The 2026 Legalweek Leaders in Tech Law Awards honor those who have made significant contributions to legal innovation from law firms, corporate legal departments and legal tech providers.
While many awards recognize the contributions legal professionals or organizations made over the past year, our new Monica Bay Women of Legal Tech Award honors women at law firms, legal departments, and legal technology or legal service companies who have achieved notable successes and made significant contributions to legal innovation over the course of their careers.
The award is named after the former editor-in-chief of Legaltech News. Bay, a pioneer in the space who fostered an entire generation of legal tech professionals, was dedicated to recognizing and empowering women across the industry.
Rachel Shields Williams, director of client intelligence at Sidley Austin is one of the winners of this year’s Legalweek Leaders in Tech Law, Monica Bay Women of Legal Tech Award.
What do you currently see as the biggest barriers to, and biggest drivers of innovation in law firms?
Innovation in law firms is accelerating, but progress is still shaped by a mix of cultural, structural, and technological forces.
The biggest barriers remain cultural and operational. Law firms are built on precedent, not experimentation, which can make change feel risky. Many professionals worry that new technology may disrupt established workflows, introduce uncertainty, or impact work quality. Data fragmentation is another major barrier,firms often have vast information stored across disconnected systems, making it difficult to build reliable AI, analytics, or automation solutions. Finally, without clear ownership of data and technology initiatives, well-intentioned efforts can become siloed, duplicative, or misaligned with strategic priorities.
At the same time, the biggest drivers of innovation have never been stronger. Client expectations are evolving rapidly,organizations want faster insights, smarter collaboration, and more predictive, data-driven service. This pressure creates urgency and accelerates investment in AI, data strategy, and workflow modernization. The profession is also seeing a growing generation of lawyer and business professionals who are deeply curious about technology and eager to work differently. The emergence of dedicated Data & AI teams in law firms provides structure, clarity, and governance to support sustainable innovation rather than one-off experimentation. And most importantly, the appetite for cross-functional collaboration is rising:Marketing, KM, IT, practice groups, and administrative teams are increasingly solving problems together rather than independently.
Innovation succeeds in law firms when cultural readiness meets operational clarity. Firms that invest in data foundations, empower multidisciplinary teams, and create psychologically safe environments for experimentation will leadthe next era of legal transformation. The driver is no longer technology itself,it is the people willing to bridge worlds, reimagine old processes, and champion change with empathy and purpose.
Emerging technologies such as generative and agentic AI are enabling new levels of automation in law firms. How do you expect these changes to impact law firms' operations, staffing and/or business models?
Generative and agentic AI are reshaping law firms in ways that directly reflect what clients want most: faster answers, deeper insight, and more predictable value. Operationally, AI will transform legal work from reactive and manual to proactive and insight-driven. Tasks like research, drafting, document review, data extraction, and knowledge retrieval will become faster, more consistent, and increasingly automated. Agentic workflows will take this further, moving from generating outputs to executing multi-step processes that anticipate needs and streamline complex tasks behind the scenes. Clients will experience quicker turnaround times, higher accuracy, and a more seamless service experience.
These technologies will strengthen client intelligence and personalization. By unifying data across platforms, firms will be able to surface relevant trends,anticipate risks, and identify opportunities before clients even request them. This shift—from service delivery to strategic partnership—will redefine what it means to be a client-centric firm.
Staffing models will evolve to enhance the client experience, not diminish it. AI will automate repetitive, rules-based tasks, freeing professionals to focus on higher-value work: advising clients, designing strategy, navigating nuance, and collaborating across disciplines. New roles in AI governance, product management, data quality, and workflow design will support smarter, safer, and more client-aligned innovation.
Business models will shift because clients will increasingly expect value, outcomes, and transparency, not hours.
As AI shortens the time requiredfor certain tasks, firms will adopt more creative pricing models, including subscription-based offerings, fixed fees, and outcome-driven engagements.
Ultimately, generative and agentic AI won’t replace the lawyer-client relationship,they will enhance it. Firms that invest responsibly in data foundations, cross-functional collaboration, and human-centered change will deliver the speed, insight, and partnership clients now expect from modern legal service providers.
How would you like to see technology specifically designed for law firms change over the next few years, and why?
As generative and agentic AI accelerate change, I hope to see legal technology evolve in ways that strengthen data fundamentals, elevate intelligence, and foster collaboration, all to deliver deeper value to clients.
Legal technology must invest in strong data foundations because clients depend on accurate, timely insight. Today’s clients want firms that understand their business,anticipate risks, and provide proactive guidance. That requires clean, connected, high-quality data; standards, taxonomies, governance, and interoperability. When firms unify and trust their data, they deliver faster answers, clearer recommendations, and more reliable analysis.
Technology must be designed for adoption so clients feel the benefits, not the functional burden. Clients don’t experience the tool,they experience the output. When systems are intuitive and embedded within lawyer workflows, work becomes faster, more efficient, and more consistent.Technology that is actually used leads directly to better client service, fewer delays, and more predictable results.
Legal tech should elevate intelligence—not just automate tasks. Clients increasingly want insights: patterns in their matters, emerging risks, benchmarking, competitive positioning, and predictive indicators. The next generation of tools should surface intelligence that helps clients make smarter business decisions and strengthens the lawyer-client partnership. Insight-driven counsel is quickly becoming a differentiator.
Technology must enhance collaboration across teams to deliver a more seamless client experience. Clients don’t think in silos, and firms shouldn’t operate in them. Technology that connects marketing, KM, IT, data teams, finance, and practice groups leads to more coordinated service, faster turnaround, and clearer communication. Collaboration is one of the most powerful drivers of client satisfaction.
Ultimately, the evolution of legal technology should focus on one goal: helping law firms deliver smarter, faster, more connected, and more insightful service to their clients. When data, adoption, intelligence, and collaboration come together, clients feel the difference.