🚀 Breathe.



“The task that exists before all of us is to use the challenge of leadership to grow up. Those who don't use the challenges of leadership, to complete the process of becoming a better person, a better human, miss out on an opportunity.”

In this episode

In episode #71, Jerry Colonna teaches you how to attain radical self-inquiry through the challenges of leadership. 

Jerry Colonna is the CEO of Reboot.io and author of  “Reboot: Leadership and the Art of Growing Up”.

In this episode, we talk about asking questions as a leader and how to examine reasons and choices in a unique way.

We also talk about how to free yourself of negative behavior and dive into a lot of concepts and ideas like ghosts in the machine and #GetCurious. 

Tune in to this really unique interview and feel your manager mindsets expand as Jerry asks questions that truly allow you to become more self-aware. 

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Being a young manager


Honesty and insecurity


Answering your own questions


Developing true grit


Radical self-inquiry


Conflict at work


You already have the answers



Aydin Mirzaee (Fellow.app)  00:06

Jerry, welcome to the show. 

Jerry Colonna (Reboot.ai)  03:37

Thanks, Aydin. Thanks for having me.

Aydin Mirzaee (Fellow.app)  03:38

Yeah, this is gonna be fun. I just mentioned to you that I am a big fan. I listened to the audiobook version of your book twice. So I have many, many questions for you today. But you have had quite an extensive leadership career and you’ve coached a lot of leaders, you run a popular boot camp called reboot. You’ve been a venture capitalist. You’ve been in the startup game, you’ve been a writer, you’ve done many, many things.

Jerry Colonna (Reboot.ai)  04:12

I have range.

Aydin Mirzaee (Fellow.app)  04:13

you have range, that is a very good, good way to describe it. There’s a lot that we’re going to talk about. But maybe one place where we can start is when you first started leading teams as far back as you can remember when that happened, what would you say if you were to just analyze the way that you worked back then what were some of the early management mistakes that you think you made?

Jerry Colonna (Reboot.ai)  04:39

How much time do you have? I would say if I look backward, first well my first exposure was probably when I was a teenager, acting as a foreman on a locker repair crew that would descend each summer and into local school districts and fix school lockers. But I’m going to not talk about that period. I think the more interesting period was probably in my early 20s. When I was first a reporter, then editor, and then eventually one of the managers at a magazine, the magazine was called information week as a print magazine focused on that technology sector, the brand is still alive as a web-only enterprise. And I think that a lot of the mistakes I made were very, very familiar to me now as a coach because I see people doing the same things. So for example, one of the things that popped out at me immediately as the memory was I was very young, as 24, I think, when I was promoted, first up the ranks as a reporter, and then eventually the number two editor at the magazine. And most of the people who reported to me were more senior in age, more experienced, knew more about the work than I did. The result of that was that I was deeply insecure about judgment calls that I had to make. And I forgot or lost touch with the fact that the folks who promoted me to people, Becky Barna and Laton McCartney promoted me because they saw in me that I had a view of the where the magazine should go. And so I probably leaned a little too heavily at that time on having all the right answers as a way to lead and the brittleness that comes from believing that to be successful as a leader, you had to be the smartest person in the room that led to a whole bunch of mistakes that I’ve made that, you know, if I could go back in time, I might have done differently.

Aydin Mirzaee (Fellow.app)  06:55

One of the things that you just said was, you know, you didn’t have all the answers. And I think this is a topic that you talk a lot about, which is leaders don’t need to have all the answers. What should people do when they, I guess, come across a situation where they really don’t know what to do.

Jerry Colonna (Reboot.ai)  07:14

They should be honest. And say, I don’t know what to do. This sounds radical when I say it, but it’s actually pretty simple. It’s hard. It’s hard as hell because it taps into all the insecurities that we have. And again, to use myself as an example. I was so insecure about coming across as someone who didn’t have the answers, and therefore was not justified to have been promoted over these people who had many more years than I did experience, right? There’s something really powerful when about when someone who has been tasked with leading an initiative says to the team, I’m not sure what to do. What do you think, see, I’m not abdicating your responsibility. When I do that. I’m not abdicating your responsibility to make the decision. But I’m pulling down the bullshit mask that says I have all the answers. No one has all the answers. It’s it’s an absurd expectation that we carry into those first leadership experiences. And we do that because we are convinced that the team will no longer support us as a leader. If we don’t have the answers. The last thing I’ll say about this, in this moment, is to is a breakthrough for me was early on in my 20s, I started to gobble up leadership books. I read everything I could get my hands on. And you know, working for a magazine was really great, because people would send us books to review. So I just took it upon myself to read and review everything. And I remember back then reading I believe it was Peter Drucker who said, essentially that a leaders job is to ask the right questions. let’s acknowledge how simplistic that is. And yet how profound it is. It’s antithetical to every projected ideal that we have of what a leader is supposed to be, at least His job is to ask the right questions. What? Right, and I will go further ask questions, the answers to which you don’t possibly know what think about how liberating it is. Think about how frustrating it is to be led by someone who doesn’t know as much as you do, or pretends that they don’t. And then think about that experience of someone who has more power than you do. Turning to you and saying what would you do think about what that does for the team.

Aydin Mirzaee (Fellow.app)  09:42

You know, when you when you put it in those lights, especially putting yourselves in the other person’s shoes, someone who has more power asking you but then also playing you know, if you’re in their shoes, someone who really doesn’t know pretending that they do it. You know, it’s It will come across and people do know, I’m going to ask you a question. And then and then I’m going to revert back to something that you talked about in the book. But should we make people? Should we? Should we promote people to be in charge of people? Who are others who are more experienced than them? One of the questions, you know, often is that like, you know, when when you’re in a situation where you are in charge of, or either from a management stance in charge of a team, and some of that team is maybe a lot older, a lot more experienced, should we avoid putting people into those positions? are, are tread carefully when doing something like that? Or is that something that is we should just catapult people into doing if we feel like they are able to make decisions or make the type of decisions that that we want them to show? I’m going back to when you got promoted to run the magazine? Do you think like looking back on it, that was the right move to have promoted you into that position, being younger and say, let less experienced and others in that field? 

Jerry Colonna (Reboot.ai)  11:09

If you have listened to me on various podcasts so you know what I’m about to do? You may not have expected it. But this is the moment. Okay, so I find your your question really fascinating. And I promise you, I will get to an answer. But I want to know why you’re asking the question. So let me just finish the question. What story? Are you telling yourself? About the scenario? That leads to that question.

Aydin Mirzaee (Fellow.app)  11:38

I’m thinking about an example, there is a decision to be made where we could have a situation where just like you were promoted to run that magazine, that there would be a situation where I would have the ability to do something very similar. So I’m just trying to think about like the circumstances under which like that decision was made to get you to run the magazine.

Jerry Colonna (Reboot.ai)  12:03

So you’re empathizing with the folks who promoted with me. And you’re nodding. And so and and the thing about empathy to remember, the thing to remember about empathy is that it’s rooted in our own experience. And so what I see you doing right now is, is either imagining yourself in that situation, or actually recalling being in that situation.

Aydin Mirzaee (Fellow.app)  12:28

Yeah, yeah, definitely

Jerry Colonna (Reboot.ai)  12:30

The question you’re asking what in effect was, is it the right thing to do? Yeah, I want you to step into a place a different place. Let’s imagine it was the wrong thing to do. Notice how that feels. Step into your own leadership. You’re the LFA, you’re the boss. You’re the one with the power. And you’ve made a decision to promote someone who has less experience over those who have more experience and it turned out to be the wrong decision. How does that feel?

Aydin Mirzaee (Fellow.app)  13:04

Not that bad. Most decisions are not irreversible. 

Jerry Colonna (Reboot.ai)  13:08

Okay, so what just happened was the fearful part of your brain got quieted by the prefrontal cortex that explained to itself Don’t worry about it’s gonna be fine. What I want you to touch back into that fear. Because that fear is really, really interesting. The fear of a leader making the wrong decision is related to the belief that the leader has to have all the right answers. Can you see that? 

Aydin Mirzaee (Fellow.app)  13:41


Jerry Colonna (Reboot.ai)  13:43

It’s two sides of a similar position of the same coin, which basically says, You better be right. Because if you’re wrong, you’re a fuckup. And what’s really, really interesting as the minute I brought your attention to it, your prefrontal cortex kicked in and said, It’s okay, don’t worry. No decision is irrevocable, you can fix it after the fact. So notice something. I never answered your question.

Aydin Mirzaee (Fellow.app)  14:12

No, you didn’t.

Jerry Colonna (Reboot.ai)  14:13

What’s the answer to your question?

Aydin Mirzaee (Fellow.app)  14:15

The answer to my question is, there is no right answer. I think

Jerry Colonna (Reboot.ai)  14:20

Look at that. In fact, bringing your attention to the wish for the right answer starts to open up really interesting avenues of inquiry, like, what am I so afraid about? consequence? Oh, I made the hard decision. Because now go back to the answer. Sometimes it’s the right thing to do. As it turned out, and in my situation, who years after making that promotion, our magazine went from being number five in a five magazine market to number one, Was it me? No, there was a whole bunch of decisions that they made and a whole bunch of decisions that I made the People that resented me being promoted, ended up liking me. And some of them remain friends with me to this day. So on the whole not a bad decision.

Aydin Mirzaee (Fellow.app)  15:12

That’s awesome. I wanted to ask that question because then I was going to flip it and go back to something that you talked about in the book, which I relate to, which is, I think you have this experience with a lot of clients, I feel like I would be one of those types of clients that would maybe did really well in school. Got A’s and A pluses. And so we grew up thinking that, you know, there there is a right answer, there’s a played well, and yeah, for everything, but but it turns out that, that that’s not the case. And it’s a very interesting you know, in thinking about and I’ve thought about this before as well, which is like you know, when you get into university and you’re in you’re going to school, like there’s a very specific set of things that you need to do and if you do those things by the metric of you know grades like there’s a very specific outcome it’s all like there’s not much that you need to necessarily innovate on but the second that you’re out of there like there there all of a sudden is no playbook so how do you how do you get people to kind of understand this because I mean, it sounds simple but it but I think people but yeah, I mean even in this case, which is like when I asked you, you know, how do you make the decision to promote someone into such a role? I mean, effectively I’m asking you for the for the answer.

Jerry Colonna (Reboot.ai)  16:40

Yeah, you were and and I think that you’re, you’re wise in making the association with the way we’ve been socialized from childhood right in schools and most schools are a good example of what we’re talking about where there’s a systemic approach to things that lead to the output right and what’s the output that we want the pot of gold at the end of the rainbow and happiness and sunshine, milk and honey for the rest of our lives? What’s the god-awful reality? It’s a lot more difficult than that. You could have a pot of gold and be miserable you could have no happiness and no pot of gold. Well, that’s confusing. But I did I I did all the right things. I agenda the right clubs I you know, I took the right classes. I got the right grades I did you know, I wore clean underwear every day. And in case I got into an accident the way my mother warned me, right, I did all the right things, and I still struggle. And, and one of the really profound challenges is that human nature is when confronted with that reality, turns the blame inward. Oh, everybody else must have figured it out. So then that little Whispery voice that lives inside of us that says you don’t have a fucking clue. turns out to have been right all along. So I’m going to give you some relief. So why don’t we know what to live because the world is much more mysterious than that. Good things happen to bad people, bad things happen to good people all the time. As one of my B Buddhist teachers once said at a wedding, no less. Pain is not punishment, pleasure is not reward. See, we’re organized to think that if I do the right things, I will be what? happy forever. What’s lost is the opportunity to develop True Grit, the opportunity to develop resilience, which in my mind is the most important character trait of any leader but more important, the most important character trait of any adult. Because as I wrote in the book, True Grit resilience leads to equanimity worlds is a piece of shit and I’m okay. The world is great. And I’m okay. That’s what we really want, is the ability to feel okay, regardless. 

Aydin Mirzaee (Fellow.app)  19:24

You know, this, this makes a lot of sense. And another thing that that you you mentioned triggered this part that you talked about in the book. So you said that, a lot of us think what we want is this thing that is just going to make us happy forever. And then there is this part where you also talk about I think it might have been another Buddhist teaching where things are always falling apart. And, and it was really funny. I think you mentioned that the you finally understood it. And then the teacher said, Well, your understanding of this is also falling apart, which is really funny. But equanimity. So that’s what people really want, which is that no matter what happens, you know, they’re going to be okay. The thing that I wanted to chat about which which is was really interesting, and I thought it was a very novel approach, because just going back to this, you know, people want a playbook of how to be a better leader, how to be a better CEO, how to run, run a team better. And I think like one of the the core lessons that I’ve taken away from, from from anything that I’ve learned from you is that it’s about learning how to almost grow up first, could you maybe describe what it means to grow up as a leader and like, why that’s the first thing that needs to happen before you can become a great leader?

Jerry Colonna (Reboot.ai)  20:53

Well, actually, what I would say the way I would frame it is that the task that exists before all of us is to use the challenge of leadership to grow up. So it’s not sequenced, the way you described it, you don’t have to grow up to be a leader. But those who don’t use the challenges of leadership, to complete the process of becoming a better person, a better human, miss out an opportunity. And I’m actually going to link it back to the first observation that you made. And that teacher that you’re referencing as Pema children, but it’s not. And she was teaching them on a Buddhist concept called impermanence, which is this notion that things are falling apart all the time, right. And impermanence is a really important and useful tool to understand or concept to understand. Because behind the belief that there’s a playbook is a belief that there’s a right way to do everything. And it’s just a matter to figure it out. There’s a puzzle problem is, as is often the case in businesses, you craft a business plan, you think of every contingency, and then some crazy shit happens. Right? And you didn’t plan for that. And so, resilience in the business, is the capacity to withstand the unplanned for event. And so if we go into the planning process, with the acceptance of impermanence, we plan our best. But the real effort is in building the capacity to withstand the changes that occur regardless. Right? That’s the real leadership capability when we are capable of doing that. And applying that not only to our job as leaders, we then get to complete the process of growing up. So for example, ou asked what is a grown-up, a grown-up, in a sense. And by the way, I don’t think we ever finished the process of growing up, I think we’re always in the practice of growing up. Grown-Up uses every experience that there have that happens to them to go deeper in their own development. So I was just talking to a client before a call. And we were talking about the three or four people who are most upsetting to that person. They’re an investor. So it’s a couple of CEOs and portfolio companies, and it’s a partner in that kind of thing. And I asked a simple question, why does that behavior upset you so much, rather than going down the rabbit hole of telling me again and again, again about how awful the behavior is? We use the question to say, why is that so upsetting? And we ended up him being five years old, trying to take care of his mother, who was miserable, no matter how much he did. That’s that growing up. That’s that using the challenge, to no longer repeat the pattern of being a jerk, because my client can be a jerk to people. We use that challenge to unpack Who am I as a person so that I can then be in charge of my own life. And not, as the great psychologist collagen would say, allow the unconscious to direct my life and to call it fate, right? That’s what I mean by that growing up process, who am I? How am I wired? Why do I do the things that I do? So that I can then choose? The way I’m going to respond to the world.

Aydin Mirzaee (Fellow.app)  24:58

There are other things You also talk about which are which are kind of related. You know, the first first point is you use the use the terminology radical self inquiry, you know, self inquiry to me make sense. What, what is? What is the word radical in this particular case? Does? Does it just kind of mean, you know, just trying to go deeper and deeper? Like, how do you view self inquiry versus radical self inquiry and how they’re different? Well,

Jerry Colonna (Reboot.ai)  25:32

I call it radical more often than not, because we typically don’t do the work. A good example, to go back to what I was just talking about. Somebody pisses you off. You call a friend? What do you want to talk about? How awful the other person is? You never really want to say, Who does that remind me of? Why is that challenging to me? What other feelings does it come up with? We don’t ask those questions. We like to live comfortably behind the mask that says that john Paul Sartre once said, all other people are, Hell is other people. Right? Hold on here, you’re somebody else’s other person. You’re somebody else’s awful person. So maybe what we should do is use the experience of being triggered, to radically enquire within and say, remember the question from the book? How have I been complicit in creating the conditions? I say, I don’t want. Right? classic example. You have a colleague, you’re the CEO, you have a colleague who pisses you off all the time. My question is not how do you change that person’s behavior? My question is who hired them? Right? And you’re smiling? Because that’s the important question. And why have you not fired them? Oh, there’s a benefit to having that person there. What? That’s interesting, right? That’s what I mean, when I say it’s radical, it’s because we don’t do this, we don’t train ourselves to strip away mass. We just get habituated in our patterns, and we just, everybody’s awful all the time. is much more interesting, when you ask those questions.

Aydin Mirzaee (Fellow.app)  27:31

you will definitely learn a lot if you if you did that more often, you know, the the other term that you use in the book, which I really enjoyed was a Ghost in the Machine. And of course, like this, this comes from the software world where you have sub routines that are, you know, very, very old, you know, they somehow still exists in the software, they cause strange behavior. And I guess like a lot of these patterns that you’ve developed, like ways heuristics that you may be subconsciously use to make decisions. are, you know, like, the story that you said, when you were five years old, and something happened and that has influenced it’s, it’s a identifying what those are? And then asking yourself if those are actually still useful or not? Yeah,

Jerry Colonna (Reboot.ai)  28:20

I mean, I’ll take it back. Even one level, it’s radical to even acknowledge that there are subroutine running your life, right? Because we just presume that those are facts, here’s, here’s a good example. Money, if I had enough money, I would be happy. I that’s a that’s an assumption. Or here’s another one, that’s a contradiction. The pursuit of money is evil. Now, if I just poke on either one of those, and ask someone about their family’s relationship with money, all of a sudden, we start seeing the roots of all the decisions that they make, which career did you choose? Why did you choose this job versus that job? Right? And if what we’re trying to do is unpack and awareness of who we are and why we behave, how can you do that without understanding the basic input opera input-output system, your BIOS that defines who you are? Right? Another one would be, anger is a bad thing. And here is a good thing. Haber has no quality, it just is anger. But when you start to examine these things, you start to understand the reasons behind the choices that you’ve made. Why did you hire that person? Why do you maintain that relationship? Why do you repeatedly date the same person again and again and again, even though their names change? Why do you find yourself working for the same company even though you work For different companies, that’s all part of that what I refer to as radical self-inquiry process, really Trump’s starting to unpack those things.

Aydin Mirzaee (Fellow.app)  30:09

Yeah. And some of these sub routines can be useful to right. Not all the ghosts need to be gotten rid of. But it’s important to understand what they are.

Jerry Colonna (Reboot.ai)  30:19

Yeah, and I’m glad you made that point, it’s really easy to believe that the belief systems, which is what we’re referring to, and I call them, the ghosts in the machine, are somehow bad and need to be exercised. Now, in fact, the reason that a lot of these beliefs belief systems persist, is that they were successful. They worked, they got you out of the situation that you were in, that first formed, you might have been five and feeling powerless. And so the way you made sense of the world is to believe that x happens and y happens. Okay? And then if I repeat that behavior again, and again and again, then that makes sense. The issue, as you point out, is, when we get to chronologically adult ages, what happens is many of the belief systems, we start out, have grown. But we don’t question. We just live with the conflict that gets created. So it might be a conflict with a romantic partner who’s, you know, who kicks you off? Because they spent $500? on some gift? And don’t you understand money doesn’t grow on trees, right? And all of a sudden, we find ourselves, you know, quoting our father. Right? And so not only are you not five years old anymore, but your partner isn’t your mother, who was yelled at by your father.

Aydin Mirzaee (Fellow.app)  31:52

Some of these, you know, when it comes to some of some of these belief systems? How hard is it to replace them, like one one is to exercise them, like you, you mentioned? But if, if you know your environment, kind of program some of these into you, like, Can you also change them or instill new ones, you know, new ones, like, I am a great leader, for example, or things that instill confidence or will make you more successful

Jerry Colonna (Reboot.ai)  32:26

You’re asking a good question. And so it’s a two-step process, this kind of transformation that we’re talking about, it’s a two-step process, the first thing you have to do is recognize that the sub routines are up. It’s critically important. The second thing you want to do is ask how do those sub routines continue to serve you? Or do they continue to serve? Because very often, they’re very useful. The third thing would be to say, well, what’s true now? Right? So I might have had a sub routine that says, anger is dangerous, therefore, anytime I’m angry, become anxious. Right? And then as an adult, I’m walking around anxious all the time. Oh, wait, if I talk about what’s pissed me off, maybe I won’t feel anxious. Okay. But now what’s true, is that I am no longer as powerless as I once was. Right? So I would shy away from the notion of replacing one set of programming with a new set of programming. What I’d rather do is have a kind of more adaptive learning system that doesn’t require so much programming that just says Hi, my ability to be discerning about certain situations, matches my chronological age, aka wisdom. So when faced with Should I promote this person or not? Well, what’s the rule? No, no rule. Look at the situation. What’s going to happen if I promote this person and what’s going to happen if I make a mistake? That’s discernment.

Aydin Mirzaee (Fellow.app)  34:12

Yeah, you know, it makes sense. One of the one of the things that comes to mind is when you are going to make a decision and it’s true that there are no right answers. But sometimes it is helpful to look outside and look at examples to almost like learn one what is possible and are their things that can be learned but I think like it’s what you said, which is that every situation is unique, and you still have to be adaptive, and you can be informed by other situations, but you have to, like not use it as a playbook. Because like every situation

Jerry Colonna (Reboot.ai)  34:51

Well, that’s right. And you know, the human brain evolved to use fast pattern matching to survive. Right, so I come to an intersection, I’m walking across the street, I see the sign, flashes green and walk. The Fast pattern match tells me it’s safe to cross the street. That’s a very useful tool, and a card turns the corner and speeds around the corner and knocks me down. Right? the sermon would say, even though the light turns green, look both ways before you cross. Use your adult brain to figure things out. Right. And so we use the fast pattern matching for exactly what it’s designed to do, which is to make life a little bit easier. But don’t rely exclusively on not to run your life to operate the life. That’s when you can get hit by a car.

Aydin Mirzaee (Fellow.app)  35:55

Yeah, it’s so much of us run so much of our lives in an autopilot. And sometimes it’s it’s really nice to start to be aware of the things that you’re doing and actually experience life to its fullest. Well said. [AD BREAK BEGINS] hey there before moving to the next part of the interview, quick interjection to tell you about one of the internet’s best kept secrets, the manager TLDR newsletter. So every two weeks, we read the best content out there, the greatest articles, the advice, the case studies, whatever the latest and greatest is, we summarize it, and we send it to your inbox, we know you don’t have the time to read everything. But because we’re doing the work, we’ll summarize it and send it to your inbox once every two weeks. And the best news is completely free. So go on over to fellow dot app slash newsletter, and sign up today. And with that said, let’s go back to the interview. [AD BREAK ENDS] You know, the thing that I wanted to also chat about and, you know, maybe part of this is, you know, learning to grow up to be able to lead better, or at least, at least understanding why some of us avoid certain things like conflict. But some of your you know, you had an article on medium, which, which talked about this a little bit more. And you said, conflict avoided is conflict postponed. And so, you know, the question is, like, are you? Are you saying that, when you sense that there might be a conflict, you should just go ahead and have it? Or have you think about that.

Jerry Colonna (Reboot.ai)  37:30

I think you should get curious moments of conflict can be scary. And if we’re socialized as children, that conflict, and anger might lead to yelling, and other forms of violence, we’re going to avoid them like the plague. Okay. And yet, conflict within organizations is really interesting. Sometimes conflict occurs because two people are acting from their, their, their lesser selves, they’re acting from their own sub routines. But sometimes there are genuine disagreements about ways forward. When we avoid the conflict, not only do we kick the can down the road, and ultimately have to deal with conflict anyway. But we have we miss the opportunity to really go deep and be curious, see if we’re brave. In those instances, we get to examine what the various positions are, that are in conflict, and then lift up and out of the conflict, innovation. This there’s a tight correlation between positive conflict within an organization and high innovation, because high innovation innovation requires changing things as they are. And there’s almost always somebody invested in keeping things exactly as they are. So this conflict, right, but if we approach all conflict as a source of fear, then what ends up happening is we actually stifle innovation. And the most innovative thinkers in our team will leave because they like the new. So conflicts are really, really interesting area to sort of examine what’s actually happening within a team. What are the suppositions? What are the sub routines that sort of are the unspoken values of a team right? The value may be within the team. The spoken value may be we’re committed to transparency. The unspoken value is we walk on eggshells around people’s feelings, because we Want to hurt people’s feelings? Right, and there’s a conflict, then they’re unnamed, because it goes on resolved.

Aydin Mirzaee (Fellow.app)  40:08

You know, I think this concept makes a lot of sense in other ways as well, one of the questions that you brought up just earlier is, you know if you don’t like this person, or this person is not working out in the organization who hired them, which is a good question. But be, you know, why not fire them. And so and that’s a firing firing is in general, not very easy, ever. But a lot of it is, is what you said. And it just goes back to this concept of, of conflict, because it’s the fear of, I mean, it could be many fears, it’s fear of, you know, hurting the other person, it could be fear of, you know, what, if you made the wrong decision, what are the repercussions? It’s all these different fears. And

Jerry Colonna (Reboot.ai)  41:06

Let me expand upon that, too, because I, you know, I was sort of tongue in cheek when I said, you know, who hired them? If you have a colleague who isn’t working well, in the position, it’s such an interesting opportunity to sort of explore Well, how did they get hired in the first place? What was their expectation of the job? How well written was the job description? How well discuss with that were the expectations? What kind of feedback? Was the person getting all along? How have they been responded to? Right? So grown-up leaders, if you will, use those instances, to unpack the processes to unpack the value system has spoken and unspoken, to really extract? A better way to do this, there is that there is an assumption behind the colleague who isn’t working out, which is, in psychological terms, we’d call it splitting, where someone is either all bad or all good. And the truth is, almost no one is all bad or all cut. More often than not a colleague has to move on because they were the wrong person for their job. Whether it be multiple people who are responsible for that error, including the people who made the hire in the first place. So what was broken about the process that allowed the wrong person to be put into that position or be promoted that position? And is there anything that we need to change about the process to make the system to make the organization more resilient and healthy, and less toxic? Do you see what I’m doing here? It’s like, I’m trying to extract out what are the lessons? This is a kind of radical self-inquiry applied at the organizational level? Right? It does not blame. I’m not saying Well, you’re no you made a mistake. Your fault you hired him. It’s like now what was going on? Oh, well, you know, in the in the story that I tell him a book about, you know, the CEO upset with his very greedy head of sales. Right, what I like to say is that that head that CEO outsourced to a willing participant, their internal greed, their need have all the toys, and then they complained that they had a greeting head of sales. Well, of course you did, because you didn’t understand your own have all the toys to have all the marbles on the board. And the result was you had to find somebody else who could carry that because that was inappropriate. That was politically incorrect. To say I’m greedy, saying someone should stand up and say I’m greedy and greed is good. As they said in that old movie Wall Street where it’s like what is greed? Oh, it’s fear about not having enough named that talk about that. Be free of negative behavior.

Aydin Mirzaee (Fellow.app)  44:14

Yeah, Jerry, this is this is awesome. It gives me a new motivation to not be upset or rather get more excited anytime that there is something potentially upsetting or I have any emotion which is which is not at all positive to inquire to see what I can learn about it. But you’ve really demonstrated very well how you could take as simple as situation and really dig in and learn so much from it. My question is and like this is maybe like a very tactical thing is you know, the thoughts that go through my mind is a this is very useful. And if I did this for like in any amount, if I did it more than I would get a lot out of But the question is like, how do you decide where to spend your time to do this kind of radical self-inquiry, and like where you should allow yourself to go on autopilot? You know, this morning as I was on my run, I was thinking about a conversation I had like three and a half years ago, and I and I just like recounting it, it made me learn something new about what might have happened that, you know, during that conversation, but if I did that, about every conversation, I would probably also learn a lot. But how do you decide where to focus your attention? And like, where do you do this self-inquiry on?

Jerry Colonna (Reboot.ai)  45:35

I love the whole question and the setup to, and congratulations on having a really good meditative moment. This morning, when you were running that awesome job. Because you didn’t set off on the run thing. I’m gonna think about that conversation. It just arose, right? And in the arising, you got curious. And that curiosity is really powerful. Okay. So I won’t coach you on this, but I’ll say the feeling I had behind the question, as you formulated it, is, it sounded like something that people often will will surface which is kind of goes like this, well, this is all well and good. But if I spend all my time doing this, I’m never going to get anything done. And I’m going to be trapped in some sort of self referential do loop, and never ever be able to do it. You’re laughing so close. Oh, hang on. All right. Right, right. Okay. So um, you know, what I would say is now, to be clear, I’m wired, I spent a lot of time journaling, I journal every day, this is the these are the kinds of things that I journal on, for me. And then when I put my clothes, my journal, you know, it’s still working in my unconscious, but I’m not expending a lot of energy doing that. Here again, in moments of high emotional energy. I passed on sad, I’m super happy. Those are beautiful moments, or I feel shamed, or I feel like I’m ruminating on things. Those are all moments. They’re all think of them as invitations to inquiry and responsive, which is to hashtag get curious. Why am I so upset about this? I mean, I had a similar incident that just happened this weekend, I was in conversation with someone their reaction triggered something in me. At the moment, I didn’t know what was going on for me. I just knew that I had to step away. And the next morning, I did a little bit of an emotional inventory. And I said, Okay, what were the feelings and the first feeling was surprise, then the second feeling was a threat. I didn’t anticipate this, then the next feeling was helpless. I can’t do anything about this. boy do I hate feeling helpless. So then I felt the anger. Because I don’t like feeling helpless. And so then the feeling was I gotta get out. I gotta leave. And I realized in this space, that that pattern is a big domineering pattern in my life. And I respond to a lot of situations like that. Now, since Sunday, when I wrote this out of my journal, I’ve seen this pattern shot two times. It’s now only Wednesday. And now that the pattern shows up, I kind of laugh. It’s like, Oh, wait, wait, there’s nothing threatening about being surprised. I just got surprised, right? So that, that moment, that sequence, probably going to be really, really useful for me in the future, to lower the stress the distress that I can feel in certain certain situations. So the long-winded answer to your question. Use discernment. Consider it a tool. And nearly every opportunity is an opportunity for growth. You know, I remember one time writing to one of my Buddhist teachers about being stuck in a middle seat on an airplane on a long flight two or three seats on the side, and I was stuck in the middle and I’m tall I am a big guy and my Buddhist teachers words kept coming to mind everything is workable. Everything is the middle seat on a shitty flight. All right, it’s workable.

Aydin Mirzaee (Fellow.app)  50:04

Jerry, so many lessons. So many things that we talked about we, you know, obviously, want people to check you out reboot.io. And, and of course, of course, the book. But one of the questions that we ask every manager and leader out there that comes on the show is, you know, for everybody else who’s constantly looking to get better at their craft, are there any final tips, tricks, resources, or final words of wisdom that you’d like to leave them with? Sure.

Jerry Colonna (Reboot.ai)  50:38

Probably the most important thing is that you already have the answers, right? If you go quiet within yourself, you know the answer, even think about what I did with you before. I may just slow down. Ask the question again. And you’re right, the dancer. Right? That’s more often than not I see leaders struggle with accessing the answers that they already have inside. And whether it’s myself or my colleagues at the company or any good coach, good coach will help you understand that you actually have the answers. You just have to be brave enough to access them.

Aydin Mirzaee (Fellow.app)  51:16

That’s great advice and a great place to end it. Jerry, thanks so much for doing this.

Jerry Colonna (Reboot.ai)  51:21

Thank you for having me on the show. And thank you for responding so well to the book. Can’t wait to hear about the third time you make it through the book.

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