Have you ever failed an interview because one difficult interview question stumped you?
I love a thought-provoking conversation as much as anyone, but when you're trying to put your best foot forward in a job interview, chances are you're holding your breath, waiting for the worst one to hit you. In the spirit of job interview preparation, we rounded up some of the toughest job interview questions.
Learn why an interviewer might ask these difficult interview questions, how to prepare for the biggest doozies beforehand, and how to answer the toughest interview questions thoughtfully.
Table of Contents
- Why Do Interviewers Ask Difficult Questions?
- What Is Something People Assume About You That Is Incorrect?
- What Tasks Do You Dislike?
- What are You Currently Reading?
- If We Gave You a $1 Million Dollar Marketing Budget, Where Would You Spend It, and How Would You Measure ROI?
- Explain This Gap in Your Resume
- What Do You Dislike Most About Your Current Job?
- What Does the Ideal Work Day Look Like to You?
- Why Should We Hire You?
- What's Your Desired Salary?
- More Tough Interview Question Examples
If you're interviewing, prepare for these or similar ones. If you're hiring, we wouldn't blame you if you worked a few of these into your own list.
Why Do Interviewers Ask Difficult Questions?
Because they want to see you sweat. Just kidding. While there might be evil interviewers out there, most are simply looking for insight into who you are, your motivations, how you work with colleagues, and other information that you may have touched upon in your resume or cover letter.
Interviewers ask tough questions for the following reasons:
- To learn more about you
- To see how you handle yourself under pressure and in stressful situations
- To watch your thought processes and critical-thinking skills
When you're asked something you either didn't expect or something hard to answer in general, the hiring manager gets to see how you manage working through something you're uncomfortable with—or even something you don't know.
Sometimes, they do this to gauge your genuine answers. They don't want to hear the memorized sample answers you're prepped before the interview. They want to hear great answers that showcase your unique skills. Themes might include time management, conflict management, leadership, customer service, communication skills, and your own personal attributes.
Pro Tip: Whenever possible, answer these tough questions with personal anecdotes, stories, and professional highlights. Share experiences demonstrating your je ne sais quoi—what makes you unique.
While we are not crystal balls who can tell you exactly what the hiring manager will ask, we can do the next best thing by sharing common difficult interview questions that we've heard asked by actual hiring managers.
Bonus: We have created LOTS of job interview advice, including how to answer all sorts of questions right here.
1. What Is Something People Assume About You That Is Incorrect?
This is what one of our teammates describes as an "introspective question," and there are similar ones that come up as well, such as:
- Tell me about an error in judgment that you made in the last year. What was its impact?
- When have you been most satisfied in your life?
How to Answer It:
The goal of these questions is to test how self-aware you are but also how open you are to discussing flaws and mistakes. You should share some honest experiences but also focus on spinning those negative experiences into positive ones. For example, that error in judgment should have ultimately made you into a better worker somehow (I mean, didn't it?).
Example Answer:
"People assume I struggle to make decisions, but the reality is that I really like to know all the facts first. It takes me time to gather data and feedback, but it helps me make the right decision, which I think is better than making a quick decision."
2. What Tasks Do You Dislike?
Similar to other introspective questions, there's one key distinction here: This question is meant to tell your interviewer a bit more about your working style.
Are you more of an independent worker? A fan of group projects? But also, are you aware of how you work best? Because ultimately, they want to hire someone who knows how to ask for what they need to perform.
How to Answer It:
Start by focusing on one of your greatest weaknesses you've recognized in yourself such as, "I've never been the most comfortable in front of crowds, so I've always dreaded public speaking or presenting in big meetings."
Then, explain how you've worked on improving those weak spots. "I used to dislike public speaking so much that I decided to sign up for Toastmasters. I realized getting better about it is essential to my career..." And end with something like "Even though it's still not something I completely enjoy, I've gotten a lot more comfortable in roles that require I do it."
This shows that you're willing and open to do the things you don't want to do—because let's be real, no job is fun all the time.
Example Answer:
"I've never been the most comfortable in front of crowds, so I've always dreaded public speaking or presenting in big meetings. I used to dislike public speaking so much that I decided to sign up for Toastmasters. I realized getting better about it is essential to my career, and the more I present to the team, the better I get and more comfortable I am. Even though it's still not something I completely enjoy, I've gotten a lot more comfortable in roles that require I do it."
3. What Are You Currently Reading?
When I sat down to write this article, three out of five people I asked said they'd been given this question before. I have, too. So clearly, it's a popular one with hiring managers, even though it seems out of left field.
First of all, don't lie when answering this question.
How to Answer It
Feel free to include some details about the current novel or memoir you've got on your nightstand—this is a great way of showing some personality. This helps your interviewer to connect with you on a more personal level—but we'd also recommend tying it back to your career.
- You Might Also Like: How to Answer "What Was the Last Book You Read?" in an Interview
If you're not a big book reader, mention some blogs you regularly visit that relate to your industry. Talk about a recent article you read on a topic that overlaps well with your professional interests. This shows the interviewer that you're well-read and as well as passionate about the work you're doing—or would like to be doing for them.
Example Answer:
"For fun, I'm reading Such a Fun Age with my book club, but I'm also an avid reader of a few news outlets and subscribe to way too many newsletters. Most recently, I read an interesting LA Times article about how Gen Z is going to shake up the workplace. As a millennial, it's fun to read about the comparisons with our generations and keep me on my toes working in career development."
4. If We Gave You a $1 Million Dollar Marketing Budget, Where Would You Spend It, and How Would You Measure ROI?
These are what our founder (and former Hulu recruiter), Lauren McGoodwin, refers to as "case study questions."
It's about getting into specifics and testing your knowledge of the company you're applying to—which obviously, you should have researched before your interview.
Other examples:
- What issues should the team consider when evaluating the value of XYZ company's existing product line?
- If hired, what would you like to change about our company/your department?
How to Answer:
This is about clearly knowing the company's goals and interests and a smart critical eye. Get as specific as possible as you're talking, and don't be afraid to ask questions of your interviewer for clarity.
Think: "I saw on your site that you're expanding into offering e-learning as well as your live events. Is that something you're planning for in the next few months? [Answer] "...In that case, I would say that I'd want to put a good portion of the marketing budget into that because..."
It also doesn't hurt to mention teamwork and consulting to get the job done. Every interviewer likes to hear you say, "But before I committed to any of this, I'd want to talk to the stakeholders and get to know their goals a little better."
Example Answer:
"I can give you a quick example of my thought process for where I would start given that I don't have all the details of course. In my experience, before you spend a dollar, it's important to learn what the goals are for the company and how they will be measured. From there, I would take inventory of what's working right now and what's not working. For example, if paid acquisitions are getting us a high number of subscribers but the churn rate is too high, then I would want to solve the churn rate first before I put more money into paid marketing."
5. What is This Gap in Your Resume?
Maybe you got laid off or fired, maybe you took time off to raise a child, or maybe you took time off to travel. If an interviewer notices a missing period of time, they'll likely ask you about it.
How to Answer:
Especially if you got fired, it's essential that you keep your response succinct. Place the focus on how you took control of the situation and why you're ready to get back to work.
One good way to spin this is to focus on the things you learned during your period of unemployment. An example answer might be: "This was actually a great experience for me in a way I hadn't expected. I started doing freelance marketing projects, and quickly realized that I was fascinated by social media growth strategies, which I hadn't been able to focus on at my previous job."
Example Answer:
"I was laid off due to a corporate merger in early 2020 and then the pandemic happened. During that time, I cared for my family, home-schooled my kids, and enrolled in online classes to keep my technical skills sharp before I went back to the job search. To be honest, being a full-time teacher and parent was probably the best project management training I could have ever gotten. That's why I included some key takeaways from this time on my resume."
6. What Do You Dislike Most About Your Current Job?
Eesh. This is right up there with "Why are you looking for a new job?" and no one enjoys that question either, but as the interviewee, you'll want to play this question strategically.
How to Answer:
You probably know by now that you shouldn't bash your current company, employees, or boss, so what happens when a question like this comes up?
This is a good time to go with the classic "it's not them, it's me" approach and focus on why it's not a good fit for you. Tell them about some of your strongest skills, career goals, or the projects you've loved most that you haven't been able to work on enough.
Tell them you're looking for a new position that lets you use those skills more often. Whatever your "dislike most" answer is, it should be something that the new job would solve for you—but it should also be something they need help with (i.e., don't make it entirely about you).
Example Answer:
"My current role shifted a lot in the last few years and while I enjoy the challenge of taking on new skills, it can feel like the finish line is always being moved on me. One thing that really attracted me to this role and company was your clearly-defined mission and incredible product. Without having to change priorities each day, I could deeply focus on the customer experience your company is working toward. Here are just a few of my ideas..."
7. What Does the Ideal Work Day Look Like to You?
This is tricky because, often, there are subtle work expectations that companies don't talk about. Maybe people don't take lunches or they stay late a few nights a month to finish big projects.
That's where things can get hairy. (Do you say, "I like to work flexible hours and maintain a good work-life balance on weekends" if you're not sure whether the job is, in fact, flexible?)
How to Answer:
Review everything they wrote there before going into your interview. Look on their website careers page, too. These places should give you a good idea of company culture.
Chances are part of what you applied was because something about the culture appealed to you, so talk about that. It also never hurts to say something like, "I know we love work-life balance, and in an ideal universe, we'd all go home at the same time every day and not check our emails until we got into work. But I also know that there will be times when that's simply not the reality."
We're all in this together.
Example Answer:
"My ideal work day would include time to complete my tasks without jumping from non-stop meetings and needing to work late into the night to get my work done. While I really appreciate the collaboration we get to have in a meeting, I think it's important for team productivity and focus not to do all my work in the late evening."
8. Why Should We Hire You?
A danger zone between self-assured and cocky, this essentially amounts to "What makes you so special?" and "Why do I need you?" This also reminds us of a common interview question, "Why do you want to work here?"
How to Answer:
Through a problem-solving lens.
Through your research and even the current interview, you should have a pretty good grasp of what the company is struggling with. Your answer should focus on how you're uniquely qualified to help them tackle those issues head-on.
Example Answer:
"One thing you've mentioned a few times in our interview is the company's priority to launch online courses, and I'm confident that my past experience would make me a valuable team member. Not only have I written, filmed, and produced courses in the past, but I have also launched them and created ongoing marketing funnels. Launching a course is definitely challenging, but evergreen marketing is what will increase your revenues."
9. What's Your Desired Salary?
Other similar questions include:
- How much do you expect to get paid?
- Are you open to added benefits/stock options in exchange for taking a lower salary? (Often startup-specific, especially when interviewing someone from a non-startup.)
How to Answer It
You need to have a range ready to go. Do this long before you walk into the interview by using various salary tools, including The Salary Project™.
You should also have an explanation for why that's your desired salary with clear evidence of why you should be paid that amount.
Example Answer:
"I do have a salary range in mind that I've determined based on research and taking into account my 10+ years of PR experience. I believe my experience level, qualifications, and multiple PR awards add value to my candidacy; however, I'd like to wait to share my range until I learn more about the responsibilities and expectations of this role. I have no doubt that if this is fit we can determine a fair salary number."
More Tough Interview Question Examples
Sadly, the list of difficult and tough interview questions doesn't end with nine. Here are a few more to consider when prepping yourself for difficult interview questions:
- What critical feedback have you received in the past?
- How do you handle stress?
- Tell me about yourself.
- What motivates you?
- How do you define success?
- What management style works best for you?
- How do you deal with conflict?
- Why do you want to work here?
- Why do you want to change your current career path?
- Other behavioral interview questions
- What is your biggest weakness?
- What is your greatest personal achievement?
