Selecting legal technology has become one of the most consequential strategic decisions facing legal departments. An expanding market of platforms promises efficiency, compliance, and scale, yet many organizations still struggle to see meaningful returns on their investments. For Mathew David Crocker, Chief Strategy Officer at Morae, the real risk lies in beginning the process without a clear understanding of the problem technology is meant to solve.
“No one puts a document management system in for fun,” Crocker says. “At its heart, there is normally a business problem you are trying to solve.” Legal technology only delivers value when it’s anchored to defined outcomes rather than features, vendors, or prevailing trends. With more than two decades spent modernizing legal operations, from large-scale document management deployments to complex post-merger integrations, Crocker has seen how quickly initiatives can lose direction.
Legal departments frequently describe their objectives in broad terms such as organization or efficiency. Crocker views those descriptions as incomplete. In practice, the underlying challenge is often governance. Organizations need clarity on where documents reside, how long they’re retained, and how they’re disposed of in line with regulatory obligations. Technology, in this context, is an enabler rather than the objective.
The gap becomes more pronounced when key stakeholders are left out of the conversation. Contract workflows offer a clear example. Legal teams may own contracts, but those documents move through sales, procurement, and external counterparties. “If this is an NDA,” Crocker says, “do we really need seven to fourteen days of red lines?” Without mapping the full business process, technology reinforces friction instead of reducing it.
Legal Teams Need Technology Built for Legal Work
In corporate environments, legal teams are often a small function within a much larger organization. A legal department of 50 may sit inside a business of 10,000 employees, creating pressure to conform to standard enterprise tools. It’s a common misdiagnosis.
“Legal is different,” he says, pointing to regulatory exposure and the complexity of multi-party document negotiation. While tools like Word or SharePoint are adequate for general collaboration, they aren’t designed for the intensity of legal redlining across internal and external teams. Specialized platforms reduce turnaround times dramatically, turning hours of manual work into minutes. Efficiency isn’t a nice to have. When repeated tasks are accelerated, capacity is freed for higher-value legal judgment, allowing teams to focus on risk, strategy, and business enablement rather than administrative drag.
AI, Dark Data, and the Expanding Risk Surface
Generative AI has intensified both opportunity and risk. Crocker sees AI as a genuine inflection point, particularly when models are trained on an organization’s own contracts and intellectual property. “I can give you a branded, well-thought-through NDA far quicker by looking at the last thousand contracts,” he says, calling it a curation exercise rather than a leap of faith.
At the same time, AI exposes weaknesses in information governance. Crocker estimates that between 25 and 50% of organizational documents sit outside core systems, often in locations with weaker retention and security controls. This so-called dark data creates compliance gaps and cyber exposure that many organizations don’t see until it’s too late.
Technology selection, then, is inseparable from data discipline. Without understanding where information lives and how it’s governed, even the most advanced tools amplify existing problems.
Planning for Change in a Fast-Moving Market
Traditional legal systems such as document management, contract lifecycle management, and matter management are long-term investments. Implementations can stretch from six months to two years, during which priorities, leadership, and regulations often change. Crocker stresses the importance of revisiting scope at defined intervals rather than locking into assumptions made at project launch.
The pressure intensifies in the AI market, where barriers to entry have fallen and new vendors emerge weekly. Three-year contracts that once felt prudent can look restrictive within 18 months. It’s difficult to plan beyond a three-year horizon, particularly as AI functionality begins to overlap with established systems.
Crocker draws a distinction between vertical AI embedded in individual platforms and horizontal AI that works across the stack. End users don’t want fragmented answers from siloed systems. They want insight that spans matters, documents, and contracts in a single view. Vendors that enable that horizontal perspective are more likely to endure.
Fit Matters More Than Speed
Across growth initiatives and acquisitions, Crocker returns to the same principle. Technology should serve a clearly articulated operating model. As organizations scale, standardization becomes essential, even when it introduces short-term friction. Allowing parallel systems to persist may feel pragmatic, but it often results in manual workarounds that drain strategic capacity.
The evaluation of a legal technology stack, then, is less about chasing innovation and more about disciplined alignment. When the problem is clearly defined, stakeholders are engaged, and data realities are acknowledged, technology becomes what it should be: a catalyst for durable, measurable impact.
Follow Mathew David Crocker on LinkedIn or visit his website for more insights.
