Entrepreneur

Ask That Dumb Question
Take it from a journalist: You can learn a lot when you shelve your ego.
M
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.
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.
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.
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.
Jason Feifer
jfeifer@entrepreneur.com
@heyfeifer
GROOMER, CASEY GEREN
10 / ENTREPRENEUR.COM / September 2017
Photograph / NIGEL PARRY