The Most Difficult Question in a Job Interview: Ranking the Ultimate Challenge

Choose the question you think is the most difficult!

Author: Gregor Krambs
Updated on Apr 15, 2024 06:40
Welcome to StrawPoll, where your opinion matters! Do you break into a cold sweat when faced with a difficult job interview question? Well, you're not alone! We've compiled a nail-biting ranking of the most challenging questions candidates face during interviews, and now it's your turn to vote! Help us determine the toughest question that leaves even the most seasoned professionals stumped. Explore our list, cast your vote, and if you think we missed a truly nerve-wracking question, feel free to suggest it! Let's conquer these interview curveballs together and share our collective wisdom. Ready to dive in? Click here to join the great debate and let your voice be heard!

What Is the Most Difficult Question in a Job Interview?

  1. 1
    This question is difficult because it requires honesty and self-reflection. It's important to be honest about weaknesses, but also to show how you are working to improve them.
    The 'What is your biggest weakness?' question is a commonly asked interview question intended to assess a candidate's self-awareness, honesty, and ability to reflect on their areas for improvement. It aims to reveal how well a candidate can identify and address their weaknesses, as well as their willingness to learn and develop.
    • Question type: Behavioral
    • Purpose: Assess self-awareness, honesty, and willingness to improve
    • Expected answer: Acknowledge a genuine weakness and provide details on improvement efforts
    • Avoided answers: Insincerity, unrelated strengths disguised as weaknesses
    • Follow-up questions: Request for specific examples, strategies for improvement
    What is your biggest weakness? in other rankings
  2. 2
    This question is difficult because it requires a strong understanding of the company and its needs, as well as a clear demonstration of how your skills and experience can benefit the organization.
    The 'Why should we hire you?' question is a commonly asked question in job interviews where the interviewer wants to assess why the candidate is the best fit for the role and what unique qualities they bring to the table.
    • Purpose: To evaluate the candidate's self-awareness, confidence, and ability to explain how their skills and experiences make them the ideal candidate for the job.
    • Assessment: Evaluate the candidate's understanding of the job requirements, industry knowledge, and ability to align their qualifications with the company's needs.
    • Expected Response: A well-prepared response that highlights the candidate's relevant skills, experiences, accomplishments, and their alignment with the job description.
    • Effective Strategies: Identifying the employer's pain points and addressing how the candidate can solve them, providing specific examples of achievements, and showcasing enthusiasm for the role.
    • Key Points: Demonstrate a clear understanding of the company's mission and values, emphasize how the candidate's unique qualities and experiences align with the company culture.
    Why should we hire you? in other rankings
  3. 3
    This question is difficult because it requires vulnerability and the ability to turn a negative experience into a learning opportunity. It's important to be honest about the failure, but also to show how you bounced back and what you learned from the experience.
    The 'Tell me about a time when you failed' interview question is designed to assess a candidate's ability to handle failure and learn from their mistakes. It allows the interviewer to gauge the candidate's self-awareness and problem-solving skills.
    • Question Type: Behavioral
    • Purpose: To evaluate how the candidate handles failure and learns from their mistakes
    • Assessed Skills: Self-awareness, problem-solving, resilience
    • Expected Response Format: Using the STAR method (Situation, Task, Action, Result), describing the failure, the lessons learned, and how they applied those lessons moving forward
    • Expected Content: Clear description of the failure, explanation of the candidate's role in the failure, analysis of lessons learned, and demonstration of growth or improvement
    Tell me about a time when you failed. in other rankings
  4. 4
    This question is difficult because it requires strong communication skills and the ability to navigate difficult situations. It's important to demonstrate a willingness to listen and compromise, while also standing up for what you believe in.
    The question 'How do you handle conflict?' is often considered as one of the most difficult questions in a job interview. It aims to gauge how a candidate deals with disagreements or conflicts in the workplace environment. The interviewer wants to understand the candidate's ability to handle challenging situations, resolve conflicts, and maintain positive relationships with colleagues and team members.
    • Purpose: Assess candidate's conflict resolution skills and ability to maintain positive working relationships
    • Difficulty Level: Moderate to high
    • Expected Response Format: Structured answer with specific examples
    • Key Skills Assessed: Conflict resolution, communication, problem-solving, emotional intelligence
    • Desired Traits: Ability to remain calm under pressure, active listening, empathy
  5. 5
    This question is difficult because it requires knowledge of industry standards and a balance between being realistic and not undervaluing yourself. It's important to do research beforehand and have a clear idea of what you are willing to accept.
    The question 'What are your salary expectations?' is considered one of the most difficult questions in a job interview. It puts the candidate in a challenging position as it requires them to strike a delicate balance between stating their worth and not pricing themselves out of the job market. This question aims to determine if the candidate's salary expectations align with the company's budget and compensation structure.
    • Purpose: To assess whether the candidate's salary expectations align with the company's budget and compensation structure.
    • Difficulty level: High
    • Psychological impact: High, as it requires the candidate to negotiate their worth while not appearing too demanding or underestimating their value.
    • Evaluation criteria: Candidates' ability to research the salary range for similar roles, their negotiation skills, and alignment of expectations with the company's compensation structure.
    • Company motivation: To ensure they can afford the candidate and that the candidate's expectations align with the company's budget.
  6. 6
    This question is difficult because it requires the ability to stay calm and focused in challenging situations. It's important to show examples of how you have handled pressure in the past and what techniques you use to manage stress.
    The question "How do you handle pressure?" is a common and important question in job interviews. It is designed to assess how a candidate handles stressful situations and their ability to remain composed and productive under pressure.
    • Purpose: Assess candidate's ability to handle stress and pressure
    • Evaluation: Based on the candidate's response and examples provided
    • Relevance: Applicable to roles that involve tight deadlines, high-stress environments, or frequent multitasking
    • Insights: Gives insights into a candidate's problem-solving skills, resilience, ability to prioritize, and communication under pressure
    • Expected response: Candidate should describe their coping mechanisms, strategies for staying calm, and providing examples of how they successfully handled pressure in the past
  7. 7
    This question is difficult because it requires self-awareness and honesty about what drives you. It's important to show passion for the job and a desire to learn and grow within the organization.
    The 'What motivates you?' interview question is designed to understand what drives an individual to perform well and stay committed in a work environment. It seeks to uncover the candidate's personal and professional interests, goals, values, and their ability to self-motivate.
    • Question Type: Open-ended, behavioral question
    • Purpose: To assess the candidate's self-awareness, passion, and alignment with the company's values
    • Response Length: Varies, but usually requires a thoughtful and well-articulated response
    • Expected Skills: Ability to introspect, articulate personal and professional motivations, and connect them with the job at hand
    • Evaluation Criteria: Relevance, authenticity, clarity, coherence, and enthusiasm in the response
    What motivates you? in other rankings
  8. 8
    This question is difficult because it requires the ability to accept feedback and use it to improve. It's important to show a willingness to learn and adapt, while also being confident in your abilities.
    The 'How do you handle constructive criticism?' interview question assesses a candidate's ability to receive and respond positively to feedback in a professional setting. It evaluates their willingness to learn from others, adapt to new ideas, and improve their work performance.
    • Question Type: Behavioral
    • Purpose: Assess candidate's ability to handle feedback
    • Skills Assessed: Receptiveness to feedback, adaptability, willingness to learn
    • Expected Response: Acknowledgment of the importance of feedback, openness to criticism, ability to provide examples of situations where feedback led to personal/professional growth
    • Desired Qualities: Reflectiveness, humility, self-awareness
    How do you handle constructive criticism? in other rankings
  9. 9
    This question is difficult because it requires the ability to weigh pros and cons and make a decision based on limited information. It's important to show how you gathered information and sought advice, while also taking responsibility for the outcome.
    The question 'Tell me about a time when you had to make a difficult decision' is commonly asked in job interviews to assess a candidate's problem-solving skills and decision-making abilities in challenging situations.
    • Purpose: To evaluate the candidate's ability to think critically, assess risks and consequences, and make well-informed decisions.
    • Typical response length: 1-3 minutes
    • Preferred format: Briefly describe the context, outline the decision you had to make, explain the factors considered, discuss the actions taken, and conclude with the outcome and any lessons learned.
    • Key factors assessed: Problem-solving skills, critical thinking, decision-making abilities, communication skills, leadership potential, ability to handle pressure and difficult situations.
    • Desired qualities in the response: Clear explanation of the problem, logical thought process, consideration of different perspectives, weighing pros and cons, displaying accountability for the decision, showcasing learned lessons and personal growth.
  10. 10
    This question is difficult because it requires a clear understanding of your career aspirations and how they align with the company's mission and values. It's important to show ambition and a desire for growth, while also being realistic and adaptable.
    The question 'What are your long-term career goals?' is commonly regarded as one of the most difficult interview questions. It is designed to assess a candidate's vision, ambition, and alignment with the organization's long-term objectives.
    • Purpose: Assessing a candidate's career aspirations and determining if they align with the organization's objectives
    • Difficulty: Considered difficult due to its open-ended nature and the need for alignment with the company's long-term goals
    • Insightfulness: Reveals a candidate's ambition, motivation, and ability to plan for the future
    • Evaluation Criteria: Candidates' clarity, realistic goals, ambitiousness, alignment with the organization, and ability to articulate their vision
    • Relevance: Determines if a candidate's long-term goals are in line with the position and potential growth opportunities
    What are your long-term career goals? in other rankings

Missing your favorite question?


Ranking factors for difficult question

  1. Relevance
    The question should be relevant to the job role and assess the candidate's skills, knowledge, or experience necessary for success in that role.
  2. Complexity
    Difficult questions can be complex, requiring the candidate to think critically, analyze information, and provide a well-structured response.
  3. Ambiguity
    Some difficult questions may have open-ended or multiple correct answers, requiring the candidate to come up with a solution that best fits the given context.
  4. Problem-solving
    Questions that require the candidate to think strategically and come up with an innovative solution to a problem can be particularly tough.
  5. Behavioral and situational
    Difficult questions often revolve around past experiences or hypothetical scenarios to assess the candidate's character, emotional intelligence, and ability to navigate interpersonal conflicts.
  6. Technical expertise
    Depending on the job role, difficult questions may require candidates to demonstrate their technical knowledge, programming skills, or understanding of a specific subject matter.
  7. Time-sensitive
    Some challenging questions may require candidates to give a response quickly, testing their ability to assess and react in a limited amount of time.
  8. Cognitive ability
    Questions that test a candidate's cognitive abilities, such as pattern recognition, logical reasoning, and decision-making, can be particularly difficult.
  9. Unfamiliarity
    A difficult question may involve a concept, tool, or scenario that is unfamiliar to the candidate, challenging them to think creatively and adapt their existing knowledge.

About this ranking

This is a community-based ranking of the most difficult question in a job interview. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or question is missing, feel free to help improve the ranking!


  • 187 votes
  • 10 ranked items

Voting Rules

A participant may cast an up or down vote for each question once every 24 hours. The rank of each question is then calculated from the weighted sum of all up and down votes.

More information on most difficult question in a job interview

The job interview process can be a nerve-wracking experience for many job seekers. It's a chance to showcase skills, experience and personality traits to a potential employer while also trying to make a good first impression. One of the most challenging aspects of the interview is answering difficult questions that may catch you off guard. These questions are designed to test your critical thinking skills, problem-solving abilities, and decision-making capabilities. One of the most difficult questions in a job interview is the infamous "Tell me about yourself." This question seems simple at first, but it can be challenging to answer. It's difficult to know how much personal information to include without oversharing, and how much professional information to provide without sounding like you're reading off your resume. Other difficult questions can include "What is your greatest weakness?" and "Why should we hire you?" These questions require a delicate balance of honesty and confidence to answer effectively. Overall, job interview questions are designed to assess a candidate's suitability for the role and to ensure they will be a good fit for the company culture.

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