In this episode of The Leadership Toolkit, Mike Phillips sits down with award-winning author, keynote speaker, and Deep Listening podcast host Oscar Trimboli to explore what it really means to listen as a leader. Oscar shares the pivotal boardroom moment at Microsoft that sparked his quest to “code” how the world’s best listeners operate and explains why the difference between hearing and listening is always found in the action you take afterward.

Drawing on research with over 35,000 people, Oscar and Mike unpack the neuroscience of listening and why most leaders only ever engage with about 14 percent of what their people truly think and mean. You will hear practical, high-impact questions you can start using right away, including “What will make this a good conversation” and “How long have you been thinking about this,” along with simple prompts like “Tell me more” and “And what else” that help people move past their first, surface-level answer.

Oscar also breaks down the difference between showing up “in service” to the conversation and slipping into a “servant” mindset that quietly burns leaders out.

If you want to move beyond simply hearing words and start listening for meaning, this conversation is your roadmap.

🧰 Tools of the Trade: Top Takeaways You Can Use

1️⃣ Hearing vs listening: Hearing is momentary, but listening happens before, during, and after. The proof you listened is always found in the action you take.

2️⃣ The 14 percent rule: We speak at 125–150 words per minute but think near 900. The first thing someone says is only about 14 percent of what they mean, so leaders must create space for a second, deeper expression of the idea.

3️⃣ Questions that shift conversations: Asking “What will make this a good conversation” or “How long have you been thinking about this” helps people reveal what they actually mean and think more deeply, instead of jumping straight to solutions.

4️⃣ Service vs servant leadership: Showing up in service moves the conversation forward. Showing up as a servant overplays empathy and turns work meetings into therapy, which is not healthy or sustainable.

5️⃣ Great leaders build listening cultures: Good leaders get people to listen to the speaker. Great leaders get teams listening to each other, multiplying ownership and freeing the leader from being the constant center.

6️⃣ Silence is the hidden key: Silent and listen share the same letters. Pausing, holding silence, and using prompts like “Tell me more” or “And what else” help people move past their first 14 percent into deeper meaning.

Contact Information:
Oscar Trimboli

Email: podcast@oscartrimboli.com

LinkedIn: ⁠https://www.linkedin.com/in/oscartrimboli⁠

Website: https://www.oscartrimboli.com

Listening Quiz: https://listeningquiz.com

Mike Phillips

Email: ⁠⁠⁠⁠mike@TheLeadshipToolkit.com⁠⁠⁠⁠

LinkedIn: ⁠⁠⁠⁠Linkedin.com/in/LeadTheTeam⁠⁠⁠⁠

Twitter: ⁠⁠@LeadershipTLT⁠

YouTube: ⁠YouTube.com/@MikePhillips

Credits:

Hosted by Mike Phillips

Produced by The Leadership Toolkit Team

Guest: Oscar Trimboli

Watch more episodes of the Leadership Toolkit at https://spotify.TheLeadershipToolkit.com

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