15+ Trick Interview Questions + How to Answer Them

We’ve all been there. You get a call back for an interview, and excitement bubbles up that your job search is moving forward. Hooray! But then the stress settles in, and you start getting nervous about your interview.

If this sounds familiar, you’re not alone. It’s estimated that 93% of Americans get stressed about job interviews.

While you can prepare for your interview ahead of time and practice answers to common interview questions, some trick interview questions and unexpected questions can make you nervous, even if you’ve put in the prep work.

I once botched my answer to what motivates me in a job interview and I can promise you that the ROI on your prep work is worth it!

What Are Trick Interview Questions?

Trick interview questions allow interviewers to learn more about you, how you react, and how you perceive various situations.

While we are calling them “trick questions,” the truth is that there usually aren’t wrong or right answers. The goal is to give the interviewer the insight they seek through your answer while highlighting your value as a candidate. 

In general, “trick questions” are usually behavioral interview questions. A behavioral interview question is a question designed to assess how you react in certain workplace situations. Behavioral interview questions typically take two forms—a question about a real event and how you handled it, or a hypothetical situation that could occur in the future.

Why Do Interviewers Ask Tricky Interview Questions?

Interviewers ask these questions to get a better understanding of your inner workings and how you might react in a myriad of different situations. While it might feel like interviewers are asking you tough questions to make you uncomfortable, that’s usually untrue.

Most of the time, interviewers ask tricky interview questions because:

What to Do When You Don't Know the Answer to Tricky Interview Questions

If you don’t know the answer, it’s a good idea to pause to consider what you’re going to say prior to blurting out an answer that might not accurately represent you. 

You can even say something like,

While you shouldn’t take an infinite amount of time to come up with the perfect answer, taking a moment to pause and collect your thoughts can benefit you in a few ways.

Pausing to collect your thoughts can:

The 15+ Trickiest Interview Questions and How to Answer Them

We’re highlighting the most common tricky interview questions and how to address them during your interview. 

1. Tell Me About Yourself

Why It's Tricky:

There are a couple of reasons why this question can be tricky. First, because it’s open-ended, it can tempt you to drone on without providing a succinct answer.

Additionally, if not practiced, it can be second nature to go into detail about your personal life instead of focusing on your career and why you’re interviewing for the position. 

Why the Interviewer Is Asking:

Interviewers usually do want to know more about you, particularly from your own perspective. On the surface, that’s why this can seem like a simple question. 

With that said, interviewers often want to see how candidates can create a concise answer from an open-ended question, and how well they can pitch themselves. This may be particularly important in a sales or client-facing role where you’ll have a lot of facetime with customers or key accounts.

How to Answer:

Here is our simple formula—a four-step process—for answering this question regarding the job—and organization—at hand.

Use this formula to create a full-circle answer that brings you to why you’re interviewing for the position and how everything has led up to this point in your career.

2. What Is Something People Incorrectly Assume About You?

Why It's Tricky:

Ideally, you want to show how this adds value or how you learned from it. You don’t want to focus on the negative here. It can be easy to slip into highlighting a flaw or a weakness without showing how this actually benefits you and adds value. 

Why the Interviewer Is Asking: 

The interviewer is likely asking you this introspective question to test how self-aware you are. They also might be trying to gauge your openness to discussing your personal flaws and mistakes. 

How to Answer:

You should share some honest experiences but focus on turning negative experiences into positive ones. 

Instead of saying that you're shy, you might consider saying something like,

3. What Is Your Greatest Weakness?

Why It’s Tricky:

While you never want to lie in a job interview setting, you also don't want to reveal a weakness that might disqualify you from the job. If you find that your biggest weaknesses are also a main function of the job, this could highlight red flags to your interviewer. If this is the case, you might need to consider that this isn't the right job for you.

This is where it’s really important to be honest with yourself about the career path you’re on and how you want to move forward. 

Why the Interviewer Is Asking:

The interviewer is asking this question to see if you can be self-critical. This is particularly important if you’re in a role where you must be independent and work autonomously. In this case, you’ll need to analyze your work, your behavior, and your accomplishments to see if what you’re doing is working, or if you need to make adjustments in order to improve.

How to Answer:

When revealing a weakness, honesty and self-awareness are your biggest allies. An interviewer seeks an answer that isn't a canned cop-out (e.g., "I'm a huge perfectionist."). They're looking for a thoughtful, honest answer.

Here’s a three-step process for embracing your weaknesses:

When telling a story, try to end positively. Highlight areas of growth, self-awareness, and the ability to move forward.

4. What Is Your Greatest Personal Achievement?

Why It’s Tricky:

For starters, it’s tempting to focus on personal achievements and forget to tie them into work. We want to keep your answer about work. Make sure your achievements match the job at hand. Your new mortgage might be a huge accomplishment for you personally, but what does it have to do with the Digital Content Director role? 

Perhaps you can share that saving up for a mortgage and researching loans has helped you better understand budgets and financial information. If you can tie this into how you would excel in the role you’re applying for, that’s great!

Make sure your achievements match the skills and experience needed for the job at hand.

Why the Interviewer Is Asking:

Recruiters and hiring managers ask this question because they want to hear real examples of your work. More importantly, they want to learn about your successful projects, the details around them, and how you personally got to the finish line. 

With this question, they can learn about your work ethic, work values, personality, and skills. Did you have to learn to code in order to launch that eCommerce website for your client?!

How to Answer:

When answering this question, use a show-and-tell approach. 

Instead of simply saying, "I increased sales by 600% in one year," describe how you did it. 

5. What Tasks Do You Dislike?

Why It’s Tricky:

It’s important to be honest here. 

However, with other introspective questions, you don’t want to point out a weakness that would deter the potential employer from hiring you. The key is being truthful while also spinning it into something positive, like a learning opportunity you took.

Why the Interviewer Is Asking:

This question is meant to tell your interviewer a bit more about your working style and how you might fit in (or not fit in) for the role you’re applying for.

How to Answer:

Start by focusing on one of the greatest weaknesses you've recognized in yourself. For example, maybe you don't love public speaking. You might say something like, "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..."

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."

6. What Are You Currently Reading?

Why It’s Tricky:

Depending on your reading style and personal life, you might not want to share what you’re currently reading. (e.g., Maybe you’re reading a NSFW novel, or perhaps you’re reading up on starting a family, but don’t want to share that scenario yet.)

Why the Interviewer Is Asking:

Usually, this sort of question is asked to get to know you, learn more about who you are, and build up a personal connection.

How to Answer:

If you’re not much of a book reader, mention some blogs you regularly visit or perhaps how you get your news. “I’m a big fan of morning newsletters where I can quickly get an overview of daily news without being overloaded by information.”

If you don’t want to share what you’re currently reading, take a deep break and maintain composure. Consider sharing a favorite of yours or perhaps a book you often return to for advice or inspiration. 

If you can tie it back to work, great, but sometimes it’s fun to share something totally out of left field. For example, one of my favorite books is Jurassic Park by Michael Crichton, which people usually NEVER expect from me. Not only does it surprise people, but I get to share my enthusiasm for why I love it. It’s so well-written and chock full of science that it really makes you question the world around you and what is possible.

7. If We Gave You a $1 Million Dollar Marketing Budget, Where Would You Spend It, and How Would You Measure ROI?

Why It’s Tricky:

These are what our founder (and former Hulu recruiter), Lauren McGoodwin, refers to as "case study questions."

Why the Interviewer Is Asking:

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.

How to Answer:

This is about showing a clear knowledge of 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..."

8. Can You Explain Your Employment Gap?

Why It’s Tricky:

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.

Depending on the situation, it might be a sensitive or delicate subject for you to discuss.

Why the Interviewer Is Asking:

Knowing a new hire’s background and how this might affect their thought process, perspective, or flexibility within a role is important. 

For example, if you had a personal scenario that led you to have an employment gap, such as an illness, you may have to address this and what kind of support you’ll need going forward in order to do your job effectively.

If you left a job because of a toxic work environment, you’ll want to address what you’re looking for in your next role.

How to Answer:

Especially if you were 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:

9. Why Are You Looking to Leave Your Current Role?

Why It’s Tricky:

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.

Why the Interviewer Is Asking:

It’s important to address what an employee is looking for in a new role in order to see if the candidate and the job requirements align. 

Keep in mind that this question, your response, and how your interviewer responds is just as important for you to take note of as them. If you note that you’re looking for a role where you can work hard to achieve goals while also gaining a better sense of work-life balance, but the interviewer scoffs at this, those are some big red flags for you. 

If you’re confident in your answer, pay attention to the response you get.

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 arises?

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.

You also might answer with something like “I’ve really loved my time at my company, but there’s been a bit of a plateau, and I’m excited about growing in my career."

10. What Does Your Ideal Workday Look Like?

Why It’s Tricky:

This is tricky because there are often subtle work expectations that companies don't discuss. Maybe people don't take lunches, or they stay late a few nights a month to finish big projects.

Why the Interviewer Is Asking:

The interviewer likely wants to see how you work, your ideal situation, and how you might fit into the company culture. Your answer may also show the interviewer how much research you’ve done on the company, which can highlight your preparedness and motivation to do well in the interview. 

How to Answer:

Look for inspiration in the job description!

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.

11. Why Should We Hire You?

Why It’s Tricky:

A danger zone between self-assured and cocky, this essentially amounts to "What makes you so special?" and "Why do I need you?"

Why the Interviewer Is Asking:

Interviewers want to see how you can pitch yourself. Can you highlight your achievements and solve their problems? Can you touch on company pain points and how you might address them? If you have chemistry with the team, this would be a great place to share that!

How to Answer:

Through your research and even the current interview, you should have a pretty good grasp of the company's struggles. Your answer should focus on how you're uniquely qualified to help them tackle those issues head-on. 

12. Why Do You Want to Work at This Company?

Why It’s Tricky:

It’s estimated that 47 percent of candidates fail their interview because they don’t have enough information about the company.

Why the Interviewer Is Asking:

Hiring managers and recruiters also like to dig deep to ensure that you’re actually interested in working for them.

How to Answer:

Do your due diligence and show that you’re interested in the company. Show that you’ve done the research and the company aligns with your goals and your own personal mission. 

Ultimately, this is your chance to show why you want this job and not just any job. Show the interviewer that you’re invested and want to be part of the organization.

13. What Is Your Desired Salary?

Why It’s Tricky:

You want to ensure that you’re working with a salary that is feasible for you, but you don’t necessarily want to share what you’re currently making. It can be tempting to share what you’re currently making, and why can trap you in a perceived salary range.

Why the Interviewer Is Asking:

While it can feel stressful to answer this question, it’s important that everyone is on the same page to ensure that neither you or the interviewer is wasting time if the budget they have does not work with your salary requirements. 

Keep in mind that salary doesn’t always indicate the total compensation package. However, if the numbers are way out of line of your needs, experience, and expectations, it’s likely not worth your time.

How to Answer:

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.

14. Can You Share an Experience Where You Turned a Difficult Situation Around?

Why It’s Tricky:

This is an introspective question that requires some storytelling. You’ll want to be honest about a less-than-ideal situation but show your problem-solving abilities.

Why the Interviewer Is Asking:

This can help the interviewer gain a better understanding of how you solve problems, how you learn from your mistakes, and how you react in challenging situations.

How to Answer:

Creating STAR stories can be especially helpful in answering this question and fleshing out pertinent anecdotes. The STAR method involves outlining a story and breaking it up into the following sections:

If you want more info on telling an effective story using the STAR method, we will walk you through it here. 

15. Have You Ever Disagreed With a Company Policy, and How Did You Handle It?

Why It’s Tricky:

While you don’t want to scare the interviewer by talking badly about a company’s policies, it is important to ensure your integrity isn’t compromised at work.

It can be a fine line about effectively discussing this without badmouthing a company or making it seem like you have general frustrations with authority.

Why the Interviewer Is Asking:

Asking this will likely help the interviewer determine your decision-making ability, your ability to work with others, and if you’ll speak up after identifying an area in need of improvement.

How to Answer:

This might be a situation where you discuss how you worked with others to come to a compromise that benefitted everyone. You can present information about why you felt that something didn’t align with your values, how you brought it to the attention of others, and how you identified solutions to remedy the problem.

Ultimately, you want to show how you helped create solutions to benefit everyone and how you worked through a challenging situation. This could be positioned as a learning experience for everyone involved.

16. Where Do You See Yourself in Five Years?

Why It’s Tricky:

You don’t want to tie yourself to a role for a set amount of time, but you also don’t want to seem like you’re constantly job-hopping. 

Why the Interviewer Is Asking:

This can help provide insight into your goals. It can also be a great way for the interviewer to determine if you’re interested in growing with the company and perhaps even your perspective on the job market or economy as a whole, depending on your industry and job title.

How to Answer:

In this case, it’s a good idea to share some specifics while still leaving room for interpretation or ambiguity.

For example, you might say something along the lines of: