How asking questions is a leader’s greatest skill

Imagine a leader who does all the talking, never seeks input from their team, and assumes they have all the answers. It is safe to say that this leader will not be very effective in the medium to long term. In the world of leadership, one of the most underrated yet indispensable skills is the ability to ask questions. The power of asking the right questions is often underestimated, but it can make all the difference in how a leader guides their team, solves problems, and fosters innovation.

This week, I wanted to explore why asking questions is an excellent skill for a leader. I delve into the importance of this skill, how it benefits leaders, their teams, and their organisations, and provide practical insights on how to become a more effective leader through the art of questioning.


Before I dive into the importance of asking questions as a leader, I want to take a moment to explain what leadership questions are. Leadership questions are open-ended, thought-provoking inquiries that encourage critical thinking, problem-solving, and the sharing of ideas. They can be aimed at team members, peers, or even oneself. The power of these questions lies in their ability to stimulate dialogue, drive decision-making, and promote learning and growth. They are not got-you questions, or questions designed to entrap people, show them up or make them look stupid. Be inauthentic, agenda-driven for your benefit, and it will backfire spectacularly.

Questions need to be intentional and delivered with good intentions. If a leader starts there and follows their instinct, the leader will not go astray.


What kind of questions does a leader need in their repertoire?

Questions that:

  • Encourage critical thinking: Leadership is not about providing all the answers but fostering an environment where team members are encouraged to think critically. Influential leaders use questions to challenge the status quo and provoke fresh insights. Posing thoughtful questions stimulate the cognitive process, leading to a deeper understanding of complex issues.
  • Promote engagement and ownership: Asking questions empowers team members to take ownership of their work and contribute actively to the decision-making process. When people feel their opinions matter, they become more engaged and committed to their tasks and the organisation’s goals. Questions like, “What do you think is the best approach?” demonstrate trust and value in team members’ input.
  • Foster open communication: Open, honest, and transparent communication is a hallmark of effective leadership. Questions create a safe space for dialogue, where team members can express their thoughts, concerns, and ideas. This open communication fosters trust, strengthens relationships, and prevents misunderstandings. A simple question such as “I sense something is not being said. Would you be open to sharing?” is one such way of opening the door to open communication.
  • Navigate complexity: Today, leaders often face complex and ambiguous challenges. Questions help break down these challenges into manageable parts. Leaders can navigate complexity more effectively by asking questions that clarify, probe, and challenge assumptions. Questions like “What is the problem we are trying to solve?” and “What are the potential consequences of each option?” help structure the decision-making process.
  • Lead by example: Leaders who ask questions set a powerful example for their team members. They show that they are not above seeking advice or considering different perspectives. Asking questions encourages a culture of curiosity and continuous improvement within the organisation. If the leader asks and responds appropriately, it allows others to feel safe asking. 
  • Learn and adapt: We know that we live in a rapidly changing world and that leaders must be adaptable and open to learning. Asking questions is a way to gather information, learn from mistakes, and continuously improve. Leaders who seek feedback from their teams and ask questions such as “What can we do better next time?” are more likely to stay ahead in a constantly evolving landscape.

And like all things in life, it takes practice to develop good questioning skills without coming across like a drill sergeant. So here are some practical tips to develop your questioning muscle.

Start with open-ended questions

Encourage dialogue and critical thinking by asking questions that cannot be answered with a simple “yes” or “no.” For example, ask, “What are your thoughts on this approach?” instead of “Do you agree with this approach?”

Listen actively

Easier said than done. However, as leaders, we need to understand that asking questions is not just about speaking but also about listening. Pay close attention to the responses you receive and use follow-up questions to dig deeper into the conversation. Here, I suggest using your instincts to follow up. Clarify. Force yourself to ask, at a minimum, three questions before you think you know. 

Create a safe environment

I am big on this because I have seen many environments and leaders who do not take the time to make their team feel comfortable sharing their thoughts and ideas. But as leaders, we are always on. So, work to avoid judgment and criticism and create an environment where all questions are welcomed, even when they might not be palatable.

Balance advocacy and inquiry

While asking questions is essential, there are times when leaders need to advocate for a particular direction. I live in the real world, too.  So, balance advocating your perspective and inquiring about others’ viewpoints. Like all things in leadership, the skill is in finding the balance. Tip in either direction too far, and it will not end well. If in doubt, always ask the questions, listen actively, and tell people you have taken their input and value it. If you decide to go in a different direction, then explain that.

Open communication and transparency become critical. Otherwise, a leader will lose trust, and the team will not be open next time. It is okay to let your team know that other factors and other players must also be catered to, but it does not take away from their contributions and value.

Reflect on your questions

After discussions or meetings, take a moment to reflect on the questions you asked. Were they effective in achieving your goals? In moving the conversation forward? What could be improved next time? Take the time to hone this skill. I am confident it will help you become a more effective leader and set you apart from other leaders in your organisation or team.

Final thoughts

A leader who has mastered the art of asking questions has a powerful tool. The ability to inquire, listen, and encourage critical thinking can transform their leadership style and the dynamics within their teams and organisations. Leaders who ask questions become catalysts for growth, build trust and become better communicators. It also sets them apart and can propel their careers.   The influential and effective leaders of tomorrow are the ones who recognise the transformative potential of a simple yet invaluable skill—the skill of asking questions. How will you practice this coming week?

And as always, if you invest in yourself, the rewards will be unfathomable.

Until next time.

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