🚀 The art of asking dumb questions

How to prevent miscommunications by clarifying the obvious.

Remember when Ross drove to the airport to stop Rachel from leaving, only to realize he went to the wrong New York airport? That was rough. Ask any New Yorker—there's no easy way to get from JFK to Newark, unless your definition of 'easy' includes two hours, three modes of transportation, and a small existential crisis.

As a New York resident myself, I'm terrified of making that same mistake. Every time my wife and I travel, I not only triple-check the boarding pass, but I also ask her to confirm the airport. It's objectively a dumb question—obviously, I can read—but I'd rather look foolish for thirty seconds than miss my flight.

Why "Dumb" Questions Are Actually Genius

Let's be honest about the phrase "there's no such thing as a dumb question." There definitely are dumb questions. One of my favorite questions is a dumb question: “Is a hot dog a taco?” (Spoiler: it absolutely is, and a burrito is just a dumpling wearing a tortilla costume.)

But here's the thing—dumb questions are brilliant because they do something powerful: they expose core assumptions that everyone takes for granted.

Most catastrophic miscommunications happen at the foundational level. Everyone assumes they're on the same page about the basics, so nobody bothers to confirm.

When I tell you "get in the car so we can go," and you ask "which car?" that might feel like a dumb question. But it's necessary, because you don't want to hop into some stranger's Honda Civic while I'm waiting by my Toyota Prius, wondering why you're taking so long.

Your job as a PM (or any professional) is to be fearless about asking those clarifying questions.

The Science of Obvious Questions

Product Management in Practice nails this: "Things that seem obvious are those that carry the most potential for disastrous miscommunication. This is in no small part because the things that seem obvious are often the ones nobody wants to address explicitly."

Think about it—how many project disasters could be prevented by someone asking, "Wait, are we all talking about the same thing here?"

The PM's Secret Weapon: Strategic Stupidity

Product managers are taught to prioritize clarity over looking smart. Sometimes that means asking questions like:

  • "Are we talking about the mobile app or the web version?"

  • "By 'urgent,' do you mean this week or this hour?"

  • "When you say 'simple fix,' do you mean simple like changing a button color or simple like rebuilding our entire authentication system?"

I usually preface these with "sorry if this is a dumb question," but here's the secret: it's never actually a dumb question. More often than not, someone else is wondering the same, but is too afraid to ask.

Asking the clarifying question feels uncomfortable and embarrassing, but the math is simple:

  • Worst-case scenario: The team is already aligned, and maybe they mock you relentlessly for the rest of your life.

  • Best-case scenario: You've uncovered a massive misalignment that would have exploded later when it's exponentially more expensive to fix.

Your Action Plan

Here's my challenge to you: Ask more dumb questions. Your career will thank you.

This week, I dare you to:

  1. Ask one dumb question in a meeting, even if it seems obvious.

  2. Use the magic phrase: "Just to make sure we're all on the same page..."

  3. Embrace the awkward pause after you ask and let the magic unfold.

Remember, Ross could have saved himself (and us viewers) a lot of pain with one simple question: "Rachel, which airport?"

Don't be Ross. Ask the dumb question.

Reply and let me know what has helped you prevent miscommunications!

The Meme

Sometimes you just have to send it