15 of the trickiest job interview questions – and how to nail them

This is one of the most common job interview questions, and also one of the most challenging. The first part is a slam dunk; the second is a potential landmine unless you are careful. For strengths, keep in mind that every company needs people who can do three things well: 1) earn revenue; 2) save money; and 3) save time. For weaknesses, avoid admitting to character flaws. I prefer a “weakness” to be skill-related and past tense: “I wasn’t astute with PowerPoint when I first started, but I read a great book, practised, and became very proficient. Now I train others in PowerPoint presentations.” Any time you can demonstrate how you overcame a weakness, all the better. Another good “weakness” example is to give general answers in which you can plug perceived strengths: “I am passionate about my work and always give each task my all. So sometimes when I see others loafing, I can get frustrated.”

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Another landmine you cannot step on. This is another way of asking for weaknesses. As you begin to feel more and more comfortable with the interviewer, there is a tendency to let your guard down. Don’t. The answer is: “Aside from the occasional nightmare about interviewing, I work so hard that I rarely have a difficult time sleeping. I believe in proper time management and recharging my batteries with sound sleep. I’m no good to anyone if I’m tired.”

A good question particularly if he or she is looking for a promotable candidate. Here you can intersperse more about your personal and business traits. Be very complimentary of the company you work for: “The training was superb” or “I was fortunate to have some great mentors who really helped me.” It will be hard not to ramble a little, but focus on the promotions by title as a result of dedicated hard work and outstanding accomplishments with outright genius. If you haven’t been formally promoted, mention a few new challenges you’ve faced and how you’ve overcome them.

This is a good question to get asked; it is a “buy” signal, implying that he or she is thinking of offering you the job. But it can be tricky: Is he or she concerned that I would leave after a short while? Don’t take the bait. You can put the hot potato back in the interviewer’s lap with an answer such as: “I would hope to have a great career with this company. I respond well to direction and am always looking to learn. I define success as being ready when an opportunity arises. How long do you think I’d be challenged here?”

This is a perfect opportunity to demonstrate that you are a business manager who can identify and solve problems: “I believe in effective strategic planning that involves both forward thinking (in other words, what resources will I need?) and backward thinking (for example, if the deadline is the end of the quarter, what steps need to be made and at what time to achieve a successful outcome?).”

The best way to answer this is to deflect it: “I avoid stress by careful time management. There are only so many hours in a given day, so I try to maximise my time by setting effective goals. On the personal side, I exercise regularly, eat right, and get adequate sleep. I think this helps alleviate stress.”

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Fair question in the interviewer’s mind but unfair to the interviewee. The interviewer cannot expect you to know the intricacies of the position and the company, so you can be general here. After responding with some generalities, I like to send this one back to the interviewer: “I believe in setting my goals in line with the company’s near-term objectives, which I would expect to receive right away. Then I would prioritise my time relative to achieving those goals. What are the company’s most pressing needs right now and do you offer a standard training program?”

This is what I call the “wince” question. The interviewer winces just after asking it, hoping you don’t step on a landmine by blurting out a negative answer. Even if your current company is a torture chamber, don’t tell the interviewer. He or she is actually looking for you to give a positive response. Say, “As you know, I wasn’t looking and am doing well in my current job. I love the training and the culture. Our products and services are superb. My boss is supportive and a great teacher. But my company is being sold, so I’m concerned about my future security. But regardless of my company’s security, both this opportunity and your company seem ideal to me.” If your company is not for sale, you can always say, “The company is small and there isn’t much room for me to grow.” If the reverse is true, say, “I’m looking for a smaller company where I can make a big difference.” Be upbeat about all your experiences and shift gears to show how applicable your training is to the job for which you are interviewing.

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Under the pressure of an interview, many candidates immediately think of the opposite, conjuring up all the things they hate about their current job. There’s also a tendency to dive into minutiae and rattle off meaningless tasks as they pop into your head. Exercise care. Think “big picture” in your answers and intersperse positive character traits. Remember, you want to paint yourself as someone who is a business manager who can run the business. Try, “My ability to manage my time wisely. First, I set daily goals, prioritising them in order of importance, and then attack them until completion, while avoiding distractions.” Be prepared to list an example of an impressive accomplishment.

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Now is not the time to tell the interviewer how you cannot work any extra hours because you are training for the Iron Man Triathlon and have a sick parent and see a therapist five times a week. The best answer is, “Though I pride myself on time-management and prioritisation skills, I realise that extra time is sometimes needed.”