AI Retreat

A full day of hands-on AI work, on your campus, with your leadership team in one room

For a Retreat, a leader of the Association spends a full day on your campus, doing the actual, hands-on work alongside your leadership team. Your team works with AI in real time, in the same room, together.

If you have been meaning to get your senior leadership team grounded in AI and have not yet found the time, this day is built for you. The Retreat brings the Association for Academic Leaders to your campus for a working session designed around the leadership tasks your team actually does. By the end of the day, your senior leaders will share a common vocabulary, a working understanding of where Generative AI helps their work and where it does not, and a set of concrete prompts and use cases drawn from their actual responsibilities at your school.

The day is built for leadership teams who want to stop circling AI and start using it. We meet your team where they are. We assume no prior fluency, we keep the technical layer light, and we spend most of the day on real leadership tasks: drafting communications, preparing for difficult conversations, summarizing long documents, planning workshops, organizing notes from board meetings. Participants leave with prompts they have written, outputs they have refined, and a clearer sense of which tools fit which kinds of work.

What Your Team Will Take Away

  • A shared framework for thinking about AI as a Thought Partner, Executive Assistant, and Communications Coach, with examples grounded in independent school leadership

  • Hands-on practice with the major Generative AI tools (ChatGPT, Claude, Gemini, NotebookLM, Perplexity), including the prompting habits that separate weak output from useful output

  • A worked-use case from each participant's own portfolio, taken from start to refined draft during the day

  • A common language for talking about AI across your senior leadership team, so that future conversations start from shared ground

  • A set of three questions your team can apply when evaluating any AI tool: safety and privacy, usability, output quality

  • A short post-retreat memo from us summarizing what the team worked on and suggested next steps for your school

What to Expect

This is a working day, not a lecture. Participants bring a laptop, a real task they have been putting off, and a willingness to try. We bring the framework, the facilitation, and the experience of having run this work with leadership teams across the country.

Available exclusively to member schools of the Association for Academic Leaders.

Investment is $10,000 per Retreat, with our travel included. Up to 20 academic leaders from your school may participate; Retreats are designed for leadership teams, not for teachers.

Only nine Retreats are available this summer.

Inquire about a Retreat

If you are considering a Retreat for your team this summer, let's talk. Email us at members@academicleaders.org.