Legal in the AI Era: A Conversation With Aine Lyons

The transformative power of artificial intelligence on the legal profession starts first with changing mindsets. By shifting mindsets and adopting new tools through AI-powered contract intelligence, legal professionals can usher in unprecedented levels of productivity and efficiency gains.

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Like all industries, the legal profession isn’t exempt from the changes brought on by technology advancements over the last few years. The opportunity to streamline processes and drive unprecedented efficiency gains is promising—but no opportunity worth seizing is without its challenges.

In a recent Future of Work podcast, Jerry Ting, vice president, head of agentic AI and Evisort at Workday, sat down with Aine Lyons, senior vice president and deputy general counsel at Workday, to discuss the transformative impact of AI on the legal profession. 

Fresh from accepting an award for being among the top 20 legal intrapreneurs of the past two decades, Lyons and Ting reflected on how innovation, particularly in the realm of artificial intelligence, is reshaping the legal landscape. And, by extension, influencing how legal professionals think about the future of work. 

Read on for invaluable lessons for leaders in the legal space who are looking to spearhead the evolution of legal demands of the modern enterprise.

Changing Mindsets: A Core Theme of Legal Innovation

Lyons began by reflecting on transformations during her career, noting that a consistent theme has been around changing people's mindsets. When considering the type of person the legal profession attracts—methodical, judicial, structured individuals—this is no small feat.

She highlighted the traditionally conservative nature of the legal profession, now on the cusp of an AI revolution that will significantly accelerate change in daily operations. Lyons pointed to five critical expectations:

  1. Be unexpected: CEOs want legal professionals with a "business mindset, but a legal heart," capable of solving complex business challenges.

  2. Agility: The ability to adapt and challenge the status quo of traditional legal work is paramount.

  3. Simplicity: Legal teams are encouraged to simplify processes, templates, and communication to enhance the customer experience.

  4. Be AI adept: Embracing AI to drive efficiencies and impact is no longer a luxury, but an expectation.

  5. Collaboration: AI tools should ideally benefit multiple functions across the enterprise to maximize ROI and foster buy-in.

These points resonate strongly with the evolving role of in-house legal departments today. Just as legal teams are urged to be more business-minded and agile, they are constantly striving to simplify processes, leverage technology for efficiency, and foster cross-functional collaboration within their organizations. All of which can be complemented by the use of modern solutions.

From "Bright, Shiny Objects" to Enterprise-Wide Solutions

Lyons and Ting, both with extensive backgrounds in legal technology, discussed the difficulties of  tech implementations. 

Lyons observed that "80% of tech implementations by legal departments are very challenging and don't deliver an ROI." 

This highlights a crucial point for legal leaders: the mere presence of a bright, shiny object in technology does not guarantee success. The focus must be on impactful tools that deliver tangible savings, efficiencies, and most importantly, widespread adoption.

They also touched on Workday's acquisition of Evisort, an AI-powered contract intelligence platform. 

Lyons noted that Evisort is not just a legal tool but an enterprise capability that can analyze both contracts and financial data. This broad applicability is a force for success and aligns with the principle of collaborative, cross-functional tools. Lyons also shared a close-to-home anecdote about the Workday legal team’s use of leveraging Evisort for due diligence—during their acquisition of Evisort.

The mere presence of a bright, shiny object in technology does not guarantee success. The focus must be on impactful tools that deliver tangible savings, efficiencies, and most importantly, widespread adoption.

Evisort's ability to analyze contracts using AI and surface up business insights at your fingertips, wherever you're operating, has been an invaluable strategic advantage.

For legal professionals considering new technologies, this integration of AI directly into legal workflows is a critical takeaway as embedding AI capabilities seamlessly into existing platforms makes it easier for legal professionals to adopt and leverage them.

Practical AI Use Cases and Quantifiable Impact

To make the power of AI tangible, Lyons shared several instances where Evisort made an impact within Workday's legal department, offering insights that legal professionals can readily apply to their own functions:

Contract Analysis at Scale

With over 100,000 customer contracts and order forms, Workday's legal team turns to Evisort to "X-ray using our custom AI, and extract different data points that we need." This ability to quickly identify obligations, restrictions, and opportunities within a vast contract repository is critical for legal teams managing complex commercial relationships.

Expedited Due Diligence

Lyons provided a powerful example of Evisort's efficiency during mergers and acquisitions. When analyzing over 1,000 contracts for a recent due diligence process, Evisort completed the analysis in a single day—a task that would have taken outside counsel a week and cost approximately $50,000. This demonstrates the potential for massive cost savings and accelerated timelines that AI can bring to complex transactional legal work.

Rapid Information Retrieval

Legal departments frequently receive requests for information such as marketing restrictions, renewal dates, or cyber breach notification obligations. According to Lyons, this would usually involve manual reviews taking several resources to open those contracts, read through them, analyze them, and putt them in some kind of spreadsheet. 

With Evisort, teams can generate these reports in a matter of hours versus weeks, leading to an average savings of about 180,000 hours a year in general contract analytics requests. For legal teams, this translates to faster, more accurate responses to business inquiries, freeing up valuable time for more strategic legal counsel.

Workday's legal team is also proactively tracking 54 different data points about their customers, pushing this information back into Salesforce customer records. This cross-functional collaboration, involving finance, revenue operations, and deal management, creates a holistic view of customer relationships that empowers legal and business teams.

Lyons proudly stated that Workday's initial investment in Evisort has "paid for itself 35 times over, over the last three years." This strong ROI metric underscores the importance for legal leaders to not only identify potential AI tools, but also to build robust business cases that quantify the expected savings and value.

“Workday's initial investment in Evisort has paid for itself 35 times over, over the last three years.”

Aine Lyons SVP and Deputy General Counsel, Workday

Upskilling for the AI-Powered Future of Legal Work

The widespread adoption of AI creates a need for significant investment in upskilling. Lyons highlighted Workday's unique approach, where "every one of our 20,000 employees has a goal around AI." 

For the legal team, this has meant over 20 hours of training for each member to become more proficient in prompt engineering. This commitment to company-wide reskilling is a crucial lesson for legal departments. 

These types of investments make employees feel valued by the company, with their development prioritized, which is crucial as employee concerns around being left behind surface.

Lyons also praised Evisort's user-friendly interface, noting that even a proof of concept can quickly demonstrate value. This ease of use is a vital consideration for legal technology implementations, as user adoption is often a significant hurdle.

Building Strategic Partnerships Between Legal and the CIO

A critical success factor for Workday's legal team has been its strong partnership with the CIO. 

Lyons advocated for the CIO to be "the best friend of legal," recognizing that legal departments historically weren’t traditionally poised to be really good at implementing technology.

By collaborating with the CIO to explore the AI landscape, demo tools jointly, and build a unified AI strategy, legal teams can present a more powerful business case for investment. This cross-functional alignment is paramount for legal teams to establish. Partnering with the CIO can help legal identify secure, scalable, and integrated AI solutions that benefit the entire organization, not just a single department.

AI-Ready Advice for Legal Teams

In order for legal teams to have a starting point in their AI journey, Lyons offers some practical advice based on her experience:

  • Develop a tech strategy: Don't go it alone. Seek help in building a comprehensive technology strategy.

  • Address core business challenges: Identify the "highest and biggest challenge, not just as a legal team, but as a business." For many companies, this is a lack of a single source of truth for contracts—a fundamental issue legal teams are uniquely positioned to address.

  • Align with business imperatives: Connect your AI use cases directly to broader business goals, such as scale and speed. Legal can align AI initiatives with accelerating deal cycles, enhancing compliance, or optimizing risk management.

  • Foster cross-enterprise partnerships: Collaborate with as many functions and senior leaders as possible. Strong relationships ensure that the legal team’s priorities are tightly connected to the overall business strategy. 

  • Avoid silos: Lyons stressed the importance of "getting out of your silo, an starting to work east to west." This collaborative approach can supersize your impact.

By collaborating with the CIO to explore the AI landscape, demo tools jointly, and build a unified AI strategy, legal teams can present a more powerful business case for investment.

The Path Forward

The conversation concluded with Lyons emphasizing the importance of professional generosity.

Workday's legal team, seeing themselves as forward thinkers on AI, is committed to sharing their learnings about Evisort, articulating ROI, developing use cases, and fostering adoption and reskilling. 

This collaborative spirit is essential for legal leaders as they collectively navigate the complexities of AI adoption. By sharing best practices and lessons learned, the legal community can accelerate its own AI journey.

These insights regarding strategic partnerships, quantifiable ROI, cross-functional collaboration, and the critical need for upskilling provide a compelling roadmap for legal teams seeking to seize the opportunity presented by AI and redefine the future of legal practice within their organizations.

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