On Asking Good Questions

It's putting it lightly to say the expression "there are no bad questions" is hackneyed. However, despite being a mascot who frequently holds the shield of “no bad questions,” I nevertheless don't think this is my desired end-game. I am interested in how to ask more engaging and perceptive questions. At a minimum, I'd like to ask fewer bad questions.

This curiosity began when I picked began pausing my runs to ask protesters about what's going on. I began stopping for nearly every expression of political speech. In my questioning, some of responses were to questions that lead no where interesting, while others let me learn about things that are simply otherwise unknowable. I began wanting to get into the experience of the person I was speaking with—to know Google can't tell me. And so it's been since fall of 2025 that I've become increasingly aware of this meta idea of question quality.

What sets the best and worst questions apart?

Bad Questions Exist

Okay, not in the global sense. Their badness is a feature of their context. For example, if you're asking a diplomat a simple question about the policy position of their country... what's the point of talking to diplomat?! But asking bad questions is easy and sometimes hard (at least for me) to even catch myself in advance before I launch myself into a question that isn't productive. I want to ask more good questions and fewer bad questions. On the flip side, sometimes the role of a question is more about connection than information. If you're chatting with someone at a café, asking about the day-to-day of being a materials scientist, in my experience, builds more rapport than Googling the answer on your phone.

When asking questions might be good

It gives people permission to ask the obvious thing and occasionally surface unexpected nuance. But the banner covers a wide range of question quality, and some questions are worth more than others.

Bad Questions

Bad questions tend to...

• Inquire about searchable facts
• Promote the likelihood of a canned response, often for being trite or politically charged:
  • Trite: Asking a protester something that focuses on their key points, keeping them away from critical thinking and reflection
  • Politically charged: Asking a politician about a politically sensitive topic (eg. asking a French Ambassador if they think a given politician is qualified)
• Ask about challenging or specific information which may cause the subject to clam up. If people feel like they’re on their back foot trying to save face, they won’t be good subjects.

Examples

• Can you explain that word again?
  • Bad in a classroom setting because there is an expectation of having done the reading and been able to research these things in advance.
  • Also MAYBE bad because can be searched individually later—is it essential info?
  • OKAY if in casual conversation.

However...

It’s all well and good to say that fact based questions are junk, but what about in a music theory class? Does that mean there are no longer good questions because these are just essentially facts for many of the introductory courses? What are good questions in a setting with objectivity, like math?

Good Questions

Good questions tend to...

• Be open ended
• Ask analytic questions that in some fundamental way depend on interpretation.

They are seeking to understand the world of the person who is being inquired about. Or it is trying to get at information which is not easily accessed otherwise. The information cannot be looked up. How Venezuelans feel about the future of their country is not a fact. Be cautious, however, that there are questions which have the superficial quality of being good while depending on an undesired question quality. For example, asking who should run Venezuela next depends on having fairly specific knowledge like:

Who could potentially run the country? Is the subject likely to be acquainted with several competing options? Or are they more likely to essentially know only one.

• This lack of knowledge can lead to soap boxing as the subject tries to compensate.

Good questions are open-ended and analytic—they depend on interpretation, not recall. They're seeking to understand the world of the person being asked. How Venezuelans feel about the future of their country is not a fact. It can't be looked up. The answer can only come from the person in front of you.

A related criterion: the question should be one the subject hasn't already answered a hundred times. Ask someone something new to them and they're forced to think. Ask them something familiar and you get their prepared version.

One caveat: questions that look open-ended can still fail if they require specific knowledge the subject doesn't have. Asking who should lead Venezuela next is only generative if the subject knows enough candidates to compare. Without that, the question invites soap-boxing rather than analysis.

Resources / Misc.

• Convergent
• Divergent
• Meta ? re: harvard, I think

Groups with domain-specific resources

• Journalism
• Survey methods
• Pedagogy journals for professors
• Therapy
• Podcasters (not into this, but I have so far seen a lot of 'startup hustle' interview style coaching)

Final Thoughts

I’m looking for… a way of thinking about making a meaningful contribution in seminar settings and contributing to the construction of a unique climate that we have not experienced before. The configuration of people in a room during a seminar, if that seminar is sufficiently intimate and being run in an almost dialogic manner, is a huge opportunity—it does not just need to be about moving information from one vessel to another.

Outside of school, I have a similar goal: I don’t want to ask a question the subject has already heard before. I want to ask something new. I want to provoke them thinking critically. It should be on a topic they know but not directly a question with which they’re overly familiar.