The Top 10 Toughest Interview Questions (and how to handle them)

Don’t let these passive aggressive questions trap you.

Do you fear those certain interview questions that we all fear?

Are you looking for ways to avoid these evil interview questions?

It turns out that there is a lot you can do to prepare yourself if you are wary of what your next interview will bring.

In this article, you’ll learn how to deal with the top 10 toughest interview questions you could ever encounter.

The Top Ten Toughest Interview QuestionsFor a lot of people, job interviews can be pretty scary. Nevertheless, if you are to succeed in presenting your personal brand, you’ll have to think deeply about just how to handle tough interview questions. Job interviews are especially difficult because they often play out more like an interrogation rather than just a normal conversation. I won’t get into my thoughts on the “state” of job interview culture today, though. Instead I’m going to give you some ideas on how to best handle these dastardly inquiries without selling your soul to the corporate machine. Yes. You can look good and retain your soul.


Tough Interview Question #1:

“Why did you quit you last job?”

Tough Interview Questions - Why did you quit your last job?

What you want to say: Why did I quit my last job? Because it was awful. The people stunk. The environment stunk. The bathroom literally stunk. What kind of question is that? I wasn’t happy! I thought I could do better. I wasn’t getting paid enough. My boss was a jerk. WHY DOES ANYBODY EVER LEAVE A JOB?

What you should say: Ninja skills are needed for this kind of question. It’s very easy to give a robotic response like, “I’m looking for something new” or “I’m trying to move forward in my career”, but I would suggest something a little different. Twist the question slightly in your favor. Tell them you didn’t necessarily want to leave your last (or current) job, but that it was necessary for you to continue to grow. You could talk about some of the aspects of your last job that you actually liked, while at the time talking about what you like about the job you are interviewing for. This way you can answer the question naturally without totally deflecting it. Check this link below for a few more ideas.

Read this for more: HOW TO ANSWER: Why Did You Leave Your Last Job?


Tough Interview Question #2:

“Why is there a gap in your work history?”

Tough Interview Questions - There's a Gap in Your Work History

What you want to say: Why is there a gap in my work history? How about because I have a life? Or I have a child I decided not to neglect for a while. Or my parents got sick. Or maybe it’s just what YOU think: I’m an alcoholic drug addict who loves to gamble and spends tons of cash on hookers. There you go. You got the dirt. Are you satisfied?

What you should say: I really don’t know why it’s so hard for people to give each other the benefit of the doubt these days. If I’m doing the hiring, I’d be wary of somebody who didn’t have a gap in their work history. The phrasing of the question puts you immediately on the defensive, so we are first going to need some zen. Take a deep breath (in your mind of course) and simply explain in ernest what you were doing – even if it wasn’t the best and most productive use of your time. Maybe your trip across Thailand really opened your mind up to new possibilities? Is that such a bad thing? You could try to cover it up and lie about it, but think long-term. Would you really like to work for a company that has zero empathy? I sure wouldn’t. Life isn’t just about work – take a look at the link below for some awesome vacation ideas well worth creating a “gap” for.

Read this for more: Top 10 Soul Searching Destinations of the World


Tough Interview Question #3:

“What are your weaknesses?”

Tough Interview Questions - What are your greatest weaknesses

What you want to say: Ha! Oh my weaknesses? I haven’t got any. I’m a perfect picture of perfection! What, like you don’t have weaknesses? Why aren’t we focusing on them? Can’t we keep this positive? GET OUT OF MY HEAD.

What you should say: I h-a-t-e this question. It’s so obviously a trap question that it makes asking it kind of sociopathic. I mean, couldn’t we at least change the phrasing? How about “where do you think you can improve?” It’s just pure evil, this one. The conventional wisdom is to take something that really is a strength and exaggerate some aspect of that to make it seem like it’s a weakness to satisfy the requirements of the question. For example, “I really like to improve workflow systems, but something that happens is I ask too many questions and some people tend to get bogged down.” This answer not only makes you look good, it makes it look like other people can’t even handle how good you are.

Super Bonus Future-World Advice: The above answer might be fine, and certainly even recommended, but it still makes me cringe a bit. The fact that we can’t be honest in the game that’s being played here is absurd. I take this question as a direct challenge to my intelligence – not because I don’t think I have any weaknesses, but because the question is an obvious trap – and that’s just not cool bro. These days, when I get this question, I flip it right back and ask the interviewer what the most interesting answer they ever heard to that question was. If they can’t flow with that, could it be a clue that I don’t want to work with this person? I think so. No matter how you answer this question, if your resume gives the interviewer warm, fuzzy feelings, you can can limit the damage. Check the link below for my advice on creating a solid, measurable and quantifiable resume.

Read this for more: How to Make an Achievement Oriented Resume that Pops Using Numbers


Tough Interview Question #4:

“What did you dislike about your last job?”

Tough Interview Questions - What do you dislike about your last job

What you want to say: Everything.

What you should say: Another trap question that forces you focus on the less fortunate aspects of your career. As with most questions of this nature, your challenge will be to take a negative and flip it into a positive. Try to focus on issues that would never be able to reflect poorly on your performance. You might also try to highlight some attempts to solve the problem if applicable. For example, instead of saying your previous company had communication issues, you could say that “there were several workflow systems that limited the effectiveness of communication. As an operations manager, I made it a priority to try and fix those systems.”

Answering these kinds of questions will always be precarious, so in answering always think of your answer as damage control. Coming out with a neutral response is sometimes the best you can do. Again, your resume can help you minimize the damage felt from these questions, especially if you take time to write a resume that demonstrates your ability and highlights the better parts of your nature. Check the link below for more on that!

Read this for more: How to “show” instead of “tell” on your CV


Tough Interview Question #5:

“How would your coworkers describe you?”

Tough Interview Questions - How would your coworkers describe you

What you want to say: Well, since they all loved me unequivocally,  they would probably say that I was a god-like figure in their life, both physically and spiritually. Nuff said.

What you should say: I’ve never understood the angle of this question. Would you ask a new boyfriend or girlfriend this question? An in-law? Anybody outside the context of a job interview? Your best bet here is to stick to what you’ve already described yourself as in your resume, on your LinkedIn profile and in your cover letter. It would be best if you could reference existing testimonials to cut down on the B.S. factor. In my experience, it always sounds smarmy when somebody starts a sentence with something like, “Well, the HR manager at my previous company, Sarah, said that I was… blah blah blah”. Try to set yourself up for success by having your references ready if possible. Check the link below for ideas for some ideas on using LinkedIn to get recommendations.

Read this for more: 5 Best Practices For Requesting LinkedIn Recommendations


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 Tough Interview Question #6:

“What do you think of your last boss?”

Tough Interview Questions - What do you think about your last boss

What you want to say: Oh, you mean The Undertaker? Sorry, I mean Frank. The Undertaker is just my pet name for him. Mostly because of the sense of foreboding he instilled in all those around him with his undead-like aura. What else would you like to know about him?

What you should say: Another – yes – ANOTHER trap question. The interviewer (besides being a totally unrealistic participant in a fantasy life where everybody gets along) is trying their best to throw you off here. Either that, or test the boundaries of your respect and loyalty. Let’s face the music a bit before we dive into my suggestions: there are tons of bad bosses. Yet we live in a world where honesty is valued less and less. Luckily this question isn’t too hard to answer. Keep it short and sweet and don’t say anything negative. Whenever I get this question, I simply say that I learned a lot from my last boss and I was happy to have the opportunity to work with them. Whether the situation was positive or negative, that should always be true.

Read this for more: How To Handle A Bad Boss: 7 Strategies For ‘Managing Up’


Tough Interview Question #7:

“Why should we hire you?”

Tough Interview Questions - Why should we hire you

What you want to say: Duh. I’m the best. It says so on my resume.

What you should say: This question is especially hard because it always leaves me second guessing my answer. It’s a fairly open question, which is good, but don’t fall into the habit of “over-preparing”, or your response might sound robotic. You might also want to be careful about stuffing too many keywords into your answer. Save the keywords for your resume or your LinkedIn profile and keep this answer loose and relaxed. A big part of getting the job is demonstrating that you are a likable person in addition to being qualified. More on not sounding like a robot in the link below.

Read this for more: 9 tips to Nail your Next Job Interview and Get Hired


Tough Interview Question #8:

“Tell me about yourself… Go on…”

Tough Interview Questions - Tell me about yourself

What you want to say: Long walks on the beach, classic rock, popcorn, kitty cats, etc.

What you should say: Again, as before, this is an open-ended and therefore elusive sort of question. What I’ve seen time and time again is people going directly to a pre-fab answer rather than staying in the moment and answering from the heart. Of course, telling you to answer from the heart isn’t the most quantifiable advice, but in this case, the interviewer is trying to feel you out. The question wasn’t “tell me about your experience, education and skills”, so why do most people go there instinctually? Try to relax and answer this question the same way you would in any other kind of conversation. If you met somebody at a party, you wouldn’t start talking about your work experience, would you? It’s all about being natural. Something you can learn more about by clicking the link below.

Read this for more: How to stay calm in a job interview


Tough Interview Question #9:

“Where do you see yourself in 5 years?”

Tough Interview Questions - Where do you see yourself in 5 years

What you want to say: Is this a trick question?

What you should say: In a world that is increasingly competitive, almost anything could be held against you. I’ve been told by several HR managers that they would have doubts about an employee who stayed at a company less than 2 years. So does that mean the answer to this question should include placing yourself 5 years in the future at the same company and position you are interviewing for today? My advice would be to steer clear of the timing. I usually say something like, “In 5 years, I hope to be in a place where I can continue growing professionally.” Short and sweet on these trick questions so you have time to dazzle them when something a little fairer comes around. For some advice on career planning, take a look at the link below.

Read this for more: 10 Tips for Successful Career Planning: An Activity for Job-Seekers of All Ages


Tough Interview Question #10:

“What are your salary expectations?”

Tough Interview Questions - What are your salary expectations

What you want to say: One billion dollars muahahahahaaaa!

What you should say: If you are anything like me, you probably hate asking for money. After all, we’ve spent a lifetime being made to feel like we aren’t good enough (or is that just me?) My advice on this one is to play your cards near your chest and say you are looking for something “competitive with what the market has on offer”. Essentially you are leaving the ball in their court. Now, to be fair, we’ve all heard stories of “Sally” or “Joe” who asked for a crazy high figure and got it, but I believe those cases to be outliers. Be humble. Think long-term. That said, if you do want to play hardball, check the link below for some concrete strategies.

Read this for more: How To Negotiate Your Salary Once You Have The Job Offer

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Ryan - The Resume Ninja

Ryan - The Resume Ninja

The Resume Ninja is Ryan Cordoni. His work in marketing, print design and executive training has transformed him into a finely tuned resume writing machine. And what good is a finely tuned resume writing machine without a blog?
Ryan - The Resume Ninja

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  • Ryan Cordoni

    Hey Everybody!

    Leave me a comment if you have any questions! Seriously, do it!

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