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The Art of Asking Better Questions

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Simone Duggan
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Smart questions make smarter people.

Good questions are powerful. They open the door to learn, understand problems and imagine better solutions, connect with others and push the boundaries.

Strategic leadership isn’t about having all the answers. It’s about asking better questions. In our fast-paced, digital world, the inquiry process has been replaced by on-demand answers. Technology has created a search-engine culture and we increasingly only have the patience for the ‘fast answer.’ 

Today, the art of asking good questions is hugely underrated. Somewhere around the age of five or six, children begin to learn their incessant streams of “Why?” and “Why not?” aren’t welcome, and it doesn’t take long for the fear of asking the ‘wrong thing’ to replace their wondering. But what if there’s something we can learn from the curiosity of a four-year-old?

Good questions are powerful. They open the door to learn, understand problems and imagine better solutions, connect with others and push the boundaries. Questioning is a uniquely powerful tool that can make conversations more productive and purposeful.

At SWARM Strategy, we always work from our golden rule: “Clarity, Strategy then Outcomes”. The secret to this rule is quite simple really; the order is key. Whatever the project or problem, we always seek clarity and understanding first, by asking ourselves and others compelling and thought provoking questions. Critical clarity is the catalyst to designing unique strategies, which only then leads to better outcomes.

“Questions spark ‘slow thinking’ - deliberate, effortful cognition that leads to better decisions, choices and actions.” - Warren Berger

To become a more strategic leader, practice the art of asking better questions. When you strive to ask questions that provoke thought and drive good dialogue with your team, you will raise your entire team’s collective ability to be strategic, cultivating the best in your team by provoking intelligent insights.

What’s stopping us?

Many situations we find ourselves in could benefit from more questions, yet we seem to be more comfortable offering our opinions and dispensing advice than asking. 

Why do so many of us hold back? Enter the fear of asking the wrong thing or appearing confrontational, our reliance on what we (think we) know, and a perceived lack of time - and already telling seems easier than asking.

The good news is, questioning is a skill that can be honed. So how do we relearn the art of asking questions like a four-year-old?

The best way to become a better questioner is simply to start asking more questions. Of course, not all questions are created equal. Consider how you can craft your questions to achieve at least one of these purposes - to build confidence and to inspire creativity - and you’ll discover the power of questions to ignite change in your team. 

Powerful questions serve at least one of two purposes:

1. Build confidence

Are your questions empowering? The questions you ask should instill confidence in the person you are asking, moving them to positive action rather than assigning blame. Your tone, the question type, sequence and framing all matter when ensuring the person you are asking feels confident their answer will make a difference or provide some valuable input.

2. Inspire creativity

A good question will inspire people to use their imagination and problem-solving skills. In today’s always-on world, there’s a rush to answer. Instead, craft questions to foster an environment of “slow thinking” and create room for creativity and deliberate cognition. 

The art of questioning is a vital skill for anyone who wants to excel in creativity, leadership, decision-making and interpersonal skills, but proper questioning and inquiry has become a lost art in modern society. As a leader, start asking yourself and your team more questions and promote questioning in your organisation. It requires slowing down to leave space for purposeful cognition, a certain amount of vulnerability and a culture shift - not only for your organisation, but also your own mindset. 

Some all-purpose questions to get started:

  • How can I see this with fresh eyes?
  • What matters most?
  • How might we change this?
  • What are we against?
  • What does success look like for our team?
  • What would an outsider do?

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