Trailblazing the Legal Landscape With Leadership, Culture, and AI

In this article we discuss:

• From “Outsider” to Influencer
• People and Mindset at the Core of Transformation
• The Power of East-to-West Collaboration
• The Role of Fearless Leadership
• The Excitement of a Human-Centric AI Future

The legal function has traditionally been grounded in precedent and structure—but today’s leaders are expanding that foundation to include innovation and agility. Aine Lyons, senior vice president and deputy general counsel at Workday, exemplifies this evolution.

Named one of the Financial Times’ Top 20 Legal Intrapreneurs of the Past 20 Years, Lyons offers valuable insights on shifting mindsets, cultivating cross-functional collaboration, and navigating the opportunities and challenges of applying AI to the practice of law.

She urges legal professionals to champion their own internal intrapreneurial spirit to drive meaningful change. Let’s dive into her insights.

From “Outsider” to Influencer

The legal profession lends itself to people who value structured approaches, and they can be averse to the uncertainties that accompany innovation. Lyons embraces the challenge this poses.

She recounts the early stages of a movement characterized by a push against traditional mindsets prevalent in many law firms and legal teams, where innovation was often met with resistance. "In the early days, we were definitely outsiders," Lyons reflects.

However, as the impact of their efforts to challenge the traditional way of doing things became visible—from CEOs engaging with legal departments in new ways to CFOs recognizing the efficiency gains—the mentality shift began to gain traction.

This approach, coupled with consistent progress, is ushering in a new and exhilarating phase—one that Lyons refers to as the AI revolution. 

She believes this is "one of the most exciting times... for people in the legal industry." Lyons also emphasizes the immense opportunity to change the whole practice of law positively, always with humans at the center.

People and Mindset at the Core of Transformation

Traditionally, lawyers are trained to work as individual specialists, often viewing their work as too unique —and too important—to automate. Yet, the rise of AI, particularly generative AI, has profoundly upended this perspective. While technology advances, its true value lies in how it's adopted and integrated to deliver a tangible return on investment. 

Through her experience navigating significant transformations at both VMware and Workday, Lyons realizes that the common challenges to overcome have always been cultural transformation through people and mindsets.

The hesitation about embracing innovation rears itself here as well, begging the question that Lyons found herself asking: "How do you change people's minds and inspire them about a different future?"

She sees a huge opportunity for legal professionals to elevate the work they do and have an incredible strategic advantage——as soon as they get over the AI adoption hurdle and begin leveraging solutions like contract intelligence to drive smarter, faster decisions.

This insight highlights the urgent need for comprehensive reskilling programs and robust change management strategies to ensure a transition into an AI-powered workforce that includes legal departments.

The Power of East to West Collaboration

Lyons firmly believes that legal teams cannot thrive in silos. Collaboration is paramount. 

She echoes Workday CEO Carl Eschenbach’s call for “east to west” collaboration across the business, noting that legal’s value multiplies when it's integrated into broader workflows.

When it comes to AI agents, Lyons champions a cross-functional approach. Rather than agents operating in isolation, she envisions legal agents collaborating seamlessly with those in other organizations such as sales, revenue operations, and finance to reflect the real-world flow of business deals. 

"We're all better together as functions," Lyons emphasizes, recognizing that various departments touch different parts of a deal's lifecycle, a vendor contract, or an employment matter. 

She cites a recent deal and contract transformation at Workday that involved almost six functions working together to simplify, enable speed, and deliver a better customer experience. Lyons encapsulated this philosophy in the well-known motto: "If you want to go fast, go alone. If you want to go farther, go together."

But too often, those functions operate in silos—a staggering 33% of employees still bypass Legal during contract approvals, according to the Contract Intelligence Index Report.

For Lyons, that’s a clear call to action: legal must lead not just with expertise, but with connection—bringing teams together to accelerate deals, reduce risk, and deliver better outcomes across the board.

Lyons believes the most impactful legal teams are the ones that can influence and bring other teams together to lead in critical areas of change, such as simplifying the customer experience and driving deal velocity. This collaborative spirit is crucial for breaking down organizational silos and unleashing collective innovation and impact.

The Role of Fearless Leadership

Reflecting on the impact of strong leadership, Lyons identifies the courage to challenge the status quo as paramount. She notes that a lot of change is held back by fear—fear of the future, accountability, being a first-mover, or miscalibrating risk.

She points out that “great lawyers calibrate risk effectively”. They operate with a business mindset, but a legal heart." 

This approach makes lawyers much more strategic and impactful, as legal issues are repositioned as business challenges with legal dimensions. Forward-thinking legal leaders find creative solutions with the business that are both compliant and innovative.

Lyons refers to some of the best chief legal officers (CLO) as champions of change with a fearless legal innovator mindset.

While the word fearless might seem contradictory to the risk-averse nature of legal work, Lyons clarifies that it's about a balanced perspective: "Of course, we always need to be thinking about risk, but not everything is high risk." 

It's about presenting risks to the business in a way that allows for informed decisions and mitigation strategies.

The Excitement of a Human-Centric AI Future

What excites Lyons most is Workday's commitment to reskill its entire workforce. She believes this strategy is exemplary, noting that different businesses around the world could learn from Workday's future of work approach.

This focus on reskilling is fundamental to the cultural transformation with the AI revolution, ensuring that we bring human potential along with us.

"It is very much elevating humans," Lyons asserts, emphasizing Workday's responsible AI mindset. 

Workday’s industry-leading commitment to responsible AI ensures that the value from AI is delivered with a deep care for bringing people along on the journey.

The goal is not just efficiency, but also to make work much more interesting by automating manual tasks, freeing up professionals to focus on the human skills that are going to really matter in the future. These include "judgment and leadership skills, people skills—all things that were the soft skills are now going to become the hard skills of the future,” according to Lyons.

Looking ahead, Lyons is eager to "be part of how we navigate this period of time and how we bring people along with us." 

Her vision highlights the importance of fostering human potential, building adaptive workforces, and ensuring that technological advancements serve to augment, not diminish, the human element in the workplace.

More than 40% of legal and employee respondents believe contract processes are slow. Download our Contract Intelligence Index report to understand how new innovations are driving streamlined impact, with insights from 1,250 legal practitioners and employees.