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Embarrassing moments and other challenging interview questions
By Joan Lloyd
Joan Lloyd

Dear Joan:

Can you, or someone, explain this to me.  When you are on a job interview, and the interviewer asks, "What is your most embarrassing moment?" what are they looking for? And why?

Any assistance you give will be greatly appreciated.  It's one of those questions we, my friends and I, ask ourselves.  We aren’t sure why it is relevant in an employment interview.  What is this question all about?  We have children getting ready for the workforce and we are not sure how to advise them.

Thanks so much.

 Answer:

Your assignment: You have one hour to question and assess a total stranger, to determine if he or she would be a good employee. When the clock starts ticking, you have to determine his or her past work experience, work ethic, motivations, personality, weaknesses, quirks, future goals, fit with the rest of the team, drive for results, ability to work unsupervised…and, of course, decide if they have the basic skills to actually do the job in a reasonable manner.

 So, how, you may ask, can I get all that accomplished in one hour? What’s worse, if you make a hiring mistake, you not only waste all the time and money you spent hiring and training the person, you now have to clean up any damage and start over. It’s no wonder that interviewers will ask questions that seem a little odd, in order to learn more about the person who has so much potential impact on them and the team.

 “What is your most embarrassing moment?” might be asked for a number of reasons. It’s likely to be a question the candidate hasn’t rehearsed, so it can catch him or her off guard and open a window into their personality.

 Say, for example, the candidate responds, “I was standing up in speech class ready to give my speech and I completely froze. I was so embarrassed; I walked right out of the room. I dropped that class the next day.”

 If this is a service-related job, you want to hire people who can think on their feet, talk to complete strangers, and handle potentially difficult situations with some degree of composure.

 Contrast that answer with this one, “I was giving a speech and I completely froze. I stumbled around for a bit until I could remember my place. I’m sure my face was beat red but I finished my speech. I was so embarrassed.” This candidate experienced something most of us would find embarrassing, but his decision to stick it out tells you a lot about how he would handle a similar situation with a customer.

 Other questions might seem odd, too, such as “Tell me about one of your favorite vacations,” or, “If you could do any job in the world, what would it be?” As long as there is a job-related reason for asking the question, it’s legal and appropriate.

 These two questions, for example, might yield some helpful information about the candidate’s natural skills and interests. It can also give insights about the kind of work environment for which they would be best suited.

 Obviously, the majority of interview questions will be about past experiences, how they handled past team situations, and other specific job-related questions. However, good interviewers usually have their personal quirky questions they like to throw in, to try to uncover the real person on the other side of the desk.


Joan Lloyd
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Joan Lloyd Biography:
Since 1990, Joan Lloyd has grown her reputation as a premier executive coach and organizational development consultant. She helps leaders improve their skills and create healthy, productive workplaces. Companies both large and small seek her out when they want to change their culture, learn new leadership skills or improve the way their teams work together.

Most of her clients meet her first through her workplace advice column, called “Joan Lloyd at Work,” where her down-to-earth advice about job hunting, career development, leading and managing people and teambuilding puts her in the unique position of having credibility with both management and staff.

The column has been published, every week, since 1982. It appears in newspapers, magazines and on websites worldwide, including in Great Britain, Australia, India and Iraq, where it is translated into Arabic.

She has appeared on television more than 500 times and been a weekly guest on a radio call in show for more than 10 years.In addition to hundreds of articles she has written with tips and strategies for job hunters, her job hunting and career development tools include:

Savvy Negotiation Strategies to Get Paid What You’re Worth on a New Job
Easy, Step-by-step Guide to Using the Internet to Land a Great Job
How to Get Your Dream Job
The Resume that Gets Results and the Interview that Gets the Job
You, Inc. – Success Strategies to Boost Your Career
Creative Recruiting & Retention Strategies
Recruiting & Retention Booklet Series
How to Coach & Give Feedback learning system


Email your question to info@joanlloyd.comto have it considered for publication.

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