The levels of being a “cool” boss

In which I out myself as a huge hypocrite in a tepid defense of managers

I bumped into this post by Devon Price (of Laziness Does Not Exist fame around these parts ) a year ago and it still throws me for a loop:

The shots above convey the main point, but it’s worth reading the whole thing.  In response to a call for bosses to be “psychologically ascended,” Price completely rejects the possibility that a boss could ever be ethical—no matter how “cool” you are, holding power over someone else’s livelihood is never just.  

Intellectually, I agree with this opinion.  It’s never a good thing for someone to hold that kind of power over someone else.  But as much as I want to yell ra-ra, I must admit that this post instead makes me uncomfortable. 

This is because despite, um, everything, I’m actually someone’s boss too

More accurately, I’m their middle-management supervisor.   I was excited to take on the role precisely because I mean what I write here.  I fancied myself one of the “cool” ones, an anti-job boss who’d be everything to my team that I wish my bosses were to me. 

And while the fact that I have undue influence over other human’s ability to pay for their survival needs isn’t exactly pleasant, I genuinely believe that my team is better off with someone like me in the role.  I saw it as “ethical” to be here and prevent some neanderthal from tormenting them instead.  When I reached out to Dr. Price, he didn’t agree.  He’s never taken on such a role and would never feel right about it. 

Is the answer really to say fuck all this and refuse to be a boss?  Reader, I’ll admit it:  whether it’s self-interest or lack of imagination, I cannot get myself to fully accept this stance.  At least not as a short-term solution, given the current mess we’re in. 

So instead, while recognizing there’s no way to be fully ethical as a boss, I’ve mapped some guidelines to minimize the harm against those you’re charged with managing, the most “advanced” of which partly come from Dr. Price himself.

Let’s start with the minimally-viable-brain practice that even work-humping bosses should meet:  giving your team clear expectations while eliminating rules around when and where the work gets done.  

As long as our stuff is in on time, my team doesn’t have to tell me when they have doctor’s appointments. Or for that matter, if they go shopping in the middle of the day.  If it looks like they’ll struggle to meet a deadline, they let me know in advance so we can readjust or manage expectations.

Ed Zitron's Where's Your Ed At

(also a boss, seemingly a cool one) points out that this basic communication and planning isn’t a big ask if the “manager” takes management seriously (i.e. sees it as more than delegating and sitting on ass).   But most don’t, which is why they're desperate to get back in the office at rigid hours. 

“These are far from impossible things to do, but require management to actually manage people, which is much easier to do if you just say ‘it’s 9 to 5, you must work these hours, and you must be at your desk waiting for all of them too.’

…

The commonality I’ve found between everyone panicking about Quiet Quitting is that they appear to have not done any real work in quite some time.”

Preach.

You pay your team for solutions to work problems.  Not to be cheerleaders.  

Thomas Bevan and Craig Burgess advise that “business owners should accept that their employees will never care as much as them,” and damn if that’s not the best management advice I’ve ever heard.  We make people do this “of course, even if I wasn’t paid I’d still spend my time building marketing funnels” song and dance when it would be much healthier to acknowledge that no one in their right mind would do most jobs if it wasn’t for the money.  

Functional-brained managers don’t expect (much less demand) workers to care about the job.  Workers will do the job anyway.  No need to add the exhausting, pointless indignity of performative passion.  

You know what else you’re not paying your team for?  To validate you, or to fill the void in your soul that you’re misguidedly trying to fill through your job. 

I was in a management class a few months back and had a classmate who sincerely cares for his team.  One day, he was down in the dumps because one of his employees quit.  While we tried to reassure him, he lamented that just a few days prior, he’d even given her a card thanking her for her contributions.  “And she answers by leaving for some other job she doesn’t know, just because it pays a little more?”  

I love you bruh, but don’t be a weirdo.  You’re not this person’s boyfriend or dad or whatever. OBVIOUSLY, she should take the money over a stranger’s (yes, that’s what you are) warmed-over gratitude. 

All this gets at whether emotional nourishment (ie. building team camaraderie, culture, friendship) is a manager’s responsibility.  Five years ago, I would have screamed “hell yes” from the rooftops.  Not anymore.

Should you ensure an environment of dignity, respect, and cordiality–one where your team members might strike up friendships if they feel moved to?  Of course.  Should you offer support and accommodation if people share personal issues that are making their work difficult?  Definitely.  

But presenting the workplace as a space for people to get their sense of community is an insidious trick that makes them dependent on their employer for needs that should be met through friends and family.   Your team should have enough time outside of work that they can build a separate community that won’t cast them out as soon as the quarterly reports lag.  

Things get expanded-brain when you cease to see your purpose as stretching your direct reports for the company’s success.  No, you’re here to stretch the company for your direct reports.

If there’s any growth to be captured, you’re clear that it’s better converted into leisure and paychecks for your team instead of growing the company’s financials.  Assuming you’re already ensuring your team’s physical safety and dignity, you’re prioritizing maximizing their pay above all else.  Not sure they’re quite ready for a promotion and a raise?  You do it anyway—that’s the main reason you’re here!  

Of course, you need to provide some value to the company too, and you need to maintain a minimum standard of performance from your team.  But only enough to keep things running, and never at the cost of your team’s sanity.  

If you trust your team to not narc, you might even tell them directly that this is your approach.  That way, no one feels the need to hassle others with proactivity or overachievement. 

I’m happy to report that I practice everything we’ve outlined so far.  I’m my team’s ally above all, with the company merely an annoying afterthought in my mind. However, I haven’t even begun to sniff the galaxy-brain level, where you’re taking an active role against your company and their owners, brazenly sabotaging them at every step.  

This chaotic good version of private equity investment—you’re wrecking a company, but you’re doing it to benefit its workers instead of some vampires in suits—is the only approach that Dr. Price feels gives bosses a chance to be “ethical.” He was even gracious enough to give me a clear definition of a theoretically ethical manager:

“One who betrays the company and the concept of what a manager typically is supposed to be, at all times.”

As an example of what this could look like, he cited a friend who took on a management role and used it to:

• Openly complain about company policies, pay, and hours

• Validate all employee concerns and express their grievances

• Refuse to take on extra work if it caused your team additional stress

• Agitate for a union

I would add an additional bullet which may be implied anyway:  the commitment to never, ever fire anyone, no matter how negligent they’re acting.  Even if they’re making life more difficult for everyone else. If this means you eventually get fired with them, so be it.

(It’s my understanding that this commitment is, to a less extreme extent, a practice in Japan due to both societal “lifetime employment” customs and very strict laws around when you can fire someone.  It sounds beautiful, even in its modern shove-you-in-the-closet form.)

I personally have NOT made any of these commitments.  I’ll admit it: I’m scared they’ll result in an amount of attention (whether due to agitation or underperformance) that’s unsurmountable, will get us all fired, and will disrupt my ability to feed myself.  

Which brings me to a worse confession: I don’t have to worry about this with the people who report to me.  They’re “amazing” workers in the sense that they have a “self-starting work ethic” (in BQE terms, they’ve internalized self-coercion).  This makes me sad, but part of me is thankful because it makes my day-to-day easier.  Not to mention it staves off any moral conundrums around how much to protect someone who’s not doing the basics.  

The bosses suffer with us

I consider my bosses to be good people.  They’re self-aware and kind, and I’m thankful I work under them instead of some asshole who’ll mash me into pulp with gusto.

But mash me they certainly do, and God knows they can do it like the worst of them.  One, in a moment of weakness, admitted that she feels like her job is to stretch people to the brink, like a torturer.  When I reciprocated this vulnerability by admitting I was thinking about quitting, her eyes welled up and she told me she wished she could quit too. 

Witnessing her despair made me face that, when I started writing about this stuff, I got off on the notion that I was more in-the-know than people like her.  I pictured her class as craven dopes who chugged the Kool-Aid while I belonged to the enlightened crop. 

But the truth is that way more people than I thought—not just my boss—are aware that they’re trapped in a dehumanizing system, consciously suffering along with us. Paul Millerd presents a 2019 Gallup survey as evidence:  97% of Americans define success as “following your interests” instead of “having a high-profile career,” but only 8% think that other people define success in the same way.  Most people work-humping on LinkedIn don’t mean it.  They’re just performing what they think others want to see, under penalty of starvation. 

It’s easy and cheap (and fun!) to caricature bosses as villains.  And to some extent, we deserve it.  But what’s legitimately uncomfortable in Dr. Price’s truth-bomb is that it tempts us to blanket-demonize about a fifth of working people in America.   To be clear, I don’t think Dr. Price is going for that.  But it has also been my experience that the antiwork internet is quick to a fight (necessary if you’re fighting against decades of groupthink) and slow to digest nuance. 

I’m not saying that we should ignore bosses’ role in perpetuating an unfair form of power.  I just want to be equally mindful of the balance between having these conversations and lashing out at a large swath of our population who won’t feel able to disentangle from these roles anytime soon.  Mindful that we’re suffering together, let’s follow the late Michael Brooks’ timeless advice to “be ruthless with systems, and kind to people.”

…or, if you MUST take out the managers when the revolution comes, remember I was that cool boss who wrote scorching hot blogs about hating jobs, k?  At least give me a running head start.