Yesterday I interviewed for a desk trader job. It went pretty well. The pay's good and the commute's good and I really think we hit it off. I gave a presentation and then we had a string of interviews.

When I interviewed with the director he asked a strange question and I didn't know what to say: "would you go to jail for us"? It caught me completely off guard. I kind of waffled and told them it depends and I think they were disappointed in my answer.

Which is why I'm asking: what would have been the best way to respond to this question?

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    "Is there an expectation that will be required?" would have been my response. – IDrinkandIKnowThings Sep 12 '18 at 12:56
  • "Absolutely Not!" is the only appropriate answer. – brandonstrong Sep 12 '18 at 20:17

10 Answers 10


My answer would have been a simple no.

It's entirely possible that it was a test, and that's the answer they were looking for. If they were hoping for anything other than no, I personally wouldn't want to work for them.

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    Indeed. Regardless of what's going on and why they ask the question, the answer is the same. Consider it a test both for them and for you. – Mast Sep 8 '18 at 6:37
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    I would have replied with a much more expansive answer of "Hell no". – Peter M Sep 8 '18 at 13:44
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    The proper response is Hahahahahah, good one – rath Sep 9 '18 at 16:38
  • In my not entirely humble opinion, the ideal response is to say "No", and then calmly wait for the next question. But of course it's not easy to come up with the ideal response under the pressure of a job interview. That's what makes it a bad question. The way someone answers it doesn't necessarily give the interviewer any useful information. – Keith Thompson Sep 10 '18 at 18:50
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    One possible extension to the candidates answer (and maybe worth adding here, as you imply it) would be something like "No, and if I noticed some illegal process happening that would make the company liable, then as part of my job, I would inform my manager discreetly. I would expect the company to resolve it as a priority." – Neil Slater Sep 11 '18 at 7:57

what would have been the best way to respond to this question?

I believe that honesty is usually best.

I would answer "No. And if that's an expected part of the job, then I thank you for your time but will leave now."

If the director responded with anything other than complete assurances that jail wasn't expected and that they were hoping you would be honest and say No, I would get up and walk away.

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    100% this. Note that there's a subtle but important difference between going to jail because of something you did at work, and going to jail for the company. The latter sounds like they're interviewing for patsies. – Steve-O Sep 8 '18 at 14:17

This is such a bizarre and pointless question that I would probably thank them for their time and end the interview.

I suppose it could be an honest company making a ham fisted effort to smoke out dishonest applicants, or an equally unsubtle filter for applicants willing to make the company interests primary over their own interests. Neither possibility makes the company seem very appealing to me.

Or, I suppose, it could be a company actually engaged in illegal conduct, looking for accomplices who won't squeal. In that case the question seems pretty stupid. You couldn't trust the answer, and hinting to strangers you've just met that your company is engaged in illegal activity is no way to run a conspiracy.


Which is why I'm asking: what would have been the best way to respond to this question?

"Not for the pay you're offering."

This answer puts the ball back in their court, if it's a joke we all have a giggle, if they persist, then I definitely would NOT be interested in a job with a likelihood of going to jail. This is one of the most basic strategies for dealing with questions you don't really understand the motivation behind. Pass it back for clarification or the bin. You don't try and psychoanalyse everyone on insufficient info and get defensive etc,. just simply pass it back.

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    I agree, but feel like the body language and tone definitely has to be correct to go with this one. If you say it while laughing and clearly joking, then you're clearly taking the whole question as a ridiculous joke (which is hopefully all it is.) But that's very different from staring straight at them and saying it with a straight face - that makes it sound like you're straight up interested in negotiating to work in a criminal role! – berry120 Sep 11 '18 at 8:55
  • @berry120 What does it matter if s/he looks bad to potential criminals? If they do think you're negotiating, then tell them you'll think about it, then decline from a safe distance/phone/email. – Carduus Sep 11 '18 at 13:53
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    @Carduus Because if the question was asked as a joke, you do still want to work there, and your answer makes them think that you'd seriously consider committing a crime for the right money, you'd be struck of the candidate list immediately. – berry120 Sep 11 '18 at 13:58

Taking time to think about that I found some possible reasons.
Your problem was not to have this time.

The company

  • is into illegal activities. Then saying no means you are a danger to them. Say no! As loud as you can. (except if you really want to go to jail)

  • wants to know if you are spontaneous enough. Then something like "no, I guess it's hard to work for you there, I prefer a normal office" would be a good answer. Unfortunately you had no time to find such a response.

  • wants to learn about your honesty. Who would go to jail? If you say yes it probably was a lie. How reliable is the whole interview then? Better say no.

  • wants to find out if you are a yes-person because they don't like to employ one. Better say no.

  • actually wants to employ a yes person. If this is not an environment for you to work in you better say no and are happy to be not employed there.

  • Another possibility: The company is probing how an employee with a lot of responsibility will deal with encountering illegal activities. They may want a candidate who will point out "that's illegal" through the management chain, although the presentation of the question is a bit removed from it, this is better framing for the interviewer than "What would you do if you encountered something illegal?" where they could expect stock answers. – Neil Slater Sep 11 '18 at 8:05

I would have ended the interview on the spot, just thanked them for their time, got up, and walked out of the room, without giving an answer.

This question is beyond inappropriate, it's bordering on illegal. I would take this question as a threat: "If you work for us, we expect that if something goes wrong, you will be the fall guy, prepare for time behind bars now". That is not something I (or you) should be interested in, and the mere suggestion that they might do such a thing would completely disqualify them in my opinion.

Furthermore, if you found this company through a third-party recruiter, I would definitely report to the recruiter that you were asked this question, and I would strongly consider reporting this company to the local authorities.


What a weird question.

But now that I thought about it the answer should probably be along the lines: "I always expect my employer to do the best to comply with the law. In case that there is a case of non-compliance I primarily will consult with the compliance department and I will follow the law as to my personal interactions with the law enforcement in order to avoid further implication of the company".


It caught me completely off guard. I kind of waffled and told them it depends and I think they were disappointed in my answer.

I believe it was a trick question to test how well you'd do given odd situations. I'm assuming this because it is such a odd question and unless the company had questionable history, I highly doubt they're into illegal activities or expect you to go to jail as part of the job. Assumingly you're not interviewing at the jail or prison where they expect you to frequently enter a jail cell.

They were disappointed by your reaction and answer. You hesitated and was taken aback and answered untruthfully. Depending on how they are, they probably passed on you given this reaction. It could be that the position you were hired for might have people asking odd ball questions or dealing with odd situations and they wanted to see how you'd react.

I don't think there's any right or wrong way to answer. They wanted to see if you'd keep your cool. They probably thought you rehearse your interview and maybe throwing a odd ball at you to see how well you'd do with unexpected results. Whatever the case is, keep cool, answer honestly. "No, I would not go to jail for my employer, nor would I expect my employer to be into illegal activities."


In the financial industry, if they're expecting you to say "yes", then there's a chance you will actually go to jail for them at some point in the future. Any financial professional does a voluminous amount of training, compliance and so on. They might have been egging you on or just messing with you. If you cite your training, certification, AML and other professional knowledge, then that should be that.


Answer: no. Going to jail means you'll have a criminal record, which will kill your chances of ever getting a decent job in the future. This company most likely won't be around forever, and it's not worth sending your whole future down the toilet for them, even if it's a well-paid job.

My guess is that they wanted you to say "no"; to see if you're an honest and moral person (i.e. someone any self-respecting company would want to hire, instead of someone untrustworthy and reckless). So for "how to answer the question", that's the short answer, but if you ever get hit with something similar again, stay calm, think about it rationally and you'll come to a sound conclusion.

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