Legal IT Insider recently hosted a webinar with Tara Daisy, managing director for legal at Box and former director of data delivery at Cooley, to discuss how law firms are approaching content management, collaboration and AI at a time of rapid technological change.
The session, titled A Practitioner’s Perspective on Building Connected Legal Workflows, drew heavily on Daisy’s experience leading technology initiatives at Cooley before joining Box earlier this year.
A recurring theme throughout the discussion was the challenge facing firms as they try to rationalise increasingly complex technology estates while simultaneously preparing for AI-powered workflows.
Reflecting on Cooley’s decision a few years ago to adopt Box for external collaboration, Daisy said the firm had been driven by a combination of rising costs, usability concerns and pressure from clients to work within platforms they already used.
“We wanted to make sure we were evaluating a product that was very easy for our clients to use,” she said, noting that many of Cooley’s technology-sector clients were already Box users. “A lot of our clients were using it. So it was a very easy transition for us to say we’re willing to try something outside of what would be considered traditional legal tech.”
The conversation explored a broader shift taking place across the legal sector, where clients are increasingly influencing technology decisions through outside counsel guidelines and workflow requirements.
Daisy argued that firms are moving away from isolated point solutions toward more connected information ecosystems, particularly as AI places greater emphasis on data quality, governance and context.
“AI isn’t a magic wand,” was one of the central messages of the session. Daisy spoke candidly about the reality that many firms are struggling with fragmented content, inconsistent processes and uncertainty over which technologies to adopt.
“Everyone is just overwhelmed, full stop,” she said. Referring to a talk she gave at ILTACON, she recalled saying ‘raise your hand if you’re having a million AI conversations’, observing, “and all the hands went up. ‘Raise your hand if you’re sick of talking about it?’ and all the hands went up.”
The webinar also touched on the growing importance of interoperability. Daisy said that firms increasingly expect technology providers to work alongside one another rather than operate in silos, particularly as legal organisations experiment with a growing range of AI tools.
According to Daisy, one of the strongest themes at ILTACON 2026 was the extent to which firms, vendors and consultants were collaborating to solve common challenges around AI adoption, governance and information management.
“If it’s not going to play together, if you’re not going to intersect with other technologies and other platforms, you’re going to get left behind,” she said.
Among the topics discussed were Box Hubs, content governance, document version control, legal-specific AI initiatives, integrations with platforms such as Microsoft, Harvey and Legora, and the growing interest among firms in alternative approaches to document management systems.
Daisy also suggested that many firms are beginning to evaluate technology decisions within the context of longer-term transformation strategies rather than viewing deployments as standalone projects.
“The biggest challenge for people is understanding how are we going to work differently versus can the technology do the thing we need it to do,” she said.
Watch the full replay below: