Illustration by OpenAI’s DALL·E 2.
Why asking the right questions matters in business, and how to do it.
Do you think the folks who ran Kodak in the 1970s were stupid? They certainly made one of the best-publicised mistakes in business history when they failed to capitalise on the digital camera that one of their researchers, Steve Sasson, had invented.
The new camera was too big and heavy, they argued, and besides, filmless photography wasn’t going to be the future of a company with a thriving photo film business that considered itself “the Bell Labs of chemistry”. Decades later, this decision and others like it would bring the once-proud firm to its knees.
This error in judgement contrasts sharply with Kodak’s other achievements at the time. The company grew tenfold between 1962 and 1981. Shares soared, and investors were richly rewarded. These were not the achievements of stupid people.
It’s a common story in the land of missed opportunities: intelligent, skilled executives nonetheless making what would in hindsight seem catastrophic errors in judgement. Yet it’s also a story repeated on a much smaller scale, every day.
“It’s a common story in the land of missed opportunities: intelligent, skilled executives nonetheless making what would in hindsight seem catastrophic errors in judgement.”
How do we make the next iteration of our product better than the last? How do we reduce unit costs and increase our return on investment? What are the right price points and how can we improve our go-to-market model? In which market should we launch first? Whom should we hire to optimise our supply chain? Should we make this acquisition? Are we chasing market share, profit, or growth?
Questions like these occupy most executives, most of the time, and they are rewarded for their ability to answer them. But that’s of little value if they are the wrong questions.
That’s what happened to Kodak. They solved the problems they thought needed solving, but had they asked “What will eventually replace camera film, as camera film once replaced photographic plates?” or “If we don’t sell digital cameras, who will?” they might have seized the future that laid in Sasson’s prototype.
Socrates and the art of questioning
How does one know the right questions to ask? There is no algorithm that will do this for you. A good question challenges assumptions, cuts to the heart of an issue, and depends utterly on context.
The good news is that it is possible to learn how to ask better questions, both as individuals and as a business, and by doing so build a culture of open-minded inquiry that will help you react and adapt at pace.
This is where Socrates comes in. You may wonder what a philosopher from Classical Greece has to do with 21st-century business, but there has been no better exponent of the art of questioning, or critical thinking.
The first victims of the Socratic method — still the favoured pedagogy across the Western world — are to be found in his disciple Plato’s early works, such as Apology, which detailed how Socrates met his untimely end.
“It is possible to learn how to ask better questions, both as individuals and as a business, and by doing so build a culture of open-minded inquiry that will help you react and adapt at pace.”
Proclaimed the wisest man in Greece by the Delphic Oracle, he sought to find people wiser than he, asking leading Athenian “experts” about their fields, only to discover after much probing that the poet couldn’t do something so simple as define poetry, or the general define courage.
His conclusion was that he was indeed the wisest man in Greece, because he alone knew that he knew nothing.
We can learn much from this.
Firstly, Socrates revealed that understanding comes from dialogue. He questioned relentlessly, zooming out to the big picture or zeroing in to the detail, asking “why, why” rather like a small child to their long-suffering parent, revealing assumptions and clarifying concepts until he got a satisfactory answer (or established the lack thereof).
Sometimes this critical thinking involved asking silly questions, or challenging views that were widely held or even sacrosanct. It may have seemed obvious to any self-respecting Athenian what poetry was, but that didn’t mean they actually knew the answer.
Socrates disdained not only conventional wisdom, but also the pretension to wisdom. Rhetoric was a particular target, because it represented the triumph of style over substance.
Today’s equivalent of orators preening in the agora is executives delivering slick PowerPoint presentations: each relies on the power of storytelling to convince. But do you want people to be convincing or to be right? They are often not the same thing.
“Today’s equivalent of orators preening in the agora is executives delivering slick PowerPoint presentations.”
Though it excels at exposing flaws or gaps in others’ understanding, it would be an error to see Socratic questioning as merely a way to take people down a peg or two — no matter how satisfying that may be in certain cases.
For a start, that understandably tends to rub people up the wrong way. Socrates paid for his gadfly-like provocations with a hemlock cup, but you might pay for it by poisoning your working relationships, which is hardly likely to benefit the business.
Equally importantly, Socrates approached his craft with humility — he knew nothing, remember — which is essential to deriving useful insights from questioning.
There is no point asking a good question if you’re not willing to listen to the answer, or if you’ve already made up your mind. You should approach it as a way to learn and strengthen your thinking, not to score points.
This is ultimately the objective of critical thinking for businesses — to learn and grow with collective intelligence, so that together you can adapt, spot opportunities, and avoid blunders like Kodak’s.
10 killer questions (almost) every leader should be asking
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“If we weren’t already in this business, would we enter it today? And if not, what are we going to do about it?”
~ Peter Drucker, the father of management thinking
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“Why does this lead to that?”
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“What would have to be true for the option on the table to be the best possible choice?”
~ Professor Roger Martin, Rotman Business School
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“What do the data not tell us?”
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“Why aren't football players urinating more?”
~ The curious question that launched electrolyte drink Gatorade
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“If we got kicked out and the board brought in a new CEO, what would [s]he do?”
~ Andy Grove, former CEO of Intel
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“Could there be another explanation?”
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“How can we become the company that would put us out of business?”
~ Danny Meyer, CEO of Union Square Hospitality Group
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“What if we’re wrong?”
- “Do we sell rolls of film, or preserved memories?”
Source: Inc., University of Florida
