10 challenging questions to ask candidates

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Good interview questions help HR managers to grasp what they need to know about a candidate – their skills, their strengths, and potential cultural fit. However, with millions of guides, printed or online, telling candidates how to ace interviews, many candidates only give cookie-cutter answers that don’t tell much about themselves. This is often a frustration to managers and basically defeats the purpose of the interview.

Recently, Glassdoor posted an article sharing 10 toughest job interview questions from career coach Hallie Crawford. These questions do not only test the prospective employee’s wit, but more importantly reveal what they truly think.

Managers, prepare a few of these questions the next time you’re meeting with candidates.

1. If your current employer had an anniversary party for you, what five words would be written on the cake to describe you?

Similar to “how would your friends describe you”, this question allows one to get clues about whether the candidate fits the company’s culture and value. It also sheds some lights on their work style as the question asks about what their employer would say about them.

2. Who in history would you want to go to dinner with and why?

This question helps one understand where the candidate gets their inspiration from, and what quality in a person they look up to. Their answer may also cover what they want to discuss during dinner, which provides insights into what they are passionate about.

3. Name a brand that represents you as a person.

Other than just asking candidate to describe themselves, use this question to see what personal values they think are important. A family-based brand, for example, probably means they value family or tradition, but of course, the candidate should explain their choice.

4. Please describe an instance where you had to make a decision without all of the necessary information.

This question asks the candidate to showcase their problem-solving skills and past accomplishments, which well-prepared candidates should feel comfortable answering it.

5. Sell me on one idea, and then sell me on the opposite of that idea.

The candidate may or may not have an idea in mind, so be prepared that they may ask the interviewer if he or she has one. Either case, their answer should give insights into whether they can organise their thoughts and present ideas to other people in a convincing way, even when they don’t agree with the sentiment.

6. If a coworker had an annoying habit, and it hindered your quality of work, how would you resolve it?

A chance for the candidate to show how they work on possible conflicts with the rest of the team while maintaining a good relationship.

7. What part of the newspaper do you read first? What does this say about you?

Smart candidates should be able to relate the genre of articles they read to the job they are applying, or the field they want to thrive in.

8. Throw your resume aside and tell me what makes you you.

Another question that allows the interviewer to understand the potential employee better. Candidate should be able to use this opportunity to “sell” themselves, or explain why they are interested in the job or the field.

9. What’s wrong with your past or current employer?

And as you may have already known, speaking ill of an employer is one of the biggest red flags. Some candidates may take this question to explain why they are looking for a new job, which allows you to know better about their expectations.

10. Tell me about the worst manager you ever had.

Again, this is not a question to get the candidate to bad mouth their previous managers, it gives an opportunity for them to explain what type of management style they do not prefer, or how they are able to work with different personality and management styles.

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