
Coffee House Coaching
Coffee House Coaching is an Executive Coaching podcast where I speak with fellow Executive Coaches about their practice, their process and how they help their clients. I also speak with individuals impacted by coaching and how it has improved their lives. My goal is to shine some light on the wonderful world of Executive Coaching and explain what it is and how it works. So, grab a cup of coffee, sit back, relax, and enjoy my conversations about Executive Coaching.
Coffee House Coaching
Ep 158 Oscar Trimboli Gr8 Q's - "How to Listen" Author (Wonderful Book)
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Gary Nowak
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Season 4
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Episode 158
Episode Summary: Oscar Trimboli
1. Best Coaching Advice Received
- "If you can achieve it in your lifetime, it’s not a worthy ambition."
- Encouraged by mentor Matt to continually raise the bar.
- Led to goal of influencing 100 million deep workplace listeners.
- Shaped Oscar’s approach to time leverage and impact.
- Constantly evaluating: “Is this scalable? Is it amplified?”
2. Still Improving in Coaching
- Building asynchronous coaching tools to reach more people.
- Writing ethical AI software to analyze coaching conversations.
- Investigating how clarifying questions arise from speaker behavior.
- Transitioning from 1-on-1 coaching to scalable, tech-driven learning.
- Belief: Coaching created by humans doesn’t always need humans present.
3. Most Outrageous Coaching Move
- Walked out of a toxic leadership meeting mid-session.
- Noticed shift in group energy after a disruptive person entered.
- Triggered an honest, heated discussion—led to co-owner resigning.
- CEO later thanked Oscar; group had ignored the issue for years.
- Takeaway: Presence (and absence) can shift a room more than words.
4. What Still Makes Him Uncomfortable
- When he senses a question may come from ego, not service.
- Discomfort often arises from reactions to others, not from within.
- Constantly asks: “Is this question for me, them, or us?”
- Works to reduce self-oriented questioning and stay attuned.
- Awareness around where questions originate keeps him grounded.
5. Advice to Aspiring Coaches
- “Embrace the process.”
- Every coach has strengths and gaps—be okay with that.
- Commercial side may be easy or hard, same with client types.
- Work with a supervisor/mentor to gain perspective.
- The longer he coaches, the more he realizes how little he knows.
6. Biggest Personal Challenge Conquered
- Ego. Fastest answer in the episode.
- Learned to listen more deeply, write more vulnerably (especially after his father’s stroke).
- Strives to let go of ownership over ideas—sees himself as a conduit.
- Attributes courage and integrity to lessons from his immigrant father.
7. Use of AI in Coaching
- Uses AI to:
- Teach himself coding.
- Enhance his question-writing.
- Map coaching interviews to ICF and Gallup frameworks.
- AI helps generate better, clearer, lower-word-count coaching questions.
- Sees AI as a reflection partner—not a replacement for the human element.
8. Self-Discovery via Coaching
- Harsh inner critic—“should be arrested” level self-talk.
- Coaching and supervision helped him ease internal aggression.
- Now able to acknowledge inner voice, set boundaries with it.
- Created space for more compassion toward himself.
- Coaching has shifted his relationship with himself, not just others.