The forgotten art of asking smarter questions

As any parent or carer of preschoolers can attest, by the time they reach the age of five, children have typically asked the question “Why?” a staggering 40,000 times. Yet it takes another 13 years for them to do the same again.

The Freudian psychoanalyst, Melanie Klein, described kids’ drive to understand as “the epistemophilic instinct”. It’s how they make sense of the world; how they can master uniquely human “if-and-then contingencies”, as Cambridge University autism expert, Professor Simon Baron-Cohen, describes them. “If I do this AND that THEN the other”.

Yet first school, then university (if we take that path), and finally the world of work do everything in their power to squish that thirst for knowledge out of us. We are validated and rewarded for the answers we give, not the questions we ask. Educational and workplace structures see asking questions as variously awkward, unhelpful, or evidence of “acting up”.

It’s time this changed.

Using data smarter

In our bigger and bigger data world, making smarter use of data to solve increasingly intractable challenges demands three crucial steps.

1. Asking smarter questions to surface the right data
2. Applying a little structure to ensure we can move from data to insight
3. Using the right data-driven insights to move others from insight to action

And yet, because of education and employment’s insistent focus on answers and not questions, the very institutions that should set us up for success are in fact doing precisely the opposite.

I was so concerned about this imbalance in the force that – a few years back – I determined to do something about it.

I started talking to people for whom professional success is predicated on their ability to ask smarter questions. Obvious candidates like researchers, analysts, and data scientists; doctors, lawyers, and teachers; coaches, the police, and conflict mediators. But also, less obvious contenders, including Zen Buddhists, FBI hostage negotiators, and sales trainers.

What soon emerged – even across such diverse professions, interrogating such very different data sets – was that there are some universal principles of Asking Smarter Questions. I detailed them in my 2023 book of the same name. They obtain whether we’re running qualitative interviews with subject matter experts, looking to extract entities from social media content, or using structured query logic to search and retrieve information from a database.

The six universal principles of asking smarter questions

1. Curiosity: not just for today’s brief or the drivers of performance in this quarter’s business review. But curiosity as a way of life, a modus operandi. A rekindling of Klein’s instinct.
2. Open Mindedness: at the intersection of openness to experience and intellectual humility sits the willingness to admit that we don’t know everything – particularly what a fresh and original line of enquiry might turn up.
3. Preparation: before you ask anyone anything, be sure to prepare – the structure of questions you want to ask and the flow you want to pursue with your line of enquiry. You need to be ready to follow where the answers take you. Prepare individual questions, and prepare the environment, real or virtual.
4. Openness: the quality of smarter questions identified most often by expert questioners is openness. Questions that yield better answers are open (not closed) by nature. Use the “Tell … Explain … Describe …” (or TED) formula that police use to get evidence from suspects, victims, and witnesses of crime. No-one does “Nice cop/nasty cop” anymore.
5. Simplicity: for questions, simple doesn’t mean simplistic or simpleminded, it means more straightforward to answer. Avoid cluster questions at all costs.
6. Listening: to hear the answers to the questions you’ve crafted and structured, you need to allow time and space. Learn to love the sound of silence.

A recipe for success

The four biggest enemies of asking smarter questions are our prejudices and biases – conscious and unconscious – our assumptions and prior knowledge. And the best way to overcome these are to adopt the approach taken by the Athenian philosopher, Socrates. He typically began his quest to understand the essential nature of any abstract quality – such as truth, beauty, or courage – with the paradoxical statement: “All that I know is that I know nothing”. The Socratic paradox is the very essence of Open Mindedness.

And not only should we embrace our inner Socrates to be sure we ask smarter questions. We should go back to kindergarten and embrace that enthusiastic miniature scientist we once were, that inner five-year-old, and start asking “Why? Why? Why?” all over again. In fact, why not adopt the methodology first formalised by Sakichi Toyoda, the Japanese industrialist and inventor who pioneered the Route Cause Analysis, aka “The Five ‘Why?’s”.

Sam Knowles is the Founder and Chief Data Storyteller at Insight Agents. He is also the host of Data Malarkey: the podcast about using data, smarter.

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