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Impactful Coach
Episode 46Interview41 min

The Art of Growing Up with Jerry Colonna: Coaching Queries, Ancestral Beliefs & Coaching vs Therapy

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, digging into radical self-inquiry coaching and what it really means to “grow up” as a leader and as a human. Jerry shares why the past is always present in executive coaching with a psychoanalytic perspective, and how compassion and curiosity unlock the unconscious patterns that keep clients stuck. You’ll also unpack his well-known “how have I been complicit” question, why “complicit” is different from “responsible,” and how shame and guilt derail real change. The episode also gets practical about coaching vs therapy boundaries, including when to bring in a therapist, and why coaching supervision for coaches (and strong referral networks) is part of the ethical job.


Key Learnings:

  • Use radical self-inquiry coaching to surface patterns without triggering shame: ask “How have I been complicit in creating the conditions I say I don’t want?” and follow it with curiosity about the hidden benefit (the IPO / intended positive outcome).
  • Tighten coaching vs therapy boundaries by screening for pathology vs non-pathology, and have a plan: build a therapist referral network and agree that the psychotherapist leads the treatment plan if one is involved.
  • Make coaching supervision for coaches non-negotiable: debrief intense client dynamics with a supervisor/peer group so you don’t get pulled into “doing it right” or hiding behind a rigid methodology.


Resources:


Episode Chapters:

00:00 Coaching vs Therapy Boundaries: When to Bring in a Therapist

02:12 What It Means to “Grow Up” + Radical Self-Inquiry Coaching

04:34 The “How Have I Been Complicit?” Question (Complicit vs Responsible)

09:00 Why Shame, Guilt, and Blame Block Change

11:22 Finding the Hidden Benefit: The IPO (Intended Positive Outcome)

14:05 Don’t Turn Questions Into a Script: Coaching Presence Over Methodology

16:20 Executive Coaching With a Psychoanalytic Perspective: The Reboot Venn Diagram

19:10 “Who Are You Really Serving Right Now?” and Ancestral Patterns

26:10 How Reboot Bootcamps Work: Safety, Container, Dyads/Triads

33:10 Pathology vs Non-Pathology + Coaching Supervision for Coaches

Transcript

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

Jerry Colonna: Sometimes our job as a coach is to continue to work and bring in reinforcement. I bring in a psychotherapist, I will say I am no longer the boss of the treatment plan, the boss in the treatment plan is the psychotherapist. And if the psychotherapist says, stop coaching, then you stop coaching. But if I say, there's a pathology here and I can't do anything about it, I'm in danger of making the client feel dropped. So this is why it's really important, when you take on a client, you have a moral obligation to that client. Are you well-resourced to do that? Do you have a network of therapists? Do you have a network of people that you can call? Do you have a peer group that you can talk to and say, holy shit, this thing is happening here? Tobi: Jerry Colonna is an executive coach rooted in the business and venture capital world, and yet his coaching practice is deeply informed by psychoanalysis. He says the past is always present, and also in coaching, not only in therapy but also in coaching, we can't ignore it. We demoed this idea very drastically on the last episode, where Jerry and I explored how the history of my father and even my grandparents influenced my unconscious patterns. On today's episode we look further into this kind of craft, unpacking Jerry's infamous questions for self-inquiry, why we can call a client complicit in creating the circumstances they say they don't want, but why it might not be helpful to call them responsible. We also look at in what ways my quest to deconstruct Jerry's methodology, for myself but also for you, might not be the way after all to become impactful Tobi: coaches, if we listen to Jerry. But if all of that sounds a bit cryptic, let's hear from Jerry himself.

Read the full transcript

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