Smart Answers to the Most Difficult Interview Questions

Job interviews are nerve-wracking to say the least, especially when they ask you difficult questions. Here's a guide to help you answer the toughest ones.

This guide was originally posted on 

There are many difficult job interview questions, and your answers could have a significant impact on whether or not you get the job. Here are 12 of the most challenging—and common—questions along with the answers you need to rock your next job interview. 

Can you tell me a little bit about your yourself?

You hear this question and you blanch, because how could you possibly fit your entire life history into 30–60 seconds? Fret not. While this request might seem vague, there are specific things you should keep in mind to help you narrow down what you’re going to say to your interviewer. First, remember this is an opportunity to showcase yourself and tell your interviewer how you fit into the role at hand. You likely have a lot of skills and assets, but remember, you should choose the ones you think will be most useful and relevant to the position you’re interviewing for when answering this particular question. However, keep in mind your interviewer does already have a copy of your résumé, so it’s best to not repeat information that you’ve already provided verbatim.

Related: How to Navigate and Excel at a Job Interview on Zoom 

What do you know about our company?

Before you go for your interview, you need to research the company. During your research process, consider what stands out to you about the company? What makes an impression on you? What made you say, “I want to be a part of that”? This question provides two opportunities:

  • Showing off what you know about the organization by reciting the company’s history
  • Conveying which aspects of the company you identified with and why that makes you a good fit

You’re also getting a chance to show that you’ve done your due diligence by looking into the company. This shows that you care about the position for which you are interviewing.

What is your biggest weakness?

This classic question is asked in almost every interview. It’s hard because there's no easy answer. Interviewers want to see if you can be honest, have a degree of self-awareness, and are compatible with the job. To answer this, let’s first go over a few answers you should never use:

Cop out 

Answers like “I care too much” or “I work too hard” sound ingenuine, and they aren’t real weaknesses.

Inappropriate answers

Saying things like “I tend to steal things” is never good. But if the job is sales related, you also don’t want to say, “I hate talking to people.”

No plan for improvement 

It’s also a bad sign to say you have a weakness without also explaining how you’re working on it. You need to find a real weakness that isn’t critical to the job and explain how you are interested in self-improvement. The best answer will vary between jobs and be dependent on the skills required for the job you are applying for.

Why do you want to work here?

There are a few variations of this question. Whatever you do, don’t mention money. Interviewers want to know what about the company and role appeal to you, the candidate, not just how much money you want to make. Answer this question with either what you like about the company or why the role is important to you.

For the company

  • Mention a good experience you had with one of their products.
  • Explain values or a company culture that you appreciate.
  • Endorse a product they make that you find interesting.

For role-related reasons

  • Express wanting to broaden your skill set.
  • Share how you want to face new challenges.
  • Explain your desire to work with industry leaders you admire (if appropriate).

Related: Top 10 Mistakes New Grads Make When Seeking a Job

What would you want to do if you didn’t have to work?

There are two things an interviewer is trying to determine with this question. First, want to see if you enjoy what you do and aren’t just in it for the money. An excellent answer to this question should include tasks at least somewhat related to your job. Second, they’re looking to learn more about your passions. Your answer doesn’t have to be all about job-related activities (work, education, etc.), but they should be a big part of it. Feel free to include other passions that the interviewer might find interesting.

Why did you leave your last job?

The difficulty of this question will vary widely. If your job was seasonal or part-time, this is easy to answer. But what if you were fired, or if you still have a job? Let’s look at these answers separately.

If you are currently employed…

This is a good situation to be in; it means that another employer values you enough to hire. However, you need a good reason to be looking for a new job, or your new potential employer might get scared that you won’t stay in the position long. Good reasons include looking for a new challenge, moving for personal reasons, and looking to change or pivot your career path. Bad reasons include saying you’re bored, you hate your boss, or that the company won’t last long. Notice a trend between the two types of answers: good answers focus on why the new company would be a better opportunity, while bad answers make it sound like you’re running away to any place that will take you.

If you were fired…

Saying that you just needed a break, took time off for personal reasons, or were laid off (unrelated to performance) are usually fine. But if you were fired, most interviewers will be wary that you might not be a good employee, and you need to change their mind here. There are two good ways to handle this:

  1. Acknowledge a skill deficit and explain how you fixed it or why it’s not as crucial for this job.
  2. Explain how your former company changed that made you not fit in.

Related: What to Do If Your Postgrad Job Plans Don’t Work Out

Why should we hire you?

This question seems so simple that it can quickly catch you off guard if you aren’t prepared. The mistake that most candidates make is merely listing the same skills and experiences that they’ve been talking about for most of the interview. (On the off chance that it’s asked early on, it’s fine to sum up your experience and any unique skills at a high level.) This question is really asking for reassurance. The interviewers want to know they can rely on you. So how do you do that? By emphasizing qualities that are important but aren't necessarily listed on the job description, like punctuality, problem-solving skills, communication ability, reliability, work ethic, passion, and adaptability.

Where do you see yourself five years from now?

To prepare for this question, imagine that you land the role for which you are interviewing. What does the job progression look like? How do you think you will have grown, both personally and professionally, as a result of doing this job? Still not sure? It’s okay to be honest and say that you aren’t sure what the future holds. How much you disclose depends on the position. While most hiring managers are looking for candidates that will stay on for some time, that may not always be the case. If you are interviewing for a training program, the manager may be aware that you’ll be leaving in two years.

Do you have any questions for me?

This is a challenging question because you’ve spent most of the interview focused solely on your own experiences and the role itself. At that point, it can seem like there’s nothing left to ask about. But this is a final chance to connect with the interviewer and leave on a good note. It’s also a good time to show that you care about more than just the role or the money.

Potential questions

  • What are the good and bad parts of working for this company?
  • How is the work-life balance?
  • Can you summarize your experience at the company?
  • What are the best or worst experiences you’ve had so far?
  • What is your management style?

Related: 5 Typical Questions to Prepare With for Your First Job Interview

If you don’t have an answer to an interview question…

Everyone has been asked a question in an interview where they don’t have an immediate answer. Here’s how to address these questions on the fly.

Slow down and don’t rush 

It’s perfectly fine to reiterate a question or say, “That’s a great question, I’ll need to think for a second to answer it.” It shows you don’t panic in situations where you don’t have all the answers.

Demonstrate your thought process 

One of the objectives of an interview is to figure out how you think, so think out loud. That doesn’t mean you have to say everything that flits through your mind. Instead, share the broad contours of your thought.

Connect with a similar question 

Sometimes you can rephrase the question a bit to answer a similar problem. For example, if you were asked about a conflict with a boss but didn’t have one, you could talk about a conflict with a coworker.

Accept temporary defeat 

If you genuinely don’t know something, you’ll have to admit it. But other than saying “I don’t know,” express your curiosity and desire to find the answer later. The most important thing to remember when you run into a question that you can’t answer is not to panic.

Related: How to Master the Before, During, and After of Your First Job Interview 

Before you go ace your next interview, be sure to go over these questions several times until you’re comfortable answering them. Once you are, you'll be much more confident going into your next job interview. Best of luck!

Read the full blog post here, and find more job interview tips in our Internships and Careers section.

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About Katie Horne

Katie Horne is a writer for Most of her time is spent perfecting developer-oriented documentation for a Seattle-based start-up that specializes in identity-as-a-service.


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