What is the Most Difficult Interview Question?
We’ve gathered 12 of the most challenging interview questions from a diverse group of professionals, including a $100k+ Resume Writer and Career Coach, CEOs, and a Community Manager. From navigating the classic “Tell Me About Yourself” to tackling ethical dilemmas, these experts share their toughest interview experiences and how they approached them.
- Navigating “Tell Me About Yourself”
- Tackling “Why Work Here?” Specifically
- Flipping “Why Shouldn’t We Hire You?”
- Discussing Failure and Growth
- Throwing Oddball Questions Test Creativity
- Handling Multi-Part Questions
- Addressing Resume Gaps
- Presenting a Unique Belief Challenge
- Balancing a Tough Salary Expectations Question
- Answering, “Why Should We Hire You Over Other Candidates?”
- Mastering the Questions Designed to Throw You Off
- Passing an Ethical Dilemma Test
Navigating “Tell Me About Yourself”
“Tell me about yourself?” has to be the most hated and most difficult interview question that I’ve ever asked or been asked. The reason why is that it’s an open-ended question with endless possibilities for an answer. If you want to get the job, you absolutely have to know how to nail “tell me about yourself.” Pro tip: Your answer should absolutely focus on the parts of your skills and experiences that align with the job.
Ashley Cash, Resume Writer and Career Coach, Ashley Cash Coaching & Consulting
Tackling “Why Work Here?” Specifically
As an HR manager, one of the most difficult questions I’ve had to ask an applicant was “Why do you want to work here?” Interviewers and applicants usually tiptoe around this question because it’s an awkward conversation.
Often, applicants will say something vague and generic like “I want to work here because it’s a successful company,” which doesn’t really tell me anything, nor does it tell me that they’re a motivated applicant.
Applicants need to be specific. For example, if an applicant has a background in marketing, they could say “I want to work here because your marketing team has done a great job with your branding, and I’m interested in learning more about how you do digital marketing campaigns.”
This tells me that this applicant has done some research on our company and has specific goals in mind for what they want to learn from our company.
Matthew Ramirez, CEO, Paraphrasing Tool
Flipping “Why Shouldn’t We Hire You?”
The most challenging question I once received was “Why should we NOT hire you and instead hire someone else?”
I saw this as a flip of “Why are you the best person for the job?”. Using key elements of the job description, my reply basically said, if you’re looking for the opposite of what is in the job description, such as someone who does x, y, and z, don’t hire me. If you’re looking for someone who aligns with all elements of the job description, I’m your person.
Melissa Rubin, Associate Director, MBA Career Development
Discussing Failure and Growth
The most difficult interview question I’ve encountered is “Tell me about a time when you failed and how you handled it.” This question is challenging because it requires introspection and the ability to discuss personal or professional setbacks in a constructive manner. It forces the candidate to reflect on their failures, analyze the lessons learned, and demonstrate resilience and problem-solving skills.
As an interviewer, I have also asked this question to candidates. It provides valuable insights into their self-awareness, ability to take ownership of mistakes, and their attitude towards learning and growth. The difficulty lies in finding a candidate who can honestly acknowledge their failures without deflecting blame or dwelling on negativity.
The ideal response includes a clear description of the failure, the actions taken to address it, and the key takeaways that have contributed to their personal and professional development.
Trey Ferro, CEO, Spot Pet Insurance
Throwing Oddball Questions to Test Creativity
I love to ask oddball interview questions. This is partially because I’m whimsical and partially because I like to see how people respond to unfamiliar situations where they need to think creatively.
Something like this is ideal: “Suppose you live and work in Canton, Ohio. What is the ideal number of gears your bicycle should have?”
I don’t particularly care about the answer, but the thought process is key. I want to see what information they would use to come to an answer: geography, climate, infrastructure, knowledge of bicycles or lack thereof, and so forth. I learn a ton when somebody posits an answer to a question like this.
Temmo Kinoshita, Co-founder, Lindenwood Marketing
Handling Multi-Part Questions
Any question that requires answering multiple parts can be difficult. For example, I’ve had to answer this question (which happens to be several questions linked into one):
“What does conflict resolution mean to you? Tell me about a situation when you’ve had to deal with conflict resolution. What was the problem, what was your method of solving it, and what was the outcome?”
It’s not that the actual question is that difficult to answer, but rather the multiple parts that need to be covered. It’s perfectly fine to take a moment and write down the parts of the overall question and come back to each to make sure you have a complete answer.
Kelli Anderson, Career Coach, Resume Seed
Addressing Resume Gaps
A hard question that I’ve been asked is about gaps in my resume. My response is that my career is not linear. I’ve taken time to pause and ensure that work is focused on supporting my values. Then I’ve returned to work with renewed energy and alignment.
I took time off with my second child since I wasn’t in a position to do so with my first and I wanted to be fully present for that fleeting moment in life. I can assure you that any gaps have better prepared me and informed me of who I am today.
A person that is centered on values and one of my values is accountability. If I say that I’m going to do something or commit to a role, then be assured, I’ll do it and do it as well as I can.
Joanne Jastatt, Leadership Coach, Jastatt Coaching
Presenting a Unique Belief Challenge
The interview question, “What’s something you believe that almost no one else does?” presents a fascinating challenge. It requires deep introspection and thinking creatively to identify a unique perspective or belief that sets the candidate apart. Most interviewees do not have a ready answer at hand, so I have often asked this question right before a 5-10 minute break in the discussion.
Trevor Ewen, COO, QBench
Balancing a Tough Salary Expectations Question
The toughest question you can ever be asked in an interview is “What are your salary expectations?” This question requires you to balance your worth and the market rates, without scaring off potential employers or undervaluing yourself.
What I found to be tremendously helpful is a pre-interview trip to the Blind forum. You can often find real salary numbers anonymously shared by people in similar positions, which gives you a realistic benchmark to aim for.
Once, I answered this question by saying a number slightly higher than I was hoping for. To my utter surprise, the company totally went for it and offered me almost double what I was making at my previous job! So make sure to always come prepared, know your worth, and have an idea of what a particular company has to offer.
Juliet Dreamhunter, Founder, Juliety
Answering, “Why Should We Hire You Over Other Candidates?”
You should focus on highlighting the unique skills, experience, and personal qualities you possess that would make you the best for the job. Highlight your skills and experience. Emphasize your past achievements. Be enthusiastic and confident, but humble in your response to this question. Prior to any interview, you should do your research on the company and have a good understanding of the job details and requirements.
Kevin Barrett, Manager, Talent Acquisition, Edge Electric
Mastering the Questions Designed to Throw You Off
An interviewer once asked me the following question: “Why do you think your husband chose you?” The company was recruiting a mid-level manager in a fast-paced and somewhat unpredictable environment. The question came out of the clear blue sky, and I wasn’t prepared for it.
After the interview, I realized that it was their way of evaluating a candidate’s stress tolerance and potential response to sudden, unforeseen situations that would require immediate reaction.
While the question might not be difficult to answer, I felt uncomfortable discussing such an intimate matter with someone I barely knew. I have, therefore, never adopted this approach in my recruitment projects. However, the idea of adding an off-topic question to your regular set of interview questions to see the applicant’s reaction might be worth a try.
Liga Vasila, Chief Editor, FoodyWise
Passing an Ethical Dilemma Test
“Describe a time when you faced an ethical dilemma and how you resolved it.” The question goes beyond evaluating technical skills, delving into the core of an individual’s values, decision-making, and adeptness in confronting moral challenges. That’s why it becomes a test of character.
Answering requires deep introspection and self-awareness. It may involve revisiting difficult or uncomfortable memories and evaluating one’s conduct. The challenge also lies in delivering the answer. Crafting a compelling response requires analyzing multiple perspectives and considering the consequences of one’s actions. Articulating the details clearly is crucial, showcasing communication skills and expressing complex ideas concisely.
The significance of a question resides in its profound implications. It serves as a litmus test, assessing a candidate’s moral compass and revealing a commitment to ethical comportment, honesty, and integrity. It tests the ability to recognize and address ethical issues under pressure.
Nina Paczka, Community Manager, Resume Now
