Tough Job Interview Questions You Should ALWAYS Be Prepared to Answer

Tough Job Interview Questions You Should Always Be Prepared to Answer

Job interviews can be tough.  Often times, you can never be too sure of what to expect.  Who will interview you, what type of questions will they ask, will they like me?  There are many variables at play during the interview process and that can make anyone a bit nervous.

But despite the unpredictable, we can still do our best to prepare diligently for an interview.  One especially tricky area some preparation can help us navigate is those exceptionally tough questions that will inevitably come up during the interview.  These are questions like, “What is your biggest weakness?”, “Tell us about an interpersonal conflict you had at work and how did you resolve it?”, and “Have you ever been fired?”.

Tackling Tough Job Interview Questions

Tough job interview questions like these are difficult for several reasons.  It’s easy for the answers to be misinterpreted by employers, or to accidentally say something you may regret later.  This is especially true because the answers to these questions often provide deep insight into a job candidate’s character, personality, work ethic, perspective, etc.  Seemingly innocent responses to these questions can indicate that in actuality, the candidate is a jerk, or lazy/unmotivated, or close-minded/change-resistant, or any other manner of negative qualities.

This is why employers ask these questions.  They are looking for clues hidden in an answer that reveals a candidate’s truer self.  Every employer knows that job candidates are likely trying to answer every question as positively as possible, potentially even putting on a darn good act in hopes of getting hired.  The tough questions, however, are meant to potentially throw people off their game and it usually forces more honest answers, answers that are harder to sugarcoat with a positive spin.

And this is where the preparation comes in.  The best way to tackle the tough job interview questions is to prepare in advance for them.  If you anticipate them being asked, you have time to prepare excellent answers to them.  You eliminate the possibility of giving answers you regret and minimize the chances your answers will be misinterpreted in a way that reflects poorly on you.  Employers are bound to be impressed, especially since they are usually accustomed to listening to people fumble their way to an answer or shoot themselves in the foot.

The best part about this is that most employers use the same few “tough job interview questions” regardless of the company, the industry, or any other factor.  Do enough interviews and you’re very likely to hear the same questions over and over again, all with the goal of learning more about the real you.

So no more rambling on, here are some of those tough interview questions you’re likely to be asked, why they are asked, and how best to answer them.  Prepare your answers in advance, and you’ll be a job interview pro in no time!

Tough Job Interview Questions & How to Answer Them

Question #1 – What Is Your Biggest Weakness?

Why Employers Ask It:  Employers ask this question in hopes that job candidates will open up like a book and start disclosing every potential poor quality they possess.  Much to the employer’s delight, this is exactly what most people do.  Since it works most of the time, it’s a pretty common question and it can save an employer lots of time and energy determining if a candidate is the right fit.  Even when a job candidate has a thoughtful answer to this, it still gives great insight into the level of self-reflection and thoughtfulness a candidate might possess.

How To Best Answer It:  There are two ideal ways to answer this question.  The first way involves answering with a quality or trait that is not typically considered to be negative.  Pick something that is considered to be fairly neutral, discuss the impact it has had on you, and then explain the lessons you’ve learned from it.  You might say your weakness is that you’re a perfectionist, have high expectations for your performance, or tend to be overly ambitious.  You do want to have some answer ready for how it impacted you and what you’ve done to improve, but starting with a fairly neutral quality gives you a strong position when answering this question.

The other way to answer this question involves disclosing a bonafide weakness, but then giving specific examples of how you learned from that experience and all the ways you are continuing to foster positive growth.  This is my preferred way to answer this question.  It exhibits a person’s ability to look at themselves openly and critically but also find tangible avenues for growth and development.  It’s the idea of taking a weakness and turning it into a positive.

You might say you used to struggle with meeting deadlines but have started the practice of creating specific tools for yourself that organize your tasks and keep you on track.  You might say you’ve struggled with speaking publicly but have since been doing Toastmaster’s classes which have significantly helped your speaking skills.  Giving the specific examples, and strong ones, is critical here, but this is a great way to answer this tough interview question.

And no… “I have no weaknesses” is NOT a good answer.

Question #2 – What Do You Know About Our Company?

Why Employers Ask It:  Employers want to hire someone who actually knows something about them and what they do.  It’s always a good thing to be a bit more connected to the company than just being there “for a job”.  This question is also used to see what preparation a candidate has done before an interview, a potential sign of the preparation they will have for their tasks in the workplace.

How To Best Answer It:  This question is not as much hard as it is unexpected.  Imagine how embarrassing it would be to not know what the company does if asked.  “Umm, I don’t know what your company does, I just saw you were hiring for a ________ position”.   Not having an answer here looks horrible, but with just a little preparation beforehand, you can look like a superstar by giving a brief rundown of the company and their business.  In today’s age with the internet, it’s easy.  Most companies have websites.  Go check out their about page for the scoop.  If the company doesn’t have a website, you should still be able to dig up the basic info fairly easily.  Make sure to add this to your preparation routine for interviews and you’ll be in good shape!

Question #3 – Why Do You Want to Work for Our Company?

Why Employers Ask It:  Similar to the last question, employers often are interested in hiring candidates who have a deeper connection with their company.  If an employee is connected to the company’s brand, services, or mission, it can potentially indicate a happier and more productive employee.  At the very least, it should foster higher morale amongst employees and a sense of fulfillment within them.  Employers use this question to see if this is just another job for you, or if there is perhaps something a bit more behind the scenes of why this is the right job for you.

How To Best Answer It:  The goal with your answer to this question is trying to make that deeper connection with the company’s brand, services, or mission.  What about the company or role resonates with you?  Are you particularly passionate about the work this role involved?  What about the reach or social good a company does, or the certain populations they serve?  Expressing interest in the company’s mission and your connection to that can be a solid answer here.  Answers about monetary gain or “it’s a job” will likely not impress.  It’s not always a deal-breaker if you don’t have that strong connection to the company, but someone who knows about the company and has a reason for wanting to be there will certainly gain an edge in the hiring process.

Question #4 – Why Did You Leave Your Last Job?

Why Employers Ask It:  This is a great question for employers to ask because it can often get candidates to open up like a can of worms with answers that provide insight into their personality, their strengths and weaknesses, and the things they are motivated or driven by. Emotions also sometimes run wild and candidates may discuss a lot more than they might have preferred to say.  It can especially be a telling question if someone had been fired or left a prior job on bad terms to see how they handle their response to that.

The key goal with this question, though, is to get an idea of how a job candidate may fit in the company and role they are applying to based on factors for why they left (or are leaving) their last (current) position. If the employer happens to have qualities similar to the ones a candidate expresses they were dissatisfied with, the employer will likely opt to not move that candidate further through the interview process.  Likewise, if they are unable to provide the satisfiers a candidate seems to be motivated by (money, success, power, culture, etc.), they may also decide to move away from hiring that candidate.

How To Best Answer It:  This can be one of the toughest interview questions because there are so many ways to shoot yourself in the foot with your answers.  Even good intentions or valid reasons to leave a prior or current job can be easily misinterpreted in the wrong way by the employer.  Imagine you said you left a prior job because of over-time and working 60 hour weeks.  If the employer you’re interviewing with happens to have even slight over-time, say 45 hours a week, they may be hesitant to hire you since they know over-time is a dissatisfier.  They may not take the time to differentiate between 45 hours and 60 hours, when in reality 45 hours might have been perfectly fine for you.

This question ultimately requires the most preparation out of any.  First and foremost, the most important requirement to answering this question is to keep emotions in check.  It is very easy here to rag on bad leadership, awful co-workers, ridiculous processes or policies, or any of those other factors that are far too easy to rant about.  It’s important to stay positive, professional, and poised, so you don’t come across as a complainer, a loose cannon, pessimistic, or negative.

The second important requirement for answering this question is thinking about what qualities the employer has and if anything you might say would raise a red flag to them.  If you do start to describe reasons why you left your last job, is there a chance that this new employer also actually has some of those qualities as well?  That would not be good.   You also need to be careful of how things can potentially be misinterpreted.

In this regard, choosing a neutral and “safe” answer is often the best choice in most cases.  Employers do it all the time when letting employees go, “It wasn’t the right fit”.  I recommend you keep it simple and do the same in interviews.  Simply tell them it wasn’t the right fit for you and that you feel this current role will be a much better fit (and the reasons why).

Question #5 – Where Do You See Yourself in 5 Years?

Why Employers Ask It:  The details and goals within a five-year plan can gauge a candidate’s ambitions, career goals, and vision for the future.  It also can help determine if an individual is driven towards moving up the career ladder or is perhaps more content staying at their current level.  This question may also be used to determine if the position being applied to aligns with the candidate’s goals.  An employer may be wary to hire someone if it appears the position they applied to is disconnected from their goals for the future.  They may fear a quick turnover, or an unmotivated and low performing employee if the position doesn’t necessarily lead to the opportunity the candidate is looking for.

How To Best Answer It:  The tricky part of this question is trying to figure out what the company is looking for in the position they are hiring.  Are they looking for someone who they want to move up the career ladder quickly, or do they want someone that will be content in the same role for years and years to come?  Expressing goals that go against what the company is looking can often be one of the quickest ways to take you out of the running for the job.  It’s not uncommon to hear stories about people who described goals to move up the career ladder, but the company then decided to not hire them because they didn’t want them to be disappointed when the company had no intention of ever promoting the person in that role.

In this sense, the best approach here requires a bit of “gaming” the interview process.  Essentially answer whatever is most favorable to the employer!  If you sense that they want someone who will stay in the same role for a long time, express that your five-year plan involves the position you’re applying for and finding ways to improve at your role as you grow more experienced in it.  If you sense the company wants someone who can take more responsibility quickly and be moved up the career ladder, then express this ambition to take more responsibility and move up within the company.

Honestly, this question is kind of a silly one, especially when employers make the association between a person’s goals and the current role.  A lot can change in five years.  A person who never thought they wanted to be promoted may actually love it, and vice versa.  A person’s goals may also not have any correlation at all with their ability to perform in the role.  Ultimately, It is a bummer if a company writes you off for a job because of your goals for the future, so the best answer here is choosing the one the company wants to hear.

Question #6 – Describe a Time When You Demonstrated _________ (Skill, Qualification, Etc.)

Why Employers Ask It:  This is the moment when employers want to see if you REALLY know the stuff you listed on your resume.  Do you actually know what you claim you do?  Employers will generally ask you to describe a SPECIFIC example of a time you demonstrated one of the skills or qualifications they are looking for in the job.  Vague answers will simply not do.  Employers are looking for detailed accounts of times you’ve tangibly demonstrated the skill or qualification in question.

How To Best Answer It:  The main challenge with this question is being able to quickly think of those specific examples where you demonstrated the skills and qualifications that are relevant to the job.  The best approach here is reviewing all the main skills and qualifications requested for the job you’re applying to and then thinking of specific examples of how you demonstrated those.  The more details and the more specific you can be, the better.  Employers want to hear about real scenarios that occurred that show you know your stuff.  Prepare your answers in advance, and you should be good to go regardless of what skill is asked about.

Question #7 – How Would You Resolve an Interpersonal Conflict with a Co-Worker?

Why Employers Ask It:  Employers use this question to get an idea of how someone would potentially handle the inevitable conflicts that often come up with co-workers in the workplace.  Not everyone always gets along, but there is an expectation that everyone is professional and that they find ways to resolve conflict in an appropriate manner.   The answers given to this question can often show a lot about a job candidate’s temperament, social behavior, and conflict management skills.  It can help determine if the candidate will work through conflict in the way the company finds most appropriate for its company culture.

How To Best Answer It:  It’s most important here that you present yourself as someone cool, calm, and collected when it comes to handling conflict or disagreements, especially interpersonal ones.  It’s almost inevitable that co-workers may have a conflict at some point, so explaining that you can handle this in a professional way will earn you a big thumbs up from potential employers.  The best answers here are responses that involve communication, respect for others, and the willingness to compromise and find solutions.  Lashing out, teaching people a lesson, or other rash responses are not the answer here!  Instead, good answers might mean discussing the problem with the co-worker and working to find solutions, or moving it up the chain of command for resolution.  There can be various good answers, the key is just avoiding the ones that make you look hot-headed or rash with your actions.

Question #8 – If You Disagreed With Your Boss, How Would You Handle It?

Why Employers Ask It:  Employers want to know how you might handle disagreements with your managers or leaders.  Are you someone who always does what is asked or are you open to voicing your opinion about things you disagree on?  What if a boss or manager is doing something unethical or illegal?  How would you handle that situation?  This question is another one that is used to measure someone’s conflict management skills but also provides clues on how they function in a structured hierarchy with a clear chain of command and authority figures.  It can also provide insight into whether a candidate is more of a leader or a follower, with employers favoring whichever suits their preference more for the particular role.

How To Best Answer It:  This is definitely a tough question and one that can definitely cause some panic.  More so if you’ve ever had bosses that have… not been the best (to put it nicely).  It can get even trickier when you consider some companies might prefer employees who are more keen about voicing their opinions while other companies may want employees who just always do what is asked.  At the end of the day, I feel that finding a happy middle-ground with your response is the best approach.  You should try to stay as true to your normal approach to this as possible, but also focus on answers that exhibit professionalism and respect for authority.  Show that you’re not a complete pushover but also that you’re someone who can use proper communication and grace when disagreeing with an authority figure.  This type of response is safest and is also one that will go over well with employers.

Question #9 – What Do You Feel You Should Be Paid?

Why Employers Ask It:  Employers sometimes may ask in interviews what you’re hoping to be paid in this role.  This question is often used to gauge if the level of compensation offered by the employer matches what the candidate is looking for.  If a candidate wants $80,000 but the employer is only paying $60,000, that may be cause for not moving further in the interview process with the candidate.  This question can also be used to get a feel for how a candidate personally values their skills and experience and how in touch they are with what the market is actually paying for the role they applied to.

How To Best Answer It:  First off… salary or money questions are BAD FORM in interviews.  I feel strongly that these questions should always be reserved until a company is ready to make an offer and then negotiations can take place if necessary.  Regardless of my opinion, that won’t stop employers from asking candidates about their salary expectations in interviews.  Therefore, great answers to this question are ones that don’t specifically list a salary requirement but keep the matter up for discussion at a later time.

One great response is, “I’m looking for a competitive wage based on industry standards and current market value for this type of role.”  This is a safe answer that is professional and will help move you forward in the interview process.  If a company continues to press for an answer involving more specific numbers, I would still not disclose a number and just let the employer know that you would prefer to have an offer presented before negotiating salary.

Question #10 – What is Your Process for Completing a Difficult Task?

Why Employers Ask It:  Employers ask this question to get an idea of you might approach a challenging task or difficult problem.  Is your process reasonable?  Would the company’s processes or policies support your process or hinder it?  Do you even know how you go about your work?  The answer to this question always requires a good level of self-awareness and the ability to self-analyze workflow.  Being able to break down your processes or workflow into a tangible order of operations can help build confidence in an employer to hire someone.  Good answers here can also demonstrate excellent problem-solving skills, or strengths a candidate may have that can benefit the employer and their operations.

How To Best Answer It:  There’s no one correct way of answering this, the best approach is simply understanding how you do work.  Take time to think about your typical approach to work and make sure you understand the thought processes and steps you take to get the job well done.  Some people are more prone to jump straight in while others opt to plan and prepare in advance.  Others may find themselves using more organizational tools like spreadsheets or lists, while others may have great mental memory and retention of details.  Once again, it’s not the exact answer here that is important.  It’s that you have the ability to self analyze your process for work and are able to explain that in an understandable way to employers.

Question #11 – What Is Your Greatest Achievement?

Why Employers Ask It:  This question is often asked out of plain old curiosity.  There’s no particular hook here that makes asking this question more or less beneficial to employers, but employers can use it to help get a feel for a candidate.  The answers given here might reflect on a candidate’s professional capabilities, personal endeavors, and provide insight on their perspective of achievement and value.  It can also provide clues about their ambition and potential for achievement, and it highlights qualities (both good or bad) that are part of the achievement they describe.  In a roundabout way, It helps the employer answer the question of who is this person and what matters to them?

How To Best Answer It:  The most important factor when answering this question is understanding that your answer DOES NOT have to be work-related!  I mean, it can be a work-related achievement but I often find the more powerful answers here to be personal achievements.  Personal achievements are especially strong answers when they also highlight a lot of high quality skills and personal growth and development.  For example, my go-to answer was always that I completed my college degree online while also working full-time and raising my newborn child.  I describe how it was really quite challenging, but I was determined to make it happen to better myself and my future.  Employers have always resonated well with this!

Another person might describe how being a good parent has been their greatest achievement, or that time they lost a significant amount of weight, or worked hard for a certain contest and won.  As I mentioned, the big work-related achievements work here as well, but don’t hesitate to use a personal achievement if it really highlights some of your greatest qualities.  That’s ultimately the key to how to best answer this question.  Pick an achievement that highlights your strengths and most desirable qualities!

Question #12 – How Do You Handle Stress at Work?

Why Employers Ask It: Stress is a fairly natural occurrence in most parts of life.  Even the best jobs will have their share of stressors.  While stress itself is a constant, not all people handle stress the same way.  Some flourish in stressful situations while others completely panic.  Employers ask this question to see just how a candidate might handle a stressful situation at work.  Maybe it’s a high profile project or an unexpected but pertinent deadline to meet. Are they able to keep above it and still accomplish great results, or do they drown in it and fail to perform?  Do they help others through stressful situations or do they draw others into a pit of chronic complaining and low morale?  The answer given to this question allows employers to see how someone fits in with the stress level of the job, the expectations of the company, and the company’s culture.

How To Best Answer It:  When an employer asks about how you handle stress at work, some people assume that means the job is stressful and maybe they don’t want it after all.  In most cases, that is not the case.  As mentioned above, stress is a fairly natural occurrence in all facets of life, including work.  The best answers here always focus on positivity and a healthy relationship with stress.  The ideal answer is neither flourishing in stress or drowning in it, but rather existing peacefully with it.  This may all sound a bit philosophical, so just remember that your answer should not express fear, doubt, or hesitation about how you handle stress, but instead express that you take your work and responsibilities seriously and will always find efficient ways to complete the work needed during a stressful time.

Question #13 – Tell Us Why We Should Hire You for This Job

Why Employers Ask It:  Often a closing question from employers, this is the question that gives the candidate their chance to make one last big pitch for why they should get the job.  Employers are looking for a rousing closer that highlights all the reasons why the candidate is the right person for the role.  Can a candidate articulate their response well and make a strong connection between their strengths and abilities and the requirements of the job?  Employers are ultimately looking for a convincing response that gives them a lasting positive impression.

How To Best Answer It:  This is one last chance to make your big pitch.  It’s even more important because your answer may be the thing employers most remember about you since this is often the last question asked.  Craft your response to draw connections between the requirements of the job and your skills and experiences.  If you’re connected with the company’s mission, brand, or services, be sure to highlight that.  Be confident and positive with your response.  As always, provide tangible responses and specific examples that support your statement.  Employers want to be sold on why you’re the best person for the job, give them a response that wins them over!

General Strategies for Tough Job Interview Questions

Above we discussed some of the most common difficult interview questions you may hear, but that certainly doesn’t cover all of them.  There is any number of various tough job interview questions you may be asked to answer during an interview.  To best prepare for these, here are some general tips that will help you tackle even the most unexpected interview questions.

Be Prepared

This whole post is about being prepared, but how do you prepare if you don’t know what the question will be?  This is where some additional research comes in prior to the interview.  It’s easy these days to use sites like LinkedIn or Glassdoor to find information about what questions employers may ask during an interview.  Glassdoor, in particular, is great for this as they have a whole section dedicated to potential interview questions for each individual company.  LinkedIn can come in handy by reaching out to connections who work at that company to see if they can share information about how interviews typically go.  A little research like this can go a long way in anticipating what a company may ask during the interview.

Be Positive

A key tenant throughout all these tough job interview questions is maintaining positivity.  It’s risky to come across as negative, close-minded, angry, or frustrated.  It’s important when answering the tough interview questions that you’re being mindful of word choice and tone.  If you anticipate something being potentially misinterpreted or coming across as negative, I would avoid saying that at all.  If in doubt, just choose a neutral or “safe” answer that has little chance of being misinterpreted in the wrong way.  Positive body language also goes a long way.  Firm handshakes, good posture, a smile and happy expression.  These techniques will all help you maintain the positivity employers want to see.

Be Poised

This tip is all about keeping your cool.  It’s easy to get flustered when presented with a tough question you weren’t expecting.  Most people want to fill the awkward voice of silence as quickly as possible and this often results in poorly phrased and rambling responses that most people later regret.  It’s important to understand that it’s OK to slow down during an interview and that taking a brief pause before answering a question is both acceptable and ideal.  Tell the employer, “give me a little bit to think about this”, then take about 10-20 seconds to really think through the options of how to best answer the question.  I don’t recommend you take more than 30 seconds, but a lot of great decision making on how to best answer can occur in that small 10-20 second period.  This allows you to give an answer you’re really happy with instead of one you later regret.

Use Specific Examples When Appropriate

Always try to use specific examples when answering interview questions.  Sometimes it may not be possible to avoid generalizing or giving more vague answers, but if you can provide a specific example to back up an answer to a question, do so.  Giving an example helps to validate and strengthen your responses.

Wrap up

I’m hoping that this article will help you tackle the tough job interview questions next time you find yourself asked these in an interview.  The more interviews you do, the more you’ll see that many of these questions come up time and time again.  By preparing how to answer these questions in advance, you’ll help ensure you’re always ready to knock your job interview out of the park and increase your chances of getting the job.

Are there any specific tough job interview questions I missed?  Let me know your thoughts in the comments below!

Yours Truly,
– Mr. Happy Work

Looking for more job interview advice and articles?  Check out the “Job Interview Tips” Page!

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