3 Tricky Interview Questions and How to Answer Them

All interview questions are not created equally. Some only require you to provide basic information, while others require long answers and can be very hard to navigate. Below you’ll find three questions that fall into the latter category, along with specific tactics for how to answer them.

1. “What’s your greatest weakness?”

This is one of the most common and challenging interview questions. It’s so common, in fact, that it’s referenced in television shows, books, and movies.

Interviewers ask this question for two reasons. One is to find out your flaws ahead of time so they know whether you’ll be a good employee or not. The other reason is to get a better understanding of your self-awareness. So, what they’re really asking is, “Can you critically look at your skills and capabilities and find areas for improvement? Or will you require constant evaluation and criticism from your manager?”

As for how to answer this question, aim for an honest and thoughtful answer. Do you struggle with time management? Is writing not your strong suit? Let your interviewer know that. And don’t stop there. The most important part of your answer comes next: Tell your interviewer what you’re doing to improve. Have you started using a time management tool? Do you have a strict self-editing process to catch mistakes? This will show your interviewer that you’re both honest and self-motivated. That’s sure to satisfy their needs. 

2. “Where do you see yourself in five years?”

Some people are just born with a plan. They know exactly where they are, where they want to be, and how to get there. Others use more of a “take life as it comes” approach. This is especially true for people who’ve just recently entered the workforce. They often don’t have a clear vision for where they’ll be in five years. If you’re one of the latter, this can be a challenging question to answer.

Typically, employers ask this question to get a better idea of your “bigger picture.” It helps them understand more about your professional passions and aspirations beyond just your experience. Furthermore, it can give your potential employer a clear picture of whether this role aligns with your goals. If your aspirations are in line with what they can offer, it can help them tailor the role to your desires. If not, it may be an indication that you’re unlikely to stick around.

As for how to answer this question, since it’s so open-ended, it can be easy to get carried away. For example, if you’re interviewing for a job in marketing with a large health care company, your prospective employer probably doesn’t want to hear about your aspirations to start your own CBD company. So, instead of thinking generally about where you see yourself in five years, think about where you see yourself within the company in five years. How might you grow with this company? Which skills or roles offered by this position are you particularly interested in? Tell your interviewer that.

Typically, employers are looking for people who want to build careers with their companies. And even if they understand that people switch jobs often these days, they don’t want to hear about your aspirations to leave before you even join.

3. “How many United Airlines planes will take off in the next hour in the U.S.?”

This is what is called a guesstimate or brainteaser. It comes in many forms. It might be something like: “How many ATMs are there in the U.S.?” Or: “How many square feet of pizza are eaten across the U.S. each day?” No matter what exactly is asked, by design there are no right, exact answers to questions like these. That’s because the point of these types of questions isn't getting the correct answers; it’s your thought process that matters.

Do you stay calm? Or are you totally thrown you off and start to get nervous? Do you attempt to answer the question and think it through? Or do you simply say “I don’t know” and move on? Does your answer show critical thinking?

How you react to these questions can be a good indication of how you’d react to something unexpected in your role. So, when answering, the most important thing to remember is to keep your cool. Don’t let the question throw you off, and definitely don’t react negatively to it. Your reaction should let your interviewer know that you’re game for anything.

Next, it’s time to work out an answer. Remember that your answer is supposed to highlight your critical thinking ability. Break the question down into its components and think through them aloud to "show your work." Don't forget that the answer your interviewer is looking for is not the actual answer but a sensible way of getting to the answer. 

As for how to field this particular question about planes, there are a few ways to go about answering it. One is to begin by trying to estimate the number of large U.S. airports that would have United Airlines planes. For ease, if you estimate that each U.S. state has two big airports, then you come up with 100 airports. Then, as for the next step, you might try to estimate how many United Airlines planes take off each hour. If you think that maybe one United Airlines plane departs every 15 minutes at each airport, you can see that four take off per hour from each airport. This means you can estimate that there are 400 (100 x 4) United Airlines planes taking off each hour in the U.S.

Is that the exact, right answer? Probably not! But you answered exactly what was asked of you. 

Matt Casadona has a Bachelor of Science in Business Administration, with a concentration in marketing and a minor in psychology. He is currently a contributing editor for 365 Business Tips. Matt is passionate about marketing and business strategy, and enjoys the San Diego life, traveling, and music.