I tried to be a creative writer when I was younger. I was not very good at it. On the technical aspects of writing, I was solid. My problem was that I didnt understand people well enough to write a convincing character. Social adeptness isnt a prerequisite for being a strong writer, but a basic understanding of how most people think is necessary, and I didnt have that. One thing I remember, and I think it was my mother who first said to me: every character thinks of him- or herself as a main character. Thats what makes Rosencrantz and Guildenstern Are Dead (the play that begins by ribbing every Bayesian in the audience) great. In Hamlet, these guys are a sideshow, and can be disregarded as such (theyre symbolic of the princes sunnier past, now betrayers and otherwise irrelevant). From their perspective, they arent. Tom Stoppards play reminds us that whats remembered as one story, told in truth by its main protagonist, is actually one of a thousand possible, related but very different, tales.

Ive worked in an ungodly number of companies for someone my age, and Ive seen leadership done well and not-well, but only in the past 24 months have I really started to understand it. Why can some people lead, and others not? Why was I once so bad at leading other people? I think the core insight is the above. To lead people, you have to understand them and what they want, which usually requires recognition of the fact that they dont see themselves as followers innately. Theyll follow, if they can lead in other ways.

I dont intend for this to devolve into an everyone is special claim. Thats bullshit. I could say, everyone is special because every point in a high-dimensional space sees itself as an outlier, but that would be beside the point. Im not talking about capability or importance to any specific organization, but perspective only. I think most people are realistic about their importance to the various organizations they inhabit, which is often very low if those organizations are big. However, few people see themselves as supporting actors in life itself.

The problem that a lot of visionaries have is that they lose sight of this entirely. They expect others to subsume their lives into an ambitious idea, as they have done themselves, while failing to understand that others arent going to commit the same dedication unless they can take some ownership of the idea. The visionaries tend to cast themselves as the main players the saviors, architects, deal-makers and warriors while most of the others, within that organization, are supporting cast. Since they will never see themselves as subordinates in truth, there will always be a disconnect that disallows them from willingly putting their entire being into the vision or organization. Theyll subordinate a little bit of work, if they get paid for it. They wont subordinate themselves. Not for real.

This bias toward viewing others as supporting actors is dangerous. The problem isnt only that it can lead one to mistreat other people. Worse than that, it can lead toward systematically underestimating them, being underprepared for them to pursue their own agendas, and feeling a sense of betrayal when that happens. The worst thing about visionaries, in my view, isnt how they treat their supporters. Some are good in that way, and some are not, but only a couple that Ive known were reliably indecent. The problem with them, instead, is that they tend to be easy prey for sycophantic subordinates who often have bad intentions. They see the golden child as a docile, eager protege or a lesser version of themselves, when often that person is an exploitative sociopath who knows how to manipulate narcissists. Visionaries tend to see their organizations as benevolent dictatorships with no politics (its never politics to them because theyre in charge) while their organizations are often riddled with young-wolf conflicts that theyve inadvertently encouraged.

I dont know what the right answer is here. The word empathy comes to mind, but thats not what I mean. Reading emotions is one skill, but sometimes I wonder if its even possible to really get (as in understand) another person. I dont believe that, as humans, we really have the tools for that. Alternatively, people often talk about putting themselves in someone elses shoes (I could do a Carlin-esque rant about the colloquialism, but Ill skip it) but that is extremely difficult to do, because most people, when they attempt to do so, are heavily influenced by their own biases about that person.

Likewise, I cant claim in all honesty that any of this is my strong suit. Technical, intellectual, and cultural leadership are a 10/10 fit with my skill set and talents. On the other hand, leadership of people is still a major area for development. The somewhat cumbersome store of knowledge (and, I make no pretenses here, I do not claim the skills necessary to apply it) that I have on the topic is not from preternatural excellence (trust me, I dont have such) but from watching others fail so badly at it. I owe everything I know on the topic to those who, unlike me, were promoted before they outgrew their incompetence. So there are many questions here where I dont know the answers, and some where I dont even know the right questions, but I think I know where to begin, and that goes back to what every novelist must keep in mind: everyone is, from his or her own perspective, a main character.

I tried to be a creative writer when I was younger. I was not very good at it. On the technical aspects of writing, I was solid. My problem was that I didnt understand people well enough to write a convincing character. Social adeptness isnt a prerequisite for being a strong writer, but a basic understanding of how most people think is necessary, and I didnt have that. One thing I remember, and I think it was my mother who first said to me: every character thinks of him- or herself as a main character. Thats what makes Rosencrantz and Guildenstern Are Dead (the play that begins by ribbing every Bayesian in the audience) great. In Hamlet, these guys are a sideshow, and can be disregarded as such (theyre symbolic of the princes sunnier past, now betrayers and otherwise irrelevant). From their perspective, they arent. Tom Stoppards play reminds us that whats remembered as one story, told in truth by its main protagonist, is actually one of a thousand possible, related but very different, tales.

Ive worked in an ungodly number of companies for someone my age, and Ive seen leadership done well and not-well, but only in the past 24 months have I really started to understand it. Why can some people lead, and others not? Why was I once so bad at leading other people? I think the core insight is the above. To lead people, you have to understand them and what they want, which usually requires recognition of the fact that they dont see themselves as followers innately. Theyll follow, if they can lead in other ways.

I dont intend for this to devolve into an everyone is special claim. Thats bullshit. I could say, everyone is special because every point in a high-dimensional space sees itself as an outlier, but that would be beside the point. Im not talking about capability or importance to any specific organization, but perspective only. I think most people are realistic about their importance to the various organizations they inhabit, which is often very low if those organizations are big. However, few people see themselves as supporting actors in life itself.

The problem that a lot of visionaries have is that they lose sight of this entirely. They expect others to subsume their lives into an ambitious idea, as they have done themselves, while failing to understand that others arent going to commit the same dedication unless they can take some ownership of the idea. The visionaries tend to cast themselves as the main players the saviors, architects, deal-makers and warriors while most of the others, within that organization, are supporting cast. Since they will never see themselves as subordinates in truth, there will always be a disconnect that disallows them from willingly putting their entire being into the vision or organization. Theyll subordinate a little bit of work, if they get paid for it. They wont subordinate themselves. Not for real.

This bias toward viewing others as supporting actors is dangerous. The problem isnt only that it can lead one to mistreat other people. Worse than that, it can lead toward systematically underestimating them, being underprepared for them to pursue their own agendas, and feeling a sense of betrayal when that happens. The worst thing about visionaries, in my view, isnt how they treat their supporters. Some are good in that way, and some are not, but only a couple that Ive known were reliably indecent. The problem with them, instead, is that they tend to be easy prey for sycophantic subordinates who often have bad intentions. They see the golden child as a docile, eager protege or a lesser version of themselves, when often that person is an exploitative sociopath who knows how to manipulate narcissists. Visionaries tend to see their organizations as benevolent dictatorships with no politics (its never politics to them because theyre in charge) while their organizations are often riddled with young-wolf conflicts that theyve inadvertently encouraged.

I dont know what the right answer is here. The word empathy comes to mind, but thats not what I mean. Reading emotions is one skill, but sometimes I wonder if its even possible to really get (as in understand) another person. I dont believe that, as humans, we really have the tools for that. Alternatively, people often talk about putting themselves in someone elses shoes (I could do a Carlin-esque rant about the colloquialism, but Ill skip it) but that is extremely difficult to do, because most people, when they attempt to do so, are heavily influenced by their own biases about that person.

Likewise, I cant claim in all honesty that any of this is my strong suit. Technical, intellectual, and cultural leadership are a 10/10 fit with my skill set and talents. On the other hand, leadership of people is still a major area for development. The somewhat cumbersome store of knowledge (and, I make no pretenses here, I do not claim the skills necessary to apply it) that I have on the topic is not from preternatural excellence (trust me, I dont have such) but from watching others fail so badly at it. I owe everything I know on the topic to those who, unlike me, were promoted before they outgrew their incompetence. So there are many questions here where I dont know the answers, and some where I dont even know the right questions, but I think I know where to begin, and that goes back to what every novelist must keep in mind: everyone is, from his or her own perspective, a main character.

I tried to be a creative writer when I was younger. I was not very good at it. On the technical aspects of writing, I was solid. My problem was that I didnt understand people well enough to write a convincing character. Social adeptness isnt a prerequisite for being a strong writer, but a basic understanding of how most people think is necessary, and I didnt have that. One thing I remember, and I think it was my mother who first said to me: every character thinks of him- or herself as a main character. Thats what makes Rosencrantz and Guildenstern Are Dead (the play that begins by ribbing every Bayesian in the audience) great. In Hamlet, these guys are a sideshow, and can be disregarded as such (theyre symbolic of the princes sunnier past, now betrayers and otherwise irrelevant). From their perspective, they arent. Tom Stoppards play reminds us that whats remembered as one story, told in truth by its main protagonist, is actually one of a thousand possible, related but very different, tales.

Ive worked in an ungodly number of companies for someone my age, and Ive seen leadership done well and not-well, but only in the past 24 months have I really started to understand it. Why can some people lead, and others not? Why was I once so bad at leading other people? I think the core insight is the above. To lead people, you have to understand them and what they want, which usually requires recognition of the fact that they dont see themselves as followers innately. Theyll follow, if they can lead in other ways.

I dont intend for this to devolve into an everyone is special claim. Thats bullshit. I could say, everyone is special because every point in a high-dimensional space sees itself as an outlier, but that would be beside the point. Im not talking about capability or importance to any specific organization, but perspective only. I think most people are realistic about their importance to the various organizations they inhabit, which is often very low if those organizations are big. However, few people see themselves as supporting actors in life itself.

The problem that a lot of visionaries have is that they lose sight of this entirely. They expect others to subsume their lives into an ambitious idea, as they have done themselves, while failing to understand that others arent going to commit the same dedication unless they can take some ownership of the idea. The visionaries tend to cast themselves as the main players the saviors, architects, deal-makers and warriors while most of the others, within that organization, are supporting cast. Since they will never see themselves as subordinates in truth, there will always be a disconnect that disallows them from willingly putting their entire being into the vision or organization. Theyll subordinate a little bit of work, if they get paid for it. They wont subordinate themselves. Not for real.

This bias toward viewing others as supporting actors is dangerous. The problem isnt only that it can lead one to mistreat other people. Worse than that, it can lead toward systematically underestimating them, being underprepared for them to pursue their own agendas, and feeling a sense of betrayal when that happens. The worst thing about visionaries, in my view, isnt how they treat their supporters. Some are good in that way, and some are not, but only a couple that Ive known were reliably indecent. The problem with them, instead, is that they tend to be easy prey for sycophantic subordinates who often have bad intentions. They see the golden child as a docile, eager protege or a lesser version of themselves, when often that person is an exploitative sociopath who knows how to manipulate narcissists. Visionaries tend to see their organizations as benevolent dictatorships with no politics (its never politics to them because theyre in charge) while their organizations are often riddled with young-wolf conflicts that theyve inadvertently encouraged.

I dont know what the right answer is here. The word empathy comes to mind, but thats not what I mean. Reading emotions is one skill, but sometimes I wonder if its even possible to really get (as in understand) another person. I dont believe that, as humans, we really have the tools for that. Alternatively, people often talk about putting themselves in someone elses shoes (I could do a Carlin-esque rant about the colloquialism, but Ill skip it) but that is extremely difficult to do, because most people, when they attempt to do so, are heavily influenced by their own biases about that person.

Likewise, I cant claim in all honesty that any of this is my strong suit. Technical, intellectual, and cultural leadership are a 10/10 fit with my skill set and talents. On the other hand, leadership of people is still a major area for development. The somewhat cumbersome store of knowledge (and, I make no pretenses here, I do not claim the skills necessary to apply it) that I have on the topic is not from preternatural excellence (trust me, I dont have such) but from watching others fail so badly at it. I owe everything I know on the topic to those who, unlike me, were promoted before they outgrew their incompetence. So there are many questions here where I dont know the answers, and some where I dont even know the right questions, but I think I know where to begin, and that goes back to what every novelist must keep in mind: everyone is, from his or her own perspective, a main character.

I tried to be a creative writer when I was younger. I was not very good at it. On the technical aspects of writing, I was solid. My problem was that I didn’t understand people well enough to write a convincing character. Social adeptness isn’t a prerequisite for being a strong writer, but a basic understanding of how most people think is necessary, and I didn’t have that. One thing I remember, and I think it was my mother who first said to me: every character thinks of him- or herself as a main character. That’s what makes Rosencrantz and Guildenstern Are Dead (the play that begins by ribbing every Bayesian in the audience) great. In Hamlet, these guys are a sideshow, and can be disregarded as such (they’re symbolic of the prince’s sunnier past, now betrayers and otherwise irrelevant). From their perspective, they aren’t. Tom Stoppard’s play reminds us that what’s remembered as one story, told in truth by its main protagonist, is actually one of a thousand possible, related but very different, tales.

I’ve worked in an ungodly number of companies for someone my age, and I’ve seen leadership done well and not-well, but only in the past 24 months have I really started to understand it. Why can some people lead, and others not? Why was I once so bad at leading other people? I think the core insight is the above. To lead people, you have to understand them and what they want, which usually requires recognition of the fact that they don’t see themselves as followers innately. They’ll follow, if they can lead in other ways.

I don’t intend for this to devolve into an “everyone is special” claim. That’s bullshit. I could say, “everyone is special because every point in a high-dimensional space sees itself as an outlier”, but that would be beside the point. I’m not talking about capability or importance to any specific organization, but perspective only. I think most people are realistic about their importance to the various organizations they inhabit, which is often very low if those organizations are big. However, few people see themselves as supporting actors in life itself.

The problem that a lot of “visionaries” have is that they lose sight of this entirely. They expect others to subsume their lives into an ambitious idea, as they have done themselves, while failing to understand that others aren’t going to commit the same dedication unless they can take some ownership of the idea. The visionaries tend to cast themselves as the main players– the saviors, architects, deal-makers and warriors– while most of the others, within that organization, are supporting cast. Since they will never see themselves as subordinates in truth, there will always be a disconnect that disallows them from willingly putting their entire being into the vision or organization. They’ll subordinate a little bit of work, if they get paid for it. They won’t subordinate themselves. Not for real.

This bias– toward viewing others as supporting actors– is dangerous. The problem isn’t only that it can lead one to mistreat other people. Worse than that, it can lead toward systematically underestimating them, being underprepared for them to pursue their own agendas, and feeling a sense of betrayal when that happens. The worst thing about “visionaries”, in my view, isn’t how they treat their supporters. Some are good in that way, and some are not, but only a couple that I’ve known were reliably indecent. The problem with them, instead, is that they tend to be easy prey for sycophantic subordinates who often have bad intentions. They see the “golden child” as a docile, eager protege or a lesser version of themselves, when often that person is an exploitative sociopath who knows how to manipulate narcissists. Visionaries tend to see their organizations as benevolent dictatorships with “no politics” (it’s never politics to them because they’re in charge) while their organizations are often riddled with young-wolf conflicts that they’ve inadvertently encouraged.

I don’t know what the right answer is here. The word “empathy” comes to mind, but that’s not what I mean. Reading emotions is one skill, but sometimes I wonder if it’s even possible to really “get” (as in understand) another person. I don’t believe that, as humans, we really have the tools for that. Alternatively, people often talk about putting themselves “in someone else’s shoes” (I could do a Carlin-esque rant about the colloquialism, but I’ll skip it) but that is extremely difficult to do, because most people, when they attempt to do so, are heavily influenced by their own biases about that person.

Likewise, I can’t claim in all honesty that any of this is my strong suit. Technical, intellectual, and cultural leadership are a 10/10 fit with my skill set and talents. On the other hand, leadership of people is still a major area for development. The somewhat cumbersome store of knowledge (and, I make no pretenses here, I do not claim the skills necessary to apply it) that I have on the topic is not from preternatural excellence (trust me, I don’t have such) but from watching others fail so badly at it. I owe everything I know on the topic to those who, unlike me, were promoted before they outgrew their incompetence. So there are many questions here where I don’t know the answers, and some where I don’t even know the right questions, but I think I know where to begin, and that goes back to what every novelist must keep in mind: everyone is, from his or her own perspective, a main character.