The Hardest Job Interview Questions and How to Answer Them - Honestly Hannah

The Hardest Job Interview Questions and How to Answer Them

I swear nothing causes anxiety quite like a job interview. One of the things that has helped ease my "interview anxiety" is simply becoming educated on the questions that are frequently asked in an interview setting. Most interviewers will ask relatively similar questions, although wording may be altered. Some interview questions are easy, such as "Tell me about your past work experience." This question is pretty straightforward and there's no tricks there. Some questions, however, are really hard to answer because you don't want to accidentally say something that the interviewer doesn't want to hear. So with that, here are some of the hardest interview questions you may get asked and how to answer them!

Tell me about yourself.

This question gives everyone anxiety. What should I tell them? How much should I reveal about myself? I can almost guarantee that you WILL get asked this question in almost every interview. It's a very standard question that sets the pace for the rest of the interview.

Well, don't fret, because there's a few things you can always default to when this question is asked. When you get asked this question. here are some things you could potentially include:

- What college you go to/graduated from
- What you studied/are studying
- Where you're from
- Where you've worked previously
- A few positive personality traits

You don't need to go into your whole life story, just spend a minute (probably no more than 2) helping the interviewer get to know you a little better. The purpose of this question is to get you talking and sharing a bit about yourself.

What are your strengths/weaknesses?

When I first learned the logic behind this question, I was blown away that an interviewer would ask such a thing. What struck me was the fact that the weakness you shared wasn't actually supposed to be a weakness.... I mean, what? It didn't make any sense to me at first, but the more I researched the question, I realized what it seems that interviewers are looking for in this question. 

While, yes, you're supposed to make a "negative" quality seem positive, you can do that in a way that you don't sound generic or fake. The good ol' "I work too hard" or "I'm a perfectionist" sounds way to generic and interviewers have probably heard it a thousand times.

Instead, think of something that you genuinely think is a weakness of yours. Of course, don't say something like "I'm always late." I mean, that just doesn't make you look very good in an interview. Try say something like "Sometimes I struggle with a lot on my plate. To deal with this, I like to organize my priorities to ensure that I don't get overwhelmed." This is a real weakness, but if you said something like this, you would be explaining how you go about dealing with that weakness. 

With this question, the interviewer wants to see you recognize your faults, but also share how you deal with them to ensure success.

As for the strengths part of the question, this one is a little easier. Think about things that you do well, such as "I'm very organized" or "I always work to the best of my ability." Of course, it's good to expand upon these phrases a bit. Share how you're organized and how you believe that would benefit you in the particular position that you're interviewing for. 

Tell me about a time that you've experienced failure and how you dealt with it.

At first, I wasn't really a fan of these behavioral questions because I felt like I was being put on the spot and couldn't always think of a situation that matched the question. As I began to think more about these behavioral interview questions, they started to grow on me. These are actually some of my favorite (and in my opinion, the most effective) types of interview questions. The interviewer basically gets to see what you're like in action. 

You want to think of a specific instance in your professional life or even academic life where you genuinely experienced failure and dealt with it in a positive way.

If you're interviewing for your first internship, a nice go-to answer for this would be a time you were struggling in a class at school. Maybe you didn't do well on an exam, so you altered your study habits or went to see the professor.

How would you fit in with our company?

This can really be a tough one, and to answer this question properly, you NEED to research the company. A lot of companies have mission statements on their "About" page, or even just a few company values listened. If you can refer to anything that you've previously learned about the company, you'll ace this question!

The employee simply wants to know how you see yourself fitting in with the company. Do you values align with the company values? Do you believe your innovative ideas could bring something new to the company?

Why should we choose you?

If you get asked this question, just know that this is your time to set yourself apart from other candidates. What exactly makes you unique for the position? Most employers will interview a number of people for a position, so this is your chance to show them that you're the one they want! 

Highlight some of your best qualities (organization, team player) but also add in something that really does make you unique. For example, if you run a blog, you could say something such as "I've learned a lot about time management while running my own lifestyle blog along with being a full-time student." Obviously, you should expand on this answer to show them even more about you.

Also, this is a great time to again, flaunt your knowledge about the company. You could say something such as "I noticed that your company is committed to quality customer service. Having worked in retail, I have come to believe to high quality customer service is one of the most important aspects of a company. I would be committed to keeping customers satisfied all the time," or something along those lines. 

What questions have stumped you in an interview? Do you have anything to add to these tips?


  1. I stumbled upon this post just in time. I have a job interview tomorrow...added these questions and your tips to my prep list! :) Thanks for sharing.

    paige -

    1. I'm so glad you found this post helpful!:) Hope your interview went well!

  2. This is such a helpful post, its a shame I never saw it before my interview a couple of days a go because this would of been so handy! Love that you've included examples of answers as well
    Charlotte / Charlotte's Picks

  3. Good information to know and right to the point. Thanks for this well written post on search jobs , i’ll follow up for more updates if you keep posting them.

  4. Thanks for the tips. All questions here were asked in my previous job interview, I can say that those are really the hardest if not prepared. Your tips will surely help to ace the questions.


  5. It’s very excellent information and more real facts to provided that post.Thank you for sharing this information.

  6. The things I dread answering are: Tell me about a time you had with a difficult coworker and how you handled it.

    And: Tell me about a time you made a mistake and what you did.

  7. Wow this is so great and insightful. It's the right time to read this since I Will have the interview in 2 days.

    1. Best of luck to you!! Glad you found this helpful :)

  8. great thanks Hannah it really help
    my interview

  9. This was a really helpful and great article ! Excellent job !

  10. Here are a few sample questions you may find yourself struggling to answer, and suggestions to approach them like a seasoned interview pro. : prepare answers for tough interview questions


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