Some bosses push the limits of patience, others push the limits of common sense, and the worst ones push their employees into illegal territory.
Between sketchy shortcuts and shady schemes that sound like they belong in a courtroom instead of a workplace, there have been plenty of times when superiors told their staff to cross lines that should never have been crossed.
Sometimes framed as “just business,” other times just plain direct orders to act questionably. Either way, these jaw-dropping stories prove that not all bad management is about missing paychecks, sometimes it’s about asking people to break the law.
1
My mom told me her boss preferred employees married to someone with their own insurance. Since they couldn’t ask directly, they’d ask about weekend activities to get people to reveal personal details that might cost them the job.
2
At my old job, they had me Photoshop receipts to overcharge clients. I quit after three months.
3
When I worked at a car dealership, my manager had me use company gas slips to fill up her personal car.
4
I was told to sign kids and mentally disabled people into contracts, even when it was clear they couldn’t legally agree.
5
I managed a bar in Amsterdam that turned out to be a front for laundering drug money.
6
As a teen working at a diner, I found out the owners and bus drivers stole luggage from tourists. I wasn’t asked to take part, but I felt guilty when they were eventually caught after I had already left the job.
7
I refused to fly with a student in 44°C heat because the charts only went up to 40°C. I lost my job over it, and weeks later, there was a fatal accident at the school, unrelated to heat, but tied to other ignored safety warnings.
8
At a healthcare company, I emailed IT about security rules for veteran data. My boss asked me to rescind it for “plausible deniability,” which would have left me responsible in an audit. I refused.
9
My boss asked me to install pirated software on hundreds of computers. When I pushed back, he said I wasn’t liable since he told me to do it. I asked if that logic worked for worse crimes too.
10
At a small company being sued for harassment, the VP threatened all 20 employees not to tell lawyers what we saw. Many of us had witnessed him making inappropriate comments and touching a coworker.
11
As a notary, my boss asked me to notarize documents without giving the required oath. I obviously refused and quit later.
12
A manager told closers not to clock out so he could edit their time later, making them work unpaid hours.
13
I was a bartender when a college team came in, and one player had no ID. I refused to let him stay, but my manager insisted and threatened to “take care of it” if police checked. When I stood my ground, he fired me on the spot.
14
At a fast food place, food older than two days was supposed to be thrown out. Instead, the manager told us to relabel it with a new date.
15
My boss asked me to sell some special medicine to this women of the night agency owner. I refused since it would risk my license.
16
As a nightclub doorman, I was told to let underage students in if their IDs could “pass.”
17
One boss pressured us to vote for his preferred candidate. He didn’t threaten consequences, but those who agreed with him were treated better.
18
While touring with a show, my boss asked me to pose as a customer at a competitor’s business for information. I ignored him and said I didn’t have time.
19
At a retail job, I found out a new hire I trained was making more than me. When I complained, my manager told me discussing wages was against policy. I told him that was illegal.
20
We had to work in the lab even when the water was off. Without running water, we couldn’t wash our hands, use safety showers, or even access bathrooms, but management insisted we keep working anyway.
