Recently, Ginny Gonzalez, John Mielitz, and I had the opportunity to attend WiECON25 in Chicago, an inspiring three-day conference that brought together thought leaders, innovators, and professionals from across the legal tech and eDiscovery space. With a packed agenda and a vibrant community of attendees, the event proved to be as enriching as it was energizing.
Keynote Highlights from Maura Grossman
One of the highlights was Tuesday morning’s keynote from Maura Grossman, a pioneer in eDiscovery and a sharp, balanced voice in the ongoing discussion around artificial intelligence (AI). Her keynote struck a compelling tone with equal parts enthusiasm and caution. Grossman spoke with excitement about AI’s potential, especially in healthcare, where it could revolutionize diagnostics and medication development. But she didn’t shy away from the risks: data concentration in large organizations, loss of privacy, and the threat of social inequities shaped much of the concerns she shared.
In the context of eDiscovery, Grossman expressed apprehension about the uncritical rush into untested technologies, reminding us of the rigor that once surrounded the validation of Technology Assisted Review (TAR) and how that standard often isn’t met today. She warned of the legal system’s struggle to keep pace, especially when professionals can’t easily detect synthetic or fake content generated by modern AI tools. In addition, she noted that the legal industry shows a wide range of AI maturity with significant gaps in understanding the nuance between majority opinions and dissents, particularly in generative AI outputs.
A few fascinating AI-related cases were discussed, including a Florida judge using VR glasses to assess a self-defense scene and a pro se litigant in New York seeking to use an avatar to present their appellate argument. These cases highlighted the rapid and sometimes unexpected intersections between law and emerging tech.
Grossman also offered practical guidance for navigating this new landscape: develop a foundational understanding of machine learning, data processing, and statistics. Embrace what she called the “Three Cs”; Creativity, Communication, and Collaboration, and then commit to lifelong learning. Her parting advice? “Read an hour a day on things you don’t know.”
Making the Most of WiECON25
Beyond the sessions, WiECON25 offered numerous opportunities to connect. From the lively opening reception to a stunning semi-formal awards Gala that honored trailblazing women in the industry, the social events were as memorable as the programming. My colleague Ginny Gonzalez, TCDI’s Chief Revenue Officer, was honored as a nominee for the Guiding Light Award during the Gala this year, and it was wonderful to support not only her accomplishments but those of the whole WiE community.
Breakout sessions spanned a wide range of topics, from mental health and personal branding to data privacy, legal ops, and the evolution of the EDRM. Throughout the entire conference, the atmosphere was one of reinvention, reflection, and forward momentum.
I also had the pleasure of sharing on the importance of empathy in leadership during the panel, “The Engagement Advantage: Leading with Trust and Empowerment.” Joined by fellow panelists, Jennifer Griffith (Beacon Hill Legal), Martie Meyer (Cimplifi), and Deedra Smith (FTI Consulting), we discussed how to be more compassionate leaders within our realm of influence. The session also included some role-play exercises from the stage to demonstrate what it looks like to guide those around you with considerate communication. It was a moving exercise, and I am humbled to have been asked to share!
All in all, WiECON25 was more than just a conference, it was a call to adapt, lead, and rethink the future of our profession.
Connie Smith
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Connie has enjoyed a lifelong career in the legal and technology industries. Connie is a graduate of The University of North Carolina School of Law and The University of North Carolina – Kenan-Flagler School of Business. Her experience as an attorney in private practice and in-house counsel provides a unique and valued perspective when evaluating the individual needs of each client and project. Learn more about Connie.
