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May 6, 2025 65 mins

Oscar Trimboli has spent his life helping people hear what’s not being said. As a listening expert and advisor to some of the world’s largest companies, he’s discovered a surprising truth: most of us only catch a fraction of what’s being communicated. We hear the words, but miss the silences, emotion, and meaning beneath them. In this episode, Dart and Oscar explore the five levels of listening, what it takes to make someone feel truly seen, and how listening can be taught, measured, and embedded into teams.

Oscar Trimboli is a speaker, leadership coach, and the author of How to Listen. He hosts the Apple award-winning podcast Deep Listening and has worked with clients such as Microsoft, AstraZeneca, and Cisco to improve communication and collaboration through listening.

In this episode, Dart and Oscar discuss:
- The five levels of listening
- What it takes to make someone feel truly seen at work
- Why most of us only hear 14% of what someone really means
- The link between listening and action
- How listening can reduce meetings and increase effectiveness
- Why silence is the most powerful listening tool
- What metaphors reveal about how people see the world
- How to teach listening as a core leadership skill
- And other topics…

Oscar Trimboli is a speaker, author, and host of the Deep Listening podcast. His mission is to create 100 million deep listeners in the workplace. He’s advised organizations including Microsoft, AstraZeneca, and HSBC on how to listen beyond the words and build cultures of understanding. His latest book, How to Listen, explores the science and practice of listening well—and why most of us do far less of it than we think.

Resources Mentioned:
How to Listen, by Oscar Trimboli: https://www.amazon.com/How-Listen-Discover-Hidden-Communication/dp/1774581914
The Deep Listening Podcast: https://www.oscartrimboli.com/podcast/
Listening Quiz (Discover your listening barriers): https://www.listeningquiz.com
Unreasonable Hospitality, by Will Guidara: https://www.amazon.com/Unreasonable-Hospitality-author/dp/1529146828
Don't Think of an Elephant! by George Lakoff, Howard Dean, & Don Hazen: https://www.amazon.com/Dont-Think-Elephant-Values-Politics/dp/1931498717

Connect with Oscar:
Website: https://www.oscartrimboli.com
LinkedIn: https://www.linkedin.com/in/oscartrimboli 

Work with Dart:
Dart is the CEO and co-founder of the work design firm 11fold. Build work that makes employees feel alive, connected to their work, and focused on what’s most important to the business. Book a call at 11fold.com.

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