The Work-From-Home Future Is Destroying Bosses' Brains

Yesterday, Silicon Valley Analyst Jeremiah Owyang vaguely reported that executives are scared of their employees “working part-time (but paid full salary)” and “even working on side hustle startups, while on a full-time salary,” a truly terrifying prospect that has chilled me to the bone.

This may seem like just one fellow who has stepped on a giant rake, but Jeremiah has unfortunately burrowed into a core issue that’s going to come up as a result of the remote work being fairly mandatory during the pandemic. There is now a fight for the very soul of hiring - the very reason that we hire people, and what our expectations are versus what we’ve told them they are.

Let’s break apart this anxiety - executives have hired people full-time, and in this case I assume that the work that they’re required to do is done in part-time hours. These people are either “working part-time hours” or “doing side hustle startups,” and bosses want them back in the office, ostensibly to put an end to this practice. As I hinted at in Monday’s Substack, “remote work inherently messes with the power dynamic of the worker and the boss, and it is going to make many, many brains malfunction.” The reason isn’t just about control, but the very fabric of how employment or contract work is designed, and the way in which we have been conditioned to view labor.

The issue at its core is that bosses hiring people “full-time” often do so, as dramatic as it sounds, to capture their soul. Within the hours of 9 to 5 (but let’s be real, it’s more than that), they expect to own the time, attention and energy of that person. The nebulous badge of “full-time” brings with it a level of ownership of the person - they cannot go elsewhere, what they create is yours, on some level they are yours, because you have deigned them worthy of a salary and benefits and whatever other crumbs you pass their way. In return, you expect them to dedicate their existence to you - on levels of dramatic ranging from “I need to see you in the office” to “I want to make sure I can text you at 10PM and badger you about some shit that bothers me.”

The drumbeat around hybrid work is not remotely about spontaneity or collaboration, deep down. Sure, there’s a vague element of “it’d be nice to see everyone,” but I think at the core there’s just an expectation that people have done this for years, and thus it’s the way things work. Societal memes spread around the idea of hallway conversations or chance encounters that somehow inform the future of the company, with very little regard for their actual existence. And, if I may be a little dark, I think that there is an executive function that asks “what am I getting for this money?” and doesn’t want to admit that part of that thing they’re getting is a person’s physical presence as well as the time, so that they may feel that they own them.

Now, of course, everyone has had a boss that seemingly breaks all of these rules. They’re off on vacations all the time, or they’re taking meetings that take 3 hours and they come back drunk, or they’re simply working from home “because they had late calls.” And, of course, Silicon Valley in particular lionizes founders with multiple projects and investments, while spitting on workers who may do the same.

Hybrid work is not something that can be done simply by spending some days at home and some days at work. There must be a value proposition for going back to the office.

Sadly, this isn’t what most bosses think of when they perceive an office. Much like many of the structures that we’ve built around work, the office is assumed to be good for something, but really is a mechanism for capturing and restraining the laborer.

Just like middle managers.

The Middle Manager Issue

My father’s most specific advice on being a dad is that you learn two things from your parents - how to be a parent, and how not to be a parent. It’s also great advice when it comes to being a boss - you learn through both terrible and great bosses how to motivate people and how to get them to do stuff. The problem is that many people don’t actually learn a single thing from a bad boss, thinking that the reason that they became the boss was because they commoditized labor and treated people like shit, and that was part of the reward.

The masters of the current working society have told a giant lie around corporate advancement, specifically that people “don’t just want money, they want to feel part of something.” While this statement is technically true, a lot of companies read the sentence with either a bolded or entirely-removed “just,” parsing the sentence as a means to not pay people more, but to reward them with new titles and the ability to be mini-bosses in a larger empire, regardless of whether they’re actually good at or capable of managing people as anything other than a feudal lord.

The other part of this issue is that promotions and career advancement have been tied, on some level, to years of service, rewarding people who are good at not getting fired rather than good at their jobs. We have tied the vague idea of management so tightly to career advancement that we simply make people managers as a rite of passage - we think that because they’re good at their job they can either make people good at their jobs or watch people be good at their jobs and make them do them more. This is a dysfunctional view of work on three levels:

  1. Management is not being good the same thing as being at your job.

  2. We incentivize management as a control mechanism rather than a motivational and organizational mechanism in an organization, meaning that most middle managers are glorified cops.

  3. Middle managers are often graded on the work of their team, which means that they are actively incentivized to steal work and do little of their own.

Now, someone insufferable will read this and say “NOT ALL MIDDLE MANAGERS,” and let me tell you, if you’re thinking that, you are probably part of the problem. The reward system on the corporate ladder has become inextricably attached to a kind of professional abuse - that the only way to rise within a company is to be able to “take control” of a department and its people. This incentivizes those who are able to claim other people’s work and “make them” do things, while also actively deincentivizing being good at your job - middle managers are rewarded when they can take work from those who are good at their work but aren’t paid a manager’s salary.

Why? Because there are many CEOs (and VPs, and so on) that have got there with the joyous idea that the reason you become a CEO is to get paid for other people’s labor, which also means you don’t have to work. That’s also because the modern corporate interpretation of capitalism is inherently patriarchal - borne from the prospect that we all look up to someone, and we must learn from them and grow from them, until we eventually go and make our own children (companies). But until then, we’re under their “care” but also the rule of their law.

This is a misinterpretation of what capitalism is (for better or for worse, the most efficient extraction of money from labor - which also means getting the most from workers), and what attracts people to management roles (misinterpreting control as an efficient way of extracting value). The reason that there are so many bad managers - middle and otherwise - is that lots of people see management as delegation of work that you take credit for, mostly because that’s how many corporations function on a grand scheme. It’s framed palatably as contributing a small piece to a larger whole, but middle management’s truly noxious existence proves that people absolutely love it. The attraction to these positions isn’t what a true manager is - fostering talent, making the company better, getting more done, winning together - it’s about control and abuse.

These people are so prevalent because most companies aren’t okay with the obvious way to make people who are good at their jobs happy - paying them more money. Management titles are bargaining chips that work with people because they sound good to their friends and on LinkedIn, but those who are excited about them are usually not excited about the prospect of managing.

I rarely have run into a manager that has actually kept doing the job. In my profession, middle managers usually worked the longest hours but contributed the least, but were somehow graded based on my performance, as if their existence was the lightning rod.

Another issue is that we as a professional society continually reward useless brainstorming and “ideation.” Ideation without creation is wasted oxygen.

The Remote Breakdown

The reason that remote work is so threatening to a lot of corporate thinkers is that it largely devalues the middle management layer that corporate society is built on. When you’re in person, a middle manager can walk the floors, “keep an eye on people” and, in meetings, “speak for the group.” While this can happen over Zoom and Slack, it becomes significantly more apparent who actually did the work, because you can digitally evaluate where the work is coming from.

Zoom also makes it far more difficult to justify useless brainstorming activities - if you’re all sat on a call, still at your computer and capable of doing other things while you’re doing so, it’s so obvious how much time is wasted. You could (and probably do!) do work during these calls, and the more work you find yourself doing during the call, the more obvious the time is wasted. And, when distanced from the power dynamics of where people are sat in an office - the private office for the manager versus cubicle for the worker - you are no longer bound by the constructs that framed how you’d perceive someone and their work.

Also, while reducing people to windows or computer screens can be bad, it also makes evaluating people’s outputs easier. While there are always soft contributions - people that inspire others with ideas, people that do truly help mentor others - it becomes far less palatable to have someone you’re paying well who’s position appears to be “tells other people what to do.” Manager contributions are vastly overemphasized in person - they walk from meeting to meeting in full consternation, they go to people’s desks, it’s all very dramatic and visual and thus justifies the expense.

And these people are fuckin’ cops, man! Many managers take the idea that a manager is meant to evaluate and foster talent and read it as policing their every action, assuming that their manager status makes them perfect. They police your attendance, your output, if you “look productive,” all things that are so much less tangible in a remote world.

This cop attitude naturally ends at a point where you are expected to “give them your respect,” and the classic manager failure dance when they say “I have 15 years of experience.” The moment anyone tells me that I usually stop listening.

I also add that a lot of these middle management statements I’m making can be applied to bosses in general, which is part of the reason that many of these boss types are absolutely shitting the bed around the prospect of people staying remote. Generally, people are attracted to and inspired by leaders that lead by doing stuff - by doing work, by putting themselves on the line, by compensating people for their work and, ideally, providing fulfilling and meaningful work for them to do.

But bosses have been educated to believe that the reason that people are loyal to them is because people look up to you based on your experience and your past triumphs, as well as the fact that you are “the boss.” It is a fundamentally pathetic stance, but one that many bosses take. Yes, there is a level of “the company works this way and your job is X expectation for Y compensation,” but it often goes so much further - when they expect “more work” or “better performance” without giving you the means to do so, or extra pay for extra hours, or without dealing with, say, middle management goons who bark orders without education. At its purest, it is hiring people for vanity’s sake - you’re not hiring because you want to make more money, you’re hiring because you want to do less and own people.

This becomes so much less satisfying without an office. Without an office environment, the dysfunctions of an organization are that much more obvious. Those who are in the office all the time seemed busy, but become so obviously useless without that physical presence that they over-act by sending tons of Slack messages, which makes it seem like they have way too much time on their hands. This goes all the way to the top - if your boss is a lazy, laissez-faire asshole who only barks orders, it’s far more obvious without seeing them in the office, hearing them talk a big game about how they’re constantly in meetings, or, of course, simply seeing them on the phone all the time.

Basketball coach John Wooden once said that “the true test of a man's character is what he does when no one is watching,” and that’s the problem here - corporations have advanced and lionized people based on what they do when everybody’s watching. Remote work mostly destroys the ability to appear busy, other than having a full calendar. Being on lots of calls does not actually have an output if you’re just on them to waffle on about some bullshit, and bosses no longer have the mechanism to appear busy other than doing work.

The annihilation of the office structure in a remote future is so scary because it upends the ability to have a career based totally on being a manager for 20 years. This may seem like a stupid thing to frame as dangerous to the foundation of executive management, but so many people have gone so far in their careers through the nebulousness of “management” that has basically no value in a remote setting.

Failure By Control

The entire value system that hiring has been based on is at risk due to remote work.

Bosses love the idea that they capture your time and part of your soul with work - you are theirs, “full-time.” Their intention was not just to hire you for a task within an organization - it was to trap you and your production in the office, and on some level divorce you from your labor while extracting it, in exchange for the “protection” of full-time work that rarely if ever defends you from layoffs or firings, especially in at-will employment states. That’s why Shayne’s statement is so powerful - it is not about work, it is about ownership.

In reality, a smart business should be grateful that there’s someone that can get shit done in less than 8 hours, it means that they can do more for you in less time, and if they’re doing non-competitive side work, maybe you should pay them more so they don’t go and do that full-time. Or, like, be glad that they’re choosing to use their time to work for you in a way that’s good.

The trickle-down issues of the reasoning behind hiring - the “dance, puppets, dance” mentality of many bosses - is damaged so much by remote work because it relies so much on you being on the boss’ territory. The rise of middle management culture is contrary to the whole idea of “lean management” that companies have lied about believing in - it’s simply a way of the executive giving people the chance to taste and enjoy having power over people’s time and money. Exercising control over people has become such a prevalent form of compensation that many organizations simply have no idea how to advance people’s careers.

Remote work ultimately disproves the notion that anyone can be a manager. Management is tough, managing people is tough, motivating people is tough. It is really difficult to get the best out of someone, to find what they’re good at within an organization and then give them the means and motivation to thrive. It is also equally tough to deal with how some people within an organization have a ceiling - they will never be better than they are, and giving them a managerial title (because they’re not worth more money) is an actively abusive thing to do.

When you take away the dysfunctional executive’s territory (the required time in the office), you remove their ability to “have fun” with the power given to them. It’s less satisfying to call people into your office when you don’t have one. It’s hard to make a manager feel special when they can’t call someone into a conference room for all to see and berate them - it’d be weird to invite people into a Zoom room to watch.

You can’t monopolize someone’s time when you can’t trap them and act as a hall monitor over their every action, and so they want you back in the office. They deep down know you’re not working all 8 hours of the day at your work station, but they know that you know that they could walk behind you at any time and see that you’re doing something else. They don’t want to make the office a place where things actually get done, because that’s not the point to them - the point is that they own you.

And it’s hard to keep control of something that’s out of arm’s reach.