As a leave policy I have 7 Casual, 7 Sick, and 13 earned leaves.

In the past, there was a crucial period going on for my team, to release a project, where I had no take. My part was done and tested to be all right. I did not have to do anything, and I had applied leave 2 months earlier for my cousin's wedding. But My manager got stubborn on me not taking the leave, as the team needs me (although my work was done). (I still went off...;), taking the risk). and now, whenever I ask for even a 1 day off, my manager makes faces, and never allows.

How can I politely request time off in a manner which is least likely to be denied when my boss has a history of refusing my holiday requests?

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    If you still left after the leave was denied, most places would have fired you. This is NOT an acceptable solution to the problem and it makes for further problems even if they don't fire you as you have experienced. You are no longer trusted.
    – HLGEM
    Feb 11 '13 at 14:21
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    I voted up to counteract the downvotes -- just because, as an aside, the OP admitted to unethical behavior does not make the question any less valid in my opinion. Feb 11 '13 at 15:07
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    I think this is more a matter of a conflict with you and your boss than a question about "how" to ask for time off. You are being totally reasonable here, but it could very well be that the "defiance" of taking time off when the boss had said "no" has caused the boss to lose face and now he is being vindictive.
    – Angelo
    Feb 11 '13 at 15:17
  • @RhysW, I agree with your answer for someone not the OP, I fear he has irretrievably burned his bridges with his bad behavior. The OP can try your question about asking when he can take the leave when the request is turned down, but even then, I suspect his boss will remain furious with him and will do everything he can to torpedo him (Although he might be forced to let him take a day off). Taking leave when denied it is a huge mistake and it is often not one you can recover from.
    – HLGEM
    Feb 11 '13 at 16:35
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    @RhysW Exactly what way could you put it to the manager to get the day off for the wedding. I know he may have been a good friend but I doubt they are going to change their wedding day for you. Feb 11 '13 at 20:35

It is important to take all things into consideration when asking for leave to make it as easy as possible for your boss to say "Yes".

  • Make sure to ask long in advance, this gives him a chance to plan around that and organize a temporary replacement.

  • Try not to ask for holiday right in the middle of an important / busy period. Asking for time off during the delivery of an important project is just asking to be denied.

  • If your company uses official holiday request forms be sure to use it. This makes sure there is a paper trail of you asking for the holiday and makes it easier for the boss to remember / store it for future use.

  • Where possible, make sure someone else knows what you're doing and how to do it, so if something pops up while you are away there is someone to deal with it. This may require a talk with your boss to organize.

  • Be firm. If you show you are always going to back down and not take holidays whenever they request they will do it more and more often

  • Be lenient. Weigh up the pros and cons, if you are just taking holiday off to sit at home and are only taking it for the sake of taking it then perhaps that is ok to you to cancel and come in and work if requested. Or perhaps its too important to cancel and you decide its more important to take it, e.g wedding. Being lenient can help because it shows your boss you are a team player. Just don't do it too frequently, its about balance.

  • Probably most importantly is that if this behavior persists then speak to your boss / HR and get the issue resolved. After all holiday is part of the compensation package, if your boss decided one day to pay you less you wouldn't stand for it.

The holiday is yours and you are entitled to it after all, just be polite about it.

If he is making faces and saying no all the time one thing you can do is say

If i can't take it on this date when are suitable dates that i can take it?

This puts the ball in his court, it gives him the chance to make a decision and he is not allowed to answer never, as it is against your contract (and in most places, the law) to give 0 holidays.

Of course, only say the above for those times when you don't mind when holiday is. For the times when you do mind, try to adhere to the points above.

If he consistently refuses you holiday for the times specified politely ask why. If he doesn't have a good reason and is saying no just to be mean, take it up with HR.

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