I found myself unintentionally eavesdropping on a conversation in the security queue at Sydney airport recently. (Please don’t judge me for eavesdropping – let’s call it observational research)
So imagine this: I arrive at the airport with no bags to check and head straight to security. The queue is long and winding, a human snake of travellers edging toward the same goal – freedom to move forward. As I fall into line, I find myself just behind two colleagues walking single file, deep in conversation.
The woman leans in slightly and asks, “So, what did you learn from it?” Her tone is direct, almost challenging.
He replies, “Honestly, I was caught off guard. I guess I just need to be better prepared for the next conversation.
She comes back quickly, “But how will that actually help? It’s not like he’s going to change.”
He shrugs and says, “Yeah, that’s Jezza for you.”
“That’s not on,” she replies. “You’ve got to have it out with him.”
“Yeah, I know,” he says.
Then she finishes with, “So what will you do differently next time?”
And his answer? “I guess I just have to be brave and do it. I need to talk to him.”
With that, we hit the checkpoint and peel off into separate lanes. I was oddly disappointed. I genuinely wanted to hear where they’d land.
But it got me thinking – through a leadership lens, this was a masterclass in coaching… or almost.
Let’s break it down.
Here’s what I liked:
Open-ended questions: The conversation wasn’t full of yes/no traps. She kept it moving by prompting reflection – what did you learn, what will you do differently?
Connection and trust: He didn’t hesitate to respond. That says something about the psychological safety between them. Care was present: Even in her brevity, you could hear concern. She wasn’t criticising for the sake of it – she was trying to help him grow.
Here’s what could have been better:
Timing matters: Was the security line the best moment for this kind of conversation? Maybe they were coming straight from a meeting, or perhaps it was their only chance to talk in person. Still, meaningful conversations deserve the right time and space. If in doubt, make a commitment to revisit it when there’s more breathing room.
Tone is everything: The way a question is asked can shift its entire impact. “What did you learn from it?” asked with curiosity feels different than when it’s asked with frustration. Tone can either build trust or chip away at it.
Stay in the question: She slipped in a few leading statements like, “It’s not like he’s going to change.” Those kinds of remarks, even if well-intentioned, can close off exploration. Better to reframe as a question:
“How do you think your approach will land if this happens again?”
“What makes you think Jezza might – or might not – be open to change?”
The goal is to open up the space for deeper thinking, not funnel someone toward a specific view.
To lead like a coach is to:
Connect with empathy, ask with curiosity, calibrate your approach, support without rescuing
So to the two business associates at Sydney airport – thank you for the lesson (and apologies for tuning in). You reminded me that great coaching moments can happen anywhere… but that the best ones are intentional.
And to the rest of us – next time you’re tempted to give advice, try asking a better question instead. You might be surprised what opens up.
