D. Casey Flaherty

The wheel of legal tech conferences turns on two main events every year: Legal Tech New York, in February, and ILTACON, usually in August. These conferences draw both vendors and clients together in a whirlwind of meetings, keynotes, panels, and demos.

On some nights, drinks are involved.  Like last night, for example. And on nights when drinks get involved, a spirited discussion with Casey Flaherty is just around the corner.

For those who may not recall, Casey, of House Flaherty, First of His Name, is Uber Nerd of the Lawyers and Transformer of the Legal Realm. He runs a consultancy that helps corporate legal departments assess the competencies of their outside counsel and improve their relationships using metrics.

I really like hanging out with Casey at conferences. It’s hard to do justice to our conversations in these recaps, and my note-taking skills tend to degrade a little after the fourth round of drinks. Back in February, we sat in the lobby of the New York Hilton, poured some brown liquor, and talked about how law departments are making changes — and how slow those changes are to advance.

This time around, we sat in Ri Ra, an Irish pub nestled in the walkway that connects the classy Mandalay Bay to the depressing pyramid they call Luxor. A Celtic-influenced band featured a lot of mandolin in their songs, and off to the side, there was a comfy room with throwback furniture and vintage shelf adornments. We were not alone—the room was filled with a host of the most interesting players and voices in legal technology, like my old boss and mentor, the esteemed Greg McPolin; the original legal blogger and AboveTheLaw columnist, Kevin O’KeefeMatt Homann of Filament; and several others that dipped in and out of the room.

We ordered a couple of Guinesses, and I started by asking Casey about the topic du jour at ILTA: AI. “What are your thoughts on AI?”

Everyone rolled their eyes and groaned. Casey said, “I am very tired of robot magic silliness. It sucks up the oxygen in conferences like this. You have people sent here to investigate AI, wasting their time when they could be learning about something more useful. You have vendors that are doing good work with real value, but they are wasting their time talking about AI to people that aren’t really buying it.”

Matt added, “The quicker people realize what these tools are, the quicker that we can be done talking about AI.”

Casey said, “Look, I like some of the platforms out there, and I try to go out of my way to say so.  But really, the question comes down to whether it’s better, whether the outcomes are actually improved.”

We all agreed that there was too much hype about AI, and at a place like ILTA, which can sometimes become an echo chamber, perhaps there’s already too much hype around pointing out that there’s too much hype about AI. I know, we’re real meta.