Decision Making Blog #6: The most powerful question in decision making?

I’m a fan of Shane Parrish and his organisation Farnam Street (strapline: ‘Helping you master the best of what other people have already figured out’). I’ve gained a lot from their books on mental models and have enjoyed many episodes of their podcast.

But the most valuable thing I’ve picked up from Shane’s work is a question.

My background in research and evaluation turned me into something of a question obsessive (we’re a small group, and we don’t get invited to many parties). I’ve carried this through into my work on strategy and decision making. Because time and again I’ve seen the power of a well-crafted, carefully placed question.

Questions are keys to unlocking insight. And while I don’t believe in the existence of generically useful questions – there are no skeleton keys here – I do try to collect questions that work in many situations.

So here’s the question I’ve taken from Shane: ‘How are you thinking about that?’ Very simple; grammatically slightly tilted; incisive.

Shane’s explanation of the power behind this question is here. My explanation is that the question of ‘how’ someone thinks requires an answer several layers deeper than the related questions of ‘what’ or even ‘why’ they think something. It can uncover hidden assumptions and insights that add real value to decision making.

One message in the decision making literature comes emboldened, underscored, italicised and in 32 point red font: the need for multiple perspectives on complex problems. Taking a range of opinions minimises individual blind spots. Gathering people’s views is therefore a commonplace of good decision making.

And so most of us are used to asking: ‘what do you think about this?’

Asking someone what they think elicits a view. The task is then to work out how useful that view is likely to be. Does the person know the subject well? Are they sighted on the likely consequences of this decision? Have they understood the organisational politics at play? Is their view likely to be partial in some unhelpful way? How should their view be weighed next to others? (etc).

Asking ‘what’ people think is helpful, but still leaves a lot of work. Having heard their views, one step further is to ask: ‘why do you think that?’

Answers to this question centre on justification. You gain a sense of their understanding, perspective, concerns, experience, and other evidence useful to them in explaining their opinions. This helps the decision maker see where the person is coming from. It further illuminates strengths and weaknesses in their argument.

But asking ‘why’ can also elicit a defensive response. Justifying a view is very different from exploring it. Our desire to be seen as smart and consistent and pleasant* is a wonderful instinct, but it can lead to us papering the cracks and avoiding the mouldy corners of our reasoning.

Which is why Shane’s question works so well. Asking ‘How are you thinking about that?’ means entering a conversation about the way someone is thinking.

Answers expose the different factors in play; the ways these factors relate to each other; how they see these relationships as they think things through. This shows the way they approach the subject at hand – exposing the mental models and frameworks that undergird their thinking.

In short, this question sets the conversation up as an exploration, not an interrogation. It is enquiring rather than adversarial. And it may give you a genuinely fresh perspective: a factor to consider that you were simply unaware of before asking.

* I collect quotes as well as questions. “Man naturally desires, not only to be loved, but to be lovely; or to be that thing which is the natural and proper object of love.” Even his greatest fans – and perhaps especially his greatest contemporary fans – wouldn’t guess that this was Adam Smith.