IT guy gives boss ultimatum after his PTO request was put on hold until he trained his potential replacement: 'Approve my 1-week PTO or accept my 2-week notice'

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Ben Weiss • Writer and Editor
Aug 8, 2024 8:00 AM EDT

It's not uncommon to have to get your PTO requests approved by one's manager; however, it is uncommon to have that vacation request held hostage from you until you teach a nepo baby everything you know.

Here, we've got an IT guy who reported to the Chief Admin at his company, an individual who was clearly well-connected with the higher-ups at the company. This guy was an expert in his field, and everyone in the office was so dependent on his expertise that it made taking time off extremely difficult. So when he put in his request for just one week of vacation, he was met with immediate resistance from the Chief Admin. He decided to withhold the employee's vacation until he agreed to train a new nepo baby at the company, who was clearly a candidate for his ultimate replacement. Of course, one cannot teach a novice decades worth of IT expertise, a fact that the Redditor tried to relay to the Chief Admin to no avail.

Keep scrolling below for the full story and for the best reactions from folks in the comments section. For more, check out this post about a coworker's iconic company-wide resignation email.

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  • 01
    "Boss asked me to train him before I go on vacation"
    via Paymo
  • 02
    I've been working as an Information Systems Manager for a small company with around 45 employees for the past 12 years.
    via StormShadowJoe
  • 03
    Although I've requested promotions and pay raises every year, they've been consistently declined. My responsibilities are extensive, including major decision-making in information technology, software projects, implementations, cybersecurity, audits, compliance, network and firewall management, IT assets,
    via StormShadowJoe
  • 04
    and so on. While most of our general help desk issues are outsourced to a service provider, I do assist with them when I can, depending on their complexity, so we don't always have to outsource typical IT work if it's not necessary.
    via StormShadowJoe
  • 05
    Recently, the company underwent structural changes, and I began reporting to the Chief Admin. Interestingly, the Chief Admin, who was hired at the same time as me, quickly climbed the ranks within the company. Anyway, a couple weeks ago, I submitted a request for a 1-week time off, which required his approval. He
    via StormShadowJoe
  • 06
    responded that he couldn't approve my time off until we figured out coverage details for my absence. In all my 12 years, this is the first time they are worried about coverage.
    via StormShadowJoe
  • 07
    He asked me to document all my responsibilities and create a knowledge base, then train him on how to do my job. This would include fixing common computer and network issues, resolving malware/virus problems, connecting to servers, handling SaaS and application issues, dealing with cybersecurity, network configs, etc.
    via StormShadowJoe
  • 08
    Taken aback, I told him that teaching him a decade's worth of IT knowledge wasn't feasible. He insisted, pointing out that I was self-taught, so I should be able to teach him. I tried to explain that IT doesn't work that way, suggesting instead that he contact our service provider in case of an IT emergency. And if it's not urgent,
    via StormShadowJoe
  • 09
    they can leave it and I can return to fix it. He countered that the service providers take too long to respond and insisted I train him or someone else. I continued to object, detailing the complexities involved in IT duties, but he persisted, saying, "We don't need to be trained on everything; we only need to know if something goes wrong, how do we fix it?"
    via StormShadowJoe
  • 10
    Frustrated, I finally agreed to see what I could do, to which he responded, "Great, I'll sign off on your PTO once our training is done."
    via StormShadowJoe
  • 11
    An hour later, I returned to his office with a 2-week notice, placed it on his desk, and walked out.
    via StormShadowJoe
  • 12
    The following day, I was called into a meeting with the Chief Admin and the CEO to discuss this "matter." During the meeting, I learned that the CEO and CAO are cousins, seems clear whose side the CEO was on at that point. They did all the talking, and I simply presented two options: approve my 1-week PTO or accept my 2- week notice. I then excused myself from the meeting.
    via StormShadowJoe
  • 13
    It's now three days closer to my scheduled PTO, and I have yet to hear a decision from them on either option. I'm not playing their stupid games. I think I'll just quit.
    via StormShadowJoe
  • 14
    EthereumFuture 21 hr. ago When you leave, dont forget to point out that since you were self- taught, he should be able to self teach it himself in no time
    via StormShadowJoe
  • 15
    dubiousN 11 hr. ago More like the "Chief Admin" should know already this
    via StormShadowJoe
  • 16
    7dayweekendgirl. 22 hr. ago Good idea. Then when they call desperate for help, charge them $500 per hour as a contractor.
    via StormShadowJoe
  • 17
    Mtndrums 21 hr. ago Paid in 8 hour blocks in advance.
    via StormShadowJoe
  • 18
    Eladiun - 21 hr. ago Honestly no raise or promotion for 12 years in IT. It's about time you stopped being their whipping boy.
    via StormShadowJoe
  • 19
    You missed out 30 to 50 grand in comp increases easily if you had jumped around every 2.5 years
    via StormShadowJoe
  • 20
    dsdvbguutres 20 hr. ago You're probably too good at your job, you're making it look easy. Boss thinks you're not doing anything. Offer your boss to shadow you for a day and bring a notebook to take notes.
    via StormShadowJoe
  • 21
    Boss will be frustrated with having to do actual work and get distracted by the next shiny object in about 15 minutes anyway.
    via StormShadowJoe
  • 22
    Ima-Bott 21 hr. ago Don't quit. Take your PTO and enjoy it. (Take irreplaceable desk trinkets). Show back up for work and start job hunting on their dime.
    via StormShadowJoe

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