How to Answer the 8 Hardest Interview Questions

Picture this: you, armed with the power of preparation, confidently go into an interview and feel like you absolutely nailed it. But then you hear back, and you’re surprised to learn that you didn’t get the job. So now you may be wondering what you said or perhaps didn’t say that cost you the opportunity. No matter where you are in your career, it's not always clear how to answer the hardest interview questions. While preparation is key to a great interview, you must be able to hone your answers and know if you’re conveying the right message. But here's a little secret: sometimes, seemingly easy questions can be the trickiest to tackle.   Below is our guide to give you insight into how to answer the hardest interview questions. We've carefully compiled a lifesaving list designed to ignite your self-awareness allowing you to understand the reasoning behind why these questions are asked and ultimately empower you to prepare and masterfully handle even the toughest of questions. No more surprises – you'll be armed and ready for anything that comes your way!  

How to Answer the 8 Toughest Interview Questions:

1. Tell me a little bit about yourself.

Everyone trips up on this question because they overthink it. It’s a quick pitch: where did you go to school, how did you get to where you are today, and what brings you to this interview? It should not be overthought and should not feel scripted. Ditch the script taped up on the side of your laptop screen. Seasoned recruiters know when you’re looking off to the side and reading from a prompt! Here's the magic: resist the urge to overthink it and avoid sounding like a rehearsed robot. You are your own best expert, so let your introduction flow naturally. Embrace your uniqueness, confidently introduce yourself, and leave them in awe of your authenticity.  

Infographic that describes a winning strategy for answering the question "tell me a little bit about yourself."

2. What is your greatest weakness?

This is a classic question. The interviewer wants to find out how you self-assess your weaknesses and how you handle critiques and feedback.  They are asking you to go to a deeper level and show your skills for introspective thinking. For example, a personality trait like impatience, while not ideal for situations where you’re waiting for information has allowed you to take charge of timelines or deadlines, use that to your advantage. In other situations, these traits may be seen as the best skills they need in someone for a particular role.  

Infographic that describes a winning strategy for answering the question "What is your greatest weakness?"

3. What other career options or jobs are you interviewing for? Are you in any final stages with other firms?

This is an important question to answer thoughtfully. Be transparent, yet strategic. Don’t shy away from expressing your excitement about this opportunity. If you have other offers or are in the final stages with another company, share this but explain the thoughtfulness you have put into this search and what drew you to the company you are interviewing with. Reiterate your excitement about the opportunity that is on the table and if they are your first choice, be sure you tell them! Normally, if they ask you this question, they are very interested and want to see where they stack up against other competing companies or offers.  

Infographic that describes a winning strategy for answering the question "What other career options or jobs are you interviewing for? Are you in any final stages with other firms?"

4. Why did you leave your last position?

This question requires honesty, and the interviewer will be put off if you seem to be trying to hide something. Keep it light and truthful. Stay away from saying anything negative about your past employer or previous workplace. Be professional and explain what you learned in your last role if the conversation calls for it. Ultimately, the interviewer is just trying to get a better picture of you and your motivations for leaving a position.  

Infographic that describes a winning strategy for answering the question "Why did you leave your last position?"

5. You are underqualified for this role, why should we hire you?

This question is all about confidence and understanding that you know you have skills to prove. Don’t overcompensate for the skills you lack but showcase abilities you’ve proven in other roles that would allow you to quickly step into a larger role. Build a connection between your past experiences and the requirements of the opportunity to show that you can handle these new tasks. The goal here is to ensure they know you’re up for the challenge and excited to be trusted with more.  

Infographic that describes a winning strategy for answering the question "You are underqualified for this role, why should we hire you?"

6. You seem overqualified, will you be happy here?

This is an opportunity to reinforce your interest and ensure the job is also a good fit on your end. Explain why you were drawn to this opportunity, and if you're truly overqualified, why did you choose to pursue this opportunity at this point in your career. Maybe your last role was 24/7 and now you just want to settle into a more structured role because it suits your current lifestyle. Whatever it is, be transparent and explain your motivations. Give the interviewer confidence that you will be happy in this role and that this opportunity is the right one for you at this stage of your life.

Infographic that describes a winning strategy for answering the question "You seem overqualified, will you be happy here?"

7. Why should we hire you?

First things first, take a moment to reflect on those skills you possess and what the interviewer shared about the scope of responsibilities. What makes you uniquely positioned to be successful? Consider your own motivations as well – what drew you to this role? Why is this the right fit for you and the trajectory of your career? What connects you to the company?   Connecting the dots between your skills and what this position demands should be a piece of cake!   Now, when you deliver your answer, let it resonate with genuine enthusiasm. Share your unwavering dedication and conviction that this role was meant for you, and because of your qualifications and passion, the role is overall the right long-term fit.  

Infographic that describes a winning strategy for answering the question "Why should we hire you? "

8. Where do you see yourself in a few years?

This is hands down the number one question that most people get wrong, or struggle with. Unless you have a crystal ball there is not a real answer to this question. Most of the time you don’t even know where you see yourself a year from now and honestly a lot can happen in a year to change your course in life. While it seems simple enough, the interviewer is asking you about how you view growth and what your interpretation of your “growth timeline” looks like.  Most interviewees want to discuss their own motivations for their growth path. Maybe law school, maybe growing into a manager position, or the worst answer – starting your own business! Bringing up personal dreams with this question can sometimes come across as self-serving or off-putting to the interviewer – and most of the time what you share (like you wanting to start your own company) just means you’ll be a flight risk.

So, how do you answer this question? KEEP IT SIMPLE!  The best way that you can answer this question is by first acknowledging that while development is important to you, you’re not entirely sure what this looks like. So, you first admit the unknown and then follow it up with two truths or two irrefutable facts: #1 That you want to do meaningful work and contribute to the bottom line of a business, and #2, That you want to work with a great team, good people, and feel like a valued part of an organization. None of us know where our careers will take us, but we can all agree on shared values and goals.

Infographic that describes a winning strategy for answering the question "Where do you see yourself in a few years?"

Remember, it’s equally important to connect with your interviewer throughout the conversation. You don’t need to have the perfect answer to every question, you may even trip up and show you’re human. What you do need is a great attitude, a humble dose of confidence, and a genuine desire to make a positive impression.

Now that you know how to answer the hardest interview questions, head to our Find Work page to explore new opportunities and follow us on LinkedIn to stay up to date with everything that we are doing here at Career Group Companies.  Happy Interviewing!

Jenna Nicholas

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Originally from Dallas, Jenna Nicholas graduated from the University of North Texas, where she received her Bachelor of Arts Degree in Psychology, with a minor in Business Management. Since joining Career Group in 2010, Jenna has become an integral member of the team. Jenna has a range of experience recruiting for full-time and direct hire roles that span corporate industries from startup to the most successful global brands as well as Private Family Office. She is committed to excellence in finding the right talent for her clients and ensuring a long-term fit. In her spare time, Jenna enjoys traveling, trying new restaurants, spending time with her family and two rescue dogs, Bruce and Eli.

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