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The Context-First Legal Department: Cutting the AI Noise and Solving the Context Tax

Nick Fleisher

Nick Fleisher

February 26, 2026

is co-founder and CEO at Sandstone. An engineer by training, he spent the last several years leading the legal tech service line at McKinsey & Company in New York where his on focus was on AI & automation for law firms, corporate legal teams, and legal tech companies.

For the modern General Counsel, the current landscape is defined by a paradox: departments have more tools than ever, yet less time to think. Trapped between a Board mandate to "modernize" and a CFO’s push for "efficiency," legal teams have become the "squeezed middle" of the enterprise.

But true transformation isn't about buying more software; it’s about fixing the Architecture of Intelligence. To move from a reactive cost center to a strategic control tower, legal leaders must eliminate the hidden drain on their productivity: The Context Tax.

The "Context Tax": The Silent Productivity Killer

The greatest drain on a legal team isn’t the complexity of the law—it’s the fragmentation of data. Context is the underlying history: the Slack threads, the previous redlines, and the business intent that turns a document into a solution. Currently, that context is scattered across emails, CLMs, and spreadsheets.

The Refocus Penalty:

Research from the University of California, Irvine indicates it takes over 23 minutes to fully refocus after an interruption. Every time a lawyer leaves a drafting window to search for a precedent in another tool, they aren't just losing minutes; they are losing cognitive momentum. If your team has more than three tabs open to complete a single task, you are likely paying a 30% "Context Tax" on your team’s intellectual output.

Why General AI Falls Short

General-purpose AI can draft an email or summarize a generic article, but legal work is unique, precarious, and interconnected.

  • The Lack of Institutional Memory: General AI understands legal theory but doesn't know your company. It cannot recognize the bespoke redlines your organization historically requires or calibrate for your specific risk appetite concerning indemnity.
  • The "Bolt-on" Trap: Many legacy vendors are simply "wrapping" a general AI model and adding it as a feature. If the AI doesn't have native access to your historical data and cross-tool communication (like Slack or Salesforce), it is a point solution in a platform’s clothing.

Choosing Your Architecture: Two Paths

To move away from the "Frankenstein" tech stack and toward a unified control tower, you must choose an architecture that supports—rather than fragments—your workflow.

The Point Solution: The "Task-Specific" Approach

  • The Focus: Designed to solve one isolated problem, such as NDA review or basic intake.
  • The Appeal: Offers rapid deployment and a lower initial price point.
  • The Pitfall: It inevitably creates Data Silos. Because these tools don't talk to each other, lawyers are forced into constant tool-switching.
  • The Result: A fragmented stack where the user is the only bridge between disconnected systems.

The Unified Platform: The "Control Tower" Approach

  • The Focus: Manages the entire legal lifecycle—from the first request to the final signature.
  • The Appeal: Provides shared context and cross-functional visibility, ensuring Sales, Finance, and Legal see the same "source of truth."
  • The Result: A Unified Strategic Asset that preserves institutional memory and allows AI to draw from every past negotiation.

To eliminate the Context Tax, legal departments must move toward an integrated infrastructure like Sandstone. Rather than asking the lawyer to change how they work, a unified system transforms how work reaches the lawyer.

  • Intelligent Playbooks: Traditional playbooks are static and often ignored. Sandstone transforms these into dynamic engines that analyze current contracts against your "Gold Standard" precedents.
  • High-Fidelity First-Pass Redlining: Sandstone handles the "commodity" cognitive load—standardizing definitions and applying baseline protections—so the lawyer never starts with a blank page. By surfacing the why behind a suggestion (linking back to a specific Slack discussion), the system ensures the "Context Tax" is paid before the lawyer even opens the file.

Measuring Success: Beyond "Efficiency"

When presenting to the CFO, pivot the narrative from "attorney efficiency" to "enterprise velocity." A unified infrastructure can reduce contract cycle times by 40%, directly driving top-line revenue.

The ROI Matrix should focus on:

  • Quality: Consistency in clause usage across the entire global team.
  • Retention: Reducing burnout by eliminating administrative drudgery.
  • Visibility: Using "heat maps" of resource allocation to reclaim outside counsel spend.

Conclusion: Reclaiming the Strategic Seat

The transition to an AI-native legal department is more than a software purchase; it is a strategic shift. By solving the Context Tax, you move away from the era of "Human as an API" and into the era of the Strategic General Counsel.