Tough Job Interview Questions (With Answers)

By Chris Kolmar
May. 12, 2021
Articles In Guide

Find a Job You Really Want In

Why should we hire you? That’s the question on every employer’s mind.

When the hiring manager throws you a tough interview question, they’re looking to see if you have a skillset, mindset, and personality that will fit well into the team you’re hoping to join.

This article will help guide you through the process of answering tough interview questions, as well as show example questions and answers that put our advice into action.

Why Interviewers Ask Tough Interview Questions

Hiring managers and recruiters ask tough interview questions to get a better sense of you as a candidate. Standard questions about your qualifications are necessary to learn about your skill levels, but truly tough interview questions are designed to learn more about how you think and work.

For example, an interviewer may ask you how many basketballs you think could fit inside the office space to see how you approach the problem. The “correct” answer isn’t as important as your thought process.

Challenging questions can also separate the candidates into differing levels of cultural fit. Several candidates are likely to have similar skill sets as you, but not everyone will have a personality that gels well with the existing team.

At the most basic level, interviewers employ difficult interview questions because hiring people is expensive, and finding replacements that need to be trained is a real drag on productivity. They want to ensure that you’re comfortable performing all the job’s responsibilities.

For these types of industry or job-specific questions, it’s best to seek out people in your network who have experience interviewing for similar roles. Being prepared for these sorts of questions is the difference between being caught off guard and responding like a seasoned pro.

How to Answer Tough Interview Questions

Tough interview questions are meant to make you a bit uncomfortable. There aren’t any right or wrong answers to them, but there is a winning strategy to responding to these questions.

  • Take your time. Interviewees are often discomfited by moments of silence, but taking a second to consider your response doesn’t make you look stupid — it makes you look like you’re taking the question seriously. There are plenty of strategies to follow when you don’t know the answer to an interview question, but the main thing is to appear calm.

    If you’re caught totally unprepared, you can talk around the question and bring it to a topic you’re more familiar with. Try to avoid flat-out admitting ignorance without lying or deflecting the question too candidly.

  • Think out loud. Your thought process is being assessed more than the accuracy of your answer. The toughest interview questions are typically open-ended, meaning you can answer an infinite amount of ways.

    This strategy works best for brain-teaser type questions, but it can also be helpful when answering hypothetical situational interview questions.

  • Use the STAR method. Some of the trickiest questions you’ll hear are behavioral interview questions. These are questions that ask you about your past behavior on the job to predict how you’d perform in your potential new position.

    STAR stands for Situation, Task, Action, Result, and it’s a great way to organize your answer into a coherent narrative. So when an interviewer poses a question that starts with something like “Tell me about a time” or “Can you give me an example of a time,” that’s your cue to use the STAR method.

    It’s best to prepare a bunch of stories relating to common categories of these questions (challenges, achievements, conflict, etc.) so that you’re able to quickly provide an example on the spot.

  • Tailor your answer. Become extremely familiar with the job description and research the company thoroughly before your interview. That way, you’ll be able to provide answers to the toughest interview questions that align with exactly what the employer is looking for in a candidate.

    For example, if you see the words “collaborate” and “cross-functional teams” in the job description, you should avoid talking about how you prefer working independently. Of course, don’t take this advice too far, or you may end up at a company that doesn’t suit your work style at all.

15 Tough Interview Questions and Answers

Interview questions are like a pop quiz in high school. You have to fire off what you know and hope you passed the exam. It can be a little nerve-wracking. But if you do your homework, you will shine like a star. Here are the most cringeworthy interview questions and how to answer them like a boss.

  1. What is one of your greatest weaknesses? Admit weakness, be self-aware, and take corrective action. (More tips on how to answer “what is your greatest weaknesses”.)

    Example Answer

    I have a hard time delegating. I get so passionate about a project that I want to handle every part of it to make sure it is done right. To help myself with this, I try to match my strengths with where I can best use them in the project. Then I hand off other pieces of the project with better skills for other tasks. I found this keeps me working in my zone of genius. Plus, the project gets done faster.

  2. What tasks do you not like to do? It’s important to be honest here, but provide some context so you don’t sound completely negative.

    Example Answer

    I didn’t like proofreading resumes at my last job. The reason was that I wasn’t very good at it. So I created a resume proofreading checklist. I went over it with my boss to make sure it was complete. Now it’s easy to review resumes and catch the errors I used to miss.

  3. Tell me about the gap in your employment history. This question always makes people uncomfortable, but remember to stay calm. Provide a reason, but also try to mention things you did during your employment gap that kept your skills up-to-date.

    Example Answer

    In the last couple of years, I was home caring for my father, who was diagnosed with Lewy body dementia. During this time, I kept my work skills updated by taking night classes toward my MBA. At this time, my father is in a care facility and I am available to return to work full time.

  4. Tell me about a time when you made a mistake. Shows self-awareness and willingness to improve.

    Example Answer

    I believe we fail forward to success. Each mistake we make offers us a chance to learn. I have learned when a customer asks a question you don’t know, to say that it’s a great question and that you will find out the answer. That way the customer gets the information they need. Plus, you learn something new. Knowing when to ask for help is a key to growth.

  5. Describe a time when your work was criticized and how you handled it. The hiring manager wants to see if you can take coaching and grow from it.

    Example Answer

    Once at my sales job my boss took me aside. She said that when customers asked the prices for common repair jobs that I had to look them up or ask. She challenged me to memorize the pricing of top repairs. So I created a cheat sheet listing the pricing for the top repairs. I taped it on the bottom of my laptop. Having quick access to this information helped me memorize it quickly. The key to sales is knowing your product. This criticism helped me do that.

  6. How do you handle a challenge or conflict you have faced at work ? Show you can keep calm, listen, and resolve the situation.

    Example Answer

    Move to a private place where you can talk. Then I ask them to tell me what is going on. I remain calm and don’t get defensive. I want to make sure that I understand their point of view. Then ask them what I can do to resolve this.

  7. Describe a situation when you took initiative to solve a problem. Interviewers may ask this even if you’re not applying for a leadership position. Employers need problem-solvers at every level of the company.

    Example Answer

    There were a few individuals that came into the store attempting distraction theft. They were unsuccessful and said they were coming back the next day. My boss did nothing to ensure our protection. So I posted the security number by the phone. I spoke with the head of security who pointed extra cameras at our store. I also talked to the head of the police at the location. I wanted to be proactive to support the safety of our store.

  8. Give me an example of a time when you did not meet a client’s expectations. What happened, and how did you resolve the situation?

    Example Answer

    When a dissatisfied customer complained about the quality of one of our jewelry repairs at my prior retail job, I offered to get it repaired again with a rush free of cost. Then I arranged through customer service to give her a free store gift card for the inconvenience.

  9. Give me an example of when you had a disagreement with a co-worker how you handled it. The interviewer wants to know if you have relationship skills and can work well with others.

    Example Answer

    Our company was looking to cut expenses. I found a new vendor that would save us a lot of money. In a meeting, my co-worker brought it up like it was his own idea. I simply said, that’s for spotlighting my point. Then I went on to share all the research I had done regarding the vendor. It was a calm way to reclaim my idea.

  10. Tell me about a time you were under a lot of stress and pressure. This question is designed to learn if you can handle a fast-paced challenging work environment.

    Example Answer

    As a writer, I like the adrenaline rush of a little pressure. When I have a lot of projects on the line, I break it down, set deadlines, focus, and hustle. I stop between breaks to get a drink, walk around, and clear my head. Pressure can be a motivator if you handle it the right way.

  11. Describe a long-term project that you managed and how you kept it moving along. Show the interviewer how you emulate the skills of effective project managers.

    Example Answer

    I thrive on keeping projects running smoothly from kickoff through launch. When I worked at Robbins Inc., a media software and services company, we were tasked with launching new software for public relations and marketing communications professionals. I led the team through lead generation retention, product marketing, and events. We completed the launch in six months. We gained national visibility with influencers and sales skyrocketed.

  12. What is one thing that you disliked about your last job? Tread carefully — this is not the time to trash your boss or bash your co-workers. Tell them tactfully why you are leaving your job.

    Example Answer

    Actually, I loved working at my last job. But the company was very small. I was the only staff member at our Oakbrook office. I missed having coworkers. That’s what excited me about your company. You have a whole marketing team. Plus there is room for advancement down the road.

  13. Why with 15 years of experience, would you be willing to start at an entry-level position?

    Hiring managers worry about hiring overqualified candidates, because they fear you’ll be bored with the duties of the job. Put their anxieties to rest as best you can.

    Example Answer

    While I have extensive writing experience, I really have a passion for writing about job search topics. I love helping others to identify their strengths and land their dream job. Plus, being able to work remotely is a huge bonus.

  14. How much do you expect to get paid in this role? They want to know what your salary requirements are and if they are in their budget. Share a salary range that is fair based on your experience and the market you are working in.

    Example Answer

    With my experience, I would expect to receive something between $75,000 and $85,000.

  15. Where else are you interviewing?

    You don’t need to give any actual names of companies — it’s best to keep your answer to this question slightly vague.

    Example Answer

    I am just starting out in my job search. I am exploring a number of jobs and have applied to a number of opportunities that will allow me to use my skills in marketing and publicity. I’m really excited to learn more about seeing how I can contribute to your company.

Tough Job Interview Question Tips

Erica Kosa
Career Coach and Resume Writer

When an employer asks the dreaded weakness question, the hiring manager is trying to find out if there are any holes in your experience that would keep you from doing the job. Look over the job description carefully before your interview and make sure you don’t pick a weakness that might be relevant to that particular job. For example, if you are applying for a project management related role, you don’t want to say that your biggest weakness is lack of experience with budgeting or time management. Instead focus on a skill that is less likely to be used for that position so you don’t accidentally scare off the employer. This might seem like a no-brainer, but you’d be surprised at how many candidates shoot themselves in the foot with this question without realizing it.

Additional Tips to Prepare for Your Job Interview

Remember confidence gets you hired.

When you feel relaxed, you will give better answers. So you want to do everything to feel your best:

  • Research the company and role.

  • Do a mock interview with a friend.

  • Get a good night’s sleep.

  • Dress sharp.

  • Have a good meal beforehand.

  • Know what to bring to an interview.

  • Arrive early.

  • Put on your best smile.

  • Sit up in your chair.

  • Make eye contact with your interviewer.

  • Project your voice.

  • Don’t shrink down in your chair and mumble out of stress.

Tough Job Interview Questions

Denise M. Bitler
Owner/Certified Resume Writer/Interview Preparation Specialist/Career Coach, Resume-Interview Success, LLC
Resume Interviews Success

“Tell me about yourself” is one of the most common interview questions, yet it is the one that most candidates do not answer effectively. They either provide too little or too much or they provide information that doesn’t speak to their “brand” or does not relate to the position they are interviewing for. Your answer to this question should be between 1 to 3 minutes, should be tailored to the role and company you are interviewing with, should use a Past, Present, Future format, and should include proven successes and strengths that relate to the job you are apply to. Be passionate in your response but keep it professional. Lastly, practice but don’t memorize your response. This question is usually asked at the beginning of the interview so it is your chance to stand out from other interviewees and set the tone for the remainder of the interview.

Final Thoughts

Take a breath.

You can harness that stressful energy to give yourself the edge. Now you can tackle even the trickiest questions that recruiters ask with ease.

Tough Job Interview Questions

Aaliyah Paul
Owner of Resume Queen LLC/ Resume Expert

I say the most important tip in job search is confidence. You can do all of the research on the position and the company. But if you lack confidence with your delivery in the interview it will be difficult to land the job that you want!

A lot of the times it is how you say things with less of a focus on what you say.

You could have best resume which why you got the interview, but in your interview you have to be able to support what is stated in your resume.

I always recommend using the STAR Method in interviews

S (Specific Situation)

T (Task)

A (Action)

R (Result)

You can use this method for just about any question that is asked in a interview. Develop a few stories with analysis in mind and have them prepped and polished for your interview.

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Chris Kolmar

Chris Kolmar is a co-founder of Zippia and the editor-in-chief of the Zippia career advice blog. He has hired over 50 people in his career, been hired five times, and wants to help you land your next job. His research has been featured on the New York Times, Thrillist, VOX, The Atlantic, and a host of local news. More recently, he's been quoted on USA Today, BusinessInsider, and CNBC.

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