Dear Change Leader,
“I think I’ve been asking the wrong questions,” Sarah confided during our coaching session last week.
As VP of Operations for a mid-sized company, Sarah had been struggling with an impossible challenge: her team consistently missed deadlines despite working long hours. For months, she’d focused on one question: “How can we get this work done faster?”
She’d implemented new software, reorganized workflows, even brought in temporary staff. Nothing worked.
Then during a team meeting, someone said: “We’re always putting out fires instead of preventing them.”
That comment stopped Sarah cold. She realized her leadership mindset had been so focused on speed that she’d never asked: “What’s creating these urgent situations in the first place?”
This shift in leadership questions opened an entirely different conversation. Within two weeks, her team identified three patterns generating unnecessary urgency. Within a month, they’d addressed underlying causes and were meeting deadlines–all while working more sustainable hours.
The Power of Different Questions
Sarah’s breakthrough illustrates something we often overlook in change leadership: the questions we ask shape not just the answers we get, but the entire reality we see.
When we’re under pressure, we default to familiar thinking patterns. Our mental models—those unconscious frameworks we use to make sense of the world—can become both assets and blind spots.
The challenge isn’t that our existing mindsets are wrong. They’ve likely served us well. The problem comes when we apply them without question to new, complex, or rapidly changing circumstances.
Why Leadership Questions Matter Now
In today’s environment of constant disruption, the ability to question assumptions isn’t just helpful—it’s essential. The strategies that worked six months ago may not work today. The problems you’re solving may not even be the right problems.
Yet most of us have been trained to have answers, not ask questions. We’ve been rewarded for certainty, not curiosity. As leaders, we feel pressure to project confidence and direction.
But what if some of our greatest leadership moments come not from having all the answers, but from developing a curious leadership approach?
Three Types of Questions That Open New Possibilities
As you navigate complexity in your organization, consider incorporating these questioning techniques into your leadership development:
1. Assumption-Testing Questions
These help surface beliefs you’re taking for granted:
- “What are we assuming to be true about this situation?”
- “If our biggest assumption turned out to be wrong, what would change?”
- “What would someone outside our industry see that we’re missing?”
2. Perspective-Expanding Questions
These invite multiple viewpoints and challenge your initial framing:
- “Who else is affected that we haven’t heard from?”
- “How might our biggest critic describe this situation?”
- “What would this look like as an opportunity rather than a problem?”
3. System-Revealing Questions
These help you see larger patterns and connections:
- “What patterns keep recurring that we treat as isolated incidents?”
- “Where else might this same challenge be showing up?”
- “What would happen if we stopped our current solution for two weeks?”
The goal isn’t perfect answers immediately. It’s creating space for new insights to emerge.
Three Practices for the Week Ahead
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Team Meeting Assumption Check
In your next leadership meeting, spend 10 minutes on one current challenge. Ask: “What assumptions are we making that we haven’t questioned recently?” Write them down without immediate solutions.
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Stakeholder Perspective Conversations
Choose one pending decision. Have 15-minute conversations with three people who’ll be affected but represent different viewpoints. Ask: “What concerns or opportunities might I not be seeing?”
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Daily Question Journal
For one week, end each day writing one question about your work that you didn’t have time to explore. Review patterns at week’s end.
Moving Forward with Confident Curiosity
The most effective leaders in change management share a trait: they’re as curious about their own thinking as they are about the problems they’re solving.
This doesn’t mean second-guessing every decision. It means developing “confident curiosity”—moving forward decisively while remaining open to information that might change your course.
In uncertain times, your willingness to question your leadership mindset may be your most valuable tool.
Pay attention to what happens when you approach your current challenges not just as problems to solve, but as opportunities to discover what you don’t yet know.
P.S. Which type of question—assumption-testing, perspective-expanding, or system-revealing—feels most relevant to a challenge you’re facing? Hit reply and let me know.
Real Leadership in Action: When Questions Transform Organizations
What happens when a leader inherits an organization where eight leaders have failed in four years? This is what my client Sarah faced when she stepped into leadership at a national nonprofit in crisis.
“I had a matter of weeks to build a team and create momentum,” Sarah explained. “The board needed results quickly, but the constant leadership turnover had left deep organizational scars.”
Instead of asking the obvious question—”How do I fix this quickly?”—Sarah learned to ask different questions: “What patterns created this cycle of failure?” and “How might we build something sustainable rather than just urgent?”
The result? Within a year, her leadership team transformed from isolated individuals into a high-functioning unit that secured significant federal grants, developed new partnerships, and—most importantly—broke the cycle of leadership turnover.
Want to see how Sarah’s questioning approach created lasting change? [Learn more about her story and discover the specific leadership questions that made the difference →]
Sometimes the most powerful leadership transformations begin not with having better answers, but with asking fundamentally different questions. Sarah’s story shows how curiosity can rebuild what certainty couldn’t fix.
EFFECTIVE CHANGE RESULTS FROM INTENTIONAL LEADERSHIP
We’re a leadership and organization development consultancy. My team and I work with leaders like you to prepare for and lead successful change processes.
Here’s why our clients call us:
- Leadership Coaching: I support leaders as they navigate transitions into new roles or expanded responsibilities.
- Group Coaching and Learning Programs: Bringing groups of leaders together, I facilitate learning experiences and months-long programs that equip people to be effective change leaders.
- Effective Teams and Stronger Organizations: I work with leaders and their teams with tailored processes that increase their effectiveness, building layers of aligned teams that transform organizations.