In many organizations, leaders are still taught to equate their worth with certainty, to believe that leadership means having the answers. The answers to where the company is going. The answers to what’s wrong with the team. The answers to how to fix every challenge that crosses their desk.
But if you’ve ever worked with a truly transformative leader, you’ll notice something interesting: they don’t pretend to have it all figured out. Instead, they ask great questions, the kind that stop people in their tracks, spark new thinking, and open up possibilities no one had considered before.
In today’s world of constant change, it’s the leader with the best questions who comes out on top.
The Myth of the All-Knowing Leader
For decades, leadership was modeled on authority and control. Leaders were expected to be experts. They’re the ones who knew more, decided faster, and gave directions with confidence. It worked in the industrial era, when predictability and efficiency mattered most.
But today, the problems leaders face are complex, interconnected, and often unprecedented. There’s no manual for managing remote teams across time zones, no single playbook for building culture during constant change, and no “right” answer for navigating global uncertainty.
The leader who insists on always being right, always knowing, often shuts down the very creativity and collaboration their team needs to succeed.
Why Great Questions Build Great Cultures
When leaders ask questions, they do something powerful: they shift ownership.
Instead of being the bottleneck for every decision, they invite others into the process. They create psychological safety, a space for people to share insights, challenge assumptions, and experiment without fear of being wrong.
Questions communicate trust. They say, “I value your perspective. I don’t just want you to execute. I want you to think.”
That mindset changes everything. Suddenly, meetings become conversations instead of updates. Teams feel energized to problem-solve. Innovation starts to feel like a shared responsibility, not a top-down initiative.
And, perhaps most importantly, people feel seen. When leaders ask questions that matter, it creates connection and builds culture.
How Questions Drove the Fox Digital Transformation
When I took the lead in designing and developing the Fox digital supply chain, I did not have the technical expertise to identify and build a solution. I also had no mandate from top management, so I needed to understand the needs of all the stakeholders and sufficiently address their concerns to create alignment around an acceptable solution.
I approached the challenge with curiosity as my primary focus. Rather than suggesting potential solutions, I began by asking questions that invited exploration and collaboration. Engaging key representatives from every discipline, including sales, sales servicing, engineering, IT, and finance, I sought to understand how each group defined the digital transformation challenge.
I posed questions such as:
- What slows us down today when delivering physical content?
- Where do we duplicate effort, and why?
- How might digital delivery impact our relationship with customers?
- If we could design our ideal digital supply chain from scratch, what would it look like?
These questions surfaced critical insights. Stakeholders revealed overlapping processes, redundant file creation, and a shared desire for speed and consistency. The group synthesized these discoveries into a guiding principle that resonated across every group: “Make it once, use it everywhere.” This became the north star for building the Fox digital supply chain.
The Shift from Directive to Curious
Curiosity is often underrated in leadership, yet it’s one of the most strategic tools available.
When a leader approaches a challenge with curiosity instead of defensiveness, they model a growth mindset. Instead of reacting with “How do I fix this?” they might ask, “What’s really happening here?” or “What can we learn from this situation?”
Those kinds of questions change the tone of a team. They move people from fear to exploration. They help uncover root causes rather than just treating symptoms. And they invite diverse perspectives, which are essential for solving today’s most complex problems.
Examples of Powerful Leadership Questions
Great questions don’t have to be complicated. They just have to be intentional.
Here are a few that consistently lead to deeper insight and stronger team engagement:
- “What’s the real challenge we’re trying to solve?”
(Helps teams cut through surface issues and clarify focus.) - “What are we assuming here, and are those assumptions still true?”
(Encourages critical thinking and adaptability.) - “If we could start over, what would we do differently?”
(Invites creativity and continuous improvement.) - “What’s one thing we’re not talking about that we probably should be?”
(Creates psychological safety and honesty.) - “What outcome would make this a win for everyone involved?”
(Promotes alignment and empathy.)
Each question empowers others to think for themselves, to lead from wherever they are.
Leadership in the Age of Uncertainty
In a rapidly changing environment, the best leaders are those who can stay centered in the unknown. Asking questions allows them to navigate uncertainty with confidence, not because they have all the answers, but because they trust the process of discovery.
This doesn’t mean abdicating responsibility. It means shifting from being the “chief problem-solver” to being the chief sense-maker, the person who helps others see clearly, connect dots, and make meaning out of complexity.
That’s what modern leadership looks like: clarity, not certainty. Curiosity, not control.
Having all the answers may make you look competent, but asking the right questions makes you a catalyst.
The best leaders know that leadership is about unlocking the intelligence in others. When you lead with curiosity, you build people who can solve problems together.
And in a world that’s constantly changing, that’s the most valuable skill of all.
