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One Sales Interview Question Best Unasked
Blog / Recruiting Salespeople / Oct 9, 2020 / Posted by Andy Rudin / 240 

One Sales Interview Question Best Unasked

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Occasionally, I read selling advice so off-the-wall, so misguided, and so dangerous that I smack my head in disbelief.  Here’s an example from an Inc. Magazine article titled, Recruiters, Share Can’t-Miss Interview Questions to Disarm Candidates.

“We interview candidates for both our internal company and for clients throughout the US. If someone is interviewing for a sales position, we’ve found that this question provides a lot of insight: What is the most expensive item you’ve ever purchased? The rationale behind it is that salespeople typically stop producing when they are ‘comfortable’ with their income, so this question provides insight into what may be ‘enough’ for them. For example, if I said that the most expensive thing I’ve ever purchased is a pair of $50 shoes, I may potentially not strive to make as much money as someone who answers, ‘I splurged and purchased a $500 pair of shoes because I knew that wearing them would be my motivation to make even more’.” [emphasis, mine]

The notion that a job candidate’s proclivity for luxury products portends sales success is absurd, and it promotes an odious misconception about salespeople. And, when used for vetting candidates, it’s also patently discriminatory. People who grew up with limited means are often less inclined to make self-indulgent purchases compared to those who grew up wealthy.

What about job candidates who must dedicate a chunk of their monthly income to support others in their family? What about solo-breadwinner parents who consistently save every month to provide a college education for their children? I bet you’ll find them buying footwear at Target, not at Gucci. The recruiter offering this misguided advice wouldn’t understand because her pathetically narrow point of view doesn’t allow her to.

I know top-producing salespeople whose penury makes Jack Benny look like a spendthrift. And I know some reps who can’t sell their way out of a wet paper bag, but that doesn’t inhibit them from diving head-first into a self-destructive pit of consumption and debt. So if you’re salivating over a sales candidate who swaggers into the interview wearing a pair of $800 Santoni Darian Cap Toe Oxfords, you might also want to uncover how much debt he’s carrying, and his stress level from being in hoc past his eyeballs.

But let’s look at this from another angle: if conspicuous consumption seems an appealing trait in a sales candidate, what risks could companies unwittingly absorb by choosing to hire such an individual? Could a person’s insatiable income drive expose the company’s customers, employees, suppliers, and partners to hazards like dishonesty, and predatory or manipulative selling? The questions are not facetious or hypothetical. When companies overlook the risks, and when sales reps are unchecked by internal governance, you often get unethical or illegal behavior, and fraud. Throw a hyper-competitive internal sales culture and retaliation into the mix, and I can almost guarantee harm will result.

If you want One Best Question in your interview arsenal, I suggest ditching “what’s your most expensive purchase” and replacing it with a question that’s infinitely more predictive of sales success: “when do you plan to retire?” If the candidate is 30-ish and says “not one minute past 40,” hire that person on the spot! I don’t care whether he or she wears $4.99 flip-flops, and drove to the interview in a ten-year-old Hyundai Elantra. Or took public transportation. Financially-Independent-Retire-Early or F-I-R-E: it’s 2020’s expensive wardrobe.

You can find loads of useful questions to ask sales candidates online. In practice, however, sales interview questions don’t differ much from those you’d ask a non-sales executive. The best guide I found comes from Harvard Business Review (7 Rules for Job Interview Questions that Result in Great Hires, by John Sullivan, February 10, 2016).

  1. Avoid easy-to-practice questions
  2. Be wary of [answers to] historical questions
  3. Assess their ability to solve a problem
  4. Evaluate whether they’re forward-looking
  5. Assess a candidate’s ability to learn, adapt and innovate
  6. Avoid duplication [by asking for information that’s already on a candidate’s resume]
  7. Allocate time for selling [your organization to the candidate]

If you want to add a sales wrinkle to your interview, I suggest inviting the candidate to talk about resilience. Salespeople experience frequent setbacks. In addition to learning how a candidate’s goals were over-achieved, their actual-to-quota performance, yadda-yadda-yadda, try to find out how they responded after they failed at something. The answer to that question will tell you much more about a candidate’s character than finding out how much their shoes cost.

About Author

Andrew (Andy) Rudin serves as Managing Principal of Contrary Domino, Inc., and helps B2B companies identify, assess, and manage a broad spectrum of revenue risks. He has a successful background as a technology sales strategist, marketer, account executive, and product manager.

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