Tough Interview Questions and How to Answer Them

Getting an interview for a position you really want can be both exciting and nerve-wracking. Sure, your resume is great, and you know you’ll be a perfect fit for the job, but the night before the interview you find yourself lying awake imagining all of the potentially embarrassing things that might happen to you. I’ve been there. One of the major reason interviews can be so stress-inducing is because candidates are being put on the spot. Questions can fall anywhere between the extremely open-ended (“Tell me about yourself”) to the excruciatingly specific (“Give me an example of one way you improved your last company’s sales strategies”).

I’ve made my fair share of slightly horrifying interview mistakes. Part of perfecting your interview skills just involves practice. All it took was one interview for me to learn that asking the hiring manager at Circuit City what a gigabyte was probably didn’t make me seem like a strong candidate. But what about the questions every interviewer asks, those dreaded questions no career expert seems to be able to agree on how to answer? I’ve put together a list of the most common – and, in my opinion, hardest to answer – questions one might encounter in an interview, and the best way to answer them. So read on, relax, and remember to sleep the night before your interview!


  1. 1.    Tell Me About the Worst Boss You’ve Ever Had 

    This question just screams “trap!” doesn’t it? The employer is looking out for a couple of things with this question. They want to know whether or not you’re a team player – i.e., if you’ve had problems with people you’ve worked with in the past – and if your preferred management style is a good fit for the company. So how do you put a good spin on a bad boss? According to TheLadders, a career advice website, you should remember that even your worst boss got their position for a reason, and try to consider these positives in your answer.For example, you might qualify your answer with something like this: “My worst boss, that’s a hard question. Each of my bosses had something to teach me.” Having a negative response at the ready makes you seem like a negative person.

    It’s okay to answer truthfully, but you need to give a professional reason. If you’re actually thinking, “Jane was a terrible boss. She never liked anything I did and was too passive-aggressive to say it to my face,” what you should tell the interviewer is, “My last boss, Jane, gave me great projects to work on and we worked at a very fast pace. As a result, she sometimes assigned me projects without much communication. This required me to be more independent and assertive in my work, which is a skill I’m glad to have.” It’s good to turn the negative back into a positive. Even bad bosses have something to teach us, and this is the kind of awareness your future employer will be glad to see.

  2. 2.    Tell Me About Yourself 

    This is the question I have always hated the most. It’s so open-ended, and used to lead to me babbling endlessly about things I thought might be relevant. However, what’s important here is to be concise. Talk about your professional strengths – where have you worked, what kinds of accolades have you received, what are you good at. According to CNN, “Your answers should be a quick rundown of your qualifications and experience. Talk about your education, work history, recent career experience and future goals.” What your employer isn’t concerned with is where you grew up, what kind of wood you like your desk to be made out of, or what year your Uncle Ned won the National Spelling Bee.For example, my answer to this question might be something like this: “I’m about to graduate from Chatham University, and while working there I have held a job in the Career Development Office where I wrote weekly blog posts and worked on X and Y. I also read query letters for a literary agency, where I requested a manuscript which ended up getting published by Publishing House B. While I’ve learned a lot during my time at Chatham, I’m looking to blend my reading skills and office experience in an admissions department like this one.”

    Remember, be brief, be positive, talk about professional successes. Prepare your answer in advance. Know your strengths, and be ready to go into detail about your strengths if asked. You should also research the company as well as possible before your interview. Just like you tailor your resume to a specific employer, you should focus on strengths that will interest the interviewer. A PR firm won’t be interested in your biochemistry degree unless you can show them how it’s related. The more prepared you are, the better.

  3. 3.    What Are Your Weaknesses? 

    Ah, the horrible weaknesses question. Career experts give conflicting advice. Should you mask a strength as a weakness? Should you admit your fatal flaw? The answer, it seems, is somewhere in the middle.Identify an actual weakness. Employers know when you’re trying to pull the wool over their eyes, and they don’t want to hear about how you just care too much or how you’re just too much of a giver. The trick is to lay out a weakness and explain how you think this company will give you an opportunity to make it a strength. You might say, “If I had to think of a weakness, I would say that my last position didn’t ask me to take the lead on as many projects as I would have liked. I would love the opportunity to expand my leadership skills at Company X.” This way, your weakness becomes an opportunity, and the hiring manager will see that you want to grow as an employee.

    Also, never use superlatives. As CareerRealism points out, saying things like, “my worst weakness,” or “my biggest problem,” leads employers to think there are many others. If you frame the negative inside of a positive, the weakness doesn’t seem as bad.


  4. Why Did You Leave Your Last Job? 

    As TheLadders points out, this isn’t the time to bad-mouth anybody in your former office. Staying positive seems to be a recurring tip for each question, but positivity is really one of the most important elements in an interview. Employers want to hire people who will make the office a better place, and as someone who has worked with her share of negative people, I can say that I wouldn’t want to hire anyone who already put out a negative vibe during the interview. Other things not to say include leaving because of pay-scale or because the work was too boring. You don’t want the hiring manager to see you as someone who will leave as soon as things hit a lull.So what should you say? This is a great time to talk about your career goals. Talk about a few strengths you gained from your last job, and how you would be interested to apply these skills to a different area. What new skills would you like to acquire that this new employer can offer? If you frame your exit as a completed project, you’re telling this potential new employer that you aren’t a flight risk, says Stephen Balzac, president of 7 Steps Ahead, a business consulting firm in Massachusetts. You want this employer to see that you’ll be here until you’ve learned everything and accomplished everything you can.

    But what if you were laid off? With the economy in such a bad state, people are getting laid off more frequently. It’s important to be honest, even if you don’t know why you were laid off. suggests an answer like this one: “As you know, the economy is tough right now and my company felt the effects of it. I was part of a large staff reduction. I am confident, however, that it had nothing to do with my job performance, as exemplified by my accomplishments.” Always bring the answer back to your strengths.

The most important thing to remember during an interview is to stay positive. If you have to say something negative, say it quickly and move on to something strong about you. Focus more on your strengths rather than past employers’ weaknesses. Also remember, it’s okay if you make a mistake. As my high school band director used to say (yes, yes, I know, I’m really quoting my high school band director): “Your mistake doesn’t matter, all that matters is how you recover.” If you do slip up, don’t be afraid to go back and correct yourself. As long as you’re prepared, you should be confident enough to make the most out of any job interview.

By: Amanda Hart

Amanda is a second-year student in Chatham’s Creative Writing MFA program. She currently works as a Graduate Associate in the Career Development office and as an intern for Upstart Crow, a local literary agency.

09. February 2012 by careerdevelopment
Categories: Uncategorized | Leave a comment

Leave a Reply

Required fields are marked *

Skip to toolbar