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The Riskiest Question You Could Ever Ask In A Job Interview - But It Always Worked For Me.

This article is more than 10 years old.

During my twenties, I went through a career phase when I packed in dozens of job interviews in the manner of a serial dater. Much of it was purely for entertainment or to satisfy some burgeoning curiosity about the goings-on in my industry, as I was fairly happy in the company where I was working. To me, though, interviewing compared with the exhilaration of a first date. The intrigue of meeting someone for the first time! The nerves combined with the need to impress! The thrill of the power dynamic!

While some may find my diversion quite sad, I did pick up a few useful tips along the way—and one very high risk strategy that I believe may have something to do with why I was offered every job I interviewed for at the time.

The interview would inevitably close with my being asked whether I had any questions, and that’s when I seized my opportunity.

I’d look at the interviewer square on and let the moment hang in the air, to the point where his eyes would dart nervously or he would start to slowly close the notebook in his hands, assuming I had no questions. Then I’d ask, in a measured tone with just the right mix of seriousness and lightness, “If you didn’t offer me this job, what would the reason be?”

As I’ve only now discovered to both my surprise and chagrin, this question is one of the riskiest and quite possibly one of the most disconcerting to ask an interviewer. Yet every single time I asked it at the end of the interview, I ended up with a job offer.

Here’s how it played out back then: I’d ask the question, then sit back and watch my interviewer either squirm and smile nervously, or grin widely in response to being unsettled or intrigued by my forthrightness.

Then I would hear, “Well . . . I can’t think of any reason I wouldn’t hire you.”

I’d counter with, “Are you sure?” in a tone that conveyed that I expected him to consider his answer carefully. I felt any rational person would not want to seem inconsistent by denying there was a reason to reject me—and then not following through with a job offer.

Supposing an interviewer actually decided I was a right fit but had a few nagging issues. The question “If you didn’t offer me this job, what would the reason be?” can open a discussion and provide an opportunity to assuage any doubts an interviewer is having.

Here’s how such a conversation might unfold:

Interviewer: “Well, now that I think about it, I am curious as to why you were ‘away at sea’ for two years.” [I wasn’t – this is a hypothetical scenario]

Job Seeker: “It was a career break. I gave birth to baby Einstein, and he is doing so well that he’s just been entered into a graduate degree program at Harvard at age nine.”

or

“I used the time to reflect and decided I needed to contribute to a more meaningful world. I helped my friend Tom distribute shoes in Patagonia.”

or

“I was in prison, but I only pled guilty for the principle of it. I can’t stand injustice and I was protesting about such and such."

When the interviewer answers your question by mentioning what seems to be a red flag or a shortcoming in your skills and experience, you have an opportunity to redress it. And if you articulate your response logically and succinctly, you could potentially turn around the interviewer’s perceptions and land yourself a job.

Asking my pointed question worked for me in one specific era—the 2000s—and one particular type of industry—a creative one. It’s quite possible that my cheekiness may have impressed my fellow journalists, who are not averse to sneaking in inappropriate questions at the end of interviews themselves. However, it may not work in other situations.

I posed the interview scenario to two fairly senior professionals in the finance industry, and their reaction to my question bordered on apoplectic.

A London hedge fund executive said, “I would think totally inappropriate and I would be unimpressed. I would also think complete lack of judgment. The question to leave with would be: ‘I’m concerned you might think I don’t deserve the job because of X; however, I think this should not be a decisive factor because of Y.’ If you have to ask why you might not be getting the job, it means that you are insecure and ignorant.”

A New York investment banking executive said, “I’d think this person is determined and interested in the job, but in a way that’s questioning the judgment of the interviewer and that’s when I’d get upset. I’d think, ‘They can get lost.’ I would answer the question with, ‘Because we will benchmark you against other candidates and there may be someone with more experience or knowledge in the field.’ And then I’d close the interview.”

So that’s a resounding no from the finance industry.

Interview expert Danielle Weinblatt, CEO of ConveyIQ, a startup that allows employers to screen candidates and conduct job interviews online, concurs. “I don't think this is an appropriate question. It puts the interviewer on the spot and makes them feel uncomfortable. I would assume that this candidate would find it difficult to be appropriate in client situations or circumstances with other team members.”

Well then. I shall try not to take all of these comedowns too personally.

According to Danielle, if you want to understand what the interviewer is looking for, the better way to phrase the question would be: “What are the qualities you think it takes for someone to be successful in this role?”

She goes on to explain, “As the interview is concluding, I would then reiterate why I possess those qualities. It creates a great summary of your candidacy and reinforces the core qualities that the interviewer is looking for. If you really want to improve your chances of landing the job, ask questions that demonstrate knowledge of the organization and show that you have done your due diligence.”

I did find one executive who responded somewhat positively to the question: the head of recruiting at a well-known global financial services company.

“I think this shows that the candidate is eager to understand where they stand in regard to the position and what they could possibly do better to win over the interviewer. With the shifts in the employment market recently, I think more candidates want to have clarity about their viability because they are not interviewing at as many organizations, so the competition in the candidate market at the moment is extremely high. Personally, I would think this was a gutsy question and not at all inappropriate.”

Overall, I have to conclude that mine is a high-risk question, but if you work in an industry that may welcome your chutzpah, asking it may be a risk well worth taking.

Follow me on twitter @maseenaziegler

UPDATED: January 2018 to reflect the change of name of Take The Interview, now known as ConveyIQ.