Use These Unconventional Job-Interview Questions to Find

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Amid the tight job market of the past few years, recruiting talent has been one of the biggest challenges at many organizations.

With a new book called Talent, economist Tyler Cowen and investor and entrepreneur Daniel Gross tackle the question of how to best go about this and find people with a creative spark. They posit that top candidates are too often overlooked and reject some traditional hiring assumptions and practices.

“Intelligence is usually overrated,” they conclude on the basis of a review of the research into IQ scores, earnings, and professional achievement. (p. 79) They argue that instead, top performers exhibit a combination of traits the authors call “the whole package” (p. 85), including a commitment to practice—the equivalent of a pianist playing scales—for continuous improvement. “What you want is a kind of conscientiousness directed at the kind of focused practice and thus compound learning that will boost intelligence on the job,” they write. (p. 121)

They believe that “stamina”—evidence of untiring drive they see in the likes of Bob Dylan—is “one of the great underrated concepts for talent search.” (p. 119) Other traits they recommend looking for include what they call sturdiness, or consistency of getting work done every day, and generativeness, or openly bubbling with and sharing ideas. Their focus is on hiring workers who generate new ideas and approaches or “inspire others by their very presence, leadership, and charisma, regardless of the context” (p. 9) and they believe spotting talent is itself something a hiring manager can improve through practice.

Talent outlines a provocative approach to hiring, in contrast with many companies’ efforts to standardize hiring processes—and interview questions—to reduce the impact of individual biases. Cowen and Gross dismiss such approaches as “bureaucratic methods of hiring” (p. 24) and instead focus on “unstructured” interviews where the individual judgment of the interviewer is a deciding factor. “Interviews are essential, and because so many organizations rely on mindless bureaucratic approaches, the bar is low and the payoff high,” they write. (p. 27)

Cowen and Gross believe that hiring managers should endeavor to establish trust with candidates, avoid asking obvious questions, try to get candidates to tell stories about themselves, and ask for specific pieces of information.

Here is a sampling of interview questions that they recommend, along with the reasoning behind each one:

  • What are the open tabs on your browser right now? This sheds light on “intellectual habits, curiosity, and what a person does in his or her spare time, all at once,” the authors write. (p. 21) They believe that what you do in your free time can help reveal personality and how you approach self-improvement.
  • What did you do this morning? This is a simple opening question that can elicit a story, shift someone into a conversational and less fake mode, and reveal how a person organizes ideas.
  • What’s something weird or unusual you did early on in life? What views do you hold religiously, almost irrationally? These are uncommon questions, meant to bump candidates outside of prepared answers and familiar territory, and help you assess their resourcefulness, personality, and self-awareness. If candidates struggle to answer, the authors recommend repeating the question or sharing your own answer to give them time to think—but not backing down from requiring a response.
  • If you joined us and then in three to six months you were no longer here, why would that be? What are 10 words your spouse or partner or friend would use to describe you? These questions require specific responses.
  • What have you achieved that is unusual for your peer group? This is a question they likely haven’t prepared for, so it gives you a sense of how they think and evaluate themselves.
  • How ambitious are you? The response is difficult to fake, and offers valuable information about their goals and how good they are at defending them.
  • When have you experienced great regret in the workplace and why? How much were you at fault in that interaction? Cowen and Gross believe the distance created by online interviews provides openings to ask such confessional, revealing questions.
  • Can you give us an instance where you perceived a team problem at work and stepped in to fix it? What exactly was your remedy? This tests for the ability to identify a social problem and its solution.
  • What do you think of the service here? The authors recommend doing interviews in places like restaurants and coffee shops. With this question, “you are giving the candidate a chance to express emotions, register grudges, and evaluate new and unexpected settings, all in relatively unfiltered form,” they write. (p. 38)

Cowen and Gross suggest some questions to ask a candidate’s references, originally proposed by Stripe CEO Patrick Collison:

  • Is this person so good that you would happily work for them?
  • Can this person get you to where you need to be way faster than any reasonable person could?
  • When this person disagrees with you, do you think it will be as likely you are wrong as they are wrong?”

The authors also explore research about why women, disabled people, and workers of color face discrimination in the hiring process. “Screening correctly for the overlooked late-career woman, the non-obvious misfit producer, or the hidden gem is your best bet at building a unique, motivated, and loyal team,” Cowen and Gross write. “Identifying underrated talent is one of the most potent ways to give yourself a personal or an organizational edge.” (p. 8)

To be sure:

  • The book extolls the practices of prominent male Silicon Valley figures including Peter Thiel, Elon Musk, and Marc Andreessen, and provides relatively few examples of exceptional female talents or talent finders beyond Greta Thunberg, N.K. Jemesin, and fashion supermodels.
  • While the authors acknowledge they’re writing from the perspective of two white men, their section on racial bias in hiring comes off as naive in places. Visiting a Black church or an unfamiliar country like Finland is among their advice for experiencing different perspectives.
  • The focus on refining the individual judgment of hiring managers or investors and dismissal of structured “bureaucratic” approaches to hiring likely leaves greater openings for bias and individual blindspots to influence decisions.
  • The authors frequently use financial earnings as a primary way to measure professional success and its correlation with intelligence and other traits. Compensation is arguably a very one-dimensional measure of achievement, skewing any analysis of the traits that correlate with success. Thunberg, for example, presumably ranks poorly for earnings despite her extreme impact and prominence.
  • Cowen and Gross are self-congratulatory and self-indulgent at times. Cowen “consumes no coffee or tea. The engine is within,” they write. (p. 128) The book inexplicably quotes Gross’s “online memoir” about the results of a research paper rather than just summarizing the paper outright.
  • The authors assert that there isn’t an existing go-to book on talent search. One in this category that I’ve found valuable over the years is The Talent Edge by David S. Cohen.

Memorable anecdotes and facts:

  • Elon Musk personally interviewed the first 3,000 hires at SpaceX because he wanted to make sure they were hiring the right people.
  • At least 20% to 40% of the growth in US economic output since 1960 stems from the better allocation of talent, according to the authors, as women and workers of color are better able to access jobs they are suited for.
  • Former Y Combinator president Sam Altman wrote a computer program to measure how fast founders the VC firm had funded responded to his emails and found successful ones replied “mind-blowingly” faster on average than those who weren’t successful.
  • Research in Finland found that higher IQ was correlated with the likelihood someone was an inventor, while the level of parental education played a larger role in whether one was a lawyer or doctor.

Notable quotes:

  • “If the person does engage in daily, intensive self-improvement, perhaps eschewing more typical and more social pursuits, there is a greater chance that they are the kind of creative obsessive who can make a big difference.” (p. 2)
  • “A world of rampant inequality and insufficient opportunity is, among other things, a world failing to recognize and mobilize talent.” (p. 14)
  • “During an interview, you can ask anything (legal) in the known universe and explore any angle you wish. What a splendid but also baffling position to be in.” (p. 25)
  • “The best interviews are not formal interviews at all.” (p. 38)
  • “Contemporary society still too often suffers from ‘lookism,’ which is expecting smart and ‘able’ people to fit a very particular physical picture of how to move and act and sound. To whatever extent possible, try to liberate yourself from those biases.” (p. 169)
  • “A significant subclass of potential workers goes around with many of their talents invisible or at least significantly harder to spot.” (p. 198)

The bottom line is that Talent is a provocative tour of the considerations and assumptions that go into hiring. The authors’ recommended interview questions are especially thought-provoking.

A special offer for Charter subscribers: See what business leaders are saying about Talent on the new books discovery app Tertulia, which is currently offering the book at 25% off. Head to the Apple App Store to download Tertulia,

You can also order Talent at Bookshop.org or Amazon.

Read our book briefing on Impact Players, which examines the attributes of standout individual contributors.

Read our briefing on Bias Interrupted, which covers ways to fix the hiring process.

Read all of our book briefings here.

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