I'm not asking about negotiating during the interview stage, I'm asking about how to get use of time off approved at work. I'm not interested in the answer "just get another job" because this is my third job and I've had the issue at all three, so I think it's something I need to work on. Every manager I've had has responded this way, so I don't believe that a new one would be different.

I often either want to use some of my allocated paid time off for a vacation, or need to use it to take my car in for maintenance or visit the doctor. Every time I've emailed my manager or told them in person that I'm planning on taking off specific dates a few months in advance for vacation, or a week in advance for car/doctor visits. Every time I've always been told "No. You may not take off time." Sometimes it's because of a project that needs to be complete, sometimes it's just "No", sometimes it's "That's something you should be doing outside of work". I've tried persisting or finding ways to complete my work by staying late or working on the weekend, and usually my manager will end up saying "You will be fired if you are not at your desk on that date", so I never use any time off. I end up just going to a MedExpress on the weekend, never going to the dentist, never having a vacation, selling my car as-is and buying a different used one, etc.

What are some techniques I could use to get better at this negotiation?

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Neo
    Commented Dec 10, 2020 at 20:28
  • 19
    Where is this happening? Not allowing workers to take time off is outright illegal in several countries, so a country tag or just editing the question to tell us where you are might help in getting more appropriate answers.
    – walen
    Commented Dec 11, 2020 at 8:02
  • What is your general location?
    – Mast
    Commented Dec 11, 2020 at 16:43

7 Answers 7


What are some techniques I could use to get better at this negotiation?

First, it should never be a negotiation. Get the idea of negotiating one of your benefits out of your head.

Learn and understand your rights as an employee, that way your manager or any other employee cannot walk all over you. Make sure you carefully read your contract and employee handbook and are clear about what exactly you are entitled to as far as vacation/sick days and the proper procedures for requesting those days. If anything is unclear, you should reach out to HR in writing so that they can clarify your exact benefits and the procedures for being able to use them.

Next, you ask your manager for the time off following the company procedures. Normally, you don't need to provide any reason for your planned time off. In some cases the manager will have to approve the time off and that is company policy. If you are denied, you need to ask your manager to provide you with dates that he approves. If the manager does not provide any dates or attempts to push back against the company policy in any way, you escalate to HR.

I know you don't want to hear "get another job", but I don't understand why you would work for a company that repeatedly denies you of your company provided benefits for no reason at all or a ridiculous reason such as "That's something you should be doing outside of work". Top that off with being threatened to be fired if you are not at your desk on a specific day (accidents, illness,....etc are a real and uncontrollable thing). Either you have had terrible luck with your managers or you live in a part of the world where treating employees like dirt is common. If it is the former, you really should start looking for a new company to work for and make sure you do thorough research on any potential companies policies.

  • 48
    In most jurisdictions annual vacation days are not a “benefit” but a law.
    – Michael
    Commented Dec 10, 2020 at 10:14
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    @Michael of course, while it might be true in most countries, it isn't true in the US where a disproportionate amount of users of the site are in. The OP mentioned using MedExpress which is a US company. Commented Dec 10, 2020 at 16:44
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    @DeanMacGregor Then OP needs to clarify that via tags. Assuming every question is from the US does a disservice to the site and is actively discouraging for users who are not from the US. Its fine to have a lot of questions from the US, but at least tag it correctly, especially when it matters so much like in this Q&A.
    – Polygnome
    Commented Dec 10, 2020 at 17:17
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    @Polygnome I am not my brother's keeper. Commented Dec 10, 2020 at 18:02
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    @ChrisSchaller "almost always" is a contradiction in itself. In many countries the negotiation is the other way around. I send my request for vacation days and my boss must approve it unless he has very specific important reasons to deny it. Besides that he might negotiate with me, if I would be so nice to take some other days off. That's not in my contract but in the laws.
    – Chris
    Commented Dec 11, 2020 at 12:53

By just taking the time off. You need to set a precedent, one that's honestly hard to do if you're not a proven contributor. The more valued you are, the more you can force the issue. When you're taking time off, TELL THEM you're taking the time off. Don't ask for permission. If you've given them at least two week's notice. Tell them, "I will be using my PTO from X day to X day." And take that time off. If you have a manager that can't figure things out two weeks in advance, that's a bad sign. If you have a manager that can't let their people take time off for ANY reason, that's a red flag. If they can't allow you time off, what's the point in accruing it?

If its less than two weeks, obviously you need to be understanding that making schedule changes at short notice is not always feasible. There is give and take. They don't own you. There is a mutual agreement that needs to be held up on both sides. Not "allowing" me leave is something I would not tolerate.

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    FWIW, in many countries that require companies to give PTO, the company generally has the right to dictate when that time is taken, if they so choose. So you can say "I'm taking these days as holiday" but if your manager turns around and says "no you're not" you can't actually just go and take it anyway.
    – Kaz
    Commented Dec 9, 2020 at 18:21
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    Thanks DarkCygnus. @Kaz: just like your work has to deal with the repercussions of you choosing another workplace, you also have to deal with repercussions of your workplace not valuing you enough and letting you go. I work in an at-will state where you can be let go for any reason, no matter what. I took time off without "permission" but they did nothing. Why? They were calling bluff and I was not allowing a precedent to be set where they dictate my life. We are in a mutually beneficial arrangement. Act like it. Is it worth it to them to let you go for two weeks or them lose you for good? Commented Dec 10, 2020 at 0:56
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    It really depends what you work in. You can't have all nurses at the hospital taking Christmas' week off, no matter how long before they notify management. Many work-places require a minimum of a certain number of employees to be present on certain days, which requires coordination of time-offs; recommending "just taking it" without knowing if there are such conditions is not helpful. Commented Dec 10, 2020 at 8:50
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    @MatthieuM. This is true, but there's a difference between employers "just saying no" and coming back with things like: "I can give you half, I need coverage on X shift." "We're short-manned then, can you try these days? "X person already has that vacation slot, can you work with them?" - I've had to manage a 24/7/365 enterprise service desk with 7 people and I found a way to make it work for 2 years. If they are unable, that's a sign of a bad leader/manager. Commented Dec 10, 2020 at 13:08
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    @Kaz You are dead wrong in a lot of jurisdictions. Where PTO is mandatory, it also often a right given by law, and the company can not easily deny it. In germany, you can say "I'm taking vacation from X to Y" and the company needs to have very good reason if they want to deny that, and they have to give those reasons in writing -- allowing you to challenge those reasons if needed with legal council.
    – Polygnome
    Commented Dec 10, 2020 at 18:03

Doing a quick search, referring to MedExpress means you're probably American, so I'm going to answer this question from a North American perspective. I'm going to give some legal advice in the context of my answer, so I'm going to preface my entire answer by saying I Am Not A Lawyer, you should seek professional legal advice, and so on. With that said:

You're being screwed. Your employer is not allowed to deny you of using your vacation days. They are allowed to deny some days, for some reasons, within certain guidelines, but they are not allowed to blanket refuse you whenever you ask for vacation time. You are contractually entitled to some amount of vacation days, and you are contractually entitled to be able to use them on some amenable schedule, and your employer has to be reasonable to ensure that you can negotiate some schedule to do so. Regarding sick days, I don't know the details, but they probably fall under similar constraints, where your employer is allowed to require you to prove you were sick (with a doctor's note or something) but they are (probably) not allowed to force you to come into work when you're ill.

If you are fired over this issue, you probably have a legal case to bring against your employer for violating your contract by disallowing you access to sick and/or vacation leave. If it is really as bad as you say, you should consult legal counsel and see what they say. If they agree with this, you should:

  1. Document everything. Get as much from your employer in writing as possible, and keep a personal diary of the rest. This means, when you want to go on vacation, send the request to your boss by email, not by talking in person. When you are sick, send an email, don't call on the phone. If you need to take your car for maintenance, you guessed it, email. If your boss responds to your email saying "please talk to me in person", keep a record of that, talk to him in person, and try as best you can to voice-record the conversation on your phone, and/or keep a diary of the meeting after the fact (what was discussed, what was said, and so on).

  2. After you've collected some data as above, the next time your reasonable request is denied, do it anyway. This is difficult to do with actual vacation, but is much easier to do with sick days or other one-off appointments like car repair. When one of these appointments comes up, send an email to your boss saying you have an appointment and need the day off (don't ask, tell). He'll send you back some email like "if you're not at your desk then you're fired". Call his bluff. Make him fire you. Make sure you get some verification for where you were, and that you were actually doing the thing you said you were doing, for evidence in court; if this is a doctor's appointment then get a doctor's note, if it's a car repair then get a receipt from the mechanic, and so on.

  3. If he fires you, take the company to court. The court will find in your favor and you'll definitely make enough money to at least tide you over until you find the next job, if not more.

Before you do the above though, once again: seek legal counsel and make sure this is a reasonable plan of action. If you don't actually have legal grounds to sue, then this is not a great plan; you're just going to lose your job and be back to square one.

The bottom line is, don't take this sitting down, you're not being treated right and you should make your employer treat you properly.

One more thing: do not make a complaint to HR. You don't want them to know this is coming. Any complaint you make to HR is likely to come off as a threat, and that's going to make them fire you before any of this plan goes into action. The only complaint you might want to make to HR is right now, you may want to send them a blanket non-committal notice that your boss is being unreasonable with time off, much the same way you said here, with examples. If they follow up then great, if they don't, then drop it and go to see a lawyer.

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    If the boss demands in in-person conversation instead of replying by email, follow up with an email to him detailing the conversation and asking for confirmation/corrections. Create your own paper-trail when she refuses to do so, because she knows what she's doing is wrong.
    – FreeMan
    Commented Dec 10, 2020 at 14:08
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    Recording phone calls without permission from the other party can press its own legal challenges, there are many states, where recording of a phone call requires two party consent. Now I agree that an emailed receipt of your request and calling is an excellent idea.
    – Donald
    Commented Dec 10, 2020 at 14:13
  • @PaulK - because it is generic mumbo jumbo that you could say for any question that really does not put the person in any better stance. For the average person not seeking a "great" attorney but who they just find, you are just as likely to get bad advice from them or advice that makes them need to see you more. Talk to an attorney is not a valid piece of advice. You can say specifically what laws and rights you should talk to an attorney about and specifically what kind of attorney and examples. Talk to an attorney is by itself - dumb advice.
    – blankip
    Commented Dec 10, 2020 at 20:09
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    @blankip If you actually read the answer rather than spewing garbage, you'd see I actually told OP specifically what he should ask an attorney about.
    – Ertai87
    Commented Dec 10, 2020 at 20:11
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    @blankip That's what the "downvote" button is for. Please use it. There are currently 10 other people who disagree with you, however. If you have your own thoughts on the issue, I'd welcome you to provide your own answer to help OP make a better decision than what I've presented.
    – Ertai87
    Commented Dec 10, 2020 at 20:18

I don't ask for time off. I inform my manager of my availability, and they just have to deal with it. I will not be there the days I tell him I'm taking off. That's the attitude you need. Stop negotiating, and start telling them how the world actually is. By negotiating at all they know they can steamroll over you.

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    While this is very good advice and the process I've followed almost from day-1 of my work career, not everyone is in a position to do so. I work a white-collar desk job and except for very rare occasions, there is nothing that I do that can't wait until next week (that isn't also automated). However, some people work jobs where someone has to cover the work and it's up to the manager/scheduler to determine who gets to take time off and when. Telling just doesn't work in those situations. +1
    – FreeMan
    Commented Dec 10, 2020 at 14:11
  • This really depends a lot on the balance of power between employer and employee. If the employee is in an at-will state in the US, is easily replaceable, and/or the employer has specific constraints, then this will end badly.
    – jcaron
    Commented Dec 11, 2020 at 13:13
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    @jcaron If they're an hourly employee in retail, possibly. If they're in an office environment it won't at all- because replacing and training the replacement will cost orders of magnitude more difficulty and money than just dealing with it. And quite frankly- if you work at a place that has an issue with this, why would you want to stay there? Find a better place to work. Commented Dec 11, 2020 at 23:30

While I wouldn't classify it as a negotiation, there are steps you can take depending on the nature of your job.

My job is client facing so I typically make sure of the following:

  • As much as possible I include planned vacations into any schedule estimates for my project work

  • I let my clients know when I'll be out of office as far in advance as possible

  • I remind my clients of my planned absence a few days in advance so they can take advantage of my remaining time if they have any pressing requests

  • I work with my colleagues to make sure I am covered in case of client emergencies

This way, I can submit a time off request along the lines of

Hi Boss - I'd like to take the week of the 15th off as vacation. Fred will be my emergency cover, and my Acme client issues have all been addressed. The Roadrunner work will still be on schedule for delivery on the 31st.

(My company and my boss are very amenable to letting staff take time off, but I still follow the above steps)


Do not negotiate about whether you take time off. While the USA may be unique among "developed" countries in that it is the only one where Vacation time for employees is not legally mandated, you indicate that your company has already allocated an amount of leave for you to use.

Instead, negotiate when you will be taking this time off. Taking your "car requires maintenance" example, you could draft an email along these lines:

Hi [Manager],

My car is currently in need of maintenance. Unfortunately, due to the operating hours of the garage, it is not possible for this to be scheduled outside of office hours. As such, I intend to spend some of the Paid Time Off budget that the company provides me with to handle this necessity.

The garage has openings on [Date1], [Date2], and [Date3]. If you could get back to me before [EarlierDate] with whichever of these is most convenient then I can confirm with them, and also ensure that there is suitable cover and no disruption to any ongoing work.

Many thanks,

If your manager insists on refusing any of your leave, continue to treat it as a budget: The company has provided you with this resource, and since you are unable to spend it in its existing form (Time Off), ask what options your manager will provide for you to cash it out, and convert it to money?

(The main point of asking about 'cashing out' is not to actually 'cash out' — but, rather to emphasise that this is something is provided to you by someone higher up the 'food-chain', and you will be using it in some form or other. If it gets pushed to the accounting department that you are asking for additional payments because your manager is refusing your leave requests, the pressure will hopefully be put on them to avoid monetary cost to the company, by allowing you to use the leave which has already been accounted for in the existing budget)

  • I disagree with this because giving a reason why you want time off will just invite argument about it (the OP has already experienced this, "you should do that outside of business hours"...and saying the garage is only open x times will just end up with why don't you go to a different garage, etc.). Commented Dec 18, 2020 at 15:23
  • You can offer a few (no more than 3) options if you have flexibility, but it's mostly a good way to use language that indicates that you WILL be taking time off and you're only offering a choice of which day. To that end, I wouldn't be too overly nice in my word choice. Just "I need to take off either X or Y. Let me know which is better by Z, otherwise I will assume that it is X." Commented Dec 18, 2020 at 15:23
  • @user3067860 So, you actually agree with my answer, but dislike my example? Commented Dec 18, 2020 at 23:32
  • I highly disagree with the "cash out" option. Vacation time is worth more than the value of the paid time it presents. By offering to "cash out" you are robbing yourself of non-monetary compensation due to you by the company.
    – GOATNine
    Commented Dec 19, 2020 at 13:29
  • @Chronocidal I think that example might be one of the specific places the OP is currently running into problems, based on this line from the question: "sometimes it's "That's something you should be doing outside of work"." 1) The OP doesn't need to provide any justification for why they want a day off. 2) When the OP does provide a justification, it is used as a reason to deny the OP's vacation. 3) So the OP should specifically avoid providing justification for time off. Commented Dec 21, 2020 at 12:48

You've indicated that this is not the first employment that you have experienced this issue with, I am glad that you have posted this question because as much as you have rights as an employee (as pointed out by other responses), we do need to acknowledge that your managers are to some extent human (and employees themselves) too, and they may have competing pressures from Clients, Upper Management, Shareholders and other employees that will impact on the response to your request just as much as the request will impact on them.

Firstly, if you were genuinely sick, especially if you were in some way contagious or otherwise unable to perform your work in a way that is safe for both you or those around you, that might include taking some types of prescription or otherwise substances... Then in this case you would simply not show up to work and it would go down as a sick day, there's nothing to be done.

  • Don't do this too often, but sometimes, if you absolutely must take the day off, and you can't give enough notice or your leave isn't approved, then go get your medical certificate and be done with it, stress is itself a medically recognised ailment and who is to say what level of stress trying to get this day off work has caused you :)

This is a negotiation, that means that you need to be seen to be offering something in return

Even if you are only offering to hand in 1 day of your allocated leave, go into the discussion with a mindset that you are sacrificing something of your own in return for a day of freedom. Lets go through a checklist to make sure you are prepared:

  1. Be aware of the leave policy that is part of your employment contract. Every workplace will have expectations or policies around the application for and the dispensation/execution of Paid and Un-Paid leave. Whether it is written down or not is a different issue, but there will be a set of rules and likely requirements.

    • You absolutely should enquire about Paid and Un-Paid leave policies during the employment application and interview process.
    • You should not feel any fear or prejudice in asking about such policies at any time during your employment, it is in the employer's best interest to make this information freely available should you request it as it sets their expectations and helps avoid conflict.
    • If the policy is that there is no leave then that becomes a legal issue in some jurisdictions, and certainly a red flag warning you to re-consider your employment.
    • Some employers will allow you to negotiate terms around leave, in some jurisdictions there are legal safeguards in place to protect you from (yourself) negotiating an unfair arrangement. If you cannot ever get leave approved, seek legal advice.
  2. Know how much leave you have accrued or are entitled to at the specific date you want to take off, your employer should not have any trouble providing this information, if they do have trouble then based on the information you learned from item 1, you should have a general idea.

  3. Be mindful of the impact that your leave will have on the organisation and your manager directly if your leave were to be approved. What appointments, deadlines or other expectations will be missed or might be impacted, does someone need to be brought in to cover your absence. Understand your specific Role, not just your official position, but the way that your colleagues interact or depend on you, this can have more impact that you may realise.

    • This is the part where you imagine yourself in your employer's shoes, try to anticipate any potential issues, are they specifically about the Date, is it about the amount of time, effort or notice that might be required to re-schedule things
    • Anticipate the obvious objections your employer might make and be prepared with potential solutions, perhaps simply the burden of having to figure out how to organise things without you is the main reason they keep denying your? So do the hard work for them.
  4. Be flexible (if you can), even if you cannot manipulate the timing of the leave, perhaps there is something else you can offer to compensate or offset this time off. Time in Lieu whilst not always officially offered, it can sometimes simplify the burden of payroll if you can simply swap days, or offer to catch up out of hours

    • You might not have to actually be flexible, but your should make it appear as if your are, this is a general negotiation principal, not just for your specific request for leave.
    • If this is an event you are scheduling, approach your employer for leave over a range of dates, and have them pick the one that is most suitable for them
      • Refer to item 3, if you can pick at least one date that that is going to cause the least disruption or demonstrate that you have made an effort to coordinate your life around work, not the other way around, then you may have more success.
      • You can cheat a bit like this, you know the date you want, but offer some other dates that you know would cause bigger problems, that way it becomes your employer's decision, not yours. If you suspect they will try to make your life miserable for the sake of it, don't make the easy one your first preference... its a double bluff kind of situation, you learn pretty quick if this strategy is an option or not.
  5. Maintain a good rapport / be on your best behaviour. maybe this should have been item 1... Your past performance, leave history and work habits will form a lot of the Good Will that you bring into this negotiation. Some quests to help consider your good will budget:

    • Do you show up to work regularly on time?
    • Do you complete tasks on time and on budget?
    • Do you provide ample notice when you cannot meet budget or time constraints?
    • Do you volunteer for additional or harder tasks?
    • Do you get along well with your peers / colleagues?
    • Do you get along well with subordinates?
    • Do you get along well with clients or other external stakeholders?
    • Do you generally make like easier for those around you?
  6. Finally, is your request reasonable? We're not just talking about "rights" and "entitlement" here, its more about morals and expectations and "have I worked hard enough to earn this as a personal favour from my employer".

    • Am I legally eligible for this leave?
    • Have I satisfied my obligations according to my employment contract to be eligible for this leave?
    • Do I have any leave accrued?
    • Do I have any outstanding requirements or deadlines?
    • Will they be able to manage without me?
    • Have I previously used up any remaining Good Will?
    • Am I abusing any position of power?
    • Will other employees view this leave request in a positive or negative light?
    • Is this event personally important enough to me to outweigh any negative impacts or side effects on my Good Will (can I morally afford to do this)
    • Have I recently completed some leave, or do I have an RDO that I could have reasonably scheduled this event for?

Some times we miss out on things in life, we can't always have what we want. However, if your personal situation means that you regularly need time during business hours to get things done, find a way to negotiate this into your employment terms. This might be in the form of a pay cut to get an RDO (Rostered Day Off) or to change your daily work times, say work 30 mins extra each day to get 1 day off each month... Maybe you just need a longer scheduled break to pickup kids or something like that, but by making a permanent schedule around when you will be at work, instead of interrupting that schedule frequently you will actually become more dependable and predictable, which is what we need in a business world.

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    The negotiation part was already completed when the company agreed to give you N days PTO. This answer suggests that the company can unilaterally renege on that offer, and that the employee should just suck it up. "Even if you are only offering to hand in 1 day of your allocated leave". NO. "a pay cut to get an RDO" NO. Just plain NO. If the company didn't want me to take days off in December, they should have included that in the contract. If they didn't, December is fair game.
    – MSalters
    Commented Dec 10, 2020 at 13:20
  • 17
    This is nonsense. The OP already gives something in return: their work. The days off are a part of the already-negotiated compensation for that work. Trying to bring "morals" and "expectations" into it in some effort to strip the worker of their rights (yes, it's a right; that was the agreement) is toxic AF. Commented Dec 10, 2020 at 13:41
  • Some of this is decent advice, but a large part is very specific to certain jurisdictions. Most of this won't work in the US, for instance. And as for Time In Lieu, IME that's usually a benefit offering and if your employer isn't offering it, it likely can't be negotiated. If they won't pay you for not being there, they aren't going to pay you more than your normal wage/salary either. And just not showing up to work without notice won't just go against Sick time automatically. That's called a No Show and often reason for getting fired. Commented Dec 10, 2020 at 17:20
  • OP has indicated that this is a common problem for them and by virtue of asking the question has also demonstrated that they are not aware of their current agreement with the employer, I was simply responding in a polite manner, lets assume they have forgotten. I certainly have no Idea where my employment contract is or what might be in it, and have asked these questions in the past because I forgot. Commented Dec 11, 2020 at 0:40
  • @AsteroidsWithWings when we put in a request for leave, in many cases the employer will have some discretion on when or if they will honor the request, your rights say you must have leave, but not on the specific day that you request it. So we have to play the game to some degree whether we like it or not. If you are reasonable in your request then you can hope for a reasonable response. If after time you deem your employer to be consistently unreasonable then find a new job. Commented Dec 11, 2020 at 0:44

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