Top 10 Tricky Interview Questions & Best Response Strategies

Being asked a tricky interview question that catches you off guard, makes you stutter and try and collect your thoughts as you scramble to give a good answer, is probably one of the worst feelings that you can have in an interview. So to try and help you guys out and avoid this, I went to the career coaches here at Indeed and we’ve compiled a list of 10 interview questions that are typically notoriously tricky, along with answers that you can confidently provide to try and mitigate some of those nerve-wracking feelings.

These questions are either questions about your past performance, your self-awareness in the workplace, or your run-of-the-mill “Gotcha” question. If you’re not sure what I mean by that stick around the end I’ll explain and give some examples of what those typically are and how to look out for them.

Examples of tricky interview questions

So let’s kick things off first by discussing some questions that are really tricky that employers like to ask about your past experience. Now, for context, employers ask about your past experience because they want to understand about your professional offering, how well you know how to sell yourself, and how your history applies to the skills and requirements for the role at hand.

Trick question #1: Why did you leave your last job?

This is a pretty obvious professionalism test at the surface level. I think a lot of people know if you say some really negative things about your former employer in an interview with a new potential employer, that might make some red flags go up on their end.

However, there’s a secondary motivation that employers may have for asking this question, which is to determine how committed you might be to this new opportunity. Hiring is expensive and they want to make sure that you’re a long-term investment. If you left on good terms, great. Speak concisely and authentically about the professional reasons that brought you to looking for a new opportunity, but definitely speak well about that positive working relationship that you had.

However, if the complete story isn’t something that you can sincerely speak positively about, do your best to say what positive things you can, though they may be few, but really to emphasize that it just wasn’t a professional fit.

So one way you could describe that particular situation would be, “It just wasn’t a professional fit but I’m so excited to be interviewing for something that I already know is.”

An answer like that achieves two things. One, you pass that professionalism test with flying colors. And then two, you’re really able to demonstrate that you’re interested in being a committed long-term employee.

Tricky question #2: Why have you changed jobs so often?

Like I said, companies invest a lot of time and money into training and hiring, so they want employees that they think will stick around. So the trick to answering this question is, we can sometimes feel like we need to provide a reason for each and every move that we made professionally, but that is not the case.

You may have perfectly great reasons as to why you left each job, but the more you talk about it, the more space and time this question of changing jobs a lot takes up. Try and come up with a one or two-sentence response that generally explains why you moved around a bit, but bring the conversation back to the opportunity at hand and why you see it as a long-term fit.

For example, you can say, “Right now I’m in the process of looking for a long-term professional home. For a while in my career I took some gigs that I knew would be shorter term at the outset, and there was one other opportunity I had, which unfortunately I lost due to layoffs that the company underwent. However, I absolutely see this role as a long-term investment on my end.”

Tricky question #3: Tell me about a time when you made a mistake at work?

Yikes, obviously this is a not-so-fun question to be asked because we don’t want to provide a mistake that scares the employer away, so what level of mistake is acceptable to disclose? The trick to responding to this question is that managers just want to see that you have made a mistake, you can own it and that you’ve learned and implemented tactics to prevent that mistake from happening again.

So to answer this question, concisely tell a story of when you made some kind of error or blunder, what you learned from it and how you can now approach similar situations differently. This can be a big mistake, it can be a small one, but the important thing is that you take it on your own shoulders, really show that accountability.

For example, you could say, “In my first job, I made the mistake of not proofreading a piece of social copy that went out and actually appeared on my boss’s phone. I, of course, quickly fixed the mistake and from that point on, I learned the importance of creating a system for myself of reading every single piece of social copy out loud, so I didn’t make that error again.”

Pro tip here: Whenever you hear a question that starts with “Tell me about a time when” or “Can you give me an example of..”, these are behavioral-based interview questions. So if you want some advice on how to answer those particular types of questions, there’s actually a whole strategy on it, which we explain in this video right here:

So this brings us to our next type of tricky interview questions, I’ll sort of term these self-awareness questions. But before I hop into those, please if you’ve watched this far, give us a “like”, subscribe down below and turn on notification bell.

So the next category, like I said, is self-awareness questions. And as a general note before we get into the specific ones, it’s important to understand that employers care about your answers to these because if you’re self-aware, you’re able to be coachable, adaptable, and mitigate your emotional responses. All of these are really key things when it comes to operating smoothly in a professional workplace.

So tricky question #4: What is your greatest weakness?

This question, like the one about your greatest mistake, can often make our stomachs sink because we want to put our best foot forward in an interview and here we are being asked to disclose something negative about ourselves. However, the real trick here, the real false answer would be to sort of provide a humblebrag.

We’ve all heard the, I’m a perfectionist response. While that might be true, generally, if you answer something a little bit more vulnerably, candidly, and honestly and show some mitigation strategies, that will resonate more with employers.

The best tactic here is to share a story about a time when a personal trait led you to make a mistake that you won’t repeat. The best formula here is weakness, plus example, plus improvement measures. Really focus on that improvement measure.

An example would be if you tend to procrastinate, share how you came to realize that. And add, “And now I set a deadline of my own before the actual deadline so that I have enough time and I’m not ending up scrambling at the end.”

Don’t revert to sugar-coated weaknesses like, “I’m a perfectionist” or “I’m a workaholic”. These don’t really demonstrate your self-awareness and openness to improvement.

Tricky question #5: What might your current boss say about you?

Woo, this is another tough one. It’s easy to leap into over-inflating what your boss might say. Actually, this is really all about understanding oneself and understanding your ability to empathize with other people in the workplace.

They want to see that you can put yourself in your boss’s shoes, sort of think like that manager. Just be honest about your best qualities at work, even if your boss hasn’t specifically commented on them. You can say something like, “My boss would talk about my accountability and how seriously I take not passing the buck to other team members and creating more work for others.”

So tricky question #6: Tell me about yourself?

Some people may say that this is sort of an icebreaker and it definitely does take that role when beginning an interview people often start here. However, this definitely feels like a tricky question to most people because it’s so open-ended and broad. What is relevant to share, how do I stand out and make a good impression on an interviewer?

The mistake here would be to come across as rambling and unprepared. It’s really important to give a clear and concise elevator pitch. My suggestion is not to just summarize your resume or daily responsibilities. Instead, really connect with that interviewer on an emotional level and then describe your big impacts.

One strategy to make that emotional connection is to describe your “origin story”, and make that quick connection to career goals.

Let’s say you started out in print journalism, but you’ve broadened your career search, you’re trying to make a transition. You can say something along the lines of, “I have been devoted to storytelling ever since I was a child, I loved reading fairy tales. And in college, I was obsessed with romance novels and I’ve loved my time in print publishing. I’ve reviewed x number of books and made a lot of impact there. But I’m really interested in broadening my reach so that I can bring my passion to storytelling on many different platforms.”

If you’d like to learn more about how to answer, “Tell me about yourself” and create that perfect elevator pitch, I highly recommend checking out our guide, it’s right here.

Tricky question #7: Why should we hire you?

When you’re asked this question, the pressure is on. We know we’re supposed to sell ourselves. And I think the mistake a lot of people make here, is focusing only on their big achievements without really thinking about what’s relevant to the employer. The important thing isn’t just to say, “I have so much success and a great track record of being successful.” It’s really to hone in on, here’s how I can help you solve your business needs.

So the trick really is to get into that job description. Figure out what issue is the employer solving by hiring someone for this role, and look at where your past experience and qualifications can overlap and solve that problem for them.

You could say something like, “From what I understand, this job really demands someone who has strong business acumen and great attention to detail. I have a track record of success and the natural traits do both of those tasks very well.”

Tricky question #8: What salary are you looking for?

This is a nerve-wracking question because we don’t want to ask for too little too late, but we also don’t want to ask for too much too soon and scare away a potential opportunity.

The important thing here is to honor that question. We always want to be polite, professional and obliging in an interview, but pivot it back to the employer. At the end of the day, they’re at the advantage when they’re asking this question, because though they’re trained to put pressure on candidates to respond and disclose the number first.

Ultimately, they know the salary, historical data that they’ve offered to people in the past and they know probably what their exact budget is for your role.

You could say something like, “Total compensation encompasses more than just salary for me. I’m still learning about the roles and responsibilities, so it’s hard to say exactly what my expectations are at the moment. But I’d love to know, what have you budgeted for this role?”

It’s pretty much guaranteed that this question will come up at some point during the hiring process. So I’d highly recommend checking out this video right here where we explain how to answer all of your questions about salary.

Now we’re out the last set of questions, which I term “gotcha” questions. These are sort of out of left field or really challenging questions that you can’t anticipate, and the point here is to see how you perform under pressure and whether you can handle difficult or challenging situations with grace and professionalism.

So let’s hop into the first one.

So tricky question #8: Describe how you’d react in a specific scenario in this role?

So employers ask this question because they can’t see you in action. So forcing you into these mental scenarios where they’re testing how you would behave, is the closest they can get.

It’s kind of an unfair scenario because obviously you gain a lot more experience and knowledge, the more you become ingrained into the role. But the important thing here is to really become ingrained and understand the real priorities of the job.

The night before your interview, what’s recommended is to really visualize the day-to-day that you anticipate this job would be and think about what those key metrics are. What is the overall priority? When you kind of create this mind frame of being clearly guided by what the ultimate goal is, you can handle this kind of question with poise by keeping that in mind.

For example, if you’re asked how you would drive sales at a new company, and you know that giving presentations is a big part of the role and you have familiarity with that from your previous job, go ahead and say something along those lines of, “At my current company I give business development pitches at least once a month, and I’m really confident that once they understand these product features, I can craft and deliver compelling presentations very quickly in order to maximize our overall revenue.”

The final tricky question is, just that. A trick question could be challenging trivia or a hypothetical scenario that throws you off guard. Something that more than likely no one on Earth has a confident answer to on the spot.

For example, “How many elevators are there in the USA?” or “What would you bring to a desert island if you could only pick three things?”. All these questions are definitely going out of fashion. They still do occur typically with recent graduates or people with not much experience.

If you’re asked this question or any tricky question, don’t panic. It’s not expected that you’ll be able to accurately estimate the number of elevators in the United States, or you have some perfect survival kit for surviving on a desert island.

It’s really all about explaining your thinking, and showing that you can solve problems well and communicating that.

For example, “I don’t know exactly how many elevators there are in the US off the top of my head, but in order to solve that problem, I would start with an online search, reach out with friends or colleagues who might know more about the topic than I do, and then synthesize that research. And what I’ve learned and depending on how important it is to get really accurate information, I could go beyond that and conduct firsthand research myself. I’d then bring my ideas to my boss to get the best solution.”

And just a quick note here. This piece of advice can be applied, not just to trick questions, but to any question that is difficult or challenging for you. Everything from a behavioral interview question that is really specific and you don’t have a specific scenario to share that matches up. Or it could be a question about a certification that they wanted you to have that you have never even heard of.

All of these things are perfectly fine. We often feel confined to talking about experiences that we’ve had firsthand ourselves, but if you can explain how you would go about solving things, that’s great and extremely useful for an employer.

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