The Bravest Interview Question You Could Ever Ask

bestinterview bestselfdoubt confidence interview interviewquestions interviewskills selfconfidence Jul 26, 2022
Woman being scared during an interview


It was 2005, my contract was coming to an end and I was looking for a new job. I had managed to get an interview with a Bank for a trading desk assistant role and so far the interview had been going very well.


Until that moment.


“Sooooo” the Desk Head asked. “You did accountancy at university”


My stomach sunk…


"Urm yes, a module of it” (Inside voice saying 'which I didn’t pay much attention to, disliked with a passion and avoided most of my lectures'). My palms started to sweat and the anxiety was rising.


Like a bloodhound sensing my fear, the two alpha males in the room started to drill me.


“Well tell us, how do you value a company?”


“What’s P/E ratio”


“What’s EBITDA"...


The questions kept on coming and I completely froze. It was my weak spot and they had nailed it. “I’m sorry I’ve gone blank”


The look of disgust on their faces said everything I needed to know. They were done, bored, next, please get this imbecile out of our sight.


But I wasn’t quite done.


“Have you got any questions” he asked. “Oh yes” I replied. I had prepped my questions well and wasn’t going to go out quietly, much to the absolute disappointment of them both.



As we ploughed, painfully, through the well researched questions I had, I watched the eye-rolling trader squirming on his chair (if only he could leave the room). So then, I decided I would do it...


A friend of mine had told me a killer question to ask in an interview. When he told me I said “What? You wouldn’t actually say that?!”


Yes. He would.


So I took a deep breath and I did.


                           “Have you got any reservations about hiring me?”


I wish I had a picture of their faces. The total gobsmacked look, that I would have the audacity to ask that question, given the total car crash of the last 15 minutes was something I’ll never forget. And they clearly liked it.


"Urmwell… no!” He responded. (Remember, with trading assistant you need people who will bounce back, be resilient, not take notice of bluster and blow from angry Alphas. This question proved it beautifully).


Now, you may be thinking, as I did at first, that it's a pretty aggressive question to ask. But I put it to you to consider it.

                            Why? Because of the gift it gives you.
If you can ask it in a tone that is curious, interested, eager to understand, it can actually challenge the interviewer to really think.


Do I? Do I have reservations?

What are the things they have been listing in their minds as to why you maybe couldn’t do the job?

Now, they may or may not tell you, but if they do, you have an opportunity to help them work through those reservations:

  • I’m not sure if you have enough relevant experience > Oh let me give you another example of where I do

  • I’m not sure you are the right cultural fit > You talk through your values that resonate with those of the company

  • I haven’t heard any examples of experience in X > Here’s a great one from my previous role

You can have a conversation to make sure you have articulated how fantastic you are, allying any fears or concerns they may have.

Done in the right way, it’s a brilliant way to ensure you’re both absolutely clear on if the job is right for you and you are right for the company.

So next time, I dare you. If your intuition feels it could be right, it may just be the best question you ever ask.



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