The Most Difficult Interview Question: Uncovering the Ultimate Challenge

Choose the interview question you think is the most difficult!

Author: Gregor Krambs
Updated on Mar 4, 2024 05:38
Welcome to StrawPoll, where your opinions matter! Ever been stumped in an interview? We've all been there, and we want to know which question left you scratching your head the most. Dive into our interactive ranking of "What is the most difficult interview question?" and cast your vote for the question that had you sweating bullets. Don't see the brain-busting inquiry that haunted your dreams? No problem! Go ahead and suggest your own nightmare-inducing interview question to add to the ranking. Join the conversation, compare notes, and discover if others have faced the same interview hurdles as you. Challenge yourself and find out if you've got what it takes to handle the most difficult interview questions like a pro!

What Is the Most Difficult Interview Question?

  1. 1
    This question can be difficult because it requires you to be honest about your shortcomings while also demonstrating self-awareness and a willingness to improve.
    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 can be tricky because it requires you to sell yourself and articulate your unique qualifications and strengths in a way that sets you apart from other candidates.
    The 'Why should we hire you over other candidates?' interview question is a commonly asked question during job interviews. It aims to evaluate how confident and well-prepared a candidate is in selling themselves and highlighting their unique strengths and qualities. Employers use this question to assess a candidate's self-awareness, ability to differentiate themselves from others, and their understanding of the job requirements and company culture.
    • Purpose: Assess candidate's competitiveness and ability to articulate their value
    • Evaluation Criteria: Relevance to job requirements, unique strengths, skills, experience, personality fit
    • Confidence: Measure candidate's self-assurance and persuasive skills
    • Differentiation: Evaluate candidate's ability to stand out from other potential candidates
    • Communication Skills: Assess candidate's ability to articulate their unique value proposition verbally
  3. 3
    This question can be challenging because it requires you to admit to a mistake or failure and then explain how you learned from it and grew as a result.
    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 can be difficult because it requires you to negotiate your worth and come up with a figure that is reasonable and competitive, without pricing yourself out of the job.
    The question 'What is your salary expectation?' is one of the most difficult interview questions as it directly relates to the compensation the candidate is seeking for the position they are applying for. It requires careful consideration and negotiation skills to provide a suitable response.
    • Purpose: To gauge candidate's salary expectations and negotiate a suitable compensation package.
    • Difficulty level: High
    • Relevance: Critical to assess candidate's financial expectations and alignment with the company's budget.
    • Negotiation skills: Requires strong negotiation skills to provide a reasonable salary expectation while considering the market value for the position.
    • Research: Candidates should conduct research on industry standards, position requirements, and the company's financial capabilities to formulate a well-informed response.
  5. 5
    This question can be tricky because it requires you to demonstrate your conflict resolution skills and your ability to work well with others, even in challenging situations.
    The question 'How do you handle conflict with coworkers or supervisors?' is a common and challenging interview question. It aims to assess your interpersonal skills, conflict resolution abilities, and professionalism in a work setting. The question evaluates how well you can handle difficult situations and maintain positive relationships with your colleagues and superiors.
    • Relevance: This question evaluates your ability to handle conflicts in a professional environment.
    • Assessment: It assesses your interpersonal skills, conflict resolution abilities, and professionalism.
    • Problem-solving: It examines how well you can address conflicts and find effective solutions.
    • Communication: It tests your communication skills and the ability to express yourself clearly and diplomatically.
    • Emotional intelligence: It measures your emotional intelligence in dealing with workplace conflicts.
  6. 6
    This question can be difficult because it requires you to explain why you left your previous position without sounding negative or critical of your former employer.
    The question, 'Why did you leave your last job?' is one of the most difficult interview questions to answer as it requires the interviewee to delicately balance honesty and diplomacy. This question aims to assess the candidate's reasons for leaving their previous employment, their level of professionalism in handling job transitions, and their ability to reflect on their career choices.
    • Purpose: To understand the motives behind leaving the previous job.
    • Assessment: Evaluate the candidate's professionalism, self-awareness, and potential cultural fit.
    • Complexity: Moderate to high, as the candidate needs to discuss any negative aspects without portraying themselves negatively.
    • Introspection: Requires self-reflection and analysis of personal and professional growth.
    • Diplomacy: Reveals the candidate's ability to discuss sensitive topics with tact and without blame.
    Why did you leave your last job? in other rankings
  7. 7
    This question can be challenging because it requires you to articulate your aspirations and ambitions in a way that aligns with the company's mission and values.
    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
  8. 8
    This question can be tricky because it requires you to reflect on your personal values and drivers, and then explain how those factors contribute to your work ethic and performance.
    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
  9. 9
    This question can be difficult because it requires you to demonstrate your coping mechanisms and stress management strategies, while also showing that you can handle pressure and tight deadlines.
    The 'How do you handle stress?' interview question is designed to assess how well a candidate manages and copes with stressful situations in the workplace. Interviewers ask this question to evaluate a candidate's ability to handle pressure, stay focused, and make rational decisions under stress.
    • Assessment of coping mechanisms: Evaluates the candidate's ability to manage stress and their strategies for dealing with it
    • Problem-solving skills: Assesses how the candidate approaches challenges and finds solutions under pressure
    • Emotional intelligence: Determines if the candidate can regulate their emotions and maintain composure during stressful situations
    • Communication skills: Evaluates the candidate's ability to effectively communicate and collaborate with others when facing stress
    • Adaptability: Assesses the candidate's capacity to adapt and adjust to changing circumstances and unexpected stressors
    How do you handle stress? in other rankings
  10. 10
    This question can be challenging because it requires you to be honest about areas where you may struggle or need improvement when working with others, while also demonstrating a willingness to collaborate and learn from others.
    The question 'What are your weaknesses as a team player?' is a commonly asked interview question that aims to assess a candidate's self-awareness, ability to reflect on their own performance, and willingness to improve in a team environment. It allows the interviewer to gauge how well the candidate understands their strengths and limitations as a team player.
    • Question Type: Open-ended
    • Purpose: Assessing candidate's self-awareness, reflection, and willingness to improve in a team
    • Expected Response: Honest acknowledgment of weaknesses followed by steps taken to address and improve them
    • Challenges: Candidates may struggle to identify genuine weaknesses or may provide generic or insincere responses
    • Evaluation Criteria: Self-awareness, ability to reflect on own performance, understanding of teamwork dynamics, commitment to personal growth

Missing your favorite interview question?


Ranking factors for difficult interview question

  1. Ambiguity
    A difficult interview question may be vague or open to various interpretations, demanding a more thoughtful and elaborate response from the candidate. Ambiguity can make it harder for the candidate to pinpoint the exact answer the interviewer is looking for.
  2. Emotional Intelligence
    Some interview questions are designed to evaluate the emotional intelligence of the candidate. These questions can be difficult to answer, as they often require self-awareness and introspection.
  3. Problem-solving and critical thinking
    Difficult interview questions may involve unique or complex situations that require problem-solving and critical-thinking skills. The candidate must analyze the given information, evaluate possible solutions, and formulate a coherent response.
  4. Creativity
    Challenging interview questions may also assess the candidate's creativity and ability to think outside the box. These questions typically do not have a single correct answer and require the candidate to come up with an original response.
  5. Personal experience
    Some difficult questions require the candidate to draw from their own personal experiences, such as discussing a professional failure, resolving a conflict, or making a tough decision. These questions can be uncomfortable or challenging, as they require self-reflection and honesty.
  6. Time-constrained responses
    An interview question may become more difficult if the candidate is given limited time to formulate their response. This tests the candidate’s ability to think on their feet and deliver an effective response under pressure.
  7. Unconventional format
    Difficult questions may also be presented in an unconventional format, such as a hypothetical scenario or a brain teaser. These questions can be challenging as they require a different thought process than traditional interview questions.
  8. Technical complexity
    In certain industries, interview questions may involve highly technical concepts or subject-specific knowledge. The candidate must demonstrate their understanding and expertise in these areas to answer the question effectively.
  9. Level of preparation
    The difficulty of an interview question can also be influenced by the level of preparation the candidate has undertaken before the interview. A well-prepared candidate will be better equipped to handle challenging questions than someone who has not done their homework.

About this ranking

This is a community-based ranking of the most difficult interview question. 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!


  • 182 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.

Trendings topics

Don't miss out on the currently trending topics of StrawPoll Rankings!

More information on most difficult interview question

Background Information: The Most Difficult Interview Questions Job interviews can be nerve-wracking, especially when the interviewer asks a difficult question. These questions are designed to test a candidate’s problem-solving skills, critical thinking abilities, and ability to handle pressure. While some questions are straightforward, others can leave candidates completely stumped. So, what are the most difficult interview questions? There are a few that come up time and time again: 1. "Tell me about yourself." This question may seem simple, but it can be difficult to know where to start. Candidates may struggle to strike the right balance between being confident and humble, while also highlighting their relevant experience. 2. "What is your greatest weakness?" This question is a classic, and it’s one that most candidates dread. It can be difficult to admit to a weakness, while also demonstrating how you’re working to improve it. 3. "Why should we hire you?" This question requires candidates to sell themselves and articulate exactly what they can bring to the role. It can be tough to strike the right balance between being confident and coming across as arrogant. 4. "How do you handle stress?" This question is designed to test a candidate’s resilience and ability to cope under pressure. It can be difficult to give a clear answer without appearing flustered. Overall, the most difficult interview questions are those that require candidates to think on their feet and demonstrate their skills and experience. By preparing in advance and practicing your answers, you can increase your chances of success in any interview.

Share this article