Jillian Kurvers

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Applicant tracking should keep your hiring process organized and efficient, but a human touch must guide each step of the way. Never is that more apparent than in the required nuance and personality of the interview. Human influence doesn’t mean you can afford to lose all efficiency in each interview though.
So we found and summarized the 5 Toughest  Interview Questions, as listed by U.S. News & World Report. Use them to ensure the quality of your hiring doesn’t get cheapened by easy questions and unhelpful information.

Use these questions in your interview

…but be warned. These questions are hard.

“How long are you willing to fail at this job before you succeed?”

Jon Sterling, co-founder of Interview Circuit.

Questions that don’t solicit exact or quantifiable answers are tricky for both parties. You’re not asking for an experience or degree, but the answer could be interesting. You can see if this applicant handles curveballs well.

“What are you most proud of in your career?”

Kimberly Bishop, retained executive recruiter

This question packs more punch than you think. You can see what this candidate values most, or they may not even have an answer. Either way, you have material to explore and discuss.

“What skills are you lacking?”

Mel Carson, Delightful Communications

This is a more objective (less cliched) version of the greatest weakness question. You can learn this applicant’s awareness of current market expectations and their self-valuation. Skill tests in your Applicant Tracking Software can help you cross reference their abilities with their self-assessment.

“Which past manager has liked you the least, and what would this person tell me about you?”

Allison VanNest, head of communications at Grammarly

Make it clear you don’t want names. This is such a touchy question, that we hesitate to even list it here. But hey, it is tough. Ideally, you’ll learn about how this applicant handles conflicted interests and disagreement.

“Tell me what you felt was unfair to you in your last job.”

Don Phin, president of HR That Works

How the applicant answers will tell you a lot about how they assess blame. Do they pick an example where they do nothing wrong? Most business relationships aren’t so clear cut. Every situation is a learning situation. An applicant, wise from past experiences, will bring that wisdom to your business.

Guide your ATS experience

Effective applicant tracking starts with the early sourcing of candidates, helps you screen unqualified applicants and then helps you make the hiring decision. One aspect left untouched by digital applicant tracking is the human interaction of the interview. These questions should help keep you on track.

Extra (semi)-hidden tip

(Once you finish with them, use weighted evaluations to compare each candidate with your team.)


Have any difficult questions of your own? Leave a comment below or check us out on FacebookTwitter or LinkedIn.

  • Liz Searcy

    As an experienced interviewer, coach and recruiter, I appreciate these questions. I role play with my candidates, asking them tough questions like these. Here’s more to add to my growing list.



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