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Bosses Open Up About Their Most Heartbreaking Termination Decisions

By Amelia Vazquez
August 8, 2023
Sad mature businessman thinking about problems in living room
Photo by Andrea Piacquadio on Pexels

Firing an employee seems pretty simple, right? They were a crappy worker, so let’s fire them. However, that’s not always the case. These bosses share the most difficult firings they had to do. Content has been edited for clarity.

High School Student

Photo of man scanning a bucket
Photo by Tiger Lily on Pexels

“Several decades ago, we had a high school student who would come to our store every afternoon to work for us. Les was a great employee, hard-working, respectful, and with a wonderful attitude. He took classes at the local vo-tech school in the morning and we trained him further in the afternoon. This routine went on for six months without any problems.

Suddenly, the principal of the vo-tech school called me to say that Les could no longer come to work for us because he missed a school meeting. They terminated his job with us because he missed that meeting.

I already knew what happened. Les missed the meeting because he had to drive his mother to a hospital to get help for addiction. This same teenager would ask for a three-day paycheck so he could spend it on groceries for his younger siblings. I explained what happened to the principal, who assured me it was the decision of the superintendent and the principal of the local school. I contacted the other two men, who assured me that it was someone else’s decision. I drove around to visit all three men, to get them to reinstate Les with us. Eventually, it happened.

A year later, Les graduated and was working for us full-time. I came to work one day to find a note from him, saying he was leaving for Norfolk, VA, a 10-hour drive away. His mom convinced him that he could make twice the wages. When he got there, he also found out it took twice as much money to live.

He had a good head on his shoulders, but he needed some more caring adults in his life. I hope things went better for him, as he got older.”

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Guest’s Complaint

Man in black suit covering his face
Photo by Andrea Piacquadio on Pexels

“When I was in hotel management, many, many moons ago, I had the single worst termination experience ever.

We had hired an older gentleman as a part-time bellman. He was a friendly guy, good with the guests, reliable, etc. About a month after he started, I got a call from a guest, asking that I stop by their room.

I went up, and the guest told me that Bob (not his real name) had done a great job getting their bags up, and seemed like a nice guy, but the guest was rather disgusted by the fact that Bob had seemed to pee his pants while standing there.

I did the usual apology and ‘I’ll find out what’s going on’ bit. Went back downstairs to the front desk. As I walked by Bob, I noticed a large wet spot on the front of his pants. This was at the end of our 3–11 shift. I wasn’t sure about how to approach Bob about the complaint, so I told him it was almost 11, go ahead and take off, planning on discussing it with the hotel GM the next day.

I talked to the GM and he said we would have to let Bob go that day. When Bob came in near 3, I pulled him into the office and closed the door. I told him about the guest’s complaint and asked what happened. He told me he had a little incontinence problem, but that usually it dried quicker.

I told him that was unacceptable in our environment and I had no choice but to let him go. He began tearing up and telling me how hard it was for an old man to get a job. I felt awful! I felt so bad for this poor old guy, who was nothing but a nice guy, but we couldn’t have that incident happen again.”

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Petty Assistant Manager

company, boss, woman
Photo by phmaxiestevez on Pixabay

“When I did retail, I had an excellent employee. She was smart and efficient but had dropped out of school at 15. I made an agreement with her that if she got her GED and enrolled at the local community college I would make her a manager trainee -a year-long program so they knew what to do. Shortly after getting her GED, she was working a closing shift with my Assistant Manager; I did not know this at the time but my A.M. saw her as a threat to her moving forward and was looking to stop that.

What happened was her shoe’s heel broke off so she told the A.M. that she was going to grab a pair off the shelf and would pay for them when the store closed. This was allowed per company policy. Well, she forgot to pay and the A.M. did not remind her.

The next morning, the A.M. called our regional loss prevention guy and reported her for ‘stealing’ the shoes. That afternoon our L.P. guy showed up and told me we had to talk. We had a good relationship since I was good at reducing theft, both internal and external.

He told me the allegation and that she would be fired. The company was very strict due to internal theft issues. But he also mentioned another issue where my assistant knowingly let unpaid merchandise leave the store with an employee.

The employee came in for her shift and as soon as she saw me she told me she forgot to pay and needed to pay for the shoes. As soon as she said that, the L.P. guy walked out of the stock room and her comment was, ‘that hag!’

She knew who made the call. So we went back and did the ‘interview’ where she admitted to breaking policy and as she had told me she was ready to pay. But since she admitted to it I had to fire her, but since it was not a purposeful act, we didn’t call the police.

Before she left, I told her to go see another store and see the Manager I knew in about an hour since he knew she was a great employee and would hire her. I called him with L.P. sitting next to me smiling and nodding as I told him what happened and he would not find a better employee. When she went in she was hired as a manager trainee and now 15 years later is a District manager for that company.

As for the assistant, well after calling in some people to cover shifts, she was called into the back and fired for knowingly allowing the unpaid merchandise to leave the store. Wiped that smirk right off her face.

It bothered both myself and the L.P. person but the policy was well known and posted, but since we both knew this was an honest mistake I was able to insure her firing became an opportunity for her. As for the A.M. about a year later I saw in the paper that she had been arrested for stealing from her new employer and it was a lot more than a pair of shoes.”

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Awkward Talk

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Photo by Aleksey on Pexels

“I brought in an employee that we had many complaints on. His body odor was so offensive that no one else could work near him. He didn’t look particularly dirty, but he smelled awful. Like week-old rotting garbage awful.

Asked him to sit down, and I explained the problem. I told him he had to get his body odor under control, or I’d have to terminate him. Suggested he see a doctor if he thought that would help (we had terrific health insurance, so it would have cost him $5.00 to go.) Offered him a paid day off to do so.

If I could have figured out a way, I would have avoided the entire issue, but there was no way around it.

He immediately declined. (Don’t know if it was embarrassment, or stubbornness, or what.)

I explained again that if he declined I’d have to fire him. He understood and told me that was my only choice, so I let him go. I did not challenge his application for unemployment a couple of weeks later.

It was the most uncomfortable employee situation I ever experienced, worse even than the employee I fired, and had been arrested at the same time for stealing.”

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