Coffee House Coaching

Ep 158 Oscar Trimboli Gr8 Q's - "How to Listen" Author (Wonderful Book)

Gary Nowak Season 4 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.