15 Toughest Interview Questions and Answers
1. Why do you want to work in this industry?
“I love to shop. Even as a kid, I spent hours flipping through catalogues.”
Don’t just say you like it. Anyone can do that. Focus instead on your history with that
particular industry, and if you can, tell a success story.
“I’ve always loved shopping, but my interest in retail marketing really started when I worked at a neighbourhood
boutique. I knew our clothes were amazing, but that we weren’t marketing them properly. So I worked with
management to come up with a marketing strategy that increased our sales by 25% in a year. It was great to be able
to contribute positively to an industry I feel so passionate about, and to help promote a product I really believed in.”
2. Tell us about yourself?
“I graduated four years ago from the University of Michigan, with a Bachelor’s in Biology – but I decided that
wasn’t the right path for me. So I switched gears and got my first job, working in sales for a startup. Then I went on
to work in marketing for a law firm. After that, I took a few months off to travel. Finally, I came back and worked in
marketing again. And now, here I am, looking for a more challenging marketing role.”
Instead of giving a chronological work history, focus on your strengths and how they
pertain to the role. If possible, illustrate with examples.
“I’m really energetic, and a great communicator. Working in sales for two years helped me build confidence, and
taught me the importance of customer loyalty. I’ve also got a track record of success. In my last role, I launched a
company newsletter, which helped us build on our existing relationships and create new ones. Because of this, we
ended up seeing a revenue increase of 10% over two years. I’m also really interested in how companies can use web
tools to better market themselves and would be committed to building on your existing platform.”
3. What do you think of your previous boss?
“He was completely incompetent, and a nightmare to work with, which is why I’ve moved on”
Remember: if you get the job, the person interviewing you will someday be your previous
boss. The last thing they want is to hire someone who they know is going to badmouth them
some day. Instead of trashing your former employer, stay positive, and focus on what you
learned from him (no matter how awful he really was).
“My last boss taught me the importance of time management – he didn’t pull any punches and was extremely
deadline-driven. His no-nonsense attitude pushed me to work harder, and to meet deadlines I never even thought
4. Why are you leaving your current role?
“I can’t stand my boss or the work I’m doing.”
Again, stay away from badmouthing your job or employer. Focus on the positive.
“I’ve learned a lot from my current role, but now I’m looking for a new challenge, to broaden my horizons and to
gain a new skill-set – all of which, I see the potential for in this job.”
5. Where do you see yourself in five years?
“Relaxing on a beach in Maui,” or “Doing your job.”
There’s really no right answer to this question, but the interviewer wants to know that
you’re ambitious, career-oriented, and committed to a future with the company. So instead
of sharing your dream for early retirement, or trying to be funny, give them an answer that
illustrates your drive and commitment.
“In five years I’d like to have an even better understanding of this industry. Also, I really love working with people.
Ultimately, I’d like to be in some type of managerial role at this company, where I can use my people skills and
industry knowledge to benefit the people working for me, and the company as a whole.”
6. What’s your greatest weakness?
“I work too hard,” or for the comedian, “Blondes.”
This question is a great opportunity to put a positive spin on something negative, but you
don’t want your answer to be cliché – joking or not. Instead, try to use a real example of a
weakness you have learned to overcome.
“I’ve never been very comfortable with public speaking – which as you know, can be a hindrance in the workplace.
Realizing this was a problem, I asked my previous employer if I could enrol in a speech workshop. He said “yes.” I
took the class and was able to overcome my lifelong fear. Since then, I’ve given lots of presentations to audiences
of over 100 high-level executives – I still don’t love it, but no one else can tell!”
7. What salary are you looking for?
“In my last job I earned $35,000 – so, now I’m looking for $40,000”
If you can avoid it, don’t give an exact number. The first person to name a price in a salary
negotiation loses. Instead, reiterate your commitment to the job itself. If you have to, give
a broad range based on research you’ve conducted on that particular role, in your
“I’m more interested in the role itself than the pay. That said, I’d expect to be paid the appropriate range for this
role, based on my five years of experience. I also think a fair salary would bear in mind the high cost of living here
in New York City.”
8. Why should I hire you?
“I’m the best candidate for the role.”
A good answer will reiterate your qualifications and will highlight what makes you unique.
“I’ve been an Executive Assistant for the past ten years – my boss has said time and time again that without me, the
organization would fall apart. I’ve also taken the time to educate myself on some of the software I regularly use (but
didn’t really understand the ins and outs of). I’m an Excel wiz now, which means I can work faster, and take over
some of what my boss would traditionally have had to do himself. What’s good enough for most people is never
really good enough for me.”
9. What is your greatest failure, and what did you learn from it?
I never finished law school – and everything that’s happened since has taught me that giving up, just because of the
going gets tough, is a huge mistake.”
You don’t want to actually highlight a major regret – especially one that exposes an overall
dissatisfaction with your life. Instead, focus on a smaller, but significant, mishap, and how
it has made you a better professional.
“When I was in college, I took an art class to supplement my curriculum. I didn’t take it very seriously, and assumed
that, compared to my Engineering classes, it would be a walk in the park. My failing grades at midterm showed me
otherwise. I’d even jeopardized my scholarship status. I knew I had to get my act together. I spent the rest of the
semester making up for it, ended up getting a decent grade in the class. I learned that no matter what I’m doing, I
should strive to do it to the best of my ability. Otherwise, it’s not worth doing at all.”
10. How do you explain your gap in employment?
“I was so tired of working, and I needed a break,” or “I just can’t find a job.”
Employment gaps are always tough to explain. You don’t want to come across as lazy or
unhireable. Find a way to make your extended unemployment seem like a choice you made,
based on the right reasons.
“My work is important to me, so I won’t be satisfied with any old job. Instead of rushing to accept the first thing that
comes my way, I’m taking my time and being selective to make sure my next role is the right one.”
11. When were you most satisfied with your job?
“I was most satisfied when I did well and got praised for my work.”
Don’t give vague answers. Instead, think about something you did well – and enjoyed –that
will be relevant at this new job. This is an opportunity for you to share your interests,
prove that you’re a great fit for the job and showcase your enthusiasm.
“I’m a people person. I was always happiest – and most satisfied – when I was interacting with customers, making
sure I was able to meet their needs and giving them the best possible customer experience. It was my favorite part of
the job, and it showed – I was rated as “Good or Excellent” 95% of the time. Part of the reason I’m interested in this
job is that I know I’d have even more interaction with customers, on an even more critical level.”
12. What did you like least about your last job?
“A lack of stability. I felt like the place could collapse around me at any time.”
Try and stay away from anything that draws on the politics, culture or financial health of
your previous employer. No matter how true it might be, comments like these will be
construed as too negative. Also, you don’t want to focus on a function that might be your
responsibility in the next role. So think of something you disliked in your last job, but that
you know for sure won’t be part of this new role.
“There was nothing about my last job that I hated, but I guess there were some things I liked less than others. My
previous role involved travelling at least twice a month. While I do love to travel, twice a month was a little
exhausting – I didn’t like spending quite so much time out of the office. I’m happy to see that this role involves a lot
13. Describe a time when you did not get along with a coworker?
“I’m easy to get along with, so I’ve never had any kind of discord with another coworker.”
Interviewers don’t like these types of “easy out” answers. And besides, they know you are
probably not telling the truth. Think of a relatively benign (but significant) instance, and
spin it to be a positive learning experience.
“I used to lock heads with a fellow nurse in the INCU ward. We disagreed over a lot of things – from the care of
patients to who got what shifts to how to speak with a child’s family. Our personalities just didn’t mesh. After three
months of arguing, I pulled her aside and asked her to lunch. At lunch, we talked about our differences and why we
weren’t getting along. It turns out, it was all about communication. We communicated differently and once we knew
that, we began to work well together. I really believe that talking a problem through with someone can help solve
14. What motivates you?
“Doing a good job and being rewarded for it.”
It’s not that this answer is wrong – it’s just that it wastes an opportunity. This question is
practically begging you to highlight your positive attributes. So don’t give a vague, generic
response – it tells them very little about you. Instead, try and use this question as an
opportunity to give the interviewer some insight into your character, and use examples
“I’ve always been motivated by the challenge of meeting a tough deadline – in my last role, I was responsible for a
100% success rate in terms of delivering our products on time and within budget. I know that this job is very fastpaced and deadline-driven – I’m more than up for the challenge. In fact, I thrive on it.”
15. How would your friends describe you?
“I’m a really good listener.”
While being a good listener is a great personality trait, your employer probably doesn’t
care all that much. It’s unlikely that they’re hiring you to be a shoulder to cry on. You’ll
want to keep your answer relevant to the job you’re interviewing for – and as specific as
possible. If you can, insert an example.
“My friends would probably say that I’m extremely persistent – I’ve never been afraid to keep going back until I get
what I want. When I worked as a program developer, recruiting keynote speakers for a major tech conference, I got
one rejection after another – this was just the nature of the job. But I really wanted the big players – so I wouldn’t
take no for an answer. I kept going back to them every time there was a new company on board or some new value
proposition. Eventually, many of them actually said “yes” – the program turned out to be so great that we doubled
our attendees from the year before. A lot of people might have given up after the first rejection, but it’s just not in
my nature. If I know something is possible, I have to keep trying until I get it.”