🎙️ What if the key to transformational leadership wasn’t speaking more, but listening better?
In this powerful episode of The Kind Leader Podcast, host Gino Degregori sits down with Oscar Trimboli, bestselling author and host of the award-winning Deep Listening podcast, to explore the profound impact of listening in leadership. With experience guiding Fortune 500 companies and government leaders, Oscar breaks down the Five Levels of Listening, and why most of us are stuck at the surface.
Discover how a moment at Microsoft sparked Oscar’s mission to “change the world through listening” and led him to build tools, books, and assessments that have influenced over 35,000 professionals.
From the hidden costs of poor listening to the neuroscience of presence, Oscar shares eye-opening insights, practical tips (like turning off notifications!), and timeless wisdom that will elevate the way you lead, collaborate, and connect.
🔑 Key takeaways include:
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Why 92% of people never get past level 2 listening
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The surprising business cost of not listening (spoiler: it’s big)
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How to verify what someone really heard
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The power of honoring the past before leading change
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Why true kindness in leadership starts with deep presence
💡 Whether you’re a CEO, team leader, or changemaker, this episode will reshape how you listen, and lead.
🎧 Listen now and start leading with deeper impact.
Links
🔗 Connect with Oscar Trimboli on LinkedIn: linkedin.com/in/oscartrimboli
🧠 Discover your listening style: Take Oscar’s free 7-minute quiz at listeningquiz.com to get personalized tips to improve how you listen in workplace conversations.
Chapters 00:00 Why Deep Listening Changes Everything 05:02 Kind Leadership Starts with Presence 09:48 Leading Through Change—One Conversation at a Time 17:07 Unlocking the 5 Levels of Listening 21:56 How Tech Disrupts Human Connection 24:30 Notifications Are Killing Your Focus 28:40 The Real Cost of Not Listening 36:47 The Next Era of Kind Leadership 40:09 Quickfire Wisdom: Lessons You Can Apply Today