Leave Strategies: The Best, Worst, and Weirdest Ways We’ve Seen

Reading Time: 7 minutes

It’s that time of year again when all of us start thinking and planning for the year end holidays (i.e. coming up with various leave strategies so that we can optimise for the long weekends and public holiday weekends). We just can’t waltz off from our work; our livelihood depends on it. 

If we could just waltz off from our work without repercussions, then most of us would probably be enjoying the beaches of Thailand with a drink in hand right now.

Ah, the wonders of freedom.

Alas, it is not as simple as that for us working adults. We have one big issue whenever we plan for the holidays as working adults. 

Thought about it? Yeap. It’s getting our leave approved (money is a close second anyway). It’s a nightmare experience for some, and for others, it’s not too difficult. The crux of the problem lies with information asymmetry, people skills, and timing. 

But hey, look on the bright side, most annual leave requests are based on objective assessments and is a legal right in many countries. Many working adults are sometimes simply not aware of certain things, which results in their leave applications being rejected. We covered that extensively here.

We’ve heard so many stories on how people plan to apply for leave, and we wrote this piece just for you, dear reader! You can take a page out of this post to know what you can emulate, what you shouldn’t emulate, and what you can try if you’re feeling lucky.


The Best

The best ways are the ones that were planned meticulously and executed spectacularly.

Remember the time when you were at High School or University? When the holidays approached, there was always this one person that would plan everything out, and would finish all the assessments before the holidays. (Hey, we could be talking about you, stellar person!) Yeah, that’s basically it, but multiply that idea by five and you’ll get what we mean in this section. 

Here’s a guide on how the best strategies are executed:

  1. These people are the ones that meticulously keep track of their leave count, and will apply at least a month before their self-scheduled leave plans.
  2. They make sure to take advantage of public holidays, structure their break for as long as possible, and they are well aware of their rights as employees.

  3. Additionally, they make the effort to gently remind HR departments about their leave application, and the reasons they put in are well crafted and sound.

  4. A bonus would be that they know about the company’s timeline, and will carry out their applications at the right time. 

On the personal front, they would ensure their teams are well aware of their intended leave dates, and they would schedule meetings with their managers to ensure proper alignment of the company’s timeline. Occasionally, they throw in random lunches with their “friends” at HR in order to win some brownie points for their application (Hey, every bit helps here). 

Of course, your performance throughout the year warrants an award as well. The people that do exceptionally well are given higher priority at work to handle bigger issues, but they also hold leverage on the company for certain benefits like this topic right here. People who make use of this information are more likely to succeed at getting their leave approval.

The lesson here is that in order to have a longer holiday and frankly less stressful one, plan meticulously. Here’s a mini checklist for you to consider the next time you’re going to apply for leave:

  1. Check the number of leave days you have left.

  2. Check the month in which you are leaving and see if it coincides with any public holidays. 

  3. Schedule an informal meeting with your team members and see if compromises can be made (clashes, handover work, etc.)

  4. Prepare your documents for the leave application and do it in advance (at least 1 month before you go on your vacation).

  5. Once approved, schedule a meeting with your manager to be clear on the company’s timeline and whether your temporary departure would affect anything. 
Just like Andy Dufrense, you’ve earned it at this point. Go enjoy.

That’s pretty much it. Master this, and you won’t have to worry about the plans backfiring. It’s just a matter of enjoying your break now with your job taken care of. But don’t stop here, the rest of the article is about to get more interesting. 


The Worst

Seriously, too many people commit these mistakes. Don’t be another statistic.
Photo by Justus Hinz on Unsplash

Honestly, this is actually cringeworthy to read because all these mistakes are avoidable, and we’ve probably done a few of them before. A lot of new entrants into the workforce are often the main suspects when executing their “perfect plan” based on erroneous notions.

The first step in this erroneous strategy is to assume that all employees, regardless of their employment term, gets equal amounts of leave days. Basically, being  unaware of their rights as employees.

This is a big no-no, and results in hilariously epic fails when negotiating for leave. If anything, it just solidifies the idea that you’re too innocent, and some people could take advantage of that. 

The second step is to assume that your leave application would be approved a week before you fly off for you vacation.

That sounds great, except for the fact that it is nearly impossible for you to do that. The reality here is that it just doesn’t make sense for you to suddenly have an “epiphany” for a deserved holiday, jamming in that keyboard for a leave application, and then hoping for the best. 

We’ve seen it before, employees who just go on and on about their planned holidays only for it to fail with a rejection email from HR. That really stings because some people we’ve seen really believe in their strategy till the point of booking all the essentials for their trip which are mostly non-refundable. Don’t repeat this painful lesson, apply in advance! 

This next step isn’t effective immediately, but it affects your future leave applications, so learn it right guys. The third step is not to plan with your team and not to discuss with your manager on timeline issues.

We get it, you want privacy and some time off from work. But this just shows how much you value yourself over others in the office, and that image sticks for a very long time in others.

That can dampen your future prospects, and can definitely sour relations if the work you were doing was just suddenly dumped on someone else on your team. Remember the time someone just vanished when you’re supposed to do it as a team? It feels like that sometimes, and the feeling sucks. 

Finally, the worst one we’ve seen is actually after the rejection email is sent to the inbox of the employee. We’ve seen people flip out and lose their cool over their deserved “break” and some would begin to get confrontational. While it is your right to get a break, there are sometimes very valid reasons as to why you weren’t given one.

It could be because your leave days are used up, you’re on a team project which needs to be delivered, or you’re just not entirely aware of your “full” rights. It could be a myriad of issues, so throwing a tantrum doesn’t help at all. If anything, a tantrum just makes you look immature and could get you the boot if you’re not careful with boundaries. 

The lesson here is simple: Check yourself before you wreck yourself. Just don’t emulate the steps above. 


The Weirdest

Remember the golden rule. 

We’ve heard of the best and worst, but what does it mean to be the weirdest? Well, it isn’t necessarily good nor bad, it just works or it doesn’t. People have tried it, and some have yet to try it, but we’ll let you know what we’ve seen so you can be the judge. 

One of the weirdest ways we’ve seen is applicants guilt tripping their managers and HR persons. They would come up with excruciating brilliant backstories or even settings in order for their plan to be successful.

The intended effect always tips the scale for their leave to be approved. We’ve seen it before, how some people make the grandest of stories, and how they showcase their act is truly an Oscar worthy nomination.

Of course, most of the “epic fail” moments come up if they’re caught conjuring the whole act. Kinda like lying that you were sick, but you went to the beach and posted on Instagram without an afterthought. 

Another one of these weird ways we’ve seen is when the employee applying for leave suddenly acts very friendly and nice towards the managers and HR persons. Sort of like a Littlefinger-estique way towards a leave approval. Jobs are done much faster, they come super early, and are reporting almost everything to the higher ups.

Sometimes, they scheme and inform on other team mates, and then sort of bump their stats higher than everyone else as quickly as possible. Sometimes, HR people might catch on and enjoy the perks of a nice informant. But 100% of the time? They cringe about it with other managers. The choice is yours anyway.


Closing Remarks

If you’ve noticed, the best way to get your leave approved ASAP is to generally be a nice person and do your due diligence. But often times the information you seek is locked away. What if you had a way to manage your leave information with just a click of a button? 

Well you’ve come to the right place. Here at Talenox, we provide exactly that and more. If you’re a company owner or a decision maker, claim your free one month with us now!

This post is written by young and talented guest contributor Calvin Tang, a self-proclaimed optimist nomad.

Like this article? You may be interested in these too:

Why Your Leave Applications are Rejected

Unlimited Leave Policy: Land of the Free, Home of the Idler?

3 reasons integration is crucial for your SME

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