Early in my leadership career as a principal, I often engaged with teachers or staff members who made a poor choice or missed a deadline in a rather authoritative manner. My default was to open with questions like “Why did you do that?” or “Why isn’t this finished yet?” Those questions immediately put people on the defensive and rarely led to good outcomes.
One moment I’ll never forget was when I asked a teacher why I saw her driving away from campus before the school day was complete. She told me she had a meeting across town, which I then called to verify. She was deeply offended that I would “check up on her” rather than trusting her word. That one choice created unnecessary damage to our relationship. Had I simply asked another question or two—about what she had going on, or what she needed from me—I could have found Clarity without sacrificing trust.
That experience taught me an important lesson: school leaders must resist the temptation to stop at the first question. Asking the extra questions builds clarity, strengthens trust, and creates the foundation for healthier school culture.
When a teacher misses a deadline, a student incident isn’t handled the way we’d hoped, or a staff member leaves us frustrated, the instinct is to ask one quick question: “Why did this happen?” or “What went wrong?”
But those first questions rarely provide insight. More often, they create defensiveness. If we stop there, we leave with assumptions instead of clarity—and sometimes with Relationships strained in the process.
Asking the extra questions communicates curiosity instead of accusation. It tells teachers and staff: “I want to understand, not just judge.”
For school leaders, this is critical. We often don’t see the whole picture of what our staff are juggling—student needs, parent concerns, resource limitations, or personal challenges. The extra questions uncover whether the issue is about clarity of expectations, lack of support, or barriers outside of the teacher’s control. And they show our staff that we’re invested in their success.
Clarify Context
“Can you walk me through what happened in class before this?”
“What factors influenced how you handled the situation?”
Explore Resources & Support
“What tools or strategies did you have available?”
“What support might have made this easier for you?”
Dig Into Process
“How did you decide to approach the lesson this way?”
“Where did it start to feel challenging?”
Uncover Barriers
“What obstacles got in the way?”
“What was harder than you expected?”
Connect Back to Expectations
“What’s your understanding of the expectation here?”
“What does success in this situation look like to you?”
Look Forward, Not Just Back
“What’s one adjustment you’d make next time?”
“What support from me would help you move forward successfully?”
When principals and school leaders commit to asking the extra questions, three powerful things happen:
Trust grows. Teachers feel respected, seen, and valued.
Clarity emerges. Leaders learn whether the issue is a misunderstanding, lack of support, or systemic barrier.
Solutions surface. Conversations shift from “what went wrong” to “how can we do this better for our students next time?”
This is how strong school cultures are built—through curiosity, trust, and a commitment to Growth.
Our job as school leaders isn’t to catch staff in mistakes; it’s to help them grow and succeed. That requires listening, patience, and asking just one more question than feels natural.
So the next time you face a difficult conversation with a teacher or staff member, pause before you make assumptions. Ask the extra questions. You may be surprised at what you discover—and at how much stronger your school culture becomes when you choose curiosity over judgment.
If you and your leadership team are struggling with these kinds of conversations, you don’t have to figure it out alone. This is the work I do every day with principals, assistant principals, and district leaders—helping them find clarity, build trust, and strengthen the culture in their schools. If you’d like to explore how I can support you or your team, let’s connect for a conversation, or consider bringing me in to work alongside your leaders. Together, we can develop the skills and habits of asking the extra questions that lead to stronger relationships, healthier culture, and better outcomes for students.
Tune in this Sunday to “Leaning into Leadership” when I sit down with Dr. Jason Williamson to talk about his focus on Second Mile Leadership.
