Oscar Trimboli: Deep Listening: The Leadership Skill That Transforms Teams and Results
Tue Feb 03 2026
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 understandingHearing versus listening and why action is the differentiatorHow role-based seniority correlates with roughly 2.5x more interruptions in meetingsThe cognitive delta between speaking, thinking, and listener processingPractical 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
Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.
More
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 understandingHearing versus listening and why action is the differentiatorHow role-based seniority correlates with roughly 2.5x more interruptions in meetingsThe cognitive delta between speaking, thinking, and listener processingPractical 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 Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.