Lindsay Olson

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“What’s Your Greatest Weakness?” and Other Hard-to-Answer Interview Questions

Question mark in Esbjerg
You know it’s coming. The dreaded interview question.

“What’s your greatest weakness? or “Where do you see yourself in five years?”

Questions like these set you up to be tongue tied. How can you answer them and seem like you’re giving a true-to-self answer, while still pleasing your interviewer?

One thing to note: questions like these are often asked by untrained interviewer. It’s a typical question that usually generates a typical response. It’s easy to say that your greatest weakness is being a perfectionist, or wanting to take on too many projects at once. Isn’t that the answer that the hiring manager wants to hear? Not always.

How do you answer these questions other than to give the interviewer what you think she wants to hear?

Go Into Your Interview Armed with Answers

If you know what to expect in terms of questions, you’ll be less likely to draw a blank for an answer. Read up on the most commonly asked interview questions so you know what to expect. Then, before your interview, sit down and consider how you would answer some of the commonly asked questions (even the dumb ones). Practice your answers in front of a mirror. Aim to make eye contact and be confident in your answer. Repeat this until you stop laughing at yourself!

Aim for the Diplomatic Truth

Sure, you may be applying for a job simply because you need a job, but that’s probably not the answer that will get you hired. Find a better way to word the truth.

Why are you interested in our company?

The truth: They pay well and have a killer bonus structure.

The better truth: Explain that you’re looking to expand your experience. You like the structure. You feel it’s a place where you can help make a difference and find that your core values align with theirs (make sure you know their core values and you’ve read their mission statement!).

What did you leave your last job?

The truth: Your boss had it in for you.

The better truth: You were ready for a new opportunity that would allow you to grow.

What’s your greatest weakness?

The truth: You have none! Of course….

The better truth: Be honest. Pick your true weakness, but be ready to show how you have worked to improve it and how it can also be a strength. Maybe it’s that it’s hard for you to delegate, or the fact that you’re no good at multitasking (that’s actually not a weakness, despite what employers would have you believe). Shape your answer so that the hiring manager sees that you are aware of a weakness, but are ready to make it work for you.

Realize that the interviewer may be trying to bait you to see if you’ll talk negatively about a former employer. Don’t fall for it. Never show your emotion or frustration for a previous employer in an interview.

Also, an employer might present these difficult questions simply to see if you have a realistic sense of self. Telling them with what they want to hear may not score you points. Be true to yourself and don’t pigeonhole yourself into a place you don’t want to be in. If you get the job, you certainly don’t want to have presented yourself falsely in the interview.

Photo credit: Alexander Drachmann

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.


11 Ways to Size Up a Prospective Employer

Questioned Proposal

Here’s an excerpt of my post this week on US News & World Report’s On Careers:

The job market is picking up. Companies are hiring and candidates aren’t as nervous to consider working for a new employer. The fear of being the “last one in, first one to go” is slowly diminishing as employers are aggressively seeking to fill new positions.

Before running to the altar with a new employer for promises of a higher salary or better job title, it’s important to make sure it’s a feasible long-term career opportunity. The most regrettable job decisions can be avoided by asking probing questions throughout the interview process.

Read it here –> 11 Ways to Size Up a Prospective Employer

Photo credit: Ethan Lofton

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