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

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

So, Reboot, your first book, has a subtitle that says, the art of growing up. What does it mean to grow up?

Jerry Colonna

Well, one of the first conclusions I came to when writing the book, and I wrote of this in the introduction, was that better humans make better leaders. And there's a corollary here. What I mean by growing up is really more fully understanding who we are and how we are, and really connecting to the unconscious motivations that have shaped our lives, so that we are more in the driver's seat. There's a useful phrase, I use radical self-inquiry, and what I mean by that phrase is, it's the process by which the

Tobi

And what helps to facilitate this process? If I paraphrase it in my language, I would say it's a lot about understanding these subroutines that you mentioned in our previous conversation, understanding the inner beliefs that shape me, that maybe are not even my own originally but that I sort of inherited from previous generations. How do you, in your programs and coaching sessions, unearth these, dig into these, and help clients to understand these patterns and beliefs?

Jerry Colonna

Well, first of all, let me affirm what you observed. Yes, it's the process of using radical self-inquiry and deep, powerful questions to unearth things. As I've mentioned, my infamous question of, how have I been complicit in creating the conditions I say I don't want, is a perfect example of the kind of radical self-inquiry that is necessary to unearth the unconscious motivations. And to unpack that question just for a little bit, because this is part of the process here: complicit is different from responsible. I always point out that the word complicit is related to the word accomplice, and the accomplice in the bank robbery is the one who drives the getaway car, not the one who sticks up the bank teller. And this is important, because as we start to unpack things, one of the impulses is to become self-critical. I cannot believe that I do this stupid thing that I do. Self-criticism, just like guilt, shuts down the inquiry process and actually leaves us trapped in the subroutine. It's only by being compassionate and curious that we can understand that we are not responsible. Your obsession with being safe, for example,

Tobi

Yeah. So in the end, what you are saying is that one of your main tools in unearthing these beliefs is questions. And I think you are quite well known for a few of these questions. I just pulled it up here on a board. I think this is one of the most famous ones: how are you complicit in creating the conditions you say you don't want?

Jerry Colonna

Right.

Tobi

And I would love to unpack that a bit. You just pointed out it's a very conscious choice to not say responsible here, but to make it an accomplice, because that helps the client to not take the blame, and then not make this a conversation about blame.

Jerry Colonna

That's right. Blame, shame and guilt block the client from the inquiry process that is necessary to create the conditions for transformation. I'll say that again: blame, shame and guilt block the client from the inquiry process necessary to complete the transformation. All right, so you're right to focus on that word complicit. It drives me crazy, because this question bounces around the internet every day a billion times, and I wish I had trademarked it so that people would give me the credit. God dammit. No, just kidding. And almost every time I encounter it I almost have to explain yet again: complicit, not responsible. And the reason that goes on, Tobi, is that so much of the self-help literature and the self-help mindset is so focused on helping people see how they're responsible for things. It's misguided. It's well-intentioned, but it's misguided. The focus on responsibility is intended to give people a sense of agency: if I'm responsible, then therefore I have the power to change it. And that is true, but the problem is it directs the client in the wrong

Tobi

Yeah, so that's again about looking for the positive intention behind the behavior, and acknowledging that intention with empathy, and bringing us back to self-compassion.

Jerry Colonna

That's right. I think it's one of the people who developed NLP that I heard it first from. He used to call it the IPO, not initial public offering, but the intended positive outcome. There's almost always an intended positive outcome, even from our worst behaviors. In nonviolent communication training, which is also a very useful training, the focus is on the needs. What need are we trying to meet? We're almost always focused on a

Tobi

How do you bring up these questions in an actual coaching? You've written about them in your book, you say they float around on the internet. How do they find their way into the actual coaching journey, let's say, if not even the conversation?

Jerry Colonna

So you've already experienced some of my coaching, if you will. Notice how natural it is. I don't go in and say, what are the five questions that I have to ask here? The questions that I have written, that I write about, grew out retrospectively from examining what it was that I was doing in a coaching session. So, you asked, how does this come up? And, again, the coach's job, the coach's tool, if you will, is a well asked question. And behind the tool, the stance we take is one eye on the client and one eye inward, paying attention to what's going on. We're listening with empathy that is deep and profound, and then we ask the question that simply, intuitively arises from inside of us, not from the methodology. Ooh, I listened to Jerry, so I have to ask five times a day, how have you been complicit in creating? Stop. Do not turn Jerry's work into a methodology, please, for God's sake. Do not emulate

Tobi

Earlier you said you have a team of 10 coaches at Reboot. How have they been trained?

Jerry Colonna

In lots of different methodologies. One of the things I like about our happy little band of warriors is that there's a wide diversity of experience. There is some similarity in everybody, in that one way to think about it is, there's a Venn diagram that I think every good coach lives in, and the various components of the Venn diagram include some sort of spirituality, some sort of spiritual awareness. A deep and profound understanding of psychology. An awareness of business issues, because we are an executive coaching firm, and so being able to speak fluently the language of leadership and business is extremely important. And then the final piece of that Venn diagram, I would add, is a profound commitment to self-growth and self-awareness. And in that overlapping

Tobi

So, just recapping that Venn diagram you mentioned. You said business acumen, speaking the language of your clients, simply because you navigate in that industry. Then this deep commitment towards the art of growing up, for my own sake, doing my own work, and actually the awareness that this work is continuous and not completed.

Jerry Colonna

And the psychological sophistication, the fluidity around that. The coaching training, which is different. And the sensibility, whether it's mindfulness or a body centered approach, this notion that we are not always what we say, we're more often than not what we feel and what we do.

Tobi

Another question that I caught, I think it was in one of your email journeys, you have the self-inquiry email journey, that resonated was,

Jerry Colonna

You've been taking one of our courses.

Tobi

Yeah, if you want to call it that, at least I received

Jerry Colonna

Yeah.

Tobi

them. Taking and receiving is, yeah, you have to do the work.

Jerry Colonna

Yes, you do.

Tobi

Yeah. But another one that I actually did reflect on, and that I noted down for today, was also this: who are you really serving right now? And I think the resonance that I felt there is also going back to our previous conversation, in a way, becoming aware of what beliefs did I inherit. Can you take us into the origin and motivation behind this question?

Jerry Colonna

Well, if you unpack it a little bit, the operative word there is the word really. If you think about it for a moment, if I just say the phrase, who are you serving right now? We started our first conversation, you asked me about what my mission was, and I made the point that I could just spout off something that had no meaning and no authenticity. I could just say shit that sounds good. And the more practice you get at doing podcasts and writing essays for LinkedIn and blah, blah, blah, the more capable you are of saying something that goes viral. Oh my

Tobi

How has the awareness of this, who are you really serving, changed you?

Jerry Colonna

James Baldwin, the writer, said, not everything that is faced can be transformed, but nothing can be transformed until it's faced. Who are you really serving is the kind of question that forces one to face the things that caused the conditions in the first place. We cannot become the people we were born to be until we are willing to consciously create our own story, our own life. And so, by acknowledging that, like everybody else, I carry these ghosts, the ghosts of my ancestors,

Tobi

And that's exactly the point where I would like to dig in, because this kind of work, these kinds of questions, you worked on this a lot for yourself, and I assume now at Reboot, and in the bootcamps that you do and the coaching practice that you do, you also translate this into the transformation that the leaders that you mentioned would need. And certainly the business leaders that actually book a bootcamp with you. How does this process look for them? Do they get homework before they attend the bootcamp, to actually talk to their parents about family history? Or how do you make that very hands on and practical, this getting into this kind of work?

Jerry Colonna

So, before I answer your question, notice again the engineering mindset that you have, where you want to know all the steps. And we're going to blow it a kiss, because it's an important part of who you are, and it helped you get to where you are. And yes, there are, we do lay out pre-work. Right now we've got a bootcamp that will be running in March, and all of the attendees are doing something we've never done before: all of the attendees have been in a peer group since November. And so when they arrive there's already cohesion among the group. And some of the content of the camp is going to be classic Reboot book content, but some of the content will be Reunion work, which is all about relating to our ancestors. But I want to take a step back, because the first half of your observation and question, the jumping off point, was really about doing this work in service of others, of creating the conditions for others. And I want to bring your attention back to the first thing that you were asking me about in our first conversation, which is about my mission, and I referenced the importance of the Bodhisattva vow. Now, as long as space endures,

Tobi

Can you walk us through, on a high level, how the flow of a bootcamp looks?

Jerry Colonna

No. No, just kidding. Every camp unfolds slightly differently. I am a big fan, and it drives my colleagues a little crazy at times, of what I call emergent experience. If you listen carefully to retreat participants, just like you listen carefully to clients in a coaching session, you have to give them what they need in the moment. Now, that said, there is a sort of broad structure, and the broad structure begins with setting the conditions of the container. Nothing like this will work unless the container itself is safe. So you're establishing safety very early on. You are also establishing, there's a great line in The Wizard of Oz, the original movie, in which Dorothy turns to Toto, her dog, and says, Toto, I don't think we're in Kansas anymore. There's this moment where people realize they're not in Kansas anymore. And usually I say something like, welcome to bootcamp. Bootcamp is not, I call it bootcamp, we started calling it

Tobi

Yes. And of course I will dig in a bit more. So what I hear is, it's a lot about contracting, in a way, that also sets up participants to be ready to go deep, to be vulnerable.

Jerry Colonna

Yeah. So, understand that people apply to the bootcamp. There are a lot of people who want to treat it as a performative experience. We don't do that, we're skilled at this point at assessing that. And, I'll be honest, we get a lot of coaches who want to come to our bootcamps because they want to learn things. When I said before that it's not bootcamp unless the facilitators have their asses kicked: if we approach it from an intellectual stance, oh, let me see what Jerry does in a bootcamp, then you're remaining apart, and that's not acceptable.

Tobi

So the magic happens if also facilitators go beyond their comfort zone.

Jerry Colonna

That's right, that's exactly right. The minute it becomes routine or rote, I change the content.

Tobi

You mentioned the dyad and triad work. How does that look?

Jerry Colonna

Well, a dyad is two people doing work together, and they may do it in a partnership walk, or they may do it one-on-one facing each other. Triad means three people doing it. But the point is that we use each other as mirrors to create deeper exploration. To come to our bootcamp, you are committed not only to your work, but also to being there for others, to create safety. Again, borrowing language from Parker Palmer in A Hidden Wholeness, we have adopted a notion of what he calls double confidentiality. And double confidentiality works this way. There's the obvious confidentiality that every retreat does, which is, what happens in this retreat stays in this retreat, you are not allowed to reveal it. That's easy. More difficult is, if you and I are

Tobi

Yeah. Maybe coming back to what we talked about earlier, about coaches sticking to their safe space, the methodology they learned. What I also noticed about your work, and this looking back at family heritage, the beliefs we inherited: for me it goes beyond what I learned coaching is, in the sense that it looks into the past, in a way where you sort of enter therapy space. What would you respond there? Where do you draw the line between therapy and coaching, and what we as coaches are supposed to do?

Jerry Colonna

Yeah. So, notice the supposed to. There's a right way, there's a wrong way, and there's a way that works. Notice how scared coach training programs, and the coaches who train in the coach training programs, get when we start to approach this. But I want you to know something. Why are you drawn to my work? You, as a coach, why are you drawn to my work?

Tobi

Your story resonated. The family, the parallels I see in our family history, maybe.

Jerry Colonna

Yeah. But as a coach, what makes it fascinating, the way I coach?

Tobi

And I think, for me personally, also the overlap between entrepreneurship, tech and coaching, personal development, therapy.

Jerry Colonna

I was asking, and I don't know if this is true for you, I thought it might be, but we'll see. I was asking because what my experience has been is, the more I've spoken about the way I coach, the more I encounter coaches who say, yeah, I want to do that. So you're right, there are a lot of training programs that say, don't go there. They create this false dichotomy that you yourself used, which is the past. Well, that's the realm of therapy. And I believe it's a misunderstanding of Carl Rogers, it's a misunderstanding of Martin Seligman, the roots of modern coaching. It misunderstands, because the fear of the coach training programs is, we're going to break the client. And so what happens is, the client is dropped, the client is left in this zone. A really brilliant coach who best epitomizes what I'm talking about is Manfred Kets de Vries, who was the original CEO whisperer, who is a psychoanalyst and executive coach. Read his book, The Leader on the Couch. Read his book, Coach and Couch. What are we in this business to do? We're in this business to effectuate transformation by any

Tobi

And how do I recognize this pathology?

Jerry Colonna

Ah, that's a great question. That's a really great question. It's a good thing you have a supervisor to talk to about what's going on. I'll give you a quick story. Years and years ago a very famous founder of a really important internet company came to my office with his number two, and they wanted coaching. This is an office I had in New York. And I sit in a chair, and there's a little couch and the couch can seat two people, a little sofa, and then there's another chair on the left hand side. And the founder in question comes in, sits right in the middle of the couch and sticks his arms out, preventing his co-founder from having a seat. Session ends. I call my analyst, to act as supervisor, and I was like, holy shit, this experience. And she said, how did it feel, being annihilated by a narcissist? Because that's what was going on. There are certain aspects of it, I could work with that client. Unpleasant, but I could work with that client. But when that client's narcissism also morphed into bipolarity, and he was a high functioning, fast cycling, up down up down bipolar, I called a friend who was a psychoanalyst and I said, I need your help. And then we got him a psychiatrist, got him on medication, created some stability, and I

Tobi

So in a way it comes back to reflecting a lot about what is happening in your sessions, by yourself, with a supervisor.

Jerry Colonna

That's right.

Tobi

And making sure you have that network.

Jerry Colonna

The work is not about saying the right thing. It's about presence. It's about how you hold yourself as a coach. Irvin Yalom, the psychotherapist, has this great quote in one of his books, The Art of Psychotherapy, in which he says, the healing is in the presence. The healing is in the presence. The healing is in the presence. He repeats the line three times. The same thing is true in coaching.

Tobi

Thank you. Maybe to close off, as we talked a lot about questions: what is a question that you, from today's perspective, would ask Jerry the young coach from 20 years ago?

Jerry Colonna

That's a good question. I don't know, let me think about it for a second. Why is it so important to you to heal people? Now, in hindsight I know the answer, but I think 25, 30 years ago, if I'd spent a little bit more time with that question, it might have been helpful for me. That said, I have thoroughly enjoyed my journey, even if it's kicked my ass at times. It's one of the many ways in which I feel blessed, to have had this journey all these years.

Tobi

Thank you.

Jerry Colonna

You are welcome.

Tobi

That's it with Jerry Colonna. If you want to go further with Jerry's work, I guess the best starting point is his books, Reboot and Reunion. And you can also go to reboot.io, where you can find the self-inquiry email course that I also took in preparation for today, and where you can find some of the questions we unpacked. If you missed the first episode with Jerry, then I can highly recommend checking out the live coaching demo there, it really makes some of the themes of today much more practical. And if there's one thing I've taken away for my practice as a coach from the conversation with Jerry, then it is the importance of self-reflection and of supervision for us as coaches. So, how fitting that my guest in two weeks is exactly an expert in this. We are doing an actual supervision demo, leveraging the power of pictures for us as coaches to reflect on our coaching. If you want to check out the online coaching and visualization platform that we also used on today's episode, go to metaFox Online; with the code IMPACTFUL you can even get three months of entirely free pro access. That's it for today. If this conversation made you think, share it with a coach in your life, or drop me a message on LinkedIn or at tobias@metafox.eu if you have any feedback. You can of course also leave comments on your favorite podcast platform. And with that I finally close off. I'm Tobi, co-founder of metaFox. All the best