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The Arithmetic of AI: Tokens and Claude in Legal Work
Published 2026-06-03
Every AI interaction carries an invisible meter. Understanding how it works is central to using these tools effectively. This piece examines tokens, context windows, and how they shape the cost, quality, and confidentiality of AI-assisted legal work.

$500 Million Is a Start. Now Ask Where Your Firm Stands.
Published 2026-06-02
Kirkland & Ellis's $500 million investment in building proprietary AI is headline news. What it actually represents is a long-overdue reckoning with an historic wrong. Kirkland is finally doing at scale what the legal profession should have been doing for years.

Anthropic Files a Confidential IPO and Suddenly It All Makes Sense
Published 2026-06-02
Anthropic's confidential IPO filing may help us understand why it launched so many vertical products with only lightweight support programs. Now, that series of strategic decisions that previously seemed unusual suddenly look a little more coherent.

The Em Dash Is Dead. Long Live the En Dash!
Published 2026-06-02
While the much-maligned em dash has become associated with AI-generated content, it actually has a long history of use in U.S. journalism and academic writing (which is where AI learned it). So, the next time you wonder whether something you’re reading is AI-generated, stop and ask yourself this—am I reading something from a source I’ve long respected as an authority and whose expertise I have never questioned, but now am simply because I’ve noticed em dashes in the writing? The problem in that scenario is not the writer. Here’s your linguistics lesson explaining why.

The Friction Fighter
Published 2026-05-27
It’s too easy to over-focus on technology and under-focus on the management philosophy behind it, and that philosophy has a name: Ceremonial Supervision. This is the practice of prioritizing visible, additive activity (e.g., new AI tools, dashboards, and committees) to create the appearance of progress while leaving the underlying friction untouched. To counteract it, your innovation mandate must explicitly include the authority to delete.

The Forward-Deployed AI Model Is Real. Most Legal Teams Aren’t Ready for It.
Published 2026-05-26
The teams seeing the most success with forward-deployed AI are usually the ones that operationalize their legal knowledge first. Not just templates, but fallback positions, approval logic, negotiation patterns, and institutional context. Once that structure exists, AI can operate with far more consistency across workflows.
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