Resources: ArticleToughest Interviewing Questions

We all know that it can be nerve-wracking and intimidating to go in for an interview. However, the situation that every job hunter fears is being confronted with a question that calls for a blank stare and a panicked scramble for a response.

Job hunters, have no fear! Here is our list of the toughest interview questions and tips on how to answer them:

  1. “Tell me about yourself”

    WHAT IT IS: A commonly used opening question;  this is supposed to be a brief introduction to you and your previous experience (not your entire life story!)

    WHAT TO THINK ABOUT IN ANSWERING: Make it brief, simple and to the point. Don’t mention information that is too personal or irrelevant. Candidates tend to carry on because they don’t know what to say, but mention the basics like education and recent work experience.

  2. “Why should I hire you?”

    WHAT IT IS: A chance for you to show your potential employer why you are qualified to be great fit for the position.

    WHAT TO THINK ABOUT IN ANSWERING: Emphasize strengths and past work experience that will correlate to the duties listed in the job description. Make sure you’ve done your due diligence on the company and the position for a more effective and well-rounded response.

  3. “What is your greatest weakness?” or “Why shouldn’t we hire you?”

    WHAT IT IS: More than anything, this question serves as a way for employers to identify red flags for each candidate. In essence, this is a question designed to weed out candidates.

    WHAT TO THINK ABOUT IN ANSWERING: Identify a point on your resume that may already be an obvious weakness and address it (are you missing experience with a software program that they prefer you to use?  do you have different investment product knowledge that isn’t as relevant?)  If it was a deal breaker, they wouldn’t have brought you in for an interview! You don’t want to shoot yourself in the foot and tell them something that could eliminate you from consideration. Be straightforward and identify something that they already know about you based on your resume. 

  4. “Why did you leave your last job?” or “Why are you looking to leave?”

    WHAT IT IS: A question you are guaranteed to hear in each interview to get to the root of why you are on the job search and why you’re interviewing with the company. What is going on?

    WHAT TO THINK ABOUT IN ANSWERING: Never ever badmouth a previous boss or work experience. This only serves to create a bad impression for your potential employer – certainly not the best way to start. Instead, focus on specific aspects of why the job wasn’t a great fit or a recent change that led you to search (high turnover rate, recent layoffs, changes in management, etc.) OR focus on what this new position offers and why it has you opportunistically pursuing the role. 

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

    WHAT IT IS: Ultimately a company doesn’t want someone who intends to leave right away, so this question is a way for employers to contextualize how the position would fit into your long-term career goals.  A candidate of ours who was interviewing with a hedge fund once told the hiring manager that he wanted to become an interior designer…. the employer didn’t exactly have that in their five-year plan for him.  Sometimes being too honest about your future can cost you a current opportunity. 

    WHAT TO THINK ABOUT IN ANSWERING: Be honest, but not extremely specific. After all, no one can explicitly predict where they will be in five years. Present your goals in a way that shows that the position you are interviewing for fits into your long-term plan. Make sure your answers have depth and be prepared for follow up questions, but most of all, display a sense of purpose and motivation.