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Case Studies | The Toxicity of the Shitty

Updated: May 25

Welcome to Case Studies, an article where we take a look at a specific institution, methodology, or entity and attempt to pick it apart until we've beaten the damn horse into soup

A note from Astutely Obtuse:

On this site, we really try to anonymize things as much as possible. To the extent that we'll spin others' stories in such a way as to make them appear to be our own experiences. So frequently, when we portray things as being first-hand experience, it's actually a melange of several people's first-hand experiences.

Today, we break from that. We are going to look at a case that includes only a single person's first-hand experience. We won't provide any specifics behind who supplied the case, those involved, locations, names, or anything else along those lines. We are not interested in slandering anyone or any business, nor do we wish for anyone to brigade against any company or individual.

We decided to start sharing these stories because there is so much that can be learned from looking at a specific case that has problems, where the company was in a noticeable decline.

When I left a previous job I began to work as an independent consultant. Dude... let me tell you... business people gossip. We're talking Saturday afternoon at the salon levels of gossip... no... worse than Saturday afternoons at the salon.

From Mean Girls.  A women dressed in pink PJs holding a chihuahua says "what's the hot gossip? Tell me everything."
I can guarantee that when Elon and Rogan get together, they do this, dress, chihuahua, and all.

Over the next months, I heard stories of failed attempts by the CEO to acquire funds to keep the company afloat until their most profitable season, potentially filling for chapter 11, investigations by the SEC, a number of class action lawsuits, layoffs that could affect in upwards of 25% of the workforce, a push by the shareholders to pass a vote of no-confidence, and a desire to completely replace the entire board.

Hearing all of this was surprising.

I should point out, I have no clue how true any of it is. Like most gossip, it could be 100% true, it could be an outright lie, or it could be a modicum of truth--wrapped in speculation and exaggeration.

Why this was so surprising was that it was a highly respected company when I started; it was considered one of the best places to work in the city. Now, however, it's a sad tale, a bit of a joke. It's the subject of when are they going to go belly-up betting pools.

How did they get here?

Idiots the Whole Way Down

I don't think it ever comes as a surprise to hear that a company failure is related to poor management or mismanagement. Our case study, however, takes mismanagement to an Olympic competition level of mismanagement. Failing upwards is an art form there, where they weave nepotism and favoritism into the shittiest tapestry you've ever witnessed.

A pink and green thing saying Gaslight, Gatekeep, Girlboss.  It's fucking weird man
"And what are your managerial strategies?

The thing to realize is that the mismanagement didn't come on suddenly. From a ground-level perspective, it was a growing problem that had been obvious for a very long time.

Let's take a look at this from the point of view of the project team. First, the level of disorganization. There are a lot of warning signs you can see from the PMO related to the mismanagement higher up, and frequently, it's related to disorganization.

Is there a belief by those in the business that once work is requested they no longer need to have any input in the project? Is there a refusal of management to take ownership of projects and processes? Is there an underlying belief that the PMO is magic? Do you have a single VP acting like a fucking spoiled ass toddler? Is that fucking toddler being enabled by the CEO? Are the people being promoted incapable of saying no?

While having dinner with some friends, I explained these warning signs that things are not healthy on an organizational level, and the response was "that describes, like, 75% of all businesses." To that I say, does that not fucking concern you?!

All these things combine to uncover the small cracks. You see, in order for a business to function, you need order. Order doesn't necessarily automatically suggest that there is an organization to how the business functions, but it's a central fixture that should be dusted off once in a while. Disorganization is a weakening of the order you need to be successful.

In our case study, the disorganization produced chaos. The idiots defended the chaos. It was "how it's always been done." I read it as "why would we get better when we can just make everyone miserable?"

What was especially annoying was the insistence that they couldn't do better because no one had enough experience in larger companies to do better.

Let me tell you, this was infuriatingly bullshit. Some of the best and brightest went unacknowledged, or worse vilified for being knowledgeable and/or talented. Everyone complained, but the smart ones offered potential solutions, which were ignored, or said to be "hurting morale."

So why were these team members ignored?

They Only Promote Superfans, Sycophants, and Lovers of the Status Quo

We've all worked with them. The people who have an unwavering adoration for leadership. Those who couldn't even fucking imagine questioning decision-makers.

The reason that concerns, suggestions, and frustrations get shot down is that acknowledging them means questioning leadership. So, any idea dies as soon as it's spoken. There is no upward communication, just a dictatorial adherence to what is commanded from on high.

These promoted individuals are typically terrible at their jobs, but sing the praises of management, and therefore get promoted. At this particular organization, it took the form of the most hated PM failing in role after role until she was made a director.

If You Ignore the Problem Long Enough, It Goes Away

By "it," we mean your best and brightest.

There was a weird dynamic that occurred. Those who challenged the methods, and called out the director were deemed problems. Not just when they were screaming into the void, but at the sign of any descent. They were just labeled a problem.

And when the frustration hit a boiling point, and they blew up at someone, everyone acted surprised, that this was the first time they had heard about people being upset or frustrated by something, they just must be a problematic team member.

But here is how the frustration actually progressed

  • Hey, there's this thing that's causing some issues. If we did χ I think it would resolve some of those things.

    • You're not being a team player

  • This is a serious issue. It's frustrating people, and really causing problems, I suggested we do χ before, but didn't get anywhere, can we please just try it?

    • That's not how we do things, we've never done it that way, no one else seems to have a problem

  • We do this thing, and it really fucking pisses everyone off. Other organizations do χ, Why the fuck don't we even try to do χ?

    • Ohhh... so much hostility. Why didn't you suggest this before? We're not going to do it now because you're being a total jerk-store. If you were nicer, we might have considered it.

Angry outbursts don't come out of nowhere. They are the product of repeat denials to be heard. At some point, yelling is the only way to get your voice heard. It returns us to the problem of an undue adoration of those in charge. The smart ones are ignored because they don't want to challenge those above them, which is why these assholes get promoted.

While we are on the topic of bad leaders...

Lead Positions are FIlled With Grifters, Imaginary Martyrs, Egotistical Assholes, and People Unwilling to Delegate Because It Requires Relinquishing Authority

Long section titles aside...

"Waaaaaa.... why do I have to do everything myself. Nothing happens without me, I am the greatest thing to happen to the company, but I'm so busy taking care of everything. Waaaaaaa...." [Proceeds to forcibly insert themselves everywhere, and is so shitty that they create new problems which forces people to have to rely on them more] "Why am I the only knowledgeable one here?"

Sound familiar?

In this specific case study, this mother fucker would force himself into every meeting, complain that he was there, give very little input, complain that no one understood what he was talking about, frustratedly claim he would do it himself, complain that he was doing it himself, set up a meeting to complain that he can't do his regular job because he's having to code shit, then complain that there was a meeting where he had to lose time coding to say that he doesn't have time to do his job because he's coding.

A bottle of Barossa Grenache, called Bitch.  On the back of the bottle is Bitch written over and over again.
That's right, I'm calling you a bitch

Within a team, these martyrs with a persecution complex amplify the problems within the organization. In this case, he amplified the chaos.

These fuckers are grifters, plain and simple. I guarantee it. When you really look at it, it is a thinly veiled attempt to call attention to themselves in a controlled way. It is verbal misdirection aimed at showing the good they do by exposing everyone else as bad. The grift begins to fall apart as soon as you ask them to do something specific to fix some of the things they love to complain about.

  • You wanna help? Great, create a data contract for this new system.

  • You are tired of having to join meetings to tell people how this one specific piece of tech works? Document it so we can refer to it without bothering you.

  • Tired of always having people come to you for your input? How about you train another dev to take over some of the responsibilities of an SME?

These suggestions will always be met with a sob story. They don't have time, they can't train someone because they are forced to do everything on their own, etc.

What bothers me the most about these assholes, is that they treat everyone around them like shit. They look down on them like they are dumb and just another write-off. Then they'll say things like "I just want you to be better," when you call them out for their shitty behavior.

Part of the grift is to also convince everyone around them (including those who they treat like shit) that they are the absolute greatest thing to happen. The grift doesn't work if everyone around them doesn't believe it, so they force themselves to be central to everything so they can get everyone to buy into it.

Why does it work?

Those Who Weren't Toxic Were Enablers

With the two types of toxic individuals I discussed, it might be easy to think that what I'm discussing was the end result of years of a slow eroding of organizational culture. While the extreme take on it is certainly the end problem, the problem was always there. It just wasn't as pronounced. How were these jag-offs able to reach the levels they were without being called out?


In the early days, there were a few people who went to leadership with concerns over some individuals, and what they saw as burgeoning toxic behavior. It went largely ignored because there was always an excuse to be made. They are new to the position, they've been around longer than anyone, some shit about their personal life, they are best friends with the VP so don't say anything, etc.

The root of the problem facing us wasn't that there were a couple of toxic pieces of shit on the team, it was that those who could have corrected it before it became a problem shuffled their fucking feet.

To put things into perspective, at a time when things were still great, we had extremely knowledgeable people who blew everyone out of the fucking water when it came to talent. These people would request to change teams or flat-out quit because they couldn't stand working with these toxic individuals. And this was in the best of times!

As noted before, the angry outbursts don't come out of nowhere. The complaints went unchecked, and by doing nothing to stop the toxicity, those in charge encouraged it.

Not Mourning the Loss of Good Employees

In the early days, when someone who was good at what they did quit, it was felt across the entire team. Leadership would have a going away party, they would be told how much they will be missed, and they did what they could to retain them. As things started to fall apart, those things slowly went away. In the end, losing good employees was seen as a good thing. In a meeting with heads of IT, the VP actually suggested that losing a highly respected member of the team, that was the best at what he did and had a hugely positive impact on the project team and organization as a whole was "a good thing," and that "maybe we can get things done now." You see, this guy didn't do anything half-assed, and apparently, it pissed off those in charge.

There were developers with incredible institutional knowledge and tacit knowledge that can never be recovered. They left, and their leaving was treated as just another day. Again, anyone who dared to express displeasure was a problem. How would their leaving not be a good thing?

Not Celebrating the Talents of Underappreciated Employees

To be clear, this is not talking about giving a public shout-out for hard work, it's about not recognizing the things that make an employee great. It's about underutilizing these employees in a meaningful way, and not making it known that you appreciate those talents.

In my time at the company, I worked with a lot of amazing people. At some point, I noticed that many of our best were underappreciated, and what's more, they weren't being acknowledged for the unique talents that they brought to their roles. A PM with a mind like a steel fucking trap, who could tell you everything and anything you need to know about her projects. A project lead whose snarky yet gentle tone could calm any dispute, who was respected by everyone she interacted with (almost everyone). A developer with a keen eye for the user and customer experience, who naturally concerned himself with a more holistic approach to development. These were people that were "thanked" for their work, but never really appreciated for what they brought to the company, and it's really fucking sad.

Getting Real

When I look back, and I see all the things that led me to quit, and how bad things go in the course of a few short months, I start to realize that the signs were there from the beginning and the fact that at every turn we were told that "it's always been this way" it was probably around for a long time before I started.

When the company announced it would be going public, I warned co-workers that it would change the culture around the office. This was largely ignored. You see, much like the grifter/martyr amplifies the problems within a team, being publically traded amplifies problems within leadership, in this case, that leadership was trying to run a 30+-year-old company like a fucking startup.

We selected this case study because we see that there is a cautionary tale to be told. The problems that affected the company are not unique. It happens all the time. This is meant as a cautionary tale for those in situations where you see this exact sort of thing occurring. Trying to find a job sucks as it is, trying to find a job where the rumor is that your previous job is going out of business, is going to make matters much more difficult.

The important thing to learn is if you see these things beginning to manifest or become more commonplace, you should look at leaving. The most important thing is to protect yourself and your mental health. For me, it was draining. I really liked working there when I started, but in the end, I was a villain, I was hated, I took the blame for everything that was going wrong, I was told that when I left things would be better, I was told that my refusal to blindly support the director was making her cry (in the hopes that I would fall in line), and worst of all, my work ethic was being attacked on a daily basis.

I really believed that by speaking up and offering suggestions I could help make the process better. I would support others on the team that offered up suggestions to make things better, even if I didn't necessarily agree or understand their take. I truly wanted people to enjoy coming to work again, and not just be miserable all day long, but I was the problem.

When I finally got out, I was in a very dark place. I was defeated. I felt like a failure. I was leaving good people behind to suffer without anyone to speak up for them, and worst of all, my hard work never amounted to anything, so what was the point, right?

What brought me out of the shithole that my mind had wiggled its way into was being told by two of the people who hated me the most that I was "one of the best people they had ever worked with."

When bouncing ideas off of Mike for the wrap-up of this article, he offered this insight passed to him from his grandfather: in bad situations, you must always understand that there are two competing ideas you need to balance. You can stay quiet and be miserable, or you can speak out and become a villain and still be miserable. You can be one of the good ones speak up for yourself, or you can be one of the great ones speak up for others. Wisdom is knowing when these are no longer in balance, and that the battle is lost.

It's admirable to try and change things for the better, but don't do it to the point that you are hurting yourself. Do what you can to protect and shelter co-workers, but know when the battle is lost.

Listen to the rumors, hear what people are saying about what it's like to work there, and really reflect on the toxic traits of those in authority. Then ask yourself, is this worth it?


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