Winning with AI: How Lawyers Can Play at the Top of Their Game

The discussion on AI adoption in law firms brought together Gary Allen, a practicing lawyer and founder of LeanLaw, and Dennis Garcia, an experienced in-house legal professional with a background in leading technology companies such as Microsoft, Accenture, and IBM. Their conversation explored how AI tools can enhance legal practices by automating routine tasks, improving client relationships, and transforming legal operations, while keeping a strong focus on ethical AI usage and data security.

The session began with an introduction to the growing role of AI in law. Gary shared his passion for improving the business of law through technology, while Dennis provided insights from his career working closely with tech companies. They noted that participants in the conversation represented various stages of AI adoption—from those just beginning to those already experimenting and implementing solutions.

A major theme was the ability of AI tools to create efficiency in legal work. Dennis drew on his experience using Microsoft Copilot, explaining how it helped with drafting emails, working on contracts, summarizing documents, and transcribing Microsoft Teams calls. These tools, they agreed, can help lawyers focus on higher-value work, such as building relationships with clients and engaging in business development. However, both emphasized the importance of using AI as an enhancer, not a replacement, for human judgment—and of verifying outputs to ensure accuracy.

They also explored the potential of Agentic AI and Model Context Protocol in creating a more customized legal tech stack. These technologies could integrate different applications, streamline processes, and improve reporting, benefiting both law firms and in-house counsel. For example, Agentic AI might handle repetitive questions, freeing lawyers to focus on more strategic matters.

Maintaining client confidentiality emerged as a critical consideration when using AI in legal practice. Dennis stressed the importance of due diligence when choosing AI providers, ensuring that data protection measures are robust and that client information will not be leaked or misused. Gary added that law firms should clearly define their AI use cases and document processes to maintain ethical and secure practices.

The conversation also addressed the broader impact of AI on the legal profession. Dennis predicted that AI would reduce the need for lawyers in some areas while opening new opportunities in emerging fields of AI law. Both agreed that lawyers must proactively shape how AI is used in their field and understand its implications for their practice areas.

Dennis shared his personal experience of being laid off after more than two decades at Microsoft. While he could not say for certain that AI was the cause, he noted that job reductions are becoming more common in corporate America as technology advances. He approached the change with a professional perspective, seeing it as an opportunity to reflect and plan his next career chapter.

Looking to the future, both speakers emphasized the continued importance of human skills—communication, relationship building, empathy, and sound judgment—in an AI-driven legal landscape. AI may assist decision-making, but it cannot replicate human intuition or emotional intelligence.

They also discussed the role of AI in legal education. While AI can handle some routine tasks, new lawyers still need foundational skills and experience. Law firms should provide both the technology and mentorship needed to help young lawyers succeed, and law schools should adapt by integrating technology training into their curricula.

Finally, Dennis highlighted how AI is transforming client relationships and the structure of legal services. Law firms may face increasing questions about their AI strategies, and more clients may expect fixed-fee arrangements instead of hourly billing. AI’s potential in contract negotiations and management was identified as a key opportunity. His advice for small and mid-sized firms was to embrace AI, experiment with different tools, conduct thorough research, and learn from the experiences of others before committing to a solution.

Watch the full Webinar HERE