How to tackle the 5 most difficult job interview questions

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Employers ask tough questions for two reasons – to give them a deeper sense of who you are and to see whether you’re a good fit for the company. These questions can range from solving a problem to trick questions that have no right or wrong answers. More often than not, these are designed to put you on the spot to see how you react.

The first thing to remember when facing hard questions is to stay calm. Try to determine the purpose of the question. For example, if they ask: “Why do you want to work here?” They want to see if you’ve done your research about the company and their company culture. In this case, it will be best to say that you want to work for the company because your values align with the company’s vision, mission and goals, rather than because they have an attractive benefits package or that the office is near your house.

Here are five other tough questions you may encounter in a job interview (and suggested answers):

  1. What is your greatest weakness?

    What they’re trying to find out: The employer would like to know your level of self-awareness and if you’re humble enough to admit your faults. More importantly, they want to know how you handle shortcomings and if you’re proactive about self-improvement.

    How to answer: Be modest, but not too modest. You don’t have to put yourself down. Mention a real weakness that you can easily train for to overcome or one that doesn’t interfere with your ability to do your job. Explain how you are correcting this weakness.

    Sample answer: “I find it hard to provide feedback at work for fear of hurting someone’s feelings. Back in my home country, criticism can be harsh and this is normal. I find that this is not acceptable in the Canadian workplace. This is why I’m training to learn diplomatic and respectful workplace communication so that I can deliver feedback the right way. I realized that by being empathetic, my feedback becomes more helpful for others.”

  2. Why should we hire you?

    What they’re trying to find out: This question is similar to: “What sets you apart from the other candidates?” The employer is looking for added value that makes you unique compared to the other applicants.

    How to answer: Emphasize not only your qualifications and experience but your soft skills as well. Be careful not to sound conceited – it’s easy to say that you are this and that but it will sound hollow without proof. Provide a short and powerful answer that mentions the job’s top requirement and illustrates how you will meet this requirement.

    Sample answer: “Thank you for this question. Based on our discussion today, what you’re looking for is a skilled sales executive who will focus on customer satisfaction to increase sales. At my previous company, I was able to increase sales by 25% by implementing a rewards program that targeted not only our high-end clientele but mid-level customers as well. I will bring the same level of creativity and energy to your company if hired.”

  3. Why do you want to leave your current job? Or Why were you let go in your last job?

    What they’re trying to find out: They want to know if the reason you are leaving (or was let go) is related to your attitude, performance or values. They also want to find out what you are looking for in a position or workplace.

    How to answer: If you’re trying to leave a toxic work environment, resist the temptation to badmouth your current employer. This is unprofessional. Instead, focus on the idea that you’re taking advantage of a better job opportunity. If you were laid off or fired, don’t worry. This is not uncommon during the pandemic. Emphasize your past accomplishments and the measures you have taken after being out of work.

    Sample answer: “I loved working at XYZ Company. Unfortunately, their biggest client had to close its business last year at the height of the pandemic. This had a major effect on revenues and they had to downsize. I was one of their most recent hires so I was among those who were let go. I was proud of the work I did there even if it was a short stint. My former manager is one of my strongest references.”

  4. What is your expected salary?

    What they’re trying to find out: Employers might ask this to see if you know the industry-standard rates for your job and position, or if you know your worth. However, some (bad) employers might be checking if they can get away with a lower salary or they just want to know if they can afford you before they spend more time and resources convincing you to work for them.

    How to answer: This is a tricky question especially if the salary range for the position is not specified in the job ad (this is a red flag). You can respectfully refuse to answer the question especially if it is only the preliminary interview. You might say “I’ll be happy to discuss this when I know more about the responsibilities of this job and your expectations.” You can also say that you decide based on the entire compensation package, not only the salary. This will require them to tell you more about the job’s benefits. In any case, it will be to your advantage if you know the current standard salary range for your position, so do your research (use Canada Job Bank).

    Sample answers: “I’m more interested in knowing about how this job is a good fit for my skills and interests. I’m sure that you’ll be offering a reasonable salary that’s not only competitive in the current market but also commensurate to my skills and experience.”


    “While I am flexible, I’ll have to say that $XX to $XX is the right range based on the responsibilities of this position. There’s a lot to take on and I’m confident that I can deliver the results you’re looking for.”

  5. If you were a tree, what kind would you be and why? (and other off beat questions)

    What they’re trying to find out: Employers ask this question either to help you relax or to test your reasoning skills. A variation would be questions like “how many pennies would fit in this room?” (an interview question for a product analyst position). The candidate is expected to use logic to explain how they would go about solving such problems.

    How to answer: This may catch you off guard but take it seriously. Do your best to provide a good response that shows your analytical as well as creative skills (as appropriate). It may even be a chance to show your humour – just remember to keep it professional.

    Sample answer: “I would probably be a willow tree because I’m tenacious and strong. And just like the willow tree is able to thrive in a wide range of soil and moisture conditions, I can also easily adapt and grow in various work environments.”

    Sources: Tough job interview questions and the best answers, Alison Doyle, the balance careers; 10 unexpected interview questions to get unrehearsed answers, Gregory Lewis, LinkedIn Talent Blog; How to answer: Why did you leave your last job? Pamela Skillings, Big interview; and 15 fun, weird, and unexpected interview questions (with sample answers), Caroline Forsey, Hubspot. Accessed February 11, 2021.

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