Better Guide to Challenging Interview Questions

Whether you’re an experienced professional or a fresher, you will undoubtedly face challenging interview questions. And these questions require thorough and thoughtful answers.

After working so hard to refine your CV, polish your cover letter, and get the big job interview, you don’t want to mess up.

You should prepare in advance since competent hiring managers use difficult interview questions to narrow down their pool of potential hires. This article discusses some difficult interview questions focused on your skills, experience, and the job position.

Challenging Interview Questions to Prepare Better

Every time you go on an interview for a new job, you will be asked some challenging questions. Even though you can’t predict which difficult questions will be asked, there are a few likely options. It’s a good idea to practice complex question responses while preparing for interviews. Check out some common challenging interview questions below.

Colleagues and Supervisors Related Questions

To gauge how well you will fit in with a particular group, interviewers will inquire about your interactions with your managers and coworkers.

Below are some common questions you can expect:

  • Describe a situation where you had to deal with a coworker who wasn’t contributing their fair share of the job. How did you react to the situation?
  • Describe a time when you took the initiative to let others know about a coworker or supervisor’s accomplishments.
  • Tell me about an instance when you didn’t get along with a manager.
  • Describe an occasion when you helped someone.
  • How well do you get along with your coworkers, regardless of age?
  • Describe a time when you misjudged in your assessment of a person.
  • Have you ever had to work with someone you disliked? If so, what were your strategies?

Response Tips:

Aim to be positive when responding to questions regarding your bosses. Even if you had a difficult or frustrating supervisor or coworker, you’d want to avoid negative remarks, personal insults, or complaints.

Skills Related Questions

During your interview, the hiring manager will evaluate your skills to assess how efficient you might be in the position you’re seeking. It would be beneficial if you considered specific examples of successful outcomes from prior employment.

Below are a few examples of skills-based questions:

  • Describe a choice you made that you regret. What happened and why?
  • Why do you think you’ll be successful in this position?
  • Describe a situation when you had to explain technical material to non-technical people.
  • Tell me about an instance when your priorities clashed. How did you decide what was most important?
  • Tell me about a task where you had to analyze and present data.
  • Describe a time when you were a member of a team. What was your responsibility, and how successfully do you think you carried it out?
  • Describe an occasion when you failed. How did you respond to it?

Response Tips:

When asked about your skills, emphasize your most applicable hard and soft skills. Know that both of these skills matter. This job description and the interview itself may provide hints about what managers will value most for this position.

Questions About Your Career Goals

For career-related questions, you should convey your drive for the future and emphasize your enthusiasm for learning and progressing in the opportunity.

The interviewer could begin with your college graduation and ask you to discuss the reasons for your career decisions. They might also ask you to describe the thought processes behind each choice you made.

Below are some common questions for career goals and work ethics:

  • How many hours a day or week would you work to get the job done?
  • What would you want to do next if you continued working with your current employer?
  • How do you measure or evaluate success?
  • What would be your dream job?
  • What type of job or work would be your worst nightmare?
  • How do you react to projects with tight deadlines?
  • What would be your top two priorities if you were the CEO of this organization?

Response Tips:

These types of questions require self-knowledge and planning ahead.

It is relatively simple to answer questions about career goals if you have already thought about your long-term professional objectives. But it can be difficult to respond if you’ve never thought about the position you want to be in a few years.

Try focusing first on your immediate objectives before looking further into the future. You can concentrate on the actions you’ll take to achieve your long-term goals.

Questions About Working With Others

Every job demands you to interact with coworkers. And how well you do it will impact how everyone feels about their workplace. Interviewers will ask you a series of questions to test your interpersonal skills.

Below are some example questions you can expect:

  • What methods have you employed to encourage subordinates to boost their performance?
  • Can you facilitate group conversations in a way that includes diverse points of view and encourages consensus?
  • Have you ever designed and presented training programs that encourage audience performance?
  • How would you deliver difficult news to a colleague targeted for layoff?
  • How well do you get along with clients and figure out their preferences for products and services?
  • Are you able to patiently address consumer complaints?
  • Do you actively and sympathetically listen when clients speak out about their concerns and sentiments?
  • Tell me about a time when you resolved a client or employee dispute.

Response Tips:

Working with others is necessary for every job, whether with clients or coworkers. Consider using examples from prior professional experience in your response. You can use this chance to talk about your interpersonal and communication skills.


You’re bound to face challenging questions at interviews. Well, that’s what an interview is all about. Besides the simplest questions, you’ll also get some difficult questions thrown your way to test your skills.

Don’t fret! The key is to prepare yourself ahead of time to get ready for any challenging situation. This article lists some difficult interview questions that require proper thought and understanding. Start preparing now!

Abir is a data analyst and researcher. Among her interests are artificial intelligence, machine learning, and natural language processing. As a humanitarian and educator, she actively supports women in tech and promotes diversity.

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