'Approve my 1-week PTO or accept my 2-week notice': Boss denies IT employee's vacation request until he trains the new hire on a decade worth of experience, employee refuses and submits his resignation instead

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Ben Weiss • Writer and Editor
Aug 18, 2025 8:00 AM EDT

There better be a good reason why a boss would deny an employee's rightfully earned PTO request. After all, vacation time is an essential benefit of employment. Managers should not have any say as to when it's convenient for them to allow employees to utilize their own much-deserved entitlements. 

Of course, some employment contracts include malleable language regarding the approval process of a PTO request. Let's all acknowledge the truth that this kind of vague language is never used in favor of the employee; rather, it's always management and the company at large that are protected by language such as that. 

As for this employee, he had been working as the go-to individual in the company's makeshift IT department for over a decade. When he submitted a vacation request for a week off, his new boss suddenly took the opportunity to create conflict over it. The boss not only rejected the request outright, but then he insisted that the employee train a new hire regarding his decade-spanning knowledge of IT and then he just might get that vacation request approved.

Naturally, this was not what the employee wanted to hear nor was this a feasible task for one person to teach on top of his long list of currents responsibilities on the job. Despite numerous efforts to explain why this was unfair, the author's boss would not relent. So, the employee left his office and returned with the only thing that made sense: his resignation.

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  • "Boss asked me to train him before I go on vacation"

    A person wearing a blue button down shirt and black pants hands a piece of paper over a desk to an unseen person that reads "RESIGNATION."
    via Unsplash+ (Getty Images)

    Image is representative only and does not depict the actual subjects of the story.

  • The fact that the author's boss refused to listen and understand why his request was so outlandish communicated everything to the author that he needed to know. Sure, it was just one PTO request, but it was bigger than the concept of vacation. This guy was unwilling to accept the perspective of his most talented employee simply because the employee was telling his boss something he didn't necessarily want to hear. At the end of the day, that's not someone worth working for.

  • I've been working as an Information Systems Manager for a small company with around 45 employees for the past 12 years. 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,
    via StormShadowJoe
  • implementations, cybersecurity, audits, compliance, network and firewall management, IT assets, 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
  • 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.
    via StormShadowJoe
  • Anyway, a couple weeks ago, I submitted a request for a 1-week time off, which required his approval. He 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
  • 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
  • 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,
    via StormShadowJoe
  • suggesting instead that he contact our service provider in case of an IT emergency. And if it's not urgent, 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
    via StormShadowJoe
  • 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
  • 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
  • An hour later, I returned to his office with a 2-week notice, placed it on his desk, and walked out.
    via StormShadowJoe
  • A man wearing a white button-down shirt and a blazer carries a cardboard box full of items.
    via Unsplash+ (Curated Lifestyle)

    Image is representative only and does not depict the actual subjects of the story.

  • 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
  • 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
  • UPDATE|18.9.23 I visited the CEO's office this morning to inquire about the decision on my PTO request. The CEO informed me that my request has been approved and that there's no need for me to train anyone. Should any technical issues arise, they'll reach out to our service providers
    via StormShadowJoe
  • or vendors. He encouraged me to enjoy my time off without any interruptions. However, his tone and facial expression suggested that there might be something more. So, I directly asked, "Is there anything you need from me?" He replied, "No, not at this
    via StormShadowJoe
  • time. When you return, I'd like you to spend about an hour a day training the CAO, so he can be better prepared to cover for you in the future." I knew it! I knew they were still expecting me to train him in some way.
    via StormShadowJoe
  • I've formulated my plan now and want to thank all those who provided insightful advice. It reassured me that leaving this job won't be a mistake. Here's my course of action: I'll take my PTO,
    via StormShadowJoe
  • then return to train the CAO an hour a day, doing so in a manner that will be entertaining for me. I'll delve into highly technical explanations, use specific terminology, and focus on command prompts rather than the UI. I'll make the training so intense that he might even consider quitting himself. That's my plan.
    via StormShadowJoe
  • I've already applied for other positions about a week ago, and an interview could be on the horizon. I'm hopeful that I'll secure a new job by the time I return. Once back, I'll not only train the CAO but also submit my final notice on the same day,
    via StormShadowJoe
  • turning the next two weeks into an IT bootcamp for him. He'll get the crash course he asked for, and I intend to make it the most overwhelming experience he ever had. I'm certain even after all that training, not everything will be covered in its entirety, but that's not my responsibility anymore. I
    via StormShadowJoe
  • will not be returning to assist them in any way or form once I leave. I appreciate all the support and feedback. Your understanding of my situation and the varied solutions offered have been immensely helpful.
    via StormShadowJoe

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workplace-stories employee work stories toxic-workplace job work i quit satisfying quitting story PTO overworked-employees Horrible Bosses company quitting toxic-work-environment
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