Making small talk with the big boss
Stuck in a long elevator ride with a superior? Here are a few tips to avoid awkward silences.
by Kelvin Kao · CNA · JoinMany years ago, as a bright-eyed intern eager to make my mark, I found myself trapped in one of the most dreaded workplace situations: A long elevator ride with a superior.
“Good morning,” my supervisor said as the doors closed.
“Morning!” I responded a little too enthusiastically, immediately regretting the overly chipper, high-pitched tone I tend to have when I’m nervous.
And then … silence.
The elevator hummed quietly. I stared straight ahead. My palms were sweaty, knees weak, arms heavy.
“So,” she said, breaking the silence, “how are you finding things so far?”
My brain went into overdrive. Should I sound casual? Enthusiastic? Cool but competent?
I cleared my throat and opted for a shaky “Yeah, things are great!”
Before I could stop myself, I added: “Really learning a lot about, uh, you know, email … and stuff.”
My supervisor smiled, polite but slightly puzzled. “That’s good. Email’s important, for sure.”
I wished I could’ve dug a hole in the floor of the elevator right there and buried my face, never to resurface until someone kindly emailed me that the coast was clear.
“Email and stuff”? Why did I say that?
Instead, I had to stand there for what felt like an eternity, mutely begging the elevator to go faster.
When the doors finally opened at the 28th floor, I practically leapt out and mumbled something about getting back to an analytics report.
Years on, I still think about that elevator ride from time to time and shudder in shame.
Talking to your bosses can be hard. Throughout most of my career, I struggled in making conversation with my superiors.
What should I say? What can I say?
Now that I’m on the other side of the boss-subordinate divide, I’ve gained some perspective and insight on how to better bridge this awkward gap.
To begin, I’m not a fan of scripted dialogues or robotic pleasantries. You don’t want to sound like someone who has read one too many LinkedIn articles on How to Build Rapport with Your Manager in 60 Seconds.
That doesn’t mean that you should wing it either. You need a strategy.
So, for those who dread those spontaneous run-ins with your boss, allow me to share a few tips for how to navigate that tricky situation when you find yourself in the same elevator as your boss — or worse, seated right next to them at the company dinner.
1. KEEP IT LIGHT AND BREEZY
First rule of small talk: It should be small.
Think of it as a light snack, something you can grab and go.
Nobody wants to feel like they’ve been ambushed with an impromptu Joe Rogan podcast while they’re getting their coffee. Keep it simple and digestible.
“So, what’s the latest show you’ve been watching?” or “What did you do on your weekend?”
These are harmless topics. They don’t ask for commitment, but they keep the dialogue moving.
No one is expecting anything deep or meaningful, just a little surface banter to fill the void.
2. GRUMBLE TOGETHER
Ah, the joy of shared misery.
Few things bond humans faster than a mutual complaint. The toilet bidet hose that is constantly bursting in the middle of the day? That client that keeps insisting on making the copy “pop”? Perfect fodder for mutual grumbling.
Complaining, when done sparingly, is conversational WD-40. It loosens things up, makes everyone feel like they're in this together and, most importantly, shows that you’re human.
Just don’t get too negative and come across like you are a ticking time bomb of toxicity.
"Can you believe the bidet became an indoor fountain again for the fourth time in three weeks?" This would be simple, effective and guaranteed to get a chuckle — or at least a nod of agreement. It’s a soft entry into building camaraderie.
3. READ THE ROOM
Sometimes the best way to make conversation is not to make any.
Bosses are human as well and there are times when they might have a lot on their minds.
Be observant. If they look terse or distant that day, maybe now is not the best time to ask for their prediction on who would emerge the winning couple in the South Korean reality show Single’s Inferno.
You’ll get your chance — there is a time and place for everything.
4. JOKE'S ON YOU
Humour can disarm even the most intimidating of bosses, but it’s a tricky tool to wield. The fine line between amusing and inappropriate is thinner than the Wi-Fi signal in the office bathroom.
Stick to observational humour or self-deprecation. Almost everyone loves people who don’t take themselves too seriously. It makes you approachable and, overall, a fun hang.
Just remember to keep the humour light and non-offensive so that it doesn’t become another situation that your boss has to handle.
5. EXIT STRATEGY
Perhaps the most overlooked part of small talk is knowing when to stop.
You don’t want to be that person droning on while your boss is scanning for exit cues around the office like it’s an escape room.
Once you’ve exchanged a few pleasantries, complimented his latest sneaker acquisition (sincerely, of course), or commiserated over how Monday mornings are the worst — bow out gracefully.
“Well, I better not hold you up. See you in the meeting later!” This would be smooth, polite and respectful of their time. You’ve engaged, you’ve connected, and now you’re moving on.
ALL ABOUT BALANCE
Conversations with your boss don’t have to be anxiety-inducing standoffs.
With a few carefully chosen topics, a touch of humour and a solid exit strategy, you’ll go from awkward silences to effortless banter in no time.
So, if you ever find yourself stuck in an elevator heading to the 28th floor with your superior, you're all set. Just leave the “email and stuff” behind.
Kelvin Kao is the co-owner of a creative agency and a cafe.
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