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 vacation. First, you should think twice before picking the right time to go for your next potential destination. For example, going to Greece in July seems amazing but might not be the best idea as it will be full of tourists (check my tips for Greece) and you might have a big work deliverable for that month. 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. 

Psst: As a project manager, these are the steps and procedures that I ask my team to follow. I promise you that they work ;)

Create a strategy 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 days approved if you are less busy, in a down period. 

  • Ask for your time off at least 2 months in advance (If you're asking to get time off between popular periods for vacations, you might ask even earlier.) 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. The organism 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.

  • While researching for the company's policies regarding your PTO, be sure that you have enough banked hours to get your paid vacation. Depending on the policies you might only be able to get your vacations a year after you started in the company or you might not have enough banked hours. Sometimes waiting a few extra days or weeks will allow you to have a fully paid vacations and it will diminish the back and forth with your boss and HR.

  • Before asking, do not forget to think who you are going to delegate your ongoing files. 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.

  • What ever you do, Do not buy plane tickets, book your hotel before asking your boss for permission for the dates you have in mind. If you do this, your boss will feel that yo are ambushing him or her.

Preparing this mini-plan in advance will show that you are prepared and that you will not leave your team in bad circumstances during your absence. This will not only reassure your boss but it will give your manager a few extra points for him or her to say yes!

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 for them. 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 manager 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 if you can take vacations on another timing. If your supervisor doesn’t propose another time, you should insist that you need vacation time and that you are willing to sit with them to find the best timing for the company. If you don’t insist 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 right away, and write and send a confirmation 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.

Start planning your vacation now!

Photo credits by Unsplash



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How to ask your boss for vacations