TDL Library: Asking Great Questions

Leadership isn’t about having all the answers,  it’s about asking the right questions. Great leaders aren’t the ones who pretend to know it all, nor are they the ones who shy away from admitting they don’t. Instead, they are curious, inquisitive, and unafraid of exploring the unknown. In his book, Good Leaders Ask Great Questions, John Maxwell emphasizes the power of a well-asked question to unlock potential, create connection, and drive growth. Will Wise, in Ask Powerful Questions, further expands on this idea, teaching us that questions are the key to deeper understanding, authentic relationships, and meaningful progress.

At The Damaged Leader, we recognize that our imperfections and vulnerabilities are not weaknesses but strengths. Embracing our flaws allows us to lead with authenticity and empathy. One of the most powerful ways we can do this is by asking great questions. Questions are the bridge between what we know and what we don’t, between who we are and who we aspire to be. They are tools for transformation - not just for those we lead, but for ourselves.

Embracing Curiosity Over Control

Maxwell’s book underscores a critical truth: the best leaders are not those who dominate conversations with statements but those who open doors with questions.

Asking great questions shows humility. It admits, “I don’t have all the answers, and that’s okay.” It’s a radical departure from the idea that leaders must be all-knowing figures of authority. Instead, it positions leaders as curious explorers, willing to delve into uncertainty.

Similarly, Wise highlights that powerful questions do not just seek information, they seek connection. Questions like “What do you think?” or “How can we make this better?” do more than gather facts, they invite others into the problem-solving process. They create a sense of ownership and build a deeper, more resilient team dynamic. These are questions that damaged leaders, who understand the beauty of vulnerability, ask to empower and engage those around them.

The Courage to Ask the Hard Questions

As damaged leaders, we know that life is full of unanswered questions - those lingering doubts and uncertainties that leave cracks in our confidence. But it is precisely because of these cracks that we have the courage to ask hard questions. When we embrace our own brokenness, we make space for the questions that truly matter: “Why are we doing this?” “What’s holding us back?” and “How can we support each other better?”

Maxwell and Wise both emphasize that powerful questions often challenge the status quo. They cut through the noise and bring us back to what’s important. Asking these questions requires courage because they may reveal uncomfortable truths. But leaders who have embraced their own imperfections understand that discomfort is not something to be avoided, it is something to be explored.

Creating Space for Authenticity

Wise’s concept of creating space in conversations resonates deeply with our theme at The Damaged Leader. He argues that powerful questions create space for others to share their stories, fears, and dreams. For leaders who know the weight of imperfection, asking great questions becomes a way to foster an environment of openness and authenticity.

Questions like “What’s challenging for you right now?” or “How can I better support you?” show that leaders are not only interested in tasks and outcomes but in the people behind them. This approach aligns perfectly with the ethos of a damaged leader, someone who understands that connection is built on honesty, not perfection.

Transforming Through Inquiry

Both Maxwell and Wise teach us that asking questions is not just a skill but a transformational practice. For damaged leaders, this transformation begins with ourselves. We start by asking, “What can I learn from my mistakes?” “How can my experiences help others?” and “What do I need to grow?” These questions are not easy, but they are essential. They turn our scars into strengths and our vulnerabilities into vehicles for connection.

When we ask great questions, we not only learn more about those we lead, we learn more about ourselves. We discover that our struggles are not a barrier but a doorway to deeper understanding and empathy. As leaders, we use our questions to break down walls, build bridges, and create spaces where imperfection is not just accepted but celebrated.

Conclusion: The Gift of Inquiry

At the heart of great leadership is a willingness to ask, to listen, and to learn. Maxwell and Wise remind us that questions are more than just queries, they are gifts. They are opportunities to connect, to understand, and to grow. For damaged leaders, questions can be the golden seams that bring our broken pieces together, making us stronger, more relatable, and more effective.

So, let us embrace the power of asking great questions. Let us lead not by having all the answers, but by having the courage to ask the questions that matter most. In doing so, we will not only become better leaders, we will become better humans, beautifully imperfect and always seeking to understand.