How To Answer The Most Challenging Job Interview Questions

best way to prepare for challenging job interview questions

Job interviews can be stressful. A lot is riding on the outcome of this one meeting where a stranger has decision-making powers over your career and income. They also compare you to other candidates in your field to see how you stack up. 

With that much pressure placed on a single conversation, it’s no wonder that most people find interviews to be nerve-wracking. This is only compounded by the fact that your poise, confidence, and communications abilities are among the things you are being evaluated on in a job interview. These are all traits that are harder to convey when feeling anxious. 

There are ways to mitigate this, but preparing is the best way to succeed in a job interview. Research the company, prepare your answers to the most common job interview questions and practice responding confidently to the most challenging questions. 

This way, when the big day arrives, you can focus on what to wear and how to get there on time, because you will already know what you plan to communicate to the employer. Preparing for a job interview makes it much easier to make a confident, professional impression, even when feeling nervous.  

Here are some of the job interview questions you will almost certainly be asked, the questions that job seekers struggle with the most, and the questions you should be asking the interviewer. 

  1. The most common job interview questions
  2. The most dreaded job interview questions
  3. The STAR method for answering interview questions
  4. The last question you will be asked in most interviews


The most common job interview questions 

No two job interviews will be identical. Individual employers will have their conversation styles, interests, and preferred questions. Interviewers will also ask job-specific questions to establish your familiarity with the demands of the role.

how to answer the most common job interview questions

Nevertheless, there are recurring questions about your career goals, work style, and behaviours that you are likely to be asked in just about every interview you go to. Here are some of the most common – along with how to answer them. 


1. Tell me about yourself..?

The wording may vary, but at some point early in the job interview, the employer will likely offer you the chance to introduce yourself. They’ll say something to the effect of, “So, can you tell me a little about yourself?”

Do not respond to this by introducing yourself. This is a job interview, so you want to highlight your candidacy for the role. Make your elevator pitch. The employer isn’t interested at this point in your favourite books or hobbies; they want to know why you would be an excellent fit for the position they are trying to fill.

Your answer should describe how your credentials and career progression have led you to this point, where you would excel at this job and being hired for it fits perfectly with your career ambitions. The job must seem to align with your goals because this signals to the employer that you will be motivated to perform well in the role and stay in the position long enough to make some significant accomplishments. This is where your goals and the company’s align.

Here is a sample answer to the ‘tell me about yourself’ job interview question.


2. Why did you leave / Are you leaving your previous job?

Honesty is the best policy, right? Not always. While you shouldn’t lie about your skills or experiences to get hired for a job, you should not always tell the unvarnished truth in job interviews either. It’s fair game. Employers aren’t always strictly honest with you either.

The fact is that most people leave their jobs because of their relationship with their manager. Other common reasons for leaving a job include boredom with work, not getting along with coworkers, or lack of progression.

None of these make for good job interview answers, however. You don’t want to say anything critical about your past work experiences, or you will only come across as negative. Tell the employer that you are making a career move because you are excited about this opportunity. It is such an excellent fit for your abilities and ambitions that you just had to try to make the move.


3. Why do you want to work here?

Of course, you want to work there for the paycheque and benefits, but that is not what you say in a job interview. This question is your chance to show the employer that you have done your research. Talk about how your abilities can be assets to the team. Tell them how you like the company’s mission, culture, products and services. Demonstrating knowledge of the company and the industry works in your favour. Employers prefer candidates who know about their organization and are motivated to work for them specifically.

how to answer the question why do you want ti work here?

4. Where do you see yourself in five years?

This question is about your motivation. If you say that you plan to live off the royalties from the novel you plan to publish, it shows that your passions lie outside the accounting job you are applying for. However, if your long-term goals are to be a Director of Finance eventually, you will likely work very hard in the accounting role to rise through the ranks.

Explain how the job you are interviewing for fits your career ambitions. If it seems like a good career move for you, then succeeding at it will benefit you and the company. You will be motivated. Employers don’t want to spend time hiring and training someone for a job not connected to their goals, as they are likely to leave it as soon as something more relevant becomes available. That’s what the five years question is about.


5. What are your salary expectations?

A lot of people are uncomfortable talking about money. A recent scientific study found that being asked about salary was the second most stressful job interview question, based on measuring candidates’ heart rates. The only thing that topped it for causing anxiety was being asked to take an on-the-spot test of their skills.

In a job interview, you have to talk about salary. You shouldn’t bring up the topic of wages first, but when the employer asks you how much you expect to earn, you need to answer. Be flexible. State a salary range that does not go lower than you would actually be happy accepting and does not go astronomically high for a job at this level.

You could say, “The industry standards for someone in this position are between $70,000 – $90,000, and I would expect something in this range.” You can also suggest that this can be negotiable based on the overall compensation package and the details of the role itself.

Here are several more ways to handle the salary expectations interview question.


6. How did you hear about this position?

Employers like this question for several reasons. In fact, a recent survey of hiring professionals found that it ranked among their top five favourite questions to ask. 

This question often catches candidates off guard because they aren’t expecting it. What does how they learned about an opportunity have to do with their capacity for performing the job?

One of the reasons employers want to know how you heard about the role isn’t about your getting the job at all. They want to know how their work is performing. Companies spend a great deal of time and resources to attract talent to their open positions. So, they want to know which strategies are the most effective. How did they reach you? How did you find out about the opportunity?

The other reason they ask this question is that it can impact your candidacy. For example, if you heard about the job from a current or former employee of the company, this could mean that you come with a referral from someone who is known to the employer. That is a plus for getting hired. If you found the job on the company’s website, this implies that you are interested in the organization and were looking for opportunities there specifically.  If you found it on a job board, you are a motivated job seeker actively looking for new opportunities. 


The most dreaded job interview questions 

A recent survey has revealed the questions that candidates fear being asked the most. For this research, roughly 6,000 jobseekers were polled about what they dreaded being asked in job interviews. The top three most feared queries included the conversational opener, “Tell me about yourself.” This is unfortunate because, as I mentioned earlier, a version of this question will likely come up in just about every job interview. So, prepare your elevator pitch.

how to answer the most dreaded job interview questions

The other two most questions candidates most feared interview questions are: “Why should we hire you,” and “What are your weaknesses.” Here’s how to answer them. 


1. Why should I hire you?

This question is probably on the ‘most dreaded’ list because it sounds hostile, akin to being asked, “Just who do you think you are?” But it is not actually hostile. It is an opportunity. You obviously think the employer should hire you. That is why you applied and showed up for the interview in the first place. Tell them why.

Have three or four sentences in mind that sum up your greatest accomplishments and credentials in a way that makes you stand out as a great candidate for this particular job. Explain how hiring you would make the team, the department, or the company more successful. They should hire you because of what you bring to the table. Be confident, but not arrogant.


2. What is your greatest weakness?

This is a classic job interview question; employers don’t expect you to answer it honestly. Remember what I said earlier about honesty at the job interview? Don’t talk to the employer about your actual professional shortcomings; that is not what this question is about.

The weakness question is more of a test of your communication style. Naturally, discussing your failings in a job interview is uncomfortable when you want to impress an employer, so how do you handle it? Can you remain upbeat and conversational while talking about an awkward topic? How are you when you are on the spot, under pressure? Finding that out is why employers ask this question.

Talk about a skill set that is not vital for the job you are applying for, explain how you’ve struggled with it in the past, and detail the steps you’re taking to overcome the weakness. This shows that you are self-aware and motivated to improve.

It’s best to prepare for this one in advance because it is so common and can be tricky. Employers say that some of the worst job interview answers they have ever heard have been in response to the ‘greatest weakness’ question. Here are a few more strategies for answering it the right way


The STAR method for answering interview questions

The most revealing job interview questions employers will ask you are usually about your past work experience and on-the-job challenges. They want to know what you have achieved and what you have overcome. Some candidates struggle to tell these stories about themselves and their work, but fortunately, there is an easy-to-remember formula for crafting professional answers to these behavioural questions.

Keep the word ‘star’ in mind, and then talk about your past work by explaining the Situation, describing what your Task was, telling them the Actions you took, and what the Results were.

using the STAR method to answer job interview questions

Here is an example of a STAR answer to a behavioural job interview question.

Remember to customize your job interview answers to the specific needs of the employer and the job you are applying for. Spending a great deal of time talking about experiences or accomplishments that are not related to the role you are trying to land won’t help you get hired.


The last question you will be asked in most interviews

Somewhere towards the end of most job interviews, the potential employer will have finished up with their list of questions, and they will ask if you have any questions for them. Don’t say, ‘no.’ Saying that you have no questions can be a red flag that you are disinterested in the job or are just not a very savvy professional.

Ask questions. You and the potential employer both want to learn about each other. Asking smart questions is your opportunity to steer the conversation and make a lasting impression. The right questions can demonstrate that you are a motivated candidate who is passionate about the opportunity, has researched the company, and is eager to learn more.   

Ask about the company’s culture, the challenges of the role you are applying for, how they will measure success in the position, and what the next steps in the hiring process are.  Here are a few examples from hiring managers of the best questions they have been asked in job interviews.

On the flip side, don’t ask about salary, vacation time, or anything you could have easily learned from perusing the company website. Also, be especially careful to avoid these five sentences that will get you rejected in every job interview. 


Remember that an interview is not an interrogation

A job interview is a conversation, a professional dialogue. You are here because you need a job, and the employer needs someone to do a job. They are hoping that it is you. You are hoping to be hired.

So, the job interview is a discussion between two people who each have something that the other one needs, just trying to see if they would be a good fit working together. Prepare your answers to the most common and challenging questions, have your STAR stories ready, but also remember to be yourself. Being natural, friendly, and having a genuine conversation makes you likeable. Likeable people get hired faster.

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