6 Difficult Interview Questions and How to Answer Them

May 24, 2021
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So you’ve landed an interview—congratulations! Standing out in a sea of resumes is no easy feat, but the hiring process is far from over.

Now it’s time to knock your interviewer’s socks off. If you really want to wow, you’ve got to do your homework and be as prepared as possible. You’ve picked out the perfect outfit, researched all there is to know about the company, and printed your resume, but you can’t stop there. What will really get you hired is your stellar answers to the interviewer’s questions—not that super cute blazer (sorry!). We’re here to help and make sure you don’t go into the interview blind!

While the process can be long and nerve-wracking—these are questions that potentially alter your future after all—there are some difficult interview questions you can bet on being asked. Read on, practice, and go crush that interview!

1. Tell me about yourself. 

This is a little like the “What do you do?” question that can be so stressful. It’s asking you to sum yourself up in a succinct but engaging way. You want to grab your interviewer’s attention without delving into your life story. 

What the interviewer really wants to know is a little about your personality, but also what about you will add to this particular company. Do not have a scripted response. This should be tailored for each interview and you should talk about where you are professionally. 

DO talk about why you got into your particular field and how it relates to your background. What it is about your line of work and experience that is specifically “you.” When and where you adopted your dog is cute, but save it for after you get hired. 

2. What is your biggest weakness?

I’m a workaholic. A perfectionist. Type A. I never give up, to a fault. None of these answers the question. Using this question as an opportunity to #humblebrag is not the way to go. Instead, they show that your biggest weakness is an inability to address where you’re lacking and you come off cocky. Everyone has weaknesses, including the person sitting across the table from you, and self-awareness is a good trait.

3. What would your previous employer say about you?

This question needs to be answered based on how you left your last company. If you were fired, and you’ve still listed that position on your resume, don’t try to hide it. Instead, use this question as an opportunity to explain where you went wrong and what you learned. 

If you left your last job on good terms and your former boss is willing to be a reference, this is a great way to back up what you say. 

If you had an exit interview, you can pull directly from that conversation, and is a reason to ask for an exit interview if your employer doesn’t offer one upfront. However, a resume doesn’t have to include every job you’ve ever had. 

That said, be prepared for this one: 

4. Are there any jobs you’ve omitted from your resume?

This is a particularly tough one. If you’ve left a job off your employment history there are usually two reasons: it was a short, contract position (90 days or less) that didn’t add anything but a few extra lines to your resume, or you left on really bridges burned, bad blood, terms.

There are certain jobs we take that are fillers or contract jobs that give us the ability to pay our rent, or brush up on skills (a great point to highlight). Feel free to mention jobs that you took as “in-betweeners.” Even if it’s a job that you think is beneath you and your skills, tell your potential employer about it. The willingness to work while you’re “not working” highlights an ethic to stay on the grind even if you aren’t employed full time. 

If there really is bad blood between you and a former employer, and an interviewer point-blank asks you this question, you don’t want to start a new work relationship off by lying. You can talk about what happened in more vague terms without mentioning the name of the company. As scary as it can be, this is a great opportunity to show your humanity, own your failures, and end on a high note by explaining what you learned. 

5. What are these gaps in your employment history?

This piggybacks on question #4. Sometimes gaps are omissions and sometimes they are simply times when you were unemployed. If there are gaps, be prepared to explain what you were doing during this time. 

If you don’t have an answer because you used your fun-employment time as just that, let this be a lesson: Don’t sit and wait for the job to come to you. The harder you hustle the greater the reward. There’s a good chance that if the job comes down to you and someone who took a class or another job during their unemployment, you’re probably not getting that position. 

The hustle never sleeps or stops—even if you’re not getting paid. You are responsible for your future, no one else. 

6. Is there anything you want to ask me?

If you say, “No, I think I’ve got it,” be prepared to kiss that job goodbye. You just spent 30 minutes with the person in charge of hiring you and if you don’t have any questions, you haven’t done your research. Show that you are willing to go the extra mile (hell, block) for the company. These questions should NOT be about salary, benefits like vacation days, or how long you have to wait for your first performance review and promotion. Climb the ladder sure, but wait until you get hired to take a step up the rung. 

Look into clients they’ve worked with, their greatest successes, and figure out a question or two that shows that your battery is fully charged up for them i.e. not questions that show you’re only looking out for you. These are questions that show you are also willing to go outside of your job “description” and get involved in multiple verticals. 

Good luck and be your best-prepared self. This is your year if you want it.

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This post was originally published on January 20, 2016, and has since been updated.

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