For most of my career, legal technology had little to do with the real work of the General Counsel.
I began practicing at Cleary Gottlieb, and later spent many years in-house at global financial institutions and at Bridgewater Associates. In each setting, the General Counsel's role was unmistakable: accountability for the firm's legal exposure, particularly under stress. During the financial crisis, that accountability ceased to be theoretical. Questions of contractual rights, termination triggers, collateral provisions, regulatory interpretation were not abstractions. They were live, and they were urgent.
Technology was present, of course. We drafted more efficiently than prior generations. We redlined electronically. We stored documents centrally. But none of that altered the underlying constraint: legal risk lived inside documents and inside people's heads. When the CEO asked how exposed the firm was, the answer required assembling fragments from institutional memory, representative sampling, outside counsel analysis and manual review. Technology improved how lawyers worked but did not change the informational foundation upon which the General Counsel advised the enterprise, encouraging their rational indifference.
That distinction between operational efficiency and risk visibility explains a great deal about the relationship between senior legal leadership and technology over the past several decades. It also explains why that relationship is due for reexamination.
The General Counsel’s role is defined less by task execution than by accountability when exposure materializes. When regulatory scrutiny intensifies, when litigation escalates, when contractual disputes threaten revenue or liquidity, the GC is answerable to the CEO, to the board, and sometimes to regulators themselves.
In practice, the function has three defining characteristics. First, it operates at the level of cumulative exposure, not individual transactions; second, it is forward-looking, not merely interpretive; and finally and most critically, it is exercised under uncertainty, often under acute time pressure.
The GC's core output is not drafting or workflow oversight: it is judgment under constraint. Judgment about where the enterprise is exposed, how severely, and what to do about it.
That judgment rests on information. For most of modern corporate history, the information available to support it has been structurally incomplete.
Legal exposure is distributed across thousands of heterogeneous agreements, regulatory commitments, policies, and correspondence. The terms that define risk, liability caps, indemnification structures, termination triggers, regulatory commitments are embedded in unstructured text, negotiated individually, and stored across systems that were designed for retrieval, not analysis. Unless those terms are abstracted into structured data, they cannot be aggregated, modeled, or stress-tested at scale.
The GC's oversight has therefore been necessarily inferential. It relies on institutional memory, escalation reporting, periodic audits, and the synthesis of experienced lawyers who carry contextual knowledge that exists nowhere else in the organization. This approach has functioned for decades. It is not irrational. It reflects the informational tools that were available.
But it means that the GC has historically managed enterprise legal risk with limited structural visibility into the very commitments that constitute that risk.
Legal department budgets reflect this reality. The overwhelming majority of legal spend is allocated to personnel: internal lawyers, staff and outside counsel. This is not inertia; rather, it reflects where leverage has historically resided. When risk increases, you hire specialists. You retain external expertise. You escalate human judgment. Capital follows perceived risk leverage, and the return on experienced legal talent is visible in a way that the return on workflow acceleration is not.
Technology spend, by comparison, has typically been modest. Not because General Counsel are indifferent to efficiency, but because efficiency is not the primary constraint on enterprise exposure. A GC can tolerate process friction. A GC cannot tolerate unknown risk.
This investment pattern is reinforced by a structural staffing constraint that anyone who has managed a legal department will recognize. Legal departments do not and cannot staff for volatility. Enterprise risk is episodic: most of the time, exposure simmers; occasionally, it spikes. But corporate budgeting is steady-state, and each year brings some version of the mandate to do more with less. Departments are structured leanly, calibrated to expected volume rather than worst-case demand, with the understanding that when spikes come, internal teams will stretch and outside counsel will be engaged.
The consequences are predictable. In ordinary periods, internal lawyers manage comfortably. When risk intensifies—a regulatory investigation, a market dislocation, a litigation wave—the department absorbs extraordinary load. Senior lawyers triage, mid-level lawyers are overextended, and morale strains.
And then, when legal risk shades toward franchise risk, when the exposure becomes visible at the board level, when the numbers become material, the cost calculus shifts instantly. No one debates hourly rates or optimizes fee structures. The most experienced and reputable outside counsel are retained (if they aren’t retained by your peer firms first), because at that moment the relevant risk is not the legal department budget. It is the survival and reputation of the enterprise.
This is not dysfunctional; instead, it is rational behavior under asymmetric and asynchronous risk: the downside of underreaction dwarfs the cost of escalation, and the timing of acute exposure resists the logic of steady-state resourcing. But it produces a recurring cycle: lean staffing, episodic overload, expensive external escalation, normalization, and then lean staffing again. The pattern repeats because the underlying informational constraint remains unchanged.
Within this cycle, the comparative advantage of internal legal teams has never been volume. It has been proximity.
Senior in-house lawyers (and of course experienced paralegals) carry forms of capital that cannot be purchased on demand: institutional memory, contextual understanding of the business model, knowledge of historical compromises and negotiating positions, direct relational credibility with internal stakeholders. They understand not only the text of agreements but the commercial logic behind them, the risk appetite of the organization, and the informal tolerances that shape decision-making in practice.
When work migrates to outside counsel, this knowledge must be transmitted. That transmission is possible. A seasoned partner at an elite firm can internalize a company's risk posture, commercial logic, and historical practice with impressive speed. That ability to synthesize complex context rapidly is precisely what commands premium rates. The limitation is not competence. It is scalability and continuity.
Context absorption is episodic and expensive. Each new matter, each new crisis, requires some degree of reconstruction. Even where the same firm remains involved over years, knowledge accrues through individuals whose engagement may fluctuate. Internal teams, by contrast, live inside the enterprise. Their knowledge compounds through repetition and proximity.
The question is not whether outside counsel can be brought up to speed. They can. The question is whether an operating model built around repeated context transfer reconstructing institutional knowledge under time pressure each time exposure spikes is the most resilient foundation for managing systemic legal risk. In crisis conditions, the cost of delay is often higher than the cost of fees. External escalation introduces not only financial cost but coordination cost: assembling teams, transmitting information, reconciling interpretations across firms and practice areas. Those frictions are manageable, but they are real, and they compound when speed matters most.
For most of the past three decades, legal technology developed around the operational edges of the legal function. This was not because vendors lacked ambition, but because only those edges could be systematized.
Workflow could be structured, document generation templated, spend tracked, signatures digitized, and storage centralized. These have been meaningful advances, reducing friction, improving departmental discipline, and making the work of legal professionals more consistent.
But the core of the GC's responsibility, understanding and managing aggregate legal exposure, is qualitatively different. It involves interpretation, aggregation, judgment across heterogeneous agreements, and contextual analysis under uncertainty. That complexity was not reducible to routing logic or document automation. Technology matured where it could, and largely stopped where it could not.
The result was a persistent, if quiet, gap between the technology conversation and the GC's core mandate. Senior legal leaders were not indifferent to innovation. They were rationally focused on a different problem that the available tools did not address.
There was also a subtler constraint. For technology to meaningfully support the GC's core mission, it would require deep engagement from senior lawyers: defining risk models, calibrating data interpretation, validating outputs, aligning systems with real exposure dynamics. That level of attention is the scarcest resource in any legal department. Senior lawyers spend their time on crisis management, regulatory relationships, litigation oversight, board reporting, and strategic transactions. Pulling that attention toward technology implementation was difficult to justify when the tools themselves did not alter the risk substrate.
This created a feedback loop. Tools improved workflow. Workflow was delegated. Delegated tools remained peripheral. Peripheral tools did not attract senior attention. And without senior attention, tools were never reshaped around the core function.
The relative detachment of General Counsel from the legal technology conversation has often been attributed to cultural conservatism. That explanation has never struck me as persuasive. The tools on offer, even when ambitious in their claims, largely addressed how lawyers executed tasks. They did not materially alter the visibility of enterprise legal exposure. The disinterest was less resistance than misalignment.
This remains, in most organizations, the prevailing structure. Legal departments continue to allocate the overwhelming majority of budget and senior attention toward human expertise. Technology, while more sophisticated than in prior decades, is still largely framed in terms of operational improvement.
But the underlying constraint that kept technology peripheral may itself be loosening.
The barrier was never imagination. It was structure. Legal risk was embedded in unstructured text, and no amount of workflow optimization changed that. If advances in data extraction, natural language processing, and computational analysis begin to make the substance of legal obligations queryable, aggregable, and modelable, then the informational foundation of legal oversight changes.
The difference is not automation: it is decision-grade visibility.
When contractual and regulatory commitments can be translated into structured data, several things become possible that were previously impractical: aggregating liability caps across a portfolio, identifying regulatory triggers embedded in termination clauses, quantifying renewal exposure tied to revenue streams, detecting deviations from policy at scale, modeling downstream effects of external shocks.
This does not eliminate judgment. It changes the substrate on which judgment operates. The GC's advice, in this model, is not derived solely from experience and institutional memory, but from visibility into patterns and distributions across the organization's legal commitments.
Consider the moment of crisis that defines the GC's role. When the CEO asks, "How exposed are we?" the historical answer has been some version of, "We're reviewing." With structured legal data, the answer can move closer to, "We know, and here is what we see." That difference is not rhetorical. It is the difference between reactive mobilization and informed response. It changes the speed and confidence with which the enterprise can act.
It also changes the informational footing on which external expertise is engaged. If more of the enterprise's contractual and regulatory posture can be made structurally visible in advance, rather than interpreted for the first time under stress, then the amount of tacit institutional knowledge that must be reconstructed each time outside counsel are engaged decreases. External escalation becomes more precisely targeted. Internal expertise becomes more scalable, not in volume, but in impact. The balance between embedded institutional judgment and imported episodic expertise shifts because the informational baseline on which internal lawyers operate becomes richer.
But the consequences of that richer baseline extend beyond how expertise is deployed. They reach into the quality of the decisions themselves. When exposure is opaque, decisions must be calibrated to the range of what might exist in the portfolio rather than to what actually does. That imprecision has real cost: in negotiation posture, in reserve-setting, in regulatory response, in the persistent gap between how the enterprise believes it is positioned and how it actually is. Structural visibility narrows that gap and allows decisions to be made against known positions rather than estimated distributions.
Consider a practical example. When an organization is evaluating the acquisition of a distressed company, uncertainty about the target's contractual and regulatory exposure does not simply increase diligence cost. It distorts the bid itself. Unknown obligations demand risk premia. The acquirer prices not for what is there, but for what might be, a version of the winner's curse where the winning bidder is disproportionately likely to be the one who most underestimated what they were acquiring. The more granular the visibility into what actually exists in the target's contractual portfolio, the more precisely the bid reflects real risk. You win the acquisitions you ought to win, and you lose the ones you ought to lose. That calibration has direct enterprise value, and it is unavailable under conditions of opacity.
The same logic applies across time, not only across decisions. When contractual provisions are visible before they become actively relevant, the organization can act on them proactively: renegotiating terms, amending exposures, restructuring positions in advance of trigger events rather than scrambling in their aftermath. The option to intervene early, rather than react late, is largely inaccessible when obligations are buried in unstructured text. Unlocking it may be the quietest but most consequential shift that structural visibility produces.
A portion of what has historically been addressed through high-cost reactive intervention will migrate into a more scalable operating model. But the deeper economic shift is not in the cost of mobilization. It is in the precision and timing of the decisions that legal visibility enables.
No system removes the need for experienced legal judgment. Nor does structural visibility eliminate volatility, or render the enterprise immune to surprise. Much of the GC function remains irreducibly judgment-based. Reputational risk, regulatory mood, strategic timing resist systematization and probably always will.
But reducing opacity around contractual and regulatory commitments changes the starting point for that judgment. It shifts the GC from interpreting a set of representative examples to overseeing a measurable system. It strengthens advice not by replacing the lawyer's role, but by improving the information available to inform decisions and advice, and empowers lawyers to give advice in the language of the business. Legal risk becomes something that can be weighed, not merely described.
Consider the baseline. For decades, the GC function evolved within conditions of informational opacity. Technology reinforced that opacity by making document handling smoother without making obligation visibility clearer. The tools were appropriate to their time. The disinterest of senior legal leadership was appropriate to the tools.
The question now is whether the constraint that defined that era, the intractability of unstructured legal text at scale, is beginning to yield. If it is, then the relationship between the General Counsel and legal technology changes. Not because the GC's mission changes, but because technology, for the first time, begins to address that mission directly.
That would represent not merely a product evolution, but a shift in how legal risk is governed at the institutional level. And it is a question that deserves the attention of precisely the people who have, until now, been rational in withholding it.