To keep it short, I have a manager that is very nit-picky about when and how long I take my vacation time. My vacation time at my company works on an accrual basis, so I earn X amount of days per year that I must use by the end of the year, or they will be lost.

A few times now (not all), I've put in requests which leads my manager to having a conversation with me telling me "no". I put these requests with a reasonable timeline that they could be responded too, at least 2 weeks, and upwards of a few months. There isn't a very good reason why I can't take off, other than "the company is trying to meet deadlines, and we need you here to work". Here's the problem, I know what deadlines the company is under, and I have work around these deadlines yes, but there are no specific deadline dates within my requested time off, nor will my absence during these days prevent me from meeting the actual deadlines. In other words, I have plenty of time to do my work before the real deadline.

I think the real reason for his hesitancy is that his manager has given him grief before about letting too many people take time off during critical periods of work/deadlines. He has said this on a number of times as his reasoning.

How can I convince my manager to approve my time off requests, where I feel I can take this time without affecting company deadlines?

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Masked Man
    Jul 3, 2018 at 13:09
  • The company's inability to meet deadlines is a problem for the company, nor for Jay. So is their one-bus policy on Jay. I hope that you don't get sick.
    – dotancohen
    Jul 4, 2018 at 8:40

8 Answers 8


You are entitled to take your holidays, so the issue is with coming to an acceptable timeframe for your holidays.

If the manager will not give you time off, try asking him to provide you with dates where he will approve days off.

If this doesn't lead to an acceptable answer, try asking for money in lieu of leave. Odds are that this won't be accepted, but the objective is that you are forcing the manager to provide you with days off.

Either way, I would consider polishing the CV and preparing to move on to somewhere which is better organised.

  • Comments are not for extended discussion; this conversation has been moved to chat.
    – Masked Man
    Jul 3, 2018 at 8:30
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    Before switching companies OP could try moving within also. To me the following part may even be developped a bit : to move on to somewhere which is better organised. Because from what I see in OP post, manager is wasting holidays of his stff because of hiw own lack of skill.
    – Walfrat
    Jul 3, 2018 at 11:34
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    Depending on local laws, you cannot trade holidays for money. In my local case, half of the holidays has to be taken by force of law. Jul 3, 2018 at 14:31
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    One thing worth considering....don't offer money in exchange for PTO unless you actually want that outcome. I've worked at places where they would gladly pay you for your PTO, and it did sort of establish that they could reject a bunch of your requests because, hey, they'll just pay you.
    – Rob P.
    Jul 3, 2018 at 16:30
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    This is for the US. Your employer is not required to grant you any vacation time, although most full-time employers do because otherwise they'd have a very difficult time recruiting anyone; you can be required to work on national holidays, although you're supposed to get "compensatory time"; and there's no law which says an employer has to let you take vacation that you've earned. And the employer is under no obligation to compensate you for untaken vacation. This is known as "freedom". Whose freedom is being referred to is an open question. Jul 3, 2018 at 23:19

When you request PTO, do so in writing (Email or other traceable form of communication).

When your boss invariably comes up to verbally deny your PTO request, tell them you need a response in the same media you requested in (this is to get a traceable record). This can be supplemented with prompts (such as follow up emails etc.) if they refuse to respond in a way that gives you a record. Either a list of denials or a failure to respond to your initial request will build a paper trail that you can use to protect yourself and your interests. NOTE: Do not use this as a way to threaten or bully your boss, this is merely an intelligent way to cover for yourself.

As has been suggested, any denials should be met with a "When is an acceptable time period for me to take my PTO?". I would not offer to take pay in lieu of PTO, as PTO is not only a form of compensation (equivalent to being paid for attending x hours), it is also a critical component of work-life balance. If your boss is unwilling to provide you with time you can take PTO in, gently remind them that the PTO is a form of compensation, and you have earned it via company policy.

I'm sorry So-And-So, but my PTO is a benefit I have earned through my time working here, and I intend to take it so that I may avoid burnout/stress/personal problems that can be caused by overwork. I would ask again that you either approve the dates I have asked for, or provide me a suitable time period for me to use my PTO in.

It is unlikely for you to be able to guess what your boss' motivation is behind denying your PTO requests, so rather than guessing at it, you should ask them in a non-confrontational manner. This may lead to a civil discussion that can result in an acceptable compromise. As per OP's update to the question, the reason is know, and this is likely not a viable course of action as a result.

As a last resort, if your boss is completely non-cooperative, you can take whatever traceable form of request/denial you have and submit your PTO request through HR, attaching the documentation as proof that you have attempted to go through proper channels. This last tactic will cost you your relationship with your boss, and will most likely put you on the short list to getting fired. I would only take this approach if you already have another job lined up.

  • Not to mention that eg. in most European countries, PTO is required by law. If a company would prevent an employee from taking the accrued vacation, they would get into legal trouble. Jul 3, 2018 at 13:58
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    @JuhaUntinen unfortunately in the US (the poster's location) we have no such protections. Companies aren't required to even give PTO, let alone allow employees to use any accrued PTO. Nor are they required (at a federal level) to pay out unused accrued PTO.
    – alroc
    Jul 3, 2018 at 17:58
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    @alroc there are no legal requirements to provide PTO, but contractually guaranteed PTO is enforceable unless the employer includes a clause, and even then a court my hold that the clause is invalid. The reason for this is that PTO has intrinsic value, and as such can have an actual value tied to it for a breech of contract suit.
    – GOATNine
    Jul 3, 2018 at 18:04
  • @GOATNine I've never worked someplace that had a contract or even written policy that said "you will be allowed to use all of your PTO in a given year." Only that you'll accrue the PTO - never an assurance that you can use it.
    – alroc
    Jul 3, 2018 at 19:28
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    @alroc Again, if an accrual system is written into the contract, it's enforceable. I don't know how else to phrase this, you WILL win a court case over it, but it's usually not worth the time and loss of your job (they WILL find a way to terminate you). A paper trail usually leads to them caving in without you even having to threaten suit, HR exists to protect the company, and if they think they'll lose a court case, they will take measures to avoid it.
    – GOATNine
    Jul 5, 2018 at 16:34

I wouldn't be surprised if I requested a vacation two weeks before leaving, and my boss told me "no". It's also not impossible to ask for a vacation on particular dates many months in advance, and having your request denied because an important deadline is scheduled on these dates.

There are however scenarios that you shouldn't let happen:

  1. Every vacation request is denied, making you lose your vacation days. To avoid this, turn vacation denials into reschedules, e.g:

you: Boss, can I take 2 weeks off in July?

boss: Sorry, that's not possible.

you: OK, should I take vacation in August instead?

If this game continues, simply take your vacation before it expires. Your boss cannot refuse you this time.

2.You have to prepare your vacation (tickets / hotel bookings / etc.), and cancelling it will cost you money. In this case inform your boss about it (in writing), and ask them to take a decision by a certain date:

Hi Boss,

I plan to go on vacation to South Africa this October, and I will be booking my tickets soon. I plan to leave on October 5 and come back on October 20. Could you please check if these dates are OK, and write me back if there is an impediment? I need an answer before end of July.

Assuming the deadline for the answer is 1-2 weeks from now (and your boss is not on vacation), if you don't receive a negative reply you should be good to go. If your boss later changes their mind, show them the e-mail and ask them if they would cover your rebooking/cancelling expenses. Or tell them that you're going anyway, if you want this trip really badly.

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    "Your boss cannot refuse you this time" - in the US your boss can very much refuse to let you take time off. There is no legal requirement for an employer to grant you time off. They can require you to work on national holidays, although you're supposed to get "compensatory time". How often this really happens I don't know, but when I've had to work late/weekends/holidays, all I ever got was "Thanks for coming in". If you're an "exempt" employee (generally meaning you're a salaried employee who is "exempt" from hourly working standards) you don't get overtime, either. Jul 3, 2018 at 23:53
  • @Bob Is there a legal requirement to honor the contract, where paid time off is presumably mentioned? Also, rules would be different in most other countries. Jul 4, 2018 at 4:55

First, when he declines, you need to ask what would be an acceptable timeframe to use your PTO days. If he gives no acceptable timeframe, it sounds like you have three options:

  1. Accept that your boss is going to be very hard to work with when it comes to PTO and you most likely are going to miss out on using all your days each year (which more or less equates to money out of your pocket because PTO is a form of compensation).
  2. Don't ask for PTO, but instead say something came up that is unavoidable and you need to take time off. Explain that it is personal in nature (you can allude to your health and a dr appt, something with your kids, sick relative, etc if you want), your work is all caught up, it is not during a critical time, but you have to be out of office those days. If your boss is piece of work, this will most likely cause your relationship to chill rather quickly. If he is ok with it because he understands life/health comes before work, then you have found your loophole moving forward in how you should ask for PTO.
  3. Start looking for another job and use either option 1 or 2 in the meantime.

For clarification, I am not saying to take days off with no notice. Still give plenty of notice (2 weeks) and say that you will be out of office for personal reasons on those days.

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    "If he is ok with it because he understands life/health comes before work, then you have found your loophole moving forward in how you should ask for PTO." I'm not sure I can overstate how much of a bad idea this is. Jul 3, 2018 at 10:04
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    @dfundako PTO isn't the same thing as taking emergency or care time at all, in any way, shape or form. And while you have no obligation to tell your employers what you do with your PTO, that doesn't mean you can lie to them about it.
    – Cubic
    Jul 3, 2018 at 13:55
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    @dfundako: Lying to your boss and using that lie to obtain a different kind of leave than you are actually taking is not "the same thing". Also note that in many jurisdictions there is a specific, contractual difference between elective annual leave and medical/sick leave. If you are requesting the latter, you'd better actually need it; if you work for me, and I later find out that you didn't, you're gone, immediately. Jul 3, 2018 at 17:29
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    @LightnessRacesinOrbit Fair. But if you're the type of boss that denies all PTO requests, your best performers would be gone, immediately. If you are an oppressive, unreasonable boss in the first place, don't expect to get the most forthcoming behavior from your people. Also, you're real hung up on the medical stuff. I said that was a possibility and you can allude to it if needed, but overall all you have to say is "it is personal and I won't be here, sorry. "
    – dfundako
    Jul 3, 2018 at 18:16
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    "Accept that ... you most likely are going to miss out on using all your days" Why should anyone accept their boss stealing from them? Jul 3, 2018 at 23:57

Do you have to ask for approval?

At some companies you don't have to ask before you take vacation (but many people just assume they do and ask anyway), you just have to notifiy your supervisor in advance. If that's your situation ("you" here refers to the OP or to anyone else with this problem), then don't ask, tell. So e.g. this: "I'm going to be out 7/3 - 7/21 without access to email. If there is an emergency, you can send me a text @ 555.555.5555" instead of this: "Is it ok for me to take off 7/3 - 7/21?". It's harder for someone to say no if you don't ask their approval.

NOTE: Some companies require you to ask, so then you should ask. But some don't, hence this answer. If you have to ask, then see the other answers for how to ask. Otherwise don't ask, tell (politely).

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    "Some companies require you to ask". I have never (in nearly 40 years) not been required to ask (although I have never been denied either). This is UK, Germany, and Switzerland. Jul 3, 2018 at 8:44
  • @MartinBonner many companies nowadays let you take any number of days off as long as you give enough days in advance and finish your work. But they quite the exception.
    – ecc
    Jul 3, 2018 at 11:58
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    @ecc : I think that's a very American thing. Europeans tend to have 20-30 days holiday, ~8 public holidays, and as much paid sick leave as you need (subject to a doctor's note after a few days). Jul 3, 2018 at 13:21
  • @ecc Right, that's the point: you have to finish your work. And if that's not possible, your manager or whoever is responsible for you PTO is likely to say "no".
    – glglgl
    Jul 3, 2018 at 15:10
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    I'm in the U.S. and have seen the situation where you don't have to ask as long as you give enough notice and aren't causing problems for projects. I understand it won't apply in all cases, but some people looking for similar help may find themselves not having to ask, but assuming they do--I did when I first started working even though I didn't. And besides it felt really odd to tell my boss I was taking off without asking. It was a skill I had to learn.
    – bob
    Jul 3, 2018 at 15:57

I see that you are "guessing" the reasons.

Can I suggest you to figure out the real reasons by having a conversation with your boss?

  • First listen the reasons your manager has to be so difficult when asking for vacation
  • Then have a speech ready explaining that your deadlines will not be affected by your holidays

Try to also have some information about how not taking vacation is actually counter productive in most cases and that having freedom allows you to be more effective at your work.

  • 2
    I updated my question. I'm not guessing, he has more or less told me he's denying it because too many others have also taken off around this time. I'm not these people's primary backup either.
    – Jay
    Jul 2, 2018 at 18:55

You say the issue your boss has is that too many employees are taking off at once, so why not help him to address the issue.

Try introducing a shared calendar or somewhere your team can document its scheduled time off. Having this, you should be able to come up with some general guidelines about how many team members are needed at any given time.

This also gives your boss a place to mark "critical" time periods around deadlines where more team members are needed. Having these critical periods documented will force him to make decisions about what is important, where left unchecked he may be likely to see any time period as critical (there will always be deadlines!).

Having a concrete policy should remove any confusion around the issue, just be sure the rules/guidelines are reasonable. If you find your boss resistant to such ideas, you may find that he's not been truthful to you. This is good to know. Do what you can to get to the root of the issue, but be prepared to move on if you feel you're being taken advantage of.

  • 1
    We do this at work. A shared vacation calendar on a network drive. And discussion things with my coworkers (oh, you, my only replacement, will go on holliday in the first week of August. Then I'll book the third week of August and we still have a few days so sync what happend while you were on vacation). No manager approval needed, and approval is assumed if we either mail when we are of and it is not denied within 2 weeks. Check when you personal handbook has, it might have a similar thing on the 'has to be denied in 2 weeks'.
    – Hennes
    Jul 3, 2018 at 22:29

One way or another, my friend, it's time to tell boss-man "Adio', mo' fo'". Since this is the US your employer has no obligation to allow you any time off - but any employer who wants to keep their employees around knows better than to use the "we're too busy to allow any vacation" excuse too much. My suggestion is to go find another job, either in the same company working for another manager, or if it's a company-wide issue then with another firm. Their attitude is, apparently, that vacation is a privilege, and lower-level employees are not sufficiently privileged. Time to wake 'em up when you walk right out!

And, if you're interested - there's a way that employees can fight this kind of treatment. It's called "a union". If your employer is consistently behaving like this - denying exercise of benefits, minimal/no raises while company is profitable, excessive hours on a regular basis, etc, etc - it may be time to organize. I remember some years ago that the lawyers working for the US Attorney's office in, I believe, Seattle (or somewhere up that way) had to bring in a union due to unreasonable working conditions. Tough to tell an attorney that they can't organize, etc, when it's their job to know the law. :-) The AFLCIO has their Department for Professional Employees, which I gather specialize in organizing white-collar workers.

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