#55, Jerry Colonna, Author and Executive Coach — the distinction between vulnerability and hone...

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome back to From Startup to Grownup, and today I'm thrilled to have Jerry Colonna on the podcast. Jerry is an executive coach, a former venture capitalist, and the author of two books, most recently Reunion: Leadership and the Longing to Belong. Jerry and I both like real talk, so we had a fantastic conversation starting with the idea of radical self-inquiry and why doing radical self-inquiry is so essential for you if you wanna grow. We also cover one of my favorite topics, the importance of giving people positive feedback, not just negative feedback., as well as tools to make sure you're doing that. We cover the distinction between honesty and vulnerability and why you should not seek to appear infallible as a CEO. We also talk about Jerry's upbringing, his own imposter syndrome and how he handles that, and some of the core principles of his new book, Reunion, including the idea of the interrelatedness of all of us and our stories. Very interesting discussion. You're gonna love this conversation and gain some great insights and practical tools So please enjoy my conversation with Jerry Colonna. Jerry, welcome to the show. I'm so excited to have you.

Oh, thanks for having me. It's a delight to see you again. It's a delight to be here with you.

Good. I feel the same way. I'm so excited to catch up with you. I really wanted to start with what I think— you're known for many things. You're an iconic executive coach and you're known for many things. But one thing you're really known for is this sort of operating system of radical self-inquiry. So I'd love to start there and hear maybe you riff on and just talk a little bit about what is radical self-inquiry and why is it so important?

Well, first of all, thank you. I don't know that I can accept being called iconic, but I'll take it as the compliment. Yeah. Okay. So the standard definition that I use is that it is the process by which our— the masks that we hide, behind which we hide, are slowly and compassionately stripped away to the point that there's no place left for us to hide. Now, how does this show up in coaching? And so let's unpack it a little bit. I call it radical because we typically tend not to do this work. We typically don't ask the kinds of questions that would be unlock questions. So a very famous question that, that has made its way in and around the internet is, how have I been complicit— not responsible, complicit— in creating the conditions I say I don't want? The reason I cite that is that it's the kind of question that could, if not really approached correctly could induce shame and guilt and kind of a cowering and a withdrawing, when in fact it's— the purpose is to elicit curiosity and to acknowledge, uh, for example, that while we may not be responsible for creating the conditions in our life, we may in fact work for a really bad person, we may work for a toxic boss, What is curious is why did we take the job in the first place? Or more specifically, if we found ourselves repeating a pattern, what is the benefit of that pattern? And the reason that that's so important is that I believe that transformation occurs not merely through the unlocking of cognitive awareness, but really understanding the underlying need that the behavior is seeking to meet, even if the need is a negative need. I have a need to see myself as valuable. So, I will substitute busy for valuable. And the result is I spend my days frantically moving from thing to thing. Rather than pausing and asking myself, what would I really like? How would I really like to spend my time? So that's a long-winded response to the question about radical self-inquiry. Um, again, it's, you know, it goes by many other terms. I just happen to coin that term, and I find it useful to refer to it that way.

Well, I think it's useful, and I also think it's, in a good way, provocative. So it, you know, it's sort of, it's interesting, it ignites something. And, you know, when you were saying all that, I was to myself, there's an adage I always love, you take yourself wherever you go. And so if you keep taking yourself wherever you go, you're going to keep ending up in the same places.

Right.

Unless you're able to mine that baggage or, you know, as you say, sort of strip away that mask. But then you also said, and I think this is so powerful, you have to do it in the right way. So because anyone listening to this podcast, any leaders that we deal with would be like, 'Hey, how are you complicit, you doppo?' You know? So can you talk more about the attitude with which it's so important to approach radical self-inquiry? And then also, if you could give a tangible example, I think it'd be so helpful for people.

Yeah, I— look, I, I think that, um, and, and for— by way of an example, I'll always go to the— I'll go first, right? I will do this to myself all the time. And the busyness is a perfect example of that. The, the, the— let's take a step back and think about the attitude. The attitude should really be about curiosity. And the reason that that's so important is because when we turn to guilt, when we turn to blame, we activate shame, we activate the defense mechanisms, if you will, of self-denigration. And there's a little bit of a learned belief system, which is that if I yell at myself enough times, I'll finally eat healthily. Well, it just actually doesn't work that way. Right? What works is positive reinforcement. But too often as children, we're socialized against positive reinforcement. We're more afraid of disappointing our parents than we are enjoying their pride. And so in a similar way, what we try to do is use this internal inquiry process. To really unlock with loving kindness, why do I do what I do? Or another way to ask that question is, what need am I trying to meet? What is the benefit of the behavior that I'm seeking to change? What is the benefit that that behavior has met for me? And I'll give you a good example of that. A few weeks ago, I was with a group of CEOs, portfolio offsite or summit for a venture firm that I'm pretty close to. And we were talking about ways to be with their employees. And one CEO, a woman, raised her hand and said, relevant to the exercise I had just taken them through, "So what you're saying is we're supposed to go for walks with our employees?" And I said, "Well, yeah," you know, 'cause I'm a big fan of going for walks.

People.

So she sort of rolled her eyes and she said something like, well, that's not going to solve my problem. My problem is none of them can make any decisions without me. It's like, okay, so how many employees? 15. It's like, okay, and so they're really not capable of making any choices themselves? She goes, yeah, it's just terrible. So I paused and I said, well, who hired them? Yeah. And she smiled and just like, oh, well, I was like, okay. So I said, so a consequence of the hires you have made is that you're at the center of this whole complex and you feel trapped by it and you're exhausted and they don't understand you. She said, exactly. And you don't want to go for a walk with them. You don't want to understand what's going on with them. Correct. I said, okay, so let's try something new. What's the benefit to you to them not being able to make any decisions without you? And a devilish little grin came across her and she said, I get to be in charge of every decision. I said, okay, now we know what's really going on here, right? And that's just a tiny little example of what we're talking about here is like when we as individuals see a situation that we don't like, and as leaders, we often see situations we don't like. What radical self-inquiry does is it encourages us to turn the lens inward and say, really, how has this served me? And is the benefit to this— does it outweigh the cost? 'Cause almost invariably it does. And then you're in a position where, as I often say, the adult version of your brain gets to make a choice instead of the childlike version of your brain saying, if I allow people to make decisions without me, then what's going to happen to me? Will they no longer need me? That's a childlike response in a leadership situation.

Right. Very powerful. And I appreciate that example. And you sort of dig deep. By the way, sometimes people in my experience will explain to you why it's not in there. They're not getting any benefit out of it. In fact, it's angering them. So it's a few rounds of like going through that process until they sort of see what you just talked about. And then I appreciate that what you're saying is, and then the adult, the inner self, the adult of the inner self can come in. And I guess I'm curious, what do you see? How do people change from there? Because that insight is very, very powerful. But then, you know, after the ecstasy, the laundry, right? They go to the offsite, they go back to their place, and it happens again and again.

How—

what is the process of actual both behavioral change but also identity change on the inside?

Well, I don't know if it's so much identity change, but it's certainly transformation of the behavior that I think we'd be seeking. Look, what you're noting is the insufficiency of cognitive awareness. Cognitive awareness is incredibly important, but it's insufficient to creating change. James Baldwin said, not everything that can be faced can be changed, but nothing can be changed until it's faced. And we're in that kind of a zone where the— it's a vital step is to actually unpack and see how we contributed to creating the conditions that we're so desperately wanting to change. But it takes repetition. It takes time. It takes compassion to self. Um, here again, you know, we were talking before about like people being socialized to think that negative self-thought is the key to change. Um, whether I'm trying to, to work with employees around me and I speak to them negatively, or I'm trying to change myself and I speak to myself negatively, The evidence is pretty clear that, that what creates the change is positive affirmation, right? We reward the dog for not peeing on the carpet more than we hit them on the nose with a rolled-up newspaper, right? Because all we're doing in the latter is teaching them to be afraid. And, and fear as a motivation is not sustaining, right? It's not generative. It doesn't create new ideas. It doesn't create new opportunity. And so just understanding at that moment doesn't really create the change. But creating hyper-awareness of, oh, there I am, I'm doing that thing again. I don't want to do that thing anymore. That's a necessary step in the process of transformation, right?

I love that. And also your ability to be a witness of yourself and to catch yourself in that moment of like, oh, I'm doing that again. And then another, I know, big sort of theme for you is curiosity. Like, oh, I see myself doing that again, right? That's interesting.

I wonder what's right. I think you just, you formulated it correctly. There was a kind of gentleness that you just used that with, which is approaching oneself with loving kindness, letting go of expectations of perfection, letting go of expectations of getting it all right, and understanding that this is all a practice, that this is an art form, and that as we age, we theoretically become more and more comfortable with the experience of being alive. That's, I think, what our goal is, both as leaders and as adults.

Right. Certainly the experience of being alive and also self-acceptance. Right. The idea, I think, that I think these are sometimes a paradox, the idea that you can and should work to accept yourself, and in there is the key to change.

Yeah. And again, we start going into motivation. More evidence shows that intrinsic motivation creates more positive change within us. And so if I am accepting of myself, but I remain curious and enlivened by my own growth, then I am intrinsically motivated to continue growing. I get self-satisfaction out of learning new things. I'm reading a book now on mass incarceration for no other reason than I'm really curious and I really want to understand. Where we are. And that makes me feel alive, feeding that intellectual curiosity. And so I move forward through life like a shark moving through water. It feels like it's breathing. It just feels like it's the thing that I do.

Yeah. And it's dynamic in that sense.

Yeah.

You know, so I appreciate this discussion and how important those aspects are for dealing with yourself, right? So self-acceptance and compassion and then dealing with other people. And I would just say another theme that comes up in your work is the idea of vulnerability and your ability to be vulnerable with your team. But if I go back to the CEO that you were dealing with a few weeks ago, if she's rolling her eyes about, taking walks with her employees, she and many CEOs are rolling their eyes about vulnerability. So I'm curious, how do you sort of talk about, or how can you guide people or coach people to be vulnerable appropriately? And then of course, the other side of that is maybe overspilling and oversharing and having it be— having people lose confidence in you. So how do you sort of think about the topic of vulnerability?

So I think those are actually 3 different things, and I'll speak to each one of them differently. The losing confidence, the phenomena of oversharing, and vulnerability generally. First of all, I typically don't speak about vulnerability. I know that that might surprise you. And the reason is that the word vulnerability has negative connotations. It implies, even though it doesn't connote this from a definitional perspective, but it implies a weakness. And I'm too old to be pushing up against that problem.

You're like, you're giving that up, you're surrendering to that.

The word that I prefer is a little more radical and it's a little more startling. Which is honest. And as soon as— see, it just happened to you. The minute I say that word, people sort of take a step back. It's like, oh wait, he's right. Yeah, yeah, right. And so let's talk about the association between the two for a moment. The, the, the— we have been socialized to believe that if we are honest then we will be vulnerable to criticism or vulnerable, in your case, as you were saying, to people losing confidence in us. You hear how I draw it out?

Yep.

So I'm going to say it again. We have been socialized to believe that in order to lead well, we need to be dishonest. Now, do you see how the logic falls apart as soon as I say this?

Yeah.

So that's why I don't focus the conversation on vulnerability. I focus the conversation on honesty. So if we go back to the example I gave you before, the CEO, if she has a choice at this point, She can continue to roll up a newspaper and whack people on the nose and expect them to behave differently. Good luck with that. Because the minute they get another job offer, they're going to be gone. But if she says to the team, hey, listen, because I'm afraid, I tend to be controlling. And because I'm controlling, I have often disempowered you from making decisions. And worse, because I disempower you, I feel overwhelmed because I feel like I'm the only one who's making decisions. The risk is that people will lose confidence in her because of that. But I think that the people who are really self-confident will appreciate that honesty, will roll up their sleeves, will stand shoulder to shoulder with her and say, Okay, yeah, I got my own bag of shit. I do similar things. So let's just work together and we'll figure it out. See, part and parcel of this kind of approach is to take the leader or CEO out of this primacy position of having to have infallibility and perfection. And all the answers and realizing that what their, their job really is, is to create an amazing team of people so that the burden is shared. Now, that's the answer to vulnerability and folks losing confidence. I'll say this about oversharing. In all the years that I have been doing this, The fear that I am going to be accused of oversharing is maybe the most pernicious fear. When I hear someone say to me that they fear oversharing, what I begin to get curious about is when did they first begin to hear the message that their feelings should not be shared. Now, there are people who are so narcissistic that can only stay in a structure of talking about their experience. That is true, but I don't think it's the vast majority of us. I think that the fear of oversharing is an overused tool because a few people are really narcissistic and emotionally manipulative, whereas the vast majority of us are just trying to do our best. So that was a long-winded response to a 3-part question.

Well, I appreciated it. I'm sort of processing what you're saying. I guess I just want to ask you a little bit more about where you said, you said, um, you know, if you're being honest with people and you go through the, here's, here's why I do it. And, you know, here's what I've kind of understood. And like, like you were talking with the CEO, right? So I tend to be over-controlling and then I don't let you make decisions and then I get overwhelmed about it. And so kind of, there you go. By the way, I also really think it's powerful inside of a team to just own up to it, right? We'll, It's so important for you to create the conditions where people can just own up to their baggage, own up to their stuff. And yet you said, I think confident people will relate well to that. I think self-aware people will relate well to that.

Sure.

As in, like, I have my own baggage, whatever. But I am not sure that a lot of people are self-aware. We don't teach a lot of self-awareness skills as people grow up. Do you observe that most people are self-aware? Uh, yes.

I mean, I, I, I'm, I'm trying to figure out how to get the words out as quickly as possible. I completely and totally agree with you that we tend not to teach our children, uh, the self-inquiry, self-awareness skills. We struggle, for example, to even give children the words to name their feelings, which are among the most powerful energetic states, is that is when we're overwhelmed with feelings. And instead, we tend to fix or shut down those experiences. So instead of naming the feeling. Oh, I see that you're sad. Can you tell me about why you're sad? We say whatever we need to say to make the crying stop. And we do that, I think, oftentimes because we ourselves don't know what to do with that person's feelings. We don't know what to do with the helplessness that this other person's feelings may induce in me. And so we either fix it away or we shut it down, right?

It is true. That is the state of the world.

And then we give those adults power, and then we wonder why we have toxic situations.

Yeah, exactly. And then we set every one of them loose in the workplace.

That's right.

Bedlam ensues.

Or our political communities, right?

Right.

Yeah, right.

For sure. For sure. So I'm curious if you like, you know, we have a whole bunch of founders, of leaders, of coaches listening to this right now. Could you just riff on a few ideas? If people are like, you know what, I need to improve my own self-awareness. I understand that. I want to improve my self-awareness. Listen, I could see how beginning my own inquiry would be really helpful. And they don't have access to you or to me or any other coach. What kinds of suggestions do you have for people to do that independently?

Well, you know, there's one thing that I do in a lot of public talks. I will often make reference to an article Wired magazine did about me years ago. The headline of which was, "This man makes founders cry." And then, you know, everybody's like, "Oh, okay, what does that mean?" And then I say, "You know, you want to know the secret to making people cry?" And I turn around and I look them dead in the eye and I say, "How are you? No, really, how are you?" Like, don't fuck around. And the reason that that unlocks feelings, whether it's tears or anger or overwhelm or joy, the reason it unlocks those things is because we often don't even ask that question of ourselves. So when I journal, as I do every morning, the first question that I ask myself is, how am I feeling? The first task that I do is I take an inventory. It might be physical, it might be emotional, it might be the things that were triggering for me yesterday. Now, why do I do that? It's, it's, it's literally about getting a fix on my life. Where am I? Imagine you're setting forth in the woods and you've got a compass and you've got a map and you find yourself suddenly feeling like you're lost. Well, if you haven't started the trip by knowing, by looking at the map and knowing where you began and where you're intending to go, you will be lost. And so that's— that, that capacity to check in with oneself is absolutely essential. Now let me ask you a question.

Okay.

What stands in the way of people knowing how they are doing?

Well, I think what stands in the way is, um, out of habit of touching into it. That's one thing, like lack of habit of touching into it, lack of practice therefore in feeling, identifying it, lack of even asking the question, lack of, you know, increased busyness. And so you don't ask the question. I think all those things get in the way.

The benefit to a person of not asking that question How are they complicit in the conditions?

Sure. Well, you don't want to— you don't want to feel it. You don't want to know how you are.

Right. And you may have even grown up in an environment where, because we don't know what to do with the feelings, we actually don't talk about feelings.

Yeah.

So we sweep them all under the rug. Right. We don't talk about it. We don't talk about the fact that Mom is depressed or we don't talk about the fact that Dad is an alcoholic, or we don't talk about the fact that, you know, our family lineage comes from a place that suffered through pogroms. We don't talk about any of these things. We don't talk about, you know, the uncle who lost a fortune and then therefore killed himself. It just sort of bubbles beneath the surface again and again and again. And because we don't talk about it in a family structure, then we have power. We're in a CEO position. We hire a coach and the coach says, well, I can help you, but can you tell me how you're feeling? It's like, I don't even know how to answer that question. Well, your employees are asking for empathy. Can you ask them how they're feeling? I don't even know how to answer that question.

Right.

So, yeah, you know, you're right, I was pulling a radical self-inquiry, uh, process here. There is— it's really critically important. You asked, how do we develop and cultivate that self-awareness? One of the really crucial questions to ask is, how has it benefited you to not go there? Yeah, more often than not, it's a feeling of safety. Yeah, because if I go there, I don't know what's going to happen. And if I don't know what's going to happen, all hell is going to break loose, and I'm barely holding it together right now.

Yeah, I think that's so true. And you were just sort of talking about childhood and all the different secrets that we don't talk about in childhood that are going on in the house. And I think, to me, all roads— all secrets— all roads lead to shame. Yes. And the touch, you know, the shame is the un— is there are other uncomfortable things, but shame is so uncomfortable. So you want to cover that up and mask it.

That's right. That's right. That's why vulnerability is so frightening. Right. It's actually the shame that lies behind it. That's why I try to turn that on its head and say, oh, we're being less than forthright. Because we're trying to protect something. And then the question, the really unlocked question, is, does it need protecting anymore?

Yeah.

Or is the habit so ingrained that we don't know how to do anything but keep that secret?

Right, right. It's right. I think that— and then habits, that's the whole thing. It's like you do this thing, you're not even aware of it, and then it just becomes a habit. And then when no one's asking— so to your point about asking, "How are you? No, really, how are you?" to somebody or to yourself, actually, that breaks the habit because nobody's asking that question.

That's right.

I was just like, "How you doing?" It's not important.

That's exactly right. Or at least we're sending the signal that we don't care, right? When in fact, you know, we're all terribly lonely on the other side, on either side of that encounter. Right? How are you? How are you? I don't really care. I don't really care. I'm too wrapped up in my own shame. I can't see you. And it hurts on those sides.

Yeah, yeah, for sure. And so I think I'd love to ask you at this point also about another topic that you've talked about that I think is, is linked to all this, which is the shadow, the shadow side of individuals. What is the shadow and How does that show up inside of leaders, inside of people?

So the term comes from Carl Jung, who described the part of our psyche in which we put the unacceptable parts of ourselves. And the unacceptable can be— it's often associated with negative parts of ourselves, but it could be the positive parts of ourselves. What do I mean? So, we might be naturally strong leader. We might kind of see clearly what people need, but because we were socialized as children that speaking up might have been a demonstration of our ego, we might toss that positive quality into the shadow and then try to get the leadership material to operate by working around and through other people. So positive intent resulting in emotionally manipulative behavior. That's when the stuff that's in our shadow starts to call the shots. And we start operating in a less than fully authentic and fully honest way. And there are a million examples of that, but I'll just stop with that.

Well, can you give one sort of specific example and follow that through? I think it'd be really helpful.

Aside from what I was just saying about the positive.

So, right. And also just like follow through how that changes.

Right. So there's another thing might be that I might have a negative and outsized negative reaction to a colleague. I cannot stand that person. Every single time they open their mouth. And what's really going on is that their loquaciousness or their eloquence or their ability to speak up and be heard is something I envy, something that I wish I had inside of me. And it's so unbearable. This state of mind is so unbearable that I start to act out of the shadow, and I start to undercut that person, or I start to talk behind their back, or I start to gossip about them. And what's really going on is that the root of it is disowned parts of myself. I'll give you another example. In Reboot, my first book, I talk about a client who came to one of our boot camps and was complaining constantly about what he called is his pain-in-the-ass SOB head of sales who was so greedy and he just drove everybody crazy. And finally, one day we were talking about— on day 3, we were talking about this very topic. And I asked him to talk about the greed. And I asked him a set of questions. That what unlocked in him was an experience he had where he was desperately poor. He was a teenager. He had run away from home. He had an abusive childhood, and he found himself hungry and cold and addicted to alcohol underneath an overpass in the South, in Atlanta. And what I had helped him see was that— because I had asked him the question, well, who hired this SOB, right? And what I helped him see was that he had— his unconscious had found an ideal person to live out that part of himself that was unacceptable, the greedy part of himself. And in taking it back, what we did was we transformed it from a negative— greed— to a wish that everybody in the organization would have enough food, and that the purpose of the company was in fact to create prosperity for everybody. And that was a way to sort of take back that which had been tossed into the shadow— his greed manifesting in this really toxic situation. So that it then can be transformed into a positive. And the positive being, let's lift all the boats, let's raise the tide, let's have a good— let's have a great experience.

Right.

That's a good example.

I love that example. And you said transformed, and I would also just say it feels to me like also integrated, that you can integrate that shadow self, shadow side.

Sure.

Yeah, that's beautiful. You know, Jerry, I really have always appreciated that you've been so honest, vulnerable, honest about your own journey. And you know, when you mention— and you mentioned your first book, Reboot— and in— after your book Reboot came out, you had a lot of people coming up to you saying, or writing to you, your story is my story.

Yeah.

Could you share a particularly meaningful example of that?

Yeah, well, in, in Reunion, the new book, I tell the story of one woman in particular. And there— and, and, and to this day, listen, people still come up to me and tell me after reading Reboot how moving it is and, and, and how the connection is. But I tell the story of this one woman, Joy Tendei. I was in I was doing a book reading for Reboot in Dublin, and it was a room full of, not surprisingly, white people. Most of them had blonde hair and blue eyes, and except for one woman, and that one was Joy Tanday. Joy is a Black woman, and she sat in the very front row, and she was very studious, taking a lot of notes as I was speaking and reading from the book. And at the very end of the talk, she came up to me and I was— you know, you've got— you've done public talks, you're a little bit like exhausted and your eyes glaze over and you're like talked out, but you're being kind and you're listening and you're connecting and you're appreciative of people coming and all that. Anyway, I was in that state and she starts telling me that, um, that there was one thing that I had talked about, um, that she really resonated with, and this notion of early parentification, of being, um, forced into adulthood at an early age. And I was sort of nodding along, and she said, yeah, yeah, my father died when I was 13. And again, sad, but story I've heard before. And then she pauses and says, on Robben Island. And that sort of blew me away. And I looked at her and I said, "Where Nelson Mandela was held?" And she said, "Yes." And it turned out that her father, based in Zimbabwe, had been a freedom fighter fighting against apartheid in South Africa, and that he had been captured by the South African police and beaten to death when she was a teenager. So not your everyday story. And at that point, she then goes on to talk about emigrating to Ireland, and she's an Irish citizen now, and she's raising her children in Ireland and all. She, she then says to me about the stories I told in Reboot, 'Your story is my story.' And that shocked me because I'm just a kid from Brooklyn. I'm about as far from Robben Island as you can imagine. And this notion that we can find connection in each other's stories, I find incredibly moving. You know, I wrote about this as well, you know, in the same few-day period last year, I received notes from Two men, one on death row and one the CEO of a Fortune 100 company, both of whom said in some form or another, "Your story is my story." And if that is true, and I believe them, then their stories are each other's stories because that's how the transitive nature of properties works, right? If A equals B and B equals C, then A equals C. And one of the troubling aspects, one of the reasons why I even wrote Reunion in the first place, one of the troubling aspects of our experience, and partially because of the way we're socialized, is we don't know, we don't see the empathetic connection that actually exists between all of us. See, we're so busy disconnected from not being able to answer the question, how am I, that it's almost impossible for, for me to say, well, how are you, and to hear it and take it in. And I think that that is a very troubling truth of our society.

Yeah, the lack of that ability. Absolutely. There's a lot to process in what you just said. I mean, as you were talking about the transitive property, I was saying to myself, I guess all of our stories— I mean, that's what really we're saying. All of our stories are the same. That's exactly right.

That's right. That's right.

And, and you really talk about that in Reunion. And I guess I would love to hear maybe you kind of connect the thread or build— draw the thread Reboot to Reunion.

Sure.

And why that was so important for you to write and kind of what people should know about it.

Well, you know, one of the core messages of Reboot, one of the core messages of all the work that I do, is a kind of obvious statement, which is that better humans make better leaders. And I always joke, well, if it's so obvious, why do we have such shitty leadership? And we have difficult leadership because the process of growing up, as you so well wrote about, the process of growing up is hard. It's something we choose not to do. Just like we're socialized not to, to have self-awareness, we're also socialized not to take responsibility for our internal state. We project that out into into the world.

And that—

those are all parts of the process of growing up. But if we stop the process there, then I think we fail to live up to a moral responsibility, which is, um, again— and I think you drew the conclusion correctly— All of our stories are each other's stories. We all want love, safety, and belonging. We all want to feel that we are in a community that accept us for who we are, warts and all. And if those of us who have power, and I believe business leaders have a tremendous amount of power, don't extend the work of radical self-inquiry into the larger realm of, and how have I been complicit in creating the conditions in the world that I say I don't want? You know, I don't know when we'll broadcast, but I'll tell you something. This past weekend, a white supremacist shot to death 3 Black folks shopping at a Dollar General store in Jacksonville, Florida. And last week, a 66-year-old mother of 9, a shop owner who refused to take down a Pride flag that she was flying outside of her store, was shot in the head and killed. It's getting worse. And the impulse that we have, just like the impulse that we have as business leaders to worry about oversharing or to worry that people are going to think we're weak and therefore not follow us, though the impulse that we have as leaders, as business people, is to say that's not really our realm, but it's the realm of your employees if it's not the realm of your children or your neighbors. And just like your story is my story, we live in an interdependent, interbeing world. And so my neighbor's burden is my burden. It is my responsibility, not solely, not exclusively, and not necessarily my responsibility, but it is my obligation to do something, to try.

Yeah, yeah. We have this sort of this phrase in Hebrew, lo alecha hamlech ha-ligmor. It's not your job to finish the work, but you have to get started.

I actually quote that in, in chapter 7 of the, of the book. It's, it, it is a powerful concept. It's a, it's a powerful wisdom teaching that encourages us to look past whether or not we have the capacity to heal the world and to do the work anyway.

Right, right. To do the work anyway. Exactly. Yeah, I think that's really powerful. And I appreciate, you know, the, the thread that you just drew. And in particular, I'm always struck— I'm just continuing to be struck by like all of our stories are the same. And what you talk about, you know, your story is my story, my story, our story is all of our stories. And when you talk about in the book is this notion of othering.

Right.

Um, I'd love to hear you talk about othering and, and what that is and, you know, sort of just some, some thoughts around it.

Sure. So we'll give credit where credit is due. Uh, the, the scholar John A. Powell working out of, um, UC Berkeley was the first person I heard use the term and it's an all-encompassing term to define the experience, uh, in a more broad setting. Sometimes language inhibits us, and so if we, if we think about racism in America, we tend to think of it in a black and white paradigm, and then maybe we might qualify and say, okay, well, anti-Asian racism Okay. But then there's a nativism and an anti-immigration feeling and an antisemitism and an anti— or, you know, transphobia and homophobia. And is there a way to really describe this experience that is broader than all of those terms? And I think that that word othering is a very, very powerful word because it implies breaking the bonds implicit in "Your Story Is My Story," that we are all connected, interconnected in some way. Even as our stories are different, they are still also the same. And when we make another person the other, more often than not, we make them a threat, and then we dehumanize them. And then as we dehumanize them, we make it possible to do horrific things to them, whether it's to, to create the largest, you know, church, you know, religious institution-related mass murder in the Pittsburgh synagogue or we, uh, put razor wire in the waters of the Rio Grande to stop an immigrant from crossing because our policies have failed us, our political leaders have failed us, and so children leave bits of flesh on razor wire. Okay. This is not the world I want to leave my children and grandchildren. This is an immoral, inhumane world. And I think it is our responsibility to lean against this kind of othering and to use what power and privilege we have to create a sense of what I refer to as systemic belonging, so that we can all sort of relax into feeling loved and safe. I think this is critical.

Yeah. So I have a kind of a, a macro question and a micro question. I think I'm going to start with a macro question. If you think about the world, like you're just saying, and, and I hear you on everything you say, and you wrote this, this book and, and really talked movingly about how important all these topics are. And I know either in your book or I heard you say somewhere that your daughter said to you, "It's not enough to be an ally, you have to be a co-conspirator." How— what should people do in the world in the macro way to be co-conspirators in building the kind of world that we all want to be part of?

Well, let me ask you a question. Um, so you reached— I'm imagining you said, if I remember correctly, "We have a saying," and you quoted the Hebrew.

Yeah.

So who are the "we"? Who's the "we"? Yeah.

Um, for me, it's we Jewish people. And also, I have to say, the tribe I belong to is my youth group tribe, who where I learned that expression. Yeah, okay, that's who we are.

So, so, so there's this powerful— like, I wish— I hope everyone gets to see the video so that everyone can see your face when I invoked the we to which you belong. Okay, so I would argue that the first step is to actually be in touch with the we to whom you belong. Whether it's your ancestors. You— let's just pause and acknowledge the pogroms, because the pogrom was not limited to just the Holocaust day. And so The Jewish people have been othered and continue to be othered and continue to be singled out every day.

True.

Even in the United States, even with the, the projections of power that may be placed upon people. Okay. From that place, evoke the empathy and realize that in different ways, the same inhumane, dehumanizing experience is happening all around us. And from that place, from your ancestors, call up the wisdom and the courage and the strength to say, "It is wrong to treat this person, to shoot this person because of who they love and how they love." It is wrong to deny them civil rights or human rights. It is wrong to deny them healthcare. See, if we can reunite— that's why I use that term reunion— if we can reunite with the true experience of those who came before us, we can access something glorious. Strength and wisdom. And then we create this greater sense of unity. In the book, I quote a poem by bell hooks, and it closes the book in a way. And she wrote, when angels speak of love, all things are union and reunion. There is no end to paradise. There is no end to separation. I mangled the quote, but you get the point. And I think there's wisdom in that.

Yeah, that's beautiful. It's beautiful. And I especially appreciate that it's like, in order to honor your ancestor, like the sort of who you come from, like your people, like you're allowed to have your people.

Yes.

And you can take all that, your peopledom, into the world and use that, which feels like a difference, but actually that is the point of the power that lets you reun, reun with other people.

That's right.

That's—

see, your story, your people's story of belonging to each other, is not all that different from my people's story of belonging. To each other, which means transitive nature, A equals C, which means our stories are more similar than they are dissimilar. And even though our individual experiences are different and those differences should be honored, the underlying connection, to my mind, fosters a deep and profound sense of empathy. See, we can't stand by and watch babies being murdered. And literally, it has come to that.

Mm-hmm.

Yeah, right. And, you know, if anyone is out there asking this, you know, well, what's a business person to do? Just start by acknowledging this. Right? It is not your work to complete, but neither are you at liberty to neglect the work.

Right, right, right.

You still have to do the work.

Very true, true, and, and very powerful. Um, and it, it gives, you know, I think it just gives some— you were talking earlier about energy— gives meaning, it gives energy. It helps drive forward in the day-to-day because it gives a lot of purpose to whatever you're doing. If that you see that this is part of your work in a way.

That's right. That's right.

Yeah. So I also told you I have a micro question.

Okay.

And so my micro question is about othering in the workplace because everything you just said as a society is so true, but also there's the jerk down the hall or the person you're in the Twitter fight with. And, You know, a lot. And the guy you can't stand, right? And like, um, maybe there's so many different caricatures of people that, you know, you just don't like, and then you make fun of them or talk about behind the back and whatever. And I think this— I think this powerful— this notion of othering people and healing that in yourself, yes, is very helpful. And by the way, focuses on belonging in the workplace, which is your microcosm of the world, but How do you acknowledge and notice that you're othering someone? And what are some, like, what are some strategies to notice that you're othering someone and then some strategies to bring empathy to the situation?

Well, it's not that dissimilar to what we were talking about before, right? It's like that radical self-inquiry becoming the foundational component of an experience, right? I would argue it's a foundational component of being an adult. So When I look at how I respond to this person, am I willing to ask a question like, what part of me have I projected into them such that I can have an over-the-top reaction to everything that they're doing? Okay, now that is an initial first step in an othering process, right? That's the first step in, in, in dismantling the structures. It might, it might come from the way in which I was socialized to approach a concept of race, or it might be the way I was socialized to, to approach a concept of gender, right? When, uh, and, and You and I encounter thousands of examples of this, but imagine the ways in which, um, in male-dominated environments, women's voices are silenced. Um, uh, what is the patriarchal structure that exists behind that? And we don't often look at it through that lens. We don't often look at the fact that we may have been socialized to minimize someone who identifies as female, whether or not we identify as female ourselves, and, and maximize someone who identifies as male, right? That is an incredibly common— so common as, as it's insidious— way we other within a work environment. Um, it's, it's, uh, you know, it, it requires the same basic tool set that I spoke about in Reboot, which is how have I been complicit in this condition? What am I doing? What am I really up to? And how do I take back the parts of my own self that I might not be so proud of? And projecting onto that other person.

Yeah, that's really helpful. Yeah, it comes back to radical self-inquiry and your willingness, you know, it's like the expression, I know Tim Ferriss has said it and others have said it, your life will be as good in direct proportion to the number of uncomfortable conversations you're willing to have. But that's also with yourself, right?

With yourself. That's right.

Right.

That's right, right.

I think that's so powerful. Um, Jerry, just a few more questions. I like to ask people on my show about imposter syndrome because that's a topic that has a lot of resonance. Have you ever experienced imposter syndrome or severe self-doubt?

Sure, every time I sit down to write a book.

So only, only twice then?

No, you're assuming that's the only time I've ever sat down to write. Um, Sure, all the time. I mean, you know, I'm leaning into a difficult topic, and so I'm leaning into that, and I experience that right now. Um, but, uh, I also have a different relationship with that part of my personality, and in that way, what I do is I see it as a protective voice that's trying to keep me from humiliation and shame. And when I hear those voices, that those voices of self-doubt come up and I am in my best self, what I can do at that point is tell that part of my psyche to stand down, that the risk isn't there. That even if someone doesn't like, say, my book, um, you know, I was actually just saying this today, not every song that Bruce Springsteen has written is something I love, but I still love Bruce Springsteen as a musician, right? And so I can take that in and realize some people are going to like Reboot, some people are going to like Reunion, some people are going to like both. Some people are not going to like one or the other, and that's just a fact. It's not a threat. And I think that that's another construct that can sort of ameliorate somewhat and mitigate that feeling.

That's great. That's just a fact, it's not a threat. That's very good. It's a good little pithy saying. I appreciate that. Jerry, what do you wish you had known earlier earlier on your journey?

Everything that I just said, um, and then some. That, um, I don't have to try as hard, um, and, and maybe the most powerful of which is that, um, love itself can be safe. That was something that was hard for me to internalize. I turned 60 this year and I very much feel like an elder. And as an elder, those are the sorts of things that I actually do share with my children who are 33, 30, and 26 respectively.

Good. It's good to pass down those lessons. They can make their own— they can make different mistakes then.

That's right, exactly.

That's right. Right. Last question, Jerry. What advice do you have for founders as they embark on their journeys to grow into leaders?

Be unafraid of looking in the mirror. It's not an act of narcissism. It's not a self-indulgence to really look at one's own self and one's own self-development as part and parcel with one's own leadership development. That's why better humans make better leaders.

Love it. Beautiful. Better humans make better leaders. I want to say thank you so much for joining me today. It was such a pleasure to have you.

Thank you, Alisa. It was really a delight speaking to you. No kidding. Thank you. Really fun.

Thank you. I appreciate that. I want to say to everybody, please pick up a copy of Reunion: Leadership and the Longing to Belong. Thanks again.

Thank you.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.