Silly interview questions and what they really mean

What is your greatest flaw?

Why it's silly: Who in their right mind would give an honest answer to this question? Reveal your flaws to the person who's got your future in the palm of their hands? No thank you. In response to questions like this, we tend to conjure up answers that don't give a completely negative impression, such as “My time management could do with a bit more work. I put in extra hours, even at home.”    
What it really means:  The purpose of this question is to gauge out the truth from the half-truth. “I work too hard” is not an obstacle or a flaw that you can work on. You can't just work less hard. A legitimate answer would be to say you're not great at teamwork. This is a clear area for improvement and from there onwards, you can talk about what you've been doing to overcome this weakness to become a better team player.

What do you want to be doing in five years?

Why it's silly: It might not hit you at first, but this question can't possibly have a definite answer. No one can plan that far ahead into the future. Opportunities sprout up, choices change. Life happens. But most candidates would steer clear of an answer that could suggest possible disloyalty to the company in the future anyway. That's why this question is a great way for the interviewer to pick your brain.
What it really means: The first thing you should know is that no company can expect you to swear a lifelong allegiance to it, especially not during your interview. Instead, talk about your career development plan, personal goals, broader interests, and how these can develop with the company. Definitely discuss your areas of strength as well as areas where you want to grow in the most.

Why did you pick this company?

Why it's silly: Sure this question is a little inconsequential. Why on earth would you be sitting in this chair right now if you weren't interested in this company? As long as you fit the JD, what does it matter why you picked this company?
What it really means: The interviewer simply wants you to identify your motives for applying. Are you just looking for a paycheck? Or are you miserable at your current job? These probably aren't answers the interviewer wants to hear. They want to know what excites you about the company and the opportunity. You need to draw a connection between your interests and your abilities and the position you're applying for.

What do you do in your spare time?

Why it's silly: A bit personal and a bit redundant is your first thought. What does playing football have to do with accounting? Or jogging with being an architect? This question crosses the line between work and pleasure, and it'll confuse the interviewee who cannot elaborate on how their hobbies add value to their lives.
What it really means: First of all, the interviewer has no intention of poking his nose into your private life. The interviewer is simply trying to make to find out more about you. Your hobbies can say a lot about how you work. Having more a wide variety of interests might mean you'd be suited for a creative position. If you're running a personal initiative on the side, it gives the interviewer a good picture of how you prioritize your time, and where your job fits in. Being involved in a sport or other physical activity can suggest you're in good health, and you're active and focused. It's also important to not just state your hobbies, but also discuss how it enriches your life or refreshes your mind.

What do your coworkers think of you?

Why it's silly: We can never know exactly what another person thinks of us, especially if you have a professional relationship with that person. If they've already let their feelings be known, and ruthlessly so, you're probably going to talk around the truth to make yourself look better. The interviewer will never know, so what's the harm in a little white lie?
What it really means: The best thing to do is cut down on the embellishing. It's an indirect way of asking how you view yourself and value your abilities. Are you helpful or withdrawn? It is also a modesty test, dividing those who love to go on about themselves and those who are more embarrassed to talk about themselves. Whatever you decide to say, try to find a good balance between the good's and the bad's.