Leaning Into Your Curiosity: Ten Game-changing Questions

During a recent CEO Forum, I enjoyed the privilege of facilitating a conversation about the role of curiosity in group meetings and for leaders in general. What struck me most was how often leaders believe they are going deep when, in fact, they are only skimming the surface. Genuine curiosity requires us to slow down and challenge the assumptions we may not even realize we are holding. The goal is to avoid making those assumptions, jumping to conclusions, or rushing to judgment, and instead, listening for understanding. It’s not easy. It requires discipline, intentionality, and practice.

For me, curiosity begins with an internal check: What do I think I know, but don’t really know for sure? This simple practice allows me to pause, reconsider, and open myself up to asking more questions – questions that most people may have stopped asking themselves. If you are willing to confront your own blind spots, it will help you lean into richer conversations with others.

Curiosity is not about collecting more information. It’s about discovery. It’s about contributing to the kind of psychological safety in a team where those questions can be voiced and fearlessly explored. And it’s about using those questions to uncover insights that might otherwise go unspoken.

Curiosity as a Leadership Discipline 

Leaders today face increasingly complex challenges. Traditional answers are often insufficient, and quick fixes rarely endure. Cultivating curiosity as a discipline helps leaders resist the temptation to default to what they already know. Instead, curiosity empowers them to explore new perspectives.

Practicing curiosity does more than sharpen decision-making. It fuels innovation, strengthens culture, and builds resilience. When leaders ask profound questions, they show how much they care and send a powerful signal that exploration is valued over certainty.

Ten Questions to Go Deeper 

The following ten curiosity questions are adapted from the work of Dr. Diane Hamilton, author of Cracking the Curiosity Code and Curiosity Unleashed. They reflect her framework for identifying and overcoming curiosity blockers, encouraging deeper inquiry, and fostering more innovative and engaging conversations.

1. The “Missing Piece” Question 
   What are we missing here? It opens up blind spots, challenges assumptions, and surfaces overlooked insights.
2. The “Unspoken Concern” Question 
   What’s something we’re not talking about, but should be? This creates psychological safety by allowing hidden worries to emerge.
3. The “Ripple Effect” Question 
   If we go with this decision, what could be the second or third-order consequences? This question pushes the team to think beyond immediate results.
4. The “Resistance” Question
   What might make someone hesitate to support this idea? This query brings potential barriers and skepticism into the open early.
5. The “Curiosity Gap” Question
   What do we still not know, but need to learn, before moving forward? It separates fact from assumption and highlights where more discovery is needed.
6. The “Alignment” Question
   How does this connect with our larger purpose or goals? This ensures ideas stay connected to vision and mission.
7. The “Dissent Invitation” Question (My favorite)
   Who sees this differently? This question encourages diverse viewpoints and reduces groupthink.
8. The “Empathy” Question
   If you were in the customer’s or employee’s shoes, how would this feel? It fosters emotional intelligence and perspective-taking.
9. The “Simplicity” Question
   What’s the simplest way we could achieve the same outcome? This query strips away complexity and sparks creative alternatives.
10. The “Future Lens” Question
    If we looked back a year from now, what would we wish we’d asked today? It serves to help move beyond short-term thinking into foresight.

Making Curiosity a Habit 

In my own practice, I use these questions not as a checklist but as prompts. When a conversation feels stuck, I’ll reach for one to help unlock new thinking. When a decision feels rushed, I’ll use them to slow down the process and surface what might otherwise go unsaid.

The key is not only to ask these questions but also to listen deeply to the answers. Too often, we ask out of habit rather than genuine interest. True curiosity requires patience, humility, and a willingness to follow the thread wherever it leads.

Summary 

In a world of rapid change, curiosity is no longer optional for leaders; it’s more important than ever. Organizations that value curiosity are better equipped to adapt, innovate, and thrive. Leaders who model curiosity encourage their teams to engage in continuous learning, challenge the status quo, and embrace complexity.

By practicing curiosity, we do more than sharpen our leadership skills. We create a culture where deeper questions are welcomed and celebrated. And in that culture, we find the insights, innovations, and connections that help us meet the challenges of today and prepare for those of tomorrow – a big thanks to Diane Hamilton for her impressive work in this area.

Written by Leo Bottary. Have you read?
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