How to Ask for Some Well-Deserved Time Off Work

Day off work written in diary

Whether you’re dreaming of tanning on a beach margarita in hand or planning time off for that operation you’ve been putting off for a while, you must first ask your boss for leave. In an office where overworking is a badge of honour, even if holiday allowance is part of your contractual agreement, it can still be a nerve-wracking task – especially if you’re dealing with a bad boss. You don’t want to be seen as a non-team player or not as committed to your work as others. So how do you go about getting your holiday approved?

We’ve got you covered with these top tips that will set you up for only a positive answer so you can get the time off that you deserve.

Tips for Asking for Time Off

1. Get Familiar with Company Policy

The most important thing to do before even considering time off is to familiarise yourself with your company policy. Remember that hefty handbook you were handed on your first day and shoved in the back of your draw? It’s time you pulled it out, dusted it off and read through the holiday rules. If you’re working for a company that’s quite laidback, ask around and find out what the norm is before you approach your manager and make a complete fool out of yourself.

2. Get Planning at the Beginning of Your Allowance

It’s the start of a new year and time to create a resolution and get planning when your new holiday allowance comes in. If you know you have a wedding to attend at the end of the year, for example, plan ahead and request the time off well in advance. Your boss will admire your organisation and be thankful that you gave him plenty of notice.

3. Give Plenty of Notice

Dropping your request on your boss’s desk a week before you plan to go on holiday will likely get you a big fat ‘no’ and probably a black mark against your name! Make sure you give plenty of notice to ensure a smooth transition of responsibilities for when you are away. Your manager will appreciate the warning and will value you more as an employee.

4. Ask, Don’t Tell

Don’t be the employee that mentions in passing: ‘By the way, I’m going to Dubai in two weeks so I’ll need the time off!’ You’re asking for approval, not telling your employer what you’re doing. There may be a very good reason why you’ll be needed at that time and a colleague may have already booked the same period off. Instead, say something like: ‘I have some vacation time coming and I’d like to take a week to travel with my family. Would the week of January 15 be a good time?’

5. Don’t Ask for Time Off During Peak Season

If you work in an industry like travel where the peak season is throughout the entire summer period, it’s logical that you shouldn’t book a long holiday off during this time. You’ll not only be disappointing your employer but you also won’t be doing yourself a favour either, as you’ll have a large pile of work waiting for you on your desk when you get back (and probably a few problems, too!). If there’s a reason why you need the time off, like a wedding or another big life event, make sure you arrange your schedule accordingly and put your request in for your leave of absence well in advance.

6. Get Approval in Writing

It’s one thing getting verbal approval and another having it in writing. Ensure you have proof of when you asked for the days off and of the consent to your request. Most companies usually follow a procedure where they need a written request, so it’s best to abide by the rules and not interrupt your boss during a busy period to ask for leave.

7. Delegate Your Work

It’s almost impossible to get all your tasks done before you go away on holiday and, more often than not, that important client has a request the day that you decide to go away. The answer to your problem is to delegate correctly. Make sure all the important stuff has been completed before you go away and give your colleague a clear handover with all the possible information they may need. Your boss will also be much more thankful that you’ve taken matters into your own hands, knowing they won’t have to worry about your duties when you are away.

8. Be Flexible

It’s important to be flexible when asking for time off. Booking your tickets before actually putting in the request at work is a rookie error. Although your boss is super cool, he might not be the one making the final decision and you may end up with a pair of useless and very expensive tickets – not a great scenario, right? So be flexible with your dates and always make sure you’ve got the all-clear before you book your well-deserved time off.

9. Ask at the Right Time

Asking at a suitable time is ideal! You don’t want to catch your boss in a bad mood at the end of a busy day where he might just take his frustration out on you. Plan your timing well and approach him when he isn’t frantically typing away at the keyboard and doesn’t have that frustrated look on his face.

10. Play Fair

If you’re in a working environment where only one or a few of you are allowed time off at the same time, play fair! Don’t be that jerk that books every Christmas and New Year off. Nobody likes that guy. Discuss the time off with your colleague if you both want the same leave and come to some kind of mutual agreement.

11. Pull the ‘I Can Still Be Reached by Email or Phone’ Card

If your work relies on a computer, which 99% of jobs these days do, then you can easily pull this one out of the bag. Your boss might start having a panic attack if you’re his right-hand man and are out of touch for two weeks. Relieve their stress by letting them know that you’ll be at the end of a phone call or an email away if needed. Just make sure that you actually stick to your word and keep in touch, otherwise you’ll have a very angry boss to return to work to.

What to Do in Specific Scenarios

There are a few scenarios that will leave you wondering how you should ask for time off. We’ve covered the most popular ones below:

1. If You Work Remotely

Many people that work remotely worry unnecessarily about asking for time off. You’re still entitled to paid leave and all the other benefits that are listed in your employee handbook. Janice Cadieux, human resources specialist at Clinical Computer Systems in Elgin, Illinois says: ‘Remote employees may have an opportunity to plan their own schedules, while some are firm on a set schedule and must be available during specific days and hours. Know your company's policy and openly communicate with your manager.’

2. If It’s Outside Your Normal Holiday Allowance

Big life events like weddings, honeymoons or the birth of a new family member all involve extended holidays which may require time that’s outside of your holiday allowance. Don’t let work get in the way of these events just because you’re only allowed two weeks off at a time. Your employer should be understanding; if you give them ample notice, there’s no way they’ll deprive you of enjoying your life outside of work, too.

3. If It’s an Emergency

Emergencies are unexpected; hospital appointments, accidents and deaths in the family all require urgent time off. In these circumstances, employees tend to get even more stressed out by deciding how to tell their boss. The answer is really simple: tell the truth. Bosses are usually understanding and sympathetic in times of emergency. If you are capable of working from home and have the ability to offer to do so, they’ll appreciate the gesture, even if they insist that you should rest.

4. If Your Request Is Rejected

If your request has been rejected, there’s usually a logical reason behind it. It could be the fact that you didn’t abide by company policy and give ample notice. Either way, don’t be afraid to question the decision in a calm manner. Consider following up with questions like: ‘Can you help me understand why this request wasn’t approved?’, ‘It sounds like you’re unhappy about this request. That was certainly not my intention. Can you help me understand where we got our lines crossed?’ or ‘Is there a time that would work better for you?’

5. If You Just Started a New Job

Being the newbie can be difficult to judge how the holiday system works. You don’t want to seem like you’re not dedicated, but you really need a day off to go to the mechanic or a week off to visit your sick aunt. Whatever the reason, don’t be afraid to ask – just know the balance and don’t overdo it. It’s wise to not ask for time off at the beginning of your employment when you’re still learning the ropes and getting to grips with your new workplace. However, if an emergency arises, make sure you discuss it with your new boss and get approval.

Asking for time off doesn’t have to be stressful. If you follow the above tips and have an honest relationship with your manager, you’ll be truly missed rather than resented when you plan your next trip away!

Have you had a hard time asking for time off before? If so, let us know what happened in the comments section below…