How to ask for vacation time without annoying your boss

How to ask for vacation time without annoying your boss

You know the feeling.

Your palms are sweaty, your mind is whirring, and you can’t seem to think straight.

Asking for vacation time can be scary. You want your boss to say yes, but you don’t want it to appear that don’t care about your career.

Last week I shared how I traveled overseas to 8 countries in one year AND had a successful work year. Today, I’m sharing my tips for successfully asking for vacation time.

Why am I an expert on this topic?

I’m so glad you asked!

In 2015, I traveled to 8 countries AND still managed to have a successful year at work.

While on the job, my dedication to work was never questioned… Even though I traveled to so many countries!

To top this off, the year after in 2016, I traveled to 3 countries in the space of 6 months AND took 3 domestic Australian holidays.

Suffice to say; I’ve had the “taking vacation time” conversation many times over with my boss.

Are you afraid of asking for vacation time?

Well, my friend, read on…

asking for vacation time

1. It all begins before you ask

I’m not going to lie or provide some fluffy BS article about asking for vacation time.

In all honesty, having an honest relationship where you can regularly take vacation time without negatively impacting your career starts before you ask.

It starts as early as possible.

The work starts before you get a job…

If you are in the process of applying for a job, or are on the look-out for a job, find out what your potential manager is like.

How flexible is this person?

Do they care about work-life balance?

Do they take their vacation leave?

Hell, you can even ask in your interviews!

Don’t want to seem too lazy?

Ask about workplace flexibility. Are there programs or initiatives to encourage work-life balance?

If you’re already in a job, it still starts before you have “the conversation.”

If you’re new in your job, sniff around to figure out how flexible your boss seems.

See how readily others go on leave.

How much notice do they need?

Do your teammates complain about not being able to take leave?

If they don’t – chances are you’re okay!

If they do complain… You’ve got a lot of work ahead of you, so read on to point 2.

If after all this, you’re still not sure… ask!

You want to establish an honest relationship with your boss.

You want to be clear about your career goals AND how important your personal life is.

2. You need to work hard

I’m not going to lie – your boss will only be comfortable with you going on leave often if they trust that you take your job seriously.

Establish an honest relationship.

If you belong to the group of people whose manager or department is strict about leave, you’ll need to prove your ability to take your job seriously and take everything you work above and beyond what’s expected.

Be present all the time.

Take pride in your work.

Always be prepared and organized.

Show that when you go on vacation, everything will still work like clockwork. You don’t want things going haywire the moment you leave for your vacation.

Make it easy for teammates or your manager to take over your work in your absence.

Is there anything you can DO for them in advance? You want it to be easy for them to look after your work when you’re on vacation!

3. Prepare to ask

Check in advance how your boss wants you to approach leave.

How far in advance do you need to book in leave?

Are there certain busy periods?

Do you need to check with other teammates?

Do you need to check with your manager’s leave?

4. “The conversation.”

Now on to the actual conversation, where you’ll be asking for vacation time.

For me, travel is in my every day… So these conversations happened during my regular catch-ups with my boss.

It’s good form to give as much notice before you intend to take leave. This way, work can be planned around your absence.

This depends on where you work and how much notice is needed.

It’s all in the framing

If you’re taking off a couple of days around a public holiday, frame it as “I was hoping I could take a couple of days off around X public holiday.”

It also helps to mention how the office is usually slow around public holidays as other people are likely taking leave too.

If you’re not taking leave around a public holiday, then it’s best to word the conversation around taking your mandated vacation time.

If you’ve planned it to fall during the quiet period or around the team’s leave, also mention that too.

After all – you’ve taken into consideration business needs!

Thoughtfullness during this conversation is super helpful, as it shows you care about your team and the work that you do!

If you haven’t already, check with your manager whether they’re taking leave around that time

Every business is different, but the team I was in always had one team member around at any given time.

You want to make sure you’re taking in consideration your work needs when you’re planning your leave and super busy periods.

It depends on your business – if there are certain times of year that are blacklisted, don’t propose leave during this time!

Discuss or propose what you’ll do to minimize work for your teammates

If you know you’ll need your manager or teammate to cover something while you’re gone, it always helps to be prepared in the discussion to mention what you will do to make this as easy as possible.

It may be too early to know (i.e. your planned leave may not be for months) but it always helps to mention you’ll do X, Y, Z before you go so your boss knows you’re not going to leave the team in the lurch.

5. Taking leave is part of work-life balance

It’s important to spend time with family or to relax by yourself.

As someone who has traveled a bucket load, I always managed to approach the topic of taking leave without sacrificing my career progression.

If you want to lead a life of travel AND keep your full-time job, make sure you:

  1. Check out the team you’re about to join to see how flexible they are
  2. Prepare before you ask your manager:
  • How much notice do they need?
  • Are there certain times of year you need to avoid?
  • Do you have to make sure you don’t take leave at the same time as your teammates/boss?
  1. And before you go, make sure you tie up all loose ends and make your teammates and manager’s life easier when you’re gone!

Asking for vacation time without annoying your manager can be done – it takes a bit of preparation and an open channel of communication.

If you do a good job at work, chances are your boss will be all too happy for you to take that much needed time off!

Did you enjoy this post?

Make sure you check out the other posts in this series:

Part 1: how I traveled to 8 countries in one year AND kept my career 

Part 3: Keeping the travel mindset in your everyday life

Sick of always wondering how other people afford to travel so often?

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