How to Ask for Some Well-Deserved Time Off (Examples)

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 honor, 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 anything other than a 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.

The difference between paid and unpaid time off

Paid time off and unpaid time off are processed and used in different ways.

Whereas accrued PTO is used for shorter-term requests, such as vacation days or sick days, UTO is usually uncapped to an accrual, which means it’s useful for longer absences. These can include extended leave, emergency leave, medical leave and, in some cases, maternity or paternity leave. The Family and Medical Leave Act legally entitles covered employees to be provided with this where needed.

It’s generally easier to get PTO approved, as longer periods of unpaid leave might affect contractual entitlement and benefits. Therefore, a formal request for this tends to be more heavily scrutinized and should be only granted in line with employee handbook stipulations.

Good reasons to ask for time off

There are many good reasons to ask for time off, all of which we might need to use from time to time. Here are six common types of leave request:

Tips for asking for time off

So, how do you go about asking for some much-needed time off?

1. Familiarize yourself with company policy

The most important thing to do before even considering time off is to familiarize yourself with your company’s policy regarding time off work.

Remember that hefty handbook you were handed on your first day and shoved in the back of your drawer? 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.

2. Start 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 organization and be thankful that you gave them plenty of notice.

On that note:

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’re 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 favor 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 quite 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 specific procedures 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, they 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 your boss when they’re not frantically typing away at the keyboard and don’t have that frustrated look on their 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 — perhaps one of you can take Christmas off and the other New Year.

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 their 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 common 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, an HR 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’re capable of working from home and you 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?” or “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.

Email samples for requesting time off work

Submitting your request for time off can be nerve-wracking, especially if not much advance notice is being given. Here are three sample time off request emails that you can use:

Sample PTO request email to request vacation time

Subject line: Vacation request

Dear Roger,

I hope this email finds you well.

I am writing to request a period of vacation with my family, from June 3 to 14. I have enough accrued PTO days for this request.

Before I leave, I will ensure that any outstanding tasks are completed, and that anything that cannot be closed off is handed over appropriately to Peggy Olsen, who will handle any urgent matters until I return.

Thank you for considering this request for vacation leave. Please let me know if you require any further information, as I will be happy to discuss it further if needed.

Warm regards,

Don Draper

Sample email requesting time off for personal reasons

Subject line: Request for personal time related to house move

Dear Harvey,

I hope this email finds you well.

I am writing this email to request one week of paid leave, from July 1 to 5, so I can focus on a house move that I am completing.

I appreciate this request is a little short notice and isn’t a regular request for time off. However, it will enable me to focus fully on this important responsibility without it impacting my work.

Before I leave, I will ensure all responsibilities are closed off. I have arranged for my colleague, Rachel Zane, to attend to any urgent or pertinent matters that arise while I am away.

Thank you for considering this request, and please let me know if you would like to meet me to discuss it.

Warm regards,

Mike Ross

Sample email requesting time off for medical reasons

Subject line: Sick leave request

Dear Michael,

I hope this email finds you well.

I am writing this email to request medical leave.

As you are aware, recently I have been feeling unwell and have sought medical advice. My doctor has advised that I take two weeks off to allow me to recover fully. Therefore, I am requesting sick leave from tomorrow, June 17 to 28, inclusive.

Apologies for the short notice of this request, but I hope you understand that my health and recovery must take priority at this moment. I will ensure that my tasks will be covered by my colleague, Dwight Schrute. I will also be available via email for any urgent matters.

Please let me know if you require any further information or documentation from me at this stage.

Warm regards,

Jim Halpert

Final thoughts

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!

This article is a partial update of an earlier version originally published on January 5, 2018, and contains contributions by Mike Dalley.

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