From Basement to Boardroom

The traditional image of the IT department relegated to the basement is rapidly becoming obsolete. At ILTACON 2025's G100/G200 Recap, a panel of seasoned CIOs revealed how technology leaders are ascending to the C-suite and driving strategic transformation across law firms, with artificial intelligence serving as both catalyst and challenge.   

The CIO panelists providing the Thursday morning keynote recap of the G100 and G200 programs were Karen Campbell from Foley Hoag, James McKenna from Fenwick & West LLP, Michael Bruckner from Duane Morris LLP, and Andrew Powell from Macfarlanes.  

The Rise of the Technology Executive 

The session opened with a striking observation that signals a fundamental shift in the legal industry: CIOs are increasingly moving into Chief Operating Officer roles, marking a new era in how law firms view technology leadership. As Jim McKenna noted, there's an old joke that "CIO stands for career is over," but that narrative is changing dramatically. "For the first time, the knowledge of how stuff works and what can work well at your firm is something that can help lead your firm”. This evolution reflects technology's transformation from a mere support function to the lifeblood of legal operations. The driving force behind this shift is unmistakable: technology and business operations have become indistinguishable. Firms that embrace this reality are positioning themselves for success in an increasingly competitive landscape, where technological sophistication often determines market advantage. 

Managing Change Fatigue in a Rapid-Fire World   

Perhaps no challenge resonates more deeply with technology leaders today than change fatigue. The session addressed the very real phenomenon of departments overwhelmed by constant requests for new tools and implementations, a situation that has become endemic across the legal industry. The solution, panelists suggested, lies in having the courage to ask "why", understanding the business purpose behind each technology request rather than simply responding to fear of missing out (FOMO). This approach requires technology leaders to act as strategic filters, distinguishing between genuine business needs and the latest technological trends. The most successful CIOs are those who can balance innovation with operational stability, ensuring that change serves a clear business purpose rather than change for its own sake. 

The AI Imperative: Olympic Rings, Not One Ring to Rule Them All 

The discussion of artificial intelligence adoption revealed a nuanced reality far from the "one solution to solve it all" mentality that often dominates technology conversations. Jim McKenna introduced a compelling metaphor that reframes how law firms should approach AI implementation: Olympic rings versus the Lord of the Rings approach. “You will have multiple rings," McKenna explained. "The goal isn't to have all the rings. But like the Olympic logo, you're going to have a number of rings that overlap, and they work with each other." This multi-tool approach acknowledges that different AI solutions excel at various tasks, and successful firms will orchestrate multiple specialized tools rather than waiting for a single comprehensive solution. The inevitability of AI's impact is no longer in question; the conversation has shifted to managing the "what" and "how." Some firms are finding success by focusing initially on the business of law rather than the practice of law, using administrative functions as testing grounds for AI implementation before expanding to legal work. This strategy allows firms to build confidence and expertise in lower-risk environments while developing the organizational capabilities needed for more complex applications.   

Security in the Age of Deep Fakes   

The security implications of AI advancement painted a sobering picture during the session. Attendees witnessed a live demonstration of deep fake technology. The ability to mimic voices and appearances with increasing sophistication creates unprecedented social engineering risks, particularly for help desk operations and password management systems. The threat landscape extends far beyond traditional hacking approaches. Access to calendar information, project names, and meeting agendas can provide valuable intelligence without requiring actual data theft, creating new vulnerabilities that firms must address. This evolution in security threats requires CIOs to rethink their defensive strategies entirely. Traditional security measures designed for human-to-human interactions may prove inadequate against AI-powered attacks that can convincingly impersonate trusted individuals or create compelling but fabricated evidence. 

Cloud Adoption: Reality Check 

ILTA's cloud adoption survey delivered a reality check that many in attendance found uncomfortably familiar. The data revealed a persistent gap between ambition and execution across the legal industry. While email security has achieved near-universal SaaS adoption, practice management systems lag significantly behind, highlighting the complexity of modernizing core legal operations. Perhaps most tellingly, the survey revealed that CIOs consistently underestimate their implementation timelines, with actual progress falling short of the previous year's projections. This pattern suggests that the challenges of cloud migration are more complex than many technology leaders initially anticipate. Interestingly, the primary barrier to cloud migration isn't security concerns. Instead, the "complexity of what you have already" emerged as the dominant challenge, requiring firms to untangle decades of accumulated technical debt before they can successfully transition to cloud-based solutions. 

Looking Forward: Embracing Inevitable Change 

IThe session concluded with a message that was both sobering and energizing: the pace of technological change will only accelerate. The days of comfortable quarterly planning cycles may end, replaced by a continuous cycle of experimentation, measurement, and adaptation that demands new organizational capabilities. "It's never been more exciting. It's never been more confusing," McKenna summarized, capturing the paradox that defines the current moment for technology leaders. For CIOs navigating this landscape, success requires embracing a "fast failure mentality" while maintaining the operational excellence that keeps firms running smoothly. The transformation from basement to boardroom reflects technology's evolution from support function to strategic differentiator. As artificial intelligence reshapes the legal industry, technology leaders who can balance innovation with operational stability will find themselves not just in the boardroom but leading the conversation about their firms' futures. This new era demands CIOs who can translate technological possibilities into business realities while managing the human and organizational challenges that inevitably accompany significant change. The firms that recognize and embrace this evolution will be best positioned to thrive in an increasingly technology-driven legal landscape.