Creating Conversations That Count: Four Questions to Unlock Opportunities.
How the right question moves a conversation from surface to something that actually matters.
The Comment That Stopped the Room
At a recent dinner I hosted, a participant said something that quietly changed the direction of the entire evening.
She said that for her, success and fulfilment had very little to do with work. That what mattered most was how she lived her life. The values she kept. How she showed up. The quality of what she was building, day by day — not in her business, but in herself.
It was a simple observation. She wasn’t making a grand statement. But something about the honesty of it opened a door.
People who had arrived ready to talk about strategy and goals began reflecting on something deeper. What they actually wanted. Whether the path they were on still matched the person they were becoming.
That’s what a real conversation does. It doesn’t just exchange information. It shifts something.
Most of us spend the majority of our professional lives at the surface — updating, reporting, networking, presenting. All necessary. But rarely the conversations that stay with us, that change how we see something, or remind us what actually matters.
The question worth asking is: how do we create more of those moments? Not just at curated dinners, but in everyday professional life?
Why Most Conversations Stay at the Surface
It’s not that people don’t want to go deeper. In my experience, most people are quietly hungry for more genuine exchange. They’re tired of the automatic scripts, the polished answers, the meetings that cover everything and say nothing.
What keeps conversations at the surface is usually one of three things.
The first is habit. We ask “how are you?” and answer “good, thanks” without either party intending anything more. It’s not dishonesty — it’s autopilot.
The second is pace. When we’re busy and distracted, we listen enough to respond rather than enough to understand. There’s a difference, and people feel it.
The third is uncertainty about permission. People often want to say something real but aren’t sure the other person wants to hear it. So they stay safe. They stay polished. And the moment passes.
Real connection begins when someone decides to go first. To ask a better question. To actually listen to the answer.
Better Questions Create Better Conversations
The single most practical shift you can make in any conversation is the quality of your opening question.
Most professional conversations begin with “what do you do?” It’s not a bad question. But it invites a rehearsed answer. And rehearsed answers lead to surface exchange.
Here are four questions I come back to — each designed to invite something more genuine:
• What’s been on your mind lately? This is an open door. It gives the other person permission to bring what’s actually present for them, rather than what’s on their business card.
• What matters most to you right now? Not in theory — right now, at this point in your work or your life. The specificity of it tends to produce a real answer.
• What are you working on that you’re most excited about? People light up when they get to talk about what they genuinely care about. This question finds that thing.
• What are you navigating that others might not see? This one takes a little more trust to ask — but when the conditions are right, it opens something up that rarely gets said in professional settings.
None of these are magic. What they have in common is intention. They signal that you’re genuinely interested — not filling space, not waiting for your turn to speak. And people can feel the difference.
Listening Is the Other Half
A better question only works if it’s followed by genuine listening.
Most of us listen at about half capacity in professional settings. We’re forming our response, checking our phone mentally, wondering if we’ve said the right thing. Real listening — the kind that makes people feel genuinely heard — requires us to stay with what’s being said. To let it land before we respond.
A few things that help:
• Resist the urge to redirect. When someone says something unexpected or personal, the instinct is often to move on quickly. Don’t. Stay with it. “Tell me more about that” are three words that change almost every conversation.
• Leave silence. The discomfort of a pause is where the more considered, more honest response often lives. When you let silence exist, you signal that you’re in no hurry — and that what the other person says matters more than filling the gap.
• Remember what people share. Follow up. Reference it later. “How did that go?” is a small gesture that carries a powerful message: you were listening, and you genuinely care about the answer.
Real Stories Create Real Connection
One of the things I love most about the conversations I have on my podcast is that they model exactly this.
They’re not interviews. They’re real exchanges with people who are willing to speak honestly about what matters to them — what shaped them, what they’ve learned, what they’re trying to build.
Sara Shams spoke about what it means to move from visibility to influence — using her voice, her lived experience as a bilateral above-knee amputee, and her leadership to challenge ableism and create genuine representation in the organisations she works with. What stayed with me wasn’t just what she’s achieved. It was her clarity about why it matters — and her willingness to speak from that place without softening it.
Margie Cerato shared the journey from celebrity trainer and TV fitness expert to building one of Australia’s most unique inclusive wellness spaces — a story of resilience, creativity, and genuine heart. What she’s created is extraordinary. But what made the conversation memorable was her honesty about the path.
These are very different stories. But both reflect the same truth: when people speak honestly about what matters to them, others are invited into a deeper kind of connection. That’s where trust grows. And that’s where real collaboration becomes possible.
Trust Is Built in the Moments That Feel Real
Here’s what I’ve observed across years of facilitating rooms, hosting dinners, and creating spaces for professionals to connect: trust isn’t built in the polished moments.
It’s built when someone says something true. When they drop the script and speak from experience. When they ask a question they genuinely don’t know the answer to, and stay curious about what comes back.
Those moments — the simple, unscripted ones — are what people remember. Not the presentations, not the formal agendas, not the carefully worded updates.
Authentic conversations help people feel that they can exhale. That they don’t have to perform. That they can be real.
And when that happens, connection becomes something more than professional courtesy. It becomes the foundation for the relationships that actually move things forward.
Ready to Practise?
Reading about better conversations is one thing. Practising them — in a space designed to feel genuinely safe — is where the shift actually happens.
I’m running Conversations Count sessions online this year: a small-group, 60-minute guided experience for professionals who are ready to show up in conversations with greater confidence and intention.
This isn’t traditional networking. It isn’t training. It’s a deliberate, human conversation — where you’ll explore tried and tested insight, practise in a small and supportive group, and leave with something concrete: a clearer intention and the confidence to carry it into the conversations already waiting for you.
Let me know if you would like more details or if you’re ready to take the next step — a curated dinner in Melbourne on 18 June, The Conversations That Change Us, brings a small group of curious professionals together for an evening of guided, meaningful exchange. 14 seats. Details at kerryn-powell.com.au/shop/in-person-dinner
Hello, I’m Kerryn Powell — The Network Catalyst.
I help people and teams create better conversations that lead to clarity, confidence, connection, and meaningful impact.
Through mentoring, workshops, facilitation, and speaking, I create the conditions for trust, collaboration, and the hidden opportunities already around you. Because meaningful opportunities do not begin with more networking. They begin with better conversations.
If this resonates, let’s start a conversation.
