When should you inform your boss that you are going on leave???

With my increasing urge to travel all year round, I have found myself always  pondering over the question – What is the right time to inform your boss that you plan to go on leave?

In an ideal world, the process would be fairly simple – drop in a leave application to the boss and viola its done. But unfortunately this world is not ideal and the leave application process does not work this way. In my case even with the latest technological systems (that provide for less human interface and more automated mechanisms) i.e. you can just send an auto request to the million bytes of codes and they auto approve the request – has not worked. 😦

So I am left with the age-old way conventional way of approaching my boss and have the most uncomfortable conversation to get my much deserved paid leave approved. My all such conversations are on these lines – “Sir, I want leave? No, there is no emergency but I want to travel? I know it’s yet again, but I have leaves that I have to use? Sure, you can think about it? Between when did you say I can follow-up with you on this again?’

This has directed me again to the question – So what is the right time to tell the boss? Is it be months in advance when the likes of me book their long distance travel tickets? Or, should it be 2 weeks in advance when you are kind of sure what your work schedule looks like for the next couple of weeks? Or, should you just disappear one fine day and come back to put in your leave, as the deed’s done anyways so he / she might as well approve? I also found myself looking for answers in the cartoon strip below, just replace the word “advisor” with “boss”.

Pic courtesy – http://www.phdcomics.com

While the question is still hanging over my head and some part of my brain is trying to solve it – I have tried to devise a scientific process to go about asking for leave. Please note – that this may work for the vast majority, but it does need customisation based on your work profile, nature of the boss and your company policy and processes. So my way is –

1. Leave Timings – As a practice always avoid going on leave when mass office staff is on leave like the major holidays e.g Diwali, Christmas, etc. This always creates a general impression about you that you are a savior / dependable person and work when others do not. This also works to your advantage – it helps you avoid paying the inflated costs in all tourist places and being unable to see most things anyway due to massive crowds. Additionally, avoid going on leave around important meetings, client deadlines, etc. No one appreciates taking on any additional work load when they are anyways over loaded with their own.
2. Be observant – 10 days before you decide to approach the boss with the request, start paying special attention to his / her moods and general happenings in life. If there are no major problems and he is ok, then your life gets easier but if it’s the other way around, then give a break for 10 – 15 days for those problems / issues to sort out and then re-start the process.   But please be sure to lay low when he is bogged down with other things as you do not want to be on his / her wrong side when they are anyways upset.
3. Burn the midnight oil – During this observation phase (when the boss is carefree with no major issues), log in a few extra hours of work everyday and be at the very best behaviour. This somehow always works and gives an impression that you now genuinely deserve a vacation.
4. Points to prepare – Before approaching the boss, be prepared for the following questions – do you have a back-up? who will work on this in your absence? is there anything due to the client during that time-frame? Have you completed the following tasks? You life will be much easier and chances of success much higher if you have satisfactory answers to these questions prepared in advance.
5. Approaching the Boss – Once you have ascertained that boss’s life is ok and you are in the good books, then decide on a day and keep track on when the boss seems particularly happy. The moment you see this opening, immediately charge in as this moment is too precious to be wasted or lost. In a normal voice start the conversation with a few good things that you have completed / done before the due dates or completed something that he / she wanted and when he / she is even happier with you then put in the question in a very casual way.In normal cases, this should work 90% of the times. In case it does not, then start the process all over again in a few weeks. But this time be sure to be prepared for what went wrong the last time. AFTER ALL PRACTICE MAKES ONE PERFECT.

LOL Disclaimer – This post has been written by the author with a humorous intent and does not necessarily guarantee success. Please follow this process at your own risk and the author is not responsible for any rejections of leaves or any kind of losses thereafter. And most importantly all bosses, including my own, please excuse 🙂