Job Interview

12 Tough Interview Questions and Answers to Them

tough interview questions

“OMG, that was the toughest interview of my life!” — you’ve just read someone’s comment about the company that called you in for an interview. And the panic starts kicking in. What type of tough interview questions could they possibly ask?! Should I get worried? Too late, I AM worried now! 

Sounds familiar? In that case, this guide will help you contain your panic and get prepared to answer all sorts of tricky interview questions with confidence! 

What are Some Tough Interview Questions and Answers? 

Tough is a subjective criterion. Some people may feel intimidated by weird interview questions, requiring instant wit and a tad bit of humor. Others may get gobsmacked by hypothetical interview questions, asking to model your actions for a certain situation. 

Overall, most candidates find it hard to come up with a good answer to interview questions about their weaknesses, gaps in employment, reasons for leaving a job, and things they disliked in the past organization. 

So why do HRs love to throw in a “loaded” question once in a while? No, it’s not to make you trip or anything, but rather to assess:

  • Your levels of emotional maturity and personal resilience 
  • Ability to stay coherent and confident under pressure 

The above two qualities are crucial in the modern workplace. Therefore, you should get prepared to graciously navigate some of the trickier questions. 

12 Tough Interview Questions and Best Answers

As the old adage says, the best defense is offense! The below list of sample tough interview questions should help you get well-prepared for the actual interview! 

1. What You Didn’t Like About Your Last Job?

As you probably know, blatantly badmouthing a former employer is always a bad idea. Why? Because it shows you in less than positive light. A person, who’s quick to bash the other party (especially without some serious proof) is rarely seen as trustworthy and reliable. 

So don’t go all confessional here, reciting all the reasons you hate your current job. Stay tactful and polite. Acknowledge one issue — preferably operational or strategic, rather than people-related — and summarize it. 

For example: 

“My company was a bit behind on the digitization trend and our local ERP system didn’t connect well with another branch. Because of that, account payable reconciliation was largely manual tasks, also requiring frequent meetings. Personally, I found it rather ineffective and brought up the issue several times with the IT department. Yet, it is still unresolved at present.” 

2. What Type of Criticism Did You Receive in Your Last Position? 

This question probes your ability to handle constructive criticisms — a must-have skill for successful teamwork. Every employer wants to make sure that they are hiring a well-rounded adult, capable of understanding their shortcomings and missteps. Show that you are indeed emotionally mature and respond well to all sorts of feedback.

Tell a quick story like this one: 

“I spend 2 months working on the new sales copy for a new app. But during the presentation, the Product Team said it lacked reliability. Specifically, the manager told me it lacked the voice of customer data and provided me with some quotes from recent interviews. I then gave it another go and everyone loved the new version.” 

3. Do You Regret About Any Career Decisions You’ve Made? 

By asking this question the HRs try to understand whether you are truly motivated by the current line of work you do. Or perhaps you are still not sure about the trajectory of your career path. It’s okay to admit you’ve taken some detours.

For example, you can frame your reply like this: 

“Can’t say I’m very regretful, but I really wish that I’d transitioned to UX design earlier. I started learning and experimenting on my own back in 2018, plus did some part-time freelance consulting. But only in 2020 when I joined Acme Inc as a Junior UX designer did I realize that this is the niche I really want to grow in professionally.” 

4. Are You Interviewing with Other Organizations? 

Some people get stupefied by the directness of this question. But the best strategy is telling the truth. If you are interviewing, just say “yes” and vaguely mention which organizations (e.g. another real estate development company). 

If you are not, it’s best not to lie. Some HRs are good at reading body language and may notice you being dishonest. 

Sample answer: 

“Not at present. Your company actually got to me rather fast and since I really liked the job description, I haven’t yet sent my applications to others”

5. What Do You Think Our Company Could Do Better? 

This question checks if you did some pre-interview company research (which you absolutely should!). Also, it’s often asked of candidates going after managerial and exec level positions to test their analytical abilities. 

So try to come up with some interesting suggestions, based on the light digging you’ve done. 

For example: 

“I’ve noticed there was quite a lot of negative publicity around your recent product launch. Consumers on TikTok were really frustrated about excessive packaging and the low use of sustainable materials in the recent advent calendar. I think one way to get out of this would be by making a public statement about all the CRS activities your company does and perhaps donating a % of sales from the advent calendar to the “Plant a Tree” charity.” 

6. How Do You Deal with Workplace Conflict? 

Most employers view soft skills as important as hard skills. That’s why many popular interview questions are aimed at deciphering your personality. Are you easy to work with? Can you mediate issues among others? Illustrate your interpersonal skills with a quick story. 

Sample answer: 

“Occasional disagreement is part of any teamwork. So when I feel when the discussion gets heated between my team members I usually put on my mediator’s hat. First, I give each party an opportunity to voice their concern, but highlight that we never are to put blame on someone, just state the facts. Then offer the other party an option to express their point of view. Afterward, I try to suggest the next best steps for resolving the issue and moving on to more productive stuff’. 

7. How Successful Do You Think You’ve Been in the Previous Role? 

This interview question can seem tough for people, who lack self-confidence. Surely, throwing a blanket statement like “I was the best on the team” without any further proof won’t look good. But neither does diminishing your accomplishments and contributions. 

When answering this question, don’t just rate yourself — provide facts. 

For example: 

“I believe I did pretty good. My average customer satisfaction score per ticket was 97% and I managed to resolve 85% of customer queries on the first attempt, without escalating them to senior CS representatives. My colleagues also upvoted me as the “Most cheerful rep” in last year’s New Year competition. That also counts, right? :)”  

8. Don’t You Think You May be Better Suited for Another Type of Company? 

This question indeed is quite tricky. It’s meant to test your confidence levels a bit and prompts you to further discuss why you want to work for this company. So do just that.

Sample answer:

“I assume you are asking this because my educational background is in Political Science? Indeed, I used to work as a staff member for political campaigns, but this line of job had a pretty hard mental toll on me. So I have transitioned to working with NGOs. Joining Samsonian Foundation seems like a solid next step for me as it would not just provide me with the space to exercise my strong campaigning and fundraising skills, but also work more closely with the performing arts sector. What my resume didn’t tell you is that I’m an avid musical theater fan and also do some modern dancing on the side as a hobby.”

9. Have You Ever Been Fired? If So, For What Reasons? 

There’s probably a reason why an employer asks this question. They may be concerned by the employment gaps in your resume. Or just wonder why you’ve changed quite a few jobs in the past. So you’d have to provide a plausible explanation. For example, you’ve changed careers, had to move, or was a stay-at-home parent. 

Yet, you may have indeed been fired once (or even twice). In that case, it’s best to be forthcoming about the issue and acknowledge why this happened, what you’ve learned, and how you plan to do better at this job.

Your answer can go like this: 

“Yes, I was fired from a bartending gig at Metropol Hotel. During one rushed and crowded event, I was accidentally pushed by a rushing server and spilled a drink all over a guest. Despite my profuse apologies and a proposition to pay her dry cleaning bill, she still demanded the management to terminate my employment. Since her husband was an investor in the hotel chain, I was indeed fired”. 

10. Why Our Company, Not a Competing Organization? 

In this case, the recruiter wants to probe you for potential loyalty. They also try to understand your feelings towards the competition. By no means, you should bash the “other guy”. Instead, sum up several points that really appeal to you in this company. 

Sample answer 

“I’d say three things. First, I’m a big fan of your CEO. In a recent Wired interview, he explained his stance on customer data privacy and how it’s reflected in the company policies. I share this sentiment too. Secondly, I think your public product roadmap is moving in a better direction than that of Gram app. You are not as obsessed with adding as many premium features as possible, but rather seek to create extra value opportunities for users. Finally, your Coding for Girls classes are an amazing initiative. I want to see more women in STEM too and would be happy to serve as an instructor”. 

11. How Long Do You Plan on Staying with Us?

Employee turnover is a “given” for many industries. So some companies want to make sure that you are not viewing the current role as a “pitstop” until some better offer arrives. At the same time, saying that you should be content in this role for another decade won’t sound too plausible either.

So try to be diplomatically honest  and say something like: 

“I know a retail associate is an entry-level, high turnover job. So this isn’t something I’d want to do forever. But I really like Salty as a brand and could see myself staying with you after completing my degree in marketing at an office-level position.” 

12.  What Salary Would You Like to Receive? 

The “money talk” doesn’t come easy for many people. Especially, since most are expecting the employer to make an offer and negotiate it from there. 

But if the recruiter presses you to give a number here in now, you should say something like:

“I researched the role before the interview and found that the typical salary within your company is around $60,000-$75,000. That’s roughly in line with industry standards, and it’s a range that I’d be open to considering”. 

Learn more about negotiating a salary during an interview or watch this video:

Any interview question is only as tough as you perceive it to be. Don’t get buried too deep inside your head, stressing over all the possible tough interview questions a recruiter can drop on you. Instead, think about your main strengths. Then practice framing answers to the above questions in a way that lets you showcase them! 


  • Elena Prokopets

    Elena runs content operations at Freesumes since 2017. She works closely with copywriters, designers, and invited career experts to ensure that all content meets our highest editorial standards. Up to date, she wrote over 200 career-related pieces around resume writing, career advice... more

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