Created By Annie Jennings PR, National Publicist  
Like JenningsWire On Facebook

RoundUp: What Job Interview Questions Keep You Up At Night?

Is it “what would your former boss say about you?”

Or the dreaded “tell me about yourself?”

JenningsWire queried real life job candidates, as well as the pros, to find out what oddball questions caught them off guard.  Not only do you have to prepare for the expected, but have to have a game plan to deal with the unexpected.  You can find out how other job seekers answered their unexpected questions and the career experts weigh in on why these questions are asked and how to answer them by tapping into what makes you special.

First, here are some typical job interview questions for you to see how ready you are for a savvy interview.  What would you say if asked:

  • How long do you plan to say at our company?
  • Are  you willing to work overtime?
  • Can you describe your ideal job . . . in detail?

Don’t know what you would say? It’s OK for now, but this is a sign that you have some interview prep work to do.  Hiring a new employee is very serious business for the employer as they really need and want to choose the best candidate for the job. It’s a  jungle out there and the right team can make a big difference in the ability of the company to compete for and win new business. Plus, keep this in mind, the job interviewer’s reputation is on the line within the company.  At the end of the day, the person who recommended that the firm hire you will be judged on his or her ability to make a ‘good hire’.

How do they make sure you are their best choice?

One way is by throwing oddball questions at you.  They are a test.  A pop quiz.

Career strategists seem to agree that oddball questions such as ‘what color balloons would you have at your birthday party and why’, ‘what did you have for breakfast’, and ‘what do you do on the weekends’ seem to work their way into the job interview process. Why? The pros say the job interviewers want to see your reaction, how quickly you think on your feet and how creative you are at the spur of the moment.

Oh wait, there is one more question that seems to throw a monkey wrench into the interview, it’s “what do you do for fun?”

This question surely will do you in if you are not ready for it because all of a sudden you might not remember what you do for fun.  In fact, you might actually blurt out “nothing”.  When in reality you do lots of great stuff for fun. You have great hobbies, you play the piano, you coach softball, you volunteer at the soup kitchen, you enjoy exploring new towns and watching funny movies, you bring your spouse or significant other flowers ‘just because’, or maybe you are an amateur chef, but considered an expert by friends, who throws awarding winning BBQ’s (who wouldn’t hire you now?).

Let’s hear it from real life job candidates.  What did they ask you?  What happened next?

Question:  When I left University in London I went for an interview at one of the biggest firms in the United Kingdom (and now the world), and the guy that interviewed me seemed to be a huge and formidable monster of a man. He turned out to be one of the best bosses I’ve ever had. I was very nervous as you can imagine and, after browsing over my resume he leaned back in his chair, stroked his beard and then lunged forward, glaring into my eyes and said “SO!  Why you and why us?” To which I replied “Why not?” as it seemed natural to respond in this way. He burst into laughter, shook my hand and said “Start Monday?” I said “OK”. And that was that.

Feedback:  I was always told to ‘be yourself’ as I would say to my children and employees now also. I don’t think I would have answered it in any other way. If I’d have launched into all the reason why them and why me, he’d have been bored.

Job interview story submitted by David Gilhooley, Wedding Artist and creator of ‘The Wedding Sketchbook’. You can connect with David at Dave6544.com or Facebook The Wedding Artist

Things were going well until . . .

Question:  I was being interviewed for an editorial position at a large health publishing company. Things were going well until the exec who was interviewing me asked me what I’d had for breakfast that morning. “Grape Nuts,” I blurted out, remembering too late that this was a brown rice and tofu kind of place. I didn’t get that job but a few weeks later landed a better job in the company’s book division.

Feedback:  Would I do things differently? Probably not. I don’t think lying in a job interview is a good policy.

Job interview story submitted by Kae Tienstra, president KT Public Relations & Literary Services

Why shouldn’t we hire you?

Question:   When I was first being screened for my director of marketing communications position at Halogen Software,  I went through a series of thorough interviews. In my first one with HR I was asked a question that was quite unexpected but that I was quick and happy to respond to. It was a much more interesting approach to a conventional weakness question – it went something like this:

“A lot of companies might ask you why we should hire you…I’d like to have you tell us why we shouldn’t hire you.”

Feedback:  It was interesting because it made you reflect on yourself quickly and for me, it inspired a pretty authentic answer. I said something to the effect of “Well you’re a growing company that is moving at a really fast pace. If you’re looking for a marketing director who is going to just set strategy and not get their hands dirty doing tough execution work, then honestly, you shouldn’t hire me. That’s not me.” I’m pretty sure they were pleased with the answer. It’s been 5 years since that interview!
Kind regards,

Job interview story submitted by Connie Costigan, Director, Marketing Communications, Halogen Software.  You can follow Halogen on Twitter and like Halogen on Facebook.

Can you sing something for us?

Marilyn Santiesteban, Assistant Director of Graduate and Alumni Career Services with Bentley University Alumni, says that students report that wacky interview questions are on the rise.   They include:

  • How many manhole covers are there in NYC?
  • What color M&M would you like to be? Why?
  • What crime are you least likely to commit?
  • How many bicycles are there in San Francisco?
  • Sing something.

Marilyn adds that interviewers try to startle the well-prepared candidate by throwing out unexpected questions. Sometimes they want to experience how you process an answer – “To calculate the number of manhole covers in NYC (or bikes in SF), I would start by using Google earth to determine the manholes in a square block, then extrapolate…”.

Sometimes they want to see how you perform under stress by using the M&M question. It doesn’t have a right or wrong answer; the interviewer just wants to know how you deal with the unexpected. Keep your sense of humor – “I’m trying to choose the company logo colors; do M&Ms come in chartreuse?”.

Most of us are nervous about singing in public, so stick with something easy.  Belt out “Happy Birthday” with a smile and all the confidence you can muster.

Take the unexpected in stride!

Job interview advice contributed by Marilyn Santiesteban, Assistant Director of Graduate and Alumni Career Services Bentley University, Nathan R. Miller Center for Career Services.  Connect with Bentley Alumni on Twitter and/or LinkedIn.com 

What board game would you rather play, Monopoly or Scrabble?

Dana Manciagli, Global Career Expert and author of the upcoming book (Spring 2013), Cut the Crap, Get a Job!,  has experienced multiple odd interview questions, both from her own job searches, as well as those she coaches. She has been asked “What board game would you rather play, Monopoly or Scrabble?” and “If you were stranded on a desert island, who would you want to be stranded with and why?”

Dana’s recommendations to any job seekers who are asked oddball questions are:

1.  Smile, and pause to think. Feel free to say “one minute while I think about this.”
2.  Be honest; don’t try to think about what they want to hear.
3.  Dana’s “Law of 3’s”: Say the answer and three short comments then stop talking. Don’t ramble, pause. Let them drive the next question.

“Candidates need to know that interviewers are simply looking for your ability to think on your feet and how you communicate clearly and concisely,” says Dana Manciagli. “They can also reveal personality traits like sense of humor, honesty and more.”

See more interview advice from Global Career Expert, Dana at DanaManciagli.com.  Please connect with Dana on Twitter, Facebook, Youtube, LinkedIn and Pinterest.

What do you like to do on the weekends and your days off?

Feedback:  I thought it was an oddly personal question, but then I quickly realized it was appropriate for the job because this particular position had me traveling and living in multiple cities around the world for extended periods of time. They wanted to make sure to hire someone who could easily adapt to new surroundings and not get bored when away from home. So I answered that I enjoy spending my free time exploring new restaurants and parks with outdoor activities. I also mentioned that I used meetup.com to find out about new experiences and activities going on in new cities. I wouldn’t change my answer. It landed me the job!

Job interview story submitted by Heather Curtis, Marketing Manager, TheeDesign Studio.  You can connect with Heather on Facebook and Twitter.

Do you love pina coladas and getting caught in the rain?  Think of the interview as a first date.

Shariq Abdul Ghani, Partner and Chief Job Strategist of SmashingResumes.com says oddball questions will definitely become the norm. Hiring managers today have the luxury of choosing not just the best skill set, but the best personality fit as well.  Hiring managers (including myself), have the opportunity to pick those who will work the hardest, will want to stay loyal, AND will get along with everyone else and hang out at all the office parties. These questions enable us to dig a little deeper into their personalities. Do they play ball, smirk, laugh, throw a joke back at us, or outright say it’s unprofessional and give us a weird look?

I would say to think of an interview as a first date. It’s just as important for them as it is for you to establish who the other party is, their background, their experience, and if they can satisfy your emotional and workplace needs. Are they going to be argumentative? Are they going to be respectful? Will they stay late and work more hours if needed? Are they optimistic or pessimistic? Will they jump ship at the first sign of trouble or dissatisfaction? And after the interview, it’s important for both parties to analyze if they should go on a second date or call it quits.

If you see interviewing as dating, you’re more likely to be ready for professional questions AND oddball questions. At the end of the day, the candidate and the company are both trying to see if they’ll be a good fit for a long-term relationship.

Job interview tips submitted by Shariq Abdul Ghani, Chief Job Strategist at Smashing Resumes. You may also connect with Shariq on LinkedIn.

Here it is.  The ‘what do you do for fun?’ question and why this job interviewer asks it . . .

Jan Mendoza, Owner and CEO of Rocket Rosie Professional Development Academy,  says that “I instruct my students/clients to be ready for anything when it comes to a job interview.  Employers aren’t only looking for people who have the skills to do the job, they are looking for people who will get along and fit in with the rest of the team.”

Let’s say you have five people interview for the same job.  All five candidates have the skills, education and all candidates will most likely perform well.  Now you must pick one.  This is where you need to dig a little deeper and find out how each person ticks and if they would fit in your environment.  Let the crazy questioning begin.  When that employer is asking you what color of balloons you’d have at your party, it’s a way to  determine your character and personality in an unscientific sort of way. Or, it is a way for them to determine not only your personality, but how quick you can catch a curve ball and throw it back.

When I am on an interview panel, my favorite question is: “What do you do for fun?”   You’d be surprised at the amount of people who choke at this question.  It seems like a pretty simple question, right?  Well, I’ve been able to make a tough decision on hiring one person over another  just by this question alone.  I can get a glimpse into the “real you” and not the “I’m here for a job interview” you.  I recently had the hard decision to hire a PR specialist and it came down to three people who ALL had awesome qualities. I wish that I could have hired all three. The question I asked that helped me tremendously in my decision was “How would your friends describe you in ONE WORD?”  The answer that won me over…Joke-ster.  I knew right away she’d fit perfectly with the team because we all love to laugh.

Job interview tips submitted by Jan Mendoza, Owner and CEO of Rocket Rosie Professional Development Academy.   Jan is the author of  three books: I was Born to Be, I was Born, Now What and the recently published best seller, Fire Girl.  Please visit Jan Mendoza at JanMendoza.com 

This job interviewer asks this one tough question . . .

Kelsey Meyer, President of Digital Talent Agents, who has interviewed over 100 job candidates in the last year, says “I ask the same tough question to all interviewees.  I ask them to teach me something.  I give them a pad of paper and pen and give them a few minutes to collect their thoughts then I time them for 5 minutes while they teach me whatever they want.”

I ask this to see how they perform under pressure, how creative they are with what they decide to teach me and the main reason is to test their communication skills which is the most important skill we hire for.

Job interview story contributed by Kelsey Meyer, President, Digital Talent Agents.  You can also visit Kelsey at  LinkedIn 

Why would anyone ask you “if you were a fruit, what fruit would you be and why?”

Cammie Scott, President of CK Harp & Associates says “one question we ask is ‘If you were a fruit, what fruit would you be and why?’ We ask for a written and verbal response. We are looking for creativity, the ability to think on your feet and good written and verbal communication skills.”

One of the best answers I ever got was, “I would be a watermelon because I am hard on the outside and soft and sweet on the inside and pink is my favorite color.” This was a creative answer that told about the applicant and had a good thought process to back it up. It made that person stand out from the 30 or so other applicants we had for that position.

Job interview story contributed by Cammie Scott, MSIE, LUTCF, RHU, REBC, CLTC, ChHC, SPHR, President of CK Harp & Associates

What is a quarter of a half?

Bob Bentz says that in his previous career of selling television advertising, he had an interviewer ask me the following question:  “What is a quarter of a half?”  In a way, I was a little offended with the question for him to think that I wasn’t smart enough to know the answer. The answer was quite simple so I confidently said “an eighth.”

When I started my own business, I began incorporating this question into my interviews. Here are the potential answers:

  • Get the answer wrong.  “Ahh, ten”
  • Don’t give an answer. “I’m not very good at math.”
  • Confidently give the wrong answer.  “Five”
  • Give the right answer, but aren’t sure of themselves. “Is it one-eighth?”
  • Give the right answer confidently.  “One-eighth”

Why he asks:  I am looking for talented and smart people who not only know the answer, but are confident that they know the answer.

Job story submitted by Bob Bentz.  Bob is the president of Advanced Telecom Services in Wayne, PA, that provides mobile marketing solutions for brands, media, and advertising agencies.  Bob Bentz is also the author of “Opportunity is Calling” and many articles on the web.  Bob is regular speaker at international trade shows. You can visit with Bob on  Twitter, LinkedIn.

But what if you think the question is inappropriate?

Career Strategist, Julie Bauke, President of The Bauke Group and author of  Stop Peeing On Your Shoes: Avoiding the 7 Mistakes That Screw Up Your Job Search says that sometimes, if you are interviewing for a job that is very high stress, the interviewer is trying to simulate stress in the interview by asking very difficult questions and seeing how you answer them. It is ok to say with a smile “I’ve never been asked that before. Can you give me a better idea of what kind of information you are seeking?”

If you really think it is an inappropriate question, (focuses on race, gender, religion) you can say “can you help me understand how this relates to the position?” If you do say that, realize that you may be killing your chances with that company if the interviewer takes offense. But sometimes, asking them gives them a chance to clarify the meaning behind the question, as you may have misunderstood. If the question is really offensive, you don’t want to work for that company anyway.

Job interview advice contributed by Career Strategist, Julie Bauke, President of The Bauke Group and author of  Stop Peeing On Your Shoes: Avoiding the 7 Mistakes That Screw Up Your Job Search.

Tell me about your best friend . . .

Career Coach, Ronald Kaufman, author of Anatomy of Success, has over 10 years of hiring experience and says, “there are thousands of possible questions that can be asked, but it still comes down to two main things.  You need to convince the interviewer that you can give them the results they want and that you want a career with their company, not just a job.” Ronald shares the following advice with us:

It’s essential to thoroughly research the company (products, industry, leaders, competition, web presence), and be able to show them how you will be an asset to help them achieve their goals.  You need to know yourself in terms of skills and traits, and have concrete examples that prove you have the skills and traits that they feel are important for the job.

Oddball questions give the interviewer a sense of your personality.  “Tell me about your best friend,” deals with the saying of “birds of a feather, flock together.”  Whatever you say about a best friend could be an indication of what you’re like.

A question such as “If you were an egg, what kind of egg would you be?” like all answers needs to be tailored to the job.  If it’s a sales or customer service position, then sunny-side up would make sense.  If it’s for a supervisor on a production line or a negotiator, then hard-boiled might be appropriate.

As a youth, what did you do for fun?  This could be answered by talking about sports if it’s a job dealing with teamwork, or playing video games if it’s for a computer or IT job.  Your answers need to show you are the type of person who could be successful in the job and that you would fit-in as a person.

Job interview advice contributed by Career Coach, Ronald Kaufman, former executive with over 10 years of hiring experience and over 15 years of experience as a Career Coach.  Author of  Anatomy of Success: The Ultimate System For Setting & Achieving Your Personal & Professional Goals.  Please visit with Ronald Kaufman at AnatomyOfSuccess.com

Why do they ask oddball questions in the first place?

Josh Tolan, CEO of Spark Hire, a video powered hiring network that connects job seekers and employers through video resumes and online interviews, says that interviewers ask oddball questions because they’re trying to catch candidates off guard and find out more about the candidate. Whether the interview is in person or through online video, candidates will slavishly prepare for interviews in advance. They might have a well rehearsed answer ready for all of an employer’s commonly asked questions.

This won’t tell the interviewer much about what the candidate is really like or how they’ll actually fit into the company, but only how well they’ve prepared for the interview and memorized their answers. Asking oddball questions helps the interviewer knock candidates off their script. It allows employers to see how candidates answer off-the-cuff for questions they couldn’t possibly have prepared for. It also gives some insight into the candidate’s thought process and personality.

If you ask a candidate what color they would be, do they just name off a color or do they explain themselves and connect it back to the job? This let’s you know how well candidates can think on their feet and adapt to change. Candidates who do so without getting flustered and dropping the ball will seem like the kind of quick-thinking employees a company could use in open positions.

As an applicant, it’s hard to prepare for these curveball questions. The best applicants can do is to keep in mind the skills necessary for the job and the value they bring to the company.

Whether these questions are popped into an in-person meeting or a video interview, the best way to react is to use the answer to show off your value to the company. No matter how much of a curveball the question is, if you can relate it back to the job at hand employers will be impressed with your smarts and focus.

Strange questions are fairly common in job interviews. Most candidates will get at least one or two questions aimed at knocking them off their scripts and getting a more genuine response. Companies use these questions to learn more about candidates and discover if they will be a good fit for the company culture.

Job interview advice contributed by Josh Tolan, CEO of Spark Hire.  You may also connect with Josh on Twitter.

The interviewer said, here is the most critical question of them all . . .

Linda McGrath was at her first interview in her new job search and says that the interview was nothing if not bizarre. It lasted for almost an hour and the topics swung wildly between what they were going to have for lunch after the interview, to what they had done that weekend. Towards the end of the interview, one of the women leaned over and said she had the “most critical question of all.” I was expecting her to ask what salary I was looking for, but instead, she asked, “If you had to choose between American Idol and Dancing With The Stars, which would be your favorite?”  I was really caught off guard and said that I didn’t like either show and didn’t watch them. She seemed genuinely annoyed at my response, and started talking about how much they both loved both shows and that clearly I wouldn’t be a good fit for their team. As I left, I knew they were right, I wouldn’t be happy there. I wasn’t at all surprised that I never heard back from them and I wasn’t disappointed either.

Job interview story contributed by Linda McGrath-Cruz, Owner of Linda’s Paralegal Resources. You may also connect with Linda on LinkedIn.

What inspires you?

If you want creative employees who can think on their feet, you have to ask unexpected questions. With clichéd typical interview questions,  everyone knows the “right answer.” I  like to ask, “What inspires you?” or “How do you hope your work will impact the world?” Unconventional  questions can lighten the mood, give a sense of how applicants conduct themselves on the spot, and give you a better glimpse of  someone’s true personality.

Job interview story contributed by Elle Kaplan, CEO & Founding Partner, Lexion Capital Management LLC.  You can visit Elle online at LexionCapital.com  Facebook, Twitter and LinkedIn.

Job interview tips on how to be ready for just about anything

Dr. Marlene Caroselli is the author of over 60 books, including Hiring and Firing, The Language of Leadership, and Principled Persuasion, contributes these tips:

It’s been said that every time you open your mouth, you allow others to see into your brain. Oddball questions allow interviewers access to the way you think and the rapidity with which you can respond to stressful questions. Here are but a few ways to enhance your verbal fluidity and walk into an interview more confident than you’d be otherwise.

Anecdotes – Have a good (but definitely short) story ready to share with the interviewer. If it’s one you know by heart, you’ll be able to double-time your brain, asking it to tell the story on autopilot while you search for a specific reply.

Metaphors – Find a good metaphor for the workplace. It can be used for virtually any question asked of you.

Principles – If you’ve not already formulated some basic principles on which your business philosophy is based, do it now. You’ll be surprised at how often these can be massaged to create an outstanding answer.

Visualization – Muhammed Ali once refused to buckle up on a transcontinental flight. “Superman don’t need no seatbelt!” he told the stewardess. She must have “seen” Superman in her head, because she came back with the perfect response: “Well, Superman don’t need no airplane, either! Now, buckle up.” He did, chuckling the whole time. If you tend toward visualization, you will have an easier time than most in providing responses to those oddball questions.

Answer contained in previous comment – If you listen carefully, the perfect response is often embedded in something that has just been said by the other person. This technique doesn’t work in every situation but you can train yourself to listen for the opportunities.

Prepared lines – Have a relevant quote ready. Practice weaving it into various responses to questions you are likely to be asked. Or, have a favorite stalling statement ready, to give yourself time to devise a good answer.

Dr. Marlene Caroselli is an author, keynoter, and corporate trainer. She has published over 60 books, including Hiring and Firing, The Language of Leadership, and Principled Persuasion, named a Director’s Choice by Doubleday Book Club.   You can connect with Marlene Caroselli – Saatchi Online 

So, what have you accomplished?

According to Debra Ann Matthews, Professional Resume and Job and Career Transition Coach at Let Me Write It For You! says that “interviewers are looking for common trends in behavior when they are asking questions. They ask questions to gauge motivation, ability to work with a team and questions to determine if you are a person who does quality work.” Debra adds that “to prepare for any interview, write out 5 to 6 things that you do best and 5 to 6 things that you don’t like but describe how you have grown as a person as you have developed in this area. Also make note of 2 to 3 things that you have accomplished as an individual and 2 to 3 things accomplished in a team.

Job interview advice contributed by Debra Ann Matthews, Professional Resume and  Job and Career Transition Coach at  Let Me Write It For You!

What if you know the answer, but forget it when asked?

John T. Rogers is a communications manager for a private, non-profit university in Denver, Colorado and shares his story:

The question that caught me off guard in the interview for my current position was, “Define rhetoric.” The question somewhat made sense, being that I am a communications professional; however, I was surprised by the power of those two words and wondered what kind of response the interviewer was looking for (they happened to be a former English teacher). My response was, “Um…the art of speaking?” Clearly, if I had it to do over again, I wouldn’t have said ‘um,’ or responded in the form of a question. I ultimately got the job and will be better prepared if ever asked that question again in the future.

Job interview story submitted by John T. Rogers, M.S., Communications & Media Relations Manager.  You can connect with John on his LinkedIn

Doesn’t the question cross the line?

The strangest and most unexpected question I was ever asked was, “Have you ever, or would you ever cheat on your wife?” It surprised me because I couldn’t see how it related to a store manager position.

Of course I knew what the answer was but I asked him how that stupid question has anything to do with this position? His answer was that they have had problems with staff members that have strayed with other staff members and when their partners find out, they come into the store and create a scene. They want to avoid those situations with future employees.

I said to him that it was one of the most inappropriate questions I have ever been asked during an interview and that I would report him to his HR department.

Needless to say I didn’t get the position and to be honest, after that,  I wouldn’t have taken it anyway. If I had to do it all over again, I wouldn’t do it any differently.

Job interview story submitted by Andrew Radics, Managing Director at a Digital Marketing Agency called The Expert SEO Company, search engine optimization, social media and web development company.

Note from Annie:  I think the most shocking interview ANSWER I ever heard came out of the mouth of my daughter, who by the way, won numerous awards and recognitions for her outstanding accomplishments, in an extremely challenging field, and graduated from college with honors (just telling you this to set the stage for the bizarre turn of events that happens next).  Well, she was at a very important interview ‘that a million girls would die for’ and the interviewer asked what where her plans for her future . . .  and she said, “how the BLEEP do I know?”  As she told me the story, my eyes must have popped out of my head at that point as thoughts of all of the college tuition started spinning around in my head.  HOW COULD YOU?  I asked.  She said, “it just slipped out, I guess.” She said the interviewer burst out laughing and she got the job.

Annie Jennings is a National Book Publicist and Creator of JenningsWire Online Magazine.  For more article by Annie, please click here.


The online feature magazine, JenningsWire.com, is created by National PR Firm, Annie Jennings PR that specializes in providing book promotion services to self-published and traditionally published authors. Annie Jennings PR books authors, speakers and experts on major high impact radio talk interview shows, on local, regionally syndicated and national TV shows and on influential online media outlets and in prestigious print magazines and newspapers across the country.

More Recent Posts

Video Blog Post Mini Promos

Money Eight Financial
Secrets That Could Change
Your Life
School Struggles Listen Up Moms: Trust Your Judgement
Personal Growth 3 Types Of Relationships

Leave a Reply

Submit Comment