Select Page


“The power to question is the basis of all human progress.”

– Indira Gandhi

In a business landscape marked by rapid changes and high unpredictability, mastering the art of smart questioning is no longer a luxury – it’s a necessity. The traditional emphasis on having ready answers is shifting; today, the key differentiator is the ability to ask insightful, strategic questions that unlock creativity and drive innovation.

The Importance of Questioning

Leaders like Citi’s CEO Jane Fraser and Nvidia’s Jensen Huang exemplify this shift. They recognize that they don’t have all the answers. Instead, they focus on asking the right questions that empower their teams to explore new ideas and solutions. This approach not only fosters a culture of curiosity and learning but also helps in tapping into the collective intelligence of the organization.

The Art of Question-Storming

“Question-storming” is a technique where leaders brainstorm questions instead of answers. This method encourages a deeper understanding of challenges and welcomes new avenues for creative problem-solving. For instance, business leaders are now adopting styles where they engage less in directing and more in facilitating discussions that challenge the status quo and uncover hidden insights.

A Practical Framework for Effective Questioning

The Harvard Business Review article titled, “The Art of Asking Smarter Questionshighlights a structured approach to asking questions, categorized into five key areas —investigative, speculative, productive, interpretive, and subjective — which together, enable a comprehensive exploration of strategic issues.

Here’s a brief look at these categories:

  • Investigative Questions: Diving deep into the known facts, pushing for detailed and often overlooked information.
  • Speculative Questions: Exploring the ‘what ifs’ and encouraging thinking beyond conventional boundaries.
  •  Productive Questions: Focusing on the resources and the ‘how-tos’ of turning strategies into actions.
  •  Interpretive Questions: Synthesizing information to redefine problems and understand their deeper implications.
  • Subjective Questions: Addressing the underlying emotional and personal dynamics that can impact decision-making.

  Lessons from Business Failures and Successess 

Real-life examples, both the good and the bad, underscore    the importance of a balanced questioning approach. For        example, a misstep by French rail operator SNCF with            train sizes due to inadequate investigative questioning led    to a costly error. Conversely, the innovative success of            Emirates Team New Zealand in the America’s Cup                    illustrates the power of speculative questioning in breaking free from industry norms and achieving breakthroughs.

Developing a Questioning Culture

Creating a culture that values and encourages effective questioning is critical to long term success. Leaders need to cultivate a diverse team that can cover all aspects of the questioning spectrum, ensuring that no critical area is neglected. This includes being open to adjusting one’s questioning style to suit different situations and complement personal blind spots.

As we navigate a world where answers are plentiful but the right questions are like a rare jewel, leaders must hone their ability to ask smarter, more strategic questions. This not only drives innovation and creativity but also equips organizations to handle the complexities of modern business dynamics more effectively. By fostering a culture that prioritizes these skills, businesses can unlock a significant competitive edge. The art of asking smarter questions isn’t just about being more knowledgeable – it’s about being more adaptable, thoughtful, and strategic in a constantly evolving business environment.

For any leader or strategist, refining your questioning skills is not just beneficial—it’s essential.

How have strategic questions reshaped your planning processes or opened new avenues for innovation in your work?


You’ve got this.