15 Bosses who regretted firing their best employees: 'He won't sign it... fire him'

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Jan 7, 2026 3:00 PM EST

These bosses were pretty sure that they made the right choice when firing their best employees, but that doesn't mean they don't have regrets about it. 

No one is perfect, even when they're trying to a professionals in the workplace. Even the best employee in the world will have a flaw or 2. Maybe that worker is great with coworkers, but their hot temper makes them a risk when they're talking with customers. Maybe the worker is very technically skilled, but has such poor communication skills that their coworkers despise them. And sometimes that worker isn't even necessarily flawed — they just make a huge mistake that ends their career on the spot. 

Whatever the reason may be, these bosses had to fire some of their A-team workers, and they weren't happy to see them go. One manager shared a funny story in which they had to say sayonara to a worker who was caught by a secret shopper. What was he caught doing, you ask? Ah, well, he was digging for gold in his nose, as the secret shopper claimed. The employee ardently refuted that claim — he refused to sign any write-ups about the supposed incident.  Since he wouldn't sign it, he was let go. What would you do in that situation? Would you admit to doing something humiliating that you didn't even do if it meant keeping your job? It's hard to say… but it depends on how much you value your dignity, I suppose. There are always better jobs out there — you just need the right push to start looking. 

One surprising story isn't so funny. One person shared that in 2008, they had to watch as 100 people got laid off on the same day. They described the workplace as a "ghost town" after the HR dude had laid everybody off. Then, in a cruel twist of fate, the very same HR person got fired himself. What a terrible day for all involved! I can't imagine the feeling of firing numerous people in the company that you care about. However, subsequently getting fired might even the playing field a little bit… not that it's any consolation to the HR person himself. 

Keep scrolling below to check out a bunch of intriguing stories from the bosses who were bold enough to tell their tales. 

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  • 01

    'Bosses of reddit, have you ever seriously regretted firing someone, and if so why?'

    Woman in long tan coat holds cardboard box while walking through dimly lit office
    via Getty Images For Unsplash+

    The image does not depict the actual subjects of the story. Subjects are models.

  • 02
    punkwalrus I had an assistant for about a year, who was a pretty good assistant for a difficult working situation. My boss, the district manager, hated him, though. She kept trying to catch him screwing up when I wasn't around. The trouble was, the company paid poorly, so talent was hard to come by, training was difficult, and the hours were 48 a week MINIMUM.
    via u/punkwalrus
  • 03
    This guy was the only assistant I had who didn't quit in less than a year. My stores were so undermanned, if this guy left, I'd be working 80 hour weeks like before I got him. They only reason it wasn't more than 80 hours was because the stores' malls or shopping centers actually closed at night.
    via u/punkwalrus
  • 04
    Finally, one day, she wrote him up because she said "a secret shopper" said he was picking his nose. This guy, who at least had SOME dignity, refused to sign the disciplinary paperwork. "I want proof: I am not sitting in the showroom, picking my nose." My boss said, "he won't sign it, insubordination. Fire him." I
    via u/punkwalrus
  • 05
    really tried to reason with her, but she wanted him gone one way or another. "Ether you fire him, or I'll come in and fire both of you." I had to fire a man for picking his nose. I quit shortly after that, because I knew this was just the lowest I had ever sunk in management. I still feel bad about all that.
    via u/punkwalrus
  • 06
    somewhat_random Years ago I got a call from a competing engineering company. They screwed up a job and rather than own up, decided to blame a senior technologist as the scapegoat. His immediate boss was against it but the partners demanded it. He phoned us and said "you should hire this guy". We did and he was an excellent employee until he retired 20
    via u/somewhat_random
  • 07
    years later. Our gain, their loss. The best part is that the guy who called me (who was a senior engineer) quit shortly thereafter and the company closed down a couple years later Karma I guess. -
    via u/somewhat_random
  • 08
    AdUnfair3836 Someone else hired someone with no experience after I voted "no". I knew he would be in over his head and he had a good job already. They didn't train him or coach him. And then after about 6 months my bosses boss come to me and tells me to build a case against him... my team member... and to fire him.
    via u/AdUnfair3836
  • 09
    I quit within the next two months. F them... I'm not doing their dirty work to solve a problem they caused and enable them to keep their hands clean in the process.
    via u/AdUnfair3836
  • 10
    absentmindedjwc The other side of the coin here - but I'm sure they regretted getting rid of me. I was an individual contributor at a fairly large organization that one day was pulled into that dreaded meeting with some random director and someone from HR. I come to find out that I'm being laid off effective immediately. They walk me
    via u/absentmindedjwc
  • 11
    to my desk, I gather my things, and I'm walked out of the building. A couple months go by and they realize that shit randomly stopped working. They narrowed it down to something I had worked on.. this was costing them a fuck-ton of money, so they reached out to me (that is: a flurry of emails and a few phone calls before I was
    via u/absentmindedjwc
  • 12
    able to answer) asking for an explanation. Like.. "my guy, I don't know why slot's not working, I haven't worked there for a few months..." After telling them that I'll meet with the relevant teams and help figure it out for double my normal hourly rate (with a minimum of two weeks), I got to work. After hearing the issue, it became pretty obvious that some
    via u/absentmindedjwc
  • 13
    automation scripts I wrote weren't running anymore. I asked about it, and it turns out that another person that I collaborated with to set those scripts up also got cut, so the resource allocation for the server was just left to expire. I kept a backup in my account, so I told them that if they just access my backups, they should find it in there... they shouldn't be terribly difficult to implement.
    via u/absentmindedjwc
  • 14
    Well.. it turns out that they deleted my shit after about a month.. so it was gone. Yeah, good luck with that. That shit took me a while to put together and get just right. You're going to have to cobble something together to get it to work... here's a rough idea of what you need to do to sorta get stuff running. Now pay me, kthx. Fucking idiots.
    via u/absentmindedjwc
  • 15
    Chairboy It sucked, but it was the correct thing to do. Dude was a good guy, a chill guy, but he was chill to the point of not doing the work and it created extra work and pressure for everyone else.
    via u/Chairboy
  • 16
    Counseled him, tried to break down the tasks he had and figure out how to get him up to snuff but it was like he'd just lost interest in doing the work and was waiting out a clock.
    via u/Chairboy
  • 17
    Finally, I had to put him on a PIP which suuuucked. It had a specific outline of stuff he had to do, it was like a guidebook for how to keep his job because I wanted him to be successful because we'd worked together before doing different work and I knew he was a good guy, but it was like he just checked out.
    via u/Chairboy
  • 18
    Finally, I had to fly up to his office and escort him to Human Resources for The Meeting. It fucking SUCKED. It was 20 years ago and I still think about it sometimes because it was just so goddamn avoidable. All he had to do was show up and meet his commitments and
    via u/Chairboy
  • 19
    his commitments were low key and exactly what he'd signed up for when he applied to the position. He drifted into his next job and we lost touch, I hope he's ok. FUCK. I'm still upset by it because I've been laid off and it's just so goddamn awful.
    via u/Chairboy
  • 20
    geekhalla Abput 20 years ago I was running a bar Christmas eve - chaotic night as we were incredibly short staffed due to jeavy snow and aot of our workers being from a different area. Bar downstairs was closing up and staff being moved to the ub upstairs. We were £200 short in the bar and the main manager
    via u/geekhalla
  • 21
    interrogated three out of the four - conveniently not the supervisor he was having an affair with. That supervisor was also in charge of the float and was generally shit at her job. That float for one till was conveniently £200. Main boss wouldn't consider his fling could do wrong (a common occurrence) and he didn't want to deal with it.
    via u/geekhalla
  • 22
    So it became me (lowest of four managers) to sack three people for suspected theft. On Christmas eve knowing I wasn't in any position financially or in terms of job security to say no. Only joy was that his wife finally caught him I the affair and his whole life went to shit soon after :)
    via u/geekhalla
  • 23
    backyardvegas I had to fire someone on my actual last day once. And right beforehand, everyone was making a joke about the person I fired getting fired. That sucked. Not a good vibes last day at all.
    via u/backyardvegas
  • 24
    Keyspam102 I was forced to fire a junior person on my team, my boss gave me no choice, because she had used a competitor idea as inspiration (working. in design). But it was our intermediary boss who told. her to use the idea. I wish I would have taken a harder stand but I was afraid of being fired myself, I was only
    via u/Keyspam102
  • 25
    a few months on the job. I still regret it to this day but the other woman has had a good career so that's a plus at least.
    via u/Keyspam102
  • 26
    Anneisab In 2008 my company had a D Day. It was pre-planned. Random Tuesday we came in like normal and 100 people were laid off. I worked the late shift so at 6pm the damage was done, everyone was out the door and it was like a ghost town.
    via u/Anneisab****
  • 27
    I walked past the HR guy who did all the firing. He was sitting on the open stairway in the front lobby silently crying. I was so angry at everyone being let go I never thought about the HR team stuck in the middle. They fired him the next day.
    via u/Anneisab****
  • 28
    themeCh10 I've never regretted it as there was always a good reason but I can honestly say it's not fun and every time I knew I was gonna have to fire someone the night before I was never able to sleep. But in the end it's usually a relief, but at my company it's pretty hard to actually get fired so when you do have to do it, it's almost never out of the blue
    via u/themeCh10
  • 29
    ycelpt I wouldn't say I regretted firing then, but I have been unhappy to have to fire some people. There are people out there who are genuinely nice people but they are just a massive liability at their job. One guy was lovely, he'd do anything you asked and was a fairly quick learner. He was hired as a trainee chef and was
    via u/ycelpt
  • 30
    still on his probation period. We had to let him go for not washing his hands after touching raw chicken etc. He'd been caught and disciplined on it a few times already. We had a busy day lined up (mother's day, one of our busiest in the year) as he was pre prepping veg for it so it could be steamed up and served. He was called to assist with the lunch rush and he never washed his
    via u/ycelpt
  • 31
    hands after handling raw chicken and went back to prepping. Head chef who'd caught him before came in after a little while to see him on veg and asked when he last washed his hands. Said he didn't know. Other chef went mad because he'd literally just told him to wash them after lunch rush but couldn't (and shouldn't have to) supervise that he did it.
    via u/ycelpt
  • 32
    Since they couldn't identify which had been done before or after he touched chicken it all had to be binned. Some 100+ portions of potatoes, kale, carrots and broccoli etc all had to be binned an re bought last minute on Saturday afternoon. We had to sack him after that and the chefs had to stay late to prep for the next day.
    via u/ycelpt
  • 33
    Sukaruuma I've only ever had one guy fired at a small company I worked for. I was the lead semi driver, and most of the day to day stuff fell to me to figure out if we had any issues. Well we had one guy (who's name for the life of me I cannot remember) who we hired on and within 2 weeks of him starting we had issues with him being on time to our meet points
    via u/Sukaruuma
  • 34
    and that was the 1st red flag because no one else had had any trouble being on time before in clear weather. The 2nd red flag was being. told by one of our other drivers and a driver from the other company we interacted with daily that he'd gotten into a heated argument with one of them.
    via u/Sukaruuma
  • 35
    The 3rd and final red flag was when he decided that me telling him to stop pushing a piece of equipment so I could line it up was a reason to have a confrontation with me, his direct supervisor. After that, I called the owner and told
    via u/Sukaruuma
  • 36
    them he needed to go before he progressed into a physical altercation with someone. They agreed and he was let go after he returned at the end of his shift.
    via u/Sukaruuma
  • 37
    yodelingbeagles Laying off good people is the worst. Cry every time. That's different than firing though.
    via u/yodelingbeagles
  • 38
    AlwaysNipping Sometimes it takes up to 6 months to actually fire someone. If I've gone through the painful process that entire time, then the person doesn't deserve to have a job. As a "boss" you're typically required to give NUMEROUS chances,
    via u/AlwaysNipping
  • 39
    along with tons of monitoring, coaching and documenting. The whole process sucks and so does the person I'm firing for making me go through all of that crap and never improving their performance.
    via u/AlwaysNipping
  • 40
    msjammies73 The whole process took about 9 months and it was the right choice for sure. But the day they finally told me that this person would be officially terminated was the day my company and pretty. much everyone else in our industry announced they were ceasing work due to Covid lockdowns.
    via u/msjammies73
  • 41
    I literally begged HR to postpone the termination; they said it was impossible and they wouldn't budge. I did get them to add an extra month of severance including health insurance. which I hope helped a bit. I didn't regret the termination but the timing really haunted me for a while.
    via u/msjammies73

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