5 Difficult Job Interview Questions and How to Answer Them



Remember the first interview you had for a job that you really wanted? I remember mine. Hopefully you were more prepared than I was. I stuttered, rambled and was caught off guard by almost every question. Needless to say, I didn’t get the job.

Luckily, that was quite a few years ago. Since then, my interview skills have improved immensely, thank gosh! (I’m sure Intel wouldn’t have even considered taking me on if my interviewing skills hadn’t improved.)  I still get nervous, and I still ramble sometimes, but I’ve learned to control my bad habits by going into interviews prepared. Contrary to what some people believe, you ABSOLUTELY CAN prepare for interviews. And doing so isn’t cheating. In fact, I’ve learned that employers actually appreciate preparation because it shows that you care about the job and that you think before speak.

If you haven’t already noticed, there are many standard interview questions that you’re likely to get asked no matter where you’re interviewing. Determining how you’re going to answer these questions ahead of time can make all the difference. (Google “common interview questions” and you’ll see what I mean.)

But sometimes, knowing the questions ahead of time isn’t enough. Sometimes, future employers are speaking to you in code. What’s really helpful is to know what employers are really looking for when they ask you the difficult questions.

Difficult Question #1: “Tell me about yourself.”

This is more of a demand than a question, but you get the point. As much as it may sound like it, this question isn’t asking you to tell your life story. Your future employer doesn’t care how many brothers and sisters you have or that you used to be a gymnast in high school (if you really want your employer to know you’re a gymnast, put it under “interests” on your resume). What your employer is really asking for is your “Elevator Pitch.” An “Elevator Pitch” is a concise, carefully planned and well-practiced description about yourself and your skills that you could give in the time it would take to ride an elevator. Use your elevator pitch to speak to your strengths and accomplishments that you think your employer will be interested in. After you’ve come up with your pitch, practice it. For help with developing your personal elevator pitch, check out WikiHow’s article.

Difficult Question #2: “What are your strengths?”

This is easy – what are you good at? But your employer wants you to be specific, not generic. And give examples. Instead of saying “I’m a hard worker,” say “one of my strengths is that I’m a go-getter. I’m always thinking of how I can contribute to the company. For example, when I worked at (insert past job here), I (insert example here).” Before your interview, think of at least two strengths and specific examples to back them up that you can tell your potential employer about.

Difficult Question #3: What are your biggest weaknesses?

This is a loaded question. There are a lot of ways to answer this question and I’ve heard many opinions on the best ways to do it. I’m going to give you my opinion: Be honest. Don’t make up some bullshit about how you’re just “such a perfectionist” and “have to make everything perfect” if it’s just not true. (Plus, I think employers are sick of hearing that answer).

Instead, recognize the fact that everyone has real weaknesses (even you). But the best employees don’t let their weaknesses get in the way of their work. So, if you’re asked a question like this, tell your future employer about a weakness that you have, and how you’re working to overcome it. (But choose a weakness that isn’t extremely personal or inappropriate, obviously.) Your honesty should impress your employer, and the fact that you’re taking initiative to overcome your flaws is also admirable.

For example, my answer to this question is that I’m not a very strong speller. (I’m actually TERRIBLE, but I don’t go to that extreme when I’m talking to my interviewer.) But I know this about myself so I always carry a dictionary with me so that I can look things up. I also used to tutor grammar, so I’m very conscious of the fact that some words may sound similar but have different spellings (e.g. “further” vs. “farther,” “affect” vs. “effect,” “principle” vs. “principal”) so it’s not difficult for me to catch mistakes. I’m also very careful to proofread all of my writing.

Difficult Question #4: Why do you want to work for this company?

I can almost guarantee you that you’re going to be asked this. Your answer to this question is another good time to be really specific. The best way to be specific here is to do your homework before the interview. Research the company. You should be able to find at least five specific reasons you want to work for the company. If not, then maybe you shouldn’t be interviewing with them.

In the case of an interview at a PR or ad agency, don’t just research the agency. Research the clients you’re going to be working with. If you’re interviewing for a position on the healthcare team, talk about why you’re passionate about healthcare. If you’re interviewing for the tech team, talk specifically about why you’re excited about the tech clients. If you don’t know what team you’re interviewing to be on, check out the list of clients on the agency’s website so you can get an idea of the types of clients you could be working with.

Difficult Question #5: Do you have any questions for me?

This question is usually at the end of the interview and it’s a very important one. I think that every employer will agree that the worst response you can give here is “no.”  Always, always ask questions when you’re asked if you have any. If you don’t, you’ll look like you’re not interested in the company or the person you’re talking to (and you’ll also look a little silly). Thinking of questions really shouldn’t be that hard though. You’re at a new company and interviewing for a new position, so you’ve got to have something you’re curious about! Think of at least 3-5 questions before the interview so you aren’t caught off guard when you’re asked if you have any. And don’t be afraid to write them down on a piece of paper that you bring into the interview (preferably a pad of paper, because it looks more professional). That way, you can take notes on the pad while the interview happens and add questions to your list as you go on. Often, interviews turn into conversations, not just Q&A sessions, and your asking questions is a good way for you to get a feel for the company.

But if you’re really having trouble with this one, check out this guide to coming up with good questions for an interviewer.


These are only a few examples of difficult questions you’ll probably get asked in your next interview (and every interview after it). For more examples of how to answer difficult job interview questions, check out “The 24 most difficult questions you’ll be asked on an interview.”

Ps. Ready for some more interview tips? Check out “How to Dress for an Interview.”

12 Responses to “5 Difficult Job Interview Questions and How to Answer Them”

  1. 1 Margaux

    Have you ever written a post on writing your own letter of recommendation? I was just asked to do that by my former supervisor and I’d love any advice.

    On a related note, have you thought about having a widget in the sidebar so readers could search your entries for keywords? :)

  2. Margaux,

    I haven’t written about writing my own letter of reccomendation, simply because I haven’t had to do it yet. My best advice would be to speak about what you’ve done and your skills as honestly as possible, using clear examples. You can probably come up with more examples than your manager anyway. Then, make sure you run the final copy by your manager and ask your manager if he/she has anything to add.

    And in response to your second questions, that’s a great idea! I’ll look into it. I also need to add a “tweet this” widget, which I haven’t gotten around to doing.

    Hope this was somewhat helpful!


  3. Just added a “search” widget to the right side of my blog!

  4. 4 wei2

    Research the clients you’re going to be working with instead of just researching the agency is a great advice.
    Thanks Sarah!

  5. 5 Ashlea

    I completely agree….it’s a great idea to research the clients. I absolutely despise answering the question “Tell me a little about yourself.” I don’t think I’ll ever be prepared for that one!

  6. Great post- very useful information that will come in handy for everyone. The 24 most difficult q’s is a great starting point when preparing for any interview.

  7. 7 pdxsx

    Great post, Sarah! Very useful for new college graduates!


  8. You’re right, the “tell me about yourself” demand can be pretty daunting… I’m going to have to work on that one before week 10.

  9. 9 Rachel

    Very helpful post, seeing as I have an interview in a few days. I really love your blog and I’m adding it to my favorites right now!

  1. 1 How to Dress for an Interview « The Confessions of a PR Gal
  2. 2 How to Dress for a Job Interview « The Confessions of a Product Junkie
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