How to successfully ask your boss for vacations in 3 simple steps

You’ve set your mind, you want to go explore a new country for the month of July, you are going to ask your boss for your time off and you feel great about it! Hold your horses for a minute, there are a few things to consider before you go ask your boss for your well-deserved time off. First, think twice before picking your potential destination. For example, going to Greece in July seems to be amazing but might not be the best idea as it will be full of tourists (check my tips for Greece). Nonetheless, here are a few tips to think about before asking your boss for some time off. I've broken it into 3 simple steps, before you ask, while you ask, and what to do after you've asked for your time off. 

4 things to do BEFORE storming into your boss’ office

  • Are you going on vacation to a specific event or are you flexible? Showing flexibility with your dates might give you some extra points while negotiating your vacations. If you are going to a specific event, tell your manager, he/she will understand. For example, you cannot be flexible with dates when leaving for your sister’s wedding!

  • If your vacation dates are flexible, think about the best timing (work-related) to ask your boss. If you are working on a project, avoid leaving during the peak period. You will maximize your chances to get your vacations approved if you are less busy, in a down period. 

  • Ask for your time off at least 1 month in advance. Check out your company's policies regarding your PTO. In some cases, you might need to ask your time off well in advance. The important point here is not yo ask your boss 1 week before leaving. This might jeopardize your relationship with your boss and the chances of getting a yes answer. Project Time Off compiles some key points on why planning your vacation well in advance is one of the biggest factions of vacation approval rates, find out more here.

  • Before asking, do not forget to delegate your ongoing files to the right person. Unfortunately, company day-to-day won’t stop during your absence. Therefore, think about the best person you want to delegate your work to. This person must be qualified enough and must be trustworthy in order for you to leave stress-free. Quick tip: do a mini-plan. Show that you have thought this through to your boss.

 Computer near a bridge with the sentence work hard. Travel Harder. It was used as an illustration to ask your boss for vacations in 3 simple steps.

3 Things to say WHILE you are asking for your vacations

  • The timing of your request can be key. Go and see your supervisor when the time is good. If your boss is in a bad mood or s/he is running around like crazy, you better wait for the next day. 

  • Ask your boss if going on vacations for 2 weeks fits in the company's plan. To help your supervisor say yes, present him/her your mini-plan. This will reassure her/him, and put a positive note on a yes answer. 

  • If your boss decides to say no, ask what the best time would then be. If your supervisor doesn’t propose another time, you should insist that you need vacation time at this specific date or otherwise, there is a chance that you will never get your time off approved!


Yess! Your boss said yes. Now what?

  • Fill out your vacation request, and send an email. Once again, check out your company’s policies in term of asking for your time off. Try to follow the right procedure.

  • Tell your coworkers that you will go on vacation, especially the ones that will cover for you while you are gone.

  • At least 2 weeks before leaving, start doing your vacation checklist.

Start planning your vacation!

Photo credits by Unsplash


How to ask your boss for vacations