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5 of the Toughest Interview Questions Hiring Managers Ask & How to Answer Them

Plenty of people dream of finding a job that they enjoy. But it’s not easy. First, you must find an available role that suits your skills. Then, you must impress recruiters with an amazing resume – lots of candidates turn to trusted resume writers to help build a resume. After all that, you still must survive the interview stage.


For many, the interview is the toughest part of the entire process. It’s often stressful to head into a big interview, knowing that it’s your one and only chance to make a great good impression on a prospective employer. The process is made even more difficult when interviewers ask tricky questions.


This guide will look at five of those difficult interview questions, as well as explaining how to answer them.


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What Is Your Biggest Weakness?

Let’s kick off with one of the most common interview questions. This one comes up a lot, but it still catches many interviewees off-guard. Often, people are so busy focusing on the most positive aspects of their career, qualifications, and skill sets that they struggle to think of any kind of weakness when asked.


However, this is an important question to answer correctly. A lot of interviewers will want to know not just about your skills and positive characteristics, but also about your shortcomings, as well as your willingness to admit to them.


Some interviewees try to evade this question by mentioning characteristics that aren’t really weaknesses, like “I’m too organized” or “I work too hard.” However, it’s best to focus on a genuine weakness and discuss how you’re trying to address it. An example could be, “I am very competitive and want my team to always win by having the best results.”


What Critical Feedback Do You Most Often Receive?

This is another question that comes up a lot and covers similar ground to, “What is your biggest weakness?” Its aim is to find out more about your flaws, but also your ability to take criticism on board and respond it to in a proactive fashion. This lets employers know more about your character – it shows whether you’re willing to listen to feedback and work on yourself, or simply ignore feedback.


Usually, the best way to answer this question is to simply be honest. Think back through your career to pieces of feedback or advice you’ve received from managers and supervisors. Focus on a topic that has been repeatedly brought up and talk about how you’ve responded to that piece of feedback.


An example could be, “I’ve been criticized for sometimes keeping my ideas to myself during team meetings. The reason being, I like to actively listen to others and let everyone contribute their own ideas, sometimes forgetting to share my own. I’m working on this by becoming a more vocal presence and making sure I always contribute in some way before any meeting ends.”


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How Do You Handle Stress?

Sadly, stress is an inevitable part of life for countless people, and work is often the source of it. Over 80% of Americans today suffer from work-related stress, with many admitting that their jobs are the leading cause of stress in their lives.


Given the prevalence of workplace stress, employers need to know how to cope with it. Therefore, they may ask you outright: “Do you tend to get stressed at work?” or “Tell me about a stressful experience at work and how you coped with it.” While the wording may vary, the intent is always similar – they want to know how you respond to stressful situations.


Ideally, they’ll want an honest answer, acknowledging the realities of stress, and your way of coping with it. As such, try to avoid any kind of evasive response, like “I don’t get stressed.” You could, for example, say something like “I get most stressed when I feel a project is beyond my control or I’m unsure about the next steps to take. To remedy this, I’ve found that communication is key. I try to keep in touch and up to date with my colleagues and supervisors to ensure we’re all on the same page and that nobody feels lost or left out.”


What Has Been Your Biggest Failure?

You may be noticing a theme at this point. A lot of the trickiest questions, including this one and all of those mentioned above, tend to focus more on negatives than positives. In an interview situation, you want to be positive and sell yourself, focusing on all the best aspects that make you right for the job. But that can be difficult if interviewers repeatedly ask negative questions.


It’s especially hard if they start to inquire about your “biggest failure.” A similar question could be “Tell me about a time you failed” or “What was your last big failure?” Here, the interviewer wants to find out how you deal with difficult moments and whether you’re capable of learning and bouncing back.


To respond, you first need to think of a failure or challenging situation you encountered. Describe it to the interviewer and explain how the failure came about. Then, immediately turn the question around to focus on what you learned, how you responded, and how you grew from the situation. You could, for instance, talk about the steps you took to prevent the failure from happening again.


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What Can You Bring to This Company?

Here’s another tricky interview question that isn’t as negative as the others above. In fact, this question gives you the chance to shine and show off all your unique selling points and key skills. However, it can be vague and intimidating for some interviewees, and they may not know where to begin.


Ultimately, interviewers ask this question to find out, quite simply, why they should hire you. They want to know what makes you better than other applicants and how you intend to not only succeed in your role, but also improve the company as a whole.


Preparation is key to answering this question. It’s wise to research the company beforehand, learning about its culture, philosophy, and achievements. From there, you can craft a tailored answer to demonstrate how your skills and working mindset make you the ideal fit for the job in question, backing up your answer with examples from your past.


Adopt the Right Mindset to Deal with Tricky Questions

Stress. Weaknesses. Criticisms. Failures. A lot of tricky interview questions force you to bring up the things you’d probably prefer to keep hidden. But that’s the point. Through these questions, interviewers seek to gain a better understanding of not just your plus points, but also your downsides, and how you manage them.


It might seem like they’re trying to catch you out or want to put you under pressure. But, often, they’re just trying to get to know you better. So, opt for honesty in your answers, and always try to frame yourself in the best possible light.


Proper preparation is also valuable when it comes to succeeding in any interview. But If you don’t have too many lined up at present, your resume or LinkedIn profile could be letting you down. You might like to hire a resume coaching service in Denver to help, and make sure to review and revise your resume and cover letter often to impress recruiters.

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