The 12 Toughest Interview Questions (And How To Best Answer Them)

July 28, 2022 by

Acing a job interview often depends on great preparation for all types of questions, especially awkward or inappropriate ones about your family, personal lifestyle, current salary, and other off-color subjects.  

Despite the great effort by most employers to promote Diversity & Inclusion (D&I), inclusiveness, and bias elimination, some inappropriate queries can arise during recruitment.  As such, I thought it would be helpful to you, your managers, and your team members to have an outline of some of the worst or toughest interview questions, as well as how best to answer them.


Question #1.  What is your salary in your current job?

(It is also worth noting that asking a job candidate for their current salary is illegal in certain cities and states, and yet, that does not mean certain hiring managers won’t ask).

Answer:  “For several reasons, I do not feel comfortable answering that.”  Then, take the pay conversation in another direction by telling them what you expect to earn in the position for which you are interviewing.


“I know that my employer conducted regular salary surveys which benchmark the salaries paid by other area employers for the same positions.  So I’m pretty sure that I am being paid at, or above, market.  This salary survey information is public and I’m sure your HR department knows how to access it.”


Question #2:  What did you like least about working at your last employer?

Answer:  The best responses will tactfully turn this around on the interviewer by making it sound like the negative is actually a positive about the job!!!

For example, start by saying “Well actually, there are so many positive things to say about my last employer, however if I were to highlight one area . . . I used to regular see processing inefficiencies and operational miscues.  So, I would regularly suggest solutions for these opportunities for improvement which would have saved a lot of time and money, but it never seemed like these ideas were ever adequately considered, which was a bit frustrating.”


“I’d always try to go out of my way to ensure that all of our customers were treated fairly and honestly, and yet, I used to see situations where the company’s stated fairness and equity policies were not followed.  As such, at times staff members were not treating our customers the way they should have been treated.  


Question #3.  “Please tell me about your children and how they might or might not affect your work.”

Answer:  “You know what?  I’d really like to focus on my skill sets and abilities that will make me successful in this job.  I have made it a point to keep family and work life separate, and its actually worked out really well.”


Question #4:  What is your typical work week in terms of the number of work hours?

Answer:  “Whatever it takes to get the job done.  I also don’t mind working late or on weekends in order to accomplish the tasks at hand and meet deadlines.”

(Be careful not to have the conversation make the interviewer wonder if you work long hours because you are inefficient).


Question #5:  I see from reviewing your resume that you have never actually worked in a position like this one.  How will you manage?

Answer:  Recognize that this reality is an obvious weakness.  Rather than ignoring it, know that weakness means risk to an employer, and as such, they are looking for reassurance that you can adapt to both the new position and its responsibilities.

For example, highlight previous occasions in your job where you were moved to different departments or roles which required you to quickly and successfully learn and use new technology.  Give specific examples.

Try to broaden your answer by saying “We are all faced with quickly moving and changing environments which consistently present new challenges.  I have always been able to excel in such circumstances and perform well in those situations, despite tight deadlines and little support.  In fact, I actually welcome and get excited about those challenges.”

Importantly, go on to provide specific examples of where you successfully demonstrated these skills.  This expansion will effectively close the issue in the interviewer’s mind and paint a positive picture of your strong adaptability.


Question #6.  What have you learned the most from your career thus far?

Answer:  This is a very open-ended question which allows you to emphasize your positive traits and accomplishments.

“I have enjoyed learning many things as you can imagine.  But for me, there is really one thing that stands out in terms of what I want in my work and from my employer:  everyone at work deserves respect and the opportunity to have their suggestions and opinions seriously considered, and thus, feel that they are an active contributor to the organization and its purpose.”


Question #7.  How long would it take you in this role to make a real contribution to the organization?

Answer:  “Naturally there would be a short learning curve while I get up to speed in the role, but in the past I have thoroughly demonstrated myself as a quick learner who can make meaningful contributions in a short period of time.”  Then, provide specific examples and close with something like:  “I see this opportunity as no different than the many quick contributions I have accomplished previously in my career.”


Question 8.  What would you most like NOT to do in this role?

Answer:  Be careful with this one.  Essentially the interviewer is probing for things that you did not like doing previously and then will ask the follow up question as to why you did not like them.  Don’t fall into this trap of focusing on the negative.

Instead, turn the question around and provide an answer with a more positive spin such as:  

“In a perfect work world, I would like to avoid the bureaucracy and red tape that can, and does, delay decisions.  Like anyone, I am always keen to have progress made quickly and for everything to run smoothly.”


Question 9.  What would your job references say about you?

First things first:  Make sure you are using the right and most impressive references.  The best way to do so is to have a friend or colleague pose as a potential client and ask for feedback from the references you planned on using.  The results might surprise you.  If the reference says anything negative about you and your abilities, you should NOT use them as a reference.

These calls are also an awesome opportunity to get independent feedback you can use to improve your performance.  Here are some suggested questions for these reference checks: 

  • What are the best things about working with her/him?
  • Is there anything that she/he could improve upon serving you as a client?
  • Do you strongly recommend that we work with him/her?

The references you use should be people that are citing your greatest strengths.  As such, take the time to list your best job strengths and behavioral qualities.

Begin answering Question 9 by starting the sentence in the 3rd party such as “My references would say . . . . “  Any time you are replying in the 3rd party, it sounds like someone else is endorsing you, which is exactly what you would want your references to do.  Many people claim to have very strong references, but if you answer this question using the 3rd party endorsement, then it will add far greater credibility to your statement.


Question 10.  What favorite song best describes you and why?

Obviously, you are not going to do well if you cite Johnny Paycheck’s song “Take this job and shove it.”

Instead, choose a song that mirrors your top job strengths.  As an example, Van Halen’s song “Jump!” begins with the words “I get up, and nothing gets me down!” which illustrates resiliency, perseverance, and optimism, all of which would be great strengths for any job candidate.


Question 11.  What is your favorite movie and why?

Much like the previous question about your favorite song, you do not want to choose a movie known for its negativity.

Instead, cite a movie that illustrates your greatest job strengths.  For example, “Shawshank Redemption” would be a great film if your strengths are mental fortitude, recovery, and delivering justice.


Question 12.  Why should I hire you?

This is one of, if not the, most important question for which to prepare.

As such, you should have 3 or 4 statements pre-prepared.  These statements should relate directly to the job description for the job.  Then, add in the personal qualities and strengths that make you ideal for that role.  Again, it sounds better if it comes as a 3rd party endorsement such as “Colleagues have described me as . . . I am a great team player, technician, motivator, . . . “

You should also be prepared to share specific examples of these strengths and qualities, which you can offer to expand upon.

Lastly, you should close your answer with a statement such as “Do you think these qualities are what you are looking for in a successful candidate?”  Needless to say, a statement such as this strategically plants a seed in the interviewer’s mind that indeed they are the exact qualities sought for this position.  


Whether it is from the Boy Scout’s motto or the song from the 1994 Disney film The Lion King, “Be Prepared” should be your mantra when it comes to facing the 12 Toughest Job Interview Questions.   

And also, don’t forget that this is as much of an interview about their company as it is about you.  As such:

  • Make it a point to ask about the organization’s stated mission, vision, and values.
  • Go out of your way to explore what you found on the organization’s social media accounts.  Not only will this impress the interviewer that you were proactive about reviewing their social media presence, but you will also be able to inquire about any implications on how the organization presents itself and its values to the public.
  • Pay attention to the interviewer themselves.  Are they engaged?  Do they appear to be diverse or active promoters of D&I?
  • If the interviewers say that they are looking for the candidates ‘cultural fit,” make it a point to ask them to elaborate on what that means.
  • Ask the interviewer where they see the organization in five years, both in terms of size, culture, and where this particular job position might lead in terms of career growth. 


Kevin Sheridan is an internationally-recognized Keynote Speaker, a New York Times Best Selling Author, and one of the most sought-after voices in the world on the topic of Employee Engagement. For five years running, he has been honored on Inc. Magazine’s top 100 Leadership Speakers in the world, as well as Inc.’s top 100 experts on Employee Engagement. He was also honored to be named to The Employee Engagement Award’s Top 101 Global Influencers on Employee Engagement of 2017.

Having spent thirty years as a high-level Human Capital Management consultant, Kevin has helped some of the world’s largest corporations rebuild a culture that fosters productive engagement, earning him several distinctive awards and honors. Kevin’s premier creation, PEER®, has been consistently recognized as a long-overdue, industry-changing innovation in the field of Employee Engagement. His first book, Building a Magnetic Culture, made six of the best seller lists including The New York Times, Wall Street Journal, and USA Today. He is also the author of The Virtual Manager, which explores how to most effectively manage remote workers.

Kevin received a Master of Business Administration from the Harvard Business School in 1988, concentrating his degree in Strategy, Human Resources Management, and Organizational Behavior. He is also a serial entrepreneur, having founded and sold three different companies.