10 Ways To Ask Your Boss For Leave

Annelise Moult

By Annelise Moult
05 Nov 2019

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1. Shower them with compliments

Whoever said the quote ‘flattery gets you nowhere’ has clearly never asked their boss for holiday leave – flattery gets you EVERYWHERE. One of the most successful methods is the compliment sandwich. Think of your request for leave as the filling and the big, juicy compliments as the two pieces of bread on either side. Your boss will be so enamoured by your kind words that they’ll almost definitely say yes to your holiday – it’s very hard to say no to someone who has just complimented your hair, clothes, shoes and family in such quick succession.

2. Make a detailed Powerpoint presentation

It’s a well-known fact that when you’re asking for something, it’s best to do it by way of a detailed and thorough Powerpoint presentation. The idea here is that you impress your boss with so many slides, transitions and animations that they can’t help but say yes to your holiday (I find the checkerboard effect particularly powerful). Make sure the presentation also includes at least 5 pictures of you photoshopped onto a background of your holiday destination, just to really drive the point home.

3. Write an original song

What better way to ask for leave than through the magic of song? Writing an original piece shows dedication to your cause, and who can say no to someone with the voice of an angel?! It’s important to sing loud and clear to drown out any attempts by your manager to yell ‘NO’ over the top of you. Bonus points if you perform with an instrument, such as a harmonica or ukulele.

4. Perform an interpretive dance

Much like the magic of song, the art of interpretive dance knows no bounds. Create a routine that is expressive and tells a story (of you on a beach in Greece or on a boat in Croatia – you get the gist). This should use large gestures and a LOT of floor space. Your boss will be so taken aback, they’ll say yes to your holiday just so you stop flailing your arms around.

5. Tell them it will increase productivity

If you can convince your manager that productivity will increase while you are not in the office, this is a sure-fire way to get that holiday leave approved pronto. This shouldn’t be too hard to do – there’s no doubt you’re currently an extreme distraction to your colleagues with all the singing and interpretive dance (see points 3 and 4), so your manager will have you out the door with an Out of Office on in no time.

6. Offer to bring back office snacks

In the majority of offices there is a snacks table, and team morale is significantly improved when that table of love is full. If you can promise that you will provide snacks for the team in the form of exciting candy and giant Duty Free Toblerone, your colleagues are guaranteed to rally around you and convince your boss that you NEED this leave. They’ll be counting down the days until you return, and they can indulge in all that chocolatey goodness.

7. Tell them your horoscope said a holiday is in the stars

Everyone knows that if it’s in the stars, it’s meant to be. Even if your daily horoscope doesn’t explicitly say you need a vacation, it‘s definitely still in there somewhere. Maybe it says you need a ‘change of scenery’, a chance to ‘refresh and reset’ or you should ‘take on a new endeavour’. These are all codes for ‘take a holiday’ and should be actioned ASAP.

8. Create a doctor’s certificate for urgent warm weather

If a summer getaway is what you’re after, just convince your boss that the doctor has ordered a healthy dose of sun to cure your pale and ghostly complexion. Put your Microsoft Paint skills to good use by creating a doctor’s certificate – funky word art and clipart images of beaches are very important here. There’s no way your boss will say no to a very legitimate medical document!

9. Tell them you dreamt they’d already said yes

Let’s face it, sometimes dreams can feel extremely real and leave you wondering if they’ve actually happened or not. We all know that people at work LOVE hearing about every single detail of the dream you had the night before so based on this, you should sit your manager down and spend at least 20 minutes giving them a detailed recollection of every minute of your vivid dream where they said yes to your holiday. By the end of the conversation, they’ll agree to your vacation just to get out of the conversation.

10. Do what everyone else does and just ask normally

As successful as an interpretive dance would be, sometimes it’s just as easy to have a face-to-face conversation with your manager and ask for the leave that way. If the timing is right and you have the annual leave owing, the chances are very high that they’ll say yes! Remember you’ve always got your original song as a backup plan!