Oscar Trimboli: Deep Listening

Oscar is a mentor, coach, speaker, and author. He was a director at Microsoft for over a decade and headed up the MS Office division in Australia.

Today, Oscar works with leadership teams and their organizations on the importance of clarity to create change, how to embrace the digital economy, and the role values play in the achievement of your purpose. He is the author of Deep Listening: Impact Beyond Words*.

In this conversation, Oscar details the four habits that tend to derail our listening. We explore the patterns and behaviors of each habit, and how we can work to do better. Plus, Oscar invites us to notice feelings instead of words — as well as HOW people are saying things, not just WHAT they are saying.

Key Points

Four habits that derail listening:

Dramatic Listener

They get engrossed in the emotion and want to become an actor in it. Dramatic listeners tend to get caught up in the problem so much so that they don’t hear the idea or the solution. They may come away from an interaction feeling like they’ve really connected when in fact, they haven’t.

Interrupting Listener

We notice these people the most. They are coming from a place of concern and tend to listen to fix and solve the problem. They finish sentences wrongly and many listen for places to jump in as much as they are listening for the words.

Lost Listener

These listeners tend to zone out and appear not present. Lost listeners may be focused on something else. Technology devices have the potential to distract them substantially.

Shrewd Listener

These listeners are solving the current problem and also the next problem. They may create problems in their own mind that aren’t even what speaker said. They are smart enough not to interrupt, and often appear very engaged, but are not necessarily listening.

Resources Mentioned

Oscar’s Listening Quiz

Deep Listening: Impact Beyond Words* by Oscar Trimboli

The Four Villains of Listening (Deep Listening podcast)

Book Notes

Download my highlights from Deep Listening in PDF format (free membership required).

Related Episodes

The Way to Have Conversations That Matter, with Celeste Headlee (episode 344)

Get Better at Deep Listening, with Oscar Trimboli (episode 408)

The Way to Be More Coach-Like, with Michael Bungay Stanier (episode 458)

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