The Leadership Skill AI Can’t Replace: Asking Better Questions
In the ever-evolving landscape of technology and business, the quest for answers has long been the guiding light for leaders across various domains. However, from lifeguarding to product design and executive leadership, one crucial lesson remains constant: better questions foster better judgment. This insight shifts the focus from merely having the right answers to cultivating a culture of curiosity and critical thinking.
The Lifeguard’s Lesson: The Power of Inquiry
During my tenure as a lifeguard supervisor, I learned that true leadership wasn’t about having all the answers. Instead, it was about empowering my team to make swift, high-stakes decisions with precision. The ocean, indifferent to human expertise, taught us that no amount of training could prepare us for every contingency. The unpredictable nature of rescues demanded a different approach—one rooted in asking the right questions.
Questions like “Is the victim visible?” or “What’s the current doing?” sharpened our focus and built confidence. This focus, in turn, refined our judgment, making us more effective in life-saving situations. The lesson was clear: asking the right questions was a catalyst for success, a principle that transcends the sandy shores of the beach and extends into the boardroom.
The Allure of Answers and Their Limitations
Answers, undeniably, bring a sense of satisfaction. They tidy up meetings and make presentations compelling. However, in a world where markets shift rapidly and AI accelerates change, answers can quickly become obsolete. The answer that worked last quarter may already be outdated.
In contrast, questions have a longer shelf life. They provide direction in turbulent times and encourage teams to think independently. This is the essence of leadership—granting permission to think, explore, and innovate. It’s about creating an environment where teams feel safe to question the status quo and challenge existing paradigms.
The Transformative Power of “The Question”
I once had the privilege of working with a President of Operations who embodied the art of asking the right questions. Regardless of the meeting’s nature—technical, financial, or otherwise—he always posed “THE question.” This was not the smartest answer but the inquiry that could shift perspectives and elevate conversations.
His questions often prompted an “oh… wow” moment, making people pause and reconsider their assumptions. By modeling curiosity, he encouraged a culture where others felt empowered to do the same. This shift in mindset not only transformed team dynamics but also drove the business forward. Better questions led to better judgment, and better judgment led to superior outcomes.
Questions as a Leadership Compass
Over the years, certain questions have become my internal compass, guiding my leadership approach across various roles:
1. What does success look like from their side?
Leadership, like hosting, is about designing experiences for others. Understanding success from the perspective of those you serve ensures that your efforts align with their needs.
2. Who actually needs to understand this decision?
Effective leadership scales through shared clarity, not control. Identifying who needs to comprehend the “why” behind decisions empowers them to act independently.
3. What’s the smallest version of this that teaches us something?
In both lifeguarding and technology, small experiments lead to significant insights. Balancing learning velocity is key—turning uncertainty into understanding efficiently.
4. What needs to stop so this can start?
Prioritization involves making tough choices about what not to pursue. Avoiding task saturation ensures that efforts are concentrated on the most critical initiatives.
5. How do we make this a habit, not a one-off?
Building sustainable rhythms and habits ensures that progress is maintained over time. Culture, driven by consistent practices, carries judgment forward even when leaders are absent.
The Underlying Question
In high-pressure situations, hesitation often stems from uncertainty, not a lack of training. This highlights the quiet cost of answer-driven leadership—people wait for direction. In contrast, questions create permission, signaling trust and empowering teams to make decisions when it matters most.
The Timeless Work of Leadership
As AI continues to make answers cheaper and faster, the core challenge of leadership remains unchanged: seeing clearly, asking well, and creating spaces where teams think critically and creatively. The best leaders, whether on the beach or in the boardroom, are those who ask the questions that propel work and people forward.
So, I leave you with this question: What question would change everything for your team if you actually asked it?
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I’m Zab, a Product Designer and Strategist committed to helping enterprise teams solve the right problems with clarity, creativity, and systems thinking. Through these reflections, I explore the intersection of Leadership, Product, AI, and the synergy between Business and Experience to build meaningful solutions.
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