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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 January 13, 2020

50 Motivational Quotes for Work to Inspire Success

50 Motivational Quotes for Work to Inspire Success

Let’s face it – no matter how excited you are about a new project or priority in your life, there will always be days when your motivation lags. Days when – despite all the progress you’ve made in the past – it just sounds easier to sit on the couch playing video games than to buckle down and crank out the work needed to meet your goals.

In order to be successful, you must be able to motivate yourself past these humps. Whenever you feel your drive and determination lagging, turn to these motivational quotes for work to provide the extra spark of passion needed to keep you on track.

Quotes about Goal Setting

Whether you’re still in the planning phases of your business or whether you’re plotting a plan of attack to bring about your long-range vision, setting good goals is a critical part of succeeding in business.

Check out these quotes for extra inspiration on how to turn your dreams into reality:

quote-Benjamin-E.-Mays-the-tragedy-in-life-doesnt-lie-in-106113

    “The tragedy in life doesn’t lie in not reaching your goal. The tragedy lies in having no goal to reach.”– Benjamin Mays


    “By recording your dreams and goals on paper, you set in motion the process of becoming the person you most want to be. Put your future in good hands — your own.”–Mark Victor Hansen


    “Give yourself an even greater challenge than the one you are trying to master and you will develop the powers necessary to overcome the original difficulty.”–William J. Bennett – The Book of Virtues


    “The entrepreneur is essentially a visualizer and actualizer… He can visualize something, and when he visualizes it he sees exactly how to make it happen.”–Robert L. Schwartz

    Quotes about Achieving Excellence in Work

    Once you’ve got your goals together, you’ll need to put in 110% of your effort in order to transform these visions into reality. To increase your motivation to work at a consistently high level, take a look at the following words of wisdom:

    “Excellence is an art won by training and habituation. We do not act rightly because we have virtue or excellence, but we rather have those because we have acted rightly. We are what we repeatedly do. Excellence, then, is not an act but a habit.”–Aristotle


    “If you are going to achieve excellence in big things, you develop the habit in little matters. Excellence is not an exception, it is a prevailing attitude.”–Charles R. Swindoll

    Desire is the key to motivation

      “Desire is the key to motivation, but it’s determination and commitment to an unrelenting pursuit of your goal — a commitment to excellence — that will enable you to attain the success you seek.”–Mario Andretti


      “The secret of joy in work is contained in one word – excellence. To know how to do something well is to enjoy it.”–Pearl Buck


      “The quality of a person’s life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.”–Vince Lombardi

      Quotes about Determination and Persistence

      Since every business or other endeavor is bound to hit some rough patches, it’s often a person’s level of determination and patience that brings about either success or failure. These positive quotes give you an extra boost of encouragement:

      “Enter every activity without giving mental recognition to the possibility of defeat. Concentrate on your strengths, instead of your weaknesses… on your powers, instead of your problems.”–Paul J. Meyer


      “Knowing trees, I understand the meaning of patience. Knowing grass, I can appreciate persistence.”–Hal Borland


      “Nothing in the world can take the place of Persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan ‘Press On’ has solved and always will solve the problems of the human race.”–Calvin Coolidge

      quote-Thomas-Fuller-an-invincible-determination-can-accomplish-almost-anything-92190

        “An invincible determination can accomplish almost anything and in this lies the great distinction between great men and little men.”–Thomas Fuller

        Quotes about Leadership

        Whether you use it to engage your employees, to encourage teamwork or motivate others to follow your unique way of thinking, leadership is crucial. Take your leadership cues from these renowned leaders’ famous sayings:

        “The most dangerous leadership myth is that leaders are born — that there is a genetic factor to leadership. This myth asserts that people simply either have certain charismatic qualities or not. That’s nonsense; in fact, the opposite is true. Leaders are made rather than born.” –Warren G. Bennis


        “All of the great leaders have had one characteristic in common: it was the willingness to confront unequivocally the major anxiety of their people in their time. This, and not much else, is the essence of leadership.”–John Kenneth Galbraith

        Leadership is not magnetic personality

          “Leadership is not magnetic personality — that can just as well be a glib tongue. It is not ‘making friends and influencing people’ — that is flattery. Leadership is lifting a person’s vision to high sights, the raising of a person’s performance to a higher standard, the building of a personality beyond its normal limitations.”–Peter F. Drucker


          “The task of leadership is not to put greatness into people, but to elicit it, for the greatness is there already.”–John Buchan


          “High sentiments always win in the end. The leaders who offer blood, toil, tears and sweat always get more out of their followers than those who offer safety and a good time. When it comes to the pinch, human beings are heroic.”–George Orwell

          Quotes for Success

          Think of success as a holistic process – one which results from the combination of goal-setting, excellence, patience, determination and leadership you prioritize throughout your career. These highly successful people provide you with an excellent source of motivation:

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          “Be patient with yourself. Self-growth is tender; it’s holy ground. There’s no greater investment.”–Stephen Covey


          “Believe in yourself! Have faith in your abilities! Without a humble but reasonable confidence in your own powers you cannot be successful or happy.”–Norman Vincent Peale

          Success is the ability to go from one failure to another with no loss of enthusiasm.

            “Success consists of going from failure to failure without loss of enthusiasm.”–Winston Churchill


            “Successful and unsuccessful people do not vary greatly in their abilities. They vary in their desires to reach their potential.”–John Maxwell


            “Would you like me to give you a formula for success? It’s quite simple, really. Double your rate of failure. You are thinking of failure as the enemy of success. But it isn’t at all. You can be discouraged by failure or you can learn from it, So go ahead and make mistakes. Make all you can. Because remember that’s where you will find success.”– Thomas J. Watson


            “The great successful men of the world have used their imagination.  They think ahead and create their mental picture in all its details, filling in here, adding a little there, altering this a bit and that a bit, but steadily building – steadily building.”–Robert Collier


            “It is a paradoxical but profoundly true and important principle of life that the most likely way to reach a goal is to be aiming not at that goal itself but at some more ambitious goal beyond it.”–Arnold Toynbee

            Sports Quotes for Athletes

            You don’t need to be a Michael Jordan-caliber athlete to draw inspiration from the following quotes. Even if you’re just a recreational player or someone who’s using sports as a means to get back in shape after long periods of inactivity, the following motivational sports quotes will encourage you:

            “My attitude is that if you push me towards something that you think is a weakness, then I will turn that perceived weakness into a strength.”–Michael Jordan


            “Pain is temporary. It may last a minute, or an hour, or a day, or a year, but eventually it will subside and something else will take its place. If I quit, however, it lasts forever.”–Lance Armstrong

            Strength does not come from winning. Your struggles develop your strengths.

              “Strength does not come from winning. Your struggles develop your strengths. When you go through hardships and decide not to surrender, that is strength.”–Arnold Schwarzenegger


              “I know what I have to do, and I’m going to do whatever it takes. If I do it, I’ll come out a winner, and it doesn’t matter what anyone else does.”–Florence Griffith Joyner


              “Every time you stay out late; every time you sleep in; every time you miss a workout; every time you don’t give 100% – You make it that much easier for me to beat you.”–Unknown


              “If you are hurt, whether in mind or body, don’t nurse your bruises. Get up and light-heartedly, courageously, good temperedly get ready for the next encounter. This is the only way to take life – this is also ‘playing’ the game!”–Emily Post


              “We must train from the inside out. Using our strengths to attack and nullify any weaknesses. It’s not about denying a weakness may exist but about denying its right to persist.”–Vince McConnell

              Quotes to Motivate Learning

              Committing yourself to pursuing knowledge in a single area is a tremendous endeavor – one that often seems overwhelming given the depth and breadth of information that’s available today. Keep the following motivational quotes in mind if you’re learning:

              “How far you go in life depends on your being tender with the young, compassionate with the aged, sympathetic with the striving and tolerant of the weak and the strong. Because someday in life you will have been all of these.”–George Washington Carver

              quote-William-Arthur-Ward-if-you-can-imagine-it-you-can-36189

                “If you can imagine it, you can achieve it; if you can dream it, you can become it.”–William Arthur Ward


                “It is the mark of an educated mind to be able to entertain a thought without accepting it.”– Aristotle


                “Success is not the key to happiness.Happiness is the key to success.If you love what you are doing, you will be successful.”–Albert Schweitzer


                “Wear your learning, like your watch, in a private pocket: and do not pull it out and strike it, merely to show that you have one.”–Philip Stanhope, 4th Earl of Chesterfield


                “He who asks is a fool for five minutes, but he who does not ask remains a fool forever.”–Chinese Proverb


                “Study while others are sleeping; work while others are loafing; prepare while others are playing; and dream while others are wishing.”–William Arthur Ward


                “Books can be dangerous. The best ones should be labeled ‘This could change your life’.”–Helen Exley


                “A book is like a garden carried in the pocket.”–Chinese Proverb

                All-Time Favorite Positive Quotes

                Finally, whatever your goals are in life, you can’t go wrong by taking the advice of the following famous motivational quotes:

                “Change your thoughts and you change your world.”–Norman Vincent Peale


                “Your time is limited, don’t waste it living someone else’s life. Don’t be trapped by dogma, which is living the result of other people’s thinking. Don’t let the noise of other’s opinion drowned your own inner voice. And most important, have the courage to follow your heart and intuition, they somehow already know what you truly want to become. Everything else is secondary.”–Steve Jobs


                “Nobody can go back and start a new beginning, but anyone can start today and make a new ending.”–Maria Robinson


                “Out of clutter, find Simplicity. From discord, find Harmony. In the middle of difficulty lies Opportunity.”–Albert Einstein


                “Yesterday is not ours to recover, but tomorrow is ours to win or lose.”–Lyndon Johnson

                If we did all the things we are capable of, we would literally astound ourselves.

                  “If we did all the things we are capable of, we would astound ourselves.”–Thomas Edison


                  “You miss 100% of the shots you don’t take.”–Wayne Gretzky


                  “Success is not final, failure is not fatal: it is the courage to continue that counts.”–Winston Churchill


                  “What lies behind us and what lies before us are tiny matters compared to what lies within us.”–Ralph Waldo Emerson

                  Final Thoughts

                  To use these motivational quotes effectively, find the one that speaks to you. Although all of the phrases listed above can be considered “motivational,” only you can decide which one resonates with you most directly.

                  Next, take the quote you’ve settled on and copy it onto small index cards or other pieces of paper that can be stored around your home and workspace.

                  If you’re creative, you can create inspiration boards, signs or other decorative displays featuring your favorite motivational quotes – really, though, the most important thing is that your chosen phrase be accessible in a variety of different places. This will make it easy to access and review whenever you feel your motivation slipping away.

                  More Inspiring Quotes

                  Featured photo credit: Kyle Glenn via unsplash.com

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