If you’re like most people, you’ve probably had a variety of jobs over the years. And unless you were working for yourself (or if you own a company) that meant you had a boss.
Relationships with bosses come in every shape and size. If you’re lucky, you’ll have a friendly relationship with them and nothing more. It’s not necessary to be friends, but it’s always more pleasant if you get along.
Part of it boils down to that weird superior-inferior relationship. Yes, your boss is in charge of you. They have to find the balance and show their employees respect while also having authority. Some bosses aren’t very good at that. They’re either too permissive and get nothing done or they’re tyrannical and treat their workers like slaves.
Then there are the bosses who are the cream of the crop. They know that even though they’re in charge, they still need to work with their employees and be respectful. When you have a boss like that, it makes work so much more enjoyable. A good boss can literally turn a workplace around for the better. These 50 boss-employee relationships are #goals for workers everywhere. You might want to take notes.
1. Who are you calling ugly?
Ugly Christmas sweater parties are popular around the holidays, but this employee really stepped it up a notch. It takes a lot of guts to call your boss ugly to his face.
2. When you’re asked to dog sit for your boss
When your boss hires you to dog sit for a month, it’s your chance to prove you’re responsible and proactive. Or your chance to replace all his photos with pictures of you cuddling the dog. It’s your choice.
3. Is this good enough for you?
One boss asked his employee to announce when they was leaving for the bathroom. The employee responded with this sign. Hopefully, this isn’t too subtle for the boss.
4. This is sabotage
It’s always nice when your boss gets you a delicious, decadent cake for your birthday, right? Unless, of course, the two of you have been in a dieting competition.
5. This is sick
When your boss goes on vacation, you can leave his office untouched. Or you can replace all the photos of his kids with creepy Photoshopped versions with your coworkers’ faces.
6. Level up
Companies aren’t always honest about the level of commitment — and detriments — of being promoted. Sure, you get a raise, but not everything’s fun. At least this boss is being honest.
7. Is that his official title?
This boss is going for the “authority” line, and that’s okay. At least he’s pretty upfront about who’s in charge around here. It’s always nice to have a boss who tells it like it is.
8. If we have to be on camera, I’ll be a wizard
When you work from home, you often have to deal with annoyances like Skype meetings that could have been emails. Of course, to make them more interesting, you can dress up like a wizard.
9. What a prick
An employee’s boss asked him to set up the tables for a meeting and he saw an opportunity. It’s a good thing the boss has a sense of humor and won’t be reporting him to HR.
10. When you think your employee’s a Photoshop expert
One boss didn’t like his expression in the company photo, so he asked one of the employees to Photoshop his face. So, he did …just not the way he expected.
11. Something tells me his employees think he’s conceited
It’s hard to know what to get your boss for Christmas or birthdays. One company decided to go with the “giant oil painting self-portrait” route. I’m not sure whether the boss’s reaction is amusement or horror.
12. You’ll never wonder what time it is again
If your boss has a sense of humor, don’t ask for a “desk clock” without going into specifics. You might just find yourself with a giant Justin Bieber watch that everyone will judge.
13. You failed the test
Some employees will do anything to get a day off of work, even faking a doctor’s note. One boss wasn’t having it and graded the fake note accordingly.
14. This is the meanest thing anyone’s ever done
When you work for a welding company and have access to equipment, it opens up some interesting possibilities. For example, you can package your boss’s Christmas gift like this. Good luck.
15. It always has to be a competition.
After the boss hung his toddler daughter’s artwork in his office, an employee decided she couldn’t be the only artist represented. So, she added some work of her own.
16. We hate you, Cody
When one of your employees makes a mistake, there are a couple of ways to handle it. You can give them a formal warning or have a meeting. This boss prefers the “public shaming” method.
17. Convincing
When his boss installed a security camera, an employee decided to prove how dedicated he was to his job. Of course, it might be a little more convincing if he wasn’t wearing such a miserable expression.
18. You’ve been Caged
When the boss puts up a security camera to monitor the employees, you can bet one of them will sabotage the attempt. In this case, he got an eyeful of this horrifying picture.
19. Take that, mice
With mice getting into the cable box, a boss asked one of his employees to take measures against them. He should have been more specific. Maybe these are unusually educated mice.
20. Picture it
A boss wasn’t mincing words about his feelings on being interrupted during his vacation. Better take up any problems with Tracy and Don.
21. She found a solution
When her boss wouldn’t stop complaining about her uncovered ponytail, an employee found a solution. It wasn’t the one the boss wanted, but it was a solution.
22. Who are you calling a whiner?
After an employee complained to their boss, they received official notice in the form of a “Hurt Feelings” report. It’s always nice to know your superior takes you seriously, isn’t it?
23. It’s great to learn new things
What started out as a bad social gaffe ended up making a grieving employee laugh. Thankfully, they were all able to take it in stride — and the boss learned an important lesson.
24. Put everything in writing
An employee was sitting quietly at his desk when his boss came over and slapped this on his chest. Sometimes, they just can’t resist making a power play, can they?
25. The boss wanted candy
Just look at this “report” from City Hall in 1988 — it proves that some bosses have always been silly. This guy must’ve really like Smarties.
26. Consider him your fairy godmother
After an employee asked for an iMac, the boss was happy to grant his wish. Of course, they say you should always be extremely specific when making wishes.
27. He fixed it
An employee got this for their boss who absolutely loved it. Of course, he was worried HR would complain. So, he adjusted it to be more appropriate for work.
28. The boss is highly concerned about the company’s reputation
Yelp reviews are important for businesses and can make or break their reputation. The boss was determined to get to the bottom of one review.
29. Isn’t that subtle
When the boss turned 50, her employees decided to show her a little love by giving her a birthday cake. Of course, they also took the chance to remind her of her inevitable demise.
30. Very funny, boss
Work can get boring, which is why it’s the perfect place for dumb pranks to flourish. A pool manager thought it was hysterical to make the lifeguards try to undo this lock.
31. What a payday
Sometimes, construction workers and contractors get paid in cash, which can make things a little complicated. Of course, they’re even more complicated if your boss likes to pay you in ones just to be funny.
32. I don’t think I want to go into work today
Most of us don’t have bosses who use Snapchat, much less ones that actually send Snaps to us. Then there’s this boss who likes to wake his employees up like this.
33. Pretty good analogy, actually
Don’t you hate it when your boss does a lap around the office to see who’s browsing Facebook? They always seem to choose the one moment when you’re not working.
34. I’d wear them every day
In case you were wondering, the bottom of the sock says “Haha, just kidding.” They were a gift from a boss to an employee, and frankly, they’re amazing.
35. Geez, don’t hide your feelings
You learn a lot about your coworkers from spending eight hours a day with them: their family life, taste in music, and favorite foods. Of course, all that can get on your nerves, too. This boss decided he just couldn’t take his employee’s music any longer.
36. This deserves to be commemorated
Bosses have to hear a lot of ridiculous excuses for why employees were late or absent. This one was so fantastically bad the boss thought it deserved to be in a place of honor.
37. A classic
It’s amazing when you win a bet against your boss. It’s not so great when he waits a full year to pay you and then does so exclusively in pennies.
38. He’s very passionate about bathroom cleanliness
A germaphobe boss couldn’t take it any longer when a mystery employee was throwing paper towels on the bathroom floor. In his defense, that’s a pretty crappy thing to do.
39. Is that random?
Some companies ask their employees to comply with random drug testing, but this isn’t what I’d call random. In fact, the boss gave this to the employee who’d just come back from Burning Man.
40. So like…20 boxes?
I’m assuming this boss is joking — at least, I sure hope she is. Also, it might be helpful if she would explain how many pens qualifies as a “fuck ton.”
41. An important reminder
Bosses aren’t always sympathetic to their employees’ work woes. At least this boss tried with a festive gift. It’s always nice when those come with reminders of harsh reality, right?
42. Thanks for your concern
No one said you couldn’t be friends with your boss, but there is such a thing as being a little too close. One way to tell? When your boss slides this under the bathroom door.
43. Tell us how you really feel
When their employee left to join another company, the boss got her a delicious chocolate cake. Of course, it had some honest sentiments written in the icing.
44. Nailed it
When your boss goes on vacation, you should behave yourself and be a model employee. You definitely shouldn’t take a photo with a coworker and use it to replace a personal photo. Wink, wink.
45. Yeah, about that
If you go on a date with your boss’s daughter, you should probably tell him about it. Otherwise, he might find out another way, and then the whole office knows.
46. We have new company cars
Isn’t it nice when a company provides its employees with perks? They might not be luxury vehicles, but at least they’re good for the environment.
47. He ate an entire pecan pie
An employee brought a pecan pie to work and was mystified when it disappeared from the fridge before 10 a.m. Then he found the empty dish on his boss’s desk. What a legend.
48. Mind your own business
Snooping in someone’s mail is illegal, but being annoying about it isn’t. An employee really wanted to know what was in his boss’s package. This is how he asked.
49. I think he’s lying
Bosses are like dads: they love to make promises and then pull the rug out from under your feet just for a good laugh. In this case, the boss informed his employees he’d gotten them a “Nintendo switch.”
50. Fight the man
Did the boss block Facebook on all the work computers? Make your own Facebook “wall” for all the employees. Make sure it’s somewhere he can see it.
50 hilarious boss-employee relationships that are untouchable
Cedric Jackson
12.09.19
If you’re like most people, you’ve probably had a variety of jobs over the years. And unless you were working for yourself (or if you own a company) that meant you had a boss.
Relationships with bosses come in every shape and size. If you’re lucky, you’ll have a friendly relationship with them and nothing more. It’s not necessary to be friends, but it’s always more pleasant if you get along.
Part of it boils down to that weird superior-inferior relationship. Yes, your boss is in charge of you. They have to find the balance and show their employees respect while also having authority. Some bosses aren’t very good at that. They’re either too permissive and get nothing done or they’re tyrannical and treat their workers like slaves.
Then there are the bosses who are the cream of the crop. They know that even though they’re in charge, they still need to work with their employees and be respectful. When you have a boss like that, it makes work so much more enjoyable. A good boss can literally turn a workplace around for the better. These 50 boss-employee relationships are #goals for workers everywhere. You might want to take notes.