Fearlessly Ask Stupid Questions

Dev Leader Weekly 107

Dev Leader

Aug 30, 2025

TL; DR:

It's not actually a stupid question
You can help improve the culture of your team
Join me on Monday, September 1st at 7:00 PM Pacific for a live stream (or watch the recording)!

Let's Talk About Stupid Questions

When you’re early in your career as a software engineer, there’s one feeling that seems universal:

I don’t want to ask this question because I’ll look stupid.

I’ve felt it. I’ve seen my teammates feel it. And I’ve seen entire teams get stuck in unhealthy patterns because nobody wanted to raise their hand and risk being “that person.”

But here’s the thing: those so-called stupid questions? They’re not stupid at all.

In fact, they’re often the questions that unlock clarity, reveal gaps in shared understanding, and prevent real issues from creeping into projects.

This newsletter issue is about why asking those questions is critical, what happens when you don’t, and how to make it a normal--even celebrated--part of your engineering career. In fact, I had a great example of asking stupid questions on Code Commute earlier this week:

The Hidden Cost of Staying Silent

Throughout my career managing engineering teams, one of the biggest lessons I learned wasn’t about writing code. It was about what wasn’t being said. This is the kind of stuff that says a lot about your engineering culture.

Smart, capable engineers would sit quietly in meetings while decisions were being made. Afterward, I’d find out they didn’t understand a key assumption, felt uncomfortable with the direction, or felt uncomfortable asking for more details.

Why didn’t they speak up?

Because they didn’t want to "look junior", uninformed, or out of step with their peers.

But the cost of staying silent is steep:

Wrong assumptions spread unchecked
People waste time chasing the wrong solution
Problems show up later when they’re much harder to fix

Silence is expensive.

Actionable Tip: Next time you find yourself thinking “this might be a dumb question,” flip it around:

If I don’t ask, and this assumption is wrong, what’s the cost?
If I do ask, and I’m right, what’s the upside?

Nine times out of ten, the upside outweighs the embarrassment you’re imagining. And the embarrassment you're imagining? Yeah. You're just imagining it 😃

Why Leaders Need to Model It

This isn’t just about juniors. This actually happens across many different levels of software engineers; it's just more commonly experienced or discussed with folks who are more junior.

If we want to shift our engineering culture so that everyone benefits, we need to start with modeling that behavior. Even the strongest engineers benefit when someone creates space for their questions, doubts, and half-formed ideas. And that starts with leadership modeling vulnerability.

On my own teams, I’ve made a point of asking questions out loud, even when I think I should already know the answer. Why? Because it shows everyone else that it’s safe to do the same.

Actionable Tip: If you’re more senior, a lead, or a manager, practice saying out loud in meetings (find your own words for this):

“I might be missing something here, but can someone clarify how X, Y, and Z work?”
“I thought it worked this way, but maybe I’ve misunderstood. Can you point me to where I can learn more?”

Your team will follow your lead. If you show it’s safe to ask, they’ll feel safer doing it too.

The Myth of “Looking Junior”

I once wrote on LinkedIn that engineers often avoid questions because they don’t want to “look stupid or look junior.” Someone twisted that into “Nick thinks junior engineers are stupid” because "junior" and "stupid" were in the same sentence.

That couldn’t be further from the truth. Juniors aren’t stupid. They’re just learning.

And so are seniors. And so are team leads. And so are managers. And so are executives.

We’re all learning all the time. The only difference is whether we’re honest about it. The real risk isn’t "looking junior" -- it’s staying quiet and staying stuck.

Actionable Tip: Reframe your fear:
Instead of thinking “If I ask, I’ll look junior,”
say “If I don’t ask, I’ll stay uninformed.”

Growth comes from facing the gap, not hiding it. In the most recent example where I did this within my team, I had made an assumption about something that wasn't true -- and now my understanding of that topic was reset.

I NEEDED to go find the answer. I NEEDED to ask. I NEEDED to lean into the opportunity to learn and understand. But that starts with asking questions about it -- and while that might feel scary, it's even scarier to continue not knowing how things work!

Creating a Team Culture Where Questions Are Safe

A strong engineering culture isn’t measured only by code quality or release velocity. It’s also measured by whether people feel safe saying "I don’t know". If team members don't feel comfortable operating within the team, there's a lot of room for improvement.

On healthy teams, questions are seen as:

Signals of engagement
Opportunities for shared learning
A chance to uncover hidden assumptions

The great news is that you can be part of driving your team's culture in that direction. The more people who model the behavior, the more the culture starts to take hold.

Actionable Tip: If you notice someone quiet in a meeting, invite them in with a low-stakes question. You might even do this on the side or offline so that you're not necessarily putting them on the spot:

"Anything unclear here that we should dig into together?"
"Do you see any risks we’re missing?"
"Let me know if you have any questions on that. I'd be happy to explain any of the details further!"

Often, the best insights come from the people who are hesitant to speak.

How to Ask “Stupid” Questions Without Fear

Let’s get tactical. How do you actually ask questions when you’re nervous about how they’ll land?

Here are a few strategies I’ve used:

Frame it as checking alignment
“I want to make sure I understand this correctly. Is it…?”
Pair your question with evidence
“I thought it worked this way because of X, but this seems different. Am I off?”
Use group learning as cover
“Maybe I’m the only one, but could we walk through that again just so we’re all clear?”

Nine times out of ten (that's a made-up stat, by the way), you’re not the only one confused. You’re just the only one brave enough to say it.

For now -- because others will follow suit when they feel comfortable.

Actionable Tip: Try this in your next meeting:
Ask one clarifying question, even if you think you already know the answer. You’ll either confirm your understanding or help someone else who was afraid to ask.

When the “Stupid” Question Sparks the Right Conversation

On Code Commute this past week, I shared a real situation: I had an assumption about how something worked on our team. Someone else’s question made me realize I might be wrong.

In fact... It made me realize that I must be wrong.

I asked around. Turns out, multiple people weren’t sure either. Each person I talked to was not confident in the full picture, but they were able to contribute to part of the answer.

We laughed about it, but it revealed a bigger truth: We had a blind spot as a team. That one “stupid” question turned into a shared conversation, which turned into clarity for everyone.

I had asked FIVE people for their thoughts on it. Collectively, we mostly had the answer, but I still took the opportunity to ask my manager in front of all of them so that I could demonstrate one more time that it's okay to ask "stupid" questions.

He tied together all of the loose ends for us. That’s the power of speaking up.

Actionable Tip: Treat every unanswered question as a shared risk. If you don’t know, chances are someone else doesn’t either. When you ask, you’re reducing risk for the entire team.

Final Thought: Run Into It, Not Away From It

Here’s the mental shift that’s changed everything for me:

When you uncover a gap in your knowledge, don’t minimize it. Don’t bury it. Don’t run away.

Run into it. That’s where growth happens.

The truth is, nobody knows everything. We’re all making assumptions. The difference is whether you’re willing to surface yours, challenge them, and learn.

So the next time you feel that fear bubbling up, remind yourself:

The dumbest question is the one you never asked.

Your career isn’t built on pretending you know everything. It’s built on consistently learning, growing, and helping others do the same.

Dev Leader Weekly