The most difficult interview questions (and answers) (2024)

You reworked your resume, perfected your cover letter, and landed the big job interview. But walking through the door is only the beginning. You know the person across the table from you will ask some difficult interview questions. If you don’t know how to respond, consider yourself toast.

Smart hiring managers ask tough interview questions to whittle down their pool of potential hires, which is why it’s important for you to prepare in advance. Start with these.

1. What is your greatest weakness?

Strengths-and-weaknesses interview questions are a given. You’ll want to use some care when choosing your answering the greatest weakness portion. “So many articles say that you should make your biggest weakness a positive attribute, which is not something I recommend doing,” says Brenda Abdilla, a Denver-based career and leadership coach. “This is not an opportunity to humblebrag.”

At the same time, “you want to be real and truthful about an area of development you truly need, but you want to avoid sharing something that’s serious and going to raise a red flag that you’re not a suitable candidate,” cautions Kathy Caprino, a Connecticut-based career coach and author of the book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss.

No matter what your answer is, make sure you impress upon the hiring manager that you're taking steps to improve.

Bad answers:

  • “I’m late all the time.”
  • “I’ve been fired before.”
  • “I find it hard to work with really opinionated people.”

Great answers:

  • “My analytical skills are very strong and I’m extremely comfortable with numbers, but I’m working on enhancing my writing skills.”
  • “In the past, I’ve taken on a bit more than I can chew, so I’m honing my ability to manage my time better and making sure I understand what’s involved in extra tasks I say ‘yes’ to.”

2. Why should we hire you?

Don't let difficult interview questions such as this one psych you out. Job search strategist Jenny Foss says the best way to craft an answer to this question is to determine what sets you apart from your competition.

Tying your strengths to the requirements in the job description is a must, Abdilla says. It will prove to a hiring manager that you’re the best person for the job.

Bad answers:

  • “Because I’m the best.”
  • “Because I’m passionate about it.”
  • “Because I’d be a great employee.”

Great answers:

  • “It looks like having project management experience and technical acumen is critical to this role. Let me tell you about how I’ve developed those skills at my previous jobs.”
  • “The numbers I achieved at my current job show my dedication to performance. They’re an example of the kind of results you can expect from me.”

3. What's something that you didn't like about your last job?

Even if you hated your last job, you never want to talk badly about a former employer, Foss says. Caprino agrees: “Don’t talk about a toxic boss, problems with other people, lousy leadership, too much work, too little time off, [or] too much pressure.” Instead, focus on a circ*mstance that made success more challenging without pointing fingers.

Bad answers:

  • “My boss was an idiot.”
  • “It offered me zero work-life balance.”
  • “I hated the culture.”

Great answers:

  • “I loved the people, the new projects and tasks I was given and the ability to learn and grow. One challenge, though, was that timelines, deadlines, and parameters for key projects would change constantly with no notice, so successful completion was more difficult than it could have been.”
  • “I was given the chance to contribute in a lot of different ways and worked with folks in a number of key departments, so I learned a great deal, but my manager was not the individual overseeing my work, offering feedback, or training me, which made it challenging.”

4. Why do you want this job?

“The interviewer doesn’t want to think that you’re sending out hundreds of job applications,” Foss says. “Hiring managers want you to hear the rhyme and reason behind why you applied for their job opening.”

Caprino says your answer to this question should address three key points: how your skills match the position, why you’re enthusiastic about the job, and how you fit into the company’s culture.

Bad answers:

  • “Because I need a paycheck.”
  • “Because I heard there's free lunch.”
  • “Because your office is close to my house.”

Great answers:

  • “I’m excited to see there’s a lot of opportunity to use advanced computer skills in this position. Being able to build my skills and continue to develop in a growing company is important to me, and there seems to be long-term opportunities here.”
  • “This organization's priorities for ethics, teamwork and effectiveness match my own. What's most important to me is finding a place where individuals want to work together, as a true team. I see that reflected here. The match of what you need with what I can do is clear, and the additional benefit of having the same values and community interests lead me to want to be here more than anywhere else.”

5. How do you deal with conflict with a co-worker?

Disagreements between co-workers are inevitable—but showing prospective employers how you’re equipped to handle them is crucial.

“You want to demonstrate that you have strong listening and communication skills, have compassion and empathy to sit in someone else’s shoes and be understanding, can problem-solve effectively, and can rebuild bridges and restore strong working relationships with others, which is essential to work success,” Caprino advises.

Bad answers:

  • “My co-worker kept trying to steal credit for my ideas, so I took the issue to my boss to have her intervene.”
  • “Our personalities clashed, and we fought a lot. I learned that some people just don’t get along.”

Great answers:

  • “When I have a disagreement with a co-worker, I always pull the person aside and discuss the issue privately. I listen actively to make sure I understand the other person’s point of view, and I work with the person to develop a solution together.”
  • “I take a collaborative approach to resolving conflict at work. For example, on at least three occasions, my colleague missed deadlines that pushed back our production schedule. After I discussed this with him, we found a way to improve the workflow system together and prevent that problem in the future.”

Here's an answer for you

Answering difficult interview questions is undoubtedly one of the most unnerving steps of the job search process. Luckily, one way to temper your anxiety is by knowing what's in store and crafting smart replies to tough interview questions in advance. Need some help getting prepared? Join Monster for free today. As a member, you'll get interview insights, career advice, and job search tips sent straight to your inbox. From "Why do you want this job" to "Why should we hire you," the questions coming your way require thoughtful, precise responses. Let Monster show you how to put your best foot forward.

The most difficult interview questions (and answers) (2024)

FAQs

What is the hardest interview question to answer? ›

The seven most difficult interview questions
  1. Where do you see yourself in five years? ...
  2. What are your weaknesses? ...
  3. Tell me about yourself. ...
  4. Why are you the best person for the job? ...
  5. Why do you want the job? ...
  6. Why are you looking for a new job? ...
  7. What is your salary expectation?

What is the hardest thing you've ever done interview question? ›

What is the most difficult situation you have had to face and how did you tackle it? Have an example at hand. Select a difficult work situation (which was not caused by you and which can be quickly explained in a few sentences). When choosing the problem, focus on how YOU worked towards the solution.

What is the most dreaded interview question? ›

The dreaded interview question, “Tell me about yourself,” can make even the most confident job seekers break into a nervous sweat.

What is the biggest failure interview questions? ›

Pick a real failure that happened in the workplace, specifically a failure related to the work you're doing now. Look for a story where something didn't go as planned. Choosing the right story is important, as you want to explain a situation where only one thing went wrong.

What is a good answer to your biggest weakness? ›

So there you have it. So as a recap, the four answers that you can give when being asked, what are your greatest weaknesses, are, I focus too much on the details, I've got a hard time saying no sometimes, I've had trouble asking for help in the past, and I have a hard time letting go of a project.

What is your strongest interview question? ›

Back your strengths up with stories.

What's more important than the strengths you choose is being able to back up your claims. Don't just expect the interviewer to believe you without some evidence. Start off by answering the question directly, and then segue into a story that shows off your skills.

What is the hardest decision you ever made interview question? ›

Examples of difficult decisions to talk about in an interview
  • Choosing between two enticing job offers (in the past, i.e., not during your current job search!)
  • Prioritizing two competing deadlines or projects.
  • Deciding which team member gets a promotion or other opportunity.

What is your biggest struggle interview question? ›

Be specific about why they were challenges

When you start your answer, identify what made it such a big challenge for you and make sure you explain your problem-solving process. Give them as much context as you can so they get a clear idea of how you handle these types of situations.

What is the hardest question that you can't answer? ›

Top 30 impossible questions
  • What does God look like?
  • What came first, the chicken or the egg?
  • Where do you go when you die?
  • What are black holes?
  • Why is water wet?
  • Why do people die?
  • How did the world begin?
  • Where do babies come from?

What is the killer question in an interview? ›

Common killer questions include: Tell me of a time when you worked with a difficult co-worker. Describe a situation in which you didn't meet a client's expectations. Tell me about something that you are currently learning about?

How do you crack the toughest interview? ›

How To Crack A Job Interview?
  1. Review the job description. ...
  2. Research the company. ...
  3. Revise your CV. ...
  4. Practice your answers. ...
  5. Be on time. ...
  6. Follow the proper dress code. ...
  7. Carry the required documents and devices. ...
  8. Present yourself well.
Oct 30, 2023

What annoys you the most interview questions? ›

The 6 Most Annoying Job Interview Questions, Ranked
  • “Why did you leave your previous employment?”
  • “What's your worst quality?”
  • “Where do you see yourself in five years?”
  • “What can you offer this company?”
  • “What salary are you looking for?”
  • “Where are you from… originally?”
Mar 30, 2021

Why should we hire you? ›

A: When answering, focus on your relevant skills, experience, and achievements that make you the best fit for the role.You should hire me because I am a hard worker who wants to help your company succeed. I have the skills and experience needed for the job, and I am eager to learn and grow with your team .

What is the biggest mistake interview question? ›

There are a few best practices and things to avoid when faced with this question during an interview: Pick a specific example of a true work experience (not personal) Make sure the mistake was minor, and one you successfully fixed. Keep it brief, but be prepared to provide more details.

How do you handle conflict example answer? ›

Here's how you can answer this job interview question, "When handling conflicts between team members, I always focus on finding solutions rather than dwelling on the problem. I am proactive in finding ways to resolve the conflict and encourage team members to work together towards a solution.

What is the most challenging situation interview question? ›

'Tell me how you handled a difficult situation' is one of the most challenging and common questions you may get asked in an interview. An effective way of answering this question is to give a truthful answer that outlines how you overcame a particular scenario.

What is the toughest decision you ever have to make interview? ›

Here's another sample answer: "One of the hardest decisions I've had to make was choosing between two strong team members for a promotion. I personally liked one person better than the other, but I had to choose the person I liked less, because they were more qualified to succeed in the new role.

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