Appreciating careful questions and distrusting easy answers

The author of Rethinking Thinking: Problem Solving from Sun Tzu to Google asks questions


What’s the smartest thing anyone can take away from philosophy? Perhaps it is that the questions are way more important than answers. This is essentially the message of Plato’s books written 2,000-odd years ago. (Don’t ask exactly which ones, exactly when, we don’t need to know!)

Plato describes Socrates wandering the streets of Athens looking for young men (sic) to ask questions which essentially had no answer. Puzzlers like “What is beauty” and “What is justice?” The point was to provoke debate and indeed I think some of the answers he found are interesting but that’s because they’re not like the official ones given in philosophy textbooks.

One response to the first question is that beauty is linked to celebrating life, which is why there is a sexual attraction to beautiful people, and an answer to the second is that justice is about ecological awareness, which is why Plato himself links it to everyone being vegetarian! You likely never heard it put that way before though.

Indeed, the reason we still talk about Plato’s book (and a small industry of tweedy academics make a living off it) is not the answers, but the method: the way in which Plato persuades us that we need to look at old questions afresh. This is the blue sky kind of thinking the Silicon Valley start-ups like Google and Apple have become global behemoths on.

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Apocryphally, when Google wants to evaluate people for employment, it puts aside their exam record – the evidence that they “knew conventional answers” to conventional questions – and instead interviews to see if they can “think outside the box”. They pose questions like “Why are manhole covers round?” with the aim, of course, not to be told some previously digested facts about manhole covers, but to see how someone thinks on their feet. In fact, there is a boring answer which mathematicians would know, which is that a circular cover cannot fall down the hole, whereas a square one, if turned to the diagonal, can do. Thing is, suppose some know-all applicant does offer this reason – what would that prove? That they happen to know about manhole covers? Or that they are good at interview question research?

No, the point is, we tend to respect answers too much. Many of us will have had the experience of searching online for information and being misled by answers, whether about how to mend some household item, or about what a medical symptom might signify (horror! we are going to die) or perhaps checking customer reviews for holidays, consumer products or whatever. Such opinions are like answers to very vaguely defined questions, not “wrong”, but off the point.

But here’s a bigger idea for you: don’t value precise questions, because to do that implies knowing the answer already. On the contrary, concentrate on making questions as open as possible. To see what I mean by this, let me introduce my two-part Mastermind quiz. Part one is a visual puzzle called the Nine Dots Problem.

This is really a classic exercise in “thinking outside the box”. Take a piece of paper and make a simple grid of nine dots. Then, try to connect all the dots by using just four straight lines (without lifting the pen from the paper or retracing). There are multiple solutions, but – spoiler alert! – they all involve extending the lines “outside the box”.

What, you think that’s too easy? Okay, well, now try to join the dots with just one straight line!* The problem illustrates how the answers we get can be completely refreshed by reframing the question originally asked.

Part of the quiz: who is the most influential philosopher of the 20th century? And the answer is… the Irish clergyman, Laurence Sterne. You’re unlikely to have got him as (a) he didn’t live in the 20th century and (b) he’s not a philosopher. But that’s what happens when you let the question drive you towards the wrong set of possible answers. You see, the conventional answer is Ludwig Wittgenstein. The eccentric Austrian is praised for two books, the first called obscurely the Tractatus Logicus Philosophicus, which is a mix of the views of his academic superviser at Cambridge, Bertrand Russell, and a rather nasty tract by one Otto Weininger called Sex and Character, a favourite text of – wait for it! – one Adolf Hitler.

But that’s politics. Sticking to philosophy, it is Wittgenstein’s other book, Philosophical Investigations, which is both rather better and more interesting to us. This, without doubt, was inspired by Laurence Sterne’s account of The Life and Opinions of Tristram Shandy, written in nine chunks with the first appearing as long ago as 1759. On the face of it, this is not a work of philosophy. Rather, it is an extended parody of the life of a humble pastor living in England.

Tristram woefully narrates key episodes, from the time as a toddler the sash window fell on his “manhood”, accidentally circumcising him, to his father’s neglect of his education on account of his determination to first design the system under which he was to be educated. One of the central jokes of the novel that Tristram cannot explain anything simply, but must make explanatory diversions to add context and colour to his tale, to the extent that it is well into Volume III before he even manages to mention his own birth. Anyway, Wittgenstein liked the book so much that he read it a dozen times! And if philosophers praise Wittgenstein for his “language games”, the first round, indeed the invention of the sport, clearly belongs to Sterne.

There’s a doodle in Wittgenstein’s book – of a duck that might be a rabbit, depending on what you are thinking as you look at it – and it is also borrowed, but still nicely illustrates my idea in this article. That the question you ask… shapes the answer you find.

*The trick now is, you have to think in three dimensions – roll the paper up!

Martin Cohen’s new book, Rethinking Thinking: Problem Solving from Sun Tzu to Google, is published by Imprint