9 of the most difficult interview questions – and how to answer them

Job interviews are difficult enough. In the spirit of job interview preparation, we rounded up some of the toughest job interview questions.

Seriously, job interviews are difficult enough. So why this whole trend in asking questions that stump candidates? 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.

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.

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 with these questions is to test how self-aware you are but also how open you are to discussing flaws and mistakes. You should be able to 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?).

2. What tasks do you not like to do?

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 a weakness 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, 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.

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.

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, which makes your interviewer more likely to connect with you — but we’d also recommend tying it back to your career. Mention some blogs you visit regularly that have to do with 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 also passionate about the work you’re doing/would like to be doing for them.

4. If we gave you a $1 million marketing budget, where would you spend it and how would you measure ROI?

These are what our founder (and former Hulu recruiter) 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 It

This is about showing a clear knowledge of the company’s goals and interests, as well as 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 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 doesn’t hurt either 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.”

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 It

Especially if you got fired, it’s essential that you keep your response succinct and 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 because 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.”

6. What do you dislike most about your current job?

Eesh.

How to Answer It

You probably know by now that you shouldn’t bash your current company 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 or the projects you’ve loved most that you haven’t been able to work on enough. Tell them you’re looking for a job 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 (don’t make it entirely about you).

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 It

Look for inspiration in the job posting! 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 a 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.

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?”

How to Answer It

Through a problem-solving lens. Through your research and even the current interview, you should have a pretty good grasp on what the company is struggling with. Your answer should focus on how you’re uniquely qualified to help them tackle those issues head-on.

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.

This article first appeared on Career Contessa.