12 Tricky Interview Questions & How to Answer (2022)

We’ve all been there at some point in our careers. We are interviewing for our dream job. Then, the interviewer asks something we haven’t seen coming. We get stressed, don’t answer to the best of our ability, and may miss the role.
Well, it doesn’t have to be this way. Interview preparation can help you identify and cover all your blind spots, making tough interview questions a breeze. With this in mind, we’ve pulled together a list of the 7 trickiest questions along with advice on how to tackle them.

Related: 50 Most Common Interview Questions & How to Answer

1. Why were you fired?

Getting fired is way more common than we might think, and that can be a comfort. The most important thing to focus on is that for your own sanity. Realise that almost everybody has been fired at some point from a job. The interviewer has probably been down this road themselves.

This question might trigger an emotional reaction in you, even if you prepare for it, so it’s important to be careful, honest and brief. Position that situation as a positive learning experience and talk about how your expectations for the job were different than what the reality of the job was.

2. What’s your biggest weakness?

When you are interviewing, you are keen to speak about your strengths so that you get hired. So how do you answer a question targeting your weaknesses? Let’s see.

When an interviewer asks you about your weaknesses, they are looking to understand whether you lack any skills required for the job. Also, they want to see if you are honest.

With this in mind, we don’t suggest replying that you don’t have any weaknesses or that your only weakness is being a perfectionist. Come up with something real as long as it’s not very relevant to and important for the job. Here is an example someone could give for a back-office role:

“I am an introvert so I don’t thrive in roles that require client interaction. However, I’ve found that I can do a great job at jobs with fewer social elements. With this in mind, I’ve pursued a back-office career, which is aligned with my strengths”.

3. Why are you leaving your current role?

This is a dreaded question, regardless of the actual reason for leaving your job. If you are let go, it may feel awkward to talk about it. Even if you’ve chosen to leave, it can be hard to talk about the shortcomings of your current employer. Instead, focus on the role you’re interviewing for.

Start by letting them know that while you’ve learnt a lot in your current role, your growth has recently stalled. If you’ve been terminated, you can mention it briefly and move on. Then, explain that the role you’re interviewing for would be an excellent next step based on where you stand.

This way, you turn a tough question about your current job into an opportunity to demonstrate commitment and motivation for the new one. Here’s an example if you are looking to move from a digital marketing advisor to a digital marketing manager.

“I’ve thoroughly enjoyed my time with company ABC. I’m lucky to have a great manager, a nice team, and an interesting role that has taught me a lot about digital marketing. However, I feel like it’s time to move to the next level and there are no relevant opportunities internally based on the current business need. With this in mind, I applied for this role, which would allow me to apply everything I’ve learnt and grow further.”

4. Why do you have an employment gap?

Employment gaps used to be seen as red flags by some employers. However, things have changed. Hundreds of millions of workers were made redundant as a result of the pandemic globally, as many businesses had to downsize. Also, more and more professionals choose to take a career break at some point to focus on care, self-care, or volunteering. With this in mind, employment gaps have been normalised.

On this note, regardless of the role you’re applying for, I suggest being open about your employment gap. If you had to care for a loved one full time, share a brief story of the event. If you decided to take time off for yourself to focus on a personal project, let them know. You may even be able to relate this to the role you’re interviewing for and the skills it requires. Here’s an example.

“After working hard throughout my 20s and reaching the Director level, I decided to take a break to travel the world, which has always been a passion of mine. I visited 20 countries on 5 different continents and had the opportunity to grow by understanding different cultures. This experience made me more tolerant, understanding, and open-minded. Also, I set up a charity to help fight poverty in the Philippines, which I am still running. After a year off full-time paid work, I am ready and excited to hit the ground running and this role seems to be the perfect opportunity.”

5. Why did you choose your profession?

Questions like this one aim to prompt you to show your passion and drive for your career — a time to give a full background of why you love what you do.

This is the time where you can tell your story. Interviewers love this. It gives them a peek into who you are, what kind of person you are, what kind of communicator you are, what sort of drive and motivation you have.

6. Where do you see yourself in 5/10 years?

Questions about the future can be challenging. How can someone expect you to know where you’ll be after 10 years? The reality is, they don’t.

The reason that employers ask this question is to understand whether you have a career plan and if you’re committed to a career related to a role. With this in mind, let’s look at an example. Assuming you are applying for a business transformation consultant role with a consulting firm, you could reply this way.

“I love helping businesses get better through technology. In the short term, my dream job would be working with you as a consultant. Then, after 10 years I imagine I will have built the skills to take a leadership role and make a bigger impact on the industry.”

Related: How to Answer the Interview Question 'Where Do You See Yourself in Five Years' Like a Pro

7. Tell me about a time you failed at work.

Talking about wins is easy. However, we all find it hard to talk about failures. If you are wondering how you can speak to a prospective employer about times when things went wrong, keep reading.

First things first, your interviewer is looking to understand whether you’ve failed in any important and relevant projects. Also, they want to see whether you have any related weaknesses. Most importantly, they are seeking to understand how you treat failure.

With this in mind, I suggest answering by bringing up an example that is irrelevant to the role you’re interviewing for. A story where you weren’t fully responsible for the failure could work even better. Also, focus on how you use failure as an opportunity to learn and get better. Here’s an example:

“When I was working as a project manager for company X, we failed to deliver a project in time, as the business had to cut our budget due to an internal crisis. I had invested a lot of effort into the project, so when this happened, I got disappointed. However, I kept doing my best and we managed to go live sooner than expected given the new circumstances.

The senior management commended me for my perseverance and performance. This experience taught me that we don’t always have total control over large projects and that it’s important to keep going even when things get tough.”

8. What did you dislike about your previous job?

It is common knowledge that badmouthing a previous job, manager or employer should be avoided. On this basis, answering a question about something you didn’t like in relation to your past experience can be tricky. However, have no fear, as there is an easy way out of this question.

Start by considering the differences between your previous role and the one you’re applying for. Then, explain that the elements of the job that you didn’t enjoy as much are aligned with these differences. Let’s assume that you are an HR generalist applying for an HR technology position. Your answer could be the following.

“I love HR work and my previous role as a HR generalist was an excellent opportunity to gain broad experience in the function. However, due to the wide range of responsibilities that I had, it was hard to deep-dive into my favourite aspect of the job, technology. Now, I am focusing on HR tech roles, where I’d have the opportunity to use my broad HR exposure to design, implement, and manage relevant HR solutions while learning more about technology.”

Related: 11 Things to Never Say in an Interview

9. Tell me about the worst manager you ever had.

This question is not about throwing your old manager under the bus, but rather reflecting on what you learned from working with them. The phrase “my worst boss taught me…” is a good way to frame a difficult experience you had with a manager. It’s all about taking the high road and being gracious in many ways.

10. What attributes do you have that will support you in this role?

Answer this question in the context of why you have enthusiasm for your broader career. In talking about what about the job excites you, explain how you’ve specifically worked towards being good at it. If there’s a profession you really love, you can just really fire up and say … that’s why I developed x, y, and z skills. That gives you the chance to zoom, to show your excitement, energy and passion.

11. What are you most proud of in your career?

This can be a tough question, especially if you have a long career. However, focusing on relevant achievements can make things simpler. Here’s what I mean.

Let’s say that you have experience in Marketing and Finance. In your most recent roles you were a Marketing Manager, and now you are applying for Marketing Director opportunities. In this case, the best answer would focus on your most impactful, recent, and senior marketing achievements. Bonus points if you can relate your answer to the responsibilities of the role you’re interviewing for or the culture of the prospective employer. Here’s an example.

“In my last role, I was responsible for the business transformation of our marketing department. It was a tough project as we used to have obsolete systems and inefficient processes. However, we managed to streamline our processes and implement cutting-edge technology within the planned budget and timelines. I know you’re about to embark on a similar transformation and I’d love to help you.”

12. Do you have any questions for me?

You can turn the tables at the end of the interview and ask your interviewer tricky questions too. It is through these questions that you can figure out whether or not the company is a good fit for you. In addition, the questions you ask can be a means to show that you have thoughtfully researched the company.

Don't ask questions that you can find the answers to on their website, but questions that show a deeper level of thinking, like "What is your long-term vision for the company," "what are the biggest challenges your team is facing" or "what does it take to be successful here?"

Related: Questions You Should Absolutely Ask An Interviewer