19 People Share Their Horrible Boss Experiences

July 22, 2019

I’m going to be honest — I’ve had my fair share of horrible bosses. There was the boss who screamed at me for doing further research into the company (since I had to be up to something sketchy) and the boss who sexually harassed me and made every single day uncomfortable. How could I ever forget about the boss who’d send me and my team countless praises through email, just to quietly cut our hours and responsibilities days later.

Being a boss is hard, but so many people screw it up based on the ego trip it can bring.

Dealing with a bad boss is often a horrifying situation in the moment. It’s not quite possible for many of us to be able to afford the essentials without one. So, we often do whatever it takes to shield the negativity and hardships and focus on the fact that, at the very least, these bad days will ensure we’ll be stocked up on toilet paper and canned goods for a couple of months.

Of course, the second we get out of these bad situations, things change. In fact, they almost become comical.

When we’ve rebuilt our confidence and have found a better fit with employment, we can sit back and re-examine some of the ridiculous things our past bosses said or did. And sometimes, making the internet fully aware of the insane situations we’ve survived helps us fully get over them.

Here are some of the worst boss experiences on the internet.

1. Why People Don’t Disclose Surgeries

Even if your boss tries to pry, remember that your medical news is your own.

A double mastectomy can be a traumatic experience, especially since it’s most commonly tied with breast cancer and breast cancer treatment. Plus, all surgeries come with a level of fear. Even if it’s a common procedure, it’s not a vacation for anyone involved. Having a boss examine your chest after hearing the news is uncalled for and violating.

2.  The Paranoid Boss

We’ve all met people like this before. Things get uncomfortable when you have a boss who needs to know how every paperclip is being used.

However, they don’t usually face such tragic endings based on their paranoia. May this be a lesson to all of the penny-pinching bosses out there. It’s so much better to hire employees you trust, than employees you constantly need to secretly monitor and harass. (Secret cameras, in general, shouldn’t even be a security measure that crosses your mind.)

3. The Pregnancy Rumor

Doesn’t this sound like something Michael Scott would pull?

Word to the wise, never assume anyone is pregnant. Even if they look like they’re nearing the 40-week mark, always let the woman talk about their pregnancy first. It’s just common courtesy, especially since “bouncing back” after a legitimate pregnancy can take a long, long time. And if you’re commenting in regards to boobs? You may want to rethink about your social etiquette altogether.

4. The Fetish

People often have fetishes, but they don’t mix them with work.

If you happen to have a romance blog online, lock it down. Don’t trace it to your name, and don’t visit it (or write in it) during work hours on your work computer. It’s not illegal, but it can lead to several awkward situations that you won’t be able to recover from. Especially if you made your hiring choices due to sexual attraction. (Which, gross.)

5. The Chick-Fil-A Failure

Wait. Was this person’s boss one of the Chick-Fil-A cows?

When you’re a manager, you want your business to do well. But if your success is based around a big health scare that has left people worried and concerned, maybe you shouldn’t voice those thoughts out loud to your employees. Mad Cow Disease reportedly can’t affect humans, but they can get something close that’s called variant Creutzfeldt-Jakob disease. It’s scary, but very rare.

6. The Thief

Everyone knows employee theft is wrong — especially when money is involved.

This guy is particularly sleazy, as he penalized his staff for something they didn’t do. If you’re thinking about pulling a similar move, just know this — you will get caught, and every employee you’ve accused of being a criminal before that moment will pour over the police report with a strange sense of relief.

7. The Boss Who Just Doesn’t Get Time

Should he have a gotten a tattoo? Sure, why not?

But, a good boss will realize that there’s a time for getting ink — and it’s probably not smack dab in the middle of a busy workday. Unless he scheduled that time aside and let his employees know, which it sounds like he didn’t, he demonstrated how clueless he is about how his company runs.

8. The Stalker

Who’d want to be followed into the bathroom every day?

Bathroom issues are highly personal and a little embarrassing as-is. Nobody wants to admit to the world that they have diarrhea or bad stomach cramps. Knowing your boss followed you in there, or having them camp outside to make sure your issues are legit, is just a nightmare come true. Whatever happened to privacy?

9. The Email Goof

Note to self: Always proofread your emails.

You shouldn’t even joke when it comes to bad words and insults. Use actual paper and a pencil to jot down your feelings on a negative client if need be. Then, immediately shred it so it doesn’t see the light of day. This boss likely cost his employees a ton of money and may have lost a few big contacts due to one bad move.

10. The Heated Insult

We all come in different shapes, sizes, and colors.

Pale skin in the summertime only started being embraced somewhat recently. Which is a shame, since all skin is beautiful —  especially when it’s healthy. This boss made a comment that made his employee feel bad about herself for a lifetime. Yes, words can carry a lot of weight. Bosses should always keep negative comments about looks to themselves.

11. The Homophobe

It’s still 2019, and some people still can’t get over the fact that women can be married to each other.

Not only was this boss snooping on his employees’ personal lives, but the fact that he brought it into work is an issue in itself. Whatever you do at home is your own business, unless it greatly affects your capabilities at work. Having a same-sex partner, and showing PDA on occasion, doesn’t fit that category.

12. The Boss Who Didn’t Pay

You don’t work for a place for exposure, or just for the heck of it.

You work for a paycheck. So, you might want to make sure you have enough money to pay your employees if you bring them on board. Otherwise, you’ll have a lot of bounced checks and upset employees who are probably looking for a solid exit plan. If it happens, at least apologize and promise it won’t occur again. (And, make good on that promise.)

13. The Boss Who Chose Her Employee’s Career Path

If an employee isn’t good at their job, a good place to acknowledge that is in a meeting or review where performance will be openly discussed.

Not when you’re trying to push another job at them. This boss could have assumed they were doing the right thing, but it’s not her place to force an employee into a career path they might not be into. Chances are, this employee was fine with publicity — the comment was just a power play for the boss to feel more in control of the situation.

14. The Wall Of Weakness

If your place of employment has one of these, just run.

Some people are better at their jobs than others. But unless you’ve worked for a debt collection place before, you don’t know how negative it could be. When you’re asking people to pay money, the people who’ll comply will be in the minority. Maybe this place could have celebrated the “strong” employees in a way that didn’t put everyone else down.

15. If Only There Was A Pump Room

All pumping moms can agree — pumping milk is tough.

It’s even harder to do at work when your privacy isn’t guaranteed and your bosses need to be informed every time it happens. It’s a job within a job. This is why a lot of women strive to have a dedicated pumping room in their office, to avoid the awkwardness of coworkers questioning things or barging in.

16. The Amateur Writer

Again, writing pornography is a legit, albeit awkward, hobby. Just, do it outside the office and preferably under a pen name.

This can definitely be seen as sexual harassment. So bosses — no matter how close you think you may be with your employees, just know that asking them to edit your pornographic writing endeavors is a line crossed. There’s no way around it. Find someone else to help you out.

17. Lack Of Benefits

If you hear rumors of this happening at your workplace? Consider leaving before they fire you.

You have a right to the benefits you’ve earned. And if this place is so stingy that they don’t want to offer healthcare to a good employee, preferring to train someone new on a three-month rotation, you don’t need them. Find a place that appreciates you and wants you to be your best self.

18. The Bad Dress Code

There’s no cardigan out there that wasn’t meant for an office.

If a boss says something like this to you, it means that he finds you to be attractive — and is blaming you for that. This puts you in a very awkward situation. Not only might you not feel safe in your work environment anymore, but you’ll feel like you need to change your whole wardrobe. Consider making things easier by resigning in favor of a better job.

19. The Boss Who Doesn’t Understand Holidays

Jewish holidays deserve to be celebrated by those who follow the Jewish faith.

But much like Christmas, or Easter, or your own birthday, they’re not something you can openly change. Sure, some people celebrate multiple Christmas celebrations around December. But Yom Kippur, which is one of the biggest Jewish holidays, is one specific day of fasting. Observing it on a day that makes sense to someone else takes away its whole purpose.