What if listening isn’t just about hearing words, but could be your most overlooked leadership advantage? In this episode of Headflex, Rebecca and Diane are joined by deep listening specialist Oscar Trimboli to unpack how listening shapes meetings, team dynamics, and leadership impact in the modern workplace.
Drawing on personal stories and research from over 60 professions, Oscar explains why great listeners have rituals and processes to bring their full attention to each conversation. Discover the powerful ripple effects when teams co-create listening environments including quicker meetings, increased trust, and true collaboration. The trio share practical strategies for leaders and participants alike, from setting meetings up for success (hint: don’t start on the hour!) to using the “compass question” that transforms conversations.
Hear why checking in on what’s been heard, not just said, leads to clarity, action, and strong relationships and why “listening to yourself” might be the place to start.
Here are the highlights:
00:00 Meet Oscar Trimbolil
02:17 The pivotal moment that launched Oscar’s listening journey
03:48 What does Coding your listening in the workplace mean?
07:06 Why research in listening is behind other leadership skills
10:09 The world’s best listeners prepare themselves
11:28 Only 20% of a conversation is spoken so what do we listen for in the other 80%?
13:22 Improve meetings by simply shifting when and how they start
15:24 The “compass question” that changes meetings
18:00 Moving from leader-led to team-led listening environments
19:46 The ways we can all influence better listening in meetings
22:54 Role modeling and spotlighting listening habits
28:56 Curating environments for listening
33:04 Tangible rituals to humanise online meetings & team connection
34:41 Should we police phones or make meetings more engaging?
38:08 Getting teams to listen for each other can break silos
44:45 Self-coaching questions
48:45 Oscar Trimboli: “Listening starts by listening to yourself.”
About Oscar Trimboli:
Oscar Trimboli is an author, host of the Apple award-winning podcast Deep Listening and a sought-after keynote speaker. 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.
He believes that when leadership teams focus their attention and listening, they will build organizations that create powerful legacies for the people they serve – today and, more importantly, for future generations.
He is the author of how to listen – discover the hidden key to better communication – the most comprehensive book about listening in the workplace, Deep Listening – Impact beyond words and Breakthroughs: How to Confront Assumptions
Oscar loves his afternoon walks with his wife, Jennie, and their dog Kilimanjaro. On the weekends, you will find him playing Lego with his grandchildren.
Connect with Oscar:
Website: https://www.oscartrimboli.com/about-oscar/
About Headflex:
If you're curious about coaching, Headflex offers a range of coaching programmes to suit different needs. 1:1 coaching, team coaching, group coaching and their Headflex in Residence programme. We also offer Headflex Lunch and Learn sessions. Visit www.headflex.co.uk to find out more.
Connect with us at Headflex:
Email: [email protected].
Website: https://headflex.co.uk/
Instagram:
https://www.instagram.com/head.flex/
Did you know we have a YouTube Channel? You can watch the podcast here: https://www.youtube.com/@headflexcoaching
Connect with Rebecca Walker: https://www.linkedin.com/in/rebeccawalker13/
Connect with Diane Williams: https://www.linkedin.com/in/dianewilliams1
Produced by https://winteraudio.co.uk/
