To get into the University of Chicago, applicants have to write an essay based off promptsprovided by the school. This year, some of the prompts include, “What’s so odd about odd numbers” and, “Were pH an expression of personality, what would be your pH and why?”

These sorts of questions are typically associated with techy new-age startups. For example, at Google, candidates used to be asked questions like, “How many golf balls can fit in a school bus?” and, “How much should you charge to wash all the windows in Seattle?”

Frankly, these are stupid questions. And many companies are moving away from them, including Google itself.

That said, there still might be some use to these stupid interview questions – if asked correctly.

Stupid Ways to Ask Stupid Questions

The worst part about the University of Chicago’s prompts is not the questions themselves but the way they are assessed. Business Insider interviewed the school’s admission officer, Garrett Brinker, and he said there is no model answer.

“We are at liberty to lightly edit the essay prompts in order to give students additional intellectual freedoms or possibly spur their intellectual creativity a bit more, but there’s not necessarily one or two or even ten types of model answers that we’re envisioning throughout this process,” Brinker told BI.

This is a questionable approach. Studies show that structured interviews with structured assessment criteria work better than unstructured methods because, among other reasons, they can be tested and improved over time. UChicago’s unstructured approach, meanwhile, is prone to an assessor trusting their “gut instinct” instead of objective data and is susceptible to bias.

Laszlo Bock, Google’s senior vice president of people operations, told The New York Times that his company got away from asking brainteasers for the aforementioned reasons. Instead, Bock prefers a more structured approach.

“On the hiring side, we found that brainteasers are a complete waste of time,” Bock told The Times. “They don’t predict anything. They serve primarily to make the interviewer feel smart.”

“Instead,” Bock continued, “what works well are structured behavioral interviews, where you have a consistent rubric for how you assess people, rather than having each interviewer just make stuff up.”

A Smart Way to Ask Stupid Questions

While often the execution of these questions is muddled, the concept behind them is sensible. Essentially, the goal of these types of brainteaser questions is to gain some valuable behavioral data from candidates to see how they really think and act.

For example, Warren Buffett gives applicants puzzles and makes them give presentations to determine their intelligence and energy level. The key to this approach though is to deliver these questions in a structured way and assess responses in a structured way, so more objective data is garnered.

New gamification strategies, as an example, essentially have candidates play games to capture their true personalities. These games have a clear assessment system that determines if a candidate does a certain action, they are fast-on-their-feet, or if they do another, they are unafraid to fail, as an example.


In reality, there is probably a very limited need for brainteaser questions in job interviews. Frankly, a better solution is to ask realistic scenario questions that could come up on the job or drill in on specific skills that are essential to the position.

However, there could be some use to these brainteasers, if asked correctly. But the key is to do it in a structured way, so they produce reliable, testable data.

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