I'm taking a vacation in mid-April of next year with some friends, we've all already gotten the time off approved from our various jobs and bought plane tickets. My previous manager said it was fine and even thanked me for letting him know so far in advance. He recently got a promotion and last week his replacement started, and she immediately unapproved my PTO (paid time off) and said I can't take that week off as she wants me to attend a conference that week. She says attending this conference is "a condition of your employment here".

This is something I'm willing to quit my job over, but I'd prefer if it didn't have to be that way as everything else about this job is great. I got excellent performance reviews from my old manager and he's still with us. I also know they've been trying to hire a second developer in my domain and can't find anyone, so they can't replace me easily. What's a good way to negotiate based on this?

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    Is this even legal? I would very surprised if a contract allowed them to revoke PTO once it has been granted…
    – o0'.
    Commented Dec 10, 2019 at 11:33
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    What jurisdiction is this? And if it's the US, please include the state as well. Commented Dec 10, 2019 at 13:43
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    Aslo what form did your previous manager's approval of your time off take? If there is any kind of written record, you really want that, as it is evidence of a time-based commitment to you by your company. Commented Dec 10, 2019 at 14:00
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    Sorry to nitpick, but I believe "unapproved" shouldn't be used this way (as a verb - unless it's some special HR slang or jargon which I'm unaware of). Better to phrase it as "New Manager rescinded PTO that my old manager had previously approved."
    – Deepak
    Commented Dec 11, 2019 at 2:02
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    If you don't mind, please post an edit to your question about how things worked out, when available.
    – xxbbcc
    Commented Dec 11, 2019 at 19:51

7 Answers 7


She's just a manager. She's not the company owner. There is HR, and there is your previous manager who is in a higher position than she is. So unless your previous manager always wanted to get rid of you and left the dirty deed to her, you are reasonably safe.

"Attending the conference is a condition of your employment here" is extremely confrontational, and 99% something that is way out of her authority. It's not her decision, it’s the company's.

So I'd first give a short notice to your previous manager, just to keep him informed, and then take it to HR. Put in a formal complaint. Tell them about the total cost (which is you and your mates cancelling flights and hotels and rebooking at another time) and ask whether they are willing to pay for those expenses. Not just yours. If they agree in writing then you'll have to go to the conference. The chances of this happening are approximately zero.

HR may tell you that you don't have to attend the conference, based on the facts. Preliminary problem solved. If they say you have to attend, you can tell them that you are willing to leave about this. This may or may not change your mind, and may or may not change your manager's mind. Keep your ex-manager informed. He may or may not take action.

So if HR tells you that you have to attend or lose your job, you start looking for a better job. When you find it, you give notice. If not, you go on your trip. Make it clear enough that you are going on your trip so nobody is tempted to buy tickets etc. for you to go to the conference. Then you'll see what happens when you return.

BTW. Anyone they try to hire should be informed about the situation. Which is not in your company's best interest, but in yours.

PS. This is of course a fight about power with your new manager. If she loses, that's her own fault. She won't be happy. Expect the worst from her, but there's a chance that you'll stay longer than she does, because that kind of confrontation that she started is just stupid for a manager.

Some of this obviously only applies if you are confident to get a good job elsewhere.

PS. Just read you have been asked to book hotel and flights. Don't. Not if you consider staying with the company at all, because it will burn goodwill with HR and your old manager. On the other hand, if your new manager takes it upon herself to book flights and tickets for you, preferably after you talked to HR, and you don't go, then the waste of money is her fault.

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Neo
    Commented Dec 10, 2019 at 14:38
  • Make it clear enough that you are going on your trip so nobody is tempted to buy tickets etc. I assume this part you are talking about making it clear to OP's friends so that they don't cancel/refund their tickets?
    – Aequitas
    Commented Dec 10, 2019 at 23:18
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    No, he means make it clear to the company that you are going on your vacation, so they can't buy your tickets and then create an issue of wasting company funds. (There was some previous question in which this was an issue, so it's a good point.) Commented Dec 11, 2019 at 2:09
  • I would not bother telling them about the total cost and asking them if they are willing to pay. I think this comes off as confrontational and doesn't add anything to your position. It's needless information and throwing big dollar signs at employers to get your way doesn't seem like appropriate behavior. Commented Dec 13, 2019 at 18:53
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    I don't agree with the bit about going on the trip without giving notice, in the case where HR hasn't overruled the manager, and you haven't found a new job yet. That allows them to fire you for cause. I would instead advise to hand in notice at whatever point you need to in order to be free to go on the trip, even if you haven't found a job. I wouldn't necessarily give that same advice to someone who hadn't already said, "I'm willing to quit", of course. Commented Dec 24, 2019 at 13:12

If in your first interaction with your new manager, that manager threatens to fire you for not cancelling an already approved PTO just to attend a conference, you clearly need to establish that you won't put up with that behavior. Any kind of negotiation that lets your manager get away with this would just mean more of the same in the future. If she's willing to make this much of a fuss over a conference, what's she going to do when it's really significant?

Go to your manager's boss, lay out the facts of the case and state that you are unwilling to cancel your vacation. Your manager won't appreciate this but let's face it, that bridge has already been burned by her actions. Since you've received excellent performance reviews in the past, and this demand is so ludicrous, you should be in a good position, particularly since it's just a conference.


I would talk to your old manager and get him to find out if she is serious.

Is she just trying to show off her authority? If so, then that is an easy way to lose a developer with what looks like serious consequences. If they have not been able to find a suitable second yet, then if she causes you to move on, she would be signing her own leaving certificate...

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    Even if it's not the direct boss of the new manager, the old manager will have influence.
    – gnasher729
    Commented Dec 8, 2019 at 21:26
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    +1. You can't go wrong asking your old manager for advice on how to handle this before you escalate it. Also, it's possible your new manager is green in her manager job and didn't get the memo about honoring existing commitments on taking a new assignment. Somebody, not you, needs to send her that memo.
    – O. Jones
    Commented Dec 9, 2019 at 13:06
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    The new manager is countermanding the old manager's decision to approve the PTO. That is another reason the old manager might be willing to intervene. Commented Dec 9, 2019 at 16:53
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    @RBarryYoung I will let you read the other answers as you have certainly missed one. In fact, why not write your own definitive answer so it can be perused and voted for...
    – Solar Mike
    Commented Dec 10, 2019 at 14:54
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    @RBarryYoung The previous manager is not retired. He is part of the company, in a higher position than the new manager. If the new manager accused OP of insubordination then all the old manager has to do is tell her and HR that he advised OP to come to him if there are any problems. The previous manager wouldn't sit back and let a new manager destroy in a short time what the previous manager built up.
    – gnasher729
    Commented Dec 10, 2019 at 23:57

The new manager says, 'attending this conference is "a condition of your employment here"'. The old manager already decided it wasn't essential that you be available that week, and you have that in writing in the form of the original approval for the leave. You have a bus factor of 1 on your job and you're willing to quit. The new manager hasn't (as far as you've said) even explained to you why she thinks this conference is so important, so she appears to be demanding blind obedience at great personal cost to yourself.

So, unless your new manager knows something you don't, to explain why she's trying to get you to quit, she's made a tactical mistake here. Maybe she, rightly or wrongly, knows one or two people that she would like to hire to do your job. You don't know for a fact that she needs you, so you'd better be serious about leaving before mentioning it to anyone in your company. Anyway, most likely is that she's misjudged the situation and thinks you'll cancel the trip if she leans on you.

I disagree with the answers that say your first response to this mistake should be to go to HR or your old manager. OK, so your new manager has started out by setting an extremely hostile and uncompromising tone for your relationship. Maybe that's what she wants, in which case one of the two of you will be leaving sooner rather than later. But if it's not what she wants, then letting her "deal with it" (that is, change her mind gracefully) will tend to defuse the situation. Proving in front of witnesses that her authority over you is not what she thinks it is, will tend not to.

Your first move should be to convince your new manager that your old manager and you both know what you're doing, and that you aren't needed at the conference. So, go to her and say, "this has been considered before, the leave was approved by the company, I have committed to the trip on that basis, and the trip can't be moved because it involves four people with leave booked from four different employers. I don't think it's essential that I attend the conference, [if you already discussed that conference with your old boss at the time you booked the leave, insert here the agreed reasons]. In any case, I can't attend the conference because I'm committed to my trip."

It's now her choice. She can back down, in which case the negotiation is over, or she can stand her ground and repeat that the company requires you to attend the conference as a condition of your employment. If the latter, then someone else needs to be pulled in to sort it out.

If your old boss was promoted directly upwards, and therefore is her boss, then he's in a better position to change her mind than you are. So, the next step is to go to him, on the basis of your existing relationship and the fact that he had already authorised the leave, and let him understand that there's a serious problem going on under his authority. This is "going over your boss's head", with all the drama that implies, but her contradiction of his decision is precisely the kind of situation where going over her head to her boss is appropriate.

If he's been promoted upwards and elsewhere, then he might not be any use, other than to officially confirm that what you're saying about your past discussions with him is correct. Or maybe to give you personal advice how to deal with the situation given that he knows a lot more about it that I do! If he can't help you, you'll have to go either to her boss or to HR, whichever fits better with your company's usual way of doing things.

If you do formally complain, then your complaint is that she has threatened to fire you over pre-booked leave that you're committed to taking. HR is going to look both at whether the company legally can do that, and even if so whether she has the authority to do that on behalf of the company, and even if so do they agree she's done the right thing by making that threat. So, the more of those questions you know the answer to in advance of making the complaint, the better. If you can get that threat ("attending is a condition of your employment") in writing then that's much simpler for your complaint than if it's just verbal. As against that, if it's just verbal then you might literally be able to ignore it. She can't fire you without ever writing anything down.

Also, be prepared that if the company does back her, you need to pay attention to the terms you're leaving on. Even if their demands are ridiculous, it's generally better to quit than be fired, except perhaps in the extreme where you plan to make a legal case of it. Depending on company rules, you might not be able to use your old boss (and other colleagues) as a worthwhile reference, especially if the company decides to fire you before you quit, so take into account what happens next. If you are concerned about retaliation from HR or whatever, then it might even be best for you just to quit without ever escalating to them: there's no point involving anyone you think will take her side.

The fact that the job is otherwise good suggests that this isn't a big risk, and probably the company will back you, but even good companies can occasionally surprise you with how seriously they take the heirarchy. Until they agree that she's well out of line, the default assumption of most higher-level managers is going to be that they don't want to keep a dog and bark themselves. So, if there's a lower manager in position then that's because middle/senior management doesn't want to have to make decisions about leave. In this case you have going for you that your immediate manager at the time already made this decision, and she's trying to reverse it. So, respect that this isn't about whether or not she has authority to approve or refuse your leave (because of course she does). It's about whether not the company backs her in revoking assurances the company already gave you, and which you have heavily relied on, and which the company (in the form of your old boss) knew you would heavily rely on when it gave them.

Ultimately, you already know what your own position is, so this whole negotiation is about whether your new boss, and the company as a whole; (a) want to force you to say you're prepared to quit over this; (b) want to call that threat (or, as they hope, "bluff") once you've made it. I think your first moves should avoid even (a), because once you've threatened to quit a job there's no guarantee you can get back to a place where your employer feels they can rely on you. So, try to get the need to quit off the table and then you won't have to tell them that you are prepared to quit. That said, if your new manager really is as bad as all that, then one or both of you is leaving soon anyway, in which case it doesn't really matter what she thinks of you!

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    – Tony Ennis
    Commented Dec 9, 2019 at 21:50
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    If someone other than HR tells you that something "is a condition of your employment here", then that is something that HR must be told about. Immediately. If we forget about the employer/manager relationship, this manager is undermining the company and HR.
    – gnasher729
    Commented Dec 9, 2019 at 23:45
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    Sure it's a long answer, but it's a very good, very readable long answer. Commented Dec 10, 2019 at 13:37
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    +1 on get it in writing. -1 on "it's better to quit". You may forfeit certain rights if you voluntarily quit... such as the right to collect unemployment. I'm aware this condition probably depends on jurisdiction. But it may not be better to quit.
    – James
    Commented Dec 10, 2019 at 18:54
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    @TonyEnnis That's what the voting mechanism is for.
    – Beska
    Commented Dec 10, 2019 at 20:22

Whether or not there is a legal basis (e.g. employment contract) for them revoking your leave, you may be covered under Promissory Estoppel.

This is not legal advice, I am not a lawyer.

The elements of Promissory Estoppel are:

  1. Some form of legal relationship either exists or is anticipated between the parties
    • You are their employee, so a legal relationship already exists.
  2. A representation or promise by one party
    • The PTO was approved by your manager, acting on behalf of the company.
  3. Reliance by the other party on the promise or representation
    • You booked travel/accommodation based on the approved PTO.
  4. Detriment
    • You would be out of pocket for the costs of your missed holiday as a result of the revocation of your PTO.
  5. Unconscionability
    • in the circumstances, it would be unfair or inequitable to allow them to cancel your PTO.

The remedy for this would be for them to reinstate your PTO, or to cover the costs of your missed holiday.

Unfortunately, this would not cover any losses by your friends as the promise was made to you, and could not reasonably extend to your friends.

  • 6
    Law varies massively by Country/State. Question doesn't specify which country they are in but I think your link relates to Australia.
    – mattumotu
    Commented Dec 9, 2019 at 9:13
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    the question (currently) doesn't indicate what country/state they are asking about, so US specific answers would have the same problem
    – mattumotu
    Commented Dec 9, 2019 at 14:04
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    This answer is making a lot of assumptions and doesn't fix the problem.
    – Mast
    Commented Dec 9, 2019 at 20:48
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    I won a promissory estoppel case in 1989 and I was told at the time that it was new case law in Australia.
    – user207421
    Commented Dec 10, 2019 at 4:05
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    For all intents and purposes this answer is a bit useless. You are just saying that the OP might force the company to pay for his part of the trip. Well, that's not helpful, he'd rather quit the job anyway.
    – o0'.
    Commented Dec 10, 2019 at 13:07

TL;DR: Your boss is not justified, but it's (most likely) not a negotiation, so just make sure you handle this situation carefully and strategically to avoid costly mistakes.

Your boss is in the wrong, but tread carefully

I think your boss is totally in the wrong. That said, make sure you handle this situation carefully. If you leave, you want to do so on your terms; you don't want to get fired accidentally, or to poison your working environment without another job to go to. With that in mind...

This isn't a negotiation (most likely)

A negotiation exists when both parties have some leverage and are willing to yield to obtain what they want. When either party has all the leverage and no willingness to yield, there's no room for negotiation. That's (likely) the case here. Why?

When a boss gives an ultimatum (again, I'm not saying the boss is justified; I'm just stating a truism), the purpose is usually (always?) to remove the possibility of negotiation. Your boss has basically said "I'm taking away your trip, and will fire you if you don't fall in line and go to the conference." The ball is in your court. You can either go along with her, forfeiting your trip, or you can push back, fully expecting to lose your job in the process; that's the point of the ultimatum. Whether and how to push back (if you decide to do so) is up to you, but be prepared for the boss to make good on her ultimatum if you do so.

So I wouldn't treat it as a negotiation, as it most likely isn't one. This doesn't mean don't push back. It just means realize that doing so is basically invoking the nuclear option with respect to your current employment relationship, so make sure you know what you're doing and you've prepared fully for the fallout in advance (e.g. lining up a new job). Also it means making sure you don't stumble into getting fired on accident by assuming you can push back without repercussions.

What counts as pushing back?

Again, I'm not saying don't push back, I'm just defining what will likely be regarded as pushing back by your boss. The following are likely to be viewed that way:

  • Going over her head to her boss.
  • Going to HR.
  • Suing or threatening to sue.
  • Quite possibly even trying to persuade her to change her mind.
  • Anything other than doing what she says

Again, I'm not at all saying your boss is ethically or even legally justified

You may be totally justified in pushing back (I think you are, at least ethically--IANAL), but that doesn't change the fact that an ultimatum is an ultimatum: if you violate it, make sure you're prepared to accept the threatened consequences. So don't do it lightly, and make sure you're violating it only when and how you plan to: don't accidentally violate the ultimatum by treating it as a negotiation. It's (most likely) not.

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    Just to be 100% clear I'm not at all on the boss' side here. I'm just trying to help clear up a misunderstanding OP seems to be having in thinking this should be approached as a negotiation. I do think OP should get out of this job if possible. Lemme know if I can make this clearer.
    – bob
    Commented Dec 10, 2019 at 19:54
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    I think your definition of "negotiation" is stricter than most people's. Commented Dec 10, 2019 at 20:00
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    Almost done editing it. Will comment shortly when I am. Sorry, I write by editing a lot, and the downvotes have shown me there's work to be done.
    – bob
    Commented Dec 10, 2019 at 20:01
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    @bob I have a manager, and there's no doubt that he is doing a good job, but there are at least five people in his team who would be a lot more difficult to replace than the manager. The manager here has just arrived (and started stupid shenanigans as soon as she arrived). She is no loss to the company at all.
    – gnasher729
    Commented Dec 13, 2019 at 2:43
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    @Bob middle managers are much more replaceable than experienced developers.
    – DaveG
    Commented Dec 13, 2019 at 12:53

None of us can know for sure, that said this has the smell of something a new manager does to run people off so they can bring in their cronies. She could also just not like you. She might think that the output under the previous manager was not good enough, and thinks that the conference will help raise the bar.

Not saying that is true, just that she may be motivated by a similar idea.

  1. Don't let her take your PTO
  2. Try to figure out where she's really coming from, kill her with kindness, maybe she has things going on and is reacting poorly to stress
  3. Figure out who company is invested in, it's usually the manager, and continue to keep that in mind for any future conflicts
  4. You can't fight City Hall
  5. Being right almost never changes anything
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    The company has zero investment in this manager. Read the question.
    – gnasher729
    Commented Dec 11, 2019 at 18:39
  • How do we know there's zero invested in the manager? I don't see that in the question. We don't know whether she was promoted internally or brought in from the outside. Either way there will be investment, both in the interview process which can be lengthy for finding managers, and possibly in terms of training or just length of tenure at the company for an internal promotion, or in terms of relocation costs for a new hire. So either way there's likely a big investment in the new manager. Plus the ego investment: someone important likely chose them. Important people don't like appearing wrong.
    – bob
    Commented Dec 11, 2019 at 19:03
  • After all, why don't more incompetent managers get fired or demoted?
    – bob
    Commented Dec 11, 2019 at 19:03

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