alt.legal: Car Bombs With Casey And The Crew

Insights on innovation from legal tech guru Casey Flaherty, live from ILTACON.

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’Keefe; Matt 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?”

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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.

The next Guinness came as a boilermaker—beer with a side of whisky. Greg noted that we really should be doing car bombs, which are whisky and Bailey’s with beer, instead of boilermakers. (Later, we would get several rounds of car bombs.)

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I switched topics. “So we talk about change, about law firms and legal departments improving around process and technology. Have you seen it get any better?”

“Yes, it’s getting a little better, but it’s not really scaling,” said Casey. “People have gotten better in recognizing that while technology can be essential, it’s not a quick fix. Some people are looking at process and trying to be better.”

“But,” Casey noted, “finding people who are doing this is hard, and you can find some people doing this well from within that group. It’s still a minority of a minority.”

Casey went on to explain that in the process of consulting and evaluating firms on some of their basic technology skills and capabilities, some respondents are shockingly behind the times even in their affirmative responses. “One of the questions on my list is about what innovation initiatives are happening at the firm. Sometimes firms will mention the fact that they changed their website! One firm actually dropped in this long description of ways they were using ROSS, an AI tool on the market. Well that’s great, except that ROSS’s main use case is in bankruptcy, and this firm does zero bankruptcy work. None at all.”  He chuckled and shook his head. “They just put some stuff in their answer because, I don’t know, they think I’m an idiot?”

Casey explained that a lot of law firms will push back on his queries, claiming that he was focusing on areas that aren’t really the real work. “If it shows up on the bill, it’s real enough to me. What they are really saying is that some of those areas are where lawyers don’t add value, which is where we agree. But in those areas, so much time is wasted.”

(And if you’re wondering what types of skills we’re talking about here, check out the website for Casey’s firm, Procertas (www.procertas.com). One example is using the right functions in Word so that an attorney is not billing hours of time just re-numbering sections in an agreement. Procertas has a legal technology assessment that tests whether lawyers have basic proficiencies in the tools of their trade, like Word, Excel and PDF.)

We dropped some car bombs to Greg’s satisfaction, knocked them back, and continued the conversation.

“Why aren’t corporates driving more change?  Why don’t they start asserting pressure on their law firms to be better?” I asked.

Casey said, “Clients are just as change- and risk-averse as their law firms. We have some serious agency problems. The data shows that in-house counsel are growing their headcount like crazy. But that growth is almost purely labor arbitrage, without any thought towards how the services are being delivered. As Bill Henderson points out, we think we have a cost problem when we actually have a productivity problem. When you think of it as a price problem, you aren’t addressing the real issue.”

I pondered this silently. Casey took a swig of his beer and continued.

“Pricing has inherent problems in law, because legal practice is a credence good. The value is almost impossible to measure, so we tend to base our view on reputation and other proxies. And in a credence good market, the higher the price, the higher the perceived value.”

Now he was getting into his zone, and the ideas were flowing. “The fact that some clients have started to do something is reflected by how they are working with alternative legal services and technology. But it’s still not close to being mature. Think about Pangea3 or Axiom. These businesses are really successful, but they should be way bigger. They aren’t as big as they should be.”

I asked, “So who holds the keys to solving this? Do law firms need to get pushed by a new model disrupting their space? Or do the corporate counsel need to be the ones to push change?”

“Well,” Casey said, “I work with the corporates, so that’s my focus. I’m trying to change the buy-side. Sellers don’t really respond to me. There really needs to be action, but it’s been a buyer’s market for a decade now and not much has changed. The buyers have the power, and the bad behavior is coming from them too.”

“And how does that change really happen? What do you need to really make those changes take hold?”

“You need a mandate for that change, from the top. Look, not all of my consulting engagements go well. We have some failures. The difference between those that went well and those that didn’t is always a person in a position of authority, saying ‘this is happening, we have to do this.’”

I pressed harder. “But if you had two magic steps that would make the difference, two things that could really spark a lot of change, what are they?”

“First of all, find someone where a reasonable part of their job description is to improve. This person needs to dedicate real time to solving this.  Then, the second thing is whatever that person believes is the right action.  I present options in menus, but I don’t have a mindset of being prescriptive.  It’s different for everybody.”

The night spun on into a blur of brainstorming, lively discussion, and a considerable amount of drinking. These nights are my favorite part of ILTA. Like I said at the top—it’s hard to capture how great these conversations are. It’s not idle chatter, it doesn’t have the feeling of waxing eloquent without substance. It doesn’t feel like we’re just gabbing about cockeyed ideas.

It feels like we are the fraternity of challengers, conspiring to solve the problems of the legal ecosystem with every car bomb we drop.


Ed Sohn is VP, Product Management and Partnerships, for Thomson Reuters Legal Managed Services. After more than five years as a Biglaw litigation associate, Ed spent two years in New Delhi, India, overseeing and innovating legal process outsourcing services in litigation. Ed now focuses on delivering new e-discovery solutions with technology managed services. You can contact Ed about ediscovery, legal managed services, expat living in India, theology, chess, ST:TNG, or the Chicago Bulls at edward.sohn@thomsonreuters.com or via Twitter (@edsohn80). (The views expressed in his columns are his own and do not reflect those of his employer, Thomson Reuters.)

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