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Impactful Coach
Episode 45Coaching demo51 min

Befriending Inherited Beliefs: Coaching Demo with Jerry Colonna

with Jerry Colonna, CEO & Co-Founder of Reboot.io; Executive Coach

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Show notes

A coaching podcast with Jerry Colonna and Tobias Weghorn, centered around a coaching demo that quickly moves from “Am I enough?” to where that belief may come from in the first place. Tobi shares how safety and financial security shaped parts of his family story, and Jerry helps reframe those fears through compassion for inherited patterns. They also unpack why coaching mastery beyond methodology often requires dropping the “right way vs. wrong way” obsession and paying attention to what actually works in the moment. Along the way, they touch on radical self-inquiry, the role of supervision, and how countertransference and the third can become practical data for coaches.


Key Learnings:

  • Use coaching demo moments to surface the real driver (e.g., safety beliefs behind “not enough belief (I am enough)”), then work with what’s alive rather than forcing a script.
  • Practice radical self-inquiry without shame: name the benefit of the inherited pattern first, then build change through repetition (not just cognitive insight) so the coaching demo insight sticks under stress.
  • Build coaching supervision into your craft: track countertransference and the third (what you feel in-session) as information, so you don’t default to “more methodology” when you and your client feel stuck.


Resources:


Episode Chapters:

00:00 Mastery Beyond Methodology: The “Right Way” Trap

01:00 Introduction: The “Am I Enough?” Belief And A Coaching Demo Setup

04:00 Leaders, Safety, And The Human Condition Behind “Not Enough”

14:00 Coaching Demo: Inherited Family Trauma And Safety Beliefs

21:00 Making “I Am Enough” Stick: Benefits, Repetition, And Radical Self-Inquiry

30:00 Why Coaches Get Stuck: Methodology, The Third, And Countertransference

43:00 Coaching Supervision And Tracking What You Feel In Session

47:00 A Practical Habit: Notes On What The Client Says vs. What You Feel

Transcript

Full transcript, edited for readability. Every timestamp jumps the video to that moment.

Jerry Colonna: My first psychoanalyst is a woman named Dr. Sayers. And Dr. Sayers, I worked with her for 30 years. She used to say all the time, there's a right way, there's a wrong way, and there's a way that works. Most coaches get so fixated on the right way or the wrong way, the right way, the wrong way, that they lose consciousness of what's working and what's not working. Methodology is really, really important, but mastery is when you learn to drop the methodology. And my fear is that too many coaching programs skip that part. Tobi: Have you ever caught yourself worrying whether you are enough? At work, in your role as a coach, or simply financially? This kind of unconscious belief and worry is what Jerry Colonna talks about in his somewhat autobiographic books, Reboot and Reunion. And it's a theme that I could resonate with quite a bit when I was reading them last year. Ironically, Jerry is an extremely successful executive coach with a background in venture capital, who has been on podcasts like the Tim Ferriss Show, and who has been coaching leaders for over two decades. And on today's episode he does a brief session with me. Somewhat surprisingly, we end up talking about to what extent these kinds of beliefs are inherited, and how we, or our clients for that matter, need compassion for our parents and grandparents to overcome them. The coaching demo we have is relatively short, and as usual I try to unpack Jerry's Tobi: approach, his coaching methodology, afterwards. And I learned that there is no methodology, no plan, no framework, but a lot of what a psychoanalyst might call the third ear. So whether you're just starting out or you've been coaching for decades already, this one might challenge how you think about methodology, about coaching mastery, and about what it really takes to grow as a human and as a coach. Let's go.

Read the full transcript

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