Building an annual operations plan from scratch? Stop. It’s hiding in plain sight!

Every August, school technology teams are in full swing: prepping classrooms, staging laptops and tablets, checking every projector, printer, and port. It’s an intense time, and it’s easy to fall into “just get it done” mode instead of stepping back to think strategically about how current work connects with future needs. And to take a different perspective on the familiar…

When I stepped into a new IT leadership role years ago, my team could only list a handful of recurring annual projects. Not because they lacked skill or insight, but because their work had always been fighting fires instead of preventing them.

We changed that by mapping out a year’s worth of deliverables together. Our shared calendar included each project’s scope, so everyone could see what was coming and plan proactively. It took over a year of doing the work to understand the annual needs and nearly another year to transform it into actionable content.

If I were tackling that challenge today, I’d harness AI to amplify my team’s collective knowledge to:

𝟏. 𝐂𝐨𝐥𝐥𝐞𝐜𝐭 𝐬𝐡𝐚𝐫𝐞𝐝 𝐢𝐧𝐬𝐢𝐠𝐡𝐭𝐬 by asking team members to export email threads from this period last year. Every problem solved becomes future guidance.

𝟐. 𝐀𝐧𝐚𝐥𝐲𝐳𝐞 𝐨𝐩𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐚𝐥 𝐝𝐚𝐭𝐚 by pulling tickets and reports from the Help Desk system to spot recurring needs and pain points.

𝟑. 𝐓𝐫𝐚𝐧𝐬𝐟𝐨𝐫𝐦 𝐜𝐡𝐚𝐨𝐬 𝐢𝐧𝐭𝐨 𝐜𝐥𝐚𝐫𝐢𝐭𝐲 by feeding everything into a local Large Language Model (AI that runs on your own systems, keeping data secure) to create structured workflows from scattered knowledge.

𝟒. 𝐁𝐮𝐢𝐥𝐝 𝐭𝐫𝐚𝐧𝐬𝐩𝐚𝐫𝐞𝐧𝐜𝐲 through real-time collaborative checklists where issues become shared puzzles, not individual failures. Add automatic alerts to keep stakeholders informed.

The magic isn’t in the technology, but in showing your team their daily struggles have lasting value. When people see their experiences transformed into systems that help everyone, they feel empowered. When they contribute to building the playbook rather than just following it, they take ownership.

When you pair this psychological shift with AI’s ability to make hidden patterns visible, you’ll find that every problem your team has tackled before is iterating toward greater success.

𝐒𝐤𝐞𝐩𝐭𝐢𝐜𝐚𝐥? Talk with your team and pick an upcoming challenge that’s repeating from last year. Gather email, tickets, and conversations about it and prompt your LLM to create a project plan using the combined materials. I think you’ll all be amazed at the outputs and outcomes.