How to Answer These 5 Hard Interview Questions

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 likely ask some hard interview questions. If you don’t know how to respond impressively, 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. Read on to find out how to answer and how not to answer these types of questions (including the undeniably weird ones.)

What Is the Purpose of Asking Hard Interview Questions?

Interviewers often include tough questions to dive deeper into who you are and what makes you tick beyond just your resume. Here are some things they're looking to uncover about you:

• Your problem-solving skills. Those difficult interview questions aren't just there to stump you—they're an opportunity to demonstrate how you approach and solve complex problems.
• How you handle pressure. How do you fare under stress? That's what interviewers are trying to find out with challenging questions. It's crucial for them to know if you can stay calm and collected in high-pressure situations, especially in demanding roles.
• Your self-awareness. When asked about weaknesses or past failures, it's not a trap but a chance for you to show that you're self-aware and open to growth.
• Your communication skills. Hard interview questions require you to articulate your thoughts clearly. They test your ability to communicate effectively, an essential skill in any role that involves teamwork or client interactions.

How to Navigate Hard Interview Questions

Tricky interview questions are typically challenging because they require more than straightforward, factual answers. They often demand self-reflection, critical thinking, or the ability to handle hypothetical, high-pressure scenarios. Here's what makes them particularly tough:

• Complexity. These questions often have multiple layers, requiring you to think critically and evaluate various factors.
• Emotional insight. Questions about failures, weaknesses, or conflicts can be uncomfortable as they force you to reflect on personal shortcomings or difficult moments.
• Abstract thinking. Some oddball questions might ask you to think abstractly or conceptually, such as solving hypothetical problems or predicting future trends.
• Pressure to perform. The knowledge that your responses could make or break your job prospects can add significant pressure, making it harder to think clearly and respond effectively.

To make answering hard interview questions less stressful, consider the following strategies:

• Reflect on your experiences. Before the interview, reflect on your past work experiences, challenges, and achievements. This will make it easier to draw on relevant examples during the interview.
• Structure your responses. Use frameworks like the STAR Method to organize your answers. This not only helps you provide a clear, concise response but also ensures you hit all key points of your story.
• Remain calm and composed. Practice mindfulness or stress-relief techniques to improve your ability to stay calm under pressure. Relaxation will help you think more clearly and communicate more effectively.
• Stay positive. Even when discussing negatives, such as a failure or weakness, focus on what you learned and how you've improved. This turns a potentially difficult conversation into demonstrating your growth and resilience.

What Are the 5 Hardest Interview Questions?

When you step into an interview, you're also diving into deeper waters where you may feel that some of the worst interview questions lurk. Below, we explore five hard interview questions that can truly test your mettle, pushing you to demonstrate what you know and how you think and respond under the spotlight. Use our sample answers to help you create your own answers based on your unique situation.

1. What's Something That You Didn't Like About Your Last Job?

This is one of the hardest questions to answer as it requires you to critique a past workplace without coming across as unprofessional. Interviewers ask this to gauge your professionalism, see how you handle conflicts, and understand what work environments or management styles you might struggle with.

Choose an aspect of the job that was challenging but didn’t align with your goals for personal or professional growth. This way, you can show that you’re able to rise to a challenge but ultimately make a deliberate choice to follow your ambition.

Remember, even if you hated your last job, you never want to talk badly about a former employer. Don’t talk about a toxic boss, problems with other people, lousy leadership, too much work, too little time off, or too much pressure.

Bad answers:

• ”My boss - he was an idiot. He was overbearing, criticized my work constantly, and tried to micro-manage me all the time.”
• ”I hated the company culture. It was far too competitive, and people were generally out for themselves rather than working as a team.”

Great answers:

• ”One challenge I encountered was the frequent changes in timelines, deadlines, and parameters for key projects, often with little to no notice. However, this experience taught me the importance of flexibility and effective communication. I learned to quickly adapt and collaborate closely with my team and management to realign our goals whenever changes occurred.”
• ”I had the opportunity to work under multiple managers, which provided a diverse learning environment but also created challenges due to mixed directives. To address this, I initiated regular update meetings and a shared document for feedback consolidation, enhancing project coordination. This experience taught me the value of clear communication and organizational skills in managing complex team dynamics."

2. How Do You Deal with Conflict with a Co-Worker?

Hard interview questions like this can be challenging because they require you to admit to past conflicts without casting yourself or your colleagues in a negative light. Interviewers ask this to assess your interpersonal skills, approach to resolving disputes, and ability to maintain a professional demeanor under stress.

In your answer, aim to demonstrate that you have strong listening and communication skills, compassion and empathy, and the ability to put yourself in someone else’s shoes. Interviewers are also looking for your problem-solving skills and ability to rebuild bridges and restore strong working relationships with others, which are essential to work success.

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 them 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 from occurring in the future.”

Weird Interview Questions

These types of unusual interview questions might take you by surprise, posing odd or seemingly unrelated challenges. However, they serve a strategic purpose in interviews. These hard interview questions test your creativity and problem-solving skills by pushing you to think outside the box and respond spontaneously. Essentially, they aim to uncover your genuine reactions and thought processes, peeling back the layers of rehearsed answers to reveal a more authentic side of you.

3. If You Were an Animal, Which One Would You Be?

Interviewers use these kinds of hard interview questions to gain insight into your self-perception and personality traits and how these could mesh with the company culture. Consider the qualities you want to highlight in the interview and choose an animal that embodies those traits. Prepare a brief explanation of why you chose that animal, focusing on positive attributes relevant to the job.

Bad answers:

• "I guess I'd be a snake because they're sneaky and can get away with things. They know how to navigate tricky situations to get what they want without drawing too much attention.
• "I'm not sure, maybe a parrot because they just repeat what others say. I think it's easier to just go along with what's already being said instead of coming up with new ideas."

Great answers:

• ”I would be an eagle because they’re known for their sharp vision and ability to focus on their goals from a distance. Like an eagle, I’m detail-oriented and can maintain a broad perspective on projects, which helps me foresee and navigate potential challenges. This trait has been crucial in my role as a project manager, where strategic planning and foresight are essential."
• ”I would choose to be a dolphin, as they are both highly intelligent and excellent communicators within their pods. I value clear communication and collaboration in the workplace, much like dolphins, to ensure that projects run smoothly and efficiently. My ability to work well in a team and foster a supportive environment has been a significant asset in my career."

4. If You Could Have Dinner with Any Fictional Character, Who Would It be and Why?

Unusual, hard interview questions like this assess how well you can engage with abstract ideas, communicate your thoughts, and perhaps understand what kind of narratives or characters inspire you. This can give them a glimpse into how you perceive the world and what qualities you admire or aspire to emulate.

Choose a character that you genuinely connect with or find intriguing. Prepare by thinking about what this character represents and how those qualities relate to your own life or work ethic.

Bad answers:

• "I would have dinner with James Bond because he leads an exciting life full of adventure and danger. It'd be thrilling to hear about all his spy missions and escapes."
• "I'd probably pick Harry Potter because he can do magic, and that's cool. It would be amazing to see him perform spells in real life."

Great answers:

• ”I would choose Spider-Man because he embodies resilience, a keen sense of responsibility, and the struggles of balancing personal life with the duty of helping others. These qualities are not just central to his character - they are also essential in my field, where I am constantly juggling multiple responsibilities and striving to make impactful decisions that benefit my team and community."
• "I would choose Sherlock Holmes because he demonstrates analytical thinking, attention to detail, and a profound ability to solve complex problems. Furthermore, his resilience and dedication to his craft inspire me to maintain a high level of precision and excellence in my work, striving always to uncover the truth beneath the surface of things."

5. If You Found a Wallet on the Street with $100 inside, What Would You Do?

This tricky question can be especially challenging because it puts you in a moral quandary, directly testing your ethical standards. Interviewers ask these hard interview questions to gauge your integrity and honesty, which are crucial in any professional setting. This scenario also assesses your ability to handle situations that involve personal gain rather than doing the right thing.

Focus on demonstrating clear ethical reasoning to make responding to this question more straightforward and less daunting. Emphasize that maintaining trust and doing the right thing align with your personal values and would be your approach in any professional context as well.

Bad answers:

• "I might take the money out and then drop the wallet back on the street. Someone else might need the ID and cards more than the cash."
• "I'd keep the wallet and use the money as a reward for finding it. If no one has claimed it, it's probably meant to be mine anyway."

Great answers:

• ”My initial reaction would be to use any membership cards within the wallet to attempt to contact the owner. For example, if there's a gym card, I could call the gym with the owner's membership information and ask them to notify the owner. This method ensures privacy and security, requiring minimal direct access to personal information. It also demonstrates resourcefulness and a proactive approach to solving problems, key qualities I bring to my professional life."
• ”My first step would be to look for any identification and return it to the owner directly. If no contact information were available, I would take it to the nearest police station or leave it with a local business where it was found, ensuring it's in safe hands. It's important to me to do the right thing. I believe in treating others' property with respect and integrity, just as I would want my own property treated."

Land More Job Interviews with an Impactful Resume

Get your resume into shape for more opportunities to show how well you can answer hard interview questions. Rise above other candidates by letting the writing experts at Monster’s Resume Services take your first draft to the next level. They’ll create a tailored, keyword-rich resume that showcases your skills and unique value proposition so you can start winning more interviews.