Hi I'm Karen and I am obsessing over whether I should ask for a vacation or not from my boss. She and I had a quarrel a few days ago because I expressed grief when she was trying to much to micromanage me and things were said, but later we made up by hugging it out. Things are still a little cold since then and I need to ask for a time off in December. In december, we get a week off during Christmas, plus, I will be taking the 2 weeks from this year and I am hoping that I can also take a week from next year. So a total of 4 weeks vacation. This is to go see my sister who I haven't seen in over 4 years who lives abroad.

Anyways, the point is, because of the souring of our relationship, I feel whatever I might ask for, she will always find a way to negate or say no (which she has been doing in the last few days).

So my question is how do you ask for a 4 week vacation from a boss who doesn't like you? Is there ways I can soften her up or persuade her?

Maybe it is also worth noting that we have a big project we are working on right now, which would be pretty much complete by the time of my vacation, just the last streak.

  • 2
    I feel it's relevant to say that you haven't "made up" if she's still making your life harder. You may have gone through the motions, but nothing has actually been accomplished.
    – Erik
    Sep 21, 2016 at 8:02
  • 2
    What is your locale? Local employment laws may be relevant to your question
    – rath
    Sep 21, 2016 at 8:16
  • 2
    Hugging it out? Really? Lets just say that I have never hugged it out with my boss.
    – Maarten
    Sep 21, 2016 at 10:41
  • "things are still a little cold since then". Just to throw it out there. Are things a little cold, or is the boss simply honoring your request not to be micromanaged. Giving you some space and micromanage you less? Not micromanaging might be hard for your boss. Might come over as being "cold" to you because of this. Or maybe you are so used to being micromanaged that the less micromanagement simply feels "cold".
    – Jeroen
    Sep 21, 2016 at 14:40
  • I don't do a lot of hugging at work, but when I have, I'm on good terms with the person.
    – user8365
    Sep 21, 2016 at 21:35

4 Answers 4


It really doesn't matter if they like you or not. You are contractually entitled to some number of vacation days per year. Unless there are specific reasons why you shouldn't take vacation at specific times (for example, when there is a crash-priority all-hands-on-deck crisis), getting vacation approved is not a big deal... especially if you make the request several weeks in advance and make sure there is someone who will handle your responsibilities while you are gone.

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    I miss a part where you acknowledge that the OP wants to take days off that s/he has not even earned yet. That seems to be the point where s/he needs approval, getting approval for something that you aren't entitled too is a big deal.
    – nvoigt
    Sep 21, 2016 at 9:55
  • as long as she has the vacation days it shouldnt matter, should it? Doesnt state anything about her days or whatever so I am assuming she still has days left. Sep 21, 2016 at 12:39
  • Not all employers allot vacation days as the are earned. If I want to take all of mine at the start of January, my employer has no objection to my doing so. If you're on an incremental plan, of course "borrowing" time will require special permission, but I presumed that went without saying, just as taking time off beyond your vacation allotment would.
    – keshlam
    Sep 21, 2016 at 12:43
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    Hm, maybe you are right... " I am hoping that I can also take a week from next year." for me means taking a week in December basically going "negative days off" to be balanced with next year's refreshed days off. It may however just mean that one of the vacation weeks is in January taken with normal earned days off... in that case I really don't know what the question is.
    – nvoigt
    Sep 21, 2016 at 13:05

You have to ask because if you don't ask, you don't get.

You are obsessing about asking, because you are worried/scared that the answer you get is "no"?

I think you did a pretty good job of scheduling your vacation - the Christmas season is not particularly busy. The only fly in the ointment is your big project, which could stay live well past the expected date of completion. You and your manager probably need to plan for that contingency. And you need to be able to suggest someone to take over from you when you have to go, or establish shortly before you go on vac that the project is sufficiently close to completion that she can well afford you going on vacation. You're not going on vacation if she has worries of her own that she can't resolve without you.

Be prepared to compromise. You may ask for four weeks, but you get three weeks.

As for your dispute with your manager, what's done is done and that's water under the bridge. Especially if the dispute was conducted in a respectful/professional manner, a satisfactory resolution was achieved and no personality conflicts were injected into the dispute.

Happiness on the job is not whether you have disagreements, it's how these disagreements are aired and solved, or at the very least managed until some sort of resolution is achieved.


A good answer already, but it does pay to be on good terms with your boss, particularly when you will be asking for a week of leave from next years allotment, which realistically is asking for a bit. A months holiday is hard to cover sometimes.

While this might sound like a blatant bribe for affection (which it is). A box of chocolates and a nice card of appreciation are very rarely looked at badly, and are a pretty general peace offering. It's hard not to feel kindly to someone while eating their chocolate and you get to put the card in a prominent position so your clients can see that your employees love you.

  • A good advice in general but in this case the manager might not have the authority to grant a week's leave out of nowhere, which means she'll have to clear it with upstairs... so the OP will need a lot of chocolate.
    – rath
    Sep 21, 2016 at 8:19
  • @rath at least she'll hopefully 'try' and clear it upstairs which is a whole lot better than recommending they decline. And in any case it will help heal the rift which in itself is a good thing.
    – Kilisi
    Sep 21, 2016 at 9:56

You cannot really change your relationship with your boss on short notice. You will need to employ some people skills. Be nice, pick a time and date where your boss is not stressed out or on the run. Then ask him nicely.

Grammatically speaking, if you ask a "Yes/No" question, you will get either Yes or No as an answer. So if you ask "Can I get three weeks off?" Chances are, your boss will go for the easy "No".

If you want to dodge that "No", ask a question where "No" is not grammatically correct. "I would like to get three weeks off. I realize this is a stretch, so I came to ask what I can do so we can make it work." There is no way for an easy "No" now.

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