Bad bosses: The circles of management hell

Bad Bosses

I’ve got a lot of experience with bad bosses (definitely more with that type than with good bosses, unfortunately); I’ve got so much experience with bad bosses, honestly, that I once wrote a post explicitly detailing the 12 worst types of managers you’ll likely have someday. This shouldn’t necessarily surprise anyone, per se — not that I wrote a post about bad bosses (because I’m an inherently bitter person), but the sheer fact that so many different types of bad bosses exist. By some measures, 82 percent of all managers are, in fact, bad at their jobs.

When I was growing up, my mom always used the expression “seventh circle of hell.” As a result of this and never actually reading Dante, I always assumed there only were seven circles of hell. Just did some Googling and apparently there are nine. I know nothing.

Last night I was sitting at a bar eating a hamburger, because this is what one does at 35 with no children when their wife is sick (don’t worry, I got her food to go) and for some reason on my phone, I outlined a post about ‘the seven circles of management hell.’ Here it is now: a look at bad bosses, in all their (in)glory.

Bad Bosses Circle 1: Actual leaders

Ha-ha! Tricked you. This isn’t actually a section on bad bosses. This is a section on what bad bosses should aspire to. At this point in your work life, you’ve maybe seen this graphic once or twice:

Leader vs. Boss

My man Croft Edwards — done some writing work with him — has as good a classification as any here. He basically says:

  • Managers are people given organizational authority; it was essentially handed, or granted, to them.
  • Leaders aren’t necessarily organizationally-vetted, but they’re still people who take care of you and make you aspire to something greater.

There is still a lot of confusion among corporate types about this whole “leader vs. manager” split. They are absolutely, positively, 100 percent not the same thing. Most managers are effective at some things (hence them becoming managers), but generally bad bosses. Most leaders are effective at many things, including being a good boss. So this is Circle 1. This is the good stuff.

Bad Bosses Circle 2: Managers

The next couple of circles, we’re going to get down into sub-types of managers and truly bad bosses. For now, let’s roll with a standard manager. Typically a manager is very good at process — this usually helps you get the promotions needed to become a manager — and has good relationships with ‘the power core’ of an organization (politics also helps you get promoted at most jobs). Process and politics are everything to many organizations, so we can’t necessarily criticize a standard manager: they played the game and did OK with it.

They might be good with people, but many are not — because we promote, again, often based on politics and process. We don’t think about things like “Can this person communicate?” or “Will this person be summarily loathed by everyone who must do projects for him/her?” There’s no standard balance sheet ROI on those things, so we avoid them and rush to our 2:30pm stand-up. So a standard manager isn’t necessarily a member of the bad bosses club, but it’s still one degree shy of leaders.

Bad Bosses Circle 3: Target-hitters

Here’s where the world of bad bosses gets fun. A “target-hitter” is slightly below a manager. This is how I’d describe these guys and gals: they’re probably managers themselves, yes. They probably have a degree of organizational authority or formal power, but they have no clue about any organizational priority. Here’s what they do know, however: they want to rise up a little bit themselves, OK? They want more scratch and formal power — and they realize the easiest way to do that is identifying what the most senior-ranking people claim is important, then going out and hitting those targets.


If you’ve ever worked at an office that has more than 10 people in it, you know that “what senior-level people deem important” (read: things related to money) often aren’t aligned with day-to-day priorities (read: the shit you gotta get off your plate and onto someone else’s). This is where most of work falls apart: there is, essentially, no alignment between strategy and execution. But a target-hitter still figures out what the C-Suite cares about and goes and gets it done. This person eventually gets paid more, but is usually miserable to work with and a complete sycophant to the top dogs.

Bad Bosses Circle 4: Target-chasers

This is where bad bosses 101 begins. A target-chaser is ostensibly a would-be target-hitter, but because of Peter Principle and a host of other factors, he/she can’t actually “hit” the targets — just chase them around until someone reassigns them to a different, less-important project. Imagine if a senior person comes to a target-hitter and a target-chaser and says, “I need that report on Q2 metrics by Thursday.”

A target-hitter will get that report done, probably stepping on 3-4 people’s necks in the process and verbally demeaning 4-5 people under them. A target-chaser will start the report, get distracted by e-mails, take a 2-hour lunch, like a few of their sister’s pictures on Facebook, berate someone about process, create a few meeting invites, line-edit a couple of tweets, come back to the report, leave for the day, answer a few e-mails at 10pm to show the bosses how committed they are to the tasks at hand, come in at 9:54am, gossip, write some e-mails, etc. Soon it’s Thursday, OK? The target-hitter delivered the report and the senior guy is happy. The target-chaser is on Pinterest looking at soap options. Target-chasers don’t get promoted, but they don’t get fired either. They clog up the ranks of bad bosses and middle management and generally make everyone’s life a living hell when they manage ’em.

Bad Bosses Circle 5: Sycophants

This is where you start coming to work and contemplating plunging your head into the toilet bowl around 10:41am each day. Sycophants are an interesting variety of target-hitters, but without any managerial or operational skill. Here’s the deal: a sycophant is usually close with one or two people in the power vortex, and has been around a couple of years (maybe 5-10). Because they have this senior management ‘rabbi’ (someone who protects them), and they’re semi-smart enough to realize that they would have been fired 3 years ago if not for that connection, they’re total sycophants for that person. The senior manager loves this: ego-stroking but also it’s someone he/she can throw no-context projects at all the time. “I love me some Bobby, he gets it done!” Secretly everyone knows Bobby doesn’t get shit done and Bobby is probably better suited to be sucking his thumb under his desk every day, but again … workplaces are all about relationships, and relationships drive who does what (and who can avoid what). So essentially, a sycophant is a politically-protected target-chaser — it’s a worse degree of bad bosses because no one can really call a sycophant on their shit. You don’t want to alienate that big dog rabbi.

Bad Bosses Circle 6: Drones

This is rank-and-file worker bees who maybe have a few direct reports. They do the most middling tasks possible, no one really gives much of a shit about them, and the CEO will pass one of ’em named “Ben” and bellow “Good day, Tom!” That will happen for 7-10 years with no one on either side making any effort to correct the process. Drones are a bit dangerous to the bottom line, though: they come in around $60,000 or so and they take that 1-2-3 percent raise every year, a couple of bonuses, and a few direct reports. In 10 years they’re still there costing you about $80,000 and driving turnover rate sky-high so you need to keep hiring “social media specialists” by the metric fuck ton. Drones = among the costliest of the bad bosses.

Bad Bosses Circle 7: Whom?

This is about as low as it gets — it’s basically lower than drones. This’ll be some dude named Richard and absolutely no one has a goddamn clue what he does all day, including his boss, his direct reports, and every secretary in the place (who are essentially paid to know who does what and when). Richard will take long lunches, make a few laps around the office each day, show up aimlessly at a few meetings (“Who invited this fuck?”), get coffee 3 or 4 times, and whenever one of his direct reports asks about something directly, he’ll nervously grumble and then yelp about how busy he is. At Richard’s retirement party, the CEO will call him “Thomas” 114 times. Not even Richard’s wife will make the correction. The terrifying thing is, there are guys like Richard in almost every company in the world — they make money, they’re tasked with supervising the workloads of others, etc. and no one knows exactly what they do or where they came from. It’s one of the most amazing things to watch in its natural habitat; a place can preach its ‘productivity focus’ and ‘organizational health’ and ‘success orientation,’ and there’s Richard, lurking in the corner of a 10:30am stand-up as half the room wonders if he showered this AM. Work is amazing. Bad bosses are amazing. I hope you enjoyed this ride.

Any other types you’d add?

Ted Bauer

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