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The Most Challenging Interview Questions and Answers You Should Give

The Most Challenging Interview Questions and Answers You Should Give

As Product Manager for Lifehack I’m often required to interview people. However, let me be honest with you – I don’t really like interviews. Having said that, there’s a part of interviews that I’ve actually grown to enjoy…

It’s the part that most candidates probably hate. Namely, the interview questions that move beyond the common and go into the realm of challenging or ridiculously tricky.

Some candidates answer these questions with cliched replies, others with weird replies, and still others rise to the occasion and answer with creative, intelligent and witty responses.

It’s the challenging questions that can set you apart from the competition

One thing I’ve learned after conducting numerous interviews, is that the challenging questions rapidly separate the weak from the strong candidates.

To give you an example of this, I remember asking two candidates the following question: “Can you describe yourself in three words?”

The first candidate looked horrified, before stumbling the words: “Confident… skilled… experienced.” Not the worst answer, but not the best either! Here’s what the second candidate did. She listened to my question, paused for a second, and then simply said: “Yes I can!”

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Given that we were hiring for a creative role, it’s no wonder that I much preferred the second candidate’s response. It was delivered with flair, and was an inventive (even funny) reply to a deliberately awkward question. The first candidate offered nothing more than a cliched, dull response.

What the responses immediately told me, was that the first candidate probably struggles under pressure – while the second candidate would be likely to thrive under pressure.

Clearly, a strategic, mature and imaginative reply quickly sets a strong candidate apart from a weak one.

Don’t answer with the information that the interviewer expects

The essence of answering difficult questions is never answer with the information that the interviewer expects, but instead, provide an answer that includes information you’d like them to know. It’s a subtle difference, but will keep you in control of the interview. (And will show your most favorable characteristics to the interviewer.)

In other words, you’ll be proactive instead of reactive.

To be a skilful interviewee, you’ll need to know how to easily and quickly switch the focus of an interview, so that your positive side is always on show. As you’ll see in a moment, there are several techniques that you can use to achieve this.

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It would be impossible to cover all the challenging questions that you may be asked. However, by looking at a selection of difficult questions, you’ll be able to spot the necessary tips and tricks for answering almost anything you’re likely to be asked.

“You don’t appear to have sufficient experience?”

When people talk about experience, they often mean ‘years’ of experience.

For example, a person with 10 years of experience at a company did the same things over and over again, while another person with 3 years experience at a company tackled hundreds of issues and even managed to save the company. Who is the more experienced candidate?

The nugget of wisdom to remember here, is that if you get questioned over your lack of ‘years’ of experience, you need to define exactly what your experiences have been. Be sure to highlight what you have done, and talk about the many challenges you’ve overcome.

By doing this, you’ll convince the interviewer that even though you only have 3 years of experience, that you’ve learned more than someone who’s had 5, 7 or even 10 years of experience.

“What’s your salary expectation?”

You should always be prepared for this question, and if given a range to choose from, make sure that you pick a salary that is higher than the median. This will demonstrate your confidence in yourself – and your ability to do the role you’re interviewing for. If no range is given, but the interviewer insists that you state it, choose instead to give a concrete number, not a range. This will persuade the interviewer that you know exactly what you want – and that you’re serious about the role.

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Forget about worrying whether the amount you’ve stated will be too high. If they really want to hire you, they will ask further details about the package you expect. And please don’t panic, as it’s unlikely that your proposal will scare a prospective employer. (Of course, ensure that you’ve done your research and know what the going market rate for the role is.)

If they really can’t match your salary expectations, then this is where some negotiating skills around a benefits package will come in handy. For instance, they may offer to pay for your internet connection at home, your travel costs – or even provide you with a company car. If you’re able to have a serious conversation with the employer about this, you’ll instantly demonstrate that you’re a professional person who’s open and willing to consider different factors.

“Why are you leaving your current company?”

You’re probably aware that it’s not good practice to criticize your previous company. However, I recall interviewing a candidate who cleverly talked about the reasons she wanted to quit her current company, but managed to highlight the achievements that she’d made during her time with them. It’s like walking a tightrope hundreds of meters above a canyon. One slip, and you’ll find yourself plummeting to the ground. One slip in your interview, and you’ll find your chances of getting the job plummeting too!

The candidate above impressed me. Her shrewd use of language persuaded me she was not bitter about her previous company – but instead, she was simply ready for a new opportunity. This is the type of candidate whom most employers are looking for.

A further example for you to think about…Let’s say you currently work in a call centre, and you like your job, but you’re not comfortable with the amount of sales pressure you need to apply to callers. The latter is a genuine reason to want to seek a position at a new company. However, in an interview situation, you don’t want to dwell on the negatives. Instead, you could say something like this: “I’ve enjoyed working at my present company, and have learned lots of things, however, I’m now ready to expand my skills and experience.”

“What you did before doesn’t fit our role very much?”

This may be true, as you might be applying for a role in a different field – or one that has a different scope or target customers, etc. However, instead of focusing on these superficial factors, you must decisively lead the interviewer to focus on the fundamental and common skill sets that your previous job and the new role share. For instance, a job in accounting would be complimentary to a job in business analytics. They both deal with numbers, and require a keen eye for accuracy.

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So, to answer this particular challenging question, explain how what you’ve learned before can actually be applied to the new position. If you can do this well, you’ll even be able to convince the interviewer that your previous experience can help you outperform those who are already working in the field. You can do this by emphasizing how the ‘difference’ can help you bring in new insights and ideas into their company. By doing this, you’ve taken a perceived weakness – and turned it into a legitimate strength.

Imagine for a moment that you currently work as a school teacher, but you’re now keen to change careers and to find work as a writer. In an interview situation, you could highlight how at school you used clear, concise and engaging stories to impart knowledge and wisdom to your students. These are the same skills that you could bring to writing news stories.

“Are you having other interviews, if yes, what are they?”

Always remember, the gist of answering questions isn’t to answer what the person who asks want to know- but what you want them to know.

For sure, you can answer their questions frankly, but be certain to switch the focus when needed. This might be to highlight what you’re looking for in a company. For example, “I’m looking for a company which is passionate about growth, and values open communication…” Statements like this will help persuade the interviewer that you’re a good fit for the role and the company.

As for whether to say you’re having other interviews… My recommendation is to say yes. You don’t need to state what they are, but be admitting that you have other interviews, will give you the aura of someone in demand.

My final piece of advice is: Don’t shy away from challenging interview questions. They are your opportunity to shine, and to show that you are head and shoulders above other candidates.

More by this author

Brian Lee

Chief of Product Management at Lifehack

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Last Updated on July 17, 2019

The Science of Setting Goals (And How It Affects Your Brain)

The Science of Setting Goals (And How It Affects Your Brain)

What happens in our heads when we set goals?

Apparently a lot more than you’d think.

Goal setting isn’t quite so simple as deciding on the things you’d like to accomplish and working towards them.

According to the research of psychologists, neurologists, and other scientists, setting a goal invests ourselves into the target as if we’d already accomplished it. That is, by setting something as a goal, however small or large, however near or far in the future, a part of our brain believes that desired outcome is an essential part of who we are – setting up the conditions that drive us to work towards the goals to fulfill the brain’s self-image.

Apparently, the brain cannot distinguish between things we want and things we have. Neurologically, then, our brains treat the failure to achieve our goal the same way as it treats the loss of a valued possession. And up until the moment, the goal is achieved, we have failed to achieve it, setting up a constant tension that the brain seeks to resolve.

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Ideally, this tension is resolved by driving us towards accomplishment. In many cases, though, the brain simply responds to the loss, causing us to feel fear, anxiety, even anguish, depending on the value of the as-yet-unattained goal.

Love, Loss, Dopamine, and Our Dreams

The brains functions are carried out by a stew of chemicals called neurotransmitters. You’ve probably heard of serotonin, which plays a key role in our emotional life – most of the effective anti-depressant medications on the market are serotonin reuptake inhibitors, meaning they regulate serotonin levels in the brain leading to more stable moods.

Somewhat less well-known is another neurotransmitter, dopamine. Among other things, dopamine acts as a motivator, creating a sensation of pleasure when the brain is stimulated by achievement. Dopamine is also involved in maintaining attention – some forms of ADHD are linked to irregular responses to dopamine.[1]

So dopamine plays a key role in keeping us focused on our goals and motivating us to attain them, rewarding our attention and achievement by elevating our mood. That is, we feel good when we work towards our goals.

Dopamine is related to wanting – to desire. The attainment of the object of our desire releases dopamine into our brains and we feel good. Conversely, the frustration of our desires starves us of dopamine, causing anxiety and fear.

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One of the greatest desires is romantic love – the long-lasting, “till death do us part” kind. It’s no surprise, then, that romantic love is sustained, at least in part, through the constant flow of dopamine released in the presence – real or imagined – of our true love. Loss of romantic love cuts off that supply of dopamine, which is why it feels like you’re dying – your brain responds by triggering all sorts of anxiety-related responses.

Herein lies obsession, as we go to ever-increasing lengths in search of that dopamine reward. Stalking specialists warn against any kind of contact with a stalker, positive or negative, because any response at all triggers that reward mechanism. If you let the phone ring 50 times and finally pick up on the 51st ring to tell your stalker off, your stalker gets his or her reward, and learns that all s/he has to do is wait for the phone to ring 51 times.

Romantic love isn’t the only kind of desire that can create this kind of dopamine addiction, though – as Captain Ahab (from Moby Dick) knew well, any suitably important goal can become an obsession once the mind has established ownership.

The Neurology of Ownership

Ownership turns out to be about a lot more than just legal rights. When we own something, we invest a part of ourselves into it – it becomes an extension of ourselves.

In a famous experiment at Cornell University, researchers gave students school logo coffee mugs, and then offered to trade them chocolate bars for the mugs. Very few were willing to make the trade, no matter how much they professed to like chocolate. Big deal, right? Maybe they just really liked those mugs![2]

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But when they reversed the experiment, handing out chocolate and then offering to trade mugs for the candy, they found that now, few students were all that interested in the mugs. Apparently the key thing about the mugs or the chocolate wasn’t whether students valued whatever they had in their possession, but simply that they had it in their possession.

This phenomenon is called the “endowment effect”. In a nutshell, the endowment effect occurs when we take ownership of an object (or idea, or person); in becoming “ours” it becomes integrated with our sense of identity, making us reluctant to part with it (losing it is seen as a loss, which triggers that dopamine shut-off I discussed above).

Interestingly, researchers have found that the endowment effect doesn’t require actual ownership or even possession to come into play. In fact, it’s enough to have a reasonable expectation of future possession for us to start thinking of something as a part of us – as jilted lovers, gambling losers, and 7-year olds denied a toy at the store have all experienced.

The Upshot for Goal-Setters

So what does all this mean for would-be achievers?

On one hand, it’s a warning against setting unreasonable goals. The bigger the potential for positive growth a goal has, the more anxiety and stress your brain is going to create around it’s non-achievement.

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It also suggests that the common wisdom to limit your goals to a small number of reasonable, attainable objectives is good advice. The more goals you have, the more ends your brain thinks it “owns” and therefore the more grief and fear the absence of those ends is going to cause you.

On a more positive note, the fact that the brain rewards our attentiveness by releasing dopamine means that our brain is working with us to direct us to achievement. Paying attention to your goals feels good, encouraging us to spend more time doing it. This may be why outcome visualization — a favorite technique of self-help gurus involving imagining yourself having completed your objectives — has such a poor track record in clinical studies. It effectively tricks our brain into rewarding us for achieving our goals even though we haven’t done it yet!

But ultimately, our brain wants us to achieve our goals, so that it’s a sense of who we are that can be fulfilled. And that’s pretty good news!

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Featured photo credit: Alexa Williams via unsplash.com

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