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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.

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More by this author

Brian Lee

Chief of Product Management at Lifehack

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Last Updated on July 21, 2021

The Importance of Reminders (And How to Make a Reminder Work)

The Importance of Reminders (And How to Make a Reminder Work)

No matter how well you set up your todo list and calendar, you aren’t going to get things done unless you have a reliable way of reminding yourself to actually do them.

Anyone who’s spent an hour writing up the perfect grocery list only to realize at the store that they forgot to bring the list understands the importance of reminders.

Reminders of some sort or another are what turn a collection of paper goods or web services into what David Allen calls a “trusted system.”[1]

A lot of people resist getting better organized. No matter what kind of chaotic mess, their lives are on a day-to-day basis because they know themselves well enough to know that there’s after all that work they’ll probably forget to take their lists with them when it matters most.

Fortunately, there are ways to make sure we remember to check our lists — and to remember to do the things we need to do, whether they’re on a list or not.

In most cases, we need a lot of pushing at first, for example by making a reminder, but eventually we build up enough momentum that doing what needs doing becomes a habit — not an exception.

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From Creating Reminders to Building Habits

A habit is any act we engage in automatically without thinking about it.

For example, when you brush your teeth, you don’t have to think about every single step from start to finish; once you stagger up to the sink, habit takes over (and, really, habit got you to the sink in the first place) and you find yourself putting toothpaste on your toothbrush, putting the toothbrush in your mouth (and never your ear!), spitting, rinsing, and so on without any conscious effort at all.

This is a good thing because if you’re anything like me, you’re not even capable of conscious thought when you’re brushing your teeth.

The good news is you already have a whole set of productivity habits you’ve built up over the course of your life. The bad news is, a lot of them aren’t very good habits.

That quick game Frogger to “loosen you up” before you get working, that always ends up being 6 hours of Frogger –– that’s a habit. And as you know, habits like that can be hard to break — which is one of the reasons why habits are so important in the first place.

Once you’ve replaced an unproductive habit with a more productive one, the new habit will be just as hard to break as the old one was. Getting there, though, can be a chore!

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The old saw about anything you do for 21 days becoming a habit has been pretty much discredited, but there is a kernel of truth there — anything you do long enough becomes an ingrained behavior, a habit. Some people pick up habits quickly, others over a longer time span, but eventually, the behaviors become automatic.

Building productive habits, then, is a matter of repeating a desired behavior over a long enough period of time that you start doing it without thinking.

But how do you remember to do that? And what about the things that don’t need to be habits — the one-off events, like taking your paycheck stubs to your mortgage banker or making a particular phone call?

The trick to reminding yourself often enough for something to become a habit, or just that one time that you need to do something, is to interrupt yourself in some way in a way that triggers the desired behavior.

The Wonderful Thing About Triggers — Reminders

A trigger is anything that you put “in your way” to remind you to do something. The best triggers are related in some way to the behavior you want to produce.

For instance, if you want to remember to take something to work that you wouldn’t normally take, you might place it in front of the door so you have to pick it up to get out of your house.

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But anything that catches your attention and reminds you to do something can be a trigger. An alarm clock or kitchen timer is a perfect example — when the bell rings, you know to wake up or take the quiche out of the oven. (Hopefully you remember which trigger goes with which behavior!)

If you want to instill a habit, the thing to do is to place a trigger in your path to remind you to do whatever it is you’re trying to make into a habit — and keep it there until you realize that you’ve already done the thing it’s supposed to remind you of.

For instance, a post-it saying “count your calories” placed on the refrigerator door (or maybe on your favorite sugary snack itself)  can help you remember that you’re supposed to be cutting back — until one day you realize that you don’t need to be reminded anymore.

These triggers all require a lot of forethought, though — you have to remember that you need to remember something in the first place.

For a lot of tasks, the best reminder is one that’s completely automated — you set it up and then forget about it, trusting the trigger to pop up when you need it.

How to Make a Reminder Works for You

Computers and ubiquity of mobile Internet-connected devices make it possible to set up automatic triggers for just about anything.

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Desktop software like Outlook will pop up reminders on your desktop screen, and most online services go an extra step and send reminders via email or SMS text message — just the thing to keep you on track. Sandy, for example, just does automatic reminders.

Automated reminders can help you build habits — but it can also help you remember things that are too important to be trusted even to habit. Diabetics who need to take their insulin, HIV patients whose medication must be taken at an exact time in a precise order, phone calls that have to be made exactly on time, and other crucial events require triggers even when the habit is already in place.

My advice is to set reminders for just about everything — have them sent to your mobile phone in some way (either through a built-in calendar or an online service that sends updates) so you never have to think about it — and never have to worry about forgetting.

Your weekly review is a good time to enter new reminders for the coming weeks or months. I simply don’t want to think about what I’m supposed to be doing; I want to be reminded so I can think just about actually doing it.

I tend to use my calendar for reminders, mostly, though I do like Sandy quite a bit.

More on Building Habits

Featured photo credit: Unsplash via unsplash.com

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Reference

[1] Getting Things Done: Trusted System

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