In this latest episode of Charting Change in Legal, Ari Kaplan and Caroline Hill reflect on the key themes emerging from ILTACON 2026 and the broader legal technology landscape. While generative AI continues to dominate conversations, both agree that the industry has moved towards a more mature discussion centred on implementation, governance, skills development and organisational change.
“People are having much more informed conversations. They’re able to discuss with fluency the technology that’s available, the reasons they’ve chosen one tool over another, the metrics they’re trying to capture and the leadership challenges they’re answering to,” said Kaplan, a leading legal analyst.
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A recurring theme was that technology transformation remains difficult. Although firms are becoming increasingly sophisticated in their understanding of AI and legal technology, many continue to wrestle with change management, leadership buy-in, workflow integration and measuring success. Kaplan observed that legal technology professionals now have a far more influential seat at the table, but that influence depends on engaging not just in technology discussions but also in conversations around finance, data, business strategy and organisational change.
The pair also discussed the growing importance of client engagement. Rather than making assumptions about what clients want, law firms have an opportunity to have more direct and strategic conversations with clients about service delivery, staffing models and the role of technology. Kaplan noted that clients are increasingly knowledgeable about legal technology and expect firms to use it intelligently, while continuing to value legal expertise and judgement above any particular suite of tools.
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Another key takeaway was the industry’s growing focus on talent and capability development. Hill highlighted conversations with legal innovation leaders about helping firms build long-term technology capability rather than simply selecting products. This includes rethinking training, accreditation and professional development as technology reshapes legal work.
You can listen to this fun and informative chat on Spotify and YouTube below: