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Imagine you’ve just landed an interview for a dream job. You probably feel as though you’re at the peak of a roller coaster, peering over the edge. The hard work of finding openings and chugging through applications is done. But before you know it, the car is going to lurch forward and take you with it. It is time to get prepared for what could be the most important interview of your life.

Interviews, just like roller coasters, bundle up excitement with fear. They can be both invigorating and terrifying in equal measure. The key to enjoying them is being confident and prepared — and what better place to start than with these ten tricky interview questions.

Read on to learn how to nail your responses, and get your interview prep off to a flying start.

1. Can you tell me about yourself?

This perfectly innocuous opening question, answered well, can set you up for a very successful interview. Ace it and you not only build rapport with the interviewer, but give an insight into your personality and how you might fit the company culture. This question also allows you to give a quick rundown of your skills as they apply to the position. Use it well.

The reason this straightforward questions sits in the ‘tricky’ bucket is because it can be answered in so many ways. You could launch into a life history. You could describe what you had for breakfast. Or you could rattle off a bullet point list of career highlights without stopping for breath. None of these work well.

What an interviewer is looking for is a balance of personality and professional experience, presented with confidence and self-awareness. By all means, give a brief insight into your personal life, your interests, and passions (especially as they apply to the role at hand), but try to find ways to link quickly back to your professional interest, rather than getting caught down a rabbit hole of autobiography.

So, for example, you might start by talking about your childhood love of horses, or your volunteer work in an animal shelter — but loop ‘round quickly to how that passion for nurturing others and being outdoors applies to the job you’re desiring as a summer school group leader.

2. What will you bring to this role?

This question is where you get to explicitly match your personal skills and experience with the requirements of the position. From your research, you should be crystal clear about the skills requirements of the job, and the type of company culture you’re heading into. Make the decision easy for the interviewer by showing explicitly why you fit.

How do you know you will indeed be a great fit? Start off with the job description itself, picking out the qualifications and experience listed as essential or desirable (which, if you’re applying for the job, should match your skillset fairly well). Then scan the company’s website or talk to connections you have in the business to get a feel for the sort of team culture you might expect.

If you like to prepare by writing down model answers, then try pulling examples from your career history to illustrate each of the skills and experiences that are listed. While you are doing so, think about both the ‘what’ and the ‘how’. ‘What’ you did in each example is crucial to show your skills, but ‘how’ you did it will determine your fit in the company culture. Consider how best to describe your approach to each problem, as well as describing what actions you took.

3. Why do you want to work here?

While it might not always feel so, interviewers are human, too. They want to work with someone who wants to work with them. Hearing about why their company is great is flattering and validates their own choices. So, make sure you’re very clear on what attracts you to their business, and you’ll strike a chord quickly.

The key to answering this question is research. You need to show that you have learned about the business and industry, and that you have an informed opinion about the challenges and opportunities facing the company. To research, you can first exhaust the ‘official’ channels, like the company website, social media feeds, and press releases. But to get a real depth of insight, try some broader research too.

Related: 6 Ways to Leverage Social Media in Your Job Search

Follow the company leaders on Twitter, to see what they’re talking about. Check out the competitors websites and how they’re being covered in the press. Find industry magazines and blogs, which can give an unbiased view of what’s news in the segment. Try to have a personal view on what the main strength of the company might be (and why that appeals to you), but also what challenges and opportunities might be over the horizon — and how you can use your skills to help address them.

4. Do you prefer to work independently or in a team?

For most people applying for the majority of jobs, the actual answer to this question is, ‘Yes’. If that caught you off-guard, it’s a good thing you’ll be thinking about your answer to this tricky question now.

There are very few roles which value either independent or team work exclusively. Most jobs in the real world require you to flex both of these skills, and be able to drive your own agenda alongside working well with others. Interviewers know this, and would like to see your ‘gut’ answer to gauge which is your natural preference.

It’s important here to think about your authentic view. Most people are more naturally inclined to prefer one work style over another. They should also understand, though, that working alone on certain types of project gets better results, while teamwork is essential for others.

Showing you are flexible is most important. For example, you might explain that you are naturally more driven to complete tasks alone, but value the experience of working in a team on projects that require creativity or have multiple ‘moving parts’. This shows that you know how to flex your style but also have some self-awareness about your personal strengths.

5. Where do you see yourself in five years’ time?

Answering this questions comes more naturally to some of us than to others. It can be very difficult to see yourself five years hence — particularly if you are changing careers or just starting out. But for others, articulating a career plan might be more straightforward.

If you have an idea in mind for the types of roles you would like to progress into over the next five years (and they fit well in the company you’re applying to), then go ahead and describe them. Think about how you come across. You want to be seen as looking to develop and grow along with the business, rather than looking to speed through, extracting value, and hightailing it.

If you genuinely don’t know where you might be in five years, that is okay. Don’t be tempted to say you want to land this job and then stay there indefinitely. Businesses want people who can spread their wings, even if that doesn’t involve progressing through the ranks. Instead, talk about the experiences you might like to gain from your work. Would you like to try working in different teams, learning from great bosses and mentors, or getting the opportunity to work cross-culturally? Say so.

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6. What are you most proud of in your career so far?

When you are talking about your proudest moments and your great career achievements so far, you need to think carefully about the examples you select.

Needless to say, they should have some relevance to the role you are applying for. But that can be stretched fairly far, and you can draw links between different types of work experiences. Whichever example you choose, think about how you can explain it in a way that is easy for the interviewer to appreciate the scope of your achievement.

So, if you won an award at work, think about how they see the significance of that. Were you voted the winner out of a dozen different nominees? Or did you receive 90% of the votes for your category? If you won a tricky contract, what was the value? What increase in profile or productivity did you drive as a result of it? Finding a metric that shows why you’re proud of it gives an ‘anchor’ for the recruiter to relate to your choice.

7. What is your biggest weakness?

Yep, everyone’s nightmare question. But you know it is coming, so it’s best to have an answer prepared!

Giving a see-through positive trait twisted into a weakness won’t fly here. Don’t be tempted to say, ‘My biggest problem is that I just work too hard!’ Even with award-winning acting skills, the interviewer knows precisely what you’re doing.

A better approach is to select something you have genuinely identified as a development area. Explain how you have worked on it so far and what your plan is to continue to develop that skill.  This shows your self-awareness and your drive to develop personally — both traits that any employer will value.

So, you might explain that in your first few jobs out of school, you received feedback that you occasionally struggled with influencing more senior members of your team. Go on to describe how you have worked to overcome that, and what the impact has been. Then, you could explain that you view influencing as a core skill we all need to develop all the time, so it remains on your personal development plan even now.

8. Have you ever disagreed with the way your company (or boss) were approaching a problem? What did you do?

Most of us have had cause to disagree with the business or boss we work for. The issue might be minor, but it is still something that causes conflict, and where we must decide how to match our principles with the demands of our work.

Whatever example you use here, make sure you frame it in a positive light. Describing previous businesses or managers in a very negative way makes you look petty and can cause a recruiter to worry about how you relate to others. Present the situation neutrally, without loading criticism on top. Then describe what action you took, and the result you achieved. The STAR method really helps when preparing for this type of example based question.

You are trying to show the way you influenced others and stuck to your principles, in however small a way. Don’t choose an example where you disagreed, but rolled over anyway. Even if you did not manage to change the outcome, you can ‘show your workings’ to demonstrate that you are comfortable presenting your opinion in conflicting situations.

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9. Describe the best boss you have ever worked for.

This question might also simply be asked, “How do you like to be managed?” Interviewers are looking for an insight into how you might fit into the particular team and company culture.

If you already know the manager of the position for which you’re vying, then you have a head start. Gather whatever intelligence you can on how they like to work, as it will help you understand the team you are looking to join.

If you don’t know much about the business, then be as honest as you can about how you like to be managed and how previous bosses have brought this out of you. Do you prefer to be left alone to work independently? Do you like to have a boss as a sounding board who you can always turn to for feedback? Do you tend to build strong bonds with managers and the team, and want to work in a group that reciprocates this?

Do not be tempted to give the answer you think the interviewer wants, but do find ways to show how your preferences might fit the company culture. So you might say, “I read that the culture here is to work in small project teams with remote management by a team leader. This is great because I like to work with a boss who trusts me to get my part done, and checks in on a structured basis as we progress.”

10. Have you got any questions for me?

Unlike most interview questions where there are a number of ‘right’ ways to respond, here the answer is always yes.

Do not ask banal questions about the dress code, availability of laptops, or other ‘housekeeping.’ There will be time for that later. Have a good think instead about the questions that are relevant to you.

Asking the interviewer about their own personal experience is a good way to get valuable insight and also show an interest in the day-to-day working of the company. You could ask about the key challenges the business faces, or the way they are reacting to changes in the marketplace — these questions show a good understanding of the segment and an analytical mind. If you are particularly ambitious, you could ask about the typical career progression in the organization… another way of demonstrating your intent to succeed. Or if you are really brave, you could say, “Do you have any concerns about my ability to succeed at this role? If so, I would love to understand them so I can fill in the gaps now.”

If you have an interview lined up, preparation can feel overwhelming. It is especially tough if you are doing so alongside holding down a full-time role. Start with the tricky questions that worry you most, and invest some time in writing down answers. Stick your written notes somewhere you will see them, like the car sun visor or the bathroom mirror, for effortless preparation and easy reiteration. Just talk your answers through in the shower,  in the car, or any time you have a spare moment, and you will feel confident in no time.

What are your tips for tricky interview questions? Let us know in the comments!


Author Bio

Total Articles: 15
I am a writer and coach, focusing on helping people achieve their goals in careers and financial wellness. With ten years experience working in HR and Leadership roles in some of the biggest corporates in the UK, I am a qualified coach and member of the UK Institute for HR Professionals (CIPD).

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