8 Things I Learned at the Educators AI Playbook LIVE

As the premier supporting partner of the Educators AI Playbook LIVE, Veracross is proud to help bring this conversation to independent school leaders, and excited to be at the forefront of it alongside 9ine. The Educators AI Playbook started as a monthly, one-hour digital briefing hosted by Mark Orchison (CEO, 9ine) and Dan Fitzpatrick (The AI Educator) — a concise, practical digest of the month’s most critical AI updates, legislative changes, and tool breakthroughs.

In April 2026, that webinar series made its debut as a full-day, in-person conference. The event brought together school leaders, AI practitioners, accreditation bodies, and executives from Google and Microsoft at the United Nations International School in New York City to have the kind of honest, substantive conversation about AI that most conferences still aren’t having.

Here are the eight takeaways that stuck with me most.

1. There’s a big difference between schools that are keeping up and leading forward.

Dan Fitzpatrick, the AI Educator, one of the day’s keynote speakers, put it plainly: AI is not a trend that schools can afford to observe from a safe distance. Decision paralysis (waiting for government guidance, watching to see what other schools do first) is itself a choice, and not a neutral one. Schools that move thoughtfully now will be far better positioned than those who hold out for certainty that may never come. The message wasn’t “go fast,” it was “go forward.”

2. “This is the first time we’ve ever had technology that speaks our language.”

Dan opened his keynote with this impactful line that really flipped the way educators should be thinking about AI. Think about every other major technology shift in education — computers, the internet, smartphones, learning management systems. Every single one required people to adapt to the tool. You had to learn the interface, the syntax, the workflow. The technology set the terms, and humans adjusted. AI flips that. It meets you where you are. You can interact with it in plain English, ask follow-up questions the way you would in a conversation, and get something useful back without any technical training.

That’s what makes this moment genuinely different, and why the bar for entry has never been lower. A teacher doesn’t need to know how to code to use AI to draft a rubric, summarize a report, or build a lesson plan. A business officer doesn’t need an IT background to query a dataset or generate a draft policy. The tools are accessible in a way that previous technologies simply weren’t, which means the potential user base is essentially everyone. This scale of accessibility is exactly why the conversation around thoughtful, intentional use needs to keep pace. However, that low barrier cuts both ways. The same accessibility that opens AI up to everyone also makes it easy to adopt without the intentionality these tools deserve.

3. Agentic AI is already here — and your students probably know about it.

Most of the AI tools schools have been grappling with so far are reactive. You give them a prompt, they give you a response. Agentic AI is a meaningful step beyond that. These systems don’t wait for instructions at every turn. You give them a goal, and they pursue it: making decisions, using tools, taking actions, and course-correcting along the way largely on their own. Think less “AI assistant” and more “AI that completes the task while you’re doing something else.”

For schools, that distinction matters more than it might sound. A student doesn’t just ask an AI to help them understand a topic. An agentic system could complete an entire assignment, navigate a learning portal, submit work, and cover its tracks, all from a single instruction. The assessment and academic integrity implications alone are significant, and schools that haven’t thought past ChatGPT-style tools are already working with an incomplete picture.

Then there’s the hardware side. AI wearables, like smart glasses that deliver real-time audio or visual information, are on the market and moving fast. The classroom implications are obvious: a student wearing a device that can quietly surface answers, translate text, or fact-check a teacher in real time creates a fundamentally different environment than the one most school policies were written for. These aren’t hypothetical future problems. The technology exists now, consumer versions are here, and schools will need to have considered their position before these devices start showing up in backpacks.

The throughline across all of it: your students are likely more aware of these tools than many of the adults in your building. That’s not a reason to panic — but it is a reason to get informed and get ahead of it.

4. The goal for AI in schools isn’t intelligence. It’s agency.

Dr. Sabba Quidwai offered what I thought was the most memorable reframes of the day. She challenged the assumption that the value of AI is what it knows. The real goal, she argued, is agency — for students, educators, and school communities. Knowing how a system influences you, and how you can influence it in return. Without that, AI remains something that happens to people rather than something people direct. Her work through Designing Schools is built on this idea, and it was a good reminder that the human-centered piece isn’t a soft add-on to an AI strategy. It’s the foundation.

5. The accreditation landscape is changing. Here’s what that means for your school.

ATLIS hosted a candid panel conversation with executives from WASC, NEASC, CAIS, and NJAIS. The throughline: if accreditation bodies don’t evolve alongside AI, they risk becoming irrelevant. One panelist said it plainly — there is no guarantee accreditation continues in its current form if schools and accreditors aren’t willing to change together. The question of how to define and measure “quality” in an AI-integrated school is genuinely open, and these leaders are actively working through it. Schools that are engaging thoughtfully with AI will be better positioned for that conversation and the accreditation in the future.

6. Vetting your EdTech vendors has never been more important.

There’s a lot of “AI-powered” products and solutions in the market right now. One of the lunch sessions I joined tackled the very real problem of distinguishing tools that are genuinely thoughtful about data privacy and student safety from those that are just using the language.

Both Google and Microsoft echoed the same thing in the afternoon: not everyone building “AI-powered” educational tools understands what they’re up against. Companies like Google and Microsoft have spent decades operating at scale — in schools, in regulated industries, in government contexts — which means they’ve had to build real, tested infrastructure around data privacy compliance, security protocols, and ethical use policies. Not necessarily because they wanted to, but because regulators, institutions, and users demanded it of them over time.

A newer EdTech startup with “AI-powered” in its pitch deck likely hasn’t been through any of that. They may have good intentions, but good intentions aren’t the same as FERPA compliance, clear data retention policies, or a transparent framework for how their model was trained. When you’re trying to figure out what responsible AI use actually looks like in practice, treat the standards set by the larger, established players as a starting benchmark. Not a rubber stamp, but a reference point worth using.

7. Cognitive offloading is a real concern — and the answer starts with teachers.

One question kept surfacing throughout the day: what happens to critical thinking when AI does the heavy lifting? Cognitive offloading refers to the tendency to outsource mental effort to an external tool rather than doing the thinking yourself. In everyday life, it’s relatively benign. We’ve been offloading to calculators, GPS, and spell-check for years. But in an educational context, where the whole point is to build critical thinking skills, the stakes are different. If a student uses AI to generate an essay rather than wrestle with the argument themselves, they may get a good grade and walk away having learned very little. The concern isn’t the output — it’s what gets skipped in the process of getting there.

In the EdTech space specifically, this is a design challenge as much as a policy one. Tools that simply produce answers on demand are easy to build and easy to misuse. The more interesting work, and the direction both Google and Microsoft signaled they’re investing in, is building tools that guide students through thinking rather than bypassing it entirely. Prompted reflection, scaffolded inquiry, questions that push back before giving an answer. The technology can be built either way; the question is whether the people buying and deploying it are asking for the right thing. That starts with educator literacy: teachers who understand how these tools work are far better positioned to deploy them in ways that build student capacity rather than quietly erode it.

8. If AI helps promote balance and efficiency in the workplace, why would education be exempt?

I kept coming back to this question posed by Christina Lewellen of ATLIS in her afternoon breakout session. So much of the AI conversation in schools is framed around students, academic integrity, AI detection, and what the classroom looks like. But the educator and administrator experience matters too. AI tools that reduce administrative load, streamline lesson planning, and give back time aren’t a distraction from good pedagogy. They create the conditions for it. That reframe felt important.

For teachers, the administrative weight that accumulates alongside classroom work is often where the energy drain lives. AI can take a meaningful bite out of all of it. A few places to start:

• Lesson planning and differentiation: Use AI to generate lesson plan drafts, suggest differentiation strategies for varying learning levels, and build out unit frameworks. This gives teachers a strong starting point rather than a blank page.
• Feedback and grading support: AI can help draft written feedback on student work, suggest rubric language, or summarize patterns across a set of responses. Freeing teachers to focus on the nuanced judgment calls rather than the mechanical ones.
• Parent and family communication: Drafting routine communications, translating messages for multilingual families, or summarizing student progress for parent conferences are all tasks where AI can save meaningful time without sacrificing the human relationship at the center of it.
• Professional development and research: AI can serve as an interactive thinking partner for synthesizing articles, curriculum documents, or research — helping teachers apply what they’re reading rather than just getting through it.

For administrative and operational leaders, the opportunities are just as concrete:

• Meeting prep and follow-up: AI can summarize meeting notes, draft agendas, generate action item lists, and produce first drafts of board or committee updates. Repeated tasks that tend to eat disproportionate amounts of leadership time.
• Policy and document drafting: Whether it’s an acceptable use policy, a faculty handbook update, or a parent-facing FAQ, AI is useful for getting a solid first draft on the page quickly. The human judgment still lives in the review and refinement, not the blank page.
• Data synthesis and reporting: AI can help surface patterns in enrollment data, budget summaries, or survey results without requiring manual analysis from scratch.
• Workflow and process documentation: AI can help document existing processes and turn them into step-by-step guides — useful for onboarding, knowledge transfer, and reducing the “only one person knows how to do this” problem that plagues a lot of school operations.

The through-line across all of it: AI works best as a starting point, not a finishing point. It drafts, summarizes, and organizes — and then a human refines, approves, and delivers. That division of labor, done intentionally, is how schools get time back without losing the human judgment that makes the work meaningful. That’s not a threat to the teaching profession. It’s an investment in it.

Veracross was a premier supporting partner at this event. If you’re curious how Veracross is helping independent schools navigate the AI landscape — from data management to operational efficiency — we’d love to show you what we’re building.