Why I Love to Ask The Dumbest Question in the Room

I am a relentless dumb-question asker.

I once asked a product manager at my company “Can you please explain to me what exactly the internet is made of?” This would be okay, if I’d asked in high school, in say, 1996. But this was about five years ago, when I had just begun working for a web hosting company, where one could argue that I should have known this answer.

There was a moment where I thought I might get shoved in a locker. But I was grateful when, with great patience, they whiteboarded the component parts of the business we were in and entertained probably 40 follow-up questions. At the end of the lesson, I heard something that has become a common follow-up to my dumb questions: “I think I actually understand it better now that I explained it to you. Thank you for asking.”

What I know is that I am never the smartest person in the room. This in part because I love surrounding myself with brilliant people, and in part because I delight in learning, in curiosity, in the thing I’ve never yet thought about. Dumb questions serve me well.

My test for whether to raise my hand and ask the question is to ask myself “Did I just pretend to know what she was talking about because it feels like everyone else does?” If the answer is yes, I make myself raise my hand.

From my experience, dumb-question asking has three big results:

1. I learn something new, and often gain more empathy in the process.

2. The teams I work with know they’ll never have the dumbest question in the room. I always do, and most often, someone pulls me aside and says “thank you for asking that — I didn’t want to say I didn’t know.”

3. Our teams become our teachers when they break down hard concepts into component parts.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store


Founder and CEO of Alpaca. Goals Nerd, Spreadsheet Enthusiast, and Runner.