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3 Awkward Job Applications You Might Have to Make at Least Once in Your Life

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Joanne Poh

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Job interviews are pretty awkward. You show up all dressed up in that suit you only wear to wedding dinners, ready to impress, and your potential employer knows that if he or she asked you to do a penguin dance in the middle of the room, you would grit your teeth and do it.

It gets worse. Sometimes life throws us a lousy hand, and we end up in situations that are even more awkward than they could already be. Ugh. Like applying for a job and then realising your interviewer is that guy who used to pick on you at school, or, worse, the other way around.

Thanks to the sluggish job market, more people are finding themselves in the rather uncomfortable situation where they need to send in applications to a company they have a history with, or are desperate enough to send multiple applications to the same company. Here’s how to defuse three awkward situations.

 

1. Applying for more than one job at a single company

Okay, we get it, we know you’ve been dying to work at that company, let’s call them Goggle, or Fadbook, all your life.

And now they have several job openings, and you don’t know which to apply for. You’re tempted to apply for both because that might raise your chances of getting hired. That way, if one of the posts goes to another employee, you still have a shot at getting the other.

On the other hand, if you apply for both posts and the company realises what you’ve done, that’s not going to bode well. Employers like to think that a job applicant has applied for a post he’s completely suited for and can specialise in given his past experience. Applying for several jobs paints you as a generalist who can vaguely match several roles but isn’t especially qualified for any of them.

HR experts generally advise that you apply only for one job. The problem you’re facing here is really that you don’t know which of the two jobs you want more.

Rather than trying to hoodwink the company into overlooking the fact that you applied for two posts, focus your energies on figuring out which of the two posts would be better suited to you.

If you really don’t know, you might need to undertake further research on what each of the jobs really entails. Speaking with people who work in similar capacities is often all it takes to make your choice clear.

 

2. Applying for a job at a company that previously rejected you

Okay, we get that you don’t want to look desperate, but should you ever take no for an answer?

Generally, HR experts agree that it’s fine to apply for a job that you were previously rejected from, whether or not you were called up for an interview.

After going through scores of candidates, the company might have realised they couldn’t find anyone suitable and be open to lowering their standards.

In addition, if you give yourself enough time, you might be able to gain some relevant experience that will let you update your CV and make it look more impressive than it was when you first applied.

However, it’s important to give them enough time to come to that conclusion. If you get rejected on Monday and then resend them your resume on Tuesday, you’re going to come off as a psycho. It’s also a good idea to send them an updated resume that’s at least a little better than the one they already received and sent to their recycle bin.

In general, it’s a good idea to wait at least 4 to 6 months before reapplying to a post you were previously rejected for.

 

3. Applying for a job at a company you used to work at

Remember when you quit that crappy job, triumphantly flinging your resignation letter on your boss’s desk? Well, we hope you don’t if you’ve later realised you need to apply for a job at the same company somewhere down the road.

Singapore is a small country, and going back to work for a former employer is more common than you think. Many of my former colleagues and friends rejoined former employers after a few years working elsewhere.

But just because so many people are doing it doesn’t mean you should, too. Before you send in your application, find out if the people you used to work with are still there, especially former bosses and close colleagues. Be aware that some of your previous colleagues or subordinates, if they are still there, might have been promoted to positions that are now on par or superior to yours.

Then you want to take a good, hard look at your relationships with these people. Did you leave the company on a good note? Would they be happy to see you back there? Send in that application only if the answer is yes. Do note that even if your previous bosses or teams have left the company, it’s likely they’ll be called up to give references.

It is usually quite easy to suss out if your former colleagues want you back there. If they have good memories of you, you have a very good chance of being considered for the post, and might even be offered the job right off the bat. However, if the contrary is true, your chances of getting the job will undoubtedly be sabotaged, and you can expect to make a guest appearance in their office gossip for the next day or two.

Have you ever applied for jobs under any of the above circumstances? Share your experiences in the comments!

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Joanne Poh

In my previous life, I was a property lawyer who spent most of my time struggling to get out of bed or stuck in peak hour traffic. These days, as a freelance commercial writer, I work in bed, on the beach, in parks and at cafes, all while being really frugal. I like helping other people save money so they can stop living lives they don't like.