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How to answer the 7 most annoying job interview questions (and spot 2 that are illegal to ask)

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You can never be too prepared for a job interview. Doing the all the right things before the big day can still leave room for surprises, especially if your interviewers have a few tricky questions up their sleeves.

While some hiring managers prefer to call them "advanced" interview questions, job candidates view them as "annoying" or "frustrating," often because they are poorly worded, have no right or wrong answer or just seem irrelevant. Whatever the reason, chances are that you'll get caught in one.

Here are seven examples of the most annoying — and commonly asked — interview questions, along with tips on how to answer them with ease and intelligence.

1. "What is your biggest weakness?"

Translation: "How self-aware are you?"
Tip to remember: Never say, "I have no weaknesses." Instead, take one of the hundreds of online assessment tools (i.e., Meyers Briggs or DISC) before your interview. This will help you prepare a fact-based answer.
How to answer: Discuss your profile results (from the personality assessment) with your interviewer. In your answer, explain how you are working to improve yourself based on your innate tendencies. This approach also works well for similar questions about your strengths, giving you the chance to lay out your core skills without sounding like a bragger.

2. "Tell me what you don't like about your current (or previous) manager?"

Translation: "Are you addicted to drama, or can you reasonably work through conflict with a manager?"
Tip to remember: First, rarely is there such a thing as a "perfect manager." Second, never badmouth your previous employer. This is the fastest way to ruin your chances at getting hired.
How to answer: A successful answer requires you to give a critical (yet fair) assessment of how your boss might have made work a little more challenging for you, and how you attempted to find a solution. It's always best to bring up a situation you already discussed with your boss in the past. For example, they might have acknowledged their need to improve their communication skills. And you could say, "We decided that it would help to set up regular check-ins, follow up with email notes from meetings and point out positive interactions."

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3. "Are you planning on having children or getting married?"

Translation: "How much of your time can you commit to the job?"
Tip to remember: These questions are not only tricky, they are also often illegal to ask as part of a hiring assessment. While you shouldn't feel the pressure to answer, it's important to recognize that passing on these types of questions will most likely have a negative impact on your interview.
How to answer: If you choose to answer, of course, be direct and honest. If you choose not to answer, pivot the conversation by saying something concise and straightforward, like "right now, my career is my focus" or "currently, my goal is to pursue an MBA in my free time."

4. "If I ask you to sell me this pen, how would you do it?"

Translation: "How creative and logical are you?"
Tip to remember: Don't try to answer a hypothetical question without facts. Focus on your process instead.
How to answer: These questions are totally subjective, and even the brightest minds often give mediocre answers, so don't set yourself up to fail. Use your experience and expertise to walk the interviewer through your process of approaching the problem. There is no need for any real data here, so try to break the process down into areas such as the objective, target audience details, unique characteristics of the item, competition and delivery method that will resonate best with the consumer. The goal is to demonstrate how thoughtful, creative and process-oriented you are.

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5. "What are your salary expectations?"

Translation: "How well do you know your own industry?"
Tip to remember: Don't base your salary expectations on what you feel you are worth. Use the facts from your research.
How to answer: Instead of trying to put a price on yourself, look up comparable salaries. You can get a pretty good idea of the range by looking through similar job postings, recruitment firm salary guides or websites like Glassdoor. And always answer the question with data: "Based on my research, comparable positions with candidates with a similar background to mine are paying between $50,000 to$60,000, so I would like to be paid in the midpoint of that range."

6. "Tell me about a time you faced an extraordinary challenge. How did you address it?"

Translation: "Do you sink or swim when pushed out of your comfort zone?"
Tip to remember: Anytime a question starts with "tell me about a time," use the S.T.A.R. method to answer.
How to answer: Is there a groundbreaking project you were part of? Have you ever worked with a team with challenging interpersonal dynamics? Break your example down into the following four steps:

  • Situation: Explain when and where did this take place.
  • Task: Share what was your role in this in this example.
  • Action: Share the steps did you took to address the issue.
  • Result: Describe the outcome and what you learned as a result.

7. "Why should we hire you over all the other applicants?"

About the question: "Can you prove that you are the right fit?"
Tip to remember: Never compare yourself to other candidates. Focus on your strengths and how you can compliment a team.
How to answer: Talk about your passion for the role, the alignment of your personal goals with the organizations and how your skills and personal attributes match the job profile and team dynamic. This could also be another great place to highlight your personality assessment. If you genuinely aren't confident in what sets you apart, there are great tools like Strengthfinders that can help draw them out for you.

Not all interviewers are skilled

As challenging as these questions may be, never be sarcastic and avoid cliché humble bragging (i.e., "my biggest weakness is I work too hard"). More importantly, do not let a poor interviewer throw you off by trying to guess the answer they are looking for. The goal is to focus on the facts, your personal values, real experiences, data and personal experience.

Debby Carreau is an entrepreneur, author and founder of Inspired HR. She has been recognized as one of Canada's Top 25 HR Professionals and is a regular contributor on multiple TV shows, Entrepreneur Magazine and many other print and online publications. She is a board member for Young Presidents Organization and Elevation Group as well as an Advisory Board member for FinDev Canada.

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