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Insightful Questionning

How to avoid stifling conversation and unearth new possibilities instead

One of my coaching clients, let’s call her Liz, prided herself on being a great questioner. She believed that by asking her team members questions, she empowered them to think for themselves and come up with the best solutions.

However, when I observed her in a meeting, I noticed that her questions were not opening new possibilities but closing them down.

It was like she was playing a game of 20 questions, where she had the answer in mind and was trying to get her team to guess it.

She would ask leading questions, such as “Don’t you think we should focus on X?” or “How can we make Y work better?” or “What are the risks of doing Z?”

Her questions were not inviting exploration, innovation, or creativity, but rather confirming her own assumptions, preferences, and biases.

This is a common trap that many leaders fall into without even realising it.

They think they are being incisive and curious, but they are being restrictive and directive.

They are not asking questions to unearth new possibilities but steering other people’s thinking in the direction they want.

This is like trying to fit a square peg into a round hole or forcing a plant to grow in the wrong soil. It may work for a while, but eventually, it will cause problems, such as frustration, resentment, conformity, or stagnation.

Research has found that people actively seeking information that challenges their assumptions are better able to update their beliefs in response to new evidence.

Seeking out diverse perspectives and evidence, enables you to overcome the limitations of your thinking and make more informed decisions.

Simple structured processes, such as divergent-convergent thinking, can be used to avoid this trap and foster more open and productive dialogue. Divergent-convergent thinking is a technique that involves first generating multiple options or perspectives (diverging) and then evaluating and selecting the best ones (converging).

John Coleman, author of Critical Thinking is About Asking Better Questions, says, “If you treat your own answer as a strawman, holding your assumptions loosely, you’ll be willing to totally abandon it if the situation calls for it.”

If you want to be an incisive leader who asks questions that unearth new possibilities, here are three practical things you can do to get started:

  • Check your intention. Before you ask a question, ask yourself: What is the purpose of this question? Am I trying to expand or narrow the conversation? Am I trying to learn something new or confirm something I already know? Am I trying to empower or persuade my team?
  • Check your tone. How you ask a question can influence how it is received and answered. Are you asking in a way that conveys genuine curiosity and respect, or are you implying criticism and judgment? Are you giving your team enough time and space to respond, or are you interrupting and dominating the conversation?
  • Check your process. How you structure your meetings can affect the quality and quantity of questions and ideas. Are you encouraging diversity and dissent or seeking consensus and harmony? Are you creating a safe and supportive environment, or are you creating fear and pressure?

Focusing on your intention, tone, and process can help you avoid the 20-question trap. This will also inspire your team to think more creatively, collaboratively, and critically and achieve better results.

Remember, you invite what you get back. Are you inviting the responses you need to achieve the desired outcome?

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