We asked Entrepreneurs' Organization (EO) members in the recruiting and staffing industry to share the questions they ask and the methods they utilize to get to the root of a candidate's skills, personality and motivators necessary to flourish in a specific role.

Hiring is one of the most critical and challenging aspects of growing a business. Depending on which open positions you need to fill and your level of anxiety about the process, you might consult expert recruiters, hone creative listening skills or ask team members to weigh in--but ultimately, the decision is yours as a business leader. So, you better get it right.

But a one-size fits all interview process just doesn't cut it. Candidates are familiar with the well-publicized array of conventional interview questions. If you take the cookie-cutter approach, you'll likely hear practiced, well-prepared answers that reveal little of a candidate's true personality and motivators.

Throwing job candidates a curveball with thought-provoking questions tailored to the specific role at hand, however, can yield invaluable information about performance and personality traits that are great predictors of success or failure, enabling you to make an informed decision about the next key member of your team.

We polled EO members about the surefire questions and methods they've used to reveal  a candidate's aptitude for sales, recruiting, finance and the C-suite. Here's what they shared:

For sales positions

"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'." ? Michelle Fish, Founder and CEO, Integra Staffing

For recruiting positions

"Our company hires recruiters. Over the past seven years, I've developed an out-of-the-box interview process that gets to the heart of the skills and flexibility necessary for recruiting. During the first interview, I don't ask any questions at all. Instead, I give candidates the floor and let them interview me for up to 90 minutes. It's a fascinating journey: I get to see how intellectually curious they are, how well-prepared they are, and it's a great indicator for how they handle adversity. It gives me a chance to watch them take the reins and control an unexpected situation and evaluate them in a positive but unique environment. The best candidates flourish in that environment. The ones who panic or falter move on to other opportunities. I'll never go back to the traditional method of interviewing!" ? Adam Morris, CEO, SalesFirst Recruiting

For C-suite positions

"For C-level positions, we tend to hire based on journey rather than destination. To us, a candidate who went to a 'mediocre' school can be far more impressive than an Ivy Leaguer if they went through a difficult journey to get where they are. It typically means they can learn quickly and navigate adversity, which is often what executives we hire face. We also look specifically for candidates who behave like enablers and servant-leaders for the teams they'll be leading. The ideal candidate shouldn't see any work as being 'beneath' them. A few of the questions we ask are:

  • How did you pay for your education?
  • How have you enabled people around you to succeed in the past? 
  • What was your biggest failure as a leader?

We consider it a red flag if the candidate speaks about the teams they work with as being 'their' employees or beneath them in any way. Another way we filter for this is by taking them to a restaurant and watching how they interact with and treat the staff. It can be very telling." ? Mehtab Bhogal, Karta Ventures

For Millennials

"I predominantly hire Millennials, who tend to come with little--if any--work experience. That's not a problem in our company because we are big believers in cultural fit trumping all else. For my team, the ability to hustle and true love for the concept of work is the core competency. The question I ask every prospective hire: What was your first paid job? Then I ask for context--where they worked, why they worked, how old they were. Applicants who didn't start working until after graduating from college? Not for us. Applicants who started hustling as soon as they were legally allowed? Yes, please! It's the one common denominator among everyone on my team; we share our first-job stories with the same contagious passion I'm looking for in interviewees." ? Marina Byezhanova, Co-Founder, Pronexia

For finance positions

Finally, while the following insight isn't from a recruiter, the question he asks finance candidates is a worthy contender.

"For finance roles, we find this question highly revealing: If there was a machine that produced $100 bills for life, what would you be willing to pay for it if you had access to the capital to purchase it? The answers we get vary, but they typically show whether a candidate can think both logically and creatively. You get some insight into how they reason and how they react to being put on the spot with a thought-provoking question that doesn't necessarily have one 'right' answer. The best candidates give a creative answer with a basis in logic." ? Jon Ostenson, CEO, 10xFive