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Asking challenging questions is creative fuel for valuable conversations when trying to solve a problem. And the short “Why?” has gained its wide group of supporters¹. It’s considered a way to spark interest and provide a deeper understanding. But this is not always the case.

Children discover the world by asking the question “Why?” with genuine curiosity and amazement. On the other hand, when something goes wrong, they are compelled to explain themselves. However, applying the same approach to adult conversations, particularly in professional settings, often results in unintended consequences.

This dual role of ‘Why?’—curious and accusatory—becomes problematic in adult leadership conversations. We may see how, often, “Why?” is actually harming empathy, openness, and productive discussions.

Of course, the question “Why?” can be useful at times, particularly in safe environments where root-cause analysis is required. Still, its effectiveness is quite situational. Leaders should consider that more thoughtful and detailed questions generally lead to better conversations.

The collection of exemplary questions presented by Michael J. Marquardt in his book “Leading With Questions”² includes those that encourage individuals to maintain the right focus and to stretch themselves, alongside fostering deep reflection. These questions invite reflection and expand thinking by focusing on possibilities rather than judgement. “What is a feasible alternative?”, “Could you elaborate on your concerns?”, and “What are a couple of options for enhancement?” are just a few examples of this. They all share a common element—they differentiate the individual from the issue.

“Separate the People from the Problem” is a concept from the influential book “Getting to Yes”³ by Roger Fisher and William Ury. And it’s a foundation for the next steps— to focus, find options, and apply objective criteria to a solution. Asking, “Why?” is triggering defensiveness and personalising issues, contradicting the principle of separating people from problems. They advocate using objective, collaborative questions instead, ensuring discussions focus on shared interests and mutual understanding.

Effective leadership involves distinguishing between questioning that seeks to assign blame and asking that aims to understand and improve. Peter Drucker’s framework⁴ of five essential questions—”​What is our mission?”, “​Who is our customer?”, “​What does the customer value?”, “​What are our results?”​, and “​What is our plan?”​—exemplifies this approach. These questions foster self-reflection and strategic thinking without putting individuals in a defensive position. ​

In daily operations, every one of the team members is able to set directions by focusing on four fundamental questions: “​Where are we now?”, “​How did we get here?”, “​Where do we want to go?”​, and “​How will we get there?” This structured approach promotes clarity and direction by enabling teams to effectively align their efforts with organisational goals.

By prioritising understanding over interrogation, everyone is empowered to cultivate an environment conducive to growth and innovation. This approach not only fosters collaboration but also encourages each member to contribute their unique perspectives and ideas in open dialogue for innovations⁵. Ultimately, this collective effort drives the team towards achieving their objectives while adapting to the landscape and achieving more.

1. Before Galileo Galilei published “Dialogue Concerning the Two Chief World Systems” in 1632, the prevailing common belief was that the Earth was stationary at the centre of the universe, with the Sun and planets revolving around it. ↩︎
2. Michael J. Marquardt (2014). Leading with Questions: How Leaders Find the Right Solutions by Knowing What to Ask Hardcover, https://www.amazon.com/Michael-J-Marquardt/e/B00JPVF424/ref=dp_byline_cont_book_1 ↩︎
3. Roger Fisher, William Ury (1991). Getting to Yes: Negotiating Agreement Without Giving In, https://www.pon.harvard.edu/shop/getting-to-yes-negotiating-agreement-without-giving-in/ ↩︎
4. Andrew Sobel (2014). Peter Drucker’s Five Magic Questions, https://andrewsobel.com/article/peter-druckers-five-magic-questions/ ↩︎
5. Jacobs, C. D., & Heracleous, L. (2005). Answers for questions to come: Reflective dialogue as an enabler of strategic innovation. Journal of Organizational Change Management, 18(4), 338–352. https://www.heracleous.org/uploads/1/1/2/9/11299865/jacobs_heracleous_2005_jocm.pdf ↩︎