Eight questions for more interesting conversations

“Conversation is civilized speech. It is more purposeful than chatter; more humane than gossip; more intimate than debate. But it is an elusive ideal.”

John Armstrong, The Conversation.

All too often our verbal exchanges involve flippantly jumping from one topic to another, a smattering of small talk peppered with a rant here and there. And we’ve all been to that party or event where the mixture of humans results in below par conversation dynamics.


Conversation can truly begin to become dull when people are eventually resigned to ask, “So, what do you do?”

As if how one fills the day in exchange for money is an instant get-out-of-jail-free conversation card.

If the rapport is working between two people, they need never resort to such a question.

However, for those who find themselves stuck in a situation where the conversation flows like water in a desert yet still strive more, here are some options for diverting away from the dreaded boredom of “So, what do you do?”

1. What’s been the best part of your day so far? Was that unusual?

An easy one to start for those not willing to be super adventurous with conversation just yet. This is concrete, relatable and gets people talking about themselves, an all time favourite topic. It may require a few good follow up questions to maintain conversational rigour. 

2. Is there anything you know a lot about that most people don’t? 

Everyone who wants to make a decent living needs to specialise in something. This doesn’t mean they’ve spent years of their lives studying obsessively, for expert knowledge can come from simply following curiosity. This works better with people slightly older or those smart and witty enough to string you along regardless. A sense of humour also helps, as the last part is not at all to be taken seriously.

3. What is the ratio of the number of friends you have on Facebook and the number of contacts you regularly use in your phone?

Not everyone might want to discuss this openly, but again if they have a sense of humour and you are equally willing to divulge your own stats on this point, go for it. Could lead into a great conversation about “superficial connections of the modern age” though with the risk of sounding like someone born pre 1970.

4. What’s the prickliest piece of feedback you’ve ever had to swallow?

A tough one for sure, but this is a really great question for learning a lot about the other person. Not only from which piece of feedback they choose to mention but also how they swallowed it and how they’ve changed from that moment on.

5. What are you bored of?

Best used with someone you know somewhat or who you’ve noticed rolling their eyes and looking rather tired with the whole scenario. Haters love a good hate conversation or to lament about something that they feel is frightfully dull or dreadful.

6. Have you ever read something so fucking brilliant, it made you sad, because you’d never get to read it again for the first time?

A bit of a jazzier version of “Read any good books lately?” If you find that you have the answer in common, it’s sure to spark a deeper connection and lighten the conversation load from here onwards.

7. What’s the biggest epiphany you’ve had over the last year, in terms of attracting your ideal clients/customers/readers etc?

You need to know a little bit about what someone does in order for this question to work. If they have a part time job at the 7-11, the answer is probably not going to be riveting. This could fly if you are in a similar industry, you can tell the person really cares about the type of work they do or if you actually care about how they attract business. If you want to move away from work completely, replace ‘client’ with ‘lover.’

8. What’s one thing you DON’T know, for sure? 

This one I’ll leave for you to dissect.

So there you have it. Eight ways you can divert conversation and avoid being the one asking the most obvious question or drowning in small talk at your next event.

source behance.net

If you have success with any of these, I’d love to hear about it.

Inspiration and ideas for this piece came from Alexandra Franzen (www.alexandrafranzen.com) and John Armstrong at the Conversation.




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