Oscar Trimboli, a mentor and former Microsoft director, dives into the art of deep listening, emphasizing its transformative power in leadership. He discusses practical strategies to encourage speakers to share more, like asking, "What else are you thinking?" Trimboli highlights the importance of creating a receptive space for genuine communication. He also tackles common myths about listening, stressing that effective leaders must not only listen but also take action on what they hear, fostering a culture of open dialogue and understanding.
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insights INSIGHT
Initial Utterances vs. True Meaning
What someone says initially may not be what they truly mean.
Explore their deeper meaning by prompting them to elaborate.
volunteer_activism ADVICE
Ask Clarifying Questions
Ask questions that help the speaker understand their own thinking, not just share information.
Use phrases like "Tell me more" or "What else are you thinking?"
question_answer ANECDOTE
Peter's Phone
Microsoft executive Peter role-modeled presence by switching off his phone before a meeting with CEOs.
This prompted others to do the same, creating a more engaged and focused discussion.
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Deep Listening, Impact Beyond Words
Oscar Trimboli
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, he 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*.
Key Points
Listen beyond the words that are said and try to determine what the speaker is really trying to say.
The more senior you are, the more listening you’ll do.
Ask the speaker: “Tell me more” or “What else are you thinking?” or “How long have you been thinking about that?”
To be a great listener, you have to create a space where you’re available to listen.
For every hour you listen, you need to spend another hour in action.
Leaders often are not great at hearing all the opinions in the room.
Bonus Audio
Three tips to becoming a better listener
Resources Mentioned
The 5 Myths of Listening
Deep Listening: Impact Beyond Words* by Oscar Trimboli
Book Notes
Download my highlights from Deep Listening in PDF format (free membership required).
Related Episodes
How to Be a Non-Conformist, with Adam Grant (episode 238)
How to Increase Your Conversational Intelligence, with Judith Glaser (episode 271)
How to Become the Person You Want to Be, with James Clear (episode 376)
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