10 Tough Interview Questions We All Secretly Hate Getting

© Adam Gregor / Adobe Stock

Tough interview questions

© Adam Gregor / Adobe Stock

Profile Picture
Amanda Brown12
By now, it’s widely known that tech companies like Google and Facebook have a little black book filled with tough interview questions and puzzles to test the way their job candidates think. Luckily, most of the questions that you’ll receive from a potential employer will be nothing like this.
A quick Google search of “Tough Interview Questions” reveals that most HR departments rely on the same tried and true list of questions but, over time, the wording has changed ever so slightly. Use this list to become familiar with the newest phrasing for interview questions — and prepare the answers to land your dream job.

1. “Tell Me About Yourself.”

This is open-ended ask isn't the toughest interview question, as it's one that many new interviewees are very comfortable answering. Here, the hiring manager is asking you to give your elevator speech. You’ve practiced this a million times, so let ‘er rip. Other ways that you might hear this question include “describe yourself” or “how would a former coworker describe you?” In each of these, the employer is looking for a general idea of how you see yourself. Humble-brag to the max because this is where you want to show your potential supervisor that you can shine and that you know how to advocate for your own abilities and successes.

2. “What’s Your Biggest Weakness?”

Okay, let’s clarify: no one is going to ask you what your biggest weakness is. It’s like verbal clickbait — the manager asks the question and the response is some tacky, rehearsed answer that sounds bad before you even open your mouth to reply. But there are new questions along the same vein, like “what do people often criticize most about you?”
The answer to this question can actually be substituted in for your “biggest weakness.” The odds are good that you’ll give some thought as to how others may see you in a negative light, but you’ll probably also provide some detail as to how you’re trying to improve. It's this ability to self-improve that the hiring manager is really looking for.

3. “Why Do You Want This Job?”

Big red flag here! Do not say “because I’m broke, and I need a job.” Everyone likes to feel special, and this is your chance to tell the supervisor why the company is so amazing. This question — sometimes rephrased as “why should I hire you?” or “convince me to hire you” — is just a test about whether or not you’ve done your homework.
Check out the web and social media pages for the employer, and make sure that you know the ins and outs of the products that they make, the culture or “vision” that they ascribe to and what the hiring manager needs from this position. The correct answer sounds something like, “I have [taken professional training/received education/gained experience] developing the skills that you are looking for. This company is amazing because [something meaningful about culture/vision], and I believe that my ability to [list skills here] makes me a unique fit who can contribute to this company.”

4. “Where Do You Picture Yourself in Three Years? In Five Years?”

This open-ended question continues to be used in the interview because the supervisor hopes you will talk about your excitement for this position and where you hope it will lead. If you’re coming in as an entry-level associate, talk about running your own team someday. If you’ve been hired to work on or manage a specific project, talk about new ideas that you might like to implement once this project is complete.
Heads up: this question can also be framed sarcastically, as in “if I hire you, are you going to try to take my job?” Bring the focus back to your career goals — there’s plenty of room at the top, and by the time a promotion is in your sights, your manager may have gotten one herself.

5. “Tell Me About a Time You Failed.

This question can also be worded as “describe a decision you made that was a failure” or “tell me what you would do differently with your career if you could start over.” Personal questions like these are about overcoming adversity. Believe it or not, work is… work. Sometimes, things don’t go according to plan.
The interviewer wants to know that when you’re on a deadline and projects get tough, you’ll push through it and, if applicable, that you will learn from your mistakes and ensure that it doesn't happen again. Some personality types take failure very personally, but this is an opportunity to show that you can focus on the positive.  Recognize that failure happens to everyone and show that how you deal with it is what separates you from other candidates.

6. “Describe a Situation When You Didn’t Work Well with a Supervisor or Coworker.”

The way that you answer this question tells a manager how you might deal with conflict and whether your reactions would work well in the manager’s team. There’s only one wrong answer here: “I’ve never been in this situation or had a disagreement with a colleague.” Everyone, even the best of friends, has disagreements, so to deny that you’ve never had this experience sounds disingenuous. Be honest, and describe a time when you had a different opinion about how a project should be tackled.
Next, either explain how you defended your preference and won or how you lost and saw the merit in someone else’s suggestion. Other phrasings for this question might be “tell me about a time when a coworker wasn’t doing their fair share,” “when you have two projects that need your urgent attention, how you decide which gets top priority?” or “who was your best/worst boss?” This is about looking objectively at the situation and being able to make a thoughtful, ethical and professional decision.

7. “Tell Me About Your Last Employer or Supervisor.”

This is a bit different from the last question in that it’s easier to focus on the skills and abilities you cultivated during your last work or educational experience. Also framed as, “describe your experience in a team or collaborative setting,” this can be a great opportunity to highlight your relevant experience while showing that you can give credit to others. For example, explain how your most recent manager helped you with a difficult task or assignment that went on to succeed, or explain how the projects and assignments that you were given helped you learn a meaningful career skill.

8. “So, What Do You Do for Fun?”

Also known as “how do you deal with stress?” If the job that you’re interviewing for is in a region of the U.S. that is well-known for a specific recreational activity, you can do a little bit of sleuthing into the company’s social media pages and give an answer that shows that your extracurriculars match the interests of your coworkers (and that you would fit well in the company culture). Skills are important, but a personality fit is also essential for team cohesiveness.

9. “What Are Your Expectations for Salary?”

We can’t have a list of tough interview questions without bringing up the necessity of negotiating your salary. In a world where women aren’t always equally compensated for their skill set, this question must be answered — though, if you’re not comfortable answering the question at this point, the best answer to give is that you expect your wages to be “fair and competitive compensation.” You can mention that you’d like to know more about benefits and specific job responsibilities before you start talking numbers, and that you’re focused on the opportunities of this position rather than the starting salary. (For real though, when you get the job offer, negotiate like a boss.)

10. “Do You Have Any Questions for Me?”

Uh, yes! Asking the HR recruiter your own questions shows that you’ve been paying attention and that you're interested in the position. If you’re having trouble coming up with something, stick to general questions that work for almost any occasion: “is this a new position or a replacement position?” “How many other people will I interact with on a regular basis?” “How long has my direct supervisor been a manager?” “What is it like to live here?” “Can you tell me more about your expectations for [list a job responsibility that you’re not so confident in]?”
It’s important to remember that there is no right or wrong answer for most of these questions. The hiring manager, HR recruiter or supervisor is looking to fill a space on their team and they have a specific skill set and personality in mind as they’re interviewing you. Be yourself, and you’ll land a position that hires you for who you are and what you can do.
*Before you go, you might be asking yourself: what’s the answer to the airplane question from the beginning of the article? Well, there are multiple answers, since there are several different ways to calculate weight and the contents of the plane will add to the final total. (FYI: this is why we calculate the weight of luggage.) But, by far, there is one answer that I have received overwhelmingly: read the manual.
Still on the hunt and looking to land the interview? Check out these resume skills you should NOT forget to include, or for ways to shine in the new workplace, try 10 Ways To Be Unbeatable In The Office.

Don’t miss out on articles like these. Sign up!

Jane Scudder is a certified coach & workshop facilitator. She also works as a strategy & marketing consultant and teaches a Career Development & Preparation course at Loyola University Chicago. She lives and works remotely in Chicago, IL. Learn more at janescudder.com.