The Red Lipstick Moment
It is the small acts of honesty that build trust — and why the conversations that matter most are rarely the ones we plan.
It wasn’t a big revelation. That was the point.
I was running a Silo Breaker workshop for a team — one of those sessions where people arrive a little guarded, not quite sure what they’ve signed up for, waiting to see if it’s safe to be honest.
Partway through, a woman shared something quietly. When she’s facing a challenge — a difficult conversation, a moment of doubt, a day when the ground feels uncertain — she reaches for her red lipstick. She puts it on, looks in the mirror, and finds the courage she needs to take the next step.
It was a simple story. Completely unscripted. She wasn’t trying to make a point or impress anyone.
But the room shifted. You could feel it. People leaned in. Some smiled in recognition. Others went quiet in that particular way that means something has landed.
What she’d shared wasn’t dramatic. It was human. And that’s exactly why it worked.
Trust doesn’t begin in performance. It begins in the moments that feel real.
When Someone Says the Thing Nobody Expected
I’ve seen versions of this moment many times — in workshops, at my Catalyst Dinners, in one-to-one conversations that started as something else entirely.
At a recent dinner, a participant said something that stopped the table. 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. The quality of what she was creating, day by day.
It was a quiet observation. But it opened something up in the room. People began reflecting on their own definitions — what they’d been chasing, what they actually wanted, whether those two things were still the same.
Neither of these moments — the lipstick or the dinner table — was rehearsed. Neither was trying to prove anything. They built trust precisely because they weren’t.
We spend so much of our professional lives in performance mode. Saying the right thing. Managing how we’re perceived. Keeping things polished and contained. And underneath all of that, most people are quietly hungry for something more honest.
“Authentic conversation isn’t about oversharing. It’s about being genuine enough to move past the automatic script and actually meet the person in front of you.”
Why This Matters More Than We Admit — Especially in Teams
It’s easy to think of authentic conversation as something that belongs in personal relationships. In friendships, in families, in the kinds of conversations you have over a long dinner with people you trust.
But in my experience, it’s just as essential at work. Perhaps more so — because it’s so much rarer there.
When people feel safe enough to speak honestly in a team — to name a challenge, share a perspective that differs from the group, or simply be real about where they are — something shifts. Decisions get better. Trust builds faster. Collaboration stops being a word on a strategy document and starts being something that actually happens.
The woman with the red lipstick wasn’t sharing a personal secret. She was showing the people around her who she actually was. And in doing that, she gave everyone else in the room a little more permission to do the same.
That’s what I mean when I talk about conversations that break silos. Not a structured exercise or a team-building activity. A moment of genuine honesty that changes the temperature of the room — and makes every conversation that follows a little more real.
Real Stories Help Us See What’s Possible
This is also what I love most about the conversations I have on my podcast.
They’re not interviews. They’re real exchanges with people who care deeply about something — and who are willing to talk honestly about what shaped them, what they’ve learned, and what they’re trying to create.
Two conversations from Series 2 stay with me.
Sara Shams spoke about what it means to move from visibility to influence — using her voice, her lived experience, and her leadership to challenge ableism and broaden representation. Sara is a bilateral above-knee amputee now shaping policy and empowering organisations to include intersectional voices. What struck 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 how she’s creating spaces where people of all abilities can build confidence, experience joy, and reconnect with what’s possible through movement. Her journey — from celebrity trainer and TV fitness expert to building one of Australia’s most unique inclusive wellness spaces — is one of resilience, creativity, and genuine heart.
Different stories entirely. But both reflecting the same truth: when people speak honestly about what matters to them and the impact they want to create, others are invited into a deeper kind of connection. That’s where trust grows.
How to Create More of This in Your Own Conversations
You don’t need a workshop or a curated dinner to have more authentic conversations. You need a few small shifts in how you show up.
• Slow down enough to actually listen. Not to respond — to understand. There’s a difference, and people feel it.
• Ask better questions. Move beyond “how are you?” and “what do you do?” Try: what’s been on your mind lately? What matters most to you right now? What are you navigating that others might not see?
• Let something real land. When someone shares something genuine — don’t redirect, don’t fill the silence, don’t rush to your next point. Stay with it. That pause is where trust is built.
• Be willing to go first. You don’t have to share everything. But a small act of honesty — naming a challenge, admitting uncertainty, saying something true — gives others permission to do the same.
• Notice the room. In any group — a team, a workshop, a dinner table — the most important voice is often the quietest one. Create space for it.
The Conversations That Stay With You
Some conversations stay with you not because they were loud or impressive or perfectly timed.
They stay because something real was said. A truth. A moment of honesty that shifted the tone and invited everyone else to go a little deeper.
The red lipstick moment stayed with me. The dinner table comment stayed with me. Sara’s clarity stayed with me. Margie’s heart stayed with me.
These are the conversations that matter. Not because they were planned — but because someone chose, in that moment, to be genuine.
Trust isn’t built in the polished moments. It’s built in the real ones.
If you’re curious about what becomes possible when the right people are in a room together — genuinely listening, genuinely honest — I’d love to have a conversation.
That’s exactly what I create at my Catalyst Dinners and in my Silo Breaker workshops. Not performance. Not networking. Just real conversation — and what it makes possible.
The Conversations That Change Us · Melbourne · 18 June · 14 seats
kerryn-powell.com.au/shop/in-person-dinner
Or explore the Silo Breaker workshops at kerryn-powell.com.au/silo-breaker-workshops
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.
