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Want a Job on Wall Street? 'Let Me Sleep With Your Girlfriend'

Wall Street is rude, it’s crude and it will eat you alive. So interviewing for a job on Wall Street is no different.

Paul Bradbury | OJO Images | Getty Images

It’s not a meet-and-greet tell-me-about this job or that experience. It’s more like a punch in the face. They’ll ask you hard questions, maybe inappropriate questions — all to see if you’re going to be able to run with the big dogs — or if you need to get your behind back on the porch.

“They’re looking for how you handle pressure. How you think on your feet. Are you the brightest of the bright? Are you a natural leader?” said Jeanne Branthover, head of global financial services at Boyden Global Executive Search .

Wall Street Oasis , a job-search site for financial careers, recently pinged readers for the hardest questions they were ever asked on an interview for Wall Street. The answers included such zingers as:

  • “You’re going to be working 110 hours a week here. Can you even handle that?”
  • Why don’t you have any offers yet? What’s wrong with you?”
  • “What single word would you use to describe yourself so I don’t walk out of here and forget you?” (Good answer: Unforgettable!)
  • “What line on your resume is the most bull****?”
  • “Do you view this as your dream career?” If you answer yes, “If in two years, you receive an offer for more money on the buyside, will you turn it down because this is your dream career?”
  • In an interview for a Goldman Sachs analyst position, the interviewer asked: “If you were shrunk to the size of a pencil and put in a blender, how would you get out?”
  • “What’s your outlook for cucumber prices over the course of 2012?”
  • In an interview where there were two interviewers, the one who was supposed to be the silent No. 2 asked just one question: "Are you trying to f*** us over?" The kid froze, the interviewer wrote in a comment on WallStreetOasis.com. The No. 1 interviewer jumped in: "Why didn't you just say no?!"
  • "If I told you that the only way you were going to get this job is if you let me sleep with your girlfriend, would you accept?"

When it comes to analytical questions like “What’s your outlook for cucumber prices?” or “How many tennis balls could you fit in this room?,” it’s not about the answer.

“It doesn’t mean you have the right answer — they’re trying to see how your thought process works,” Branthover said.

The kiss-of-death answer to any of these questions is “I don’t know.”

“You answer ‘I don’t know’ and that will get you out the door!” Branthover said.

Some of the other questions she said her clients have been asked include:

  • If you could choose, what brand would you like to be and why?
  • How many balls would it take to fill Central Park?
  • Have you ever cheated on your partner?
  • Did you ever tell a secret you promised to keep?
  • What is the biggest lie you’ve told — to whom and why?
  • Tell me, how would you go about killing a crocodile?

Questions for Wall Street jobs have always been tougher than those for most jobs, Branthover said, but they’ve gotten even tougher since the financial crisis.

“They want to know if you can really be a leader in tough times,” Branthover said. A lot of these leaders hadn’t been tested on that before the financial crisis. They survived and now they want to know — can you?

So, they may ask you questions like “What was one of the toughest decisions you had to make?” or “What was the hardest environment you’ve ever worked in?” Then, they’ll want to know what you did to solve the problem, get through the tough situation — and what you might do differently today.

Plus, with all the layoffs on Wall Street, there are fewer people to do all the work, meaning they really want the best of the best, the brightest of the bright.

When it comes to the inappropriate questions like sleeping with your girlfriend and cheating on your partner — the kind that would get the red light flashing in human resources at most companies — it’s about seeing if you can handle how brutal Wall Street can be.

“They’re trying to divide the men from the boys and the girls from the women,” Branthover said. “If you have soft skin, you’re not cut out for investment banking.”

They’re going to poke you with a stick and see how you react.

“They want to see that you’re not rattled by rudeness; that you stay on your feet and don’t look shocked,” Branthover said.

You don’t have to answer “Yes, you can sleep with my girlfriend” — you just have to not look shocked and have a quick comeback.

A good answer one person posted on Wall Street Oasis was: I’ve been with my girlfriend a long time and plan to marry her. If you so much as kiss her neck, I’d [bleeping] knock you out. That being said, I have a beautiful sister I’d be happy to hook you up with …

And that, my friend, is a lesson in how deals get done on Wall Street!

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Contact Pony Blog

  • Cindy Perman is a writer at CNBC.com, covering jobs, real estate, retirement and personal finance.

  • Based in Los Angeles, Jane Wells is a CNBC business news reporter and also writes the Funny Business blog for CNBC.com.

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