15 Most Difficult Interview Questions (and their Possible Answers)

For many people, job
interviews are the most stressful part of the job-search process. And it’s true
that an interview is often a make-or-break moment: If you flub the interview in
a big way, you probably won’t make the cut–no matter how good your resume is,
or how excellent your qualifications are.

You can combat nerves
and increase your chances of success by practicing your answers to difficult
interview questions. Here are some of the toughest, with suggested answers:
1.
Why do you want to work in this industry?
Bad
answer:

“I love to shop. Even as a kid, I spent hours flipping through catalogs.”
Tip:
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.
Good
answer:

“I’ve always loved shopping, but my interest in retail marketing really started
when I worked at a neighborhood boutique. I knew that 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 percent 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.
Bad
answer:

“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.”
Tip:
Instead of giving a
chronological work history, focus on your strengths and how they pertain to the
role. If possible, illustrate with examples.
Good
answer:

“I’m really energetic, and I’m 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
percent over two years. I’m also very 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?
Bad
answer:

“He was completely incompetent, and a nightmare to work with, which is why I’ve
moved on.”
Tip:
Remember that if you get the job, many of the people interviewing you will
someday be your previous bosses. The last thing they want is to hire someone
they know will badmouth them. Instead of trashing your former employer, stay
positive, and focus on what you learned from him (no matter how awful he really
was).
Good
answer:

“My last boss taught me the importance of time management, 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 were possible.”

4.
Why are you leaving your current role?
Bad
answer:

“I can’t stand my boss, or the work I’m doing.”
Tip:
Again, stay away from badmouthing your job or employer. Focus on the positive.
Good
answer:

“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?
Bad
answer:

“Relaxing on a beach in Maui,” or “Doing your job.”
Tip:
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 an answer that illustrates your drive and commitment.
Good
answer:

“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?
Bad
answer:

“I work too hard,” or for the comedian, “Blonds.”
Tip:
This question is a great opportunity to put a positive spin on something
negative, but you don’t want your answer to be a cliche–joking or not. Instead,
try to use a real example of a weakness you have learned to overcome.
Good
answer:

“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 enroll in a speech workshop. I took the class, and
was able to overcome my lifelong fear. Since then, I’ve given several
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?
Bad
answer:

“In my last job I earned $35,000–so now I’m looking for $40,000.”
Tip:
“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 particular city.”
Good
answer:

“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?
Bad
answer:

“I’m the best candidate for the role.”
Tip:
A good answer will reiterate your qualifications, and will highlight what makes
you unique.
Good
answer:

“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 whiz now, which
means I can work faster, and take over some of what my boss would traditionally
have had to do herself. 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?
Bad
answer:

“I never finished law school–and everything that’s happened since has taught me
that giving up, just because the going gets tough, is a huge mistake.”
Tip:
You don’t want to highlight a true major regret–especially one that exposes an
overall dissatisfaction with your life. Instead, focus on a smaller (but still
significant) mishap, and how it has made you a better professional.
Good
answer:

“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?
Bad
answer:

“I was so tired of working, and I needed a break,” or “I just can’t find a
job.”
Tip:
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.
Good
answer:

“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.”

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