By Jessica Schuler
School principals juggle emails, schedules, meetings, classroom observations, data analysis and parent communication every day. Each administrative task competes with time spent supporting teachers and students.
Hillsborough County Public Schools (HCPS) in west-central Florida saw an opportunity to use artificial intelligence (AI) not simply to increase productivity, but to help school leaders reclaim time for instructional leadership.
That vision led HCPS to partner with Microsoft and the Northwest Council for Computer Education (NCCE) to help principals and assistant principals put Microsoft 365 Copilot to work solving the everyday challenges of school leadership.
From Experimenting with AI to Using It With Purpose
Many administrators across the district had already experimented with AI and understood how to use it in a general sense; what they needed was help using it within their existing work.
The district saw an opportunity for structured training built specifically around the work school leaders were already doing. Rather than simply teaching principals about AI, the goal was to help them use tools within Microsoft 365 to solve real leadership challenges. By leveraging tools they already used everyday within Microsoft 365, administrators could explore AI on an approved platform while maintaining established expectations around data privacy, security, and responsible use.
“We wanted to provide leaders with tools that help create more time in their day so they can focus on their role as instructional leaders while streamlining everyday tasks,” said Chris Holt, the supervisor of technology training for HCPS.
Designing Professional Learning Around Real Work
HCPS already had a relationship with NCCE and saw the similar work the organization was doing with Broward County Public Schools around Copilot.
In partnership with Microsoft, NCCE provided a series of five 90-minute virtual training sessions for principals on how to use Copilot within Microsoft 365 apps. The sessions were designed around real administrator responsibilities rather than as generic AI demonstrations. Activities included:
- Drafting and refining staff and family communications with Copilot in Microsoft Outlook.
- Turning classroom walkthrough observation notes into evidence-based feedback using Copilot in Microsoft Word.
- Analyzing student progress and intervention data using Copilot in Microsoft Excel.
- Building professional development presentations from outlines, goals, and district data using Copilot in Microsoft PowerPoint.
- Working through realistic leadership scenarios such as school improvement planning, faculty meeting preparation, community communication, and data-driven decision making.
Each session was delivered following the “I Do, We Do, You Do” model, which is designed to slowly shift the work from the teacher to the student—in this case, the school leaders. NCCE’s trainers first demonstrated how to do something with Copilot, then worked on an example together with the principals, and finally let the principals do it themselves.
“We saw so much growth,” said NCCE coordinator of professional learning Michael Higley, Ed.D. “I think the biggest thing that made it so successful wasn’t just the pacing of the session, but that the use case examples were very specific to what they’re doing in their workflows.”
After 60 minutes of direct instruction, the trainers were available for questions for the final 30 minutes. Administrators could choose to stay on the call and continue to practice with the trainers present to provide help if they ran into challenges.
The training was so successful, the district asked NCCE to adapt it for assistant principals, as well. In all, the project was designed to support more than 200 school administrators across the district.
“They took what we presented and immediately used it,” Dr. Higley said. “That wasn’t just observed by the trainers, but it was also reported by their leadership.”
Collaboration Becomes Part of the Model
Dr. Higley stressed that weekly touchpoint meetings between the district, NCCE, and Microsoft were crucial to the success of the project. Such deep collaboration is unusual, he said, as district leadership often does not have time to dedicate to more than a handful of meetings.
These touchpoint meetings gave the three parties a standing opportunity to fine-tune each session, debrief as the project went along, and adapt as needed. For example, early feedback after the first session emphasized moving more quickly into practical applications by reducing background content and increasing real-world examples and task-based activities.
“So we shortened introductory AI content, streamlined portions of the presentation, and focused more heavily on administrator workflows,” Dr. Higley said. “Future sessions were intentionally designed to be increasingly hands-on and tied to actual leadership responsibilities.”
The changes paid off. “Once sessions became more task-based, the district reported strong engagement and specifically asked for future trainings to remain hands-on and connected to real data and authentic leadership challenges,” he added.
While this was not the first time HCPS had worked with NCCE, Holt noted the value in the collaborative partnership. Rather than telling the district what should be done or repeating what had been done elsewhere, NCCE “listened to the needs that we had in the district,” he said. “There was a true level of what’s going to fit our district and the work we’re doing right now.”
Dr. Higley noted: “The real success came from aligning training, leadership support, and practical application around a common goal.”
Relevant Learning Drives Organic Adoption
The adjustments resonated with the school leaders. Participation grew throughout the series as principals encouraged their colleagues to attend future sessions. Holt said about 40 principals signed up initially, but later sessions drew as many as 75-80 participants.
“It means they’re seeing value in it,” Holt said.
The engagement extended beyond attendance. Holt noted that discussions in the chat were robust, with principals sharing examples, asking questions, and bringing ideas they had explored back to the group.
“You could tell that principals were thinking about things between sessions and bringing them to the next one,” he said.
The peer-to-peer exchange became another indicator that the training was taking hold. Principals began sharing ideas with one another outside the sessions, and some eventually presented to other principals about how they were using AI in their work.
The response from the principals also helped drive the next phase of the initiative. As the training progressed, principals began asking whether their assistant principals could participate as well, prompting HCPS and NCCE to offer a second cohort tailored to assistant principals.
Beyond Productivity
Hillsborough school leaders quickly connected Copilot to time-saving opportunities in their daily work. “The shift from asking, ‘What is AI?’ to asking, ‘Can Copilot help me with this?’ was noticeable as sessions progressed,” Dr. Higley observed.
The principals began using Copilot to triage emails faster, assist with scheduling, and provide more timely feedback on classroom observations. By streamlining these tasks, they could spend more time on instructional leadership, including coaching and supporting teachers.
As administrators have continued using AI beyond the training series, some have begun exploring more advanced applications, including custom agents for recurring leadership tasks. Several principals, for example, have developed agents related to student behavior and the district’s Code of Conduct, while others have explored using AI to assist with master scheduling.
Administrators are also beginning to explore agents that could support classroom observation and feedback. These tools can incorporate district resources and instructional frameworks to help summarize notes from classroom observations and generate a starting point for feedback. Administrators then review and refine the output to ensure it accurately reflects what they observed and aligns with their professional judgment.
For Holt, these more advanced applications represent an important evolution in how the district thinks about AI. Productivity is an important starting point, but the larger opportunity is using AI to support increasingly complex work.
“When I’ve talked to people that have started to use it more and more, the same thing keeps coming up: It gives them more time to be an instructional leader,” he said.
Looking Ahead
The initial Copilot training is just the beginning for HCPS. The district plans to continue supporting administrators as they gain access to the platform and explore increasingly advanced applications of AI.
Custom agents are emerging as a particular area of interest. Some administrators are already experimenting with agents that can support behavior management and instructional feedback, and Holt expects that work to continue as the school year begins and school leaders become more comfortable with the technology.
The district also plans to continue monitoring how administrators use Copilot and evaluating whether the technology is delivering value. For Holt, that means looking beyond a one-time professional learning experience to ensure that AI becomes a sustainable part of how leaders work.
“It’s not just a one-and-done training,” he said. “How are we continuing to reinforce that to understand how it’s being used? How are we looking at data to make sure we’re getting value for our money out of those platforms?”
As HCPS moves forward, the focus will increasingly shift from using AI to complete routine tasks to applying it to more complex work, including data analysis and other forms of leadership and instructional support.
“Productivity is the initial step into the use of AI,” Holt said. “I think the next phase is, how do we start using it in more advanced ways that can have a clear impact on student achievement?”
For Hillsborough’s school leaders, the value of Copilot is increasingly showing up in the time it gives back. As administrators find new ways to use the technology, they are finding more room in their days for the work that drew them to school leadership in the first place: supporting teachers and helping students succeed.