10 Tricky Interview Questions and How to Answer Them

Interviews can be like learning a new language, you prepare what you want to say, say it well and then comes the difficult bit – someone questions what you have just said – and they speak fast, and you are not too sure how to answer.

You will have prepared well for your interview.  You will have researched the company, the role, what you would bring to the role and you have some positive examples to demonstrate your skills, show how you manage conflict and how you motivate yourself and others.

And then the interviewer asks the difficult questions.

Why did you leave your last job? There may be very easy explanations, for example relocation, the end of a fixed-term contract or redundancy.  But your situation may be more complex, a difficult boss, an unmanageable workload (often a result of the first), there might have been bullying or harassment issues.  As far as possible, always be positive about leaving your role.  Do not be negative about the company or individuals within it.  Say you are looking to advance your career in the way that the new role would offer; that you have been able to give yourself a few months without work to concentrate fully on finding your next role with an organisation where you will be able to grow and add value.

Why is there a gap in your CV? Do not feel embarrassed about this.  This is a planned career break.  If you have been able to follow any courses or undertake any voluntary work during this time, you can point to this. If you were bringing up your family – explain this.

What do you see as your greatest weakness?  When and if this is asked, it is an exercise in demonstrating awareness of where you could become stronger professionally. Do not use it to admit to terrible time-keeping or being a perfectionist.   If possible, show how you are already addressing your acknowledged weakness. For example:  say you are conscious of not always participating fully in meetings, but have set yourself the task of contributing one comment, idea or question when appropriate.  Or, your digital skills need updating and you have signed up for an online course.

Tell me about your worst boss.  You have had no ‘bad’ bosses.  For some in their early management career, you find communicating has been difficult, or work allocation has been unequal.  If you do want to bring in examples of bad management, to demonstrate that you recognise it when you see it, never identify the person or the organisation.

When Did you Fail? As with questions around weakness, it is important to highlight the learning from the failure and what steps you took to lessen the effects of what went wrong.  Did you miscalculate resources necessary for a project?  With any failure, talk about at what stage you realised things were going wrong, and most importantly at what stage did you ask for help and / or put things right.  This will demonstrate awareness and honesty.

Why You? This is similar to Why should we hire you ahead of the other candidates? Or What value can you add?  Prepare for this question by looking again at the Job Specification and your CV or Application Form.  Talk about the experience and skills you have that are relevant to the role.  Give an example, tying together your experience and their needs.  If the organisation talks about launching new services, talk about a time when you have contributed to expansion and that you worked successfully under pressure in these situations.  Always relate your experience and achievements to the role in question.

How do you cope with or manage Conflict?  It is best to have a clear example here and illustrate an appropriate response.  Are you the unofficial, but very important, peacemaker in the team, gently sorting the issues that arise in any group?  Or have you had to deal with significant conflict directly, ensuring processes were followed correctly and a duty of care was and could be shown.

Tell me about yourself. Broad questions such as this have their own complexity.  There is a temptation to answer too broadly, or start too early.  Try and stay focused on work examples with one or two added extras; add a bit of you to the answer so the interviewer feels they know you better than when you walked in (– but they don’t need to know your memories of primary school!)

What was your worst job? Try to keep this to something very early in your career, and again be discrete about the employer.  You can give an example of when you felt your career was blocked – but don’t give an impression of impatience or entitlement to promotion.  Or there might have been a time when you were considered the go-to person for unpleasant or even dangerous tasks.

Give us your Elevator Pitch.  In other words, tell us in 60 seconds or less why we should hire you.  Preparing for this is positive in many ways.  It will help you speak with clarity, and help you focus your own mind on why you want to work for this company, in this role; and how you, your skills and your experience can add value to their organisation.

Remember, the interviewer is not trying to make you feel uncomfortable by asking tricky questions.  They recognise that no one is perfect, but they also need to ensure that the person hired will work successfully in the role, contribute to the team and add value to the organisation going forward. Your preparation and honesty will help them make that decision.


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