How To Get Your Leave Applications Approved All The Time

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When it comes to applying for leaves, we are almost always uncertain if they will get approved.

So, how do you get your leave applications approved… all the time? Read on and let me share you that one tactic that never fails… ever!

I was chatting with a very senior director at an investment banking firm a few months ago. He had purchased a CV writing service from us and I was his assigned writer. Somehow, the conversation drifted towards emails. Michael (not his real name) had quite a bit of insight as to how to get your leave approved almost all the time.

Our conversation was fascinating. It spanned a whole bunch of management topics. For example, when hiring, Michael always favours candidates with good writing skills. It doesn’t matter what the position is – Investment Analyst or IT Exec – he always favours strong writers. It initially didn’t make sense to me, I’d always hire the most qualified individual.

Michael’s reasoning was this: “Writing is making a comeback. With email and smartphones, almost all our communication is done via writing. I need good writers around me who can express ideas with great clarity. Everyone should learn how to write well. It reflects clear thinking.

The man had a point. 30 years ago, almost all communication was done face to face in the office or via the phone. Back then, you needed strong verbal communicators. Today though, the high performing office requires strong communicators in the writing form.

Our phone conversation then drifted toward how to send your boss an email. Bosses are really busy people. They’re making dozens of decisions a day. As a subordinate, our job is to help make that decision making process easier.

For example, instead of sending an emergency email like this:

Email Title: Server Down

Dear Boss,

The office server died today. Should I call a vendor to fix it?

Instead, a better email would be:

Email Title: URGENT: Server Down

Dear Boss,

The office server died today. Fortunately, I’ve restored all functions on our backup server. Office operations will not be affected. All our trade logs are working correctly.

I’ve attempted to but have been unable to diagnose the original failure. In the meantime, I will be monitoring the backup server performance closely to ensure it stays up and running.

We will need to rectify the failed server. I’ve contacted our usual IT vendor over the phone, the repair can be done by them. Price should be between 8000 – 12000 SGD. They can come down by tomorrow. Repairs will take less than 1 day.

As this expense is above 5000 SGD, I need your approval. Can I please proceed to hire our vendor for the on-site repairs?

Obviously the second email far better. Let’s understand why

The first paragraph immediately states that the backup is running and that operations are back to normal. A boss is most concerned about business functions continuing as per normal. How that is accomplished is often secondary. Your job is always to put him at ease about the situation.

The second paragraph shows you’ve put in effort to resolve this yourself. That way he doesn’t need to email back saying “Have you tried to fix it?” – You’ve anticipated his request and seen to it.

The third paragraph is also excellent because it:

  1. Confirms repair is doable
  2. Gives indicative price
  3. Estimates timeline for repair

For a boss reading this email, he can easily reply with one just line: “Ok, please proceed”

In the first email though, the boss would need to send a list of questions, putting strain on his already hectic day. Remember, the goal is to take as much burden off as possible from your boss. Make it easy for him or her to work with you. Make it easy for your boss to say “OK!”

So, how can this be applied for taking leave?

Most people send a leave application email like this:

Dear Boss,

Can I take leave this Friday? (25th March) I’m heading overseas with my family.

Now compare that, to this email:

Hi Boss,

I would like to request for holiday leave on Friday 25th March because I will be overseas on a family vacation.

When I’m not in Singapore, I can be contacted via email and WhatsApp

Here’s a summary of my unclosed projects:

1.Proposal for Client XYZ

I’ve finished the proposal and gotten approval from 3 project managers. The proposal has been proofread and will be sent today. Josephine has instructions to follow up with the client on this.

2.Analysis on Product ABC

Joe and I have completed the preliminary analysis and have sent it to the client. Joe will record the client’s feedback and we’ll begin working on the next version after I’m back. The client has approved the timeline for the second draft.

Besides the above, I have no other outstanding projects. Just in case, I’ll be forwarding all my email messages to Joe & Josephine to deal with any emergencies.

Also, if there’s a need to clear urgent projects, I’ll work overtime from the next Monday onwards after I come back from my vacation.

Is this arrangement okay?

Place yourself in your bosses’ shoes, which leave request is easier to approve?
More importantly, in the long run, which employee would you rather promote?

Writing great emails is a skill learned over many years of trial and error. Invest in it. Double down on your efforts to improve your written communication. As Michael said, writing is making a comeback.

I love my job as it allows me opportunities to speak to very brilliant people, such as Michael. It’s very clear to me why he’s in such a senior position – he writes great emails!

I’m going to be using his advice for leave application a lot – starting with the long weekend this Friday. Wish me luck!

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