Five Strategic AI Moves School Leaders Should Make This Year

Tim Dasey

Sweet Graipes

Aug 6, 2025

Summary for Educators: “Five Strategic AI Moves School Leaders Should Make This Year” by Tim Dasey Published August 6, 2025 | Source: https://sweetgraipes.substack.com/p/five-strategic-ai-moves-school-...

As AI technology reshapes education at an unprecedented pace, school leaders face mounting pressure to guide their districts with clarity and urgency. In his article, Tim Dasey lays out five pragmatic, forward-thinking moves that educational leaders can take to strategically integrate AI in schools, without waiting for policy perfection or full understanding.

1. Position AI as a Major Educational Shift

Dasey urges school leaders to clearly communicate to all stakeholders—students, staff, and parents—that AI is not a fleeting ed-tech trend but a transformational force. Leaders must treat AI as central to the future of work and learning, not as an optional add-on. Ignoring AI, he says, would amount to educational malpractice.

This shift in messaging changes the nature of conversation. Instead of debating whether AI belongs in schools, the dialogue becomes about how to integrate it effectively and equitably. Leaders are encouraged to personally explore AI tools to stay informed and lead from experience rather than speculation.

2. Build Peer Learning Communities With Purpose

Teachers need structured time to learn and collaborate around AI integration. Dasey proposes AI peer learning communities that have clear goals: understanding AI’s educational value, aligning AI use with instructional goals, and developing concrete strategies to help students use AI responsibly.

Rather than waiting for teachers to become AI experts, the focus should be on co-exploration—developing the ability to engage in meaningful discussions with students about AI's uses and limits. These learning groups should produce practical outcomes such as AI-aware lesson plans, modified assessments, and classroom norms for AI use.

Leaders should also empower early adopters to mentor colleagues, share classroom-tested ideas, and build internal capacity across departments.

3. Turn Resistance Into Reflective Evaluation

Rather than suppressing teachers' emotional responses to AI—fear, skepticism, or excitement—leaders should channel them into productive analysis. Skeptics, for instance, can serve as quality control agents by developing evaluation criteria for AI tools.

Dasey also debunks the myth that AI education requires screens or tech skills. He encourages leaders to show how AI concepts—like intelligence, decision-making, and bias—can be taught through discussion and reflection, in any subject. Co-learning, making thinking visible, and strategic permissions for AI use are key to balancing innovation and caution.

4. Adopt Agile Strategy Cycles

Traditional planning models are too slow for today’s rapid AI evolution, while crisis-mode reactions are too chaotic. Dasey calls for iterative AI strategy cycles—small, recurring meetings with cross-functional teams to assess what's working, what’s emerging, and what needs adjusting.

This agile approach embeds responsiveness into the school’s culture. Teams should review classroom practices, student outcomes, new AI capabilities, and evolving policy needs. The goal is institutional agility, not perfection. Shared learning across districts can further accelerate innovation and prevent duplication of effort.

5. Measure Progress by Implementation, Not Just Test Scores

Current metrics fail to capture the kinds of thinking and collaboration needed in an AI-literate society. Instead, leaders should track indicators of implementation: Are teachers co-learning with students? Are they explaining their thinking processes? Are they using AI to design learning activities that weren’t possible before?

Operationally, AI can help with scheduling, communications, and curriculum analysis. But Dasey stresses that the most critical questions are whether teachers and students are adapting their practices—not how many tools were bought or how many hours of PD were logged.

Conclusion

Dasey’s five strategic moves provide a roadmap for school leaders to embrace AI with purpose. Rather than being paralyzed by uncertainty or chasing trends, leaders can create a culture of curiosity, experimentation, and reflection. The central message: AI isn't waiting, and neither should schools. Strategic adaptation is the key to preparing students—and educators—for an AI-rich future.

Original Article

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Prepared with the assistance of AI software

OpenAI. (2025). ChatGPT (4) [Large language model]. https://chat.openai.com