“That One Night” – The Hunted (from the US version of “The Office) (2008)

To identify the most cringe-worthy moment of one of the most crigne-worthy episodes of the US version “The Office” is, I realize, a bold task.  But this song, written for Michael Scott’s girlfriend / ex-boss Jan Levinson by her former assistant, is beyond creepy … and funny.   We first see Levinson’s assistant Hunter on the episode where Jan is getting fired (“The Job”), and as she hugs Hunter, tells him “”Good luck with your band,” adding “Don’t let them change you.”  Well, this is the payback … a song dedicated to the night where Jan allegedly made Hunter a man.  The fact that Jan plays this song wistfully in front of her current boyfriend (Michael) while trying to dance with another man is an extremely queasy and funny moment.   The fact that Hunter named his band “The Hunted” speaks volumes.

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“Handbags and Gladrags” – Rod Stewart

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Recognize this one? A cover of this was the theme of the UK version of the seminal comedy TV show “The Office.” However, the song was originally written by Manfred Mann’s Mike D’Abo. This version by Rod Stewart from his first solo album in 1969 (called “An Old Raincoat Won’t Ever Let You Down” in the UK, but was released as “The Rod Stewart Album” in America). Makes you almost forget about “Tonight’s the Night” or “D’Ya Think I’m Sexy?”

A certain kind of horrible boss … as seen in the BBC version of “The Office”

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The original BBC version of “The Office,” with Ricky Gervais, is one of the best TV series ever created.  While the American version with Steve Carrell is very good, it gingerly avoids the darkness that makes the British version arguably funnier … and much more painful to watch.  Carrell’s Michael Scott may be a pathetic, delusional human being, but his character is nowhere near as pathetic or delusional as Gervais’s David Brent.  And unlike Scott, Brent pays dearly for his delusions and the BBC version doesn’t let you off with a laugh at Brent’s expense.

I could talk in detail about how great the BBC version is, but I won’t.  Mainly because I have nothing to add to the many brilliant things already written about it.   However, the reason I’m talking about it now is how “The Office” brings to light a certain kind of horrible boss that we all know about, but until “The Office” (BBC version) so clearly articulated it, was hard to define.  When people think of horrible bosses, most people would identify the obvious tropes: the yellers/screamers, the micromanagers, the sexual harrassers, the bigots, the homophobes, the religious fanatics, the anti-religious bigots, the smarmy passive-aggressive types (best exemplified by Gary Cole’s Lumbergh character from “Office Space”), etc.  Yes, all of these types sadly still exist and admittedly, are probably worse than the type of boss that Brent represents.

Yet, Brent epitomizes what I call the “disengaged boss.”  A “disengaged boss” is not necessarily a bad person (though sometimes they are).  They are bosses who tend to be either severely distracted (either by drama outside of work or other activities) and/or have no interest at all in actually leading.  They may have an interest in being “the boss” because the job pays more, the job holds more prestige, and it may lead to something that pays even better and has more prestige.   But they care little about the people below them.  By not being aware of what their employees are doing, they’re unaware of situations that could explode into crises, they don’t performance manage employees that stray – leading to resentment from those that don’t, and they have no idea of what the people below them actually contribute and what their strengths are.   When the disengaged boss is called out on it (usually by their superiors), they overcompensate by either micromanaging some situation that’s within their control (usually something insignificant), or they completely misread the situation (because they barely know what’s going on) and make things significantly worse.

Sometimes, these people bill themselves as a “fun boss,” which I’ve learned is a red flag.  People are either fun or they’re not.  The sense of fun that emanates from a naturally fun person comes from how they look at life and how they engage people, not from elaborately-planned “theme” activities, which seem more like work than the actual job you’re hired for.  If someone is trying that hard to have “fun,” they’re overcompensating for something they so clearly lack and trust me, they hate themselves.

This is a very bad type of boss and because these people are technically “in charge,” they’re given the benefit of the doubt far more often the employees who work for them.  Sadly, many of these employees either move on or are so demoralized by the time this type of boss is figured out, it takes lots of money and time to repair the damage that has been done by such people.

How do I know so much about this type of boss?  Because I was this kind of boss… to a certain degree.  Not as bad as Brent, but as much as I love the BBC version of “The Office,” I’ve only been able to watch it once … because it brings back too many bad memories.  Back in college, I became a DJ and “Director of Special Programming” for one of the campus radio stations.  Because I had a lot of enthusiasm and “can-do” attitude, the outgoing leaders felt I would make a good President and General Manager and encouraged me to run for the slot.  Being a sucker for flattery, I ran unopposed and got the position.  I was head of a campus organization that had between 40-50 members and yes, my 21-year old self felt like a real big shot.  Until … that is … I realized I not only had no idea what I was doing, but that I had no interest at all in doing the work of actually managing a group of 40-50 people.  Worse, I had no vision for what I planned to do to move the station forward in the year I was going to be in charge.  The fact that I ran unopposed should have clued me in to the fact that this was a very tough job no one else wanted.  At this point, if I had been smart, I should have seized this opportunity, given it a really strong try, and while I may not have always been successful, my heart would have been in the right place and I would have known I had done my best.

But I didn’t.  I retreated.  Even worse, I wanted everyone to like me and as everyone knows, when you try to please everybody, you please no one.  This was the worst type of approach with the leaders I led.  They were all good people, but many of them had VERY strong personalities, oftentimes in opposition to each other.  Getting all of these types of people swimming in the same direction would be a difficult task for any leader, but my approach, a combination of disengaging or trying to make everyone happy, was the worst possible combination.  Even worse, when I felt like had to be a “leader,” I overcompensated by micromanaging or browbeating.  I’m sure it’s no surprise that this approach did no good.

I could relate individual instances of incompetent leadership displayed by yours truly, but I won’t.  Not because I’m too prideful.  But because 99% of them are too banal and boring and not catastrophic enough to be awful/funny.  The best they would elicit is an eye roll, but most likely they would evoke “zzzzz”s.  They’re not even good enough for the reject bin for “Curb Your Enthusiasm.”  Except one incident does stand out.  Someone from the yearbook wanted to interview me and during the interview, I don’t think I provided a single intelligent answer to any question she asked.  They were softball questions and my answer to most questions were “Um, I’ll need to get back to you on that.”  It’s not that I didn’t know the answer.  It’s just that I only knew about 60% of what I was supposed to know … because I was THAT disengaged.

The one bright spot is that this horrible year happened when I was 21-22 years old.  This was while I was in school with no responsibilities other than my classes and yes, this leadership “job” I volunteered for and the people under me were not earning income and depending on me for survival.  Having this experience at the age of 35, married with kids, a mortgage, car payments, and with people who earn their living off of how I deal with them would have been considerably worse.  And yes, karma bit my ass good later in life by having a couple of bosses that were just like me and yes, it sucked … big time.

There have been managers and leaders I’ve had over the years that have been magnificent in their jobs, mainly because I felt they cared about me, knew what I was doing (without micromanaging), and supported me in what I wanted to do.  These actions of support made me want to make them look better.  I had their back because I knew they had my back.

I want to close by asking any one out there who’s thinking of going into management or leadership to really think about why you want to do it.  You don’t have to like or love what you do every day or even like or love all of the people that work for you.   And it’s OK to feel unsure or scared about whether you’ll make a good leader.  People should challenge themselves and stretch beyond their comfort zones.  But if you’re only taking a leadership position because of the prestige or extra pay, trust me when I say that you’re going to earn every penny … and you will probably find yourself shortchanged, especially given the personal hell you, your family, and your employees will go through.