The Surprisingly Challenging Interview Question

There must be something wrong with you! You prepare for job interviews ready to sell yourself, with examples of all that you’ve accomplished. The last thing on your mind is how you lost the XYZ account three years ago or how you failed Jim as his manager because you weren’t sensitive to how his divorce was affecting him and his performance at work. Simply thinking about these things saps your confidence; talking about them is not something you want to do with a prospective employer. But if you don’t anticipate being asked…how do you respond when the interviewer asks you to talk about your weaknesses or a time that you failed? You need to be prepared for this situation. This is often a deal breaker. If you cannot identify where you missed the mark and what you learned from the experience, you can be sure you just sent up a big red flag for the person sitting across from you.

Tony Vlahos, ExecuNet’s Head of Learning asked Career Strategist Harriette Lowenthal to share her thoughts on how to avoid sending up that red flag.


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In addition to being in a leadership position with ExecuNet’s Career Strategists and Coaches, Harriette works 1:1 with high-level senior executives, VIP members, to provide strategic guidance and coaching to help them land their next great opportunity. This includes uncovering their unique value proposition and defining competitive differentiators to advance their careers. Additionally, she provides detailed feedback for improving personal marketing collateral – well beyond a resume. There’s no one better qualified to speak on the subject of executive job search!

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William Flamme

William Flamme

William Flamme is ExecuNet's Associate Director of Content Marketing, where he develops engaging job search, career path, and leadership insight to build ExecuNet's brand recognition as the leader in senior-level executive job search and all matters career.

He delivers executive-level content across the various properties under the ExecuNet brand, amplifying the power of ExecuNet's expert voices and shaping the content strategy.

Prior to joining ExecuNet in 2008, Will earned a master's degree in education and taught fifth grade and sixth grade. As a teacher, he deepened his appreciation for the written word and mastered skills necessary for managing writers who sometimes view deadlines as homework. It is his training as an educator which allows Will to take complex ideas and make them simple for busy executives to understand and to execute.

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