One of the quiet surprises of leadership is that experience doesn’t necessarily make the work feel easier. It changes the kinds of questions we ask.
Early in our careers, confidence often comes from finding the right answer. We study best practices, seek advice from trusted mentors, and celebrate the moments when our decisions produce the outcomes we hoped for. Every success reinforces the belief that with enough experience, leadership will eventually become more predictable.
Over time, our understanding begins to change. We become more aware of the complexity surrounding decisions that once seemed straightforward. We recognize perspectives we might have overlooked earlier in our careers and consequences that aren’t always immediately visible. Solutions that worked beautifully one year produce different results the next.
Experience helps us recognize patterns and anticipate challenges. It also teaches us that familiar situations can contain important differences. The longer we lead, the more we discover how much there still is to understand.
I’ve noticed this in some of the most effective leaders I’ve known. Their experience gives them confidence in their judgment, but it also makes them more curious about what they might be missing.
They ask questions because they’ve learned that their first understanding of a situation, however informed, may be incomplete. They trust their ability to make decisions while remaining willing to reconsider their assumptions.
Instead of asking, “How do I get people to see what I see?” they begin asking, “What am I not seeing yet?”
That subtle shift matters because one of the greatest risks of experience isn’t simply becoming overconfident. It’s becoming overly certain.
Confidence allows us to make decisions when information is incomplete. But experience can also make us overly certain, especially when we’ve encountered similar situations before and believe we know what to expect. That certainty can quietly limit what we’re willing to learn.
Consider a principal introducing a new instructional initiative. The work has been thoughtfully developed, grounded in research, and connected to the school’s improvement priorities. During a conversation, an experienced teacher raises concerns about the proposed direction. The principal believes in the initiative and wants to move the work forward, but recognizes there may be something worth understanding in the teacher’s response.
The principal could explain the rationale or clarify expectations. Both may eventually be necessary. But beginning with an explanation could mean missing an opportunity to better understand the concern.
What if the principal began by asking, “Help me understand what concerns you about this approach?”
In seeking to understand, the principal might discover that the teacher actually supports the instructional goal but sees a scheduling conflict that could make implementation difficult. Perhaps the professional learning hasn’t adequately prepared staff for what’s being asked of them. Or the concern may reflect a genuine disagreement about the direction itself.
What emerges from that conversation may lead to adjustments in timing, additional support, or greater clarity about expectations. It may also reinforce the original decision. Listening carefully doesn’t obligate a leader to accommodate every concern, and some decisions will remain unpopular even after people have been heard.
Still, understanding the concern gives the principal a better basis for deciding how to proceed. It can also help distinguish between disagreement with the goal and difficulties with the conditions needed to achieve it.
I’ve seen how easily we can interpret a response through the lens of what we already believe. A parent questions a long-standing procedure. Student data challenges our expectations. Staff members respond to a decision differently than we anticipated. In each case, our initial interpretation may be reasonable, but there may be more to understand.
Curiosity helps us examine those interpretations before they harden into conclusions. It creates opportunities to recognize how decisions are experienced by others and whether our assumptions reflect what’s actually happening.
Of course, school leaders rarely have the luxury of exploring every perspective indefinitely. Decisions often involve competing priorities, incomplete information, and real deadlines. Experience helps us recognize when additional inquiry is worthwhile, what information matters, and when it’s time to act.
The leaders I most respect are comfortable making difficult decisions while remaining open to what those decisions reveal. They recognize that learning continues through implementation, as new information emerges and the realities of practice become clearer. They’re willing to revisit assumptions, make adjustments, and adapt their approach while remaining grounded in the purpose behind the decision.
With Thanksgiving approaching, I’ve been thinking about the people who have helped me see things differently over the years. Some challenged my assumptions. Others shared experiences that revealed something I hadn’t considered. I’m especially grateful for the students, teachers, families, and colleagues whose perspectives have shaped my understanding of leadership, often in ways I didn’t fully appreciate at the time. Their perspectives have reminded me that understanding a school requires listening to the people who experience it every day.
A Leadership Practice
The next time someone challenges one of your ideas, try asking one genuine question before explaining your position.
It might be as simple as, “Help me understand what concerns you most about this,” or “What am I overlooking that could affect how this works?”
Listen for something that might challenge your initial interpretation. Consider whether what you’ve learned changes the decision, suggests a different approach to implementation, or simply gives you a better understanding of the concern.
You may discover that your original decision remains the right one. You may also uncover an adjustment that improves the likelihood of success. Either way, you’ve taken an intentional step toward understanding the people and conditions your decision will affect.
Curiosity doesn’t require abandoning conviction. It requires enough humility to recognize that even well-informed judgments can benefit from another perspective.
Leadership requires confidence. People need principals and assistant principals who can provide direction, make decisions, and move important work forward. Experience strengthens that capacity, especially when we remain willing to learn from the people and circumstances around us.
Confidence moves people forward. Curiosity helps ensure the direction is worth following.