Hal Gregersen's journey into the realm of questioning began nearly 30 years ago during his experiences of living and working in various countries, including Finland, England, the United States, France, and the United Arab Emirates. These international encounters taught him the vital lesson that assuming knowledge in unfamiliar contexts can lead to grave misunderstandings. To navigate these challenges, successful leaders demonstrated exceptional skills in asking the right questions to unlock new insights and actions.

Hal's observations led him to recognize that questioning was a key driver of innovation and transformation. By challenging assumptions and exploring new possibilities, leaders could uncover hidden opportunities and develop groundbreaking solutions. Inspired by these experiences, he dedicated his career to understanding and promoting the power of questions in driving meaningful change.

The evolution of leadership and the role of questions 

Over the past three decades, Hal's research has consistently revealed a common theme among successful leaders: the skill of asking catalytic questions. These questions challenge fundamental assumptions and energize individuals and teams to pursue alternative approaches. While the traditional view of leaders is often associated with having all the answers, the disruptive nature of today's world calls for a paradigm shift. Leaders who embrace questions and encourage their teams to do the same are better equipped to navigate uncertainty and drive innovation.

Hal emphasizes that asking the right questions is not about being confrontational or aggressive. Instead, it is about fostering a mindset of curiosity and exploration. By approaching challenges with a sense of wonder and a genuine desire to learn, leaders can uncover new perspectives and possibilities that may have otherwise been overlooked. This approach to questioning not only leads to better outcomes but also empowers individuals to take ownership of their work and contribute to the organization's overall success.

The tension between perception and reality 

A significant tension exists between the popular perception of management and the behaviors exhibited by effective leaders. Hal's research shows that the stereotypical image of managers as controllers or problem solvers contradicts the qualities exhibited by innovative leaders. The ingrained perception of managers as authority figures stifles the natural inclination to ask questions.

To overcome this tension, innovative leaders create environments where fearless questioning can thrive, cultivating a culture that fosters curiosity, exploration, and experimentation. They break away from the traditional hierarchical structure and encourage open communication and collaboration. By empowering employees at all levels to ask questions, share ideas, and challenge existing norms, these leaders foster a sense of ownership and engagement, leading to higher levels of innovation and transformative growth.

The art of asking better questions 

While there is no one-size-fits-all framework for asking questions, Hal shared a powerful technique called a "question burst." He discussed this approach in a recent Harvard Business Review article. It involves dedicating a focused period of time to ask questions about a specific issue or challenge. The rules are simple: no answering questions and no explaining the reasons behind the questions. By removing the need for immediate answers and explanations, participants can delve deeper into the issue, generating a multitude of questions that can reframe the challenge, evoke new insights, and foster a more positive emotional state.

Question bursts are designed to disrupt habitual thinking patterns and encourage individuals to explore different angles and possibilities. They help uncover assumptions, uncover blind spots, and challenge the status quo. This technique can be applied at both the individual and organizational levels, serving as a powerful tool for personal growth, team collaboration, and organizational transformation.

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The role of culture in fostering a questioning mindset

Creating a culture that nurtures a questioning mindset is essential for organizations seeking to innovate and thrive in a rapidly changing world. Hal emphasizes that culture is not just a collection of artifacts or slogans; it is the behaviors and practices that are consistently reinforced and rewarded within an organization.

Leaders play a crucial role in shaping culture by modeling the behaviors they want to see in their teams. When leaders openly ask questions, actively listen, and embrace diverse perspectives, they set the tone for a culture that values curiosity and continuous learning. Additionally, leaders need to create psychological safety, where individuals feel comfortable taking risks, challenging the status quo, and asking provocative questions without fear of judgment or reprisal.

By fostering a culture that encourages questions, organizations can tap into the collective intelligence of their workforce, unlock new ideas, and create an environment that thrives on innovation and transformation. Cultivating a questioning mindset is an ongoing journey that requires commitment, intentionality, and a willingness to embrace the unknown.

The power of diversity: inviting varied perspectives

Diversity plays a pivotal role in brainstorming sessions, fostering an environment where a wide range of perspectives, experiences, and ideas can flourish. As Alex and Hal conversed, they acknowledged the significance of diversity in driving innovation and problem-solving. Alex highlighted that "diversity brings different viewpoints and approaches to the table, which can lead to more creative solutions." Hal echoed this sentiment, stating that "diversity encourages the exploration of various angles, enabling us to challenge assumptions and uncover unique insights." By incorporating individuals from diverse backgrounds, industries, and cultures, brainstorming sessions can tap into a rich tapestry of ideas, enhancing the potential for breakthrough innovations and comprehensive problem-solving.

Embracing the awkwardness: the power of questions in leadership

In the second half of the conversation between Alex Osterwalder and Hal Gregersen, the importance of questions as a leadership tool becomes even more apparent. As Hal points out, in times of uncertainty and on the edge of the unknown, questions are the answer. When faced with situations where answers are not readily available, leaders must turn to questions to navigate the uncharted territories.

Hal emphasizes that it's not a matter of choosing between questions or answers, but rather understanding the context in which each is most effective. Questions become indispensable when operating in the face of uncertainty. They act as vehicles for exploration, allowing leaders to venture into the unexplored and discover new possibilities.

However, the timing of questions is crucial. Hal stresses that leaders must be aware of their position and the impact it can have on the dynamics of a room. In some cases, leaders need to refrain from immediately asking questions, especially at the start of a meeting. By creating a safe space and encouraging others to ask questions first, leaders foster an environment where diverse perspectives can emerge. This approach helps prevent the team from interpreting the leader's questions as directives, thereby stifling independent thinking.

Hal introduces the concept of reflective quietness, wherein leaders consciously choose to be silent and observant.

The example of Mark Benioff, co-founder and co-CEO of Salesforce:

Embracing discomfort and actively seeking out uncomfortable situations is indeed a pattern that Hal has observed among many top leaders he has interviewed. One such leader is Mark Benioff, the co-founder and co-CEO of Salesforce. Despite his success and senior position in the organization, Mark has maintained a practice of listening and seeking out diverse perspectives.

During a conversation with Mark at the Davos meeting, he emphasized the importance of listening. When he told me to listen, he watched my reaction closely to determine whether I truly understood the significance of his words. This demonstrated Mark's commitment to being fully present and engaged in the act of listening, rather than just going through the motions. This approach is a powerful tool for leaders to gain insights and understand the needs and challenges of their teams and organizations.

One common challenge that many senior leaders face is being insulated from uncomfortable information by a protective circle around them. They may have staff members who filter and shield them from surprising or awkward information. However, leaders like Mark consciously avoid this trap by actively seeking out diverse perspectives and uncomfortable information.

After leaving Oracle, Mark embarked on a listening tour, engaging with people from various backgrounds and industries. This open-minded approach allowed him to gain a broader understanding of different businesses and their challenges. It was through this process of exploration and inquiry that he arrived at a catalytic question: "What if we sold enterprise-level software like Amazon sells books?" This question challenged the status quo and ultimately led to the success of Salesforce.

But the journey doesn't end with a catalytic question. Leaders like Mark understand that maintaining a culture of curiosity and discomfort is crucial for continued innovation and growth. They create spaces for transparency and open dialogue within their organizations. For example, Salesforce makes its strategy meetings transparent, allowing anyone in the organization to watch and provide input. This practice fosters a culture of collaboration and ensures that diverse perspectives are considered in decision-making processes.

Furthermore, leaders like Mark embrace open communication channels where employees can share grievances and provide feedback. Even when faced with raw and uncomfortable conversations, Mark recognized the value of these exchanges and refused to shut them down. Instead, he saw them as opportunities to identify areas for improvement and to keep a pulse on the organization's strengths and weaknesses.

By actively embracing discomfort and cultivating a culture of curiosity and transparency, leaders like Mark Benioff create an environment that encourages asking better questions. They understand that the role of a leader is not to have all the answers, but to foster a collective intelligence that drives innovation and growth. It is through the power of questions and the willingness to be uncomfortable that organizations can navigate uncertainty and chart a path toward success in an ever-changing world.

In conclusion, the ability to ask better questions is a skill that can be developed and honed. It starts with a base set of questions, such as "What's working, what's not, and why?" and then expands to more exploratory and prescriptive questions that challenge assumptions and explore new possibilities. However, timing is key, and leaders must be aware of the context and create safe spaces for others to ask questions. Embracing discomfort and actively seeking out uncomfortable situations is crucial for continuous learning and growth. Leaders who embrace this mindset, like Mark Benioff, set the stage for their organizations to thrive in an uncertain and rapidly changing world. By asking better questions and creating an environment that encourages curiosity and open dialogue, leaders can unlock the collective intelligence of their teams and drive innovation and success.

Becoming a better questioner

Ultimately, becoming a better questioner requires practice, self-awareness, and a genuine curiosity to explore new perspectives. By developing the skill of asking powerful questions, individuals can unlock innovative thinking, challenge the status quo, and drive meaningful change.

In a world characterized by uncertainty and constant change, the ability to ask the right questions has become a critical skill for individuals and organizations alike. Leaders like Mark Benioff and the insights shared by Hal Gregersen in this conversation and in his book remind us of the transformative power of questions and the importance of embracing discomfort to unlock new possibilities.

So let us embrace the art of questioning, for it is through our questions that we navigate the complexities of the present and create a brighter future. As we continue to explore the boundaries of what is known and seek answers to the unknown, let us remember that questions are not merely tools for inquiry but catalysts for growth, innovation, and transformation.

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