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Dealing with a bad boss: Nutty horror stories

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OK, who here has a terrible boss?

Today, I want to talk about them, because if you have one, you think about them every single day you go to work.

What makes a bad boss?

Maybe they’re overbearing and rude. Maybe they dismiss every idea you have.

Or maybe they’re the spineless boss that meekly says, “Sorry, I can’t give you a raise…that’s all the wiggle room I have…” If he can’t stand up for himself, how will he ever stand up for you?

Just try to imagine the look on someone’s face on a Sunday afternoon as they think about going back to work for their boss the next day. I can see them in my mind, drinking at a Sunday brunch and complaining about something their boss did. Their friends, who’ve heard this 50 times, roll their eyes and try to change the subject. It’s hilarious…as long as it’s someone else. That last line is also my life philosophy.

A bad boss means that every day — for 8+ hours/day, 2,000+ hours/year — some of us are walking around on pins and needles, dreading seeing our boss. It’s like walking around with a 50lb weight on your shoulders that you can’t take off…because it’s also secretly keeping you alive (aka giving you a paycheck).

Now here’s the interesting part.

Of all the people who have bad bosses, how many leave to find another job? Maybe 1 in 100? Why does everyone else stay? You’re not a slave. You can leave whenever you want.

There’s a lot of boo-hoo, woe-is-me, waa-the-economy-is-so-bad. Actually, no, it’s not. Top performers can get a job in days in this economy. (In fact, we’re hiring for lots of positions.)

If you have a bad boss, it’s not your fault — but it is your responsibility to do something about it. Once you’ve admitted that your boss is bad and you want out, you have 3 options:

  1. Try to change your boss (unlikely)
  2. Find another job (hmm, if only there were some way to find your Dream Job)
  3. Do nothing and complain (I’ll see you in hell)

It’s just like being in a bad relationship. You can blame it on them all you want…but ultimately, it’s your decision to stay or leave.

One of the skills that few people talk about is knowing when to quit. Seth Godin writes about this in The Dip, where he says:

“…What really sets superstars apart from everyone else is the ability to escape dead ends quickly, while staying focused and motivated when it really counts.

Winners quit fast, quit often, and quit without guilt — until they commit to beating the right Dip for the right reasons.”

For all the people who complain about a bad boss, how many of them spotted the telltale signs — years ago? And did nothing?

Ultimately, it comes down to this: You don’t have to accept a bad boss. It’s not “normal” or part of paying your dues. Nobody should have to sigh and say, “Another Monday…back to the grind.”

I actually think a lot of us are in this situation — a lot more than we want to admit. So I want open up the conversation around this.

What’s your boss horror story?

Do you have a bad boss? Did you finally escape? I want you to share your boss horror stories in the comments.

Beyond pure curiosity, I want to start a conversation about this. What made them so bad? And as you write this, notice how it makes you feel.

Share your boss horror story in the comments below. Don’t worry about naming any names or revealing yourself. You can keep it completely anonymous.

This isn’t just for employees, either. If you’ve been a boss, flip it. What’s your employee horror story?

I’m excited to read yours.

P.S. It’s fun to commiserate about horrible bosses. But I’m more interested in understanding what we can do about it.

Recently, I heard one of the most fascinating boss horror stories of all time. It came from a guest in my Brain Trust program, Kevin Hillstrom. Today, Kevin is the CEO of a successful business, MineThatData (and an amazing strategist). But early in his career, he was an awkward junior analyst — with ZERO communication and business skills.

One day, he was sitting in his cubicle and overheard his boss saying horrible things about him behind closed doors.

Instead of complaining about how bad his boss was, he took a totally different perspective — one that changed his entire career.

Check out Kevin’s story here:


The full interview is available to members of my Brain Trust community. If you’d like to learn more about it, simply enter your name and email below and I’ll give you exclusive updates the next time the program opens.

Join the waitlist and learn more about Brain Trust

P.P.S. I’m flying my entire company to Portland, OR, next week for our annual company meetup. If you’ll be in the Portland area on Friday, February 12, we’re hosting a casual, happy hour event with my team and the IWT Community. Space will be limited — click here for details and to reserve your spot.

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  1. Oh man, bad boss? I once had a boss that threw a complete fit because I accidentally broke a coffee pot in the pantry. The best part was that it wasn’t even her’s… and the person that did own the coffee pot was okay with it since I told him that I’ll buy him a new one. She threw a massive fit anyway, about work reputations and how I tarnished her work reputation nonetheless.

    Two weeks later, when I was invited to her room for my quarter review and she continued to act very dramatic about the coffee pot, I quit the job.

  2. My boss wasn’t evil, just offered no leadership and ran the business poorly. There was never any money for raises, or to hire necessary staff, or sometimes even to pay our vendors. I stuck it out for more then seven years, until a couple months ago when I decided it was simply time to go. I didn’t have another job lined up, but I gave my month’s notice and left anyway. It felt good to leave on my own terms, when things were going well in my department. What I’ve realized in the time since is that you don’t have to stay in a job when you are miserable. You can leave. And if the next job you accept isn’t what you want, you don’t have to stay five years to prove you’re not a quitter. Move on!

    • Yeah, that is often a problem. Most people here whine and complain about one specific problem boss that will raise your blood pressure to dangerous level. All people do that to occasionally, and often without realising it. There are certainly sociopaths out there, but they are not that common.

      But a leaderless, directionless company that is just drifting? Very very common case. The problem is that the bosses THINK they know what they want, but they don’t really, and they don’t give clear directions. Often because they only have a vague fuzzy dream about what they want. And when they don’t get what they thought they wanted they can get unpleasant.

  3. I had a bad boss at my last job which I had worked at for over 10 years. The problem began when I applied for the job after writing a 5-year plan for the company which was accepted. I had assumed that since I wrote the plan that the position would be executing that I had a fair shot. She got the job, and I congratulated her on it. She got wind that I had applied and that’s when the issues started.

    My reviews went from 8 years of stellar to crap. then the case building began to get rid of me. She started allowing co-workers to berate me, and would back them up. She started publically humiliating me at all staff meetings, and taking budget away from my projects. the “what is it you say you do here” conversation was on its way.

    I would become physically ill in the parking lot before work and worked like that for years. It was awful.

  4. I have a horrible bos… right now! I haven’t worked for the company too long. I am already looking for a way out. My boss exaggerates and lies a lot and has no integrity. It started at the hiring interview. I was promised the world! Everything I could ever dream of. This is my first job out of university so needless to say that I was not that experenced dealing with higher-ups. He told me the company is a great place to work for, has great structure and potential. Gave me a terrible salary saying he will review it in 3 months. I get in. It becomes clear to me while the company is established, the department they were trying to run is a start-up. Absolutely no structure whatsoever. I ended up working late evenings and weekends trying to meet some ridiculous deadlines. They have no money either. They can’t hire more hands. 3 months down the line I demanded my raise. I was a very valuable employee by then. I keep getting promises. And promises and promises but absolutely no action. I am definitely wasting my time and talents. Here. Nowadays, I still work late… applying to better positions once my 8 hour per day is up 🙂

  5. My bad boss was this douche named John. About 3 months of working with this “B+” Player…the guy literally didn’t know how to project plan, never had a successful development cycle the whole time. That and he was just rude and never cared about company priorities, just “his” priorities. Oh that and he constantly brown-nosed to the execs while simultaneously treating the rest of the devs like sub-par people.

    I did my best to coach the guy as I was much more familiar on how to efficiently run a Scrum Development process, suggested a lot of ways to improve our dev cycles, how to run meetings, prioritizing, using in-house tech, etc. But he was one of those older guys who just thought he knew best. Nonetheless I just couldn’t handle dealing with all his inefficiencies. Eventually it got to the point where his inability to manage anything correctly or efficiently impacted my own productivity. That’s when I had to draw the nine; he was making ME look bad. I just gave my two weeks notice.

    Luckily for me, I have ZERO debt and a heft “Rainy Day” fund, so quitting and going on a 4-month vacation was no problem. But yeah never again will I work for a sub-par boss.

  6. My last job had a boss that was nutso. He seemed to be afraid of doing actual work, despite the fact that he was running a department. When you met with him, he would go off on long story telling tangents about how great he was or how he did amazing things 20 years ago under the guise of “teaching” you. He also frequently badmouthed coworkers to me and undermined their accomplishments while publicly praising them. Friday mornings were spent in a conference room, where he would share news from other departments and ramble on about how they were all out to get us and didn’t know what they were doing, and then we all went around the table and shared what we worked on that week. It took 2-3 hours EVERY WEEK, think of the time wasted. He also assumed that if you ever took sick time, you were not actually sick, you just wanted free vacation time (he also worked sick and often infected half the office). He antagonized every group he was supposed to work with but was somehow never let go. And I would understand this if he produced great results, but in the three years I worked there, he never did. He either shared credit for colleagues’ work or had something in the works, but never closed. We were going through a big push and he frequently tasked a colleague with projects and then changed the purview of them when she was set to execute, telling her she was moving too quickly and also reprimanding her for not producing results. I think he kept shifting targets because he was afraid that he wouldn’t produce results.

    Actually, all of the higher ups were nutso, now that I think about it. Those who stayed were in it because they were yes men, too comfortable or afraid to move on. I stayed in three years (which was two too many), but the tuition benefits helped me get a masters for very cheap. I got it in May, quit in July.

    • So, umm, can we remove the picture from this post? I didn’t realize you use disqus comments and would prefer not to have that attached.

  7. Yep, had a few of those….
    #1. Set up timebombs on the system (we were IT) when he thought his job was in jeopardy. If he didn’t sign on for two weeks they would start going off. I let the company know when I put in my resignation. They offered me his position 6 months later when he resigned….. but there were other issues there so I politely declined. (There was no proof on timebombs as he had removed them.)
    #2. Had to be “right”, and never accepted input and was know for yelling across the cube farm “Last time I checked I was Manager”. During this one I discovered Liz Wiseman’s book “Multipliers” – those people who you will jump through fiery hoops for. The opposite is a “Diminisher” – putting a name to it and having mitigating tactics keep my sanity until I was able to earn a professional certification that enabled me to get that “Dream job”. Also, that professional segment has a local chapter for which I have been on the board for 5 years and as of Jan 1st am President. I found my “validation/calling” outside my direct work situation.

  8. In my first office job, I had a boss I liken as a male version of The Devil Wears Prada. I started working for him in the first place because at the time I needed a job, and got the interview because he happens to be my great-uncle by marriage. I say “got the interview” because I still had to interview and prove myself to stay. He was fond of referring to past employees as those who “couldn’t survive,” ergo those of us currently employed were surviving (at least temporarily). He had decades of experience in building companies, government proposals and contracts. So the value of what I learned as a direct report was not lost on me. However, the knowledge gained was not worth the way I was constantly demeaned by his treatment. Incredibly rude and disrespectful, with outrageous expectations – he once insisted I come to the office after a hurricane “so the team could all be together” when there were downed trees and power lines everywhere. I could easily have worked remotely with my laptop (or taken off – nothing urgent going on). He constantly demeaned the entire team in front of each other as well– it was very embarrassing in weekly meetings to see coworkers chastised right next to you, especially those higher in the totem pole.

    I worked for him for about 2 years before the company faced some challenges and laid everyone off for lack of funds. I think I stayed because of the family connection; because I’m a hard worker and by nature don’t like to back down from a commitment; I was doing well despite the challenges and earned a promotion within first year; and mostly, I think, because I was young and inexperienced, and it didn’t occur to me that I didn’t have to let someone treat me like that just because they were in a position of power.

  9. My former boss was truly nutty. He didn’t stop at throwing me under the bus and criticizing my work in front of my clients. (Whom privately apologized to me for HIS behavior!)
    One night he took me to dinner and waited until one glass of wine was consumed when he asked me, “what’s it going to take to get you to convert to my religion?” I was floored. It felt like an ultimatum and all I could say was “do you realize how umcomfortable this question is for me?” His response? “Just imagine how uncomfortable I am asking!” Oi vey. It took me years before I left, thanks to him being in another, out of state office. But still…

  10. Oh man — I’ve got one. I got a job offer from this place in December. They told me my start date was Jan. 1. So I gave my other job 2 weeks notice and quit in time to start the new job at the start of the year

    Well, as it turns out, the boss wasn’t so sure she wanted to bring me…So my start date was Jan 1. It dragged out to the middle of February.

    Keep in mind that I quit my old job and thought I was starting a new one, so I spent a whole month out of work. My mistake — I know, but still.

    When I finally got started on day 1 of this new job, the boss walks up to me. Points to a desk with a huge stack of papers on it. And says, “You can go ahead and get started.”

    I have no idea how to log in to my computer. I have no idea what I’m even working on or where any of these papers go. So I start frantically asking people around me — “What am I supposed to do?”

    They’re not much help, as they’er from a different department.

    So the boss comes back over around lunch. “You mean you haven’t finished yet?”

    “I don’t even know where to start?”

    “I knew we shouldn’t have brought you on. This is the most simple task we have.”

    I wanted to scream back at her, but I refrained.

    God, I never thought that first day would end.

    I got home, told everyone I know about it. And decided I was going to quit.

    When I went to the boss the next day, she said, “I already fired you — so I don’t care. You can leave your badge on your desk.”

    2 weeks later she send me a bill in the mail, saying I never paid for parking, broke the computer, and owed her time for her services.

    She even threatened a lawsuit.

    I’ve never met a worse person in my life. Needless to say — that was the worst boss I’ve ever had and will never repeat that mistake again.

    • Wow, this has got to be one of the worst I’ve ever heard. So how did it resolve?

    • End thread. Go home, everyone.

    • I worked for a sociopath named Matthew. He did the usual- presented my work to his superiors as his own, micromanaged, bullied, belittled, and muddied the waters. I would cry on my drive in, because I didn’t know what freakish passive-aggressive unpleasantness he would have in store for me. He tried to take disciplinary action toward me for going to medical appointments that he had previously approved. He wrote me up for taking a half-day off to go to a friend’s funeral in another state. I was out for a medical issue for a week, and he demanded my coworker keep the cubby door of my cubicle open to obscure a picture I had up because it disturbed him.
      The picture was a photo and quote by Gandhi. Dude, if Gandhi upsets you, maybe you’re a freak.
      I left after a year in the middle of the recession without a new position lined up, and it all worked out fine.
      And I hope he gets dick cancer.