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Want the Upper Hand? Ask the Dumb Questions….

This story appears in the September 2017 issue of Entrepreneur. Subscribe »

My days as a rookie reporter were full of panic. I was interviewing people who worked in complex places — city government, local industry, hospital administration. I wanted them to trust me; I wanted them to think, This kid understands what I’m saying, and will accurately report it. But of course, I didn’t understand them. I didn’t even understand their language. A local mayor would say “RFP,” and I’d nod and make a note to google the letters when I got back to my desk. If I asked what it meant, I figured, the mayor would consider me a clown. 

Related: 5 Ways to Stop Worrying What Others Think

One day, however, an older reporter gave me some liberating advice. “Don’t be afraid to ask dumb questions,” he said. “A source would prefer explaining something to you than having you report it wrong.” He was right. Oftentimes, the question even charmed people, and then they’d tell me something surprising and perfect for my story.

This all came to mind recently while talking to Ankur Jain, the maddeningly smart 27-year-old founder of the Kairos Society. It’s an organization that incubates and invests in young founders, and I’d asked him to write the opening essay for this, our special “power of youth” issue, by explaining young people’s entrepreneurial advantage. The short version of his argument (which is on page 35) is: Young people approach industries fresh, unencumbered by the assumptions of older workers. Every industry is bogged down in its version of “that’s the way it’s always been done.” But young people are free of that. They ask basic questions — the dumb questions! — and then come to totally fresh conclusions.

Related: A Culture of Curiosity Is the Key to Building a Company That Learns to Improve

Ankur’s theory makes great sense, though I think he omits one key detail. Why do young people ask the dumb questions? Yes, part of it is their inexperience. But it’s also because they want to learn, to understand and to prove themselves — and at their age, they’re not afraid to show it. They’re focused less on holding down a job and more about figuring out how they fit into the world. And figuring that out is at the heart of entrepreneurship

So why should young people have a monopoly on this sort of behavior? Sure, older entrepreneurs have more to lose. They may be too concerned with maintaining their position. They may have larger egos to bruise. But they stand to lose a lot more by refusing to ask the dumb questions, and not examining the conventional wisdom, and ignoring the chronic problems. Our peers may be afraid to ask dumb questions, but that just creates an advantage for those who will.

If we shelve our pride and walk into new situations admitting what we don’t know, we’ll discover something remarkable: Nobody looks down upon us. People are helpful. And sometimes, their answers are so illuminating that we’ll feel inspired. 

Related: 5 Ways Childlike Curiosity Can (and Should) Inspire the Entrepreneurial Mindset

In this job, I’m constantly asking dumb questions. I do it internally, asking colleagues in other departments why certain things happen. When I find a “that’s the way it’s always been done” answer, I know I’ve found something worth changing. And today, 15 years after my first reporter gig, I’m also still doing it to sources. Now I’ll even joke about it. “Treat me like a 5-year-old,” I’ll say. It’s not that I like flaunting my ignorance — it’s just that when I fully embrace it, people’s guards go down. They want to help. They tell me something I don’t know. They do it patiently and insightfully. And that’s when I can see opportunity.


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