Oscar Trimboli: Coding How We Listen to Transform Leadership

Listening isn’t just a soft skill—it’s a system you can code, measure, and use to transform how teams perform. In this episode, you’ll hear how one pivotal moment at Microsoft sent Oscar Trimboli on a journey to decode listening, redesign meetings, and change the way leaders communicate forever.

In this episode, Gary and Oscar Trimboli discuss:

The origin story of “coding how to listen” at MicrosoftMeasuring listening: share of voice, turn-taking, and curiosityDesigning better meetings: purpose, process, and participationEngaging introverts and unlocking silent perspectivesRelevance vs. repetition in leadership messaging and behavior change

Key Takeaways:

One courageous piece of feedback about how you listen can completely redirect a career and reveal an overlooked superpower.Listening can be quantified through data points like share of voice, turn-taking ratios, and question types, giving leaders a clear mirror on how their meetings actually run.Great meetings start by clarifying purpose and asking participants what would make it a good conversation, aligning everyone’s attention from the outset.Introverts often contribute the deepest synthesis when invited to speak from an external perspective—like a customer, competitor, or board member—and given time to prepare.Repeating a message isn’t the problem; failing to make it relevant to where people are in the project or in their lives is what causes them to tune out.

"The right conversation at the wrong time is still the wrong conversation." — Oscar Trimboli

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.

Oscar is a marketing and technology industry veteran who has worked for Microsoft, PeopleSoft, Polycom, and Vodafone. He consults with organizations, including American Express, AstraZeneca, Cisco, Google, HSBC, IAG, Montblanc, PwC, Salesforce, Sanofi, SAP, and Siemens.

He is the author of How to