Asking Stupid Questions

While I’m riffing off of Dan Luu’s post about not being afraid to look stupid, I want to think about asking Stupid Questions.

In this post I want to explore:

  • What is a stupid question?

  • What are some examples?

  • Why would I want to ask them?

  • Why don’t I ask them?

What is a stupid question?

I’m thinking of a specific type of Stupid Question.

Some questions are not sensible to ask because they may hurt someone’s feelings or because they may cause some sort of material harm. I’m not thinking of those questions.

I’m thinking of questions that are legitimate for the venue, have a positive intention, won’t cause harm, yet — for some reason — I feel I shouldn’t ask.

Here are some reasons I can think of:

  • It seems like everyone else already knows the answer.

  • It seems like the answer should be obvious.

  • It seems like others don’t want to talk about it.

  • It feels too “basic” and others have moved on to more “advanced” topics.

  • I’ve already been given an answer and the answerer proceeded as if their answer was sufficient.

I think a question feels stupid when, for any reason, it seems like I should already know the answer.

For me, the hesitation stems from my desire for reputation. I don’t ask because others will think less of me when I ask these questions.

But, I’m getting ahead of myself. I’m going to stop defining to see if I can come up with examples.



“What is a stupid question?”

feels like a stupid question. It’s so basic that it seems like I should already know the answer. It feels a little embarrassing to write a blog post about something so simple.

Another common example that I run into is

“What does this acronym (or initialism) mean?”

This feels particularly stupid when it’s an acronym I hear used, but not defined, often.

I remember one particular time this question was asked. I was on a team that was rewriting an app that was only ever referred to by an initialism. Finally, someone asked what the initials stood for. No one knew, not even the current system maintainers.

Another example for engineers is something like,

“What do you use for logging?”

It’s a pretty basic question that can reveal things like:

  • we use fifteen different logging libraries

  • we don’t have any organizational documentation about logging

  • we don’t even agree on the type of logging

Here’s an awkward, but simple, one:

“Why are we doing this?”

Every time I’ve asked this, even before a project is started, I’ve been met with resistance to change. Even when the answers aren’t particularly great. I’ve resisted this type of question myself. Once I start working on a plan, it’s hard to change my mind, even when my original reasons are revealed to be faulty.

That leads to another stupid question, something along the lines of, “What questions can I ask?” In reality, this question might be formed as “What type of feedback are you looking for?” This stupid question is basically asking for permission to ask stupid questions, while giving permission to deny stupid questions, focusing only on easier topics.

I (and I wonder about others) often see asking “why?” as a stupid question. It’s the reason I get annoyed when my three-year-old asks me “why?” for the fiftieth time. He’s engaging in first principles and trying to understand the world. I’m trying to move on without being bothered to explain myself or to think about what I’m doing. It’s inconvenient.

Why ask a stupid question?

Now I have some idea of what a stupid question is. I’ve thought of a few examples. Still, why would I want to ask a stupid question?

First, I have to acknowledge that asking a stupid question will gain me some level of knowledge, but it will likely come at a price: the person I’m asking may think I’m uninformed, unprepared, just plain stupid, or worse — that I’m deliberately causing problems.

So, is that price worth it? It depends on my goals.

If my goal is to impress others with my knowledge, then the answer is likely no, unless the person I’m asking is not a person I want to impress with my knowledge. If, for some reason, I’ve decided that I always want to impress everyone with my knowledge, then I can’t ask anyone a stupid question.

So, before I ask a stupid question, I have to decide that my goal is not to look impressively smart, informed, or prepared. This may cost me reputation and opportunity, even more so if I’m unable to turn those stupid questions into valuable insights and actions.

Instead, my goal must be to actually be smart, informed, and prepared. Regardless of the perceptions of others, I want to maximize the amount of knowledge I have, even at the cost of my reputation.

I think stupid questions can lead to this result because they are essentially engaging in First Principles: the act of reducing a problem to its basic components.

Here’s an idea. Each time I want to ask a Stupid Question, I can prompt myself with the question: will I benefit from understanding the underlying principles and assumptions? If yes, it may be worth it to ask the Stupid Question. I think this is tricky though, because I may not know the benefit of understanding these first principles until I know them.

I also wonder why basic questions are often considered stupid.

I wonder if the reason they’re considered stupid is that, in order to be productive, most of the time we have to operate with a certain level of assumption about these basic principles. So, most of the time, we proceed past the stupid questions. But, when someone has the time and energy to question the underlying assumptions, they can ask Stupid Questions.

Someone who has the time

There’s a guy I worked with who is great at asking stupid questions. I mean that as a compliment, but I won’t name him because who wants to be labeled as the guy who asks stupid questions?

Anyway, he’s fantastic at it. He’ll drop into a slack channel or a conversation and ask the simplest questions about how things work. Yet, somehow, they’ll turn into great conversations.

I think this happens for a few reasons:

  • Stupid questions seem simple

  • The simpler something is, the more likely people are to have an opinion about it

  • You can keep following them up with other simple questions, even a simple “why do you think that?” to keep the conversation going

I can imagine this person understands a lot more about the way things work than I do because he’s willing to ask the questions no one else is. It was also reflected in his title and position in the company, which was far higher than mine.

If you judged him by the questions he asks, as I’m sure some do, you might think he doesn’t understand anything. Yet, this person has far more impact than myself (and many others!), and I can’t help but wonder if it’s because he’s OK asking Stupid Questions.