How to Ask for a Last-Minute Vacation (Should You?)

By Joe Issid

As Mick Jagger has so articulately expressed for the last half century, you can’t always get what you want. And for anyone who has held a job for any length of time, this refrain must certainly ring true – at least some of the time. Historically, employees have often bemoaned two major elements of their work lives: they are underpaid and overworked. What is even more surprising is that a larger-than-you-think percentage of employees actually forego their earned vacation annually.

While this may seem insane to you, the fact remains that many Canadians don’t take enough vacation. Now, the reasons behind these behaviours are complex and not easily quantified. But a major hurdle that many employees face is they believe they need to plan their vacations months in advance, which may not be convenient or feasible. And we have often been discouraged from asking for last-minute vacations as it is difficult for our employers to accommodate such requests on short notice. But why have we become reluctant to ask for what is rightfully ours – even if it is at the last minute? Here are some ways to approach this discussion.

Be reasonable

This may sound fairly obvious but you really do need to consider the implications of a last-minute vacation request. If you barrel into your manager’s office and demand to take a month off, you will likely find yourself embroiled in an unpleasant exchange with no easy solution. Also, and this should go without saying, you need to ensure that you are entitled to take this vacation and that you are not violating any company policies. It will surely reflect poorly on you if you are demanding to take a vacation that you have not earned. While you may certainly have a pressing need to take some time off, you need to see the bigger picture and determine a reasonable approach.

Take stock

Are you already behind in your work? Are your projects stable and can they withstand your absence? Before you even approach your boss with this request, you need to make sure you are prepared to answer these questions truthfully. If you believe that your absence will be hugely disruptive, it is likely that your boss will feel the same way. Spend some time and try to measure the true impact of your vacation; you will then be able to have a reasonable and informed conversation with your manager. Take comfort in the fact that any reasonable boss will encourage you to take time away from the office if it does not massively impact important work.

Have a plan

Again, before you even ask to talk to your boss, you should have a reasonably detailed plan in place to accommodate your absence. Failure to do so will suggest that you are saddling your boss with all your work and making him/her responsible for managing your schedule. It also makes it seem as though you are acting on a whim and that you haven’t considered the impact of your actions. This is both unfair and unprofessional. I would suggest you do both yourself and your boss a favour: carefully plan out how you will ensure that your absence causes minimal inconvenience.

Delegate

Many people have a hard time delegating their work and this is often highlighted when staff members take vacation. It is all too common for entire processes to stop entirely when the person responsible has taken time off work. This failure to delegate often evolves into a negative catch-22: you can’t take time off work as you have become too essential to the organization. However, if you were able to train someone else and delegate your work to them temporarily, you’d be able to take more frequent or longer breaks from work. It truly behooves you to make sure those around you are willing and capable to take on some additional responsibilities in your absence.

Offer to do some work

Unless you are going to be swinging from vines in the heart of the Amazon, you will almost certainly have the ability to answer a phone or respond to emails. While this may not seem like something you are thrilled to do, it may be the one thing that will ease your boss’ mind. If you are reachable while you’re away, your boss will feel less anxious about “losing” you for any period of time. Be warned, however, that this offer should contain some specific parameters (such as frequency of responses or specific pockets of availability). If you are not careful, you may inadvertently be taking a working vacation instead.