21 Clueless Bosses Who TRULY Are Making Their Employees’ Lives A Living Hell


1.This boss who has a VERY demanding cellphone policy:

u/Rich-P / Via reddit.com

2.This boss who got mad that employees use too much toilet paper…but this is the toilet paper:

A hand is shown holding a thin, see-through piece of toilet paper, which is unraveling from a dispenser
u/loreleievaann / Via reddit.com

3.This boss who told an employee they have 5–10 minutes to respond to emails — oh, and apparently, they only have a five-minute bathroom break, too:

Text conversation about updating chats and maintaining incoming communication timely; mentions need for training on incoming tasks
u/breakitupkid / Via reddit.com

4.This boss who puts piles of work on this employee’s chair EVERY DAY — instead of placing them in the “new to be done” inbox on their desk:

Piles of paperwork on an office chair, which is next to organized an desk
u/walgreensfan / Via reddit.com

5.This boss who swore the office had no cockroaches…even after multiple employees complained:

Several dead cockroaches trapped on a sticky bait board, placed on a wooden floor
u/JoMammasWitness / Via reddit.com

6.This boss’s SON who doesn’t understand boundaries and called at 3:24 a.m.:

A text conversation on a smartphone discussing if the recipient is awake and checking if everything is alright
u/-God_Riddance- / Via reddit.com

7.This boss who responds with “Ok thanks” to everything — including questions:

A phone screen showing text messages about adding a person's profile and a work notice of someone being unable to come in due to not feeling well
u/queriesandqueries123 / Via reddit.com
A text message exchange where one person explains they can't come in to work due to illness, and the other person confirms receipt; another message discusses a new work schedule starting from October 30th with flexible availability
u/queriesandqueries123 / Via reddit.com
Text conversation about adding a person to a Facebook Messenger chat for shift opportunities, with the question repeated due to lack of clarity
u/queriesandqueries123 / Via reddit.com

8.This boss who “cleaned” this employee’s desk (aka, threw everything out, including personal items and client files):

A cluttered office desk with papers, office supplies, and personal items including a coffee cup, tape measure, and a cardboard box filled with documents on the floor
u/BabyYodaTM / Via reddit.com

9.This boss who put this sign up on January 8th:

Sign reads:
u/DeathwatchDave / Via reddit.com

10.This boss who ignored an employee’s time-off request:

A text conversation where one person asks their boxx if they can take Thursday off due to a last-minute event; boss responds,

11.This boss who wants an employee to close in -40 degree weather:

Text conversation about enduring cold weather and the possibility of being locked out. Employer advises on locking procedures and emphasizes the importance of staying available for work
u/Super_Kent155 / Via reddit.com

12.This boss who basically just said, “NAH,” to their employees’ well-being and made this sign:

A poster with various phrases such as
u/WorriedOrchidu / Via reddit.com

13.This boss who doesn’t even care to set reasonable work hours on this job application:

Summary of the text in the job application image: Important points: Location is redacted, it's a six-day work week (Monday to Saturday) with timings from 9:30 am until work concludes; looking forward to having you on board with us!
u/_lakshay / Via reddit.com

14.This former boss who apparently tried robbing his old store:

Tweet by user pj:
u/MiracleEye456 / Via reddit.com

15.This boss who can’t take no for an answer:

Text message exchange:
u/oo-de-lally-golly / Via reddit.com

16.This moving company boss who doesn’t really care about the customer’s furniture:

An overturned office chair on its side amidst cardboard boxes in a warehouse setting
u/Churdlezz / Via reddit.com

17.This boss who didn’t like the color of the chairs in the break room and decided just to get rid of them:

Break room with two round tables, recycling bins, a fire extinguisher, a bulletin board, a copier, and various office supplies

18.This boss who doesn’t care to clarify:

Text conversation discussing scheduling a chat next week, with confirmations back and forth
u/beware_the_noid / Via reddit.com

19.This boss who’s been playing the SAME EXACT playlist every day for the last 6 YEARS:

A tablet showing a Spotify playlist titled
u/KFCCrocs / Via reddit.com

20.This boss who wants 24/7 commitment:

A Quora post from a CEO asking for advice on how to handle employees who leave work at 6 PM, expressing concern over their commitment being limited to work hours

21.And finally, this boss who’s apparently OK with selling spoiled produce:

A gloved hand holds a plastic container of organic strawberries showing signs of mold and decay inside a storage area
u/Kaxton15 / Via reddit.com

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