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Taking a “Q” from Job Interviewers: Career-Related Questions to Ask Yourself

Question mark made of puzzle pieces

This is a post by guest columnist, Alison Kenney.

Are you inspired at work?  Is your current job the perfect job for you?  If not, how do you decide what to do next?  Are you a good judge of your own strengths?  Recently I was reading an interview the New York Times did with Kathy Savitt, CEO of Lockerz, when it hit me…the same tough questions Kathy uses to grill job candidates during interviews can be turned around and used by the candidates to help identify the perfect job or qualities to look for in a new job.

Adam Bryant, who writes The New York Times “Corner Office” column asked Kathy Savitt what questions she asks in a job interview.  Here are some of her examples:

Q:           “What did you love most about the work you just finished doing?”

I imagine Kathy asks candidates this to get a sense of where their commitments lie.  I think it’s a good way to prioritize career goals and help focus a job search.  For instance, if you loved writing in your last PR job but loathed pitching media, perhaps you’ll find inspiration as a speech writer, copy writer or freelance writer.

Q:           “If you could take 100 percent of your abilities and create a job description, what would it look like?”

You can learn a lot about people or about yourself with this question.  It’s a way to turn the tables – rather than squeezing the candidate’s experiences and qualifications into a pre-existing job description, you can find out what someone is really like as a person.  Listening to which qualities are mentioned first or highlighted more than others is also telling.  It can also be a wake-up call to job seekers whose skills may be outdated or irrelevant to the positions they’re interviewing for.

Q:           “Who’s been the best manager you’ve ever had?  Who’s been the worst?”

The intention isn’t to name names here, but rather to focus on the qualities that were most, or least, appreciated in a manager.  Presumably this will also tell you what type of environment the job candidate is most suited for.  For instance, if your favorite manager was someone who gave you a lot of room to make your own decisions, to speak out publicly or to represent the business, you are probably not a fit for more structured environments with multiple managerial layers.

Q:           “If everyone here was a CEO and I was to make you the CEO of something, what would it be?”

Kathy says she asks that because she likes to get a sense of the candidate’s passions and what they want to “own” in a new job.  This is the ultimate segway into thinking about how you can invent or reinvent yourself, i.e. what do you want to be known for?

Q:           “Who’s your wackiest friend?”

This is another question designed to find out what someone is really like.  It can also be a good way to see what type of office culture is the best fit for you.  Do you have a lot of different types of friends (which could mean you get along with a variety of different people or are very outgoing)?  Once you start thinking about which friends are the wackiest, you’ll also start to think about what kind of influence these friends have on you or how their behavior affects you.

Of course, there is no shortage of interview techniques and personality quizzes that can help job seekers find their way along the career path.  Back in 2008, USA Today wrote about the turn interview questions are taking (toward crazy).    And U.S. News & World Report recently wrote about how to respond if you’re asked a “crazy” interview question.

What was the best interview question you were ever asked?

Alison Kenney an independent PR practitioner with more than 15 years of PR consulting experience. She is based on Boston’s North Shore and has worked with organizations in the technology, professional services and consumer industries. She writes a bi-monthly PR column on You can find her at Learn more about Alison Kenney.


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