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50. Listening Beyond Words, and Choosing What to Say No To | Oscar Trimboli

15 Dec 2025

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How much of what matters most are you missing while you're listening? Not the words themselves (you're good at capturing those) but what's underneath them, between them, beyond them. Here's the uncomfortable truth: most of us believe we're better listeners than we actually are. We're busy preparing our response, managing the future, or distracted by the ping of the next urgent thing. Meanwhile, the people in front of us (the ones we're meant to be leading) are telling us everything we need to know. If only we knew how to truly hear it.In this conversation with Oscar Trimboli, we explore something deeper than communication skills. We venture into the territory of how we show up, what we say no to, and why the foundations we've already built might matter more than the future we're chasing. This is about the shift from hero to host, from infinite ambition to the surprising lightness of a ‘tour of duty’, and from listing ingredients to sharing the story of the meal.Oscar Trimboli is on a quest to create 100 million deep listeners in the workplace. He's spent decades discovering that the gap between speaking and listening isn't just about paying attention. It's about understanding that how we frame something can change what happens next. His work helps leaders see what they're missing when they focus only on the words.In this conversation, you'll discover:• Why the legacy you're creating might already exist in ways you can't yet see, and how acknowledging your past builds the foundation for what's next• How setting boundaries isn't about limitation but about the strategic clarity of knowing what you choose not to do• Why corporate funerals (literally burning what no longer serves) can create the trust that moves organisations forward when change initiatives get stuck• How the "tour of duty" mindset releases the weight of infinite responsibility and brings unexpected lightness to leadership• Why effective leaders operate as hosts rather than heroes, facilitating learning instead of performing expertise• How metaphors become mental shortcuts that help people understand the unfamiliar through the familiar, and why food and music work better than sport• Why distraction isn't just about devices but about the stories we tell ourselves when our attention wanders, and what choices we have in those moment• How "getting over yourself" enables you to serve the work rather than protect your ego, and why this shift makes everything else easierTimestamps:(00:00) - Introduction(06:39) - The Importance of Boundaries(10:32) - Navigating Change and Acknowledging the Past(19:11) - Corporate Funerals: Letting Go to Move Forward(24:41) - The Power of Rituals in Leadership(32:46) - Navigating Distractions in Conversations(42:59) - The Impact of Metaphors in CommunicationOther references:Animal Liberation OrchestraDeep Listening: Impact Beyond Words by Oscar TrimboliDeep Listening QuizYou can find Oscar at:Website: oscartrimboli.comLinkedIn: linkedin.com/in/oscartrimboliTake the Deep Listening Quiz: listeningquiz.comCheck out my services and offerings

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