Ask Our Experts: What's the Hardest Interview Question?

Each week, we ask our experts to answer a career question on behalf of our readers. This week’s question is about the hardest interview questions:
"What's the hardest interview question to answer and what tips can you give for answering it correctly?" - Anonymous
Here’s what our approved career experts had to say: "Tell me about yourself." "In my opinion, the most difficult interview question to answer is 'Tell me about yourself,'" says Bud Bilanich, author of Climbing The Corporate Ladder. "I suggest learning as much about the company and job for which you’re interviewing to prepare for this question. Cast your answer in terms that relate to the company and job." Jessica Holbrook Hernandez of GreatResumesFast.com warns candidates not to go off on personal narratives or share inappropriate information. "Keep it professional, avoid giving away personal information and focus exclusively on your career progression," she says. Norine Dagliano of EKM Inspirations suggests hitting these key points with one or two sentences for each:
  • A brief overview of your career path
  • 2-3 of your areas of expertise (job specific skills)
  • Your decision making/problem solving style (2-3 transferable skills)
  • Your reputation/what others rely on you for
  • Your passion/career mission
  • Your career goals
"What did you dislike most about your last or current boss?" The best way to respond to this is to give a non-answer like, “I recall working well with my boss, nothing really stands out as something I dislike about them,” suggests Dorothy Tannahill-Moran of Next Chapter New Life. "If you start picking apart a former or current boss, you are going into risky territory. You never know how it will be received; usually not well as the implication is if you bad mouth your current boss, you will do the same thing to the new one." "What has been your biggest success?" When answering this question, most people immediately think of their best achievement in their entire career, according to Rosa E. Vargas of CareerSteering.com. "What they need to bring up is the most relevant achievement," she says. Vargas suggests job seekers have examples ready that are relevant and position you as the ideal candidate, even if you have a greater (non-relevant) achievement in mind.

In the End, All Interview Questions Are Hard

"All interview questions are hard (and dangerous) when you try to tell people what they want to hear," warns Corey Harlock of Skillstoachieve.com. "I recommend knowing exactly what you want and need from a job and employer and tell them what you want them to hear. That is the difference between trying to 'not get eliminated' (common approach) and trying to get hired (fearless approach)!" Hardest interview question image from Stock.xchng

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