Types of Questions (Part 1)

• January 24, 2026
• thoughts  
• notes  
• questions  
• curiosity  

I think the way we teach kids to think about and categorize questions is completely wrong. If I think back to any time I’ve been taught about questions formally, I’ve always been taught to think about the 5 W’s: Who, What, Where, When, Why – and the H: How?¹ These are perfectly good questions to focus on if you’re a journalist writing a news story, but most of us are not journalists, and I’ve found a broader range of questions to be useful or relevant in my day-to-day life.²

The types of questions I find I regularly use mostly fall into six categories:

1. questions for establishing facts or definitions
2. process-related questions
3. clarification questions
4. comparative questions
5. questions for generating interpretations
6. speculative questions

1. Questions for establishing facts or definitions

This is the most basic type of question that I ask: baseline “let’s get on the same page” questions. Who, What, Where, and When questions all fall into this category.

These are questions like:

• What does this acronym mean?
• Am I speaking to [insert name here]?
• What are we talking about?
• Where are we going?
• What is X?
• Who is X?
• What does [insert word here] mean?

These questions are very important because it’s hard to make any sort of meaningful contribution if you don’t know what is happening. If you don’t know what people are doing, you can’t help them. You can’t participate in a conversation if you don’t know what it’s about. If you don’t know who the person talking to you is, you’ll likely be unsure of how to interact with them. Navigating life tends to depend on having the right context, and everything is built on top of answers to these questions.

I also think these are some of the questions that people are the most reluctant to ask, because they are afraid of appearing stupid or admitting that they don’t know things.

Actually, sometimes I don’t even phrase these as a question, just as an admission that I don’t know something, especially if it’s a casual setting. If a friend starts talking to me about some public figure, and I don’t know who they’re talking about, I might just stop them and say something like “sorry, I have no idea who [insert person’s name] is” and simply expect them to explain. You know, once they’ve finished teasing me for being clueless.

I am clueless about many things and not afraid to admit it. I unironically think that’s gotten me pretty far in life.

2. Process-related questions

These are “How?” type questions, for the most part. They are very straightforward and typically involve understanding some kind of procedure (or solving some kind of problem).

Examples include questions like:

• How do I install this software on my computer?
• Can you explain how I’m supposed to solve this matrix again?
• What is the recipe for this?

The vast majority of tutorials live in this space. They often don’t actually give any reasoning for why anything is being done, which is annoying for a person like me who likes to know the “why” behind everything, but they do tell you what to do, which is certainly useful.

3. Clarification questions

Clarification questions are for when you don’t fully understand something that has just been said, and you want the person you’re asking to do some extra work or thinking to convey their meaning to you.

Here are three of my favourite such questions:

• Can you back up a little bit?
• Can you elaborate?
• What do you mean when you say “[insert word or concept here]”?

Fact-establishing questions can also function as clarification questions, by the way, but they’re really only useful when you can pinpoint something specific to clarify, whereas the questions in this section are more for when what you’re trying to understand is fuzzy. For example, if I’m asking you to elaborate, it means I think I am missing some information. However, I might not actually know what that information is, so I’m going to listen to you and hope that by saying more things you will stumble upon the information I’m missing.

I particularly think “can you back up a little bit?” is a super underrated question. Usually I will tell the person where to back up to (the point at which they lost me), and ask them to re-explain from that point onwards. I like this question because it allows me to signal that I think the person might be assuming some kind of background knowledge or context that I don’t have, and that I would like the person to give me that context before they continue with the rest of their explanation.

I also find that I use these questions more often in conversations that are happening at a somewhat conceptual level. I’m usually trying to go a bit beneath the surface of the thing I’m trying to understand.

4. Comparison questions

Again, we’re somewhat more in the conceptual mode here. These are questions of the form “Is X like Y?” or “Is X at all related to Y?” or “Is doing X similar to this aspect of doing Y”?

These questions are for trying to draw connections between things. I find that I ask these questions a lot when I’m trying to understand something, because I’d like to know if any of my existing mental models can be adapted to work in the new context.

Asking questions like this is almost like thinking about things in terms of analogies or metaphors, just a little bit more concrete. When Shakespeare writes that Juliet is the sun, he’s mapping some attributes of the sun to Juliet and hoping that the reader can use that to better understand how Romeo feels about her. But asking a comparison question would be like if Romeo was trying to explain how he feels about Juliet, and a confused person asked if looking at her felt like looking at the sun. Then Romeo would have to think about it for a second, try to make the connection in his brain, and then say whether or not he thought the connection made sense.³

Another example⁴ would be if someone was trying to explain some kind of math concept and a student drew an analogy to programming. The person explaining could, if they had a background in both math and programming, think about both and decide whether or not transferring over the thought process makes any kind of sense.

For example, you could think of set builder notation in math as being similar to some kind of if statement in programming. The set $S = {x \in \mathbb{Z} : x \in [1, 10] and 2 | x^2 }$ could be created using the following code:

Is it a one-to-one mapping? No, absolutely not. The predicates in set builder notation do not actually function like if statements. But is it a useful way of thinking about them? Possibly, up to a point.

5. Questions for generating interpretations

These are “Why?” questions for the most part, although “What does this really mean?” and “How did we get here?” also qualify sometimes.

These questions are about going deep and getting to the bottom of something. A lot of the time, when you ask people for information, they only give you surface-level information, without any context or further explanation. While that information is better than nothing, it’s usually not enough when you’re trying to figure out what the root cause of a problem is or come up with a solution to a big problem. To get the right amount of context, you often have to start asking more involved questions that will help you mentally construct a bigger picture of what is going on.

I live in this mode most of the time, I think. I am happiest when chasing the answers to these sorts of questions. Unfortunately, these can also be really uncomfortable and/or dangerous questions to ask, because you can accidentally stumble into sensitive territory or offend someone.

6. Speculative questions

These are “What-if?” type questions - the kind of questions so-called “creative people” are known for.

Personally, I think it’s easiest to start asking speculative questions once you’ve already gathered information from all of the other types of questions. This is because knowing what has been done before and knowing the current state of things enables you to then start to imagine how things might be different or improved. Otherwise, you risk coming up with ideas that are interesting, yet completely irrelevant.

Of course, this is not an exhaustive guide to questions: they’re just the questions I find most relevant, and how I choose to think about questions. After I wrote this, though, I was also curious to see how other people think about questions. I will write about these in a future part two to this post, assuming I don’t forget.