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Episode 51: Interview with Jerry Colonna, Coach and CEO at RebootHQ

As Coach and CEO at RebootHQ, Jerry Colonna talks about just because you feel like shit doesn’t mean you are shit, that there’s a very tight correlation between high achievers and impostor syndrome, and that cringe-worthy moments are great moments of learning.

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CLAIRE: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Team. We make software that helps leaders avoid becoming a bad boss. And on today’s episode of The Heartbeat, I have a guest who I have literally been looking forward to having on this show all year. I have Jerry Colonna, who is an — what’s the right word? Famed, notorious. I don’t know.

JERRY: The Notorious RBG. [Chuckles]

CLAIRE: I think so. Something like that. But as an executive coach. And you run your own executive coaching practice called Reboot. Most recently, you published a book by the same name, Reboot, and it’s on leadership and the art of growing up. And I couldn’t put this book down. There’s so much to get into on this. And then it’s so funny, I have so many folks who’ve actually either been on the podcast, CEOs, and executives, who’ve talked about this book with me or the audiobook. There’s so much to respond to and to get into with you there. But prior to you being a “CEO whisperer”, you were at one point an executive yourself, but has spent most of your career as a venture capitalist. So you founded Flatiron Partners, which for anyone who’s in the tech industry obviously knows Flatiron. And then also you are a partner at JPMorgan’s private equity branch. They’re PE part of JPMorgan Chase. But I’m honored to have you here, Jerry. And to kick things off with this question that I’ve been asking leaders.

JERRY: Before that question, can I just say thank you for having me on?

CLAIRE: You bet.

JERRY: It’s really an honor and I appreciate the work that you’re doing in the world. It’s important.

CLAIRE: Thank you. That means a lot to me. Thank you. All right, drum roll to the question. So you don’t know what the question is, but this is a question that I’ve been asking for the past two and a half years to leaders who I respect. And it’s what’s one thing, or it could be a few things, that you wish you would’ve learned earlier as a leader.

JERRY: It’s a beautiful question and it’s one that I have an answer to right away. And that is that you’re not alone. One of the hardest things about being a leader really stems from the sense of isolation and the fact that — I’m going to badly quote Shakespeare, okay?

CLAIRE: I won’t know the difference. [Chuckles]

JERRY: In one of the histories, Henry V, Prince Hal, who in Henry IV is kind of a ne’er-do-well character who’s just like totally irresponsible. In Henry V, his father dies suddenly and he’s thrust into a leadership position. He’s King and he’s immediately challenged by the Prince, the dauphin of France. And France moves troops into Calais, which is on the other side of the channel. And Henry has to raise an army and go defend English territory. And the night before the battle of Agincourt where it’s very clear that the English soldiers are outnumbered, 10,000 to one, they’re always outnumbered. Henry is walking through the camp and in a soliloquy, he says among other things, “Upon the King! Let us our lives, our debts, our souls lay upon the King! Oh, hard condition, we must bear all.” I think one of the hardest things is the sense that it’s all on our shoulders. And when we believe that we are alone, we wake up at three o’clock in the morning spinning. When we believe we are alone, we believe the stories that our minds tell us. And my infamous somewhat cuss-filled statement comes to mind, which is, “Just because you feel like shit doesn’t mean you are shit.” And if I had only known that I was not the only one, the burden on my shoulders would be a little bit lighter.

CLAIRE: Whew. Jerry, you I think have touched on, I don’t know, maybe the most existential question for us as humans. I know this podcast is all about leadership, but what it honestly brings my mind to, it’s actually I think the biggest thing I’ve actually personally changed my mind on the past few years, five years, which is I used to think that people are inherently islands. I don’t know if you’ve ever seen the movie about a boy. There’s like that opening montage with Hugh Grant and I think he’s quoting someone about every man’s an Island. And through a lot of variety of growing up and being sort of the loner, the odd person out a lot of the times, feeling like you can’t really depend on anyone and my situation is so different than anyone else and no one really gets it. No one really gets me. And then a shift to growing up and realizing actually the thing that makes this fundamentally human is our ability to connect and to have shared experience. And that’s in fact what makes whatever suffering or whatever pain or confusion or uncertainty bearable. And in fact, beautiful is the shared element in that. So, I receive that beyond the scope of just the day to day of running a team and feeling like, “Oh yeah, no, it’s not just when I’m stressed and running Know Your Team as the CEO,” that I know I’m not alone and my team’s here and I’ve got peers and other co-founders, et cetera, who feel the same thing but actually broader in life of we’re all in this, we’re all not alone.

JERRY: Yeah. We’re all in the lifeboats, aren’t we?

CLAIRE: We sure are.

JERRY: Together. I wanted to add that the fact that it triggers existential question, it’s not an accident. The reason the subtitle of the book is Leadership and the Art of Growing Up, the reason is that the process of becoming a better human, the process of becoming a better adult or the adult that we were born to be is hard and painful. And as I often say, it’s why most people choose not to grow because it sucks. And what is beautiful about that relationship between the leadership challenges and the existential feelings that you noted is that we can use those challenges to complete that process. So it doesn’t surprise me, for example, that you said that you’ve changed. If it would be okay, I might suggest an additional word to that verb ‘changed’, the word ‘grow’.


JERRY: So I’ve grown in the last five years and in that growth, I’ve come to realize that community matters. I’m an introvert and I want to honor all the introverts out there because…

CLAIRE: I’m as well. [Laughs]

JERRY: It’s not surprising.

CLAIRE: Exactly.

JERRY: Because I’m imagining now, now I’m projecting onto you. So reject it if it’s wrong, that you enjoy the one-to-one.

CLAIRE: Yes. It’s where I thrive.

JERRY: It’s where we thrive. And so can we be in the lifeboat together where we look across the lifeboat and Jerry says to Claire, “Hey, you okay?” And Claire says, “Yeah, I’m okay. You okay?” “Yeah, I’m okay.” “That was some rough seas.” “Yeah, rough seas. And we’re okay together. Let’s be okay together.” You got me going with your question. [Chuckles]

CLAIRE: I mean, the questions you pose in this book alone got me going. So, it’s symbiotic here. What I was so curious about after hearing your response is having faced that learning or sort of noticed it, observed it, and been like, “Oh, got it,” how do you sort of keep that with you amidst all the changes in seasons and times and the flux of busy conflict, competing priorities. How do you not relapse or sort of recede into that shell amidst how dynamic life is. That’s the thing that I’m always curious about is we learn lessons as leaders. We say things that, or even people tell me things where I’m like, “Oh yeah, totally.” Lead from the front, show empathy, be honest. And the translation into action day in, day out, that always I think, you put a magnifying glass up to it. I don’t know. How closely am I living that out? How closely are others living that out? I’m always very curious as to how lessons can be internalized over time or if there are ways you sort of lock that in for yourself. And then also, you work with so many leaders as well, like helping them. Like when they leave their session with you, Jerry, like how do they sort of keep that with them?

JERRY: I’m going to answer the question, I promise. But first I’m going to go to a different place. The first thing I’m going to note is I can’t help but sort of take this stance. So I’m imagining that that question comes from a hard place yourself. And I’m imagining that Claire, at some point in her life heard something, was moved by it, a bit of wisdom, tried to put it into practice on a daily basis, forgot it.


JERRY: And then the magic moment comes of remembering that you forgot it. Now, at that critical moment, what does the inner voice that is always judging Claire say to Claire? That moment, what does that voice say to you?

CLAIRE: You should have remembered.

JERRY: Okay.

CLAIRE: How did you forget?

JERRY: What is wrong with you?

CLAIRE: [Laughs]

JERRY: You think you’re going to talk about leadership? You can’t even… You hear it?

CLAIRE: Right. Yes.

JERRY: So notice in your body how the feeling is coming up. Okay. I’m going to project a little bit.

CLAIRE: Go for it.

JERRY: Were you a high achiever in school?


JERRY: Always getting the right A’s?

CLAIRE: Always.

JERRY: Always figured out early on how to get the A’s.

CLAIRE: Always.

JERRY: Okay. Because there’s a very tight correlation between high achievers and impostor syndrome.


JERRY: An impostor syndrome is one of the names for it. In the book I talk about the Crow who sits on your shoulder. So if you remember from the chapter on the Crow, one of the very, very important things to acknowledge when that voice comes in. And I hear that voice in the ‘what’s wrong with you, how did you forget this’. One of the important things to remember is that that voice is trying to keep you safe even though it makes you feel like shit.


JERRY: So we blow it a kiss. We say, “Thank you very much. I don’t really need the reminder that I forgot.” And we let that go. So that’s step one. Now I want to respond to the question, the underlying question, which is really about the art of growing up, which is really about the art of transformation. There’s a really important and powerful word I would offer in response. And that is practice. It’s why I call it the art and not the science of growing up. You will gain insight throughout your life. And every single day, you will forget. Every single day, because you’re human. No matter how many A’s you got. And the question to hold on to is, what do we do when we remember that we have forgotten? Do we then pile on and beat ourselves up? Or do we say, “Wow, isn’t that interesting?” And see the thing about transformation, the thing about the art of growing up, the thing about learning and growth is it takes time and repetition. And that’s the practice piece of it. I have a sitting meditation practice. Someday, I won’t need to practice anymore. I’ll be dead. [Chuckles]

CLAIRE: [Laughs]

JERRY: Because the goal is the coming back to. In Buddhism, one of the most important teachings is that, and the future goes something like this: if you spend 20 minutes intending to meditate or you sit down for 20 minutes of intentional meditation and you find that for the first 19 minutes, your mind has been wandering, ruminating, spinning about the future, but wake up in that last minute. Congratulations, you’ve had a very successful meditation session because you woke up.

CLAIRE: Exactly.

JERRY: So the shorter answer to your question is to remember that it’s all a practice and to remember that the practice is coming back to the insight, always focused on the insight all over again and again and again and again.

CLAIRE: I so appreciate that response. First of all, you absolutely nailed why I asked that question. Personally, it’s something I think a lot about because I think congruence for us as humans, it’s the way we sort of conflate it with integrity and when we think about sense of self and trying to form a narrative for ourselves that feels right, that alignment is always extremely important. So I always think a lot about, how well is what I’m saying matching what I’m doing. And then with the leaders that we work with, whether it’s in workshops or I run a lot of in-person training sessions through our software. I do hundreds of interviews like this. It’s a thing that comes up for a lot of other leaders too. It’s like, I know this. If you catch me at a calm, emotional state, centered emotional state, like I know this and then it is forgotten. And what is so amazing about what you shared is almost like what is most salient about that isn’t the fact that you have to put in all this effort to try to remember all the time or internalize it somehow all the time. Because one, that’s impossible. So I just love the acknowledgment like that’s impossible. But two is the fact that the actual value of that process is how you choose to show up when that happens. How do you choose to show up when you forget? Are you hard on yourself? Do you pile on? Or do you take off? Do you get curious about your experience instead of judgmental? And yeah, I love that.

JERRY: Studies have shown again and again that positive reinforcement is the path to true transformational learning, that wrapping the dog on the nose when it pees on the carpet does not teach it to not pee on the carpet.

CLAIRE: Exactly.

JERRY: And so the same thing happens for our own mind and our relationship with our own mind. Wrapping ourselves on the nose is not going to teach us not to forget. Yeah, it’s just going to exacerbate the reason we have forgotten the first place, which is oftentimes a distraction, a reversion to our lesser self, our lesser angels of our nature. Can I bring us back to one of the first points that we spoke about?

CLAIRE: Yes, please.

JERRY: There is an opportunity in that space where the insight that was gained has been forgotten to now remembered that it was forgotten. And that opportunity is to give permission to the community around you to say with love and grace, “Hey Claire, you forgot.” The brilliant poet and inspiration for me, the late John O’Donohue has a wonderful poem called For A Leader. And in it is one of my favorite lines, which is “May you be surrounded by good friends who mirror your blind spots”. And one of the reasons community is so important is to help us remember that we’re not alone. But another reason community is so important, especially in organizations, is to empower our organizations, empower the people around us to say, “Hey, we forgot,” with that kind of whispered love.

CLAIRE: Hmm. I love that, whispered love.

JERRY: I know your heart and I know your intention. And so even when you get crosswise with your own intention, I get to stand shoulder to shoulder with you and say, “Claire, I think you dropped something.” That’s all.

CLAIRE: Yes. As I sort of like dig through my own tendencies of why is it so hard to quiet the Crow. Why is it so hard to have that voice be a whispered love of a voice versus a critical demanding, you should, why didn’t? And you talk about this a bit in your book, which is we as leaders, or maybe I’ll just speak for myself, I know I have a tendency to do this. We so fuse our sense of self with the job. And so poor “performance”, whatever that even means in the job or not doing something that you would see is the right thing to do on the job cuts at the value that we see ourselves as people. And for me, I find that to be — I’m curious about whether it’s your own process of remembering, forgetting and remembering, forgetting and remembering, and then working with all leaders. Do you see that as true or are there other currents that pull stronger do you think? I would just love to dive into that. I think that the conflation of identity and work is just always an interesting one.

JERRY: Yeah. So you’re linking two important concepts and you’re experiencing a cause and effect that’s powerful, and I believe is true. Your first question is why is it so hard to quiet the Crow? And the second observation is that perhaps it’s so hard because the merger of existential identity with the endeavor. And by the way, this is true for everyone in all positions, whether it’s true. William James said, and I’m paraphrasing him, that it is not failure that defeats us or annihilates us, but it’s when we attach our sense of self-worth and meaning to accomplishment of a goal and then fail to achieve the goal that we are annihilated. And so two things I would say. In addition to the merger of sense of self as a reason for the Crow — and so, let me speak about that for a moment. I’m sorry, I’m going to call you out again. One of the things about high achievers is that we very early on begin to get external affirmation of our self-worth. And so we know we did well when mommy or daddy hangs our spelling test on the refrigerator.

CLAIRE: Yeah. Everyone tells us we’re good. Exactly.

JERRY: As a parent, I’ll tell you, it comes from a loving space. It comes from a pride-filled space. But there’s a negative undertone to it that can come across as ‘I’m only lovable if I get the hundred on the spelling test’. And then we live in this comparison world, social media, which is relentless. And so, perhaps this was true for you at 21 or not, but I have some very close personal people in my life who spent some of their years in college saying that they’re going to win a Nobel and that one’s going to get — and this is constant. And so that’s one of the reasons why. It’s that merger of accomplishment. And for entrepreneurial leaders, it’s the merger of the entire entrepreneurial endeavor with self. As a coach, I’m always on alert. My ears prick up when someone says, “It’s my baby.” No, it’s not. Babies are babies. That’s what babies are. Okay, so there’s that. But there’s another more insidious and really confusing reason why it’s hard. And that goes back to one of the first things I said about that voice. That voice is there to keep you safe. It has been there since your earliest days. So when we sit and we start to notice that we have this constant internal dialogue with ourselves constantly [inaudible] as the Crow, the first impulse is to try to beat the crap out of the Crow.

CLAIRE: Get it to shut up.

JERRY: Get it to shut up. Problem is trying to shut off parts of ourselves or there’s a great line which is turning off those parts of ourselves is like trying to get rid of a headache by chopping off your head.

CLAIRE: Oh yeah, that doesn’t work.

JERRY: It doesn’t work. So what you really want to get to is a place where you understand the benefit that [inaudible]. And in your case, for example, that voice did help you achieve. That voice did put you in that seat on the other side of that podcast and microphone, having a dialogue with someone else about issues that are really important to you.


JERRY: So, thanks. But the jujitsu move to make is, “But I don’t need you anymore because I’m an adult and I got this. I’ll take it from here. I love you, but please stand down.” Does that make any sense?

CLAIRE: Oh, absolutely. It’s the difference between listening and obeying. It’s the difference between understanding and internalizing. You can hear it, you can see it. There’s some book I read that made an analogy of thoughts being, you can see the trains going past, you don’t have to get on the trains.

JERRY: That’s a Pema Chodron teaching. That’s who taught it to me. The Buddhist nun, Pema Chodron.

CLAIRE: She’s the best. Her writing is amazing.

JERRY: Teaches to see our thoughts as trains pulling into the station and then we wave goodbye when the train pulls out of the station.

CLAIRE: There we go. It’s definitely Pema Chodron. It’s revelatory. One thing I’m curious to, maybe I’ll hold up a mirror to you, Jerry. How about that, during this conversation? What has been the hardest thing for you or the thing that you actually rather you forget the most and come back to the most and you have the hardest time sort of quieting that crow?

JERRY: There are a lot, and thank you for that question. It’s really helpful for me. But it happened earlier this week as I’ve been describing it lately.

One of the complexities of my childhood resulted in a structure I referred to as “good boy, bad boy.” And there’s oftentimes of a wish to be the good boy, which means that the threat is to be the bad boy. And it was actually just this past weekend, I was doing some solo camping with one friend, but a lot of solo time. And I realized that in Chapter 9 of the book, I open up by recalling myself musing on the question of am I a good man? Have I been a good father? Have I been a good partner? Am I a good CEO? Am I a good man? Because I identify as male. And I realized this weekend that that is just a grownup version of that early setup, which is to wonder if I am worthy of love because, in order to be worthy of love, safety, and belonging, I must be good.

CLAIRE: You must be good. Right. It’s not inherent.

JERRY: It’s not inherent. Right. Well, that’s the belief system.

CLAIRE: That’s the belief system, exactly. That’s the mental model.

JERRY: That’s the mental model.

CLAIRE: It’s wrong.

JERRY: It’s completely contrary to the teachings of the Buddha. So you asked, what is it that I forget that I need to remember all the time?


JERRY: It’s that I can live beyond the good boy, bad boy set up. Lately, I’ve been thinking a lot about the next book, and that may be part of what I’m playing with is the notion of what exists beyond that construct.

CLAIRE: Yes. To me it recalls, and you know, we have a tendency to do this when we’re interviewing people. We immediately or I immediately think, “What do I see myself in hearing that,” which goes back to something you mentioned about the seeking for approval. Like anytime we try to assert value or define how good am I that or am I being valued, it’s a subconscious seeking for approval. And so I think I try to ask myself, and I’m curious if you do a version of this for yourself or for your clients is they ask, “Who am I trying to impress right now? Let’s get real.”

JERRY: I’ll give you something that I was taught by one of my coaching instructors early on and it produced a lot of shame. It’s what I refer to as a cringe-worthy moment. The cringe-worthy moments are great moments of learning. And it was very, very early on in my coaching career. And as part of the coach certification process, I had to record sessions with the client’s permission and then play them back with a senior coach, with a master coach and talk about what was going on. And a lot of times Martha, this coach Martha Lasley would say, “Okay, what’s going on right there? What are you doing right there?” And she gave me a tool which I used for a long time and probably should get back to it, which was she made me write on a sticky note the acronym W-A-I-T. And what it stands for is Why Am I Talking?


CLAIRE: I think I need that everywhere in my little home office here. My goodness.

JERRY: One of the many things I love about that is there’s a sharp, effective, loving humor in it, which is the best way I learned. Oh yeah, I should ask a question and shut up, as a leader and as a coach.

CLAIRE: Absolutely. It’s so funny. We were in workshops and trainings and receiving feedback well. And one of the hardest pieces of the framework that we offer is talking less. It’s so hard. It’s so hard. We feel like we have so much to say and to justify and to work through and to process. And it is so, so hard. On the topic of questions though, Jerry, I was very intrigued to know what’s been the hardest question that you’ve had to ask yourself? Or what is a question that you always come back to sort of as a self-check?

JERRY: The question that really began changing my life was how have I been complicit in creating the conditions I say I don’t want,

CLAIRE: I heard you share that, I think, on Tim Ferriss’s podcast.

JERRY: Yeah. When my psychoanalyst started teaching me the underlying belief systems behind that and the structures, it was like I took the blue pill and saw the matrix. Holy fucking shit, I’ve created this whole world.

CLAIRE: What did you see, yeah.

JERRY: The truth is every single day, I forget that the stories I’m telling myself are in fact stories. But when I remember, it’s usually after I’ve had an opportunity to be able to turn around and go, “Okay, what’s my part in this?” Not, “Why does this always happen to me?”

CLAIRE: Or why can’t I figure it out? Why am I messing this up so bad?

JERRY: You hear that Crow? It’s relentless.

CLAIRE: The choice of word for complicit in that question, how am I complicit in the conditions that I may or may not want to have? Tell me about why that word, in particular, is so helpful in asking this question. Why not, how have I not caused this, or what am I doing to cause this, or what am I doing to contribute to this? There’s a lot of words you could use instead.

JERRY: Yeah. Thank you for asking for that clarity. I like the word complicit because we’re accomplices in our lives. We are not the sole actor. See, part of what the Crow does is it either denies our agency or attribute all problems to us. And the truth is neither of those.

CLAIRE: Exactly.

JERRY: We have agency and we’re not 100% responsible, but we live in a very childlike black and white world where either we’re entirely the victim or entirely the perpetrator. Neither is true. So complicitness means I am going along with the act. I am the driver of the getaway car in the bank robbery. I’m not walking in with the gun. So I’m an accomplice. That’s important because when we start doing that inquiry process, one of the first things the Crow will do to protect itself is to start telling ourselves what a jerk we are for having belief systems in the first place. And so that’s why that word complicit is really important because it sort of breaks the bond of that. Now the second half of that, the words are important. The way I frame it is I say I don’t want these conditions. What I’m trying to do there with that part of the question is to make a distinction between what I say out into the world at large and what’s really going on inside of me.

CLAIRE: What you actually want.

JERRY: I say I don’t want to be so busy, but boy, does it feel good to feel like so responsible for everything.

CLAIRE: Yeah. Important. Valued, needed.

JERRY: Valued, especially if I get my value from external circumstances, my calendar is going to be filled. And so by making the distinction, I hope to encourage an acknowledgment that we are often subject to multiple different motivations and intentions because we’re complex human beings. And so that’s why those words are so important.

CLAIRE: Thank you so much for sharing that. That is such a powerful, powerful question. It’s one I know that I’ll be walking away asking myself. I also was thinking, this is a little bit sort of related but maybe shifting gears a bit, is I’ve always found it really interesting and you know, studying leadership now for almost the past 10 years and there are so many different frameworks and models that people use. And then you also sort of can look at more, I guess, how would you describe it? Whether it’s religion or other sort of more formal philosophies around life. And I always found it very interesting that some of the most popular takes on how you best lead is about the reduction of ego and sense of self. And to be a good leader, you need to be thinking about everybody but yourself. You need to be in service of something. Buddhism particularly is all about reduction and separation of yourself from that sense of self. And what I find so interesting about that is that it directly conflicts a lot of times what seems like the reality of the way we’re supposed to do our jobs as leaders.

JERRY: How so?

CLAIRE: Which is that we have to have answers that people look to us for direction, that even our sense of self in some ways defines a company or a brand or even sets what value should be for a team just by what we personally value. And so, I’ve always been curious about that tension of sort of the philosophical notion of separating sense of self or making sense of self smaller. And then just also this noticing of like how many problems emerge from tying sense of self so tightly to the role that you do. I just wanted to riff on it with you and sort of pick it apart. Do you see a similar tension in the day-to-day of the things that are required of us as leaders sort of demanding that we show up as very cemented in our sense of selves and putting that forward? Do you even believe that sort of separation of that sense of self or reducing ego is sort of the path to go to, to become a better leader, a better person, human? I wanting to just poke on that concept with you.

JERRY: Here again, I promise to come back with a direct answer, but I can’t help myself.

CLAIRE: I love it.

JERRY: I’m going to reflect two words that I heard or two phrases. Required of us. Demanded of us. Who’s doing the demanding and who’s doing the requiring? Who requires that you have all the answers? I’m asking directly.

CLAIRE: Probably myself. Yeah.

JERRY: Okay. So let’s just pause here for a moment. The basic premise of your question is the observation that there is a mental model around leadership, which is that a leader is the one who has all the answers. And immediately in relating that observation, you externalized it. Other people expect this of me.

CLAIRE: Right. I love that observation.

JERRY: And then when I poked at it, you immediately went to, “Oh, actually, it’s internalized.” Now, it’s an internalized belief system that you weren’t born with it, you learned it. So, there is a belief system in our society that the one with all the answers gets all the toys. The one with all the answers gets the A in class. High achiever again. Here we go! Now, you’re linking that in your question to this question of diminution of ego. There is no getting rid of ego. None. Even his holiness, Dalai Lama has an ego.

CLAIRE: I mean, it’s the way we make sense of the world, right?

JERRY: His relationship to the ego is different than yours or mine. But he has an ego. He happens to have a very funny and humorous relationship with his ego. He can laugh at his ego, but there’s no getting rid of the ego or the self or any of that. That’s a charlatan’s game that doesn’t exist. When we pursue that and we fail, we give energy to the Crow. It tells us what a jerk we are. So let’s put that to the side for a moment. Now, when a leader of an organization takes the position that they’re supposed to have all of the answers, they are inadvertently using the organization to assuage their internal inner critic. And there is nothing that someone who has positional or role power, there’s no worst damage that a person of positional power can do than to inadvertently unconsciously use the organization to deal with their own demons.

CLAIRE: Exactly.

JERRY: And so we have to question that first assumption, which is that the person who has all of the power needs to have all the answers. Now, let’s just get really pragmatic about that. I can’t see a faster obstacle or a deeper obstacle to scaling an organization than that belief system.

CLAIRE: I would agree.

JERRY: What Peter Drucker says is that the leader is best who asks questions. Warren Bennis says a leader’s job is to ask questions. Open honest questions, not setups. “Well, have you given thought to doing X, Y, and Z?” That’s not an open, honest question.

CLAIRE: No, leading. Yes. Directive.

JERRY: Leading.

CLAIRE: Yes, it’s a directive question.

JERRY: That’s right. So, the real work is to go at the internalized belief system and realize that my job as a leader is to encourage the development of people who can answer my questions. And my job is to actually ask curious, open, honest questions from places that people may not have even seen because I’m using my open holistic perspective to try to see things that others may not be seeing.

CLAIRE: Absolutely. In many ways, it’s why — to tie back to what we touched on earlier, Jerry — is why that word complicit I think is so important is because pretty much everything we’ve identified as external problems or situations we need to figure out. It is, as you mentioned, an externalization of something internally we’re trying to figure out for ourselves. And so the complicit is unknowing. It’s unintentional, but it’s contributing without even realizing that it’s there. And I know that this is what your entire coaching philosophy is based on. So the book talks about this radical self inquiry is the only way we get past that. If everything that we see as problems is an externalization of the things that are going on inside, then how do we ask the right questions to figure out what’s going on.

JERRY: And the tool we use is to always ask ourselves those questions. And here again, we will forget this a thousand times a day and then we come back to it.

CLAIRE: Practice.

JERRY: Practice.

CLAIRE: Jerry, I can’t tell you how informative even this short 40-some minutes has been in helping me practice that the process of forgetting is, in fact, the process. That’s the work, and it’s the reward is to go through that. Someone had told me recently about how they had learned that, when I am away from my company and I’m focusing on myself and maybe seeing an executive coach or working out or going on my runs or going to yoga, doing things that invest in myself, I used to think that’s about, “Oh, okay. Getting time away from the business, getting time away from all the things,” so that I can show up and then be super on, on my day-to-day. And he realized he was talking to I think a mentor of his and he’s like, “No, Claire. It’s actually completely flipped. So the time that I am actually giving back to my team, giving back to my organization, my company, it’s when I’m actually by myself. It’s when I’m focused on myself and asking those hard questions and taking a rest and the time and the breaks to recalibrate and reflect. And the times that I’m receiving, the times I’m actually feeling and getting something is actually when I’m with my team, that’s what I’m receiving. I’m giving when I’m by myself and I’m receiving when I’m with my team, instead of the other way around.”

JERRY: I like that structure.

CLAIRE: Yeah. And that was a really powerful reframe for me in thinking about how whatever problems I’m facing to your point, they are versions of things I’m trying to figure out for myself. And that the ways that I actually can give and show up is when I’ve let this go and show up with more space. So, thank you.

JERRY: You’re welcome. And in closing, I would just encourage that, reiterate something I said before, which is that those of us who are privileged to have power have a moral and ethical responsibility to be vigilant about the ways in which our nonsense hurts other people. And the more power you have, the more responsibility you have as Peter Parker’s/Spiderman’s uncle said, “With great power comes great responsibility.”

CLAIRE: I was just about to say there’s a reason Stan Lee sort of immortalized that it’s because it’s true. It’s true. But here’s what I find refreshing though about this Jerry, which is that we have the answers then.

JERRY: Amen.

CLAIRE: They’re all here, right in here somewhere. Like it’s not some unsolvable [inaudible] thing that we have to go out and go on some long track to figure out. It’s some commitment to wanting to figure out what those answers are, it’s asking the right questions, being vigilant about asking them, then doing the work and practicing.

JERRY: It’s doing the work. It’s doing the work. There’s a line I use in the book, which comes from one of the folks who came to one of our leadership retreats said, which is, “You mean there’s no playbook?” I was like, “Nope.” I mean, there are plenty of people who write playbooks.

CLAIRE: Oh, yeah.

JERRY: But really…

CLAIRE: I don’t think that’s how life works.

JERRY: Yes. Amen.

CLAIRE: That’s not how life works. Thank you for helping me, for helping so many others who are listening to this podcast feel like, “All right, we are not alone in this whole thing called life.”

JERRY: You got it. It was a pleasure to be on and thank you for such thought provoking and fun questions.

CLAIRE: You bet.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.