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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 March 31, 2020

How To Break the Procrastination Cycle

How To Break the Procrastination Cycle

How often do you find yourself procrastinating? Do you wish you could procrastinate less? We all know how debilitating procrastination can make us feel, and it seems to be a challenge we all share. Procrastination is one of the biggest hindrances to moving forward and doing the things that we want to in life.

There are many reasons why you might be procrastinating, and sometimes, it is really difficult to pinpoint why. You might be procrastinating because of something related to the past, present, or future (they are all intertwined), or it could be as simple as biological factors. Whatever the reason, most of us follow a cycle when we procrastinate, from the moment we decide to do something to actually getting it done, or in this case, not getting it done.

The Vicious Procrastination Cycle

For some reason, it helps to understand that we all go through the same thing, even though we often feel like the only person in the world who struggles with this. Do you resonate with the cycle below?

1. Feeling Eager and Energized

This is when you commit to taking a new action or getting something done. You are feeling confident and optimistic that, this time round, you will do it!

2. Apprehension Starts to Come Up

The beginning stages of optimism are starting to fade. There is still time, but you haven’t done anything yet, and you start to feel uneasy. You realize that you actually have to do something to get it done, and that good intentions are not enough.

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3. Still No Action

More time has passed. You still haven’t taken any action and probably have a lot of excuses why. You start to panic a little and wish you had started sooner. Your panic starts to turn into frustration and perhaps even irritability.

4. Flicker of Hope Left

You can still make it; there is a little time left and you ponder how you are going to get it done. The rush you get from leaving your task until the last minute gives you a flicker of hope. There is still time; you can do this!

5. Fading Quickly

Your hope starts to quickly fade as you try desperately to understand why you just can’t do this. You may feel desperate and have thoughts like, “What is wrong with me?” and “Why do I ALWAYS do this?” You feel discouraged, or perhaps angry and resentful at yourself.

6. Vow to Yourself

Once the feeling of anger or disappointment disappears, you most likely swear to yourself that this will never happen again; that this was the last time and next time will be different.

Does this sound like you? Is the next time different? I understand the devastating effect that procrastination has on many lives, and for some, it is a really serious problem. You also have, on the other hand, those who procrastinate but it doesn’t affect them in any way. You know whether it is affecting you or not and whether it undermines your results.

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How to Break the Procrastination Cycle

Unless you break the cycle, you will keep reinforcing it!

To break the cycle, you need to change the sequence of events. Here is my suggestion on how you can effectively break the vicious cycle you are in!

1. Feeling Eager and Energized

This is when you commit to taking a new action or getting something done. You are feeling confident and optimistic that, this time round, you will do it! The first stage is always the same.

2. Plan

Thinking alone will not help; you need to plan your actions. I always put my deadlines one or two days in advance because you know Murphy’s Law! Take into consideration everything that you need to do, how long it will take you, and what you will need to get it done, then plan the individual steps.

3. Resistance

Just because you planned doesn’t mean that this time is guaranteed to be different. You will most likely still feel the resistance so expect this. This stage is key to identifying why you are procrastinating, so when you feel the resistance, try to identify it immediately.

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What is causing you to hesitate in this moment? What do you feel?  Write them down if it helps.

4. Confront Those Feelings

Once you have identified what could possibly be holding you back, for example, fear of failure, lack of motivation, etc. You need to work on lessening the resistance.

Ask yourself, “What do I need to do to move forward? What would make it easier?” If you find that you fear something, overcoming that fear is not something that will happen overnight — keep this in mind.

5. Put Results Before Comfort

You need to keep moving forward and put results before comfort. Take action, even if it is only for 10 minutes. The key is to break the cycle and not reinforce it. You have more control that you think.

6. Repeat

Repeat steps 3-5 until you achieve what you first set out to do.

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Final Thoughts

Change doesn’t happen overnight, and if you have some deeper underlying reasons why you procrastinate, it may take longer to finally break the cycle.

If procrastination is holding you back in life, it is better to deal with it now than to deal with the negative consequences later on. It is not a question of comfort anymore; it is a question of results. What is more important to you?

Learn more about how to stop procrastinating here: What Is Procrastination and How to Stop It (The Complete Guide)

Featured photo credit: Luke Chesser via unsplash.com

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