Work can be a bummer and it can also be unpredictable, and much of that depends on the people leading the way. A good boss can make challenges feel manageable, while a bad one can make even the simplest task feel like climbing uphill.
Leadership isn’t just about having authority and micro managing employees, it’s about responsibility, judgment, and being able to follow-through. Most importantly, being there when you’re needed, but sometimes, those in charge stumble in ways that leave everyone else picking up the pieces.
The result are real situations where bosses completely dropped the ball. These stories serve as reminders that while no boss is perfect, some mistakes are too bad to overlook them.
1
Whenever my boss started with “Going forward…” we knew it meant we were about to take the blame for something they forgot to communicate. Instead of owning the mistake, they’d throw the team under the bus with vague process changes, while telling their bo
2
We were playing basketball at the park when my boss lost his temper and punched a coworker in the face.
3
My boss once hid in the bushes outside the facility at 4 a.m. with the maintenance guy, spying through windows to “make sure” we were working during downtime hours.
4
One day the boss showed us the company books. Turned out every past employee had either been laid off or forced to absorb extra work. Meanwhile, he sat back doing very little and pulled in $120,000 a year, four times anyone else’s salary.
5
I worked for an attorney who constantly missed filing deadlines. I’d prepare the pleadings, he’d take them to “review,” and despite my reminders, he’d let the statute of limitations expire again and again. A lot of clients paid the price for his negligenc
6
My boss once called his wife by another woman’s name. Turned out he was cheating. Since his wife was actually the CEO, he lost his job fast.
7
I worked at an ice cream stand run by a boss who didn’t understand ordering. He’d just put “5” for everything on the order sheet, five tubs of every flavor, five packs of every topping, no matter the size. We’d run out of popular items fast, while stockpi
8
A manager once emailed a supervisor recommending that an employee be fired, but accidentally CC’d the very employee (and several others).
9
A manager got promoted and suddenly thought she was a leadership guru after reading a business book. She hired someone to run an all-day Saturday seminar, then made attendance mandatory. On the seminar day, she gave a quick pep talk, then left, saying wee
10
At one company, the CIO sideswiped a woman’s car in the parking lot. The woman stood by her car to assess the damage, but the CIO just walked right past her without saying a word, even though there were plenty of witnesses.
11
My boss was supposed to fire someone but dragged his feet for three weeks. During that time, the employee messed up payroll badly. I finally fired her myself, even though I didn’t technically have the authority. I’d only been in the job three months. The
12
I was fired because my boss thought I was late, when really the assistant manager gave me the wrong start time. To make things worse, schedules were often posted just hours before the new week started, so we constantly had to call in.
13
When my boss took over a department, he decided to cut all contractors, no matter how long they’d been there. A month later, critical systems failed, and no one left knew how to fix them, because he’d fired the experts.
14
One boss gave “Employee of the Month” to someone who was constantly a problem, hoping it would inspire her. Instead, she doubled down on her bad behavior and became an even worse teammate.
15
The VP once told me I was being disrespectful. When I asked how, she said, “You know what you’re doing.” I asked again, genuinely confused, and she replied, “I don’t have time for this.”
16
At my dad’s new job, his boss ignored his warning about unstable ground while building a wall. She insisted it’d be fine. When the nearly finished wall collapsed, she blamed him.
