(the following vomit is likely going to be extremely sketchy and incoherent)

How do you ask good questions?

I think the fun geeky thing to do would be to ask if “how do you ask good questions” is itself a good question. And… I think the answer is… it’s an okay question, but there are probably better ways of framing it. Let’s riff on it for a bit. One might be “where do good questions come from?”, or “how do you identify a good question among a list of ‘okay’ questions?” “What separates a good question from an average one?”

A good question is energizing. It’s an inviting challenge, it’s something that’s interesting and fun to pursue. It inspires a new way of seeing things, a new way of ordering information.

Is a question always a request for information…? I think so. And sometimes the information is just sitting there somewhere.

Frequently Asked Questions are typically the most boring, because the answers tend to become “stock”.

Sometimes a question is a request for a specific bit of information, but getting to that bit is an interesting journey.

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It’s possible for an interesting person to take a boring question and look for what’s interesting within it. I find myself thinking that Neil Tyson is pretty good at this when people ask him questions relevant to his domain. I remember once watching a video of Katy Perry talking with Neil Tyson – and lots of people were being mean in the comments, calling Katy stupid and so on, which I found very unproductive. The fact is that she was making an effort to try and learn more about things. And Neil was willing to take her questions, however simplistic or amateurish they might’ve been, and he found a way to decipher them, to look for what was interesting within each question, and then direct the conversation to that instead.

I find myself thinking also about Joe Rogan’s conversation with Elon Musk, which seems like a bit of a contrast. My sense was that Joe was trying his best to be engaged and to ask Elon interesting things (or what he thought was interesting), but Elon seemed particularly tired and listless, often going into his own head – and so the conversation has this slightly painful, awkward quality – like someone talking to someone who isn’t quite entirely there.

Taking these two things together and considering them, I find myself thinking… a good question is a sort of team effort. It requires buildup, it requires evaluation, re-evaluation, consensus…

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A good question is an act of pointing. First you survey the ideascape in front of you – maybe it’s shared territory between the two of you, or maybe it’s you looking over your conversation-partner’s shoulder – and then you try and identify the most compelling, interesting thing, and point to that. And you investigate. Why is that there? How did that get there? Does it serve a function? Why that and not other things? What if it were bigger? What if it were smaller? What if things were some other way?

Sometimes when someone asks you a question, they’re pointing in a general vicinity, but not actually at The Most Interesting Thing, because maybe they haven’t yet developed the vocabulary or incisiveness or familiarity with the territory to realize what exactly they should be asking – and you can do both them and yourself a favor by redirecting them to the More Interesting Thing. But doing this also requires understanding where they’re coming from, what they’re after. It requires that you have a model of their mind…

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I remember Paul Graham had an essay about essays, and his directive for writing interesting essays was “flow interesting”. That sounds circular, so I’m probably missing something – I’m going to look it up now. OK. He starts out by talking about how so many essays are boring and pointless – he suggests that it has to do with a sort of accident of history, where students are imitating english professors, who in turn are imitating classical scholars, who were doing work that was exciting 700 years ago, but isn’t quite so relevant anymore.

PG has two questions for people reading his essays – “which bits are boring, and which bits are unconvincing?” The boring bits can be cut away, but the unconvincing bits need to be re-examined, reconsidered. The essay must’ve been written because he thought something was interesting or needed explaining, and if it’s unconvincing, it must be because the explanation was unclear, or wrong. (And not “not clever enough” – trying to be convincing by being “clever” can be a form of intimidation).

To PG, “interestingness” is a function of surprise. Interfaces should follow the principle of least astonishment – things should do what they look like they do. Essays should do the opposite – they should optimize for maximum surprise. Surprises are not just things you didn’t know, but things that contradict what you thought you knew. How do you find that? He has a few suggestions: keep track of your observations, collect your surprises, pay attention to things that are funny, read history, be a little disobedient and naughty. I completely agree with all of these as good things.

David Ogilvy: the best ideas come as jokes, make your thinking as funny as possible

Chris Rock: when trying to write comedy, don’t bother trying to be funny. Just be a reporter, look for what’s sticking out, and then look for the question that hasn’t been asked

I feel like all of these things are still… kind of… a layer of abstraction away? I think the Ogilvy + Rock quotes are a good place to start, and they’re resonant with the PG essay. There are seemingly two ways to navigate – take a random walk, or maybe a system of walks (see @joulee’s diagrams), and see what’s funny or surprising.

I think about these two pictures from @joulee a lot – very succinct and powerful way of describing how professional creatives have a more structured process, and how that isn't necessarily limiting – you actually get to try more things this way pic.twitter.com/XUA8zUZBMb

— visakan veerasamy (@visakanv) May 21, 2018

What’s implied in Chris Rock’s quote is revealing – in order to ask a question that nobody’s asked before, you have to know what are all the questions everyone’s asked before! That’s a lot of work, but you can go through it quickly. You have to do the reading. You have to do the pattern matching. I don’t think there’s much of a way around it. The thing is, the “funny” or “interesting” is a sort of compass or gyroscope that guides you away from stale questions…

This incidentally is how I think about branding, too. I came up with my book idea for Naughty Boy by looking at a list of Singaporean novels and thinking, what’s the most radically different thing I could come up with? What’s the Party Cannon of novel covers?

Anyway. I gotta think about this more still.