Extended vacations vary from sabbaticals lasting many months to just taking off more time than your company typically allows. Requesting an extended vacation can be awkward for both you and your boss. Chances are you have pressing reasons for your extended vacation, or you wouldn't put your boss in such a difficult position. For your boss’ part, she probably would love to help you, but your extended vacation might be hard for the company to weather. Be considerate of the difficulty your request poses.

Planning

Draft a plan for your extended vacation, being as specific as possible. Include details about how long you will be gone, how much work you can accomplish while out of the office, what chance there is of you not coming back at all and any other details that can help your boss process your request. Try to anticipate your boss’ concerns. Potential issues might include what projects will have to be put on hold, which employees can fill in for you and whether you'll be willing to forego pay and benefits for the duration of your extended vacation.

Meeting

Ask for a private meeting to discuss your request. Explain your plan and offer clear assurances to counter your boss' worries. Be understanding of your boss’ predicament. For example, your company’s vacation policy might prohibit extended vacations, making it impossible for your boss to approve your request.

Compromise

If there is a significant problem with your plan, try to devise a workable compromise. For example, perhaps you can ease the workload for others by working overtime before your departure date or coming in occasionally during your vacation. Another option is to drastically reduce your hours instead of taking a vacation. For instance, a work-sharing arrangement involves two employees working part-time to do the tasks of one typical full-time worker. Or perhaps you can try non-traditional work hours or telecommuting, which will allow you to work during more convenient times. Finally, you can offer to take the extended vacation in lieu of a promotion or salary increase.

Considerations

Prepare yourself for a rejection. An extended vacation might be too difficult for your company to bear. If taking an extended vacation is a necessity, you might need to leave your job. If possible, help your boss find and train your replacement before you leave. Another possibility is postponing your extended vacation until a time when it is easier for the company to compensate for a missing employee.