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How to ask your boss for time off – Like a Pro

Estimated reading time: 5 mins

You need a vacation, or just a day’s leave, but you don’t know how to ask your boss for the time off. What should you do?

If you’ve recently started a new job, then this is a problem many people face. Or even if you have been in your job for a good while yet, some folks have an a*****e of a boss. Request vacation the right way and you have the best chance of it being granted.

Check the terms of your employment

The first thing to do is to take a look at the terms of your employment (your employment contract) to understand what you are entitled to. Start here. You should learn how much vacation you can take, and the procedure to request it. You might find the procedures on your intranet, or if you can’t find it there, try HR. Your co-workers may point you towards it.

The three-month expectation

For most people, and for most employers, there is an expectation that an employee works three months straight before taking vacation. Starting a job at the start of the summer can be a real challenge! The three-month expectation exists because most employees start on a probationary period – normally three months – even if it isn’t written down in your contract. This gives both employer and employee the opportunity to experience each other – and sometimes to provide a contractual get-out. Besides, it’s probably the case that you don’t start to build up vacation time until after three months, so you won’t be entitled to it.

But if you really must take vacation during the first three months then you’ve got to play it carefully. If you’re taking leave to sip champagne in the sun, then you’re almost certainly on a loser – that is if you’re honest about where you’re going. Of course, you can lie about your vacation and tell you’re boss that you have to bury your grandma – but remember that in this world of social media, your photos on the beach published to Facebook will be a dead giveaway!

If you really need to take vacation within the first three months, e.g. you really do have to bury your grandma, or take your kid in to hospital for an operation, then your employer could have policies for compassionate leave that apply here.

After three months…

…you’re in a stronger position to request leave. It doesn’t mean it will be granted though. Typically, your boss has to approve it – they are a gate-keeper to your Aruba trip.

Here are some guidelines when asking for leave:

  1. Check the policies. Read your employer’s vacation policy yourself – don’t accept being simply told it by your boss or co-workers.
  2. Check your travel dates. Make sure you’ve checked your travel itinerary – I goofed on one vacation because I hadn’t checked that my home-bound flight landed in the early hours of the day I was due to return to work, and I was not in a fit state to start back again. Luckily, I had an understanding boss and he okayed me taking another day off to sleep. You might not be so lucky! Vacation schedules during the summer months are so tight that you might run into trouble if you make a mistake.
  3. Check your employer’s key business dates. Don’t forget to do this. Your employer will have dates that are sacrosanct in the year, and no vacation will be granted during them. Such as at the end of the quarter. In my industry, these dates span the UK tax-period and it’s all hands to the pump.
  4. Sound out your boss. Way before you plan to take vacation, talk with your boss. For example, say that you have plans to go on vacation around July, and ask what dates would best fit the schedule. This way, you’ll most likely get the dates that your boss will approve, and avoid creating a problem.
  5. Give as much notice as possible. The more the better.
  6. Use the correct forms/intranet tools. Don’t just ask in person – make sure that your request is logged in a system. If your organization doesn’t use forms, then make your request by email, and insist on a response by email if your boss gives you a response by mouth.
  7. Don’t give too much detail about your leave. This might sound odd, and secretive – but your boss and co-workers don’t need to know you’re going to Aruba, or visiting Europe. I’ve heard of cases where vindictive bosses have denied vacation purely out of jealousy! Instead, simply share that you’re taking a trip.
  8. Don’t book anything until your vacation is granted. No matter how amazing the deals are, if there is a chance that your vacation will not be approved, then don’t book it. You might save on the price, but you might lose it all!

What if your boss doesn’t grant your vacation?

There may be good reasons for your request being rejected. If you’ve followed the guidelines, then the chance of this is slim. So ask for a thorough explanation of why – so you can correct your mistake and learn for next time. If the rejection is based on a schedule conflict with a co-worker, you could ask your co-worker if they are willing to change their vacation dates (who knows, they might not have committed to those dates in a booking yet). Until you ask, you won’t know.

There may be other reasons for your request being rejected. Maybe your boss is just an a*****e. Ask for the specific reason why your request was rejected. If you’re not compromising policy or your requested dates don’t conflict with the schedule, then there is no justifiable reason for the rejection. At this point, you could ask for HR’s involvement. If that isn’t an option, then ask your boss (again) for some dates that are acceptable, and look for a compromise.

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This post is part 7 of 8 in the series Managing Your Manager

About the author /


Simon is a creative and passionate business leader dedicated to having fun in the pursuit of high performance and personal development. He is co-founder of Applied Change, a Business Change consultancy based in the UK. Simon is also an Ambassador for Gloucestershire business. Simon is an Associate Member of the Chartered Institute of Professional Development.

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