Questions That Cut Through the Fog: Using Curiosity to Navigate Ambiguity
A Leadership Reflection on the Curiosity Touchstone
There's a leadership moment many of us dread: the blank stare. You've asked for input on a strategic direction, and the response is so vague it could mean anything. "We just need to do better." "Let's improve our approach." "We should be more efficient."
Beneath that fog lies something deeper than lack of insight. Across client engagements, Crescent Leadership has identified a consistent pattern: ambiguity, more than workload, drives fatigue. Ambiguity drains mental energy because the brain struggles when goals and expectations are unclear. Team members are willing to extend extraordinary effort when they understand how their work aligns with mission outcomes. Curiosity restores agency.
Clear information matters. But clarity often begins not with more answers, but with better questions.
The Curiosity Touchstone Defined
In 9 Leader Touchstones, Dr. Jes DeShields defines curiosity as "the insatiable desire to know and understand unfamiliar things and then to put wonder into action." This isn't idle questioning or performative interest. It's the foundational practice that drives learning, innovation, and genuine connection with team members.
Curiosity is foundational to Leader-First® Leadership because it precedes and enables all other touchstones. Curiosity compels us to test our assumptions before acting on them. Without genuine curiosity, empathy becomes assumption. Authenticity becomes performance. Courage becomes recklessness.
But here's what most leaders miss: curiosity doesn't eliminate ambiguity. It transforms ambiguity from a source of paralysis into a pathway forward.
When Questions Create Possibility
Consider how partnerships form in the business world. Often, the most transformative relationships begin with a simple question asked without an agenda.
I experienced this firsthand during a vacation when I casually mentioned my background in hospitality to a local expert. His response: "You could return to that field. We could work together", planted a seed I hadn't considered. The next day, I approached the conversation differently: "Let's explore this idea. Here are my thoughts..."
What unfolded wasn't an interrogation or a formal pitch. It was genuine curiosity about the possibility from both sides. We discovered extraordinary alignment in values and vision, not because either of us had all the answers, but because we were both willing to ask questions when we genuinely didn't know.
That partnership became the foundation of my current business. But the transformation happened because curiosity created space for authentic exploration rather than predetermined outcomes.
Questions That Help vs. Questions That Hurt
As leaders, we ask questions constantly. But not all questions serve the same purpose, and the difference between helpful and harmful curiosity often comes down to intent. Consider a common scenario: A project deadline has been missed, and you need to understand what happened. Two leaders might approach this moment very differently.
Leader A asks:
"Why didn't you finish this on time?"
"Didn't you know this was a priority?"
"What were you doing instead of working on this?"
"Who else dropped the ball here?"
Leader B asks:
"What obstacles did you encounter?"
"What would have needed to be different for you to meet the deadline?"
"What support were you missing?"
"What can we learn from this for next time?"
Both leaders are seeking information about the same situation. But Leader A's questions feel like an interrogation designed to assign blame. They increase anxiety, signal distrust, and make the team member defensive. Even if Leader A genuinely wants to understand, the questions themselves create barriers to honest communication.
Leader B's questions, by contrast, open pathways to understanding. They acknowledge complexity, create psychological safety for honest responses, and demonstrate genuine interest in solving the problem rather than punishing the person. The distinction between helpful and harmful curiosity is whether you're genuinely seeking to understand or engaging in curiosity while pushing your own agenda.
Helpful curiosity:
Opens pathways to understanding
Creates psychological safety for honest responses
Acknowledges complexity without demanding immediate answers
Demonstrates genuine interest in others' perspectives
Harmful questioning:
Feels like interrogation or gotcha moments
Increases anxiety through implied criticism
Signals a lack of trust in those being questioned
Pushes toward predetermined solutions while pretending to be open
Creating Space for Team Questions
One of the most important applications of curiosity as a leadership practice is creating space for team members to ask their own clarifying questions.
My business partner, Anthony, models this brilliantly in his work. He asks constant questions of the people he serves: How are you feeling? What caught your attention? What would make tomorrow better? He's not gathering data to check boxes. Anthony is genuinely curious about each person's experience, using that information to adapt in real time.
This approach requires courage, another touchstone that pairs naturally with curiosity. Asking questions when you don't have the answers feels vulnerable. But that vulnerability creates trust. People know you're genuinely interested in co-creating optimal outcomes.
Research on decision-making and trust consistently shows that frameworks specifying who decides what, on what basis, and within what timeline sustain momentum and reinforce trust. But before you can create those frameworks, you need clarity about what's creating fog.
Practical Questions for Leaders
To practice Curiosity as a leadership tool this week, try asking your team (or yourself) these questions:
What's unclear right now that's making it hard to move forward?
What would you need to know to make this decision with confidence?
What assumptions are we making that we should test?
Who has information we're missing?
What would make this easier?
Notice these aren't yes/no questions. They don't have obvious right answers. They require genuine curiosity and a willingness to hear responses you didn't anticipate. If clarity depends solely on a leader’s temperament, it disappears the moment pressure rises. Curiosity becomes truly transformative when it moves beyond personality and into systemized practice. Ask:
How will we institutionalize better questions?
Where in our routines do we intentionally surface ambiguity?
What structures ensure that curiosity is not optional, but expected?
This might look like dedicated “clarity rounds” in team meetings, where the only agenda is identifying what feels unclear. It might mean creating decision frameworks that specify who decides what, on what basis, and within what timeline. In high-reliability environments, it can even resemble a “stop-the-line” norm, where anyone can raise a question without fear of repercussion.
Curiosity strengthens culture when it becomes a shared discipline rather than just a personal virtue.
Putting Wonder Into Action
The Curiosity Touchstone isn't complete until wonder transforms into action. Asking better questions matters, but what you do with the answers matters more.
When team members tell you what's creating ambiguity, don't just acknowledge it. Use that information to build clearer frameworks. When experts identify gaps in your approach, don't just agree, take action to address them. When your own questions reveal blind spots, don't just make a mental note—change your behavior.
This is where Curiosity reinforces every other Leader Touchstone:
Courage: Asking the hard questions everyone is avoiding
Emotional Intelligence: Reading when questions help versus overwhelm
Integrity: Asking clarifying questions about commitments so you can deliver on what you promise
Authenticity: Being willing to admit what you don't know
Empathy: Understanding what confusion feels like for your team
Inclusivity: Actively inviting perspectives that challenge your own
Gratitude: Valuing the insight others offer and acknowledging the learning that emerges from exploration
Resilience: Using learning and reflection to renew your mental and emotional energy
The Ambiguity-Fatigue Connection
Leaders often try to solve ambiguity by providing more information, clearer directives, or detailed documentation. But the most effective tool for cutting through fog is asking better questions, both of yourself and your team. Curiosity, when practiced with skill and empathy, transforms ambiguity from a source of exhaustion into a catalyst for clarity and alignment. It acknowledges that you don't have all the answers while demonstrating your commitment to finding them together.
Team members don't need you to eliminate all uncertainty. They need you to help them understand what matters, what the decision-making framework looks like, and how their work connects to mission outcomes. Good questions create that clarity in ways that mandates never can.
Your Reflection Questions
As you consider how curiosity might transform your approach to ambiguity and leadership:
Where might you be creating ambiguity for your team without realizing it?
What questions could you ask this week that would create more clarity?
How might curiosity change your relationship with uncertainty?
When has someone's genuine curiosity helped you gain clarity, and what made their questions effective?
Are you asking questions to genuinely understand, or to lead people toward your predetermined solution?
Curiosity does not remove uncertainty. It gives leaders the courage and discipline to walk into it. The questions can paralyze us or become the catalyst for deeper understanding and stronger alignment.