How to successfully ask your boss for vacations in 3 simple steps [+ free download]

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 paid 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 days.

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

Here are a few tips to think about before you request vacation days. 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 ;)

I know this article looks a little intimidating but don’t worry, these are super easy steps to follow.

If you are looking for more resources on how to travel while having a full-time job, check out more tips like these in my plan from the office section!

Create a strategy BEFORE storming into your boss’ office

Define your Dates

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 instance, 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 give your leave request to your boss. If you are working on a project, avoid leaving during the peak period. You will maximize your chances to get your vacation days approved if you are less busy, in a down period. In other words, try to work around the busiest dates workwise.

Check if someone else from your team members is also on vacation. Why? If 2 other people are also going on vacation at the same time, you might not be able to distribute all of your workload you will be also adding a lot of stress to your team. You will need to be a team player. Communicate reasonably and professionally to ensure that your teams’ schedules line up. 

If you just started a new job and you did not negotiate your vacations in advance, you might want to think twice. HR experts advise against taking time off during your first three months on the job. During this time you are still on probation and it might send the wrong message to the company,

Research your company’s policies

Familiarize yourself with your company's policies regarding your PTO (paid time off). You can check these by reviewing your employee handbook or asking your human resources representative for more information about your company’s vacation policies. Who needs to be the recipient of your request?

In some cases, you might need to request time off well in advance. For a long vacation, you may need to ask for ample notice, for example, you might need to ask up to 2 months earlier. While if you are only taking a Friday off to have a long weekend you might only need a week’s advance notice.

The important point here is not to ask in short notice. You don’t want to ask your boss 1 week before leaving on your 2-week vacation. This might jeopardize your relationship with your boss and the chances of getting a yes answer. Research shows that requesting time well in advance is one of the biggest factors in vacation requests approval rates.

While researching the company's vacation policy be sure that you have enough banked hours to get your paid vacation. In other words, play by the rules! 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 all the accused PTO needed for your break. Sometimes waiting a few extra days or weeks will allow you to have a fully paid vacation and it will diminish the back and forth with your boss and Human Resources.

Clearly state if you are using your PTO days, personal days, extended public holidays or even unpaid leave. Do some research if you are allowed to take different types of time off such as sick days or personal days as vacation days. Are you allowed to take unpaid time off if you max out on your PTO? Sometimes you might be requesting a time that is a mix of all! I know I have done a mix and match of statutory holidays, personal days, banked hours and PTO!

Don’t forget to check what happens if you don’t use all of our vacation days in a calendar year – do they roll over or disappear entirely? You don’t want to be leaving any vacation days unused! If you are going to lose some annual leave days add this to your discussion with your manager. This might help you get an approval.

In some companies, you must inform your supervisor but other companies have a strict protocol and a long list of people who must be noticed. Have this information ready for the last step.

Ask, don’t tell

Whatever 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 you are ambushing him or her.

Prepare your vacation plan

Before asking, do not forget to think about who you are going to delegate your ongoing files to. Unfortunately, the company's 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 for you to leave stress-free. Don’t leave this to your supervisor to do this part of the work.

Giving this information to your boss will give them confidence that work will carry on and not collapse while you are gone.

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 also give your manager a few extra points for him or her to say yes!

For example, my mini-plan looks like this:

I will take 5 vacation days from 1 to 5 July, I have enough PTOs. I will delegate my work to my Associate project manager. I will send her an email with the list of things to do and I will also hold meetings 1 week before leaving so she knows what to do. I will be reachable for emergencies if needed, you can call my personal phone. I have checked and no one else from my team is away during that period so it will not create an additional workload for the team.

3 Things to say WHILE you are asking for your vacations

You should always ask for your vacation face-to-face first and then immediately after, you should send an email to leave a paper trail or make the official annual leave request right after talking to your boss. Doing the PTO request in person will be quicker, easier, and more effective. In fact, Harvard Business Review came to the conclusion that in-person requests are 34 times more successful than email. This means that if there is a negotiation to be had with your boss you will have more power of persuasion

Timing

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. If you are working remotely, you can send a friendly chat or an informal email.

Also, If your director is on his annual vacation, don’t interrupt their time to ask about your vacation, this is just common sense.

What to ask

For example, ask your manager if going on vacation for 2 weeks fits in the company's plan. To help your supervisor say yes, present her/him the mini-plan that you did by following the steps in the first section above. This will reassure her/him, and put a positive note on a yes answer.

Also, say why you need time off without going into your personal life details. Using the word “because” will increase your chances of saying yes so use it! An example would be I’m requesting time off because I would like to go see my family.

Did your Manager say no? Don’t worry!

Firstly, don’t panic! It’s essential to understand why.

If your boss decides to say no, ask the reasons. Is it because of an important project coming up? The person does not agree with whom you are delegating your job? Find out the reason.

You have now entered a negotiation place. Remember, open and respectful communication is key.

Ask if you can take a vacation at another time. 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 time for the company. If you don’t insist there is a chance that you will never get your time off approved! This rejection should be handled well, try to understand their point of view and work around this.

Is your company not a fan of vacation? Are you one of the 47% of Americans who don’t take all their vacation days because it’s hard to get away from their jobs? Here are some numbers to give your boss. (Besides, changing companies and finding a new job that allows a balance between work and personal time). Taking vacation eases job stress, reduces risks of depression and enhances your performance. In sum, Less stress = bigger performance. Vacations not only enhance your performance but also ease burn-out. Ernest & Young conducted a study that concluded that for every 10 hours of vacation performance ratings improved by 8%. BOOM! Give these numbers to your employer and you are set.

Don’t let the company culture or manager shame you to take vacations. Time off is key to your well-being and work life balance. As long as your policy states that you’re entitled to days off, you can and should be able to take them.

Psst: In my opinion, no job is worth missing out on live adventures of moments with close ones, we already had that during the horrible Covid-19 pandemic.

Yess! Your boss said yes, Now what?

Complete your formal vacation request

Since you asked your boss face to face, now you need to leave a paper trail. An email should be sent right after your conversation. The email should be a summary of your request with the exact dates of your planned vacation. To avoid confusion, it’s a good idea to state the date of your first day back in the office. It should also have total days off.

The second step should be to complete your formal request per your company PTO policy (you already did your research in the first section). Do you need to add your vacation days through your company software, or a form or start writing a formal vacation letter request right away (I have provided an example below)? Try to follow the right procedure, you will not want your application to get lost after requesting your time.

The advance notice should be very clear and concise. Add the dates and the duration of your vacation if you will be available to take any calls or to respond to your email. On your vacation leave, it is a good idea to say that you already agreed with your boss. For example, for me, I need to add my vacation request through the intranet and I need to fill out a form. I would write in the description that this matter has already been discussed and approved.

Simple vacation request email example

Concise Subject line: [your name] Vacation request from [dates]

Hi [Name of your boss]

As previously discussed, I'd like to request vacation time from [dates]. I would like to travel to [location - you don’t have to disclose it]. I'll use 40 hours of accrued time for this request, and I confirmed I have enough time in my bank to accommodate this. I have also checked with my team and there is no vacation overlap. I will delegate my work to my [name and title of the person]. I will send them an email with the list of things to do and I will also hold meetings 1 week before leaving so they know what to do. I will be reachable for emergencies if needed, you can call my personal phone.

Please let me know if you have any questions, and thank you for reviewing my request.

Thanks.

Acknowledge the reply

Once you receive written approval of your vacation you can write a reply email, thanking your manager for granting your request.

Take this opportunity to ask for clarifications and instructions on making the process more seamless for the company. Maybe your manager will ask you to complete some important tasks before leaving.

Prepare to go on vacation

Tell your coworkers that you will go on vacation, especially the ones that will cover for you while you are gone.

At least 2 weeks before leaving, start doing your vacation checklist. This includes a guide of the steps to follow while you are away like who will be in charge of your work and how to access any documents that might be only in your possession. And of course complete all of your ongoing tasks. If you make covering for you as effortless as possible chances are that your boss will say yes to your next vacation again. 

Above all, don’t be afraid to ask for your vacation! Everyone needs a break from time to time. This time off will allow you to be more productive when you come back! I hope this guide helps you ask for your vacation the right way. Don’t forget, to give advance notice is the key.

So, what are you waiting for? The next step, start planning your vacation now!

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