4 Ways to Be Ready for the Difficult Interview Questions

The cardinal rule of interviewing seems to be “never say anything negative on an interview.” But that does not mean the hiring manager will not ask you about the blemish, challenge or failure in your past that you would prefer not to talk about, if given the choice. Despite your best efforts, the interviewer will find a way to ask you about your unreasonable boss, the company that went bankrupt, your layoff, the sales plan you missed, the budget you exceeded, the gap in your resume or your nutty co-workers. Or maybe you were fired—<gasp>. How do you diplomatically and confidently discuss these issues with a prospective employer, when what you really want to do is hide in the nearest corner when they arise?

Here is how to prepare to ensure you are ready and do not slip on these questions when the interview will inevitably take the turn down this precarious slippery slope:


(1)    Embrace Your Story – Don’t Hate It.

You are who you are. Your path is your path. The story you have is what makes you–you, like it or not. I can tell you not many people have the perfectly progressive story to tell—especially with the economic turbulence experienced over the past four years. Employed or unemployed, many job seekers are telling stories about how they lost a job, missed plan, did not grow marketshare, lost key accounts, transferred to a job they did not want and/or harbored increased vendor costs. So you are not alone.  What separates you from the pack is not the content of your story—but how you tell it. All things equal amongst candidates, it is my belief that the candidate that tells his/her story confidently with some vulnerability and humor wins the hiring game.


(2)    Expect these Questions Will Be Asked and Have Your Answers Ready.

Don’t stick your head in the sand and hope “they just won’t ask.” I am a big Murphy’s Law believer and, in my opinion, ignoring this fact it is the surefire way to ensure they DO ask you.  Ask a trusted friend, colleague, mentor or coach to go through your answers with you for these challenging questions and have your answers well-thought out in advance. No memorizing—but do not have the first time you think about how to answer these questions be on the interview. Word choice and repeated practice will improve your confidence dramatically with the interviewer when he/she asks this question. This will set you part from the pack.


(3)    Take Inventory of All You Learned from Your Challenges and Hardships.

People love stories of positive people who muddled through and triumphed over tough situations. The public typically loves the underdog. Most people are a sucker for the proverbial “Make Lemonade Outta Lemons” story.  The key here is not to complain about your situation or ruminate about how incredulous the predicament was, but to share what you learned about yourself and about the business and how you are going to apply it going forward to breed success. When describing a negative or challenging situation, you always want to outline what you learned from it. That is what hiring managers want to hear from their prospective employees.


(4)    Don’t Think You Are Different.

I know I am getting a few eyebrows on this one.  But yes, your story is not new.  Everyone has a story to tell. Who hasn’t had a boss who could not manage to turn on a computer, never mind effectively manage a group of people. Who hasn’t had an unrealistic sales plan, a terrible territory, selfish co-workers, too many overly needy clients or inadequate tools at hand. We all have encountered these situations—this is life.  If you make yourself appear so unique in having to deal with this stuff, you may be perceived as someone who cannot handle life’s adversity with fluidity, grace or competency.  Better to communicate how you accepted your challenges and demonstrate how you learned from that demanding boss—after all he did make you realize that you can handle more than you ever thought you could. Share that discovery with the hiring manager before you.

Written by Lisa Rangel, Executive Resume Writer


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