New boss removes flexible working with "no exceptions" preventing employee from attending their cousin's wedding, employee takes all 23 days of their leave at the end of the quarter instead forcing their boss to cover for them: 'Two people quit'

Author image for Brad Dickson
Brad Dickson • Managing Editor
May 10, 2025 12:00 PM EDT

New managers come in hot, looking to make a splash, saying more than they're actually doing and disrupting the process and causing inefficiency, all while loudly proclaiming that they're doing the opposite. 

The problem is that the policy they heard in an unsubstantiated "self-help" audiobook doesn't have any application in a real-world setting, certainly without asking questions first and making exceptions where necessary. The thing is, their lack of experience and obsessive focus on "making change" blinds them to the folly of their own logic.

And so, despite their loud declarations about "efficiency," "streamlining," and "consistency," the numbers don't lie—metrics stall out and begin to decline, deadlines are missed, clients are unsatisfied, morale dips before burnout, and turnover begins to rise, draining essential and historical knowledge of the organization. 

The reality is that any inflexible policy is never a good idea. Flexibility begets creativity and innovation, whereas inflexibility is confining and authoritarian.

That's why when this worker was faced with missing their cousin's wedding, they decided to just take all their leave at once at the end of the quarter, forcing their boss to cover for them and causing far more disruption than their would have been if they had been allowed to keep their former working arrangement.

Advertisement
  • 01
    Cheezburger Image 10503566336
    via Natalia Blauth

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

  • 02

    "HR said, 'We can’t make exceptions' so I took all my PTO at once"

    New manager comes in loud, talking about "structure" and "consistency". Suddenly no WFH, no flex hours, no swapping PTO. I asked to move two days. My cousin's wedding, she just goes, "Sorry, we can't make exceptions to anyone. It wouldn't be fair" Alright then, I put in a request for all 23. of my unused PTO days. Straight through end of quarter. No overlap, no coverage. It got approved in like...10 minutes? Lol okay. Couple days later she's in full panic mode:
    via StardustFrost
  • 03
    "Wait who's handling your workload?" "Dunno. I assumed you had a plan. No exceptions right?" She had to cover me and deal with fallout. Stuff piled up, clients got pissy, two people quit. I came back to a new HR memo: "Managers can now approve flexible PTO on a case by case basis." Turns out fair looks different when you're the one getting screwed.
    via StardustFrost
  • 04
    Cheezburger Image 10503566592
    via Natalia Blauth

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

  • 05

    Readers shared some great stories of their own in the comments

    JustSomeGuy_56 .7h ago I worked at a company that shut down the manufacturing line for 2 weeks every August. All hourly employees were required to take their vacation during that period whether they were part of the manufacturing process or not. One guy wanted to take his vacation at the end of May so he could attend his daughter's graduation from college. Request denied.
    via StardustFrost
  • 06
    His boss send a memo to HR stating that because of the particular project this guy was working on, it was absolutely vital that he be at work during the two week shutdown. He should be forced to take his vacation at a time that was more convenient for the company, like the end of May. So ordered.
    via StardustFrost
  • 07
    DataDud... . • 5h ago Edited 2h ago I used to work for a major international bank where vacation was set to expire after 22 months. This meant that any vacation earned in 2025 would expire at the end of October 2026. The issue with this? October is fiscal year and and usually an all hands on deck situation where a ton of critical reports need to go out to meet regulatory compliance.
    via StardustFrost
  • 08
    Anyway my middle manager job was usually insanely busy so I rarely took my vacation and it was always a struggle to get my allotment in during the time. before it expired. One year I had three weeks left and it was early October so I approached my boss and asked if I could book the days now and show up to work for October and then just take the actual days off in November when it was calmer. He said no exceptions, use it or lose it (thinking I would opt to lose it)
    via StardustFrost
  • 09
    I immediately went to the HR system and booked my three weeks vacation for the last three weeks of October and it gets approved On the second day of my vacation he started e-mailing me with things like "we need this report run and verified by END OF DAY" even though I had my out of office set. I'm not a j about it so I took it as a one off and just ran it and checked it over as it took me about an hour to do, no harm.
    via StardustFrost
  • 10
    Then he did that the next morning, and evening and the one after that and after that. I e-mailed him back and copied HR asking if this meant my. vacation days would get refunded, or if the company was paying out OT hours for this work since I was on approved leave. I didn't hear anything for about 48 hours and then got a sheepish "enjoy the rest of your vacation we have this handled" response. Apparently HR tore an absolute strip out of him for harassing and demanding work from an employee on va
    via StardustFrost
  • 11
    When I got back he said moving forward he would be amenable to some vacation day swaps to make sure we have appropriate coverage at the right times of the year [edit] I should add HR were kind so I don't think they of cared all that much he was asking me to work on my time off, I think they sh their pants that he was demanding it in writing with a long history/audit trail.
    via StardustFrost
  • 12
    whatsit50 6h ago • When my wife and I were getting married, she had invited one of her coworkers. They both put in PTO requests. Her boss said that they could only approve her coworkers request because they need coverage and she had more seniority even though both requests were for our wedding, meaning if my wife couldn't get the time off, her coworker wouldn't be going obviously The coworker removed her request, called out sick and then They both ended up going to a different company leaving th
    via StardustFrost
  • 13
    avid-learner-bot 7h ago . I mean, sure, HR policies are there for a reason, but sometimes you gotta wonder if they're written by someone who's never had to actually manage a team, sounds like your manager found out the hard way.
    via StardustFrost
  • 14
    Business-Idea1138 7h ago • I hope you used part of those 23 days to send out job applications. that place. F
    via StardustFrost

Want More? Follow Us and Add Us as a Preferred Source on Google.

Tags

workplace discussion workplace-stories jobs employee job malicious compliance work workplace workplace malicious compliance employment in the workplace
Scroll Down For The Next Article