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.