By Thomas Koulopoulos

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Toss the canned interview questions and try these instead.

There’s no lack of sources for canned interview questions. A quick Google search on the phrase interview questions turns up about 20 million hits! Good luck with that.

In 30 years of interviewing people for roles in fast-paced startup cultures, I’ve come to realize that the vast majority of standard interview questions are useless. Yes, I know that sounds harsh, but the reality is that most interviewing guidelines have been developed for larger companies that have square holes they need to fill with square pegs.

If you wanted cookie cutter employees, you’d be running a cookie cutter business, and you’re not doing that–right?

Conformance, standardized qualifications, and a general lack of disruptive personality tend to work best for large companies. Not so for entrepreneurial ventures, where people need to grow with the organization, find opportunities on their own, and constantly question conventional wisdom. Besides, any reasonably smart person has rehearsed the answers to the standard roster of interview questions. “What’s your greatest weakness?” “I work too hard and expect excellence from those I work with.” Yeah, that’s what I wanted to hear–you’re hired! Going through this dance is just plain lazy. If you wanted cookie cutter employees, you’d be running a cookie cutter business, and you’re not doing that–right?

The most important thing I want to understand when hiring people is what drives them. Sure, they need to have a basic sense of the industry, the business model, and the market, but smart people can quickly ramp up. The key in hiring the best people is to look for foundational traits that speak to their sense of purpose, what drives them to achieve, how they deal with failure and success, how they think, and why they do what they do. Once you get close to these, you’ll know if someone is right for your organization.

So here are a few of the questions that I ask and why I ask them. My experience is that exceptional people like to be challenged with questions that go deeper, allowing them to reveal their values and strengths. Keep in mind that there are no pat answers to any of these. The intent is to see a person for who he or she is; that’s a great way to set the groundwork for the potential of an authentic long-term relationship.

1. Are you driven by the determination to succeed or the fear of failure?

There is no right answer to this question. What I’m looking for is what motivates this person to work hard. I do not judge ambition; it comes in many forms. Notice, by the way, that I’m asking if fear of failure “drives” him or her, not “paralyzes.” See the next question for more on that.

2. Why are you successful?

Successful people think a great deal about what they are doing and why. They always have a definitive and purposeful answer to why they have been successful. They also have a deep need for success that always eclipses their fears.

3. If today were your last day on earth, what would you most regret not having accomplished?

Regrets are horrible bedfellows. I’ve found that people who live with a keen awareness of what they need to accomplish are driven to be creative and resourceful; yes, they’re exactly who I want on my team. By the way, one of my favorite responses to this question was from a candidate who was also a private pilot: “Can you give me an approximate altitude above the Earth?”

4. How is who you are now consistent or inconsistent with the person you were at 12 years old?

To know a person, you need to know his or her journey. This single question may tell you more about the person you’re talking to than just about anything else you could ask. Don’t laugh this one off. Stick with it, and dig deep. It can take a bit of time, but it’s worth it.

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