How to handle tricky interview questions

04th May 2021

Top Interview Questions

For the typical job interview, there is the run of standard questions that provide a solid foundation for the assessment of candidates. These are the basic questions that can be asked during a job interview. Things like:

  • Describe your strengths?
  • What do you think your weaknesses are?
  • Why do you want this job?
  • What made you apply to this company?
  • What were the responsibilities of your last position?  
  • Why are you leaving your present job?
  • What do you know about our company? 

For those attending an interview, these are the questions that are fully expected and are relatively easy to prepare for. However, once the basics are out of the way, the interviewer will want to find out information that goes a bit deeper. The majority of interviewers know that their basic questions will have been prepared for, therefore, will want to ask some that will not have a rehearsed answer. 

What other kinds of questions might I be asked?

During the interview you can expect the conversation to move away from the standard form of interview questions, and pose ones of a situational nature, like

  • Describe an incident where you and your team were in disagreement. How did you explain your position and reach a collaborative understanding?


  • Describe a time when your work was criticized and how did you resolve it?

 The interviewer’s job is to assess your skills and talents against the position that is being offered to determine suitability. The way to accomplish this is by asking questions that paint an overall picture of the candidate.

Even though these questions can be a bit more difficult to handle, they have become part of the typical interview process and most interviewees that are seriously job seeking, are prepared for them.

What are tricky interview questions and why ask them?

By now the interviewer should have an understanding of the candidates abilities, and how their skills, education, and knowledge aligns with the job. At this stage, they will know whether the job seeker is a viable contender for the position being hired for. The interviewer will want to find out more, and will strive to learn more details about the candidate.

This is where tricky interview questions can delve deeper and yield information that normal questions don’t provide. There may be questions asked about what your guilty pleasure is, or who was the worst manager you ever worked for. Some interviewers even ask seemingly random or unrelated questions like ‘What would your superpower be?’

These unusual questions can also come out of the blue at any point in the interview to catch the candidate off guard. This is not to trick or deceive, but by catching the interviewee when they least expect it, an unprepared and honest response usually follows. 

How to handle tricky interview questions

Preparation is the best defence against unusual or tricky interview questions. Although it is impossible to prepare for every single question, there are ways to reduce the impact of being caught off guard. 


Understanding why such questions are being asked, and knowing that the interviewer is simply trying to gain insights into personality or skills can help. 

Tricky interview questions fall into categories such as:

Personality assessment

"How would your enemy describe you?”

Logic reasoning or problem-solving

"How many elephants can you fit in a car?”

Persuasive ability

"Explain how you would convince a non-believer that climate change is real?”

Questions like ‘Why is a manhole cover round?” or "Why is a pizza box square?” have been popularized by companies like Microsoft and Google. Facing questions like this, while daunting, can provide a chance for candidates to present a clear and rational response. 

For example:

‘Pizza boxes are square and flat for easier stacking storage and transportation. It also means they are cheaper to manufacture.’

‘Manhole covers are round as tunnel shafts are commonly round and the shape allows for easier alignment.’

Being able to understand the logic behind each question will mean that you can provide an articulate and definitive answer. The key is not to panic, and to provide an intelligent and well thought out response that is based on facts or logical reasoning.