How to answer these 10 tricky interview questions

man sitting right hand side waiting for appointment beside 3 empty chairs

You thought you’d prepared well – done your research, read the right papers, rehearsed your response to the classic questions. But here comes that curve ball and your head is suddenly empty, now the hesitant ‘er’ kicks in – and you’re gone.

It’s not personal, of course. Interviewers aren’t trying to catch you out just for fun. It just feels like that. What they’re doing is looking for ways to distinguish between potential employees.

There are lots of great CVs out there, lots of candidates full of personality and initiative. The tricky question shows your potential new bosses are looking for something else: the candidate who can think on their feet, someone adaptable and very often it’s the kind of question that’s designed to make you show genuine insight, honesty and personality.

To be honest, you’d have to be deeply unlucky to land an unanswerable question. Even if the interviewing team have spent long hours developing their “something a little bit different”, a bit of logic and a lot of preparation can get you out of most deep holes.

The trick is not just knowing the questions, but knowing what the interviewer will take from your answer. So here’s how to counter some of the tougher lines that can come up.

1. Why should I hire you?
The question which most frequently floors applicants. You need to have done your homework on the position you’re going for, because your interviewer needs to know you’re the person best qualified for that role. Take time beforehand to identify the skills and knowledge needed for the job and identify your past experiences which illustrate that you have those skills and experiences.
2. What’s this gap in your work history?
Don’t fudge this. Employers understand that people lose their job. Emphasise the positives in what you were doing during that period: volunteering, retraining, undertaking freelance projects – activities like these show that you’ve been productive and proactive.
3. Which one thing would you change about your last job?
Careful – this one’s easy to trip over. Don’t give out too much information, or launch into a rant about former colleagues or bosses or even work environment practices and structures. You don’t want to be seen as critical, but nor do you want to be seen as someone who doesn’t vocalise issues. Give an answer that emphasises the positives you’re looking for, things that will make you more productive or happier in your role. Talk about what you’re looking for (which coincidentally can all be found in the position you’re interviewing for) and not what you might want to flee from. Inefficient or outdated technology is a good place to focus your answers.
4. Tell me about yourself
Keep it short, don’t launch into a rambling life history. Your success as a child star or your gap year trip are unlikely to reveal much about your suitability for the job you’re applying for. This is all about the qualities you’ve displayed over the years, so focus on education, work history and recent career experience – especially the latter. If you mention an event make sure it reveals something relevant for the role, be ready for follow-up questions so don’t unload every single point. Above all, remember one word: brevity.
5. Explain ‘this aspect of what we do’ to your 8-year-old nephew
This one is all about discovering whether you have a clear and precise understanding of what your employer does. Being able to distil a company’s service offering, proposition or core business into one powerful, simple statement shows clarity of thinking. So research, research, research. Whether it’s developing cancer drugs, arranging funds, designing truck suspension or unravelling a complicated database, if that’s the company’s stock-in-trade you need a solid understanding of it.
6. What would the person who likes you least say about you?
Doesn’t sound too promising, but this can be turned to your advantage if you balance a potentially negative quality with a positive. Characteristics like impatience – which can be difficult in a workplace – can illustrate your determination to get things done in the face of a deadline. Some people might say they dread getting a follow-up call from you, because you’re thorough and think everything through. This is an opportunity to show reliability and leadership.
7. Tell me about an incident when old solutions didn’t work
You see – you’re spotting these tricky ones a mile off now. This question is all about discovering how knowledgeable you are in the modern workplace and how you would embrace new ideas to solve problems. Technology is an obvious crutch here – whether in purely practical terms or in harness with lateral thinking to, say, employ social media strategies. Take the opportunity to show yourself as a leader, a problem solver and a team player.
8. What’s the biggest risk you’ve ever taken?
Far from being seen as a negative, or unsafe character trait, your willingness to take risks can be viewed in a positive light. The willingness to face potential disaster, to step outside your comfort zone and to take on something new all show character. Taking a risk, a calculated gamble, far from being foolhardy can display bravery and great self-confidence. Don’t be afraid of saying if the gamble didn’t pay off either, as being able to rebound from personal failure is an impressive quality too.
9. Tell me about when your decisions ever been challenged by manager or a colleague and overturned.
Here, the interviewer is looking for humility, a preparedness to accept criticism but most importantly, signs that you are able to learn from mistakes. This is not an excuse to deliver a shaggy dog story – just give brief details but stress how the resolution helped you do your job better.
10. Describe a time when your team was in disagreement
Employers look to identify how you might react in the future by unpicking past incidents. Explain the situation briefly, describe the actions you took to bring the group back to agreement or to resolve the situation and what the results of the action were. Stress what you learned.

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