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The Pointless Executive
Editor’s note: A previous version went out via email where the edits weren’t finished. Sorry about that! I’m kinda sick today!
I sometimes wonder if I’m stupid.
This isn’t me being self-effacing, or fishing for praise. I just often get this overwhelming sense that I am not the smartest person, yet I have a functioning company and do not seem to have run into many of the roadblocks that seem to hit many similar (or different!) companies.
Or perhaps I have never really bathed in the filthy swill of management theory. I’ve read a few books on management, and mostly found them to be weird history lessons about how Bell Telecom was set up, with some sort of object lesson buried within.
Which is why I find pieces about “how to lead a remote workforce” so bizarre. I get confused by the assumption that managers and executives often describe: that if people are not complaining, they are on board with what’s happening in the workplace:
I’ll confess: I’ve always loved working in the office. The early days of RippleMatch—the startup I cofounded and grew to 100 employees over the past five years—are defined in my memory by late nights in our single-room, glass-walled WeWork office. Camaraderie forged in the daily struggle to launch a business, working in close proximity with incredible people. Take-out dinners, playing music, and team happy hours.
If I had to guess, I’d imagine that the other people in the room with him that weren’t founder-level were likely not quite as excited to stay in an office. I also - and this is my personal belief - think it’s sociopathic to romanticize working late in general, and running your company based on your own personal belief system, while inevitable, is also an extremely easy way to hurt people in silence.
Late nights in a single room sound truly awful, and if I were working for someone and they said that to me directly, I would ask them why they didn’t miss their family or animals or other things they do for fun.
One Twitter user pointed out the worst part of this story:
The problem is that there are many people - executives in particular - who see nobility and drama in struggle, toil, and work. They see themselves as brave soldiers fighting across the trenches of capitalism, earning their reputation not simply through business goals and outcomes, but through their own visible and dramatic success and failures. In this article’s case, the writer doesn’t see late nights spent working at the company as a negative - he sees them as steps in the hero’s journey, they are the very things that “make” someone a success. But doing actual work? Rarely.
Accenture and Hertz’s $32 million website that never went live is a comedic example of why this is a problem - the people signing on both sides had no real idea what the hell it was they were doing, and Accenture, who have huge management issues as it is, convinced Hertz to regularly sign checks for projects that are half or totally incomplete. If a single person at the managerial level actually knew what went into developing a project like this, they’d know - and have built - actual milestones to hit and have an idea of what it is they’re doing.
Tyler Best, the former CIO of Hertz who signed off on and was the steward of the entire deal, was referred to as “[providing] his team with accountability and continual feedback” by CIO Magazine back in January of this year, years after he was ousted from Hertz.
And that’s the problem with the lionization of leadership - so often this leadership does very little to actually lead, but regularly receives the credit (and wealth) associated with doing so. But when they’re actually tasked with leadership - getting a company through a pandemic, choosing to close offices and empowering workers to work remotely - they choose what will make them (and their shareholders) happy versus what will make their workers happy and their business stronger.
These public corporate dramatics are important to consider in the pushback against remote work, even among those that have eventually accepted it. It’s not just about enjoying watching your workers skitter around and controlling their lives, but a kind of wrongheaded personal branding exercise where you’re creating a certain mise en scène for the movie of your professional life, something you can point at and talk about as proof that you “earned” the eventual outcome.
Your late nights are the record that shows that when (if?) you reach a big pay day, you’ve earned it - late nights, while not necessarily indicative of actual work, are a dramatized version of what most people consider to mean “working hard.”
Part of this is the quasi-religious approach that some capitalists have toward work - the shared idea that there is nobility and moral “good” in work, and, indeed, that if you’re not showing everyone how hard you’re working, they may not know you’re a good person. It has to be visible to others, because this is absolutely a performance.
While these folks are always about “succeeding,” “success” is often not just about the business doing well, but about the CEO in question trying to feel as if they are the main reason that the company is doing well. This, of course, becomes significantly less likely the larger the company gets, while the likelihood that the executive in question will make a lot of money off of the back of other people increases.
Remote work vastly dilutes a manager’s ability to frame other people’s struggles as their own - there is no pantomime of late nights spent shoulder-to-shoulder with teammates that can be used to prove that you were “in the room” and “making things happen.” Executives that thrive off of feeling important and powerful can’t intimidate people into hanging out with them “for the sake of the company,” and they have few ways of proving their value to the company other than…doing work.
I’ve written a lot (perhaps too much!) about this being a core reason that managers hate remote work, but I really do think it informs a lot of executive reactions to working from home. As a company grows, it’s inevitable that executives are less connected to the core work product, and the executive’s importance is gauged less on their actual contribution and more in the general success of the business. As a result, the executive isn’t scared about simply losing their office, but losing offices in general - no offices means nowhere to go, nobody to meet, no way to physically show how busy they are, and prove whatever abstracted value they have to everybody in the company (and themselves).
This is why you see so many higher-ups banging on about how everybody needs to “come back to work.” They aren’t just looking to see everybody - they want everybody to see them, and remember who’s boss. They can say they’re “collaborating with their team,” even when they only really speak to a few people in the C-suite or on the VP level. They can talk about “being connected with the heart of the business” by popping in once or twice a week, taking ownership of the entire operation without necessarily having to contribute to it.
I speak in generalities, and while there are executives that work, and are important, I find it hard to believe that those calling for a return to the office are contributing that much. And that’s partly because the nature of being an executive has been abstracted away from actual work - the modern CEO is a caretaker, a figurehead and a spokesperson. When things go badly, the CEO has to make “hard decisions” that usually involve firing other people, and when things go well, the CEO receives accolades.
And yet we as a society credit them for work that they in many cases have never done - or haven’t done in so long that they would be hard-pressed to describe the actual work product that enriches them.
Sidenote: This is why I think there should be a rule that says that any CEO has to participate in a minimum of five days of the lowest level job at their company a year. SaaStr’s Jason Lemkin recommends everybody in SaaS ideally should do a 2+ hour stint in customer support a quarter, and I think that should extend to every single company. If the CEO of Kellogg’s was forced to do the work of the striking employees he’s replacing, I severely doubt he’d be treating them so poorly - and at the very least, it would be very funny watching a white collar guy have to run machinery and do manual labor.
This is also why it’s so stupid to ask bosses about working from home - they, quite honestly, may not actually be doing any of the work. Though it’s unlikely you’d get an honest answer, the real question to ask any boss who’s against working from home is “what do you do all day?” They’ll get mad, they’ll claim they’re in “meetings,” but they’ll very rarely give a direct, specific answer - because the truth may be closer to the idea that these people work the same amount as most people - which is actually only a few hours a day, at max.
All of the problems we’ve seen pop up in the last two-ish years about remote work, about employee loyalty, and about do-nothing managers come back to a very simple problem: the higher up the chain you go, the further you move from actual work. Managing people can feel like work, but if you’re not doing the work of the people you’re managing, you lack the insight and empathy to manage those people properly. If you have little or no practical, recent experience with the work you’re managing or that you’re the executive of, your perception is flawed and you have no real hand in the output you’re credited for.