The Greatest Advice I've Ever Gotten: “Ask Dumb Questions”

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My job is to ask questions.

But at the beginning, there were questions I too was afraid to ask.

They were the basic questions — the “I don’t know what that means” questions. These seemed dangerous to me. Damaging. I feared that if I revealed my ignorance on a subject, I’d also reveal myself as untrustworthy or unserious.

For example, when I was fresh out of college, I worked as a rookie reporter at a tiny newspaper. I’d interview the mayor about some public works project, and he’d tell me that the city just put out an RFP. But I had no idea what an RFP was, and I didn’t want to ask. (It's "request for proposal.")

So instead, I wrote it down in my notebook like this —

Then I’d go back to the office and Google around, hoping to figure it out.

One day, I mentioned this to an older reporter. He gave me transformative advice:

"Don't be afraid to ask dumb questions," he said.

Why? Well, here are four good reasons:

1. If your job is to know something, you better do your job.

2. If you show a genuine interest in something that someone knows, they feel good sharing their knowledge with you.

3. Simple questions are a sign of thoroughness. You’re proving your willingness to understand every part of what someone is saying.

4. People would always prefer explaining something now, versus you getting it wrong later.

He was right about all this. I started asking simple questions, and people were often charmed by them. They were happy to help. I mean, if you live in a world of RFPs, how often does someone care — genuinely care! — about what that is?

As I’ve gotten older, I’ve discovered just how scalable this advice is. It isn’t only for rookie reporters; it’s for anyone at any stage, in any industry.

Kairos founder Ankur Jain once made this memorably clear to me. He’s worked with a lot of young entrepreneurs, and a few years ago, he wrote an essay for Entrepreneur about why they can be so transformative.

“Young entrepreneurs' inexperience is their greatest asset,” he wrote. “They can come into an industry and ask questions about things that, for everyone else, have become unquestioned assumptions. Then, unburdened by old ways of thinking, they can challenge those assumptions to come up with entirely new ways of looking at a problem.”

In other words, young entrepreneurs’ power is their willingness to ask dumb questions.

Consider what happens next: If someone asks a question that, for everyone else, has become an unquestioned assumption, they will get answers that challenge those assumptions.

“Why are you doing it like that?” they could ask someone.

“Because that's how we’ve been doing it for 30 years,” could be the answer.

That seems like a wide-open opportunity for improvement.

But of course, young people don’t have a monopoly on dumb questions. Anyone can ask them.

All we need to do is put aside our egos, and double down on our curiosity.

I do this all the time now. It’s how I learn about new industries and new opportunities. “Treat me like a 5-year-old,” I’ll say, and people are happy to. I don’t need to pretend to know everything.

The way I see it, my job is to learn and grow, not to be all-knowing.

In fact, I even ask dumb questions when I’m supposed to be the expert! People buy consulting time with me, and I always begin by peppering them with basic questions about their work, their industry, and why they do what they do. In turn, they give me the granular details they might have otherwise skipped over — and that is often where the greatest insights lie.

In Ankur’s essay, he wrote about how “newness is valuable.” That’s not just true for ideas or efforts. It’s true for perspective too. And he said this reminds him of a favorite quote:

"A lot of people think innovation is thinking outside the box, when in reality innovation comes from thinking about a problem from a different box."

So, how do you find that different box?

That’s a good, simple, not-dumb question to ask.

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