The Remote Debate Shows The Brittle State of Modern Management

After a week in which I set a new, likely difficult-to-match height for views on my newsletters, once with my initial salvo around the remote culture war, and the next on the boss-based brain-melting that’s happening as a result. Through reading the many (many) comments, it’s obvious that many people face exactly the same situations I’ve talked about, but a fairly large cadre of people that take deep, painful offense at the suggestion that middle management isn’t necessary.

I don’t think I’ve necessarily been arguing that management itself isn’t necessary, or that middle management can never work. However, I think an alarming amount of management is handled in a way that I’d frame as either professional theft or hall monitoring. Middle managers have such a grizzly reputation because they’re oftentimes both - they micro-manage and bug you to get stuff done that they then take credit for, while not really creating any output themselves. They are oftentimes measured based on their team’s performance, but not on the individual performance of those under them.

That’s why many people remark about being thrown under the bus by their manager - because the executive chain oftentimes does not hold the manager accountable for their reports’ performance. A good manager theoretically is one that focuses their team on their goals, gives them what they need to succeed and then holds them accountable (and is held accountable) if they don’t. The existence of middle management is (in theory) based on the fact that there are too many distinct functions to be managed by the CEO, and thus work is “managed” by people.

The problem is that (as I previously reflected upon) modern corporations have tied management to career progression without judging leaders based on the success of their team. In a functional management system, if a team is failing the manager is the one who’s ass is on the line, because they are meant to be the quarterback that leads and supports the team, getting them what they need and having their back. However, in the all-too-common dysfunctional management structure, becoming a manager increases your pay without truly increasing your responsibility.

Specifically, “responsibility” is entirely focused on the performance of those under them and taking credit for said performance, as well as on making sure they do as much as humanely possible so that you, as a manager, look good. “Management” becomes a nebulous term that mostly means “organize other people’s work in some fashion that looks good,” versus an actual job - and so many managers become less of a worker and more of a well-paid presentation layer for other people’s stuff.

And it’s because there are many managers who can’t manage, and there are many jobs that don’t require managers at all. In fact, I think that this is a core threat that remote work raises - that many people don’t need managing, and may not even need a boss to do the work they need to do.

And when they don’t need a boss, why are they working for you?

The Manager Apocalypse

The irony of many executives banging on about how we “must return to the office” is that they’re definitely people who’ve talked about how you need to be a “self-starter.” Usually the call for self-starters revolves around the idea that you won’t get much mentorship or guidance, and yet almost always involves some sort of manager who you vaguely report to for some reason. The reason that these dead-eyed management structures exist is that there is an assumption that every business needs managers, and that as the business grows they need lots more managers.

Why? Because I truly do not think many people know what a manager is meant to do, or why they’re meant to have them. A manager is meant to manage, using both their expertise in a given industry and the ability to motivate and support people. This means that they generally have a full plate because there are enough workers to be managed, or there’s enough complexity in the tasks or enough tasks to warrant having someone having to take a macro view. The reason that shitty managers are so common is that they likely see the job as a power trip, but also do not have enough shit to do - management that actually needs to exist generally has enough on their plate that they can’t micro-manage, and indeed won’t do so because they trust the people they’re managing. And when there’s a mistake? They own that mistake, as the buck stops with them.

Remote work has created a situation where being a manager that stomps around and makes everybody do stuff is a lot less hard to justify as a full job. Where you could previously invite someone into your office or look busy on a phone call, the actual sum of the parts of your job as a manager are that bit more obvious when they’re digitized. Outputs are more precise and easy-to-measure when you strip away the assumptions we make based on what we see happening on the periphery, meaning that managers might get the grizzly question of “what exactly do you do all day?”

Managers can be good, and can provide a lot of value. A great manager (and leader!) motivates through being in the trenches and doing work with the team, or at the very least giving thoughtful, strategic counsel that actually makes someone better. Their job is to get things from the higher ups or clients that their team needs to succeed, and their job is to set goals and hold people accountable to them, and celebrate those wins too. Good management finds people’s strengths and finds ways to use those strengths to make everybody win, because managers are meant to be a force multiplier of those under them, not to make sure they’re not taking too many bathroom breaks.

Workplace culture has grown into a monster that creates servitude over loyalty, and that’s why so many companies are terrified to let people stay remote. When people aren’t in an office - a pressurized, boss-controlled area - they are free to do their work without workplace distractions, and are mostly judged based on the work that comes out the other end rather than how people see them work. If they’re better outside of the office, this suggests that at the very least the in-person management isn’t the element that’s making them thrive, and indeed calls into question the need for a manager in general.

In many ways we short-changed managers, too. Companies set people up to be managers without setting firm expectations and key deliverables, because the actual matrix through which we grade management is difficult. Management is often described as an executive function rather than an administrative one, because administrative jobs are considered “beneath” people despite being valuable. We conflate management with leadership, and then misunderstand leadership as control, which gets us back to my previous thoughts around how people see hiring people as a way of exacting control over them.

I also add that a lot of managers also totally ignore the idea of mentorship, and are often promoted based on years of service versus actually being good at the thing they’re managing someone at. Managers should also be trainers in the thing they’re managing, that’s part of the thing. This never happens.

Some managers (and bosses!) are terribly frightened, because it’s much harder to exact the petty levels of control over people that you would in the office, without reducing the need (or effect) of good management. It’s much harder to rule with a culture of fear without having that person in your office, and that person also, working in their own home, is very much aware that they could do this job without you. This may mean that they simply leave the company and start their own thing, or it may mean that middle management types that are used to physically walking into offices, hearing things and then telling the boss are being outmaneuvered.

Remember that fear about control I told you about a few days ago? It’s also laced with a degree of confusion, because they don’t understand why people aren’t just doing what they say.

That’s because none of these people have actually built a culture, and that also means that they haven’t built much in the way of loyalty.

The Loyalty Problem

Dysfunctional management is often exercised through a combination of fear, guilt and derision. My old, awful managers would just tell me it was “the way things were” when they’d report my coverage to the boss, meaning that they would get treated nicely and I would…not. The air of fear that an in-person office creates is partly built on the fact that anyone can see you at any given moment, they can ‘just pop in,’ sure, but they can also see you or hear you do something and thus make assumptions based on that. Someone can assume you’re lazy because you’re leaning back on your chair, or overhear a personal conversation and tell someone else about it. These build into a perception about you at work that oftentimes is wholly disconnected from professional performance, and dysfunctional middle managers perceive these judgments and assumptions as a core part of their job - to observe and report.

Few want to admit it, but lots of bosses love having an office as a place where you are contained and captured, but also judged and evaluated. It isn’t about output, it’s about how you look and present to your company - it’s about what you’re doing “on company time,” both while working and otherwise, which involves “getting on with your colleagues.” Now, yes, a truly noxious person is going to be a problem remote or otherwise, but what I’m getting at more is that in-person office culture usually involves an annoying amount of politics and diplomacy, where people who are “nice” are considered good workers over those who, I don’t know, aren’t as social with their workmates. I am not suggesting that remote work has no political or diplomatic issues, but removing the layer of non-work-related judgment that people use to use to judge people’s actual work is a net good.

The office, the more I write, does not feel like it’s really conducive to actual work. It’s a way of capturing people who are either not focused enough to do tasks or have not been given specific enough tasks to do, sure, but it’s mostly so that you can quickly and easily contain the actions and time of people, because you fundamentally do not trust them.

It’s a way for companies to get around building actual loyalty from the worker, and demanding people come back to the office suggests a fundamental lack of trust and a level of loathing of their work. If they’re performing just as well, and things are working, you are only bringing them back because you want to physically see them, and feel like you have a weird little army that you control. Rather than coming up with a more efficient way of doing things - say, twice-monthly, ultra-focused and organized uses of the office - it’s just that much easier to demand people come in and subtly threaten their employment otherwise.

All of this is just an attempt to obfuscate the things that usually build loyalty. People are loyal to people that are loyal to them, that invest in them, that trust them and empower them to do the work. Executives love to bang on about “company culture,” but too often really mean “ways I can keep you working for me that don’t involve treating you well or giving you money.”

At its core, it’s about how much you value the worker, and labor itself. Hiring people is something you do to make money, and make more money because you have more people. If you consider workers to be a commodity, and labor by extension, you see the worker as “owing” you something for your money rather than someone you hired to complete tasks. Demanding people come into the office based on specious ideas about collaboration just shows that you have an anxiety that you’re not “getting what you’re owed,” when you should, really, know what you’re owed when you’re hiring the person.

The expectation of a worker that works hard has been rooted for a long time in this vague and poisonous idea of gratitude to the boss. You should be grateful for the opportunity to work for them. Remote work makes this far harder to drum into someone’s skull - if they’re not in your office, using your computers and working on “your time,” they can more objectively define whether they’re getting a fair deal too. Because, deep down, these bosses aren’t just hiring you for your work - they’re hiring you for your life. They want to monopolize it, and feel that they own something, because that, to them, is being a boss.

It’s just that bit harder to run a shitty operation remotely. You can’t have people passively and actively inform on each other, you can’t cover up long hours with cheap benefits, you can’t get away from the fact that there is work being done and people have to feel valued for it.

I think that a lot of companies are going to thrive remotely because they’re more laser-focused on doing actual tasks for money. There are always going to be exceptions and edge cases, but the people arguing for a hybrid or complete return to the office are doing so out of a lack of trust in the worker and a lack of appreciation of labor.

You are not entitled to people’s time, or their energy. If you hire someone, you don’t “own” anything. You are hiring them to do a job. If they can do it from home, let them. If you have a reason to have them in the office, make sure they’re compensated for doing so, and make it worth their time.