How to ask the right questions

February 7, 2023
Before you jump straight into problem solving mode, make sure you are taking time to properly consider the issues at hand.

Imagine someone’s asked you to come up with an idea for something.

They might have given you a formal brief, or maybe they just asked in a one-line email. It’s tempting just to dive in and try to immediately come up with something that satisfies them.

You should try to resist that temptation.

Shallow Thinking

In today’s fast-paced business environment we often move too quickly to idea generation before taking time to properly consider the issues at hand. The ideas or solutions you come up with initially will be the most obvious, what you might call shallow thinking. They will often be cliché-ridden stereotypes or quick rehashes of previous ideas.

So before you start, think about why they’ve asked for it. Questioning the brief doesn’t necessarily mean finding fault with it, but asking questions about the motivations behind it, or the trigger points that led to it, can really help you come up with better ideas and solutions.

Digging Deeper

To dig deeper into a brief or problem, try and think about how you can view it from different angles or perspectives. Zoom out to think about the wider causes or implications, and zoom in to dissect every small detail. Think about how various others (colleagues, leaders, competitors, original thinkers) might view the same brief, and how they might approach it.

Essentially, you'd benefit from asking as many questions as possible about the brief you've been given. You don't need to ask all these questions to the source of the brief, you can just ask yourself - use questioning as a valuable creative thinking technique.

The Right Question Institute has developed its own "Question Formulation Technique" to help people ask good questions.

Another good start is this approach from the CIA. The Phoenix Checklist features two lists of questions to help you drill into problems and plans. Some of our favourite questions from the list:

  • Why is it necessary to solve the problem?
  • What is it you don’t yet understand?
  • What are the best, worst and most probable cases you can imagine?
  • How will you know when you are successful?

Other great questioning techniques include the 5 Whys and How Might We.

Being Resilient

Try and keep on questioning even when you come up against resistance. For example have you ever asked: "why do we do it this way" only to receive the answer: "because we always have"? It's important to try to get past these obvious answers.

And you can expect to be questioned about your questioning approach too - people are often so anxious to "get things done" that they have little patience for questions. "Don't bring me questions, bring me answers!" they might say.

Push on. As Warren Berger, author of A More Beautiful Question, says: "Companies should be careful about discouraging fundamental, seemingly naïve questions - which can be a valuable tool for challenging the most basic assumptions about why and how your company does what it does."

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