weekend, do something interesting, or have a story for what you did on the weekend. Brainstorm different ideas in advance (well, it’s not exactly brainstorming but think of what you did in the past and figure out how to put your own spin on it to make it interesting). Maybe all you did on the weekend is read and write (okay, that’s my weekend) but I also worked on the cover for my new book and sent it out to a few friends to see what they think.

Enthusiasm makes anything interesting

Once, when I was invited to a fellow Toastmaster club, I met a number of individuals who were young, ambitious and dedicated like me. I didn’t know who they were but they had just seen me evaluate a speech and were certainly impressed. When they introduced themselves to me, we went through the usual niceties and I didn’t think anything of it but I suppose they were better networkers than me because one of them asked for my business card. I presented my card, at the time, I was with Deloitte, and one of them piped up and said “whoa you have a business card, can I have one too?” and many more chimed in. I was pleasantly surprised that people would want my business card and I will always remember that enthusiasm for business cards.

Think about the last time that you may have had a conversation with someone about a topic that you had no clue about. I’m willing to bet that if they showed incredible enthusiasm, passion and background on the subject, it made you care about it much more than someone that drolls on about their pets or vacation (although those can be great conversation topics with enthusiastic emphasis).

Pivot if appropriate

Whenever I get into the office on Mondays, I dread the question “what did you do this past weekend?” I dread it because I’m a fairly boring person and I am really not up to much on the weekend. So I say “oh not much” and the conversation either ends there or I redirect the question back to them if they are nice enough to stick around and continue talking with me. Lately though, I’ve learned that it is okay to reframe the questions into something that I can speak about.

For example:

“Hey, what were you up to this past weekend?”
“Not too much….crickets
“Okay, bye”


“Hey, what were you up to this past weekend, anything fun?”
“Not really, but two weeks ago I was in a badminton tournament where my friends and I placed 2nd in the tournament”
“Oh awesome, tell me about the tournament”
“Yeah it was an inter-club badminton tournament with clubs in Edmonton”
“Cool, you must play a lot of badminton”

See how the conversation changed from one weekend to any weekend? You can do the same with just about any subject really:

  • “Hey are you planning to go anywhere this Christmas?” -> “Actually, I had this big trip to Japan where I went to Tokyo, Osaka and Hokkaido over the summer that I used up all my vacation for”
  • “How are things with the home renovation?” -> “Oh I finished with the renovations a while ago, now I’m onto building out my library — I just got a rare first edition of Curious George last week”

Giving and finding hooks

Perhaps one of my favourite tips of all — having a good conversation is going with the ebbs and flows of the subject at hand. Maybe you start talking about politics and how Trump is doing as president but then you switch into Canadian politics, then maple syrup, then hockey, and then the crazy Canadian winters. The conversation switches because of these ‘hooks’ that are in conversations. Let me give you an example:

“Hey, what did you do this past weekend?”
“I went out to a gun club with my girlfriend and we went hunting for animals. We actually ended up shooting and hauling back a small deer that we are going to butcher up and make some sausages with”

The hooks in that previous conversation were, with follow on questions:

  • Gun club -> Oh I didn’t know you shot guns as a hobby — how long have you been doing that for?
  • Girlfriend -> Oh wow, your girlfriend is into guns, must be serious?
  • Hunting for animals -> Aren’t you vegan, why did you go hunting?
  • Sausages -> You know how to make sausages? Do you make sausages all the time?

These hooks help conversation participants to have something else to talk about, if they do not want to talk about the current subject at hand. And the way to get out of a conversation you don’t want is to provide the other person with more ‘hooks’ if you do not like guns, sausages, hunting for animals or relationships. Truth be told, I have used this technique in many of my conversations but I didn’t know how to put it into exact words until I took a course by Patrick King.

What are some things that you do to help have better conversations? Ask better questions? Approach things with curiousity? Remember that everyone that you meet can teach you something?

About the author:

Wang is a management consultant, self-published author, Distinguished Toastmaster, co-host of a podcast, Udemy teacher, former Uber driver and all around hustler. He is also obsessed about books and he reads books so that you don’t have to. Want a list of Wang’s top ten formative books in his life and career? Interested in book summaries and recommendations every month? Subscribe to Wang’s e-mail newsletter!

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