How to answer 10 of the toughest job interview questions

Don't get flustered when your potential boss throws you a curveball.

by Jack Torrance
Last Updated: 13 Jul 2017

Few of us relish the prospect of a job interview. Getting dressed up in your Sunday best, stumbling through question after question, trying to simultaneously come across both as an effective operator and a nice person to work with - it’s not the ideal recipe for a relaxing afternoon.

It’s all the more difficult when the interviewer throws you a curveball. Earlier this year the job site Glassdoor, which allows users to rate employers and submit questions they have been asked in interviews, published its list of the toughest it had seen in the past 12 months. To put your mind at ease, MT asked a couple of careers experts for their take on how to answer 10 of the trickiest (you can see the full list here).

1. ‘What am I thinking right now?’ - (For a regional director role at TES Global) 

‘There are many ways to answer this question – lunch? Need the loo? How did I get lumbered with interviewing these numpties? and so on,’ says Graham Philpott, careers consultant at Henley Business School. ‘But perhaps what the interviewer is looking for is your understanding of his or her priorities.’
‘This will require you to have a good understanding of their role, and the strengths, weaknesses, opportunities & threats pertaining to it – so make sure that you do your research. Also, they are likely to be thinking about what the ideal recruit would be like, so be ready to talk about how you will add value to their team & therefore help them achieve their goals.’

2. ‘What on your CV is the closest thing to a lie?’ - (Marketing and communications employee, The Phoenix Partnership)
‘Marketing and communications are about sales, which emphasises the positives, and fails to mention the negatives,’ says Philpott. ‘CVs are marketing collateral, so this question is a way for interviewer to find out what spin you are putting on background. As the role will be in Marketing the question is testing 2 things – what lies beneath the gloss of your answer & how skilled you were in your marketing technique.’

3. ‘What is your coping mechanism when you have a bad day?’ - (Consultant, Switch Consulting)
‘It may be tempting to don the halo and put up the pretense that you are unaffected by stress, but everyone has their bad days. Employers are not looking for saints, they are keen to find out how you manage yourself when things aren’t quite going according to plan,’ says Tony Goodwin, group CEO & chairman of recruiter Andal International.

‘So think about the steps you take to improve your lot. Perhaps you find taking time away from the office and going for a short walk works best for you, in terms of re-energising for the rest of the day. Or maybe, if that isn’t practical, you go to the gym or for a walk with the dog when you get home. Whatever it is you do, share it – your actions may actually help some of your new colleagues.’

4. ‘If your best friend was here what advice would he give you?’ - (CCP, American Express)
‘"To go to interviews by myself in the future" springs to mind – but be careful using flippant humour in interviews, it rarely goes well,’ says Philpott. ‘The thought process behind this question is that your best friend has insights into the way you think, act & react, and that these insights will help the interviewer decide about you.

‘Perhaps a sensible way to approach it then is to use it as a way to describe what kind of coaching helps you perform well in stressful situations – a kick up the backside, an arm around the shoulder, visualisation of past success, a reminder of the goal etc. – what works for you?’

5. ‘Describe your biggest weakness. Then describe another.’ - (Forward deployed software engineer, Palantir Technologies)

‘This is all about getting candidates to be honest about those areas of their work which could be improved,but more important is how they are already doing it or plan to do so - take myself as a case in point,’ says Goodwin.

‘I am acutely aware that attention to detail is perhaps not my greatest attribute. To remedy this, I ensure that I have someone on my team who has the detail-orientated approach that is needed to ensure we work effectively as a collective.

‘That’s what managers like me and others are looking for – people with a degree of self-awareness that enables them to not only recognise where their own strengths lie, but also the way in which the strengths of others can complement their own weaknesses.’

6. ‘How would you describe cloud computing to a 7 year old?’ - (Graduate scheme, Microsoft)
‘Candidates specialising in new technologies need to be mindful that while they may have an intricate understanding of their subject, the same does not necessarily apply to everyone else in the business,’ says Goodwin.

‘Employers want people who can translate what can often be complex information into a format that can be easily understood by everyone else in the business.’

7. ‘What’s your the biggest regret managing people so far?’ - (Area director, Regus)
‘This is a great opportunity for the candidate to share examples of challenging instances during their managerial career, and the lessons they have learnt along the way,’ says Goodwin.

‘Some candidates respond to this question in an overly positive way by refraining from making any negative references to life as a manager for fear of diminishing their chances of interview success. But that is not the case.

‘Employers are looking for honesty and while they may be searching for the perfect candidate, they’re not looking for the perfect person. They know that the role of a manager has its challenges and they are looking for candidates who don’t try to pretend that managing teams is always a walk in the park.’

8. ‘What would you ask the CEO if you met him one day?’ - (Performance analyst, British Airways)
‘This is a way to find out what research you have done, and what conclusions you’ve come regarding what are, or should be, the CEO’s priorities,’ says Philpott. ‘It’s also testing how you would phrase a question to a really senior person: are you capable of communicating to the C-suite. The question you choose also communicates something about you – e.g. is it critiquing a current failing, reviewing a historical act or looking forward to what is coming next.’

9. ‘Provide an estimate for the number of goals in the premier league.’ - (Management accountant, VAX) 
‘The question is looking for an estimation – therefore it is checking your ability to guess well,’ says Philpott. ‘The job isn’t with the FA, so knowledge of the subject matter isn’t important – so be open about how much you know about the subject as part of your response.

‘You’ll need to agree some assumptions/clarify some ambiguities first e.g. are we talking football (soccer)?; in the UK?; this season so far? Then talk your way through each step of your thought process, making/agreeing further assumptions as you go. Often with this type of question the interviewer doesn’t know the answer – it’s the reasonableness of the estimate & the repeatability of the process that matters.’

10. Tell me about your childhood  (Learning and development employee, Next)
‘We are all products of our environment, and we all bring those approaches and attitudes into workm’ says Philpott. ‘You are in control of the answer, so tell them what you are comfortable with, in the way you are comfortable doing.

‘If we step back & consider why, other than nosiness, the question is being asked, then one reason could be empathising with the clients, in this case the retail, warehousing & office-based staff of Next, so does your background help or hinder your ability to empathise? Do you know enough about the demographics of your client group to enable you to answer this? If not, find out before the interview.’

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