Questions Are Not Just For Asking

This is a guest post by Malcolm Ocean

Are questions just for asking? It kind of seems like it. I mean, if you consider the phrase “ask me a ______”, then the blank is obviously “question”. Just like how the blank in “that boggled my _____” is obviously “mind”.

But hang on a sec—boggling is indeed a thing that is only done to minds, but minds are capable of much more than just being boggled! Similarly, asking might be a special feature of questions, but questions are actually a versatile tool that can be used in many other ways.

In order to access those uses though, first you need to know how to comfortably hold a question without immediately asking it. Questions are a kind of creature that is easily startled.

(a panel from an excellent comic by Kostas Kiriakakis on collecting questions)

Effective asking of questions is an important skill. Being able to hold questions without asking them (when that makes sense) is a further skill, much as meta-systematicity builds on systematicity. In particular, operating in the fluid mode, seems to involve a certain kind of spaciousness that’s different than the space that a question holds for an answer. It’s a spaciousness into which you can start noticing your background assumptions and perceptual blindspots.

As Tiago Forte put it on Twitter, the ‘best solutions lie in category “didn’t know I didn’t know,” which means eliminating blind spots is more important than problem solving’. These solutions/answers are not ones that you can initially formulate the right problems/questions around, so you need to learn to listen.

Hazards of asking questions

The first of the twelve virtues of rationality is curiosity, which “seeks to annihilate itself; there is no curiosity that does not want an answer.” This may be, but desire comes in many forms, and a good curiosity isn’t hasty about this self-annihilation until it has truly fulfilled its purpose.

Curiosities that are overzealous are like interrogations, producing false confessions from the territory. That will get you answers, but it may not get you truth.

This often involves stopping when it’s easy. This can be the classic confirmation bias of someone who googles about something and stops with the first result that affirms their existing view. Or someone may swap in an easier question and answer that one instead, then use that as their answer to the first. Kahneman and Tversky documented lots of instances of this, for instance when people who know the high-crime city Detroit is in Michigan, but nonetheless estimate lower total crime rates for Michigan overall than for just “Detroit”, because they swap out “how many crimes occur each year in Michigan?” for “do I associate ‘Michigan’ with ‘crime’?”

But there’s a different form, which is questioning the territory (a person or situation) in a way that doesn’t give space for your actual curiosity to be resolved, instead yielding some sort of confusion or simplification that overshadows a still-existing unknown. For instance, someone asking “why do some things move themselves and others not?” may conclude something like “Animals have a life essence, or élan vital, that’s why!” This is a mysterious answer to the question: it feels satisfying but actually just buries the curiosity one level deeper: why do some things have élan vital, and others not?

Yet another form yields nothing satisfying at all, in which case the curiosity may retreat in frustration, only to come back even more aggressively in the future. This is common when someone has a legitimate thing they’re trying to understand (eg “why does it feel like nobody likes me?”) but then somewhere between their curiosity and the answer their question gets distorted (becoming perhaps “why does nobody like me?”) and they end up getting responses that miss the point fail to resolve the original unknown (eg “what? I totally like you, and so do other people”). In this example, the person might indeed be temporarily reassured on one level, but they haven’t actually gotten a deep understanding that can help them if the original question comes up again. So when it does, it can be even stronger for having felt ignored or misunderstood.

This is an oscillating tension, of the kind that Robert Fritz talks about and contrasts with creative tensions. “A basic principle found throughout human nature is this: Tension seeks resolution.” Effectively working with curiosity involves being able relax yourself while experiencing a tension of not-knowing, without insisting on immediate resolution. Some questions can be easily answered, but many will take time and non-obvious exploration.

This means letting the problem solve you, rather than you solving the problem; letting the question ask you, rather than you asking the question.

Hold your Questions

A question is a pointer into the space of unknowns. Recognizing this, you want to be able to work with the pointers themselves, not just immediately attempt to dive in their direction. Who is pointing, and why? What sort of thing you expecting to find? If you want a good solution, you need to be able to take a good look at the problem. The same is true for questions and answers, but many people can’t resist the urge to ask questions in the same way they can’t resist snacking from a bowl of peanuts next to them.

Being forced to immediately follow where questions are pointing (or forcing your conversational partners to do so) is a kind of being-subject-to relationship to the questions. Instead, you want to be able to take them as object, and hold them at arm’s length, and work with them consciously. (This is called a subject-object shift: you’re not subject to your questions—or other people’s—any more; they’re objects that you can hold and thereby manipulate.)

The foundational technique in this essay—a prerequisite to the others—is simply being able to hold questions without asking them. “Hold” has two meanings here, but it’s still essentially one thing. You want to hold off on asking your questions, put them on hold etc. Simultaneously, you need to be able to hold onto your questions, rather than just putting them aside altogether or dissociating from your curiosity.

Learning to put them aside can be a good first step though, if that’s currently a challenge. A few months ago, I started writing down all of my questions in a journal while in meetings, rather than breaking the flow to ask them, and I realized that many of them didn’t need to be asked:

• Some ended up being addressed several sentences or several minutes later
• Some I was able to resolve or un-ask on my own, once I’d written them down
• Some ended up not really mattering

Whether or not you are a frequent asker of questions, the practice of writing them down can be a good exercise in holding them without them having a hold of you. It’s kind of like a one-person version of dynamic facilitation, a form I’ll talk about further down.

A programming metaphor, for those inclined: holding your questions is kind of like how in functional programming languages or JavaScript, functions can be assigned to variables or passed into other functions, whereas in many other languages you can only refer to functions if you’re calling them at that moment.

Reveal your questions

Having gotten a comfortable hold on your question, the next thing you might do is quite simple, but it’s not easy. It’s challenging because it requires you to let go of expectations, and also because it requires understanding on the part of the people you’re talking with, that might go against their cultural defaults.

It goes like this: reveal your question.

Naïvely, we might assume in some sense that in the act of revealing a question, you have necessarily “asked” the question. But if we dig deeper, this is not the case!

One trivial example: say Alice has a question for Bob, and she tells Carol about her question, knowing already that Carol isn’t able to answer. Alice hasn’t asked Carol the question, she’s just revealed it to her.

By “ask”, we essentially mean putting out a question with the expectation of an answer. This expectation could be an entitlement or an anticipation, or both. (An example of the case of someone feeling an entitlement but not an anticipation of an answer would be when someone angrily asks their computer “Why aren’t you working?!”)

If you have some kind of expectation, it can be disorienting if the askee doesn’t respond in the way you expect. In the entitlement case this is obviously frustrating, but even in the anticipation case it can sort of cause you to go “huh?” You might be satisfied, though, if the person responds by saying “I don’t know” or “I’m not allowed to answer that.” These aren’t answers on the content-level, but they take the place of an answer—sort of a null answer.

But the act of revealing a question doesn’t inherently engage such an expectation. It merely creates common knowledge that the question is present for you. This may result in an answer immediately, or an answer at some later point, or it may have much more subtle effects.

Some phrases for doing this:

• “I guess the question, then, is…”
• “I notice I’m curious about…”
• “One question that’s coming up for me is…”
• “I’ll just put out a question I have, which we don’t have to try to answer just yet…”
• “I’m not expecting that you have an answer to this per se, but something I’m trying to figure out is…”

Having revealed the question, you might get an answer, or you might get a better question, or you might even get a response like “exactly!” to an open-ended question. That response isn’t answering the question; it’s agreeing with the question’s relevance or importance. This sometimes happens even when the question has in a sense been “asked”, but the person is nonetheless responding to the revealing component that was present in the asking, not the expectation.

When it works well, revealing a question essentially functions such that you and others are now holding the question together. But if the other person isn’t comfortable with revealing or holding questions, their cultural assumptions can get in the way…

Un-ask your questions

I was on the phone with my dad last month, and as parents do, he asked me a relatively specific and personal question. I said something to the effect of “I don’t think it really makes sense for me to try to answer your question as stated, because I’m not sure what the answer would mean to you, and so I want to establish more context first.” Defying centuries of intergenerational suspicion, my dad said, “Okay, cool, well, I take back my question. I mean you can’t, you know, really take back—”

I interrupted: “You can totally take back a question!”

But my dad’s belief, that you can’t, is a common one, and it stems from the same confusion that this essay is addressing — that questions are only for asking. After all, where is a question if it’s been revealed but not asked? Unless the question is being held (as above), the only way this is possible is for the question to be rejected or negated altogether.

The latter sense is present in the term mu, as used by Robert Pirsig in Zen and the Art of Motorcycle Maintenance and by Douglas Hofstadter in Gödel, Escher, Bach. Responding to a question with mu means rejecting it altogether. It’s a good tool to have in your arsenal is good for loaded questions (“Do you still wear diapers on your head while you sleep?”) but mu doesn’t work so well for situations where you want the question to temporarily become held rather than asked, because it can to sort of destroy the question in the process.

This, I think, occurs because of that assumption that questions are only for asking, so the only way to unask the question is to reject its validity as a question altogether, in which case it never really could have been asked in the first place.

As the asker, all you need to take back a question is to say “I hereby take back that question, at least for now”. Well, that, and you need conversational partners willing to accept that such a speech act is even possible. Maybe send them this essay if they protest.

Of course, taking back a question doesn’t result in a world state in which you never asked the question in the first place. You’re not rewriting history and you can’t un-reveal the question—the information has been released. Although of course people who confuse revealing a question with asking a question may use the common phrase “forget I asked”. That’s asking to decide together to rewrite history. But that’s rarely necessary when you can just hold the question together instead.

It requires trust to do this. I could imagine in many contexts my response of not wanting to immediately or directly answer my dad’s question being viewed with suspicion. Was I trying to hide something? To mitigate that sense, I explicitly stated during that conversation that I really wanted to have the scaffold present to be able to talk directly about these things. Of course, it takes a certain level of trust for someone to be able to hear that, too.

Question your questions

Whether in conversation with others, or alone, sometimes you have a big hairy question that you don’t know how to start on. One on my mind at the moment is, “How long will it be until we have human level artificial intelligence?” You may not know how to start answering the question, but you can potentially identify bits of information that you could have that would help you answer the question, and one way you can do that is in the form of questions. Ideally of course, you come up with new questions that are easier to answer—or even simply look-up-able—but if you come up with a related question that’s just as hard (or even harder) then write it down anyway. Maybe you can break that one down too!

Breaking down a question can help you get clear on which components to actually be investigating in a given situation. These components might have a specific relationship, such as in Fermi estimates where you guess at a number by multiplying subguesses together, or they might just paint a better picture of the landscape you’re trying to understand.

Here’s a very-incomplete example of a breakdown of “How long will it be until we have human level artificial intelligence?” that I just typed out:

• Within computation, do we expect greater gains to come from hardware or software?
  • How close are we to physical limits of hardware? (given current paradigms)
  • What are the main challenges remaining to be solved in software?
    • What have people written about this?
• What can I learn from experts?
  • What do the experts say?
  • How well have people been able to predict things like this in the past?
    • What related things have people tried to predict?
    • When they’ve been off, what sorts of mistakes have they made?
  • Are certain experts more trustable than others?
• What are some of the (earliest/latest) tasks I expect AI to surpass humans at?
  • What dates do I expect for those?

Nowhere in this process have I actually asked the question. I did something which first yields more questions, rather than answers.

Scott Aaronson claims that this is in fact what has happened “whenever it’s been possible to make definite progress on ancient philosophical problems:”

…one replaces an unanswerable philosophical riddle Q by a “merely” scientific or mathematical question Q′, which captures part of what people have wanted to know when they’ve asked Q. Then, with luck, one solves Q′.

…A good replacement question Q′ should satisfy two properties: (a) Q′ should capture some aspect of the original question Q — so that an answer to Q′ would be hard to ignore in any subsequent discussion of Q, [and] (b) Q′ should be precise enough that one can see what it would mean to make progress on Q′: what experiments one would need to do, what theorems one would need to prove, etc.”

This last heuristic is a good one. If it’s not clear what tests you could do now that might change your answer to “How long will it be until machines/AI can perform as well as humans on most tasks?” then your model (if you even have one) is missing something. If you try to answer such a question directly, then you’ll end up with a particular year or range of years that seems about right… but you’ll get better results if you first break down the question into things you can think about more precisely.

Of course, make sure that when you do answer Q’, don’t mistake your answer for a full answer to the original question Q, however.

In more pragmatic contexts, such as, “What’s our top priority for user growth over the next month?” there is more urgency towards ending up with an actual working answer rather than just spending the whole time philosophizing or strategizing. In particular, the team asking that question is ultimately going to spend their next month doing something, whether that something is strategic or not.

Knowing this, there’s a balance to strike between heading towards the best known answer to the best known question, and re-understanding the question itself so as to gain a better navigating tool to work with. This results in not just better answers, but even if the answer is in some sense the same, the question is the context for the answer, so it shapes everything about your experience and interpretation of the answer. The answer exists in relation to the question.

Using Questions to Organize Attention

Because answers exist in relation to questions, sometimes you can’t even notice the answers you need unless you’re already holding the right questions. The mathematician Gian-Carlo Rota wrote:

“Richard Feynman was fond of giving the following advice on how to be a genius. You have to keep a dozen of your favorite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or read a new trick or a new result, test it against each of your twelve problems to see whether it helps. Every once in a while there will be a hit, and people will say: ‘How did he do it? He must be a genius!'”

I recently generated such a list myself, as one of the exercises in Tiago’s Building a Second Brain course. I promptly found myself wanting to share these questions as an opening to many of the conversations that I was having. These are big complex questions though, not things that it makes sense to ask everyone I talk to. They won’t in general have answers, and even if they do have answers, they may not actually understand the nuance of the question I’m asking. But holding these questions can still help me notice when answers appear in front of me.

People sometimes do this in an ad hoc fashion. For instance, at the start of an event, whether a corporate conference, a workshop, or even a vacation, people sometimes consider a few questions that are top of mind that they’re hoping they might get a better understanding of. They might also share these questions with other people at the start of the event, not primarily so those other people will answer them, but because having the questions held collectively can facilitate attention being paid to those questions by others as well:

“Oh, Sam, you’re doing research into coordination strategies between organizations? You need to talk to Alex, he’s got some questions about that.”

When you ask a question, it represents a thing you care about knowing. In goal-setting literature, it’s well-established that goals “direct attention and effort towards goal-relevant activities and away from goal-irrelevant activities.” So we would expect that there is an attention-directing function to asking questions as well, which can potentially be harnessed without actually asking them and focusing on an immediate answer.

First of all, sharing a question that you have, or articulating it to yourself, helps to direct your own attention towards the hole-in-understanding that that question represents. So it’ll cause you to potentially be more aware of information that could help you answer the question, and it may also give you more affordances for actually *asking the question* of someone at a moment when that makes sense. It may also cause the person you share the question with to share different information later, not necessarily as a direct answer to your question but because they have a better understanding of what you’re interested in.

This practice is formalized and expanded by a conversation structure called Dynamic Facilitation, in which participants articulate whatever comes to their mind, and a facilitator writes down what people say on some boards that all can read, under four categories: problems/questions, solutions/options, concerns, and data. What is relatively unique about Dynamic Facilitation is that there’s no expectation that each speaker will necessarily respond to the previous speaker(s). Answers may emerge to questions that were asked, but this happens in an organic way, allowing relevancies to be pieced together as the conversation flows, rather than requiring an immediate answer so that the question can be ticked off the list.

Where you direct your attention is extremely important, because it affects so much else. The kinds of things that your attention is drawn to become downhill for you, meaning that you will naturally orient towards them. If you can change where your attention is drawn, that can ultimately change your thinking and your behaviour.

And questions are a tool you can use for that, as long as you’re able to hold them without immediately asking them (which shifts your focus onto answers). Leave the question in your mind as a thing to be figured out by your mind’s further interactions with the world.

Letting the question ask you; becoming the answer

In fact, sometimes leaving the question in your mind is literally the answer to the question itself.

This is part of what I meant earlier when I gestured at shifting from asking questions to letting questions ask you.

This represents kind of coming full circle from where we started. I described earlier that the core skill of holding questions means shifting from being subject to the question-as-asked to being able to take it as object. Letting the question ask you is a conscious subject-object shift in the opposite direction, but this time you’re taking on the question at a different level. Rather than trying to answer the question within its original frame, with whatever assumptions you’re bringing into the situation, you’re positioning yourself—including your sense of self—within the question in a way that allows you to embody an answer that you couldn’t possibly have articulated.

This is at the core of any question about how to change your way-of-being.

I do productivity coaching for people—informally for friends and professionally for clients. There are a lot of tips I can give people, such as “try the pomodoro technique” or “put your phone on airplane mode when you’re trying to focus”. These tips will work somewhat! But the only complete answer to many of the fundamental questions people have about motivation, productivity, effectiveness etc…

…is “do not let go of the question.”

As the comic in the opening gestures at, questions are always in heat to mate with answers. And this self-referential response—that the answer to your question is the question itself—doesn’t feel like a satisfying answer in the way that “try the pomodoro technique” does. Certainly, it’s not an answer that the question can mate with, to the point of self-destruction.

“How do I stay focused on what’s important?”

There are plenty of object-level answers to this question…

• meditate regularly
• journal every night
• focus on your three Most Important Tasks every day
• only say “yes” when it’s “hell yes”, otherwise say “no”

…but unless you keep that question in mind—how do I stay focused on what’s important?—these strategies can gradually drift away from being your best known answer to the question. Perhaps because you stop actually meditating. Perhaps because your journalling starts being about random events in your day, rather than reorienting towards what’s important to you. Perhaps because your three MITs tend to point towards a short-term project that doesn’t matter in the big picture.

These systems can be valuable. But ultimately only to the extent that they continue being answers to the original question. Thus the complete answer to the question is to do whatever you need to do, or become whatever you need to become, in order to continue enacting an answer to the question, in the shifting landscape of your evolving self and your changing environment.

To quote a poem by Rumi: don’t go back to sleep!

The examples around productivity are of medium complexity. The most basic example of this kind of situation (so basic it could be misleading, which is why I didn’t start with it) might be learning a physical skill. The Inner Game of Tennis (video) describes how having conceptions in your head of what you’re supposed to be doing tends to get in the way of your actual performance—even for a beginner who doesn’t really know what they’re doing. These concepts are the “answers” in this scenario. At the end of the video, the speaker mentions that it could help you “saw boards better”, which reminded me of the last time I sawed a board. It was going a bit roughly, with the saw catching a bit on the wood. I don’t really know much about sawing technique, but I realized there was a subtle way in which I was sawing as if I did. I kept sawing, but shifted my focus to getting curious about “what would make it go smoother?” …moments later, it was smoother. Now, I have some vague ideas about what changes I made, but on the most fundamental level, what I did was I held a question in my head and let my motor control systems reorganize themselves to embody the answer.

On the other end of the complexity spectrum are questions where the reorganizing needed isn’t in physical systems but in much more abstract layers of one’s mental perceptual hierarchy. I was recently working with another question about how to make something go smoother, but in this case it was, “How could I be paying attention differently in order to create smoother and more comfortable interpersonal interactions?” As I revealed the question to a friend, I realized that if I just didn’t let go of that question, then that act itself, of genuinely continuing to hold the question as I interacted, might mean that I would be paying attention in that different way.

Part of me feels like I’ve tricked myself and that can’t possibly be it.

But it is. Or at least, it’s a solution, and a meaningful one, not a trivial one.

What’s happening is that by continually orienting to the question “what sort of attention do I need to be paying in order to create an experience of trust and flow in my relationships?” my attention is naturally being drawn to whatever factors seem to generate that kind of experience—or what factors might be getting in the way. And this, by definition, is a way of paying attention that will tend to yield increased trust and flow, and therefore is a sort of answer to the question. But the answer isn’t in the words, but in the actual ongoing asking of the question in the wordless space of my perceptions.

The kinds of questions for which this is true are questions that gesture at some reorganization of your perceptual hierarchy, where you can’t yet articulate the answer because your ontology lacks the necessary concepts. Or any question where words can point at an answer but can’t actually be an answer. At the most philosophical end of this are koans, or statements like “The Tao that can be spoken is not the eternal Tao”

Norbert Weiner said “The best material model of a cat is another, or preferably the same, cat.” Sometimes the best answer to a question is another question, or even the same question. You just need to know how to use it. Or rather, how not to use it.