How to ace the 6 trickiest job interview questions

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You're hoping to land that perfect new job and you've finally got your interview. Things are going well because you've prepped for all of the obvious questions related to the specific position and your experience.

But you might find yourself caught off guard by some employers' tricky questions, designed to learn more about your qualities and personality. We've rounded up 6 of the trickiest job interview questions, and given you some pro tips to help you prepare:

Q: Where do you see yourself in five years?

You needn’t have your career plan nailed down to give a competent answer to this job interview question. Your interviewer isn’t looking for specifics. They want to see if you’ve thought about where your future career will go, and whether you have ambition.

Whether it’s training more in the area you’re going into, or taking the next steps into a leadership role, some things will stand out to your interviewer. First, they want to know that what you want from the next steps in your career is something their company can give you. They’ll also want to see signs you’re going to be a loyal employee who doesn’t jump ship in a year.

Q: What did you most dislike about your last job?

You may have had a nightmare boss in your last role. Or perhaps you felt you weren’t given enough credit for your work. Whatever your experience, tread carefully. Interviews aren’t a place to settle old scores.

This job interview question is designed to find out whether you have tact, diplomacy and emotional intelligence.

No potential boss would expect you to have had just positive experiences in your career so far. So be honest but try to draw out positives that came from your challenges. And avoid badmouthing your previous boss, colleagues or company at all costs.

Q: Why should we employ you?

Here’s your chance to get the edge on other candidates. Pick out a few of the skills you have that the job description asks for. Then ideally back them up with an example of how you’ve demonstrated these at work.

You want to appear confident and show the value you can offer to a potential employer. But showing humility is key. If your potential boss thinks you come across as arrogant they might question whether you’ll get on with other members of the team.

Q: What are your weaknesses? Probably the trickiest of the job interview questions

In an interview you want to sell yourself as the best candidate. But along comes a question like this, asking you to talk about your negative points. It’s a tricky mix, isn’t it?

Just like with similar questions, the interviewer probably won’t be that interested in the finer details. They’re keener to find out how you deal with challenges and adversity at work. Ideally you want your answers to show that you have self-awareness. You will want to identify a problem area that you've made progress on that you can talk about.

Just make sure you don’t talk about a weakness in an area that’s crucial to the role!

Q: What are your hobbies?

This job interview question is designed to find if you have the type of personality and outlook that will fit with the company culture. If you don't think of yourself as having a hobby, consider what you like to do for leisure.

Your interviewer wants to see if you have an interest you feel passionately about, and care about anything outside of work that will make you a more well-rounded person. Any exercise hobbies are good to mention, as they show you prioritise looking after yourself and take steps to prevent stress. Team sports can be a way to highlight you’re a good team player.

Study the job description to find the character traits your potential boss wants to see. Then draw out the things that your hobby has developed or given you, especially if they align with those traits.

Q: What are you most proud of during lockdown?

For most of us, just getting by day-to-day during lockdown was something to be celebrated. And even if you don’t feel you achieved much, you may well have notched up some transferrable skills.

For example as a parent you may have juggled work with home-schooling and parenting. That makes your organisational skills (and collection of productivity hacks) second to none. Perhaps you helped out with a community Covid support group. No doubt coordinating with others will have helped you develop good teamwork skills. (Read more on why taking part in volunteering is a great interview talking point).

When discussing what you did during lockdown, just start from a point of honesty. Employers want real, authentic people to join their workforces, not necessarily superheroes.

Even though some of these interview questions might seem tricky, they’re not designed to trip you up. They're designed to reveal more of the real you to employers. So, try to see them as a chance to show your personality and how you can fit into an existing team.

Like these pro tips for tricky job interview questions?

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