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The Play Newsletter

Practical AI for law firm operators. Not theory, not vendor pitches. What's going on and what's actually working, from someone running it.

Featured

Compliance

+3

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Aug 10, 2026

•

5 min read

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Matthew Roberts
Matthew Roberts

Articles

Compliance

+3

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Aug 10, 2026

•

5 min read

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Matthew Roberts
Matthew Roberts

legal-ops

+3

The Play — Issue #14: Nobody at Your Firm Bought the Bot in the Room

Aug 5, 2026

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6 min read

The Play — Issue #14: Nobody at Your Firm Bought the Bot in the Room

A researcher found 180,000 call records sitting open in January. The vendor never answered, and it was still open yesterday.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #13: The Word Document That Edits Your Work On the Way Out

Aug 3, 2026

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5 min read

The Play — Issue #13: The Word Document That Edits Your Work On the Way Out

One play: decide which inbound documents your AI assistant is allowed to read. Plus a firm insuring its agents, Goldman's stake in Harvey, and the $1,500-per-citation math.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #12: The Layer Beneath Your AI Tools

Jul 31, 2026

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5 min read

The Play — Issue #12: The Layer Beneath Your AI Tools

Three plays: the real AI vendor lock-in, validating an agent-led contract migration, and a ruling that could decide whether AI training needs a license.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #11: The Next Bad Citation in Your Case Won't Be Yours

Jul 29, 2026

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6 min read

The Play — Issue #11: The Next Bad Citation in Your Case Won't Be Yours

Three plays: check the other side's citations, put a source cite on every fact, and cut your biggest AI project down to one input and one output.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #10: Your AI Policy Governs the Keyboard

Jul 27, 2026

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8 min read

The Play — Issue #10: Your AI Policy Governs the Keyboard

Four plays: inventory what your AI tools can reach, move your policy from approved-tool to verified-citation, audit your engagement letter, and score build-vs-buy on maintenance.

Matthew Roberts
Matthew Roberts
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The Play Newsletter

Practical AI for law firm operators. Not theory, not vendor pitches. What's going on and what's actually working, from someone running it.

© 2026 The Play Newsletter.
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