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6 Difficult Interview Questions Which Trip Up Even Smart Applicants

Updated: Nov 4, 2022

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Do you freeze up when faced with an unexpected interview question? Even the most confident and qualified job candidates can fail to answer interview questions effectively. That’s because job interviews are difficult situations, and you never know exactly what will be thrown at you until you’re in the hot seat.

It’s not just the answers you give but also how you give them that can make or break your chances of being hired. For instance, appearing overly nervous or talking too much is indicative of a lack of preparation on your part, both of which aren’t exactly confidence-inspiring for your potential employer.

Going into every job interview, you need to expect a few tough questions. In this article, we'll answer 6 difficult interview questions which trip up even the smartest candidates, and how you can prepare for them them:

We'll also cover how to:

1. Tell me about yourself

This is a common interview question that allows you to set the tone for the rest of the interview. As such, it’s also one of the most difficult to navigate. Interviews often begin with some variation of this question. It might seem like a polite icebreaker, but don't be fooled - even when asked casually, this is when your interviewer will form that all-important first impression of you. So it's critical to get it right!

When answered well, this question provides an insight to your core skills, your personality and your ability to respond to an unstructured question. Many jobs need someone who can think on their feet or present ideas with crispness and clarity. Your response can demonstrate that you possess these skills. This is not the time to repeat information in your resume or cover letter - you don’t want to sound like you have memorised a script, as this will come across as inauthentic and won’t allow the interviewer to get a real sense of who you are as a person.

A good way to go about answering this question is to start with your elevator pitch and expand by discussing your career path so far. Use your past work experience to paint a picture of who you are and what you can bring to the table. By taking this approach, you’ll not only manage to succinctly answer the question at hand but also provide insight into your character and personality, making your answer more conversational and authentic.

People connect with stories, so take this approach to weave in some personality and make a memorable first impression. To make your answer more relevant, align your story with the company values and the requirements of the role.

Include keywords from the job description in your response to this question. For example, if the job description says they need a “motivated self-starter,” your response could include a story where you took initiative. Try including a sentence along the lines of ‘I pride myself on….’ or ‘it’s very important to me to….’ This gives insight to your core values and what they can expect working with you.

In summary:

  • Be conversational and allow your personality to shine through.

  • Start with your elevator pitch – the short intro you prepared at the beginning of your job search covering the who, what, and why of who you are and what you can offer a potential employer.

  • Expand by sharing the story of your career path to date.

  • Connect your story back to the requirements of the job and the company.

  • Include keywords from the job description, such as “organised”, “confident communicator” or “takes the initiative”.

2. Walk me through your resume

This question is a natural follow-up to “tell me about yourself” and lets you focus on the most important parts of your experience and education. Now is your chance to selectively highlight the most relevant points from your resume for the job. Use this time to show how your professional experience aligns with the requirements of this specific role.

The key to answering this question effectively is to let the interviewer guide you, as not all interviewers will be looking for the same information. For instance, if your interviewer is the recruitment officer, they likely want to focus on how your education and qualifications meet the requirements of the role. Whereas if your interviewer is the direct manager, they will be more interested in the type of work you’ve done and examples of the results you have delivered in the past.

You will also need to consider the detail size of the information that your interviewer is interested in. Some interviewers may be looking for all the finer points on your experience and processes, whereas others will just want a broad outline of your past achievements. For the former, you’ll want to use bullet points to highlight your experience and achievements. For the latter, you can go with a more conversational approach, using your resume as a guide.

For example: “My resume highlights my customer service experience, which has been my primary focus throughout my career. I’ve primarily worked in front desk reception and have experience dealing with a diverse range of clients. My outgoing personality and people skills allow me to solve problems and meet client's needs even in challenging situations. In this next chapter of my career, I am looking to expand my skills in this area by taking on more responsibilities communicating with key stakeholders to deliver results”

How you say something is as important as what you say. So when you're sharing your successes, speak like the best version of yourself and make sure that you're doing it in a way that allows the interviewer to connect to you. When speaking about your achievements, you can focus on the clear facts, your credentials, and other people’s praise so you don’t seem self-absorbed.

In summary:

  • Talk through your resume by selectively highlighting your qualifications and experiences most relevant to the new role.

  • Start with the three or four key points that help them understand why you're a fit for this job.

  • Consider the position title of your interviewer, and the level of detail they are interested in, when you respond to this question.

  • Use a short sentence to let them know what you are looking for in this next exciting chapter of your career.

  • Be concise, and invite follow-up questions at the end.

3. What are your biggest strengths and weaknesses?

This is one of the most common interview questions, and may be asked in the form of "what are your greatest weaknesses" . What this question is really trying to do is get you to talk about your experience, your ability to be self-aware, and the transferability of your skills.

The key to answering this question is knowing your top 3-5 strengths. This will help you clearly communicate the talents and abilities you have to offer a potential employer. To answer a question about your strengths, discuss your top skills as relevant to the job you’re interviewing for.

In areas where you need improvement, focus on what you’ve learned from the challenge and how you applied your self-awareness in future. It's good to be honest about things you aren't great at. When a question asks you to reflect on something negative about yourself, give a short example, and then focus the conversation on the positive by sharing what you’ve learned and how you’ve grown due to the experience.

A good way to go about answering these questions is to think about your past work experience and what skills you’ve developed as a result.

For example: “My strengths include my ability to work well under pressure and adapt to new situations quickly. A weakness that I'm aware of is I sometimes get so caught up in the moment that I volunteer to do too much. I know this can be a distraction in ways that puts me at risk of not getting work done properly or missing deadlines. To combat this, I put in place detailed lists in my calendar to stay organised and meet deadlines, which has been critical to my success. These skills have been developed through years of managing multiple accounts and juggling competing projects. ”

In summary:

  • Answer this question by displaying self-awareness, commitment to improvement and personal accountability.

  • Know your top strengths and how they will transfer to this new role.

  • It’s good to be honest about the skills and traits you're working on.

  • Give a short example, then share how you've grown and what you're doing to improve.

4. Why do you want this job?

This is one of the most common interview questions and is often asked in conjunction with “what do you know about our company?”

It helps the interviewer understand your motivations for applying for the position and if you've done your research.

A good way to approach this question is to offer insights either directly or by referencing the company’s mission, vision and values. This is your opportunity to show interest in the position, and show that the role and the industry are ones you're genuinely passionate about.

For example: “I’ve always been a big fan of your company’s work, particularly in helping patients who are battling a chronic condition. I’ve recently graduated with a degree in psychology, where I focused on the mental health of individuals. I’m very interested in applying what I’ve learned to help patients with their mental health issues.”

The best approach to a question like this is to highlight the aspects you’re most enthusiastic about. Use the research you’ve done about the company and offer very specific reasons for why you want the job, such as:

  • You want to work for a small not-for-profit because you want your work to be impactful and make a difference in the community.

  • You like the connection and support of a small office.

  • While you’re a self-starter and enjoy working independently, you thrive in a collaborative workplace. 

In summary:

  • Your response should be informed by your research on the company, the job and what you can determine about their work culture.

  • Focus your response on how you fit in, and the value and contributions you bring.

5. What are your salary expectations?

This is another common interview question, and one that can be tricky to navigate. A common mistake is to offer an overly high or low figure, either of which could be detrimental to your chances of being hired. A better approach is to offer a range for your salary expectations, which allows you to account for factors such as your experience, skills and the cost of living in your area.

When asking about salary, the interviewer is seeking to understand if your expectations are aligned, if you're within their budget and if they can afford you.

For example: “The salary range listed on the job description is $45,000 to $50,000. I’ve done some research, and that range aligns with my level of experience.”

In summary:

  • Know the industry average for similar jobs.

  • Speak in ranges rather than exact numbers.

  • Let them know there’s room to negotiate, and mention perks or packages.

  • Make the case that you offer premium value and bring up signing bonuses.

Doing this can create a win-win situation for both parties. Asking for extra money in the way of recurring bonuses can be a way to get you to the higher end of your salary range.

6. Do you have any questions for us?

Interviews often ask a version of this question at the end of the meeting. Preparing a few thoughtful questions ahead of time prevents a mike-drop moment and ensures you leave the interview on a strong note.

Many people prepare for all the tough interview questions about strengths and weaknesses and their past job experiences, but forget that they should also ask questions to get to know their potential employer!

Asking thoughtful questions is a great way to gain respect and demonstrate your knowledge of the company and their work. Don’t waste this valuable opportunity to ask about the company you could be working for and show that you’re invested in the opportunity.

To prepare your questions, think about what you prioritise in a workplace and note down any relevant questions. Consider:

  • How big is the team I will be joining? 

  • What goals have you set for the role previously?

  • How does the company support staff with learning and development opportunities?

Scan the company website or read their annual report. Do you have any questions about the company strategy or the challenges they currently face? Asking about the company's top products, services and other activities can help you to share more of your personality, interests and values.

Consider what the company culture is like. It’s not always easy to surmise that in a one-hour interview, but you can dig around for more information. Try asking pointed questions, such as:

  • When someone drops the ball on a project, how does your team handle that?

  • When there is a conflict, how does management resolve it?

  • How does the company ensure there is a sense of community even when people are working remotely?

Show them you’re paying attention by pulling a question from what was discussed during the interview. This lets them know you’ve been listening. You may want to loop back to something you'd like to discuss further like an aspect of the job, the team, or the challenges that lie ahead. If there's a question that you feel you could have responded to better during the interview, now is your opportunity to re-address it and fill in any gaps.

By asking carefully selected, relevant questions, you'll stand out from other applicants. This shows you’ve thought carefully about how you will fit into the company and role, as well as how you can contribute to their future success. 

It's OK to pause and gather your thoughts

If you're asked a surprising question during your interview, don't rush yourself into a response. It's OK to pause a moment to gather your thoughts, or to ask a clarifying question before you answer.

As much as you prepare, there may be moments during the interview where you feel at a loss. Take a deep breath, and if you're really stuck, say something like: “That’s a great question. I need to think about that. Can we circle back to it at the end?” as a way to buy time and confidently move to another question. 

The most important thing is to always be honest in your responses. If you are successful in achieving the role, you want things to start out on the best note possible without any inaccuracies that could come back to haunt you down the track!

Look out for red flags

Always remember they are not only interviewing you, but you are interviewing them. Your comfort and happiness in the job is just as important as their satisfaction with you as a member of the team! Don’t get so focused on nailing the interview that you lose sight of the fact that you need to be evaluating the company, too. Is this workplace and position right for you?

Consider whether your potential manager is someone you can imagine collaborating with. Pay attention to how you're treated throughout the interview process. Did you get a good feeling from the people interviewing you and the company as a whole? Are these people someone you can imagine going to with problems? Trust your instincts, you'll know what's right for you.


In this article we’ve covered 6 difficult questions commonly asked, in some form or another, during an interview.

More complex questions can come up, many of which can come from left field, so the more you research, practice and prepare, the better!

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We can help you prepare for all these questions, plus many more. Find out more and book your interview preparation session here:

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