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

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.
The Sandstone Vision: Context-First Legal
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.