5.5: Case Study

Chapter 5 Case Study: When the System Cannot Speak for Itself

Dr. Maya Thompson entered her sixth year as superintendent of Prairie View School District with a clearer sense of the territory. The evaluation system redesign of her early years was holding. The professional development system was significantly more differentiated and connected to individual principal goals. Her Evaluator Cohort was calibrated and meeting regularly. By most measurable indicators, Prairie View was functioning as a growth-oriented leadership system.

Yet, Dr. Thompson had learned to be attentive to what metrics did not capture. As her sixth year unfolded, she noticed something in the district’s leadership culture that no evaluation cycle could address: the conversations that were not happening.

The first sign came during a fall principals’ cabinet meeting. Dr. Thompson introduced a proposal to pilot artificial intelligence tools in instructional planning at three volunteer schools. The presentation was met with polite nodding. No one asked a substantive question. No one pushed back. The meeting ended in twenty minutes.

What followed told a different story. In the weeks after the meeting, Dr. Thompson began hearing that there was significant concern among the cabinet about the AI initiative. Teachers were already anxious. Some principals felt the rollout was too fast. One principal, Marcus Webb, had apparently been telling his staff that the initiative was “not going to survive the spring.”

She pulled Marcus’s evaluation record. His ratings were consistently proficient. His coaching conversations were collegial. On paper, there was nothing to address. But the gap between what was said in the cabinet meeting and what was said outside of it was widening. Dr. Thompson recognized a culture where difficult conversations were happening everywhere except in the room where they needed to happen.

The Challenge

Dr. Thompson scheduled a one-on-one with Marcus. She arrived with a different intention than she usually brought to these meetings. She had spent the previous evening reviewing Ringer’s (2013) preparation checklist. She wrote down her own emotional response: a sense of being undermined. She examined that feeling carefully. Was she certain the third-hand account was accurate? No. Had she given Marcus a genuine opportunity to raise his concerns directly? She wasn’t sure.

She began with inquiry. She asked Marcus how his staff was experiencing the beginning of the year and listened carefully. When she asked specifically what he was hearing about the AI pilot, the room shifted. Marcus was quiet, then said what he had been carrying for weeks: his teachers were exhausted. They had absorbed three years of post-pandemic recovery initiatives, a new literacy curriculum, and a revised teacher evaluation framework. The AI tools felt like one more thing. He had not known how to say that in the cabinet meeting without appearing resistant.

Dr. Thompson acknowledged what she heard without minimizing her commitment to the initiative or Marcus’s legitimate concern. She named the emotional dynamic directly: “I think we’ve built a cabinet culture where people are more comfortable disagreeing with me in the hallway than in the meeting, and I want to understand why that is.” Marcus did not immediately have a full answer, but the conversation opened a space that previous formal meetings had not.

What Changed

Over the next month, Dr. Thompson made two structural changes and one relational one. Structurally, she revised the AI pilot timeline to allow schools to determine their own entry points. She also added a standing agenda item to cabinet meetings: fifteen minutes for “unfinished business,” explicitly protected time for concerns not raised earlier.

The relational change was more fundamental. Dr. Thompson began her next cabinet meeting by sharing what she had learned from her conversation with Marcus—not its contents, but its shape. She told her principals she had discovered a gap between conversations happening inside and outside the room. She took responsibility for her role in creating that gap. She named the dynamic Ringer (2013) calls the “culture of avoidance”: the tendency to route difficult truths away from the people who most need to hear them.

The response was not immediate. But in subsequent months, the quality of cabinet conversations shifted. People began raising concerns in the meeting rather than after it. Marcus became one of the more candid voices in the room.

Prairie View’s evaluation systems and professional development structures remained intact. But Dr. Thompson understood the limits of well-designed systems: they create the conditions in which courageous conversations are possible. They do not have courageous conversations. That work belongs to leaders who do the internal preparation, enter the room with genuine curiosity, and stay present long enough for the truth to be said.

Discussion Questions

1. Dr. Thompson identifies a gap between what is said in formal meetings and what circulates informally. What organizational and relational conditions produce this kind of culture of avoidance, and what is a superintendent’s responsibility for shaping it?
2. How did Dr. Thompson’s internal preparation before meeting with Marcus reflect the EI principles described in this chapter? What might the conversation have looked like if she had entered reactively rather than reflectively?
3. Dr. Thompson chooses to share what she learned from her conversation with Marcus at the next cabinet meeting—not its contents, but its shape. What are the risks and benefits of a superintendent modeling this kind of public self-reflection with their principals?
4. The case distinguishes between structural changes (revised timeline, new agenda item) and a relational change (naming the culture of avoidance). Which do you think mattered more, and why?
5. The case ends with the observation that well-designed systems create conditions for courageous conversations but do not have them. How does this frame the relationship between the structural work of the superintendent and the relational work?