Asking for personal time off from your manager can quickly turn into a delicate situation, which can turn your otherwise positive image in their eyes into a less than positive one. Occasions like these are never easy on the person who needs to ask, especially if they also want to ask for paid time off. On one hand, you really do need to take that leave, in order to settle your personal issues and be able to work more efficiently when you return on the job. But on the other hand, you also need to make sure you put it very carefully, so that you don’t leave your company thinking you’re disinterested in the work. That’s why we’ve put together this short round-up of info on how to ask for time off, with tips on the precise questions you can ask to help the conversation go down smoother.

Things to Consider Before Asking for Paid Time Off

First of all, if the introduction above seemed a bit unfair, let’s get this settled: there’s of course nothing wrong with asking for time off if you still have free days remaining from your vacation. Paid free days are a right bestowed upon employees on almost every type of contract, so it’s well understood that you’re supposed to get it before the year expires. However, it’s still up to your company’s managers to decide on whether it is a good time for their employees to leave or not, considering the bigger picture of schedules and so on. Also, your personal manager (whom you directly work with) may not see your request kindly if your work performance has been poor lately.

This is what you need to consider (and solve, if necessary), before asking for the wanted time off:

• How was your performance lately? If your performance wasn’t that good and you know that there is a time approaching when you will need some time off, then the best thing to do is to strive to improve it before actually asking for the paid time off you want. If you don’t have enough time, at least come up with a plan for improvement and show it to your manager before discussing your request.
• What is the protocol of request and approval for time off? Make sure you have this taken well into consideration before expecting to have your request automatically approved. Is there a 30 day heads-up required? Who else needs to sign off on your request besides your direct manager? Try to respect each detail of the rules before expecting your wish to be fulfilled.
• Is everything left in order for a seamless transition in and out of office? Don’t leave any task still unfinished, make sure the people who will fill in for you understand your routines and procedures (in order to make their jobs easier as well), and you will return from your paid leave with an intact professional reputation. Also, if everything is left in order, you won’t be bothered by endless emails or phone calls while you’re away.

Recommended Questions for Your Manager (When Asking for Time Off)

Therefore, the points described above are precisely the way to start thinking about how to break the news (and request) to your manager. After you find your own answers to these questions, you’re ready to talk to your manager about taking some personal time. Based on what your own conclusions look like, these are some alternate ways and starting points for how to ask for time off:

• ‘I finished …. and laid the groundwork for the upcoming … project as well. I think things would run smoothly if I took about X days (or weeks) off in the upcoming period of time. Do you think that’s a bad idea, for any reason?’
• ‘Are you content with my recent levels of productivity? Is there anything you think I should consider for improving?’ After noting details of the answer, ask: ‘How would you feel about my taking some time off in the next few weeks / next month etc.?’
• Based on all the holiday schedules of other employees: ‘When do you think would be the best time for me to take some time off in the upcoming period, when my presence will be required least? I would like to see a busier time taken to the finish line first, and take personal time during a calmer period.’

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