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How to ask your boss for time off without it being awkward AF

girl looking over sea

There are few things more exciting than finally deciding you’re gonna take time off and go on a vacation.

Your procrastination gets pushed to the side, you embrace that #NOREGRETS mentality and decide to finally treat yo’self. But that vacation mindset often gets quickly sideswiped by the fact that you have adult responsibilities to deal with, and the main one being your job and how you’re going to break it to your boss that you’re putting your out-of-office on for a while.

For some of us, talking to our bosses is something we avoid on a good day, so the thought of breaking the vacation news is enough to make us second guess our trip altogether. If you’re wondering how or when to let them know, or you’re dreading the entire conversation, here are some tips on how to ask for time off without getting on your boss’ bad side:

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Realize that they won’t necessarily be excited for you

Yes, most of us have vacation days that we’re entitled to, legally. We are supposed to take time off, and your boss knows that too, but almost always it’s an inconvenience for them and your department.

No one wants to be a man down for a couple of weeks and have to make adjustments or increase their workload, so if you go into the conversation without acting entitled and bratty, your boss’ bad mood should be a bit better when you break the news.

Plan ahead, as far ahead as possible

Just like most big news in life, giving people as much notice as you can is usually the respectful and professional thing to do. That way, your team has more time to plan accordingly for your departure and your boss will feel less caught off guard when you decide you need to leave the country.

Giving a lot of notice also helps to avoid scheduling conflicts with other people’s vacations, and makes things like upcoming deadlines and projects less of a panic and more something to plan accordingly for.

Create an action plan for who will be covering your workload

This doesn’t apply to all of us but for some, there isn’t really a person who can automatically pick up for us when we leave our duties behind. Having a plan in place for who can help out with your workload, or planning to make up for missed work before or after your time off is a great way to show your boss that your vacation isn’t cause for panic and won’t be such a burden after all.


Talk to them in the planning phase, not when it’s booked

No boss wants to be ‘told’ that you’re taking time off – although you’re entitled to take it, they are also entitled to approve or reject the specific time period if necessary. Make your boss feel as though you’re being considerate and fill them in before you book, just in case they have an issue with it.

Come to the table with multiple dates and options

Being a bit flexible is a great way to guarantee that you don’t overly piss off your boss. Come to the conversation with multiple possible dates in mind, and with the mindset that your trip length is also up for debate. That way, your boss is less likely to say no altogether and more likely to work with you to make your time off work for everyone.

Two digital nomads working at a table with laptops and cell phones.

Pick the appropriate time

Some days are just not a good day to ask for time off (like when you’ve messed something up, sales are down etc.) and some moments aren’t the right moment (like when your boss has back to back meetings and isn’t in the greatest mood). Book a meeting time, find them when they’re in a good mood, pick a slower part of the day – do what you have to do to find the appropriate moment.


Acknowledge if you’re asking for a lot

Ignorance isn’t always bliss, and the theory of asking for forgiveness and not permission doesn’t always work in the workplace. If you’re asking to take time off during busy season, asking for more time than you’re technically entitled to, giving late notice or doing anything else that your boss might not be happy about, being gracious and thankful is the better route than pleading ignorance and seeming inconsiderate.

Remind them if needed

Your boss may not have the best memory so clear communication will help ensure your time off runs smoothly. If you have a lot of vacation days to take and the deadline is fast approaching, reminding your boss of this is a good way to steer them towards approval (they don’t want to get in trouble from HR either).

Prior to your vacation, ensure your boss remembers you’re going away before you’re clocking out on the last day. Having it in writing or clocking it in the system is a great way to protect yourself as well. And make sure your co-workers know when you’re going away, when you’re coming back, and what is required of them when you’re gone.

Be honest

If you need a vacation, tell them. No one wants you to get burnt out so if some time off is what you need to keep your mental health in check, then your boss should know and take that into consideration. We all need a break, and if you go into the conversation with the mindset of coming back refreshed and reinvigorated, it’ll be hard for your boss to refuse.

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Just do it

At the end of the day, being transparent, respectful and professional will make it easier to guarantee that you get that yes. If you’re entitled to time off, take it, and don’t let a little awkward conversation with your boss keep you from an epic vacation. It’s all a part of growing up and getting more comfortable having these tricky conversations with your boss will only make your workplace a better place to be.