Large-Group Leadership

As a group grows, we have a harder time personally connecting with everyone in that group. Starting around 20 people, other members can just as often be acquaintances as close friends. We hit a hard limit on human interaction at about 150 people, both psychologically and logistically.

A social network user, a citizen of a city or country, an employee of a corporation, and a member of a large club are all functionally in a large group. Broadly speaking, modern society consists mostly of large groups, segmented into smaller groups according to who and what’s most convenient or familiar.

We tend to purpose ourselves toward larger groups for several reasons:

  1. Larger groups give us the impression of security against things we fear.
  2. Each person is capable of heavily specializing in things they want and giving others what they specialize in.
  3. Everyone amasses more shared knowledge, meaning cutting down on work.

In larger groups, we tend to associate with a few people in that group and maintain many acquaintances. Some people, like leaders, have many more connections, but there are too many people in a large group to stay in touch with all of them.


Large groups feel like a massive, monolithic entity, but they’re made of the combined souls in that group, vaguely oriented toward the leaders’ communicated purpose. Unlike smaller groups, though, that purpose can be very far-removed from the leaders’ guidance.

As groups become progressively larger, top-ranking people will become dramatically more powerful than low-ranking ones to create a class divide. To prevent too much in-fighting, the people at the top will naturally convey an image that dilutes how much power they legitimately have:

  • Leaders will have others introduce them before they speak.
  • Knowledge experts will use language to imply they’re uncertain.
  • Multimillionaires will wear working-class clothing or avoid showing their wealth.
  • Religious leaders will feign humility (e.g., “I’m the worst of sinners”).

To have a clear understanding of any group, an observer needs to see 3 perspectives at once:

  1. Legal entity: It’s a separate existence which makes its own collective decisions, though its civil rights are generally treated as sub-human.
  2. Holistic entity: It’s made of people, most of them normal workers doing various specialized roles, and some of those are only partly of that entity (e.g., contractors) and others with more power (e.g., shareholders, leadership).
  3. Power: It advances an agenda, defined and curated by its leadership, which impacts its individual members and other people around it.

Unlike leaders in times past, their effort is to identify with the rest of the people instead of demonstrating raw force. It’s influence via being relatable instead of through fear.

Leaders must reflect values that align with the purpose of the organization. If they ever break from it, the organization will change in different directions. At its worst, it becomes an inter-group conflict or a bad system. Leaders have so many observers that they must publicly identify with those values, or they’ll sow dissent among the members.

More than anything, the group’s represented value will bind all the members together through a shared belief in emotionally-similar consequences. Fear of adverse effects is the greatest motivator to get everyone together, which is rarely subtle.


Every large group was once a small group, but kept growing. Any large group that takes decades to grow will have its own distinct culture that members pressure new members to adopt. Members in rapidly-grown groups tend to maintain their old cultures as they come in, meaning the group adopts a strange hybrid of everyone’s background and is easily dispersed by comparison.

More cultures can resonate with an organization that promotes very fewer values, so an organization grows proportionally to how few values it conveys, assuming it has mass exposure. At the same time, many values allow a clearer group identity. At the same time, stated values that aren’t shown can cause the entire culture to backfire and break apart.

As a group grows, each individual’s influence in the group becomes more specialized. Members’ tasks become more specific, and many leaders are simply a “connecting-point” to other smaller sections of the group. Once this starts happening, most members will become more apathetic to the group’s causes and the group will feel more inhuman, irrespective of how relatable or noble its origins were.

Over time, members’ specializations in various aspects will create special-purpose authorities beyond the central leadership roles (e.g., bureaus, coalitions). Bureaucracy is when those bureaus have most of the power, and they are sub-groups of their own inside the meta-group that are subject to inter-group conflicts and misunderstandings.

Since every person has their own reaction to new information, unexpected consequences will come from any large decision proportionally to the size of the group. The only way to plan ahead is to consult history. Otherwise, the group should make plans for a trial-and-error endeavor, along with the resources to hedge the inevitable risks from those decisions.

As a group expands, leaders don’t see results as immediately as they had in a small group. For that reason, their inherent aptitude creates the ceiling of the group’s size, and it’s harder for them to learn how to lead through simple trial-and-error.

All the unpredictable elements of a small group compound across many people in a large group. There are more power dynamics, more purposes that diverge from the group’s, and usually a broader mix of cultures. Each leader’s ability to manage a small group will be challenged in completely new directions, especially regarding human universal tendencies to be lazy, evil, and engage in conflicts.

When the scale becomes enormous (i.e., surpassing thousands), every large group leader must act very quickly to keep the entire organization in line. Their role frequently becomes a never-ending string of resolving disasters.

Large groups are far more risk-averse than small groups, since they have so much more power to lose and so much more easily. They’re also susceptible to trust other large groups more, since they often depend so heavily on them for their large-scale resource needs.

To gather more understanding or certainty, most large systems give formalized tests. While these tests can clarify, they represent tremendous power to the members, who will immediately find ways to cheat on the test. Thus, while leaders often trust the tests, they’re one of the quickest ways to make a dysfunctional organization if everyone knows what they’re used for.


In any formal hierarchy or organization structure, power is abstracted and redistributed proportional to its rigidity. This makes large groups more able to perform gargantuan tasks (which are often easy to measure), even while being completely non-human in how they do it. The highest form of this abstraction comes through money.

Unlike a smaller group with an organization run by the personality and decisions of a few leaders, larger groups consist of a very formalized hierarchy of leadership, often at least three layers deep (e.g., boss, his boss, and the CEO).

Top leaders are usually at least 2-3 degrees removed from any actual work done, but they’re responsible for making all the decisions. If trends or technology change, they must stay aware of it or the entire group will become irrelevant. This is why most top leaders spend most of their time communicating and consuming information, and why they’re not very useful in any practical sense.

Often, top leaders will let lower-ranking leaders of smaller sub-groups have unique roles. This ranges by how much trust the leaders give, and can range from the top leader merely existing as a symbolic “publishing” or “producing” role all the way to completely micromanaging the sub-group. Absolutely nobody ever likes being micro-managed, and it’s the product of a dysfunctional system caused by bad leadership not respecting individual decision.

Middle leaders (e.g., middle management) are effectively an extension of their top leadership to manage the bottom leadership. Middle leadership often makes very few decisions compared to the top and bottom leadership. However, their willingness to comply with the organization’s policies keeps the entire organization unified in purpose (or, at least, the appearance of it). In practice, most middle management is simply the above-stated “connecting-point” to other sub-groups.

Leadership getting feedback about the members, and acting on it, is critical for the entire group’s success, and the entire group can become dysfunctional surprisingly easily. Leadership failures usually come from incompetence more than malice, though their public image may imply something else.


Top leaders only have limited influence over the entire group’s culture. They only maintain it by making specific decisions that craft an image for everyone to interpret for themselves. That image promotes collective values (at least in appearance) that everyone holds to:

  1. Messages to everyone in the group about the shared purpose they’re all aspiring toward.
  2. Appointing, promoting, disciplining, and dismissing sub-leaders who conform with the culture they want to promote.
  3. Encounters with the sub-leadership and very limited encounters with the lower-ranking members to rally everyone toward that stated purpose and sort out details.
  4. Officially declared, often written, policies and procedures, enforcing them, or changing them.

These decisions are always designed for the interests of the people in the group or the people the group favors. For that reason, a group won’t generally affect others it doesn’t favor or assimilate already unless it’s facing competition with another group that may serve those other people or subduing those people for another purpose.

Members’ awareness of each large-scale decision ripples outward like a trend at the speed of technology. It has a formative time with sub-leaders, then transitions outward to the majority, with the laggards never aware of the decision. This trend sticks proportional to the leadership skills of the top leader.

Low-ranking members have much less freedom than if they were in a smaller group, since the leadership redirects most of the lower ranks’ power to other purposes. Low-rank members won’t usually trust their large group much, since they’re not given much freedom, but they pretend to well enough that most leaders don’t realize this.


The sub-leaders each create their own subculture inside that group’s broader culture. They’ll appoint their own sub-leaders and dictate their own rules.

The differences between individuals in the large group are often greater than the proposed differences between the groups. However, because of ego issues coming from the top leadership, those groups will never converge until there’s a greater threat from the outside. This will almost certainly happen if they become obsolete from other, different groups coming in.

One of the most prominent conflicts for all sub-leaders is whether to enforce a rule that became obsolete from the situation changing. Often, this becomes a battle between morality and maintaining image.

Each sub-group ends up behaving precisely like its own small group, with a few notable exceptions:

  1. There’s a more complex distribution of power and redirection of resources toward purposes that many of the members don’t know than a smaller group.
  2. Everyone in a sub-group has many many additional resources available than an independent group would have.
  3. The large-scale leader’s decisions have a far-reaching, soft effect. Everyone feels like they’re part of the organization without as much evidence as a small group, even when they’re in a well-connected sub-group.

Each sub-group usually has different purposes to accomplish, and they redefine their culture around those purposes. This can create dramatic differences among sub-groups in the same large group.

Even in a complete autocracy, the presence of others’ decisions in carrying out the dictator’s authority dilutes the power dynamic across multiple people. This makes all systems subject to tampering and misuse.

In open-ended leadership (i.e., the sub-leaders run everything) the sub-leaders have the final authority to mismanage as they please. Thus, a central leader who can’t or won’t punish evil will empower it and the group will partly devolve.

These subcultures affect each other to create the aggregate group culture, with each one being its own “unit” interacting with other “units”. As various sub-groups gain or lose power, the organization travels through eras of control. Those eras create the shared culture and identity of the group.

The traditions that the subcultures make pile together over time. If those traditions keep accumulating but aren’t removed as the members who found meaning through those traditions leave that group, the group will slowly become a bad system. Unfortunately, the changes must be gradual or the entire group will have a complete meltdown.

Social Engineering

Instead of stopping people from doing what they want with rules, social engineering involves using rules to make people want to do something (“libertarian paternalism”).

Every large organization will try to socially engineer, at least a little. Even if they don’t have the power to do it, the draw from how much power they can gain is too tempting to pass up.

Social engineering is risky, proportionally to how much it’s done. Human nature hates to be “boxed in”, but leaders’ human nature won’t let them easily reverse a bad decision, so it often becomes a bad system in the process of trying to craft an ideal.

Every imposed rule can hurt people and damage purposes, and social engineering is trying to use the bludgeoning force of the law to coax, so it usually leads to negative externalities (e.g., overlooking people who don’t precisely quality for beneficial things, or shouldn’t qualify for beneficial things but still do).

Taxing, especially, will broadly destroy purposes:

  • Taxing anything far enough will motivate people to subvert the rules entirely.
  • Taxing what people produce makes people want to create less.
  • Taxing what people consume makes them less likely to consume.
  • Taxing taboo things too much without completely outlawing it often makes the organization depend on that thing for income.
  • Taking enough from the rich makes removes the incentive for the middle class to take risks to become rich, and is never enough in a large system to balance the group’s budget alone.
  • Taking enough from the middle class often makes them become the lower class.
  • Taking enough from the lower class is almost completely evil, since it barely benefits the leadership and hurts those with the least power.
  • In fact, the only fair tax is a progressive tax up to a specific level of survival, then everything else from middle class onward as a flat and non-negotiable percentage.

When a bad system starts socially engineering, they’re often operating off theories mixed with trial-and-error. This can be utterly disastrous, and often leads to social unrest, people losing property, and people dying.


Every far-reaching decision in a large group requires a lead time between communicating it and everyone doing it. That can range from minutes to weeks, depending on the technology available for communicating and acting. If the group has any dysfunction or it’s a particularly unexpected task by most of the group, it’ll take much longer or may result in an inner conflict where the task is never performed.

Every single result of an organization is created by the members’ decisions and actions. Thus, even when the leaders get all the credit or it or it had a debatable morality, every member was partly responsible for it in their own small way.

Like individual human purposes, large groups are always concerned with growing when they’re not facing a challenge to their existing power. They tend to grow their power both outward and upward:

The best analysis in the world can’t calculate all the variables of a large group, since it’s impossible to grasp everything that happens or might happen at any slice of time. Thus, the group will always create statistical outliers that don’t match the group’s purpose, no matter what decision they make.

While it’s impossible to track how a group will respond, there are a few conditions to more easily track changes:

  1. Make frequent, small decisions and poll the results over time. This permits the group to adapt to trends before another trend hits.
  2. Maintain an endless image management that stays up-to-date with every change.
  3. Expect that history never repeats itself, but has a similar pattern. It’s never the same because the culture is different between both cases of making a decision, sometimes simply because the decision had been made and people remember!
  4. Always give approximate estimates, and avoid trusting something simply because it was mathematically communicated.

Many inter-group conflicts can adapt and change groups. This change can be surprisingly fast or only change its external image, depending on how the leadership handles it. Since there’s so much power in a group, they tend to persist indefinitely in some form or another unless they’re destroyed or merged into another group.

However, with very few exceptions, the members who engage in most inter-group conflicts float through a unique sequence:

  1. They sincerely believe they can dramatically fix some of the issues within the group.
  2. They’ll make bold actions (e.g., communicating, building) to transform that group for the better.
  3. To survive in the group, they’ll eventually need to compete with other members of the group, so they’ll compromise their message.
  4. If they don’t become one of the leadership or give up, the group’s leadership will eventually eject them as a pariah/heretic or will outright kill them.


The leadership of most large groups treat the entire group as a singular entity, then compare themselves to other groups. When other groups outperform that group (e.g., technology, size, achievements), human nature works at scale and they try to outperform them.

Some of them will perform noble achievements in response to the challenge, but most of them become bad systems through a few avenues:

  • Banding together and allying with other groups that do not share the same values, leaving the entire group as a morass of mixed ideals.
  • Stealing from the other group and trying to imitate their success, but without the strength the first group had developed from having to work at it.
  • Attacking the other group and either destroying them or taking their things.

However, if a large group doesn’t have a purpose outside itself via competition, it’ll start getting restless and destroy things.

In short, large groups must always be acting toward a fixed purpose they believe they can perform without outside help, or they will descend into chaos and destroy or disband.


Each person has their own feelings and opinions, so a group’s purpose doesn’t necessarily resonate with each person. However, each group promotes a set of values, and every member has at least some association with at least some of those values.

A group is made of its members, so every individual person entering or leaving a group changes the group’s culture. A large and long-standing group won’t change as much from 1 person, but the progressive changes of the group through membership always express a trend over months and years.

Since fear binds people together, and fear is rarely subtle, most extremely large groups tend to operate as diametric opponents of one another (e.g., conservative/liberal, Christian/secular, Star Wars/Star Trek)

As groups scale, leaders must adopt a hands-off approach. They must make better decisions about who to appoint, and fewer decisions about anything anyone actually does.

Large group leaders must juggle way too many competing values and subcultures to maintain much sense of order. For this reason, groups that scale become ever-increasingly awful at doing what they were originally purposed to do.

An executive needs many specific background elements that allow you to perform and relate:

  • Change many job functions across many jobs, but stay in one industry.
  • Have either over a decade of relevant management experience or an MBA from a pedigreed university.
  • Live in a large metropolitan melting pot (e.g., New York City, Mumbai, Singapore).
  • Avoid living in culturally homogenous metro areas (e.g., Houston, Washington DC, Madrid).
  • Gain a slight advantage by being male.

To determine a high-quality leader, observe someone’s small-group leadership first, which often goes back to their parenting skills.

Leaders can’t create ideals for their entire group. They must consider their members’ purposes and their public image, along with other groups’ power over them. Thus, they’re not entirely responsible for anything the group does, and serve more as an image of the group’s goals.

Most large organizations create homogeneous experiences to promote a shared image and value system. This will usually knock off some of the formerly small group’s core personality, but will also permit it to grow indefinitely.

The CEO of McDonald’s has more in common with the CEO of Ford than the service workers of McDonald’s. A CEO’s job is the same in both: decide with several layers of abstraction from any work done the public can see, often with nearby assistants performing research for them.

Over time, large groups must make dramatic decisions that transform everyone in the group. There are many factors to consider, so most successful leaders consume high-quality creations, sharpen their intuition, and trust it profusely. This usually works, but a leader’s bad day through the influence of 1 relatively unimportant person’s failure can affect thousands or millions of people.

People individually can only handle so much change over a small window of time before they lose their mind. Organizations are the same, proportionally to the aggregate of their openness to new experiences minus their failings in communication.

Gossip travels quickly, so an organization that lies will rapidly become dysfunctional.

As of 2022, the USA’s Income Tax Code socially engineers every resident of the USA to become the following:

  1. Married with 2-3 children
  2. College graduates with a student loan
  3. Working a career as an educator
  4. Paying off a mortgage on a house
  5. Investing into a retirement account, preferably a 401(k) or 403(b)
  6. Generally unaware of the above

Since large-scale leaders must be self-conscious, their personalities are usually not very interesting, which is why the elite class of a free society is made of the same cut of boring, influential workaholics.

There are only two ways to make large-scale changes in a large group:

  1. Sacrifice your reputation and influence in a spectacular public display in the hopes of influencing others toward your beliefs after you’re gone.
  2. Find like-minded people and break off with them as an entirely separate group, which is only possible if you have the power to do it (or the creativity to find a way).