Food for Thought

"Judge a Man by His Questions"


We're never taught how to ask questions, yet they are critical to how we think, what we learn, and who we connect with. When time is short (like at breakfast), when attention spans are even shorter (as with twenty-first century man), and when the need for answers is urgent (read the news), a shoddy question is at best wasteful and at worst catastrophic.  

"Judge a man by his questions rather than his answers" - Voltaire

So how do you fine tune your questioning? What's the magic strategy?

What is clear from all that we have read is that you can't ask a good question if you're not curious; and curiosity can't be faked - it has to be authentic.

But curiosity alone doesn't guarantee a superb question, still less a supreme answer.

Questions can be paralysing, flattening, alienating, irritating.  They can seem carping or critical.  They may divert you down the wrong warren.  

Fortunately, there are mental maps and models to help you out.  Below we have set out the best advice we have read for three different scenarios from three different disciplines that all hinge on asking great questions (journalism, business innovation and coaching).

1. WHEN YOU WANT TO... gather information

The editor John Brady (author of the seminal guide to The Craft of Interviewing) argues that to get people to reveal information you need to build a sense of "kinship".

Why kinship? Because from that flows trust, and from trust flows frankness (and from frankness flows headlines). 

And how is kinship created? In every way that people communicate, whether verbal (terminology, phraseology, formality) or nonverbal (dress, body language, eye contact). Above all, Brady recommends imagining yourself in the respondent's shoes and trying to feel what he or she is feeling, rather like an actor applying the Stanislavski method. The empathy is always sensed. 

Other authorities are equally emphatic about the need to suppress your ego and - paradoxically - stop thinking about what you are going to ask or say next, so that you can truly listen.

Additional advice for encouraging people to open up includes keeping questions as short and light as possible, and avoiding judgement - or distancing it, by ascribing it to others ("some people say that you're not very pleasant first thing in the morning...").

“You know what charm is: a way of getting the answer ‘yes’ without having asked any clear question” – Camus

Brady also suggests that we think of conversations as either "funnels" or "inverted funnels". 

The former start with generalities and then hammer in on the detail. "What are the benefits of free school meals, Mrs May?" / "Precisely how and where are you ensuring that every child is sufficiently nourished to be able to learn?"  It can be aggressive and adversarial; it's an approach modelled every day by John Humphrys and his hapless politicians.

On the other hand, you could structure your discussion as an "inverted funnel" by starting with small, specific issues, and then ascending to loftier terrains. "When did you last have a memorable conversation?" / "What makes a conversation meaningful?"  This tactic works particularly well when you realise that people are on edge and you want to put them at ease: you give them a small, manageable bone to fixate on, and then once they've relaxed you can slide them into the abstruse.  

2. WHEN YOU WANT TO... encourage innovation

Warren Berger describes himself as a "questionologist".  Whatever you feel about that title, some of his insights and suggestions are fascinating. He is convinced that a "beautiful question" can "begin to shift the way we perceive or think about something—and ... might serve as a catalyst to bring about change".

He's particularly persuasive about the importance of asking good questions in situations where "we don't know what we don't know" or, even worse, we (wrongly) assume that we do "know".  These are situations that are particularly likely to arise when working with experts from different disciplines, which are, ironically, the most fertile ground for innovation.

Berger suggests that while there are advantages in being informed as a questioner, equally it can be useful to be ignorant - an outsider who is free from conventional wisdom and able to ask questions with the penetrating naivety of a child. 

“Questioning is the tool that enables us to organize our thinking around what we don’t know” – The Right Question Institute

Another of his recommendations is that companies replace their tired mission statements with "mission questions", starting "how might we...?". "How might we best nourish ideas and people?"

Positing a question rather than presenting a statement frees employees to think creatively and responsively to changing situations. 

3. WHEN YOU WANT TO... find the answer yourself

Nancy Kline is a coach renowned for her techniques to create a "thinking environment" - essentially a recipe of conditions that enable the mind to think at its best, afresh, and for itself.

A key ingredient is "incisive questioning", in which you identify whatever assumption is holding your thinking back and then counter it with a liberating one. Essentially it's a hypothesis with the formula: "If you knew + freeing assumption + goal". The assumption might be a fact, a possible-fact or a bedrock view about how the world "is".

"If you knew that London is full of people who could help you fulfil your potential, what would you be doing?"

"If you believed that there are people who have got your back, what would your next step be?"

Dry on paper, playful in practice, this method has been described as a "tool of unbelievable precision and power". Once you start applying it you realise why.

What have we missed? Who is an exemplar of the artform? How have you learned to ask better questions?  Those are our questions; we're all ears for your answers.

Other pickings:

“You start a question, and it’s like starting a stone. You sit quietly on the top of a hill; and away the stone goes, starting others” – Robert Louis Stevenson