Putting complex and often intimidating topics into context.


Chapter 8, Technology

No discussion on contracting process improvements is complete without focusing on technology. Scarcely a day goes by without an article, blog, or webinar on legal technology and, more specifically, about artificial intelligence (AI). There are many conferences and webinars about contract management systems—on selecting them, on what to use them for, how to derive greatest benefit, etc. Usually, those educational programs are provided or delivered by the contract management systems providers.

Technology is always at the core of any discussion about innovation, for example, but I maintain it should not be. Before any conversation about technology takes place, there should be an assessment of the current state of the people and processes involved in contracting, which is why this chapter follows my previous chapters on People and Process. Only after a thorough review takes place, and there is agreement within the organization that the right people are doing the right steps in the best order, should a discussion about technology begin.
Continue Reading CLM Simplified Part IV: Technology, Metrics & Data, and Outsourcing (272)


Trading ego for effectiveness, friendship, and purpose.


Joe Borstein and Paul Stroka asked me to get naked with them. I said yes. Then Bill asked me to write about it. So here we are.

Now that you’re hooked by the clickbait headline and the tease, we must, naturally, commence with an anecdotal aside before I explain why the platitudinous “our customers are our business” is especially true for LexFusion, why “everyone talks to us because everyone talks to us,” and what these say about the evolution of the  broader legal innovation ecosystem.
Continue Reading Getting naked with colleagues and clients (267)

Source:  Gravity Stack [Click on to enlarge]

Sophisticated investors are betting on contract tech. It’s about business, not the intricacies or importance of law.


Today’s post (256) and last week’s (255) are a two-part series on the burgeoning legal tech sector.

Whereas Post 255 focused on the explosion in the legal technology market over the past year—five new #Legaltech Unicorns, three companies go public—this post looks contract tech, which is arguably legal tech’s hottest subsector.
Continue Reading Because Everyone Else Cares: Why legal should be paying attention to contracts (256)

[click on to enlarge]

Five New #Legaltech Unicorns.  One Unicorn Nearly Doubles in Value.  Three Companies Go Public. 


It might be unfair to say that legal technology arrived in 2021. After all, law firms and law departments, the primary target buyers of legal tech, have been preparing for the impact of AI and automation.

In 2018, Amlaw 100 firms like Reed Smith and later Wilson Sonsini began creating dedicated tech-focused subsidiaries. See Post 213 (Zach Abramowitz’s overview of law firm-led legal tech.  In late 2019, the chairman of an AmLaw 50 firm told us, “We know there is new stuff, we know that our clients know about the new stuff. The question is how we become proactive so that our clients don’t bypass us on the way to the new stuff.”
Continue Reading How the first half of 2021 signals the maturity of an ecosystem (255)

Source: Rob Saccone, Nexlaw Partners

We’re on the ground floor of digital services.


I didn’t like Alexa at first. If she were my assistant, she would have likely ended up on a performance improvement plan had our working relationship not improved.

Over time we grew to better understand each other, and we now converse multiple times a day about news, weather, sports, music, and impulse purchases. My wife and kids have also become everyday users, and in a twist of fate, I occasionally find myself scolding my teens for yelling at Alexa as if she were a family friend instead of a glowing tube of snark and overnight deliveries.
Continue Reading Platform (r)evolution: how the convergence of talent and technology will reshape service organizations (248)


An early example of where things are headed.


In Post 228, Paula Doyle, Chief Legal Innovation Officer at the World Commerce and Contracting Association (WorldCC), made the claim that inefficiencies in the current commercial contracting process likely cost the global economy more than $1 trillion annually. We reach this figure by adding up the massive second-order effects caused by excessive contract complexity and poor process:
Continue Reading Case study: impact of AI and Big Data on low-risk contract negotiations (236)

Photo by Maarten van den Heuvel on Unsplash

For the legal industry, the answer is likely “now.”


Lawyers love the expression “better, faster, cheaper—pick two.”  But what happens when there is a change in the state of the art such that gains in all three are possible and the only constraint is a workforce with the requisite state-of-the-art skills?
Continue Reading When is a generational strategy the best strategy? (235)


Lawyers are trained to be good at what machines can’t do.


Will the world still need lawyers once AI gets really good?

The short answer is yes—and I believe it will still be yes no matter how good AI gets.  My view is not universally accepted, so I will need to lay it out, and that will involve some claims about what humans are and whether a machine can ever be like that.  This will shed considerable light on what lawyers essentially do, and help us to see how machines can help us to be better lawyers.
Continue Reading Legal’s AI rocket ship will be manned (book review) (232)


A crowded, chaotic landscape in love with the future.


The opening graphs of Richard Susskind’s Tomorrow’s Lawyers (2nd ed. 2016) predict the revolution that is now underway:

This book is a short introduction to the future for young and aspiring lawyers.

Tomorrow’s legal world, as predicted and described here, bears little resemblance to that of the past. Legal institutions and lawyers are at a crossroads, I claim, and will change more radically in less than two decades than they have over the past two centuries. If you’re a young lawyer, this revolution will happen on your watch. (p. xvii)

Indeed, only a revolution could explain the above “market map,” which reflects literally hundreds of point solutions for a rapidly expanding one-to-many legal marketplace.
Continue Reading The best metaphor for today’s legal market is the auto industry circa 1905 (231)