How to ask your boss for holidays

Planning a holiday can be almost as fun as the trip itself. But, there’s one element that often puts a dampener on things… asking your boss for time off.

Even the friendliest line manager can switch at the sight of another peak time leave request so you should consider the best line of attack as the best approach is key to making your holiday happen.

While we sadly can’t guarantee a 100% success rate, our guide to how to ask your boss for leave should give you some ideas as to how to secure that all important time off.

Pick a good day

Choosing a day when your boss is in the right frame of mind can be crucial to your success. Avoid asking for leave at time when you know they have pressing deadlines or back-to-back meetings. If possible, wait until you’re riding a wave of workplace success.

Try to find a time to put in your initial request face to face, or if that’s not an option and you are limited to email or a form, make sure you are respectful and considerate in your request.

Get in there first

It’s important to remember that just because you have leave owing, that doesn’t mean you can take it whenever you want.

Securing time off during peak periods, such as the school holidays, is all about planning ahead.

But even if you are travelling off peak it’s sensible to get in first and request leave before any of your colleagues. With most workplaces unable to allow all of their staff to be off at the same time, being the first to request a certain day should make you significantly more likely to get a ‘yes’.

If you’re looking at a last minute break, be sure to get your form in before you book. The only thing than a last minute holiday request is the threat of a last minute holiday that has already been paid for. Remember, this should be a request, not a demand.

Have a plan

If you can, book time off that doesn’t have a negative impact on any big projects or deadlines you may have. Even if there’s someone else who may be able to pick up your workload in theory, try to think of the effect that may have on the wider team.

Consider in advance what you’ll say to your boss if they push back on your holiday request. Being able to present a clear idea of how you will ensure you work is completed and who will cover your absence can be a good place to start. Follow up with an email detailing exactly how you think things will work to show it’s something you have put some thought into.

If you need fixed days off during a busy period (for an occasion such as a family wedding) give extra thought as to how you can minimise distribution.

Prepare to negotiate

If you know you are asking for a popular day off, think about other busy times you might be able to provide cover for the wider team.

For example: if you don’t want to work Christmas Eve, offer to work New Year or be prepared to offer to work a weekend.

If your boss simply can’t sign you off for the full quota of days you need, see if you could work from home or remotely for some of the period - potentially allowing you to still go ahead with your plans (albeit with your laptop in tow).

Point out the benefits of group leave

While the school summer holidays and Christmas can be popular times to ask for days off, they are also periods where things slow down in certain industries.

If you’ve left that festive leave request a little late, point out that with all of your colleagues and business contacts at home drinking eggnog and listening to Christmas music, you won’t have much to do in the office anyway.

Accept defeat

Thanks to limited staff resources, pressing projects and pre-existing leave requests from other colleagues - sometimes whatever you do or say, you’re still heading for a ‘no’.

By limiting your reaction and not going overboard, you’ll show your boss you respect their decision. Hopefully, this will put you in a better position next time you have a request.

If you must weep for your never-to-be beach break, best to do it discreetly in the loos…