The Tenant Whisperer: Custom Skills and the CLI for Microsoft 365

What if you could ask questions about your Microsoft 365 tenant and get back structured, repeatable, and documentable answers with no black box involved?

In this session, we show how custom skills built around the CLI for Microsoft 365 can make AI tools far more useful for administrators and developers. A skill is a reusable, shareable command that tells your AI tool exactly how to interact with your tenant. Done well, it turns one-off questions into repeatable operational knowledge.

We will walk through what a good skill looks like, how to structure output so tools like GitHub Copilot CLI or Claude Code can reason over it properly, and how to combine skills, CLIs, and MCP servers to take care of repetitive tenant work.

You will learn how to:

• Build custom skills that are understandable and reusable months later
• Query your Microsoft 365 tenant and return structured output AI tools can reason about
• Share skills across your organization so the approach scales beyond one person
• Combine skills, CLIs, and MCP servers into more complete automation flows
• Turn one-off tenant questions into living documentation

This session is aimed at Microsoft 365 administrators and developers with experience using agents, CLI tools, or PowerShell scripts. We will not go deep into skills governance or the administrative permission and security requirements needed to run skills across an organization.