What would be the toughest question I could ask you?

  | James Innes

What would be the toughest question I could ask you?

Alternative and related questions:

What’s the toughest question you’ve ever been asked at interview?

The meaning behind the question:

This is a question which puts you firmly on the spot. Obviously, once the interviewer knows what the toughest question is they’re going to be expecting your answer. As well as seeing how you react to stress, they will be hoping to identify a chink in your armour – the main reason you’d feel a question to be tough is of course because it hits a raw nerve and exposes a weakness.

Your answer:

There’s no doubt about it – if you’re not prepared for this question then this question itself is probably one of the toughest you’re likely to ever get hit with. However, if you’re prepared then it’s a completely different kettle of fish.

It should go without saying that you should definitely not really tell them what the toughest question is. This is an opportunity to get the interviewer to ask you a question of your choice – one for which you know you can deliver a positive and impressive response.

You obviously need to suggest a question which can definitely be described as ‘tough’ – and, ideally, it should be a question an interviewer is unlikely to ask you. It makes sense to have three or four possibilities lined up just in case your ‘favourite’ has already cropped up earlier in the interview – and in case the interviewer follows up by asking you to pick another one! I’d suggest you simply pick out three or four of the tougher questions from the previous chapter.


I would say this question itself is probably one of the toughest you could ask me! Let me see… I suppose that, for me, a really tough question would be one which exposes a weakness, something along the lines of, “What’s the worst mistake you’ve made at work?”

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