How To Answer the Most Awkward Interview Questions Like a Pro


It’s no secret that competing for a job is tough, and always has been.

Employers often have to choose between multiple applications to select a single candidate for one position. Applicants are usually screened pretty carefully, and for those who make it to the interview stage, you can look forward to the interviewer asking difficult and slightly awkward questions that are designed to shed light on the candidate’s true capabilities.

So without further ado, here are five awkward questions that might come up in your next interview, along with strategies to help you sidestep the awkwardness and answer them in a positive way:

1. Why are you leaving your current job?

This is a valid question that every interviewer is likely to ask, and depending on your situation, your answers will vary. Outlined below are four different situations and their respective answers.

  • If you were part of a job cutback, don’t be ashamed to explain that you were let go because of downsizing. Young professionals are often anxious to discuss this topic in an interview, because they worry that it might make them look like an unsuccessful candidate. However, it’s always better to tell the truth in an interview, and this scenario doesn’t mean that you were a bad employee— it was just bad timing. Make sure you make it clear that you were let go because of the company’s needs, and not any indiscretion on your part!
  • If you were fired, it’s best to say that you parted ways. After the the initial question is answered, steer the discussion towards how your skill set matches the current position you are interviewing for. Whatever you do, don’t bad mouth your previous employer— this will just reflect poorly on you and will make your interviewer doubt your company loyalty.
  • If you do have a job, focus on why you’re seeking greater challenges than those currently available at your present position. Focus on the responsibilities you’ve been given at your current job and why you are ready to go beyond them.
  • If you’re switching to a new industry, talk about how you made the career transition and tie it into the new job’s responsibilities. Make sure that you discuss the relevant qualifications you have that will help you succeed in this new field, and discuss your passion for the new industry to show the interviewer how serious you are about making a successful transition.

All in all, make sure that you are confident in your response and always turn the conversation back to the job you are applying for, as well as the relevant skills, experience, and enthusiasm you’ll bring to the role.

2. Why shouldn’t we hire you?

This is a scary trick question that would make any applicant nervous if they are not properly prepared. And no, you can’t answer, “Because I’m too perfect and detail-oriented.” The interviewer could be asking you this question to hear about your weaknesses, or they could be asking the standard “Why should we hire you?” with a twist. Either way, it’s best to respond by focusing on your strengths rather than your weaknesses. While you don’t want to come across with an answer that paints you in an unrealistic light, you do want to make sure to tailor your answers to your personality, background and your needs as a worker.

For example, you might say:

  • You shouldn’t hire me if you like your team to require a lot of hand-holding and micro-management. I can take direction and turn it into an action quickly.
  • You shouldn’t hire me if you want employees who need a lot of training to be effective in this role. Based on how you’ve described the position, I know I could hit the ground running as a member of your organization.

3. Where do you see yourself in five years?

This is a common question that recent grads will receive because interviewers are curious about your interest in their company. A good game plan for answering this question is to talk about what experiences initially motivated you to apply for this job and what you hope to achieve in the role, should you be hired. However, beware of saying that you aim to be the CEO of the company or get the interviewer’s job, since you may come off as arrogant. Instead, discuss how you’d like to work your way up to a leadership role. Keep the conversation focused on what professional skills and tasks you hope to accomplish as part of the company.

4. Why should we hire you and not another applicant?

When answering this question, remember to be gracious and respectful of your competition as well as to upsell yourself in powerful way, promoting your experiences and skills. After all, the interviewer is asking you this question to see if you’re truly ready for the job and it’s up to you to demonstrate that you are more willing than any other candidate to excel in the role. In order to show that you are ready, describe your career progression and how your past achievements would make you a valuable asset to the company.

5. Why is there a gap in your work history?

Although you may have a gap in your work history, it doesn’t mean that you haven’t been busy.

Tell the interviewer what you’ve been doing during your unemployment period. Specifically mention any freelance projects you’ve worked on, if you’ve taken care of family members, took time off to study, or completed a volunteer project. Ultimately, you want to show your interviewer that you have been productive during your time off.

Sometimes, interviewers will ask us questions that are a bit awkward to answer. Although it’s tricky, they are intentionally trying to throw you a curveball to see how you respond under pressure. Nevertheless, remember to stay confident and answer as eloquently as possible with these strategies in mind. Good luck with the job hunt!