Bad Bosses, Part 2: Action Heroes, Guns, and Explosions

“Your boss is a woman?  Now this is a strange bank.” – It’s Always Sunny in Philadelphia

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In order to dress for success they tell you to dress for the job you want, not the job you have.  So I found out where my boss shopped for clothes.  I’d see what they wore, and then wear the exact same outfit the next day.  My boss at the time, Marji, thought that was just a little weird since horizontal stripes weren’t at all flattering on me. 

It’s both a blessing and a curse to get to the end of writing your post and finding . . . it’s too long.  It’s a blessing because if I can break it into two posts, hey, I’ve already got my next post written, which might get me to bed by 2AM instead of the usual.  The curse part is that the post has to have a natural break between part one and part two – thankfully this one did.  The other curse part is that I actually look forward to writing a post – and the one I had planned for Friday will have to wait a week.  But it’s gonna be funny.  Part 1 is here: Bad Bosses, Part I, Including Garfield as Written by H.P. Lovecraft, and part 2 is below.

It’s been my experience that all good bosses look the same, since they are all clones of me, or at least the “me” in that first performance review (JW note: it was described in the last post, and it was a really good performance review).  And I’ve had plenty of bosses in my career – in one two-year period I went through five bosses, and I am averaging a new boss every sixteen months over the years of my career.

Based on my experiences, the traits of good bosses that I’ve had are listed below.  Good bosses are:

  • Concerned about doing their duty for their company. They display loyalty – they do their job.
  • Good at setting clear expectations on behavior and expected work outcome. You know what you’re supposed to be doing.
  • Never smelling of grilled onions.
  • Able to create an environment where honest questions are encouraged.
  • Good at providing the tools, time, and space the employee needs to get work done.
  • Available to do children’s magic shows for birthday parties.
  • Honest with employees, and give clear feedback meant to help them improve.
  • Quick to recognize that mayonnaise is not a French musical instrument.
  • Courageous – the truth is the truth, and they’ll share that up and down the line and damn the consequences.
  • Reluctant hold a knife to the secretary’s administrative assistant’s neck.
  • Genuinely concerned about the employee.
  • Treat people (generally) fairly.

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It’s always a shame when you have a great boss and he breaks a leg and has to be put down.

There are times I’ve managed to screw up most of the rules I’ve listed above when I was a boss – that’s why I was able to list them off the top of my head – you remember your mistakes.  But you learn from them, too:  One of the biggest compliments I got was when I was leaving a job for a new company.  The Chief Operating Officer came in to say goodbye and told me, “I hope you’re going to be supervising people at your new job.”  Maybe he wanted the new company I was leaving to join to fail, but I took it that he appreciated my efforts to learn and be better as a boss and wanted to pass that legacy on to other companies through people like me.  You’re right.  He wanted me to mess up that other company.

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I imagine this every time I walk into work and use the remote to lock the doors to my car without looking.

Notice I didn’t mention charisma as a requirement to be a good boss.  You don’t need to be an Elon Musk to be a great boss – and I’ve heard he’s not a particularly good boss unless you’re his weed dealer.  Notice that I didn’t mention intelligence – in some instances really high intelligence works against you as a supervisor since it can make it more difficult for you to communicate well.  Would I rather have a smart boss or an honest one?  Would I rather have a smart boss or a courageous one?  Would I rather have a smart boss or one that didn’t constantly smell of grilled onions?

Most of the time, the cause of a really bad boss is due to their fear, namely fear of getting fired or fear of missing a promotion or fear of missing a rung on the corporate ladder.  If that were to happen?  He couldn’t afford to pay for the “hot stone massages” his wife was getting from Günter, her “masseuse.”  However, sometimes you get bosses that are so strange they remind you of Cousin Eddie®:

One boss I had actually lived in his office, as in slept there every night five or six nights a week.  He claimed to be a member of a biker gang, and told stories of holding a person upside down from a bridge as the gang gently convinced him to be out of state so he couldn’t testify at an upcoming trial.  He told about buying a girlfriend a “little car” to convince her to have an abortion.  And the time he broke a bottle to use as a weapon because “The Indian” was trying to knife him.

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This might not be a completely faithful adaptation from the original story.

And as a boss, whenever I needed help, or a risky event was about to occur, you could count on him to be three states away.  As bad bosses go, he wasn’t horrible, since after I convinced him that if I looked bad, he looked bad, he had my back when we talked to corporate.  Working for him was a really weird nine months.  Normally I throw in a joke or an exaggeration in my descriptions – but in describing this boss?  Nope.  That all happened.

To be clear, with the exceptions listed above, almost all of the rest of my bosses have been great people who were of good character and really interested in helping me develop as a person and as an employee.  But where all good bosses are similar, bad bosses are often unique:

  • The Seagull – The Seagull is a boss that gets a new job every year or two. Why?  Because he flies in, makes a mess, and stays until he’s kicked out.  Miller was a Seagull.  Keep good notes for the aftermath.
  • The Shadow – Whenever anything important happens, they’re gone. Whenever you have a question?  They deflect.  Literally, it’s like not having a boss at all, or at least a boss that will make a decision.  You will have a boss if one of your choices goes wrong, however, because the Shadow will quickly (and correctly) point out that he never told you to do such a thing!
  • The Burnout – The Burnout peaked twenty years ago, and is mad and bitter. His back hurts.  You make too much money.  He wants to retire, but has to wait another year for Medicare™ to kick in.  Until then?  He wants to inflict as much pain as possible on the office because he wants everyone to hurt as much as his back does.
  • Captain Ahab – Captain Ahab is great because he has a vision. Companies love Captain Ahab leaders because they become obsessed with obtaining a vision.  The upside?  Your mission is clear, Ahab makes sure you have everything you need.  And you will work 80 hours a week to accomplish it.  These aren’t 80 hour weeks of playing Minesweeper®, no, every minute is fully used because (Spoiler Alert) that Moby Dick isn’t gonna spear itself.  Ahab doesn’t care about your family, at least during work hours.

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He then tried to hypnotize the people in the meeting using a pocket watch.  The work was rough – 90 hour weeks for months on end, but we got free coffee and he’d buy us catered dinner if we had to work past 9pm.  On a Saturday.   

  • The Sphinx – You’re always guessing. The Shadow won’t give you any sort of answer, but The Sphinx won’t tell you what he wants, but you can be sure that The Sphinx will tell you if it’s wrong.  Generally loudly and when other people are around.
  • The Politician – The Politician cares about only one thing – does it look good? If it looks good and is immoral or illegal?  Who cares?  The Politician is most commonly heard saying “perception is reality.”  The Politician always dresses carefully – almost as good as his boss.  The Politician seeks constant movement.  They can avoid being blamed for messes they make, but will loudly point out the mess they inherited in their new job.  Your value to a Politician begins and ends with you being useful to them.  Otherwise?  You don’t exist.

Your defense if you have a bad boss in almost every case if you want to keep your job is the same:  do your best at work.  Work hard, and don’t break the rules or the law.  Be nice.  And if it sucks too much?  Get a new one.

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While traditionally thought of as a good boss, Washington had a few buttons you didn’t want to press, although he did light up Ye Olde Twitter® to piss of Adams:  “King George . . . Washington.  Verily that soundeth goode.”

One other note:  if every boss working at a company is a Bad Boss, one of two things is going on:

  1. The Bad Boss is what they really want. Unless you can make it work, you have to leave.  Sooner or later, the messes a Bad Boss makes will stick to you.
  2. It may be you. I know that there have been times in my career when my attitude wasn’t optimal.  It’s probably the boss.  But always leave room and examine that the real problem isn’t you.

Okay, I’m now officially sick of Mack the Knife.  But I still don’t feel bad.  And if you’d like to share a bad boss below, feel free.

Author: John

Nobel-Prize Winning, MacArthur Genius Grant Near Recipient writing to you regularly about Fitness, Wealth, and Wisdom - How to be happy and how to be healthy. Oh, and rich.

19 thoughts on “Bad Bosses, Part 2: Action Heroes, Guns, and Explosions”

  1. The US military officer corps claims to want good bosses, but they select for bad bosses. The higher they go, the more they resemble politicians.

  2. Great post. Mr. Wilder already knows my bad boss stories, so I will not go into great detail here. After years working for large Fortune 500 companies, I took a job with a smaller, family owned business. That move probably saved my career, but to be honest, it was prompted by a terrible boss. Life is too short to work for idiots and liars. I thought I would be very happy on the day he got fired, but I was not. My current co-workers probably think I’m making up my stories of bad bosses and corporate bureaucracy. The people that are often most critical of their bosses, have never been a boss themselves. It is not an easy job to be a boss, but that is no excuse to be a sociopath.

  3. For the most part if you have a boss that has a good home life where he is in control then he will be a good boss…The opposite is true also if he isn’t the master of his family then he will be a tyrant at work because he is trying to make up for the lack of control in his own home…

    1. Exactly. It’s the busybodies that run the Homeowner Associations that have no power in their life that have to show it somewhere. Perfect point.

  4. Now you went and pressed MY buttons. Washington was a flaming bunghole. He stop-lossed volunteers, didn’t pay them so they couldn’t support their families, then executed them for justly deserting. He had a bodyguard of over 300 men. And it was to protect him against his own men, not the British ( if it was the British, he would have selected and retained according to loyalty, and used regular troops instead of a special corps ). He was also an elitist prick, a wanna-be royal, who had no problems using troops as cannon fodder so that his was judged an equal to Continental armies. I could go on, but you’ll all just start whispering “conspiracy theorist”

    1. I have great bosses, while working construction the company owner (being a pilot) flies in and stirs up things then flies out. So is that eagle management? Or as the company joke goes pidgeon management. (Fly in, shit all over everything, and leave)

    2. Wow! That’s a first take on that – I do know he married for money, and also had a really big bar tab.

  5. The point that if a “company has all bad bosses, it is probably what they want” is absolutely true. A corporate culture is the defining issue. Or lack of culture. If the person running the whole operation has no specific idea of what is happening below him or her, or runs the place emotionally, look out!

  6. One of the biggest complements I got was …

    Please accept a sincere compliment from a proofreading OCDer on this post, which is up to your usual high standard of laughter and thought provocation. However, unless you are a 55-degree angle presented with a 35-degree angle, you didn’t get a complement; instead, you got a compliment.

    There. Now my pathetic life once again has some spurious illusion of meaning.

  7. Americans look forward to the stock market crash because they think that they’ll be able to buy homes cheaply.

    Americans don’t realize that when the US Ponzi economy collapses, ATM cards won’t work, banks will close, companies will shut, cash will be worthless, the water and electricity won’t work, there will be no government workers to transfer titles, there will be roving mobs of starving people, and there will be no police to protect property.

  8. Your defense if you have a bad boss in almost every case if you want to keep your job is the same: do your best at work. Work hard, and don’t break the rules or the law. Be nice. And if it sucks too much? Get a new one.

    A few observations on that point, in no particular order.
    1) You’re wrong on that point. Sorry, but no. Or at best, woefully incomplete in that assessment of options.
    2) You’ve clearly never seen A Shock To The System, starring Michael Caine (yes, that Michael Caine), and written by Andrew Klavan.
    3) Google Klavan, if you’re not familiar with his recent work. Esp. on YouTube.
    4) Watch that movie, whatever it takes. We’re talking corporate masterclass here. It should be part of all MBA coursework, if only to remind managers they aren’t immortal. Literally.
    5) You may then revise and amend your prior remarks.
    6) Your revised take on that point will be even funnier. I promise you. It may even be worth its own post. (Think about this one carefully, especially with Halloween approaching. “Dilbert, as written by Gomez Addams”, or somesuch.)
    7) When have I ever steered you wrong?

    1. “Your defense if you have a bad boss in almost every case if you want to keep your job is the same: do your best at work. Work hard, and don’t break the rules or the law. Be nice. And if it sucks too much? Get a new one.”

      I generally disagree with Aesop at my peril.

      On the other hand, from bitter personal experience, if you elect the “do your best, to keep your job, and, if the suck is too great, get a new one” avenue, TIMING IS EVERYTHING!

      be certain that you bail, BEFORE your rancid soon-to-be-ex-boss can gin up some bullshit excuse to can you. If you get the timing wrong, as I certainly did, well, then you are unemployed, and looking for work. THAT sucks, even worse than any job I have ever had. Including working for a Big City EMS, with no supplies. (no shit. We would beg gauze and roller gauze from the ERs we ran into!)

      Including the hospital that staffed a SIXTEEN (16) bed urban ER with three (3!) RNs. On midnights.

      1. I’ve been lucky on boss quality (generally), and lucky to monkey-branch from one job to the next. Heck, I’ve been lucky that my best opportunities just fell into my lap.

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