Oh I'm Sorry, Am I Boring You?

Stop putting everyone to sleep with the same boring small talk

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Happy Monday

  • Impending bowel movement

  • Eye bags full

  • Lukewarm Regards in hand

How good. Let’s begin.

Do you ever worry that everything you’re saying is plain dribble? That you’re putting that poor soul across the water cooler to sleep? 

Woes like this are part and parcel of the office experience, and when your average coworker is 45, divorced, and losing the custody battle, the prospect of an interesting conversation seems nearly impossible.

Try finding common ground with the receptionist turned Weight Watchers ambassador.

“Morning Dianne, how’s the thyroid this morning?”

Queue the crickets…

Here are three strategies for more interesting conversations that hopefully won’t result in Weight Watchers cease and desist.

Meet Mark

He’s just turned 50, was born and raised in Sydney, and cycles to work. He’s got a beautiful little girl and a not-so-beautiful (ginger) boy. 

He works in middle management.   

Mark represents your stock standard middle-of-the-road manager. And we’re guessing you two have fuck all in common, making him the perfect test dummy for the following strategies. 

Peel the Onion

To peel the onion is to ask ‘why’ questions that get people talking about what they value.

Let’s say you meet Mark at a conference and ask where he’s from. Standard small talk procedure. He says Sydney. For some reason, most will follow up with something like “Is it nice there”. 

Do you think Mark thought to himself...

“This Sydney place is an absolute dump, I think I’m going to settle down and start a family here”.

Middle management Mark

No. 

What we don’t know is why he’s chosen Sydney. There’s likely a multitude of reasons, each sparking further conversation that he actually cares about. 

It’s a more interesting question for him to answer and invites elaboration, allowing us to take the conversation beyond standard small talk.

Fun Questions

When we converse it often feels like there’s a set of constraints dictating what we can or cannot talk about. It’s half the reason you’re incessantly questioned about your weekend or holiday plans, work projects, and what you’ve got for lunch. 

Interesting conversation starts by removing the constraint of having to be realistic. These shackles don’t exist and do not need to be abided by. You aren't obliged to ask Dianne about the lady shake she’s brought lunch. 

Fun questions equal fun conversations.

Let’s pretend you learn about Mark’s love for cycling. Get creative with what you ask him. 

  1. “Mark, if you could cycle anywhere in the world where would it be” 

  2. “If a novice like myself wanted to get into cycling, where would you recommend I start? 

  3. “Mark, if you were a professional cyclist what would be your steroid of choice?” 

Yes, these questions sound ridiculous, and yes, you couldn’t care less about cycling, but Mark does, and if he’s a happy chappy, then so are we.

Look how happy he is

Mirroring

Mirror the last or a select three words back to your coworker. It’s literally that simple. 

Why is it effective? 

We fear what’s different and are drawn to what’s similar. When we mirror correctly, we insinuate similarity, which facilitates bonding. So you can use mirrors strategically to keep people talking, encourage others to empathize with you, and build rapport. 

You’ll be surprised how effective they are. 

That’s it, cya 👋