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Top 5 Tricky Interview Questions: Why Hiring Managers Ask Them And How You Can Respond

Going for a job interview? Prepare yourself for these common (but tricky) questions.

With unemployment at a relatively low rate of 2.2% in Singapore, it appears that most people land jobs eventually, if they went for enough interviews. However, while it might not be that difficult to get a job right now, scoring one that you really want may be significantly tougher.

This is because the jobs that you want are likely to be those that everyone else is also gunning for. Factor in an aggressive automation drive within companies, productivity initiatives by the government and a short-term exodus of companies unable to cope with costs, and it’ll take simple math for you to figure out that more graduates are going to be vying for the same jobs going forward. In fact, this trend is already on the rise with graduate unemployment increasing from 2.9% in 2014 to almost 4.2% today.

To score your dream job, you need to be able differentiate yourself from the pack, especially once you’ve gotten your feet in the door with an interview. Many of you would have probably done research on the toughest interview questions, but this rarely matters as they are unlikely to be repeated. Besides, companies that do repeat these questions will tend not to be the world-beaters you expect to join.

Read Also: Applying For A New Job? Here Are 5 Important Resume Tips To Consider Before Mass Sending Your Resume

Instead, we highlight five evergreen but tricky questions hiring managers frequently ask to stump candidates, coerce them into giving up more information and help them get a sense of how well candidates react to unexpected situations.

#1 What Is Your Current/Last Drawn Salary?

If you’ve ever been to an interview in Singapore, you’ll know this question is coming. The thing is, no matter how many times we’ve been to interviews and had to answer this question, it’s always uncomfortable.

What this question tries to decipher is usually one of two things – 1) to offer you a slight raise but a package lower than the maximum or 2) determine if you’re a person who has the strength to stand up for yourself if you truly do not want to answer the question.

How you can respond:  

You’re not obligated to tell them your salary. If you don’t feel comfortable telling them, politely decline the question. Don’t try to give in by telling them a range or asking if it’s absolutely necessary to tell them.

Even if you’re comfortable with letting them know your current salary, always direct the question away from just money. Spending a long time focusing on your remuneration and benefits will make your potential employers think you’re just going to work for the highest bidder and will move if a higher bid came in.

Instead, you want to talk about the non-financial reasons you want the role – be it working for an international company with a worldwide focus, one that requires travelling (or no travelling) or something else that compelled you to apply.

Another thing you should never do is lie. While it may be tempting to overstate your salary to get a better offer, lying can catch up with you very quickly and all it takes is a phone call to your previous employer.

Read Also: 5 Things To Check Off Before You Quit Your Job Without Having Another Job

#2 What Is Your Biggest Weakness?

This is another question that gets asked over and over. Many job interviewees may think that the best way to answer this question is actually to make your “supposed weakness” sound like a strength – this may not always be the best strategy.

In fact, one job interviewer we spoke to said he uses this question to snuff out the “B******ters”. Hiring managers are not stupid, they know when you’re just trying to make yourself look “meticulous”, “detail-oriented” or a “workaholic”.

How you can respond:  

Just be truthful.

Of course, answering the question truthfully should just be the first part of your response. After explaining a weakness of yours, go on to describe how the weakness affected you in your last role, and what you did to overcome the weakness or improve yourself.

Firstly, this will show your potential employer that you’re not a “B******ter”. They will also know that you’re self-aware and that you will do what it takes to mitigate the problem or correct the situation in a professional way. It also shows that you are always learning and improving.

#3 What Else Can I Tell You About This Role?

This question is trickier than you may think. It usually comes at the end of the interview, when you might think you have already discussed everything there is to talk about regarding the job, so there isn’t much to left to ask. At the same time, you don’t want to just say “I have nothing to ask” – thinking it may reflect badly on you.

What this question seeks to find out is if you are capable of critically assessing your interactions with the hiring manager. You can’t possible prepare for this question as you may have discussed some of the things in the earlier part of the interview, and you also can’t save this question for the end as you may not be asked this question.

How you can respond:  

First up, if you know this interview is just the first phase of the hiring process, never ask about your remuneration or any benefits the company provides. This is probably a question for the later stages of the interview process or be discussed if your interviewer brings it up. Refer to question 1 to answer this.

Use this question to your advantage rather than be thrown off by it. Try to decipher things that aren’t necessarily related to you.

Ask about the last person in the role, what that person was like, the problems that person encountered in the role, and even where that person is moving to if they’ve left the company. This will give you a lot of information about the company culture and your job prospects.

You could also ask about the person you’ll be reporting to, what the person is like, and what the person’s experiences or qualifications are. This will give you a good sense of what the company is looking for when it comes to promotions for managerial level position or what the company prioritises.

You should stick to questions outside the main job description as you should have already been conversing about the role you’re applying for beforehand.

#4 What Do You Do On Weekends (In Your Free Time)

Hiring managers don’t usually want to become close friends and start hanging out with candidates in their free time. There’s more to this question than just getting to know what you like to do when you have spare time.

This question is trying to eke out information on the kind of person you are and whether your character will be a good fit for the company.

Also Read: 5 Useful Electives You Should Take In University

How you can respond:  

Saying you work on weekends is unlikely to score you brownie points. In fact, you could even be seen to be unproductive to have to constantly do work over the weekends.

You can be truthful with your likes and dislikes here. Try to bring out a hobby or an activity that shows a character trait of yours. Of course, make it a positive character trait. So if you like playing underground poker at a HDB flat, getting smashed at Club Street or just lazing around at home all weekend, don’t mention these.

Doing things like playing group sports shows you are a team player and disciplined, as well as physically fit to a certain degree. If you volunteer your time for a worthy cause, you’ll be showing the softer side of yourself, and that you’re a patient and caring person.

You could also bring out other skills that you have, such as sports or educational coaching and even running a blog or work on art. Try to think about how these activities might affect your role if you’re expected to work on weekends or any conflicting roles you may be playing.

#5 Where Do You See Yourself In 5 Years

This question is so cliché that most people don’t even think hiring managers ask it anymore. However, this is a good question for them to ask and they may do so in more subtle ways.

What this question, or less common variations of this question, tries to do is decipher if you’re someone who has passion in the industry and has a vision for yourself. Eventually leaving a company to work for a competitor, while not appreciated, is not unexpected if a good package is offered, but companies don’t like to hire workers who aren’t sure if they’re even going to be in the industry in the long-term.

This is because, you will not likely succeed by putting in half-hearted efforts and there isn’t much incentive for the company to try and retain you if you’re just not interested in the industry.

How you can respond:  

Firstly, instead of thinking about how to respond, you should understand if you’re really in the right industry. If you don’t think you are, then try not to get found out as a “B******ter”.

If you are, then what you want to focus on is what you want to achieve in the next five years in terms of skills, knowledge, projects and the kinds of experience you want to have. Talk less about where you actually see yourself within the company and focus on where you see yourself as a person.

Go In Prepared And Don’t Freeze

There’s no real trick to acing an interview. You just want to go in prepared, know the company, know what kind of skills they’re expecting you to have and know how you’ll answer some of the questions they have.

Read Also: 8 Essential Skills You Need To Survive In Today’s Job Market (That You Weren’t Taught In School)

Your hiring manager has a role to fill at the end of the day, and your résumé has already gotten you through the door. You need to play up your strengths and be truthful about your weakness. Your character also plays an important role in giving you an edge over other potential candidates so be yourself.

Hopefully these five questions will give you a better idea on how you can tackle tricky questions in general. If you’ve stumbled or given up more information than you wanted, don’t freeze. For example if you’ve given up your salary figure when you didn’t want to, you can say that part of the reason you’re leaving is because you’ve outgrown your role or want something more challenging – this is an indication that you think you deserve more. aims to provide interesting, bite-sized and relevant financial articles.

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