How to Answer These Difficult Interview Questions

Share this post

I work as a guidance counselor in a private high school and we have this annual event for senior high school students called “Career Week.” Basically, we get speakers from various career paths to talk about their job, universities and colleges to hold fairs, and have one day where the seniors come to class in corporate attire and attend “interviews” – that is, one-on-one mock interviews with guidance counsellors – complete with job descriptions posted on the bulletin boards at the beginning of the week and resumes to fit that position.

Having been in charge of the senior high school students for over six years now, one of the most common feedback I get from the other counselors is how most students – yes, even the brightest ones you’d expect would get job offers even before getting their hands on their college diploma – crashed and burned at some of the most difficult job interview questions. I can forgive them for it, given that they are just high school students, but these are 18 and 19-year old young adults who should already have an idea on how to go through an interview.

But it’s not just my students that are struggling with these questions. Apparently, even fresh graduates and adults struggle with these difficult questions. I think the most important thing people should understand is that, for every question your interviewer gives, there is an underlying purpose as to why they asked that. To be honest, most of them are not interested in your answer as is, but how you take that question and use it to highlight your best qualities for the position.

So, when you’re asked these tough questions in your job interview, these are the best responses you can give.


Introduce yourself. Can you tell us something that’s not on your resume?

This may be a genuine question to get to know you better or a question to throw you off your game, but either way, it’s an opportunity to put your best foot forward at the start of an interview. Don’t be intimidated by the “something that’s not on your resume” bit because a lot of job applicants tend to just recite everything that’s on their resume.  It’s a waste of time for both parties involved and it leaves them learning nothing new about you as a potential candidate.

It goes without saying that you should avoid mentioning negative points about yourself as well as unnecessary information. A brief sentence or two about where you were born and raised or something about your family can make you seem personal, but when you talk too much about hobbies and private information about your personal life is a waste of time.

Make your answer short, concise, like an elevator pitch. This question provides your interviewer’s first impression of you and whether or not they will like you, but you need to do this in as little time as possible, like you’re giving a pitch timed by a short elevator ride.

A good answer should address the following: why are you here? Why are you interested in this position? What can you offer us that other candidates can’t? How you can answer that under pressure is up to you, but an ideal answer would look like this:

“My name is X. I chose to major in Literature because I’ve always been an avid reader and writer and I believe that people tend to underestimate the worth of an arts degree in today’s job market. I was born and raised in Y and was taught the value of hard work from an early age. I believe my writing experience and skills I picked up in college, along with my perseverance and eye for quality, can be beneficial for your company and provide a fresher take on what it is content writers provide their company.”

In this case, you’re stating what you can do, what you can offer, and a unique selling point other candidates may not provide. You’ve done this in as little time as possible, making your answer an efficient one.


What is your greatest weakness?

You may be tempted to say you don’t have one, but this is the one answer you should never say. Everyone has a weakness, and saying that not only provides little options for the interviewer to continue, but it could go against you for not being creative enough to think of a good answer.

Don’t offer answers where it’s clear you don’t consider it a weakness. Things like being a perfectionist or being a night owl is such a safe answer that isn’t really a weakness, and your interviewer will know you’re not being honest.

The best way to answer? Admit one flaw, and then turn it around and show honest and positive solutions that make it a positive thing. Don’t say a flaw that will immediately cost you the job (e.g. “I’m not a people person, I’d rather work alone” for a position that specifically says in the job description that you’ll be working in a team) but something that is related to the position. You can either say something like turn a negative trait into a positive light:

“My time management skills. While I rarely submit tasks later than the deadline, you should never expect me to finish earlier than the deadline. If you give me a task and say it’s due at midnight, I’ll submit it on 11:59 PM. That’s because whenever I finish early, I tend to go over the output again and again. I try to find areas where I can improve, and that sometimes involve huge changes to what I’ve completed. So, as long as I know I have time before the deadline, I’m going to keep working and improving, so I rarely submit early.”

In this example, you’re turning your weakness – your time management skills – into a strength – submitting quality output each time.


What did you dislike about working in your previous job? / Why are you leaving your previous job?

If you’re leaving your job for one reason, chances are, you’ll be leaving your next job for the same reason. If you left your last job because of stress, competition, or because your supervisor was criticizing your work, chances are you’re going to find these things in your next job, so the interviewer could think you might not be a good fit for the position you’re applying for.

Your interviewer wants to get a feel about how you handle your workplace situation, your co-workers and supervisors, and how you handled your last job. While you may have negative emotions about your last job, set them aside and try not to say anything that hints you could leave this position if faced with the same problem.

“I didn’t like that there was little room for growth. My co-worker who was on the same job level as I was has been in that company forover eight years and by now knows all the ropes of the department. But instead of considering her for the manager position, they’ve externally hired managers each time. I don’t think, long-term, I can grow from the position I have, so I’m looking for a position with a job description that promises growth in a company that cares for its employees. And based on what I’ve read online, I strongly believe that position is here.”

Don’t be negative about your last job because it will say a lot about who you are as an employee.


Why shouldn’t we hire you?

It’s easy to explain why the company should hire you. It’s another thing to explain why they shouldn’t hire you. This is one of the curveball questions that keeps you on your toes. Just like “What’s your weakness?”, ending this question with “There’s no reason to not hire me.” Is uncreative and shows the interviewer that you crash when posed with a challenging question. When answered correctly, though, you can highlight your best points and show how well you respond to the challenge.

Like when stating your weakness, never take the question literally and say something that will cost you the job. Say something like “Don’t hire me because I actually use your competitor’s products at home” or “Don’t hire me because I’m actually very lazy” is the same as saying “Don’t hire me.”

Instead of talking about weaknesses, talk about the work strengths that apply to some office cultures, but not all. For example, if you prefer to not be micromanaged, say something along the lines of “Don’t hire me if your company forces its employees to operate a certain way and leaves no room for innovation or the ability to think out of the box” or “You shouldn’t hire me if your company does not have a good work-life balance.”


What do you know about our company?

I’ve heard of stories from my friends who work in Human Resources of their respective companies about promising employees who come prepared knowing what the job position says, but the moment you ask what they know about the company, they’re completely blank-faced. It’s embarrassing, admitting you don’t know about the company you’re applying for, and it shows that you’re unprepared and making a huge job decision without learning the facts about what this company does.

The best way to answer this is to actually do your research. Don’t just read the comments on job websites about a certain company from former employees. Read their website, their About Us, and the services they provide their customers. And once your interviewer asks you this question, relate what you know about the company to your own skills. Remember, even in questions like these, you have to keep selling yourself.

“I know that company so-and-so has been a figure in the digital marketing industry for over nine years. Apart from SEO, you also provide other services such as web optimization, social media services, reputation management, and more. You also advertise yourselves as a provider of top-quality marketing content, a product which I have had years of experience providing in my previous job.”


A job interview can seem difficult and intimidating, and that’s because it is. During an interview, stay on your toes, do your research beforehand, and watch out for any curveballs. Remember to sell yourself and highlight your strengths, and avoid mentioning weaknesses if you don’t have anything to turn it into a positive answer.

About The Author

Scroll to Top