12 tricky job interview questions & how to answer them


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The new job hunt is hard enough. It’s almost a second job from finding open positions, creating custom resumes, developing a portfolio and cold emailing the hiring manager.

Once you’ve landed an interview, you’ll dedicate even more time preparing and practicing potential interview questions.

Everyone wants to ace this last part of the hiring process and put their best foot forward to cross the finish line. However, as Thomas Hübl says, “when trauma is triggered, the past overtakes the present,” and it’s hard to be the best version of yourself.

While there are laws in place that prevent people from asking questions about race, age, religion, age, citizenship, disabilities, pregnancy, marital status, and other topics, interviewers outside of Human Resources can be unaware of these laws.

Additionally, people don’t always realize that a seemingly innocent question can trigger a traumatic experience or emotional situation for the person on the other side of the interview table.

Let’s take a look at 12 triggering job interview questions and advice on how to answer them so you can stay in the moment and make the most out of difficult questions that come your way.

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1. Where are you from?

A common question from social settings becomes a triggering question in a work environment. While used to get to know people at a party, this question has racial and economic undertones and is hard to answer for hyphenated identities and complicated childhoods.

“If you’ve experienced chronic unemployment as an adult or part of your childhood and therefore needed to move around a lot, this seemingly simple question is difficult to answer,” said Robyn from A Dime Saved.

“My recommendation is to give a broad answer to satisfy their curiosity. You don’t need to go through all the places you lived. You can answer by saying where you are originally from or the name of the town you’re currently living in.”

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2. What is your biggest weakness?

This is one of the most popular job interview questions, yet it’s a complicated topic for people with a disability or a disorder.

“They clearly don’t want to know that I can’t say no to junk food, and I don’t want to tell them that I’m a giant ball of anxiety,” says Melanie from Partners in Fire.

“The old advice of spinning a positive as a negative is overused, and I think most hiring managers can see right through it. Being so much of a perfectionist that you stay late every day to ensure everything is correct is trite, and everyone knows it isn’t the truth.”

“Instead, I prefer to use a real weakness, but also explain how once I became aware of it and overcame it, I’m now a  better employee because of it. I’d say something like: My biggest weakness is that I can be a little forgetful.

But since I know this about myself, I take steps to ensure that it never affects my work. I set calendar reminders of important dates, leave myself post-it notes and do a brain dump every night to organize my tasks and to-do lists for the next day. Because of this, I’ve never missed a deadline.”

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3. Do you think you’re a fit for our company culture?

While 94% of executives and 88% of employees believe a distinct workplace culture helps drive company success, this interview question is chock full of us/them undertones.

It can be used in an exclusionary manner. To prepare for this question, look at the company’s Corporate Social Responsibility efforts to find shared values.

“I always respond with fun facts about myself cherry-picked to match what I’ve read about them online. For example, if they hold an annual 5k fundraiser, I mention my love of marathons and the charities those runs support,” says Andrew Kraemer, Founder of Wallet Squirrel.

“Realistically, there are thousands of things you can say about yourself, but narrowing it down to the things you have in common will resonate with the interviewer.”

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4. Why have you bounced around so much?

Long gone are the days of spending your entire career at one company. Many factors lead a person to take a new job. It could be a better opportunity, higher pay, but there could also be many difficult personal reasons why a person needed to switch employers.

“I’m 37, and I’m on my 9th or 10th job by choice. I’m always prepared for this question, and my advice is, to be honest,” said Jeff Cooper from Have Your Dollars Make Sense.

“You don’t want to be seen as a flight risk, so show your legitimate and relatable reasons for leaving previous positions. Interviewers know when you are giving “convenient” answers, so make sure yours comes across as authentic.”

“For example, if you left a job less than a year into it because it wasn’t what you thought it would be, practice an answer that tells a story of how you tried to solve the issue and didn’t just jump ship at the first sign of a problem.”

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5. Why do you want to leave your current job?

This is another common interview question where most intentions are innocent. But if you are trying to leave a toxic work environment, it’s a difficult tightrope to balance.

“Almost every job interview will ask about where you have worked before, so prepare an answer that tells a story in a professional manner,” says Amanda Kay from My Life, I Guess.

“You’ll want to avoid sounding unappreciative of your employer and include what you’ve learned or gained from the experience. If you are concise and can focus on the positives, you can lessen your anxiety about your answer and turn it into a moment to tell a story you’re looking to get across.”

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6. Why did you leave the workforce?

While mothers have been asked this for decades, it’s a potentially triggering question for a broader group of people.

“I left Corporate America when my first child was born, but that was not my only reason. My mother’s cancer became terminal during the same time.

Having to explain that my father already passed and I stepped out of the workforce to help take care of my mother would be a tough story to tell over and over again,” says Monica from Planner at Heart.

“My advice is to find something you’re comfortable speaking to and don’t force yourself to go to an emotionally difficult place while you’re in a job interview. That’s why I stick to my motherhood story and don’t go beyond it.”

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7. What would be your mother’s biggest complaint about you as an employee?

To be creative, some interviewers try to come up with cute or unique questions to get to know a potential team member better.

A question like this could be triggering for so many people. Before you ask them to job applicants, think it through. Perhaps a person didn’t grow up with their mother; they currently have a strained relationship or grew up in a family with two dads.

“This is one of those interview questions that is meant to catch me off guard and incriminate me on a personal level. My advice is to answer a question like this quickly, such as I work too hard and don’t have enough time for her. The answer highlights my dedication but also helps move the interview along to a more productive area,” says Jacqueline from Parent Portfolio.

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8. What’s the worst on-the-job experience you’ve had?

Asking someone to relive a personally traumatic experience is not the best way to understand their character, values, problem-solving skills or grit. When you’re on the job hunt, it can be hard to predict every wild card question you might get. Be prepared to tell a story of a significant problem you faced and how you approached solving it.

“The key to answering this question is to pivot to a positive story about the most challenging on-the-job experience and how you handled it,” says Riley from The Young and The Invested. Demonstrate exactly how you navigated through the uncertainty, stress, or other contributing factors to resolve the situation and to continue working the larger goal.

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9. Are you interested in the boss’ job one day?

Almost everyone is interested in career advancement, but this aggressive question feels like a trap.

“You do not want to answer no and show you lack ambition. On the other hand, if you answer yes, it could imply that you might be a threat. Personally, I would say in due course, I would certainly like to progress in my career. However, at the moment, I want to spend time learning from my peers and my manager about the current job,” says John from Financial Freedom Countdown.

“I’d follow-up by asking them to highlight the top challenge of the senior job. The answer indicates you are ambitious and, at the same time, willing to learn. By asking a question back, it helps turn this line of questioning into more of a conversation. You’ll also get more details about the job you can leverage in the future.”

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10. You’re barely out of college; how are you qualified for this job?

While skirting dangerously close to an age question, try to ignore the negative undertones and use it as a moment to speak to your accomplishments.

“Be ready to share a recent accomplishment spotlighting a skill or experience called out in the job listing. While storytelling is compelling, make sure it’s a data-based example,” says Linda from The Cents of Money.

“Did you identify a cost efficiency or tax credit that saved the company a specific amount of money? Or did you lead an initiative that increased revenue by a certain percentage? No matter what function you are in, having business driving results to speak enables you to land jobs and negotiate for a higher starting salary during the offer phase.

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11. Why should we hire you over the other candidates?

Everyone hates to fail, but for some people, their fear of failure is so significant it can affect their motivation and unconsciously undermine success.

Competition-based interview questions can trigger these emotions and prevent candidates from using this opportunity to highlight what they have to offer to a potential employer.

“When preparing answers for an upcoming job interview, it’s important to keep in mind who is sitting across the table. When answering this question from your potential boss, focus on their needs and highlight your experience and skills that align with what they are specifically looking for from a supporting team member,” says Marjolein from Radical FIRE.

“Similar to the dreaded “tell me about yourself,” this open-ended question can leave you anxiously stammering out an answer. However, it gives you a great opportunity to highlight career results or specific skills not yet covered in the interview,” says Andrew Herrig at Wealthy Nickel. Think of it as your time to shine, show that you’ve done your research, and illustrate why you’re the employee they need.

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12. You have quite the reputation. What’s your story?

While not as welcoming as the common interview question, Tell Me About Yourself, your approach to answering it should remain the same.

“Sharing about ourselves should be the easiest question ever, yet it seems to be one that can trip people up. If you don’t practice, you might find yourself down a rambling rabbit hole. As a teacher, whenever I interview, I share my quick background in the education field, one reason why I chose teaching, and one personal thing such as a hobby,” says Josh from Money Life Wax.”

“My approach to questions like this is to tell a story where I can quickly shift the conversation. I have ready examples of a valuable skill I learned from a specific experience and or how a personal passion for a certain philosophy, like Agile, can help the company reach their goals,” says Adam at Minafi.

This article originally appeared on TheLadders.com and was syndicated by MediaFeed.org.

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Michael Dinich

Michael Dinich is a personal finance expert, podcaster, YouTuber, and journalist. Michael is the founder of Your Money Geek, a rapidly growing personal finance and pop culture website.