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Art of the Interview: 3 Questions Startup Founders Love

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I have worked with dozens of founders over the years and never tire of their passion for their “baby.” The average entrepreneur is not just building a company. They are looking to disrupt and improve the world. It’s more of a calling than an occupation.

When interviewing an entrepreneur, there are certain topics that are best to avoid such as “What is your exit strategy” and “What advice would you offer to other founders?” An exit strategy assumes that your goal is to cash out and that success is only measured in dollars and cents. Advice is as complex and nuanced as the individual entrepreneur and best left to the reader to discover for themselves. So, what are the questions that will get the conversation flowing?

To get those answers, I asked my client Steve Gerber, the CEO and co-founder of the tech startup, i2tag to share his top three.

“What’s the story behind your company?”

A good place to begin the interview, says Gerber, is to ask about the company’s beginnings. Like a new parent excited to share their baby’s latest milestone, founders are equally eager to share their company’s origin story. This question is not only the perfect icebreaker, but it gives the interviewer the opportunity to show both curiosity and appreciation for the hard work that goes into birthing a new company.

“Who were the people who have been the most helpful in getting you to where you are today? How did they impact your life and your success?”

This is another good question to ask, according to Gerber. We all love the idea of the lone genius who single-handedly creates a company, but it’s a myth. Elon Musk is rightly recognized as the visionary behind Tesla but he didn’t achieve his success on his own. This question gives a founder the opportunity to show gratitude and humility. It also humanizes them. It makes us care about them and root for their success.

I have always felt that the best part of the Oscars is when an actor is on stage giving their acceptance speech—and they stop to thank their spouse and/or parents for supporting them. They remember and honor the people who were there before the actor stepped into the spotlight; the ones who believed in them when they doubted themselves. The people who support us are typically not famous or world-renown. But without them, we couldn’t have achieved our best, whether you are an Oscar-winning actor or the founder of a successful startup.

“Have you had to pivot your business product or service yet?”

The last question is one that is rarely asked but should be, says Gerber. Most interviewers will ask founders to share how they’ve overcome failure and may even lead with the overused phrase “fail fast, fail often.” What is important is not the times a founder failed — of course they have and yes, you do grow from failure. What matters is the founder’s ability to stay open to a pivot in order to better meet customer needs and calibrate accordingly. To
embrace change when it becomes clear that doing so will help the customer and the startup. A founder who is willing to admit that they don’t have all the answers is an inspired leader. Someone who can pivot based on market research and feedback from their early adopters demonstrates grit and resilience, the two key attributes of every successful founder.

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