How to Answer More Challenging Interview Questions

Updated: Dec 15, 2021

Interviews always end up being a little stressful. Even if you have all the necessary skills, qualifications, and experience you’ll always have a few nerves lurking at the back of your mind. The area where a lot of candidates tend to short in in interviews is with some of the more tedious questions you are likely to be asked. The type that you never really know exactly how to answer and just stumble though, hoping for the next question. If you want to know how you can tackle some of these questions, here are a few ideas for you that might help you push ahead of other candidates.

There are lot of things that you can do to prepare for your interview, but before getting into specific questions it’s worth mentioning the S.T.A.R. method (Situation, Task, Action, and Result). Created by DDI (Development Dimensions International), it’s a simple method that gives candidates a structure that they can use to create the best possible answer they can. When creating your response, the first thing you need to do is think of a relevant example. Bringing up something that won't back you up for the role is a bit pointless and you just end up wasting the question. Then, using the example, work though each point of S.T.A.R. and construct your response.

How Would You Describe Yourself?

This is the question that most people dread, but this is a great question. It allows you to take a little more control of the interviews direction and bring up skill, experiences, and/or qualifications you want the interviewer to take into consideration. You can highlight the strengths and skills you have that make you a stronger candidate that may not have otherwise come up in the interview. For example, if the role requires you to be creative there may have been a time where you volunteered to help with an out of work event that required you to come up with original ideas. This would show off your creativity while also showing that you are a self-starter with the motivation to get stuck in.

What Is Your Greatest Strength?

The biggest problem with this question is deciding which quality you want to pick out as your greatest strength. There will be a lot of things about you that will stand out and make you strong in your own way but is it relevant. Pointing out that you are highly analytical when the job requires you to be creative and channel ideas doesn't make you look right for the role. So, talk about something that makes you look like a good fit, even if you are not directly talking about the job.

What Are Your Greatest Weaknesses? / What criticism do you most often receive?

While both questions make the interview seem like more of an interrogation – wanting to know everything bad about you but that’s not their goal. When they ask about your weaknesses, they want to see how aware you are of yourself. They want to see if you understand where you need to improve and how you are doing it. When answering you need to pick out a weakness, why it is a problem, and what you are currently doing to improve.

Again, these questions are similar, but the difference is what the interviewer is trying to find. With this they are trying to find how you handle criticism. If you can take it and use it to improve. This question can easily be answer by just using an example and talking about a time where you received criticism and used it to better yourself.

Tell Me About a Time You Have Overcame an Obstacle.

This is a good way for the interviewer to gage how you handle running into a problem while you are working and answering it is similar the last question. Think of something that is work related (preferably), describe the problem & what was at stake because of it, what you did to resolve it, and then you can wrap it up with the outcome - which really should be positive to end on a good note.

What Would You Say Is Your Greatest Achievement?

Interviewers will ask this to try and determine what you consider to be valuable. Answering this is easy, talk about something that you have done recently that is also relevant to your career, talk about the situation, what your role in it was, and why it was so valuable to you. It doesn't need to be a long expatiation - it's better to just keep it short and sweet.

Why Did You Leave Your Last Job?

This allows the interviewer to gain a lot of valuable information about you and how they can accommodate you if they feel that you are a good fit for their company. Knowing the deal breaker in your last job will allow them to tailor them to give you a better deal and understand what you want in a job, whether that is in the benefits, the pay, the people, etc. It's important that you don't speak negatively about your last employer and job, even if it was a terrible experience. All it does is reflect badly on you. Just talk about it in a clear and neutral manner and avoid giving away too much personal information. It's just not needed nor is it professional.

Why Do You Want to Work Here?

When producing an answer, try to flip the question around. Instead of "why do you want to work here?" think "why would this company want to hire me?". Think about how you can make a positive impact on their company and how it would benefit them to have you. This is a good opportunity to show how much research and thought you have put into your decision to pick their company. If you know what is currently happening in their industry/business and what you would do to help them improve if you were a part of their company.

Why Should We Hire You?

It is a deceptively simple question that half the time elicits a generic and boring response from most candidates, something along the lines of " I feel that I have all the experience and knowledge needed to fulfil this job successfully." which would be all well and good if they didn’t hear it from every other candidate. It just makes you seem like you’re trying to avoid the question and you’re just trying to gloss over the question without much thought.

When not doing the latter, most people will end up being either too confident or too humble. When creating your answer come up with a few specific skills & qualifications and then think of an example you can use to justify it. It's all well and good saying that you have all these amazing qualities but if you have nothing to back it up then it doesn't really mean anything to an interviewer. You also need to find that balance in the middle of the two. You need to seem likable, self-assured but not egotistical or they'll feel that you won't work well as part of their company.


Hopefully, this will help you to gain a little more confidence and clarity when it comes to answers some of the more difficult questions you may encounter during an interview. Having an idea of what you want to say and how you can say it before you're put on the spot is always an advantage.

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