How to Answer the 5 Most Difficult Interview Questions

cat nervous and looking to the side

Landing an interview is the first step to launching your remote career, but prepping properly for an interview is critical to securing any position.

It’s likely you’ve participated in an interview in the past, so you know that the interviewer is probably going to throw some challenging questions your way.

Knowing the reasoning behind each question can be useful in your preparations and help you best answer the most difficult interview questions.

Here’s how to answer the five most difficult interview questions:

1. What’s your biggest weakness?

What the Employer Really Wants to Know

  • Which of your skills require further training?
  • Are you self-aware enough to see your areas of strength and the areas needing improvement?
  • Are you able to assess yourself, and are you open to constructive criticism?

How to Answer This Question

  • Take a hard look at your weaknesses with a critical eye.
  • Share one weakness with the interviewer, and show them how you plan to fill that gap.
  • Give at least two examples of how you can strengthen this weakness with further training, continuing education, or by how you’ve corrected the issue through experience.

2. Where do you see yourself in five years?

What the Employer Really Wants to Know

  • Does this job follow your intended career trajectory?
  • Have you considered your career long-term?
  • Are you viewing this position as a stepping-stone?

How to Answer This Question

  • Share with the interviewer that you’ve taken a career assessment test and proactively completed career planning or coaching.
  • After researching the company prior to the interview, share what you’ve learned about the company and how you would fit to help the company grow or excel.
  • Explain how you plan to develop professionally and the additional responsibilities you see yourself shouldering.
  • Avoid saying inappropriate things, like “I have no idea,” or “I haven’t thought that far ahead,” or “I want your job.”

3. Why did you leave your last position?

What the Employer Really Wants to Know

  • Did you leave on good terms?
  • Did you leave on your own accord or was it a company layoff or firing?
  • Will you say negative things about your former employer?

How to Answer This Question

  • Were you fired? No matter what the circumstance of the firing, avoid talking poorly about your former employer. Tell the interviewer that you were let go, explain that you understand the logic behind the action, and convey that you now recognize areas for improvement. Then, tell them why you’re a “new and improved” version of yourself because of this experience.
  • Were you laid off? Here’s another instance when badmouthing a former employer will likely be a detriment to you. Tell the interviewer that there were layoffs at the time that were outside the employees’ control and that you’re ready to apply your job skills to this new company.
  • Did you quit? Although it may be tempting, don’t express your feelings about your former employer. Instead, focus on the positive experiences you had with that employer. Mention that you felt that the time had come to seek a new opportunity that will allow you to expand your career growth and potential.

4. Why should we hire you?

What the Employer Really Wants to Know

  • Are you objective about your skills and accomplishments?
  • Can you eloquently describe your achievements?
  • Are you qualified for the position?

How to Answer This Question

  • Prepare for this question by listing your past accomplishments at work, as well as your most refined skills.
  • Select three or four accomplishments from the list you’ve created to use during your interview. Be sure the accomplishments selected are relevant to the position you’re interviewing for to show that you’re qualified for the role.
  • Don’t forget to feature any skills or accomplishments that reflect your management style, teamwork abilities, and/or your enthusiasm for your chosen field.
  • Be sure to highlight your self-motivation and ability to meet deadlines when interviewing for remote positions.

5. What are your salary requirements?

What the Employer Really Wants to Know

  • Are you realistic about the career level you’re at?
  • Are your expectations too high for this role?
  • Were you paid more in previous positions?

How to Answer This Question

  • Prior to the interview, prepare to answer this question. Use resources such as Glassdoor, PayScale, and Salary.com to get a well-defined, reasonable salary range for this role.
  • Be sure that you’re factoring in your experience and education into that salary range, and consider your geographical location, as this can impact salary.
  • Respond thoughtfully by offering a salary range, and explain that you’re open to discussing this further, or factor in good benefits as part of the whole package.
  • Be pointed in your response, and calmly wait in silence once you’ve expressed your salary expectations. This is the first step to successful negotiating.
Written By: Brie Reynolds