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The Cost of Not Listening with Oscar Trimboli

The interview with Oscar Trimboli was about deep listening skills to extract insights for leaders to become better listeners and communicators.

Key Takeaways

  • We discuss “what’s the cost of not listening?” early in the interview to draw people in.
  • Listen with your whole body – drink water, play music etc. to ground yourself before meetings.
  • Ask for feedback subtly by asking “what’s one thing you’d change about this meeting?” rather than directly.


Oscar’s journey to deep listening

  • As a teenager, Oscar’s protruding jaw made him self-conscious so he learned to ask good questions and listen to avoid drawing attention to himself.
  • Playing card games with diverse nationalities, Oscar learned to read body language and non-verbal cues since they spoke other languages.
  • A pivotal moment was when his Microsoft VP told him he could “change the world” if he could code how to listen well.

Productive vs unproductive ego

  • Ego can be useful to protect us but unproductive when trying to dominate others.
  • Leaders should ask if their ego is being productive or not in conversations.
  • Productive ego invites perspectives from whole group before speaking again.

Whole body listening

  • Listen with your whole body by grounding yourself before meetings (drink water, play music etc.)
  • As host, don’t start meetings on the hour – give a 5 minute buffer for people to transition.
  • Do walking 1-on-1 meetings to fully tune in.

Leaning into emotional conversations

  • Don’t run from emotional conversations – ask “when did you form this perspective?” to dig deeper.
  • Silence draws out truth; pauses are okay and even powerful.

Seeking feedback as a leader

  • Don’t directly ask for feedback from low-trust relationships.
  • Subtly ask “what’s one thing you’d change?” or “how would you summarize this meeting?”

You can learn more about Oscar over at his website, Oscar Trimboli. You can also take the Listening Quiz to learn about how you can improve your listening skills. You can also connect with him on LinkedIn. Check out his book, How to Listen (Amazon Link).

As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

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