Career & Side Hustle Coaching For High Achievers

The 5 Hardest Interview Questions (And How To Answer Them)

The 5 Hardest Interview Questions:

It can be hard to anticipate what kind of interview questions to expect in a job interview. They can vary quite a lot depending on your role and industry, but there are a few types of interview questions that always remain the same. Employers are always looking for employees that can work well with others, learn from their mistakes, and demonstrate why they are they are the best candidate for this role.

I am an analytical person, so before every interview, I like to prepare for it by studying all the questions possible. I’ve even created an Interview Questions Study Guide to help me with the process (click here to download it for free!). And as someone who has been both the interviewee in many industries and many different occasions and the interviewer, these are the hardest (and most common questions) that you find in a job interview.


1. Tell Me About Yourself.

Almost every interview will start with this kind of question. It may not always be phrased this way, but it’s your chance to give the interviewer a quick summary of your work experience and get to know you. Most interviews start off with this question and it is your opportunity to start off your interview with a great impression. Many times, interviewers can determine in the first 5 minutes whether or not they feel you will be right for the role and it can affect their judgement for the rest of the interview.

If you don’t provide a great overview right off the bat, they may dismiss you as a potential candidate to a short-list. “Tell me about yourself” is a very open-ended interview question, and to be honest it can lead to a lot of interpretation. Many people make the mistake of answering this interview question too personal, or not personal enough. Alternatively, some candidates don’t view this as an “important” question so they rush through it, and some people get very nervous (which I totally understand) and start to ramble about irrelevant details.

So how do you answer this type of interview question? Use the PAWS (Profile, Academic, Work Experience, Skills) technique.

Last month, I led a job interview clinic at my alma mater university and this is the best method to answer this question. This is how employers these days are evaluating this type of question. So let’s walk through how to answer it:

P – Profile. This is your chance to outline your professional profile. Start with your name and your current job title/professional designation and then add in any relevant information about professional memberships, personal interests (only as it relates to the field like you love numbers/computers etc.,) and any community involvement that you might have related to your field.

A – Academic. Outline your degrees and certifications. However, don’t limit yourself to just your formal education, include any additional workshops, courses, or training that you have that might be relevant to the job. However, make sure it’s relevant to the position. If you have varied work experience, you do not need to outline education that does not pertain to the job.

For example, if you have First Aid training, while that’s great and something you can add to your resume if you’re applying for an office job, that’s probably not relevant. Lastly, keep it recent and relevant, no one needs to know what high school you graduated from – that’s a given if you’ve completed post-secondary education.

W – Work.Provide an overview of work experience and remember that it can include both paid and unpaid work experience.

S – Skills. This is the section that everybody forgets! Job candidates talk about their personal and professional achievements but they forget to talk about what skills they developed! A candidate’s skill set is an incredibly important part of any job interview.

Most likely, your new job will not be exactly the same as your current job, so employers want to know what kind of skills you will be bringing to this new role. Highlight both your relevant technical and soft skills. What kind of software are you proficient in? And what kind of soft skills will be important to this job? For example.: Time management, client service, negotiating skills, etc.

After you finish talking about your work experience, lead into the skills portion by saying something along the lines of “And in these roles, I developed X skill” and expand on your answer. Do not forget to answer the skills section!



2. Tell me about a time you made a mistake or experienced a failure and how you dealt with it.

Everyone makes mistakes. Especially when you are hiring a brand new employee, it is kind of expected that they will make a mistake at some point, and that’s okay. We are all human. However, it’s more important how you bounce back from a mistake. When answering this question, the most important thing to remember is to choose your mistake carefully.

So how do answer this interview question?

First of all, use the STARR method. Describe the Situation, your Task, the Actions you took, the Result, and how it was Relevant to your job or career.

Next, make sure you carefully choose your mistake. We all make mistakes in our day-to-day jobs, but try not to choose a mistake that’s too close to the job requirements as it might position you as a liability in the future.

If possible, try to choose a team mistake. Do not blame your colleagues, but position it as an error you made collectively such as “Your team didn’t clearly understand the client’s needs, and you made the mistake of not re-checking with the client their expectations of the product.”

If anything, choose a mistake that allows you to frame it as a learning experience. That is ultimately what the employer is looking for. We all make mistakes, but if you take ownership of it, correct it, and learn from it, then that is what will impress the employer the most.



3. Describe a time you dealt with a difficult colleague and what you did.

In every workplace, there will always be a difficult coworker. The employer wants to evaluate how you deal with conflict, and this again is a very hard interview question because you have to choose your answer carefully.

First, start by framing your answer using the STARR method by outlining the Situation, Tasks, Actions, Results, and how it is Relevant.

Next, choose a situation where you demonstrated a level of understanding or empathy. It may be tempting to tell your interviewer of a colleague who was lazy or difficult to work with because they had a horrible attitude, but this is not the time to make your former colleague look bad. The hiring manager will not care about that. What they do care about is how you go about dealing with a difficult co-worker.

What they want to hear: You can work with all different types of people and can resolve conflict on your own.
What they don’t want to hear: That you go to your supervisor regarding every difficult situation to complain.

So choose a situation where you were able to solve the conflict without going to your supervisor to file a complaint. Demonstrate that you have problem-solving skills and try to find a situation where you were able to help your coworkers through a difficult situation. For example, you could talk about a coworker who was always late on their deadlines. And instead of just complaining about them, you spoke to them to find out the root of their problem – perhaps they had some personal issues at home or they struggled to use the software effectively. Finally, you can end the answer with your best foot forward by telling them how you were able to help them.

Always try to end the interview question with a positive answer.


4. Why did you leave your last job?

This can be a tricky interview question. Of course, it’s obvious that you are not happy in your current position because you are seeking a new job. When answering this question, remember the most important thing is not to bad-mouth your previous employer or job. There could be a variety of reasons you’re looking for a new job – you’re looking for a career change, you’ve just moved to a new city, you love the company and their mission statement, or if anything, because you are looking for growth opportunities. Be honest about your reason but make it a positive answer.



5. Why do you want this job?

The absolute biggest mistake that I see candidates make when answering this question is that they focus solely on themselves. While the entire job interview up to this point has been about you, this portion is actually about the employer. Many people make the mistake of saying “This job would be a great opportunity to grow in my career and provide me with leadership opportunities and skill development.” Does that sound like a great answer? Sure. Is it what the employer wants to hear? No.

Employers do not want to hire people who solely want to advance their own careers. Employers want to hire people who are enthusiastic about the job and want to help the company grow with their skills and develop them further. So instead of saying that you want the job for your personal growth, talk about all the things you will bring to the role to benefit the company. Reply to this question by re-iterating your work experience and skills and how you are the perfect fit for this company. Elaborate by saying how your skills will make the company better. Of course, you should add in your passion and your interest in growing with the company, but answer this question in a way that makes it hard for them not to hire you.

For example, if you work in sales, talk about your previous sales success and how you know you can provide future sales for the company. Lastly, this is your opportunity to really show enthusiasm and passion in the position. Talk about how you love the company culture, mission statement (research it before the interview) and goals. This will also allow them to start imagining you in the role and make you a memorable candidate.


These are the hardest interview questions because most people answer them incorrectly. While they may sound like generic questions, what most candidates think is the right answer is usually not what the employer is looking for in a good answer. The employer is looking at not only your responsibility but how you choose to answer the interview questions and what points you are emphasizing. And while this sounds easy, I will be completely honest.

This post is a great place to start, but it will only get you so far in your career and interviews if you are only relying on finding the right answers and not the underlying components to a successful career such as confidence, mindset, and truly advocating for your value. If you’re ready to really take your career to the next level, past what’s on Google and Pinterest, I invite you to book a free Career Clarity Call to see if 1:1 Coaching is for you!





Leave a Reply

Your email address will not be published. Required fields are marked *