Leadovation Oscar Trimboli: Deep Listening: The Leadership Skill That Transforms Teams and Results
About Oscar Trimboli:
Oscar Trimboli is an award-winning author, host of the Apple award-winning podcast Deep Listening, and a sought-after keynote speaker. His third book is How to Listen – Discover the Hidden Key to Better Communication, a comprehensive book about listening in the workplace. Along with the Deep Listening Ambassador Community, he is on a quest to create 100 million deep listeners in the workplace. Through his work with chairs, boards of directors, and executive teams, Oscar has experienced first-hand the transformational impact leaders can have when they listen beyond words.
In this episode, Dean Newlund and Oscar Trimboli discuss:
- The organizational cost of incomplete listening and misaligned understanding
- Hearing versus listening and why action is the differentiator
- How role-based seniority correlates with roughly 2.5x more interruptions in meetings
- The cognitive delta between speaking, thinking, and listener processing
- Practical tools for improving meeting outcomes, collaboration, and decision-making
Key Takeaways:
- Begin meetings by asking “What would make this a good meeting?” to align shared outcomes and reduce unspoken assumptions.
- Surface communication and listening preferences early to remove ambiguity and improve contribution equity.
- Write questions down first, shorten them to eight words or fewer, and verify that they serve the shared outcome rather than personal validation.
- Shift default meeting norms: avoid top-of-hour starts and shorten durations to reduce cognitive switching costs and increase presence.
"I think a lot of leaders listen to what's said, and great leaders listen to what's not said.” — Oscar Trimboli
Connect with Oscar Trimboli:
Website: https://www.oscartrimboli.com
Books: https://www.oscartrimboli.com/shop/ & https://www.amazon.com/stores/Oscar-Trimboli/author/B07R9RP1XZ
LinkedIn: https://www.linkedin.com/in/oscartrimboli/
See Dean’s TedTalk “Why Business Needs Intuition” here: https://www.youtube.com/watch?v=EEq9IYvgV7I
Connect with Dean:
YouTube: https://www.youtube.com/channel/UCgqRK8GC8jBIFYPmECUCMkw
Website: https://www.mfileadership.com/
The Mission Statement E-Newsletter: https://www.mfileadership.com/blog/
LinkedIn: https://www.linkedin.com/in/deannewlund/
X (Twitter): https://twitter.com/deannewlund
Facebook: https://www.facebook.com/MissionFacilitators/
Email: dean.newlund@mfileadership.com
Phone: 1-800-926-7370
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