We’ve all heard the saying, “The only stupid question is the one you don’t ask.”

Well, I think that’s true. More or less. I mean, it works well as a general guiding principle but there seems to be a lot more to asking questions than blurting out the first one that comes to mind.

There is an art to it.

I guess any good interviewer and journalist knows that implicitly; the rest of us have to learn it the hard way. It’s an art which I thought I understood quite well until I read a book by Philip Mudd, a former CIA intelligence analyst. He worked on some of the most defining analyses of the last dew decades. The hunt for weapons of mass destruction in Iraq to name but one.

I thought, in hindsight rather foolishly, that his book might reveal some juicy titbits. No such luck. But what he did reveal about how to capture and analyse data – and create actionable intelligence out of it – was still worth its weight in gold.

How many times over the last few decades have we heard politicians, analysts and media pundits (among others) talk about “intelligence” failing us. As though the intelligence was a living, breathing thing.

It’s not.

And this is what became clear when I finished Mudd’s book.

Data is collected, compiled, maintained, accessed and analysed imperfectly. And data only becomes information (intelligence) when a context is applied to it, and when questions are asked of it. But those questions are always asked by a human. Although that is changing with the advance of artificial intelligence.

So if the intelligence has been said to have failed us, then what has actually happened is that we (humans) have either failed to collect the right data, in the right way at the right time from the right source, or we have failed to apply the right questions and context to it.

Add to that, the seemingly ever-growing list of cognitive biases which humans are prey to, and it’s easy to see why we sometimes end up making woefully inaccurate and inappropriate assessments, analyses and conclusions.

But what to do about it?

If we pay attention to Mudd’s experience and use the process in his book, plus a hefty dose of humility, we might just find ourselves making better informed analyses and decisions.

While his process of analysis is incredibly useful and easy to follow, the most important thing I learned from Mudd’s book was this:

  • Be aware of the intent behind your questions.

That’s part of step one of his process: setting the right question, one with enough context and one that enables you to gain what he calls “decision advantage”.

One way to know if you’re asking the right kind of question is to check whether your question is trying to predict the outcome of a situation.

E.g. Will we win the war? Yes, no, maybe, maybe not.

Or, is your question designed to allow you to understand how a situation is evolving, and what the possible outcomes could be, and the likelihood of each one occurring?

Either type of question isn’t automatically better than the other, but they do carry various risks which it’s good to be aware of.

Predictive questions can be very attractive because they appear to give us a definite answer and with that, certainty. But they can also be very misleading because they assume we have a sound grasp, and awareness, of how all the variables will play out.

Whereas exploratory questions allow you to understand how a situation is evolving, and serve to remind us that multiple outcomes may be possible, even if one is more or less likely than another.

Exploratory questions might be more complicated to answer because they are open-ended, and can cover a wider subject area, but they allow us to be more aware of a range of outcomes to consider, counter or work towards.

Whereas, if you ask a closed (predictive) question then it may only lead you to think there is only one possible answer, which means you’ll likely exclude alternative eventualities which may, in fact, be equally as possible or likely.

Having an awareness of the intent behind a question, isn’t the be all and end all of the art of asking questions, but it might help us better understand the nature of what we’re dealing with – be it a war or digital advertising campaign – and therefore let us make better decisions.