You Need to Ask More Questions

• November 17, 2025
• advice  
• thoughts  
• questions  
• curiosity  

Have you ever considered how people who are more knowledgeable about something than you got that way?

A lot of them got there by asking the right questions.

The reality is that most people are not going to bother to explain themselves to you if you don’t bother to come to them with questions. Some people don’t realize that you don’t know the things they know. Or worse, they may have absorbed certain things via osmosis and be trying to convince you to do the same. The problem is that without asking questions, you might not even realize what it is that they’re trying to teach you, or that they’re trying to teach you something at all. The reverse can also be true: you might be trying to learn something from someone, but if you never ask any questions, they might not even notice your interest. If you are confused but never ask for clarification, people will generally assume that you understand what is going on. Alas, we cannot read each other’s minds.

Asking questions no one else is willing to ask is also how you get context that no one else has. I strongly suspect that I have a lot more knowledge about the various organizations I’ve been involved with than the average person at my level of experience/responsibility. This is because I’m not afraid of asking above-my-pay-grade questions like “why are we doing this?” or “why do things work this way around here?” or “how does the culture here influence the decisions we make?” or “why is it that our leaders all have this narrow perspective?” You might not always get real answers to these questions, but if you ask enough people, you should eventually find someone who is willing to give you a coherent explanation. Barring that, you should, at the very least, eventually have enough bits and pieces of information to string together a reasonable theory of your own.

You can ask questions of sources other than people, by the way. Actually, one of the best ways I’ve found for understanding texts and retaining information from them is to ask myself questions about the things I’m curious about or confused by and scrawl them in the margins as I read. Asking questions turns learning from a passive process (one that is inflicted upon you) into an active process (a.k.a. one that is owned and initiated by you). What do you remember better? Things you want to know? Or things you’re being forced to know?

This is also why I ask questions during lectures.

But I don’t have any questions!

Listen, curiosity (and having the willingness to ask questions) is a muscle. If you never use it, it never develops. If you don’t use it for long enough, it starts to atrophy. Having a question is really just identifying something that isn’t clear to you or that you don’t understand and seeking to fill that gap in your knowledge. If you do it enough, it becomes a reflex.

Is this reflex annoying to some people? Sure, if you go overboard. But living your life in such a way that you’re actively avoiding causing any annoyance to people is unlikely to help you achieve anything of value.

Also, are you sure you don’t have any questions, or are you just scared to expose that you don’t know everything? I’m sure you have real questions like “what does this acronym mean” that you’re too afraid to ask.

You should still ask those questions.

But all of my questions are stupid/basic/wrong/[insert demeaning adjective here]!

You know what group of people I’ve found to ask a lot of basic and stupid questions? Experts. Professors, senior technical staff, leadership, etc. all ask more questions in meetings/seminars/presentations on average than the non-senior people in the room. They don’t feel like they need to prove that they know things, so they’re not afraid to be public about not knowing something. This typically translates into them knowing more things over the long run, because the basics are the foundation on which all other knowledge is built. Wild, I know.

I understand that asking basic questions in public may be nerve-racking. The other day I asked a professor what he meant by “building the source code” when he was talking about the software testing process and he made fun of me for asking such a stupid question in a third-year course. (He also knows that I’m actually a fourth-year, which makes it even more embarrassing .) I’m sure half of the class thinks I’m stupid now, but I really needed him to clarify what he meant because I don’t think he realized that he was using the term somewhat ambiguously, and without asking such a “basic question” I never would have gotten to the bottom of why I was confused. If you think I’m stupid because I’m trying to get on the same page as you, that’s a you problem.

I think not being afraid to ask basic questions is especially important when you’re an intern. You can get away with not asking questions at school, because school is at the very least supposed to teach you things. (Whether or not it succeeds at that goal is another story.) However, corporate environments are different because the goal is to get stuff done ¹. You know what slows down getting stuff done? Endlessly explaining things to people. Or, in other words, everyone behaves like everyone else already knows what they are talking about.

The average intern is silent and never says anything during team meetings. Do not be this intern – not only do you not learn anything this way and get nothing out of the meetings, it is also bad for visibility. First of all, people who ask questions are more memorable because it’s hard to forget you exist when you actually participate in meetings. This is good, because no one will offer you opportunities if they don’t remember that you exist. Secondly, the knowledge you gain from asking those questions will help you make the most of whatever opportunities you do get, because you’ll actually have enough context to contribute meaningfully.

But I don’t know who to ask!

I get it, figuring out who has the right answers can be tough, and that is a skill in and of itself. However, have you considered starting with asking the people around you? It’s actually surprisingly helpful. Even if they don’t know the answer to your question (and sometimes they do!), they can usually point you to someone who has a better answer to the question, or possibly even offer you a different way to think about things that might invalidate or clarify your question.

And of course, as you get more accustomed to asking questions, you also gain a better sense of who you should ask (or where you should look, I guess). Like, you can also look for information in books, on forums, through querying search engines…

Right, and I guess there are also AI tools. Those are a whole can of worms on their own.

Why bother asking questions when I have ChatGPT?

Having ChatGPT means you should be asking more questions than ever. LLM chatbot interfaces are fast, convenient, and able to remix information for you in a gazillion different ways. However, they’re not particularly known for being trustworthy, consistent, accurate, or deep. This means that you will probably need to scrutinize information you get from an LLM much more than you would information from a traditional source. Not to mention, all of the different LLMs have their own quirks and may behave in wildly different ways! I have a few colleagues who will ask the same question to four (or more) different LLMs just to see what each of them answer and how they differ.

In my opinion, you should probably also avoid the temptation to offload your critical thinking skills to a piece of software, but you do you, I guess. I think my point stands.