Field notes

The AI Champion's Playbook

The operator's manual for the accidental AI lead. Second edition, August 2026.

One-time. Updates included.

“Battle-tested in production environments.”

That is how Jared Spataro, Microsoft’s CMO for AI at Work, described my free, open-source Copilot prompt library in the AI at Work newsletter, February 2026. He was citing that free repo, not this product.

The situation

You got the mandate last quarter. Maybe in a hallway, maybe in a reorg, maybe because you were the one who already used Copilot and said something smart in a meeting. Now your job is to make AI adoption happen across the org, and nobody handed you a manual.

The strategy books talk to your CEO. The prompt books talk to your end users. You sit in the seat between them, the one who has to turn a slide about AI into a running pilot, a security review that clears, a policy people will read, and a number you can defend to finance.

What this is

This walks the work in the order you will actually face it: scoping a use case that survives contact, getting it through review, writing the policy, and producing the number. The second edition adds the review nobody owns yet, connectors, MCP servers and browser agents, plus a jurisdiction map so the gate chapter works wherever you answer to.

What perishes lives outside the book on purpose: the fast-moving vendor facts behind the tool-selection rubric sit in a quarterly annex at kesslernity.com/playbook, next to the errata and change log. When a regulation or a vendor fact moves materially, the digital files get corrected and every buyer receives the update.

What is inside

139 pages, 13 chapters across 5 parts, second edition
New: reviewing connectors, MCP servers and browser agents (Chapter 8)
New: the jurisdiction map, EU, UK, US states, UAE and Gulf, Singapore
The 12-artifact template pack: 11 editable templates plus the tool-selection scoring rubric
The full research bibliography, printed, so every citation resolves
The security review path, the policy people read, and the number finance accepts

Who it is for

The person who got handed AI adoption on top of their day job
AI champions, enablement leads, and internal programme owners
Security reviewers handed their first MCP server or agent approval

Who it is not for

C-suite readers looking for strategy. This is deliberately one level down from that.

Questions people actually ask

Is this Microsoft-specific?

No. The examples lean Copilot because that is the estate most readers are in, but the work of getting adoption through an organisation is platform-agnostic.

Will it go stale when the regulation or the vendors move?

It already survived that once: the first edition printed the EU AI Act date with a warning it would move, the Digital Omnibus moved it, and the second edition shipped the correction free to every buyer. The fast-moving vendor facts now live in a quarterly annex at kesslernity.com/playbook, alongside the errata and change log.

Does it cover AI agents and MCP servers, or just chat assistants?

Chapter 8 is dedicated to it: the review that replaces vendor paper when the connector is a community repo, permission inheritance, credentials and outbound flow, and the register InfoSec will ask for. It ships with its own pre-flight checklist.

How is this different from the Deployment Kit?

The Kit is artifacts for a Copilot rollout. This is the operator's job across the whole mandate, including the parts that are not a tool deployment at all.

Buying this with a company card?

Most buyers expense it. Your receipt email carries a Generate link that opens an invoice generator: add your billing address, put your legal company name and any reference your finance team needs in the Additional notes box, and download the PDF. If you have an EU VAT number, enter it at checkout and no VAT is charged. Here is the approval email, so you do not have to write one.

Approval email

Subject: Approval request: The AI Champion's Playbook ($59, one-time)

Hi [Manager],

I would like to expense a one-time $59 purchase: The AI Champion's Playbook by Kesslernity.

What it is: The operator's manual for the accidental AI lead. Second edition, August 2026.

What we get:
- 139 pages, 13 chapters across 5 parts, second edition
- New: reviewing connectors, MCP servers and browser agents (Chapter 8)
- New: the jurisdiction map, EU, UK, US states, UAE and Gulf, Singapore
- The 12-artifact template pack: 11 editable templates plus the tool-selection scoring rubric

Why it is worth it: it is a one-time purchase with future updates included,
and it costs less than an hour of any consultant we would otherwise ask.
The author publishes the open-source Copilot prompt library that Microsoft's
CMO for AI at Work cited as "battle-tested in production environments".

A downloadable invoice is available from the purchase receipt for expenses.

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