How you should respond to these weird Wall Street job interview questions

While some Wall Street interviewers go by the book when it comes to asking candidates questions, others try to keep financial services job-seekers on their toes by throwing them curve balls. Some Wall Street job interview questions are just plain weird.

Broadly speaking, these kinds of out-of-left-field questions often involve ethical or moral issues or matters that are related to logic or math so that the person conducting the interview can evaluate your values and how you think when you’re put on the spot. You may have heard stories from someone who interviewed at an investment bank or hedge fund who was given a paper and pencil before being asked, “What’s 42-squared times 46-cubed plus the square root of 64?” and had to come up with an answer right then and there.

The following are weird, random, tricky or unexpected questions that Wall Street recruiters, HR executives and hiring managers may ask you during a job interview.

Candidate vs. candidate debate

“In terms of the weirdest or most interesting [interview tactics], there is a smaller financial services firm that always interviews multiple candidates for each position on the same day, and they’ll put two candidates in the same room and give each one a point of view and make them argue against each other,” said Brianne Toole, principal consultant on the investment banking team, Americas, at Selby Jennings. “They have to stick to a side and demonstrate clear communications skills."

What would you do if I gave you a million dollars right now?

Translation: Pitch me an investment idea.

“I want to know if you’ve got good ideas, and if you’re as passionate about the market as you say you are,” said Roy Cohen, careers coach and author of the Wall Street Professional's Survival Guide. “Prove it and be prepared to debate it, because the interviewer may rip apart your argument and expect you to defend it.”

Tell me about a trade where you lost your shirt.

In trading interviews, interviewers typically ask general questions, like “How do you manage risk?” Another common one is, “What’s a recent trade you’ve made that went really well?” However, you should also be prepared to answer the opposite: “What’s a recent trade that hasn’t gone so well and what did you learn from that?”

“You should have trade recommendations ready, and be able to talk about a bad trade and what you learned.” said Dylan Pany, principal consultant and the head of the trading team at Selby Jennings.

What’s the present value of a spouse, child or parent?

While rare, this one is designed to discombobulate the candidate.

“How do you evaluate what that individual is worth to you?” Cohen said. “It touches on emotional and psychological factors.

“Someone who is cutthroat may ask such a question with the idea, ‘Can you show me that in a difficult situation can you be ruthless if need be? Can you conduct an evaluation of an emotional situation on an objective basis?’” he said.

What three items would you bring if you were stranded on a deserted island?

Easy: A private jet, a GPS tracking system and a fully charged cell phone.

What they’re looking for with questions like these is insight into how you think.

“How would you survive, make it through a life-threatening situation?” Cohen said. “What’s your logic? When you’re trying to get something done quickly at an investment bank, your ability to think with speed and efficiency is paramount.”

How many bricks would it take to reach the top of the Empire State Building?

This is to find out how you go about determining what is reasonable and making mental calculations on the fly.

“I want to know the way you think, whether your thoughts are structured and if you have a reasonable process for the evaluation of complex situations,” Cohen said. “It’s important that you can come up with an answer that makes sense, whether or not it’s right.”

How many windows are in this building?

Every once in a while, you might get a brainteaser. The hiring manager doesn’t necessarily expect a correct answer; don’t get flustered and talk through your reasoning.

Why are manholes round?

Your guess is as good as mine. Just make sure your response sounds good and convincing.

Who is your best friend?

This was asked during a final round interview at Credit Suisse. “You are” is an incorrect response or you’d have the job already.

What do you think are U.S. and European banks' and asset managers’ biggest challenges in doing business in China?

Research various hot-button countries and markets so that you can come up with an intelligent response on the spot, even if it’s relatively brief.

How many gas stations are there in the U.S.? How many ping pong balls could you fit into this room?

This is another common type of question that catches people off guard, and there are a lot of different ways to ask it. Financial services professionals need to be quantitative, so hiring managers want to gauge whether they can think on their feet and arrive at a good answer.

Start by estimating that a ping pong ball is approximately one inch by one inch, and go from there. Hiring managers want to see your ability to quantify a number and explain how you got that answer.

If you owned the George Washington Bridge, for how much would you sell it to me?

This or something similar sometimes crops up in an interview for a sales or IBD role at a financial institution.

The best way to respond would be to guesstimate the approximate value of the scrap metal that could be salvaged from the bridge.

You are stranded on a desert island and can only take three items with you, what would they be?”

The correct answer is not “an unlimited supply of Hot Doritos, my wife and some playing cards.” The answer to this question is actually unimportant – the whole point is to gain some insight into your personality – but always bear in mind what the interviewer is trying to achieve.

Why didn't you get a full-time offer at the end of your internship?

“No, unfortunately I didn’t, and I still cannot explain why not. I had three reviews during my 10-week internship and they were all outstanding. At the half-way point, my MD indicated to me that I would receive a full-time offer. At the end of the internship, I expected to receive a written offer within a few days. Instead, a graduate recruitment person told me that due to headcount restrictions I would not receive an offer. My MD told me circumstances had changed and that she could not make an offer now, but for me not to give up hope because they may later get headcount authorization. I would love you to call the MD and 2 VPs I worked with to ask them about me. I’m very confident that each would say that I performed really well and that I should be hired.”

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