Silent and Present ~Leading with Listening with Oscar Trimboli

You already know that listening is the foundation of effective leadership; we’re told we have two ears and one mouth for a reason. But what if I told you we’re still missing the mark? Leaders are instructed to be curious, not just reactive, yet many of us get stuck in our own heads, unable to truly hear the people around us, especially when the stakes are high. This week, I dive into the transformative art of listening with Oscar Trimboli, author of How to Discover the Hidden Key to Better Communication and the powerhouse behind the Deep Listening movement. Together, we bust some persistent myths about listening, unpack what it really takes to listen at scale in organizations, and explore the five essential levels of listening, starting with yourself.

Let me tell you about Oscar Trimboli. He is an award-winning author, a sought-after keynote speaker, and the host of the Apple award-winning Deep Listening podcast. With a mission to create 100 million deep listeners in the workplace, Oscar’s research spans interviews with leaders, judges, hostage negotiators, and academics, as well as data from over 35,000 workplace listeners. Through his work with organizations like Microsoft, Oscar has seen firsthand the immense impact leaders can have when they listen beyond just words.

"Silent and listen share the identical letters. The most potent listening technique you can use is simply to be silent." ~Oscar Trimboli

Today on The Rising Leader:

·     Preparation is everything: Listening starts before the conversation.

·     Take a moment to ground yourself: music, water, breath, or clearing your space all help.

·     Five levels of listening: Start by listening to yourself, then to content, context, what’s unsaid, and ultimately, to meaning.

·     The myth of time: Deep listening doesn’t slow things down; it speeds understanding and shortens meetings by surfacing real issues faster.

·     Inner dialogue sabotage: Over 60% of people can’t deeply listen because their own internal chatter dominates. Recognize it, then practice presence.

·     Short questions win: Keep team questions to eight words or less for maximum impact; anything longer is likely a statement in disguise.

·     Listening at scale requires action: Organizations often survey but forget to close the loop. “You said this, we did that” is key to engagement.

·     Clarify before you answer: Don’t be afraid to ask clarifying questions, even in job interviews, to ensure you’re addressing what really matters.

·     Giving vs. paying attention: Giving attention is a choice and a sign of generosity. Paying attention feels like an obligation; shift your mindset and see the difference.

Connect with Oscar Trimboli:

• The Listening Quiz: Take Oscar’s free listening assessment for a personalized report and resources to build your listening skills.

Resources Mentioned:

• Book: How to Discover the Hidden Key to Better Communication by Oscar Trimboli
• Podcast: Deep Listening with Oscar Trimboli
• Easy by Groove Armada, Remember the Name by Fort Minor (musical resources Oscar uses for listening preparation)

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Leader, It’s Time to Rise!

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