The 5 Toughest Questions You’ll Be Asked in a Job Interview

Incoming Hurdles

You’ve sent in your CV, you’ve passed the required tests, and now you’ve progressed to the interview stage! Congratulations, but the journey to getting a job is not over yet – in fact, the hard work’s just about to begin.

Obviously, the employer sees great potential in you if you’ve reached this stage. With that being said, however, their objective is to find out exactly who you are, what makes you different from other potential candidates, and what you could bring to the company if they were to hire you.

As such, they are likely to ask you extremely specific and difficult questions. In return, you will need to formulate clear, concise and well-thought out answers.

Train Yourself

To prepare yourself in advance, familiarise with some of these common yet tough questions, then think about how you will answer them (with the inclusion of examples to support your answers):

1. What’s Your Biggest Weakness?

Acknowledging your greatest weak spot during the interview shows that you possess self-awareness and honesty, and that you’re also willing to learn and/or improve. However, you don’t want your weakness to come off as a “red flag” or a liability, which could damage your chance of getting the job.

For example, answers such as “I was fired from my last job” or “I don’t like working with others” without elaborating on these can make the interviewer think badly of you. It also appears to them that you’re not willing to improve your skills or workplace attitude.

Instead, frame your answer in such a way that you’re taking measures to address your weakness, eg. “I used to take on too many tasks at once. So, in a bid to improve my time management skills, I try to prioritise the most important tasks and delegate the remaining ones to my team.”

2. Why Do You Want This Job?

Alternatively, this question could be phrased as “Why are you leaving your current job?” or “Why do you want to work here?” In any case, the gist is the same – the interviewer wants to know why you’re making the switch from your current job position/industry, and if you’ll fit into their company’s culture. Plus, they want to see the thought process behind your applying to the company in the first place.

When formulating your response, remember to highlight your skills and experience, and how these make you the best candidate for the vacant position. Bear in mind that you should also refrain from criticising your current/former employer, as this can raise doubts about your work quality, productivity and attitude.

For example, if you are a mid-level IT specialist who is applying to a more senior position, mention how you have accrued advanced technical skills and how you managed to apply these at your current company – assisting in maintaining company systems, updating software, analysing data, etc. – albeit to an extent. As such, make mention that the aforementioned vacancy will allow you to utilise and develop these skills further.

3. How Do You Handle Conflict or Stress?

Effective employees are mostly flexible, resilient and keep cool under pressure. They tend to cope better in high-stress situations, maintain focus, and look for ways to solve problems and assist others where they can.

They are also empathetic and possess strong communication skills, all of which are beneficial when conflict between co-workers arises.

If the interviewer asks you this question, they want to find out if you possess these attributes. Vague or stilted answers such as “I told my boss to resolve this issue between my co-worker and I” or “I only helped out on a last-minute task after I completed my other duties” will only put you in a bad light, as it will make you appear unorganised, incompetent and irresponsible.

Instead, drawing back on one of your previous experiences, frame your answer like this: “While working on a design project with my peers, there was a breakdown in communication whereby I was not notified to review the designs, thus the designs were approved too late and we missed the deadline. I took this person aside and we discussed it in private.

“Since then, we have devised a solution: we now keep each other in the loop via emails, text messages and/or phone calls before, during and after the project production process. This way, similar problems that do arise can be resolved in a timely manner.”

4. What Major Obstacle Have You Overcome at Work?

Similar to the above question, the interviewer wants to get a feel of your managerial style, to see how you handle difficult situations, and to gauge if you’re capable of overcoming future adversities at their company.

Again, you need to draw upon one of your previous experiences. For example, filling in for a co-worker who was suddenly fired and being able to stay on top of your increased workload is demonstrative of strong organisational skills, flexibility and fortitude.

Another good example could be about how you put together a company event. You want to demonstrate to the interviewer how you utilised your organisational and communication abilities (ie. establishing a budget, booking your venue, recruiting and training volunteers, staying in the loop with decor suppliers and caterers, etc), as well as how you handled various challenges along the way (ie. meeting deadlines, developing a risk management strategy, revising a bungled menu so that it falls within Halaal or Kosher standards).

If you’re an entry-level worker, it’s acceptable to answer this question using a specific, personal life experience. This serves two purposes: its emotional impact can leave a lasting impression on the interviewer, and it shows them what you learned from this experience (and how you plan to incorporate this into your working life).

For example, moving to another country as a child meant having to learn about a new culture, learn a new language and make new friends. Thanks to your innate curiosity and a desire to learn, you were able to pick up additional knowledge fairly fast and settle comfortably within a new environment. As such, you are able to adapt quickly and are equipped to learn new skills with ease, attributes that the interviewer may just be looking for.

Remember to be as brief and concise as possible – it’s easy to ramble on when answering this question!

5. What is Your Greatest Achievement?

Being asked this question allows you to demonstrate the value you can bring to an employer. Of course, there are probably a myriad of accomplishments that you wish to expand on. For the interviewer’s benefit, though, you should preferably focus on the most important and/or recent one.

When unpacking this achievement, remember the following: describe the context in which it occurred; explain the challenges you faced and the actions you took to deal with them; and state what the outcome was and if it met your goal. All in all, you need to convey why this achievement is of significance to you.

For example, perhaps while working as a mid-level sales representative, your greatest achievement was increasing sales in an underperforming region. Determined to not let your company cut ties with that region despite making huge losses, you temporarily moved to that region, researched why your product was underperforming there – from collecting feedback from locals to observing their shopping habits – and then staged public demonstrations on how to use the product.

Ultimately, you created awareness around the product, sales increased and that region became your company’s top market. As a result, you were promoted to senior management.

By outlining an achievement such as this, you will paint yourself as the most suitable candidate for the vacant position.

A Sprint and A Jump Away From Success

Now that you’ve familiarised yourself with these questions, practise your answers several times beforehand so that you sound confident, positive and relaxed in the actual interview. Take your time before you answer, as you want to avoid sounding nervous or rushed. Best of luck!