The most difficult interview questions (and answers)

Learn strategies for answering some of the toughest interview questions.

The most difficult interview questions (and answers)

Nail even the toughest questions—when you're prepared.

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 circumstance 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.